# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_skg1
_database_code_depnum_ccdc_archive 'CCDC 1427878'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;
_audit_creation_date             2014-05-30
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H28 O3'
_chemical_formula_sum            'C29 H28 O3'
_chemical_formula_weight         424.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C29O3H28
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4846(6)
_cell_length_b                   15.8614(8)
_cell_length_c                   14.7350(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.128(5)
_cell_angle_gamma                90
_cell_volume                     2419.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.7000
_cell_measurement_theta_min      3.0450
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.5
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8529
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.930
_diffrn_reflns_theta_min         4.123
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 8.3200
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9780
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   63.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   33.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega -152.00 -126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289 -116.0000 -137.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   75.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289  126.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289 -126.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   68.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289 -126.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  7 omega  -30.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289   30.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
  8 omega   60.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289   30.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  9 omega   19.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -92.0000 -150.0000 138

#__ type_ start__ end____ width___ exp.time_
 10 omega  119.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   50.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  178.0000 -120.0000 115

#__ type_ start__ end____ width___ exp.time_
 12 omega   66.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   50.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega   31.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   44.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 15 omega   51.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -50.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega   14.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 17 omega   13.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 18 omega   46.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   10.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000   30.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1440976000
_diffrn_orient_matrix_UB_12      -0.0048186000
_diffrn_orient_matrix_UB_13      0.0093663000
_diffrn_orient_matrix_UB_21      0.0013352000
_diffrn_orient_matrix_UB_22      -0.0957886000
_diffrn_orient_matrix_UB_23      -0.0169852000
_diffrn_orient_matrix_UB_31      0.0370685000
_diffrn_orient_matrix_UB_32      -0.0151986000
_diffrn_orient_matrix_UB_33      0.1041273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3173
_reflns_number_total             4488
_reflns_odcompleteness_completeness 99.47
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.041
_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)+(0.0692P)²+0.1385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1393
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C10(H10A,H10B), C10(H10C,H10D)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C28(H28), C22(H22), C17(H17), C25(H25), C27(H27), C6(H6),
 C5(H5), C24(H24), C18(H18), C21(H21), C20(H20), C1(H1), C2(H2), C19(H19)
3.c X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C11(H11A,H11B,H11C), C11A(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38148(11) 0.40940(9) 0.79415(7) 0.0721(4) Uani 1 1 d . . . . .
O2 O 0.25890(13) 0.35484(9) 0.67002(8) 0.0835(4) Uani 1 1 d . . . . .
O3 O 0.65878(16) -0.04254(10) 0.97731(10) 0.1021(5) Uani 1 1 d . . . . .
C7 C 0.53685(16) 0.47127(11) 0.66327(11) 0.0653(4) Uani 1 1 d . . . . .
H7 H 0.6116 0.4715 0.6367 0.078 Uiso 1 1 calc R U . . .
C23 C 0.57134(16) 0.15948(11) 0.79756(11) 0.0634(4) Uani 1 1 d . . . . .
C12 C 0.50919(17) 0.32569(12) 0.60351(11) 0.0671(4) Uani 1 1 d . . . . .
C3 C 0.60252(19) 0.60312(13) 0.74584(13) 0.0784(5) Uani 1 1 d . . . . .
H3 H 0.6879 0.5857 0.7496 0.094 Uiso 1 1 calc R U . . .
C14 C 0.53289(16) 0.24208(11) 0.64728(11) 0.0639(4) Uani 1 1 d . . . . .
C26 C 0.62434(19) 0.02079(12) 0.91528(12) 0.0739(5) Uani 1 1 d . . . . .
C4 C 0.50403(16) 0.55161(11) 0.70317(11) 0.0632(4) Uani 1 1 d . . . . .
C28 C 0.51426(18) 0.08166(12) 0.77627(13) 0.0754(5) Uani 1 1 d . . . . .
H28 H 0.4568 0.0755 0.7217 0.091 Uiso 1 1 calc R U . . .
C13 C 0.5161(2) 0.34052(15) 0.51511(13) 0.0931(7) Uani 1 1 d . . . . .
H13A H 0.5367 0.2970 0.4777 0.112 Uiso 1 1 calc R U . . .
H13B H 0.5002 0.3944 0.4910 0.112 Uiso 1 1 calc R U . . .
C22 C 0.54936(16) 0.23476(11) 0.73933(11) 0.0643(4) Uani 1 1 d . . . . .
H22 H 0.5464 0.2853 0.7710 0.077 Uiso 1 1 calc R U . . .
C17 C 0.30362(19) 0.15013(14) 0.55405(13) 0.0806(6) Uani 1 1 d . . . . .
H17 H 0.2995 0.1773 0.6095 0.097 Uiso 1 1 calc R U . . .
C25 C 0.6789(2) 0.09830(14) 0.93904(12) 0.0808(6) Uani 1 1 d . . . . .
H25 H 0.7346 0.1045 0.9944 0.097 Uiso 1 1 calc R U . . .
C27 C 0.5403(2) 0.01281(13) 0.83389(14) 0.0812(5) Uani 1 1 d . . . . .
H27 H 0.5011 -0.0388 0.8177 0.097 Uiso 1 1 calc R U . . .
C6 C 0.3518(2) 0.65770(14) 0.73219(15) 0.0873(6) Uani 1 1 d . . . . .
H6 H 0.2670 0.6766 0.7269 0.105 Uiso 1 1 calc R U . . .
C5 C 0.37778(18) 0.58090(13) 0.69572(13) 0.0746(5) Uani 1 1 d . . . . .
H5 H 0.3102 0.5483 0.6658 0.090 Uiso 1 1 calc R U . . .
C9 C 0.35902(16) 0.38505(11) 0.70665(11) 0.0613(4) Uani 1 1 d . . . . .
C24 C 0.65217(19) 0.16617(12) 0.88208(11) 0.0750(5) Uani 1 1 d . . . . .
H24 H 0.6888 0.2181 0.9001 0.090 Uiso 1 1 calc R U . . .
C18 C 0.1913(2) 0.12089(16) 0.50167(16) 0.0981(7) Uani 1 1 d . . . . .
H18 H 0.1128 0.1274 0.5227 0.118 Uiso 1 1 calc R U . . .
C21 C 0.4219(2) 0.10133(17) 0.44202(15) 0.1048(8) Uani 1 1 d . . . . .
H21 H 0.5002 0.0942 0.4210 0.126 Uiso 1 1 calc R U . . .
C15 C 0.54455(18) 0.16829(13) 0.58416(12) 0.0754(5) Uani 1 1 d . . . . .
H15A H 0.6054 0.1832 0.5436 0.090 Uiso 1 1 calc R U . . .
H15B H 0.5808 0.1210 0.6213 0.090 Uiso 1 1 calc R U . . .
C20 C 0.3101(3) 0.07336(18) 0.38893(17) 0.1145(9) Uani 1 1 d . . . . .
H20 H 0.3135 0.0482 0.3323 0.137 Uiso 1 1 calc R U . . .
C16 C 0.42038(18) 0.13980(11) 0.52582(11) 0.0702(5) Uani 1 1 d . . . . .
C8 C 0.47398(16) 0.39778(11) 0.65983(10) 0.0606(4) Uani 1 1 d . . . . .
C1 C 0.4503(2) 0.70634(16) 0.77627(16) 0.0993(7) Uani 1 1 d . . . . .
H1 H 0.4323 0.7577 0.8020 0.119 Uiso 1 1 calc R U . . .
C2 C 0.5761(2) 0.67929(15) 0.78252(16) 0.0991(7) Uani 1 1 d . . . . .
H2 H 0.6432 0.7127 0.8117 0.119 Uiso 1 1 calc R U . . .
C29 C 0.6123(3) -0.12419(15) 0.9539(2) 0.1200(9) Uani 1 1 d . . . . .
H29A H 0.6417 -0.1621 1.0036 0.180 Uiso 1 1 calc R U . . .
H29B H 0.6439 -0.1427 0.8996 0.180 Uiso 1 1 calc R U . . .
H29C H 0.5196 -0.1235 0.9427 0.180 Uiso 1 1 calc R U . . .
C10 C 0.2757(2) 0.40440(16) 0.84653(14) 0.0877(6) Uani 1 1 d . . . . .
H10A H 0.2243 0.3546 0.8286 0.105 Uiso 0.512(19) 1 calc R U P A 1
H10B H 0.2206 0.4535 0.8341 0.105 Uiso 0.512(19) 1 calc R U P A 1
H10C H 0.2570 0.4597 0.8693 0.105 Uiso 0.488(19) 1 calc R U P A 2
H10D H 0.1986 0.3831 0.8084 0.105 Uiso 0.488(19) 1 calc R U P A 2
C19 C 0.1949(3) 0.08237(15) 0.41893(17) 0.1023(8) Uani 1 1 d . . . . .
H19 H 0.1193 0.0626 0.3837 0.123 Uiso 1 1 calc R U . . .
C11 C 0.3273(9) 0.4005(10) 0.9441(5) 0.114(3) Uani 0.512(19) 1 d . . P A 1
H11A H 0.3701 0.3474 0.9578 0.171 Uiso 0.512(19) 1 calc R U P A 1
H11B H 0.2580 0.4059 0.9791 0.171 Uiso 0.512(19) 1 calc R U P A 1
H11C H 0.3879 0.4456 0.9597 0.171 Uiso 0.512(19) 1 calc R U P A 1
C11A C 0.3158(10) 0.3488(13) 0.9207(11) 0.141(6) Uani 0.488(19) 1 d . . P A 2
H11D H 0.3234 0.2928 0.8975 0.211 Uiso 0.488(19) 1 calc R U P A 2
H11E H 0.2531 0.3492 0.9616 0.211 Uiso 0.488(19) 1 calc R U P A 2
H11F H 0.3979 0.3668 0.9532 0.211 Uiso 0.488(19) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3306(19) . ?
O1 C10 1.450(2) . ?
O2 C9 1.2013(19) . ?
O3 C26 1.368(2) . ?
O3 C29 1.407(3) . ?
C7 C4 1.467(2) . ?
C7 C8 1.336(2) . ?
C23 C28 1.386(3) . ?
C23 C22 1.467(2) . ?
C23 C24 1.395(2) . ?
C12 C14 1.478(2) . ?
C12 C13 1.337(2) . ?
C12 C8 1.493(2) . ?
C3 C4 1.387(3) . ?
C3 C2 1.370(3) . ?
C14 C22 1.345(2) . ?
C14 C15 1.512(2) . ?
C26 C25 1.378(3) . ?
C26 C27 1.377(3) . ?
C4 C5 1.391(2) . ?
C28 C27 1.384(3) . ?
C17 C18 1.382(3) . ?
C17 C16 1.364(3) . ?
C25 C24 1.366(3) . ?
C6 C5 1.376(3) . ?
C6 C1 1.368(3) . ?
C9 C8 1.494(2) . ?
C18 C19 1.369(3) . ?
C21 C20 1.375(3) . ?
C21 C16 1.380(2) . ?
C15 C16 1.511(2) . ?
C20 C19 1.359(3) . ?
C1 C2 1.376(3) . ?
C10 C11 1.455(8) . ?
C10 C11A 1.415(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C10 117.85(14) . . ?
C26 O3 C29 117.90(18) . . ?
C8 C7 C4 128.85(16) . . ?
C28 C23 C22 124.78(15) . . ?
C28 C23 C24 116.70(17) . . ?
C24 C23 C22 118.49(16) . . ?
C14 C12 C8 118.93(14) . . ?
C13 C12 C14 123.47(18) . . ?
C13 C12 C8 117.59(18) . . ?
C2 C3 C4 121.04(19) . . ?
C12 C14 C15 116.78(14) . . ?
C22 C14 C12 120.21(15) . . ?
C22 C14 C15 122.92(17) . . ?
O3 C26 C25 115.51(17) . . ?
O3 C26 C27 125.40(19) . . ?
C27 C26 C25 119.08(18) . . ?
C3 C4 C7 119.23(16) . . ?
C3 C4 C5 118.03(18) . . ?
C5 C4 C7 122.64(17) . . ?
C27 C28 C23 121.87(16) . . ?
C14 C22 C23 130.04(16) . . ?
C16 C17 C18 121.07(19) . . ?
C24 C25 C26 120.70(17) . . ?
C26 C27 C28 119.91(19) . . ?
C1 C6 C5 120.2(2) . . ?
C6 C5 C4 120.66(19) . . ?
O1 C9 C8 112.11(14) . . ?
O2 C9 O1 123.98(16) . . ?
O2 C9 C8 123.90(15) . . ?
C25 C24 C23 121.66(18) . . ?
C19 C18 C17 120.4(2) . . ?
C20 C21 C16 121.5(2) . . ?
C16 C15 C14 115.78(15) . . ?
C19 C20 C21 120.2(2) . . ?
C17 C16 C21 117.66(18) . . ?
C17 C16 C15 121.64(16) . . ?
C21 C16 C15 120.70(18) . . ?
C7 C8 C12 121.68(15) . . ?
C7 C8 C9 121.97(16) . . ?
C12 C8 C9 116.21(15) . . ?
C6 C1 C2 120.0(2) . . ?
C3 C2 C1 120.0(2) . . ?
O1 C10 C11 109.4(4) . . ?
C11A C10 O1 106.7(4) . . ?
C20 C19 C18 119.2(2) . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_barc002
_database_code_depnum_ccdc_archive 'CCDC 1427900'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9.67 Br0.33 Cl0.33 N0.33 O1.33'
_chemical_formula_weight         206.31

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   10.4479(2)
_cell_length_b                   20.6292(3)
_cell_length_c                   27.0817(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5836.97(16)
_cell_formula_units_Z            24
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15919
_cell_measurement_theta_min      3.9017
_cell_measurement_theta_max      71.9795

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2544
_exptl_absorpt_coefficient_mu    3.072
_exptl_absorpt_correction_T_min  0.4305
_exptl_absorpt_correction_T_max  0.5647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41345
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0126
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         72.13
_reflns_number_total             5728
_reflns_number_gt                4946
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0581P)²+3.1700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5728
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.99562(3) 0.129327(19) 0.264013(11) 0.08555(15) Uani 1 1 d . . .
Cl1 Cl 0.08767(7) 0.57046(4) 0.03916(3) 0.0799(2) Uani 1 1 d . . .
O1 O 0.73618(18) 0.08572(8) 0.04049(6) 0.0669(5) Uani 1 1 d . . .
O2 O 0.99668(17) 0.26158(11) 0.04743(8) 0.0775(6) Uani 1 1 d . . .
O3 O 0.46177(18) 0.30431(9) 0.17958(7) 0.0664(4) Uani 1 1 d . . .
O4 O 0.35350(16) 0.24790(9) 0.12259(8) 0.0716(5) Uani 1 1 d . . .
N1 N 0.89022(19) 0.16449(10) 0.04325(7) 0.0548(5) Uani 1 1 d . . .
C1 C 0.9996(3) 0.12168(16) 0.05057(13) 0.0774(9) Uani 1 1 d . . .
H1A H 0.9972 0.1039 0.0841 0.116 Uiso 1 1 calc R . .
H1B H 1.0790 0.1462 0.0459 0.116 Uiso 1 1 calc R . .
H1C H 0.9960 0.0862 0.0266 0.116 Uiso 1 1 calc R . .
C2 C 0.7654(2) 0.14246(11) 0.04189(7) 0.0515(5) Uani 1 1 d . . .
C3 C 0.6785(2) 0.20087(10) 0.04443(8) 0.0489(5) Uani 1 1 d . . .
H3 H 0.6084 0.1966 0.0195 0.059 Uiso 1 1 calc R . .
C4 C 0.62018(19) 0.20749(9) 0.09697(8) 0.0438(4) Uani 1 1 d . . .
H4 H 0.5468 0.1765 0.0990 0.053 Uiso 1 1 calc R . .
C5 C 0.56551(19) 0.27518(9) 0.10369(8) 0.0441(4) Uani 1 1 d . . .
C6 C 0.6167(2) 0.32795(10) 0.08289(8) 0.0464(4) Uani 1 1 d . . .
C7 C 0.7379(2) 0.32384(11) 0.05271(9) 0.0571(5) Uani 1 1 d . . .
H7A H 0.8108 0.3365 0.0739 0.069 Uiso 1 1 calc R . .
H7B H 0.7324 0.3558 0.0255 0.069 Uiso 1 1 calc R . .
C8 C 0.7665(2) 0.25728(11) 0.03047(8) 0.0514(5) Uani 1 1 d . . .
H8 H 0.7612 0.2622 -0.0062 0.062 Uiso 1 1 calc R . .
C9 C 0.8988(2) 0.23138(12) 0.04188(8) 0.0552(5) Uani 1 1 d . . .
C10 C 0.71291(18) 0.18979(9) 0.13844(7) 0.0416(4) Uani 1 1 d . . .
C11 C 0.7264(2) 0.12505(10) 0.15214(8) 0.0505(5) Uani 1 1 d . . .
H11 H 0.6768 0.0930 0.1358 0.061 Uiso 1 1 calc R . .
C12 C 0.8102(3) 0.10646(11) 0.18898(8) 0.0591(6) Uani 1 1 d . . .
H12 H 0.8193 0.0621 0.1976 0.071 Uiso 1 1 calc R . .
C13 C 0.8800(2) 0.15332(12) 0.21292(8) 0.0562(5) Uani 1 1 d . . .
C14 C 0.8676(2) 0.21785(12) 0.20130(9) 0.0585(6) Uani 1 1 d . . .
H14 H 0.9155 0.2497 0.2186 0.070 Uiso 1 1 calc R . .
C15 C 0.7839(2) 0.23570(10) 0.16379(8) 0.0506(5) Uani 1 1 d . . .
H15 H 0.7751 0.2802 0.1554 0.061 Uiso 1 1 calc R . .
C16 C 0.4566(2) 0.27901(10) 0.13999(9) 0.0506(5) Uani 1 1 d . . .
C17 C 0.2400(3) 0.24858(15) 0.15461(15) 0.0905(10) Uani 1 1 d . . .
H17A H 0.2667 0.2438 0.1895 0.109 Uiso 1 1 calc R . .
H17B H 0.1837 0.2116 0.1461 0.109 Uiso 1 1 calc R . .
C18 C 0.1680(3) 0.31062(17) 0.14839(17) 0.1018(12) Uani 1 1 d . . .
H18A H 0.2203 0.3467 0.1605 0.153 Uiso 1 1 calc R . .
H18B H 0.0881 0.3086 0.1672 0.153 Uiso 1 1 calc R . .
H18C H 0.1485 0.3172 0.1134 0.153 Uiso 1 1 calc R . .
C19 C 0.5628(2) 0.39419(10) 0.09056(8) 0.0475(5) Uani 1 1 d . . .
C20 C 0.6582(2) 0.44846(10) 0.09877(9) 0.0546(5) Uani 1 1 d . . .
H20A H 0.7059 0.4555 0.0676 0.066 Uiso 1 1 calc R . .
H20B H 0.6101 0.4887 0.1059 0.066 Uiso 1 1 calc R . .
C21 C 0.7541(2) 0.43790(9) 0.13977(8) 0.0502(5) Uani 1 1 d . . .
C22 C 0.8804(2) 0.45728(12) 0.13382(11) 0.0653(6) Uani 1 1 d . . .
H22 H 0.9070 0.4757 0.1033 0.078 Uiso 1 1 calc R . .
C23 C 0.9676(3) 0.45012(16) 0.17153(15) 0.0844(9) Uani 1 1 d . . .
H23 H 1.0535 0.4640 0.1671 0.101 Uiso 1 1 calc R . .
C24 C 0.9310(3) 0.42318(17) 0.21516(14) 0.0901(10) Uani 1 1 d . . .
H24 H 0.9916 0.4182 0.2410 0.108 Uiso 1 1 calc R . .
C25 C 0.8069(3) 0.40311(16) 0.22196(11) 0.0806(8) Uani 1 1 d . . .
H25 H 0.7817 0.3843 0.2525 0.097 Uiso 1 1 calc R . .
C26 C 0.7184(3) 0.41031(12) 0.18426(9) 0.0606(6) Uani 1 1 d . . .
H26 H 0.6327 0.3962 0.1890 0.073 Uiso 1 1 calc R . .
C27 C 0.4367(2) 0.40380(10) 0.08731(8) 0.0510(5) Uani 1 1 d . . .
H27 H 0.3875 0.3683 0.0755 0.061 Uiso 1 1 calc R . .
C28 C 0.3646(2) 0.46346(10) 0.09998(8) 0.0480(5) Uani 1 1 d . . .
C29 C 0.2729(2) 0.48752(10) 0.06748(8) 0.0486(5) Uani 1 1 d . . .
H29 H 0.2589 0.4669 0.0366 0.058 Uiso 1 1 calc R . .
C30 C 0.2024(2) 0.54151(10) 0.08033(9) 0.0513(5) Uani 1 1 d . . .
C31 C 0.2173(2) 0.57178(11) 0.12511(10) 0.0612(6) Uani 1 1 d . . .
H31 H 0.1672 0.6086 0.1334 0.073 Uiso 1 1 calc R . .
C32 C 0.3061(3) 0.54766(13) 0.15756(10) 0.0705(7) Uani 1 1 d . . .
H32 H 0.3173 0.5678 0.1888 0.085 Uiso 1 1 calc R . .
C33 C 0.3800(3) 0.49405(12) 0.14525(9) 0.0624(6) Uani 1 1 d . . .
H33 H 0.4416 0.4782 0.1680 0.075 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.902(2) . ?
Cl1 C30 1.742(2) . ?
O1 C2 1.210(3) . ?
O2 C9 1.207(3) . ?
O3 C16 1.194(3) . ?
O4 C16 1.340(3) . ?
O4 C17 1.469(3) . ?
N1 C2 1.381(3) . ?
N1 C9 1.383(3) . ?
N1 C1 1.457(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.510(3) . ?
C3 C8 1.530(3) . ?
C3 C4 1.554(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.520(3) . ?
C4 C10 1.528(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.337(3) . ?
C5 C16 1.506(3) . ?
C6 C19 1.493(3) . ?
C6 C7 1.509(3) . ?
C7 C8 1.529(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.514(3) . ?
C8 H8 1.0000 . ?
C10 C15 1.385(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C18 1.494(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C27 1.335(3) . ?
C19 C20 1.516(3) . ?
C20 C21 1.511(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C26 1.384(3) . ?
C21 C22 1.389(3) . ?
C22 C23 1.376(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.361(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.483(3) . ?
C27 H27 0.9500 . ?
C28 C33 1.388(3) . ?
C28 C29 1.393(3) . ?
C29 C30 1.380(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.373(3) . ?
C31 C32 1.372(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.389(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O4 C17 115.9(2) . . ?
C2 N1 C9 112.86(18) . . ?
C2 N1 C1 123.0(2) . . ?
C9 N1 C1 123.9(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 123.9(2) . . ?
O1 C2 C3 128.4(2) . . ?
N1 C2 C3 107.69(19) . . ?
C2 C3 C8 103.56(18) . . ?
C2 C3 C4 110.35(17) . . ?
C8 C3 C4 113.26(16) . . ?
C2 C3 H3 109.8 . . ?
C8 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C5 C4 C10 111.72(16) . . ?
C5 C4 C3 109.75(17) . . ?
C10 C4 C3 113.79(16) . . ?
C5 C4 H4 107.1 . . ?
C10 C4 H4 107.1 . . ?
C3 C4 H4 107.1 . . ?
C6 C5 C16 122.31(18) . . ?
C6 C5 C4 123.18(19) . . ?
C16 C5 C4 114.23(17) . . ?
C5 C6 C19 122.38(19) . . ?
C5 C6 C7 121.19(18) . . ?
C19 C6 C7 116.33(18) . . ?
C6 C7 C8 115.32(19) . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 114.5(2) . . ?
C9 C8 C3 103.27(17) . . ?
C7 C8 C3 117.92(18) . . ?
C9 C8 H8 106.8 . . ?
C7 C8 H8 106.8 . . ?
C3 C8 H8 106.8 . . ?
O2 C9 N1 124.5(2) . . ?
O2 C9 C8 128.1(2) . . ?
N1 C9 C8 107.4(2) . . ?
C15 C10 C11 118.0(2) . . ?
C15 C10 C4 122.71(17) . . ?
C11 C10 C4 119.27(18) . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 Br1 119.84(18) . . ?
C14 C13 Br1 118.60(19) . . ?
C13 C14 C15 118.9(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 121.2(2) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
O3 C16 O4 124.2(2) . . ?
O3 C16 C5 125.1(2) . . ?
O4 C16 C5 110.7(2) . . ?
O4 C17 C18 110.4(3) . . ?
O4 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
O4 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C27 C19 C6 120.0(2) . . ?
C27 C19 C20 123.31(19) . . ?
C6 C19 C20 116.63(19) . . ?
C21 C20 C19 115.93(17) . . ?
C21 C20 H20A 108.3 . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
C19 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C26 C21 C22 118.4(2) . . ?
C26 C21 C20 121.4(2) . . ?
C22 C21 C20 120.2(2) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 120.4(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C19 C27 C28 127.5(2) . . ?
C19 C27 H27 116.2 . . ?
C28 C27 H27 116.2 . . ?
C33 C28 C29 118.4(2) . . ?
C33 C28 C27 121.5(2) . . ?
C29 C28 C27 119.93(19) . . ?
C30 C29 C28 119.7(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 122.0(2) . . ?
C31 C30 Cl1 119.16(17) . . ?
C29 C30 Cl1 118.84(18) . . ?
C32 C31 C30 118.5(2) . . ?
C32 C31 H31 120.7 . . ?
C30 C31 H31 120.7 . . ?
C31 C32 C33 120.7(2) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C28 C33 C32 120.6(2) . . ?
C28 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?

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
C9 N1 C2 O1 176.6(2) . . . . ?
C1 N1 C2 O1 -9.5(4) . . . . ?
C9 N1 C2 C3 -5.6(2) . . . . ?
C1 N1 C2 C3 168.4(2) . . . . ?
O1 C2 C3 C8 -164.4(2) . . . . ?
N1 C2 C3 C8 17.8(2) . . . . ?
O1 C2 C3 C4 74.1(3) . . . . ?
N1 C2 C3 C4 -103.7(2) . . . . ?
C2 C3 C4 C5 163.72(17) . . . . ?
C8 C3 C4 C5 48.1(2) . . . . ?
C2 C3 C4 C10 37.7(2) . . . . ?
C8 C3 C4 C10 -77.9(2) . . . . ?
C10 C4 C5 C6 93.5(2) . . . . ?
C3 C4 C5 C6 -33.6(3) . . . . ?
C10 C4 C5 C16 -80.5(2) . . . . ?
C3 C4 C5 C16 152.33(18) . . . . ?
C16 C5 C6 C19 -5.5(3) . . . . ?
C4 C5 C6 C19 -179.03(19) . . . . ?
C16 C5 C6 C7 170.7(2) . . . . ?
C4 C5 C6 C7 -2.8(3) . . . . ?
C5 C6 C7 C8 23.6(3) . . . . ?
C19 C6 C7 C8 -159.95(19) . . . . ?
C6 C7 C8 C9 -127.3(2) . . . . ?
C6 C7 C8 C3 -5.4(3) . . . . ?
C2 C3 C8 C9 -22.4(2) . . . . ?
C4 C3 C8 C9 97.17(19) . . . . ?
C2 C3 C8 C7 -149.76(19) . . . . ?
C4 C3 C8 C7 -30.2(3) . . . . ?
C2 N1 C9 O2 172.6(2) . . . . ?
C1 N1 C9 O2 -1.4(4) . . . . ?
C2 N1 C9 C8 -9.6(2) . . . . ?
C1 N1 C9 C8 176.5(2) . . . . ?
C7 C8 C9 O2 -32.6(3) . . . . ?
C3 C8 C9 O2 -162.1(2) . . . . ?
C7 C8 C9 N1 149.57(19) . . . . ?
C3 C8 C9 N1 20.1(2) . . . . ?
C5 C4 C10 C15 -28.5(3) . . . . ?
C3 C4 C10 C15 96.4(2) . . . . ?
C5 C4 C10 C11 150.59(19) . . . . ?
C3 C4 C10 C11 -84.4(2) . . . . ?
C15 C10 C11 C12 -1.7(3) . . . . ?
C4 C10 C11 C12 179.16(19) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C11 C12 C13 Br1 179.71(17) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
Br1 C13 C14 C15 179.62(17) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
C4 C10 C15 C14 -179.9(2) . . . . ?
C13 C14 C15 C10 0.4(4) . . . . ?
C17 O4 C16 O3 2.7(4) . . . . ?
C17 O4 C16 C5 -179.6(2) . . . . ?
C6 C5 C16 O3 -64.0(3) . . . . ?
C4 C5 C16 O3 110.1(2) . . . . ?
C6 C5 C16 O4 118.3(2) . . . . ?
C4 C5 C16 O4 -67.6(2) . . . . ?
C16 O4 C17 C18 82.0(3) . . . . ?
C5 C6 C19 C27 -45.4(3) . . . . ?
C7 C6 C19 C27 138.2(2) . . . . ?
C5 C6 C19 C20 138.2(2) . . . . ?
C7 C6 C19 C20 -38.2(3) . . . . ?
C27 C19 C20 C21 130.0(2) . . . . ?
C6 C19 C20 C21 -53.7(3) . . . . ?
C19 C20 C21 C26 -40.8(3) . . . . ?
C19 C20 C21 C22 140.7(2) . . . . ?
C26 C21 C22 C23 -1.0(4) . . . . ?
C20 C21 C22 C23 177.6(2) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C23 C24 C25 C26 0.0(5) . . . . ?
C22 C21 C26 C25 0.8(4) . . . . ?
C20 C21 C26 C25 -177.8(2) . . . . ?
C24 C25 C26 C21 -0.3(4) . . . . ?
C6 C19 C27 C28 171.4(2) . . . . ?
C20 C19 C27 C28 -12.4(4) . . . . ?
C19 C27 C28 C33 -51.2(4) . . . . ?
C19 C27 C28 C29 133.1(2) . . . . ?
C33 C28 C29 C30 1.6(3) . . . . ?
C27 C28 C29 C30 177.4(2) . . . . ?
C28 C29 C30 C31 -1.7(3) . . . . ?
C28 C29 C30 Cl1 -179.70(17) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
Cl1 C30 C31 C32 178.7(2) . . . . ?
C30 C31 C32 C33 0.4(4) . . . . ?
C29 C28 C33 C32 -0.5(4) . . . . ?
C27 C28 C33 C32 -176.2(2) . . . . ?
C31 C32 C33 C28 -0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        72.13
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.750
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_skg2_4
_database_code_depnum_ccdc_archive 'CCDC 1427914'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;
_audit_creation_date             2015-09-16
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C34 H32 Br N O5'
_chemical_formula_sum            'C34 H32 Br N O5'
_chemical_formula_weight         614.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C34 H32 Br N O5'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   13.0988(11)
_cell_length_b                   27.6314(14)
_cell_length_c                   8.4212(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.631(7)
_cell_angle_gamma                90
_cell_volume                     3041.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2699
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.4150
_cell_measurement_theta_min      3.1930
_exptl_absorpt_coefficient_mu    2.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10305
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.246
_diffrn_reflns_theta_min         3.199
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 8.3200
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9768
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega   36.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega  -63.00   38.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -      -54.7289   30.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  4 omega -110.00  -81.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega -114.00  -80.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega  123.00  157.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       54.7289  126.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega  -36.00  101.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       54.7289  -77.0000 -180.0000 137

#__ type_ start__ end____ width___ exp.time_
  8 omega   12.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
  9 omega   13.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -64.0000   60.0000 121

#__ type_ start__ end____ width___ exp.time_
 10 omega   18.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
 11 omega   21.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 12 omega   17.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
 13 omega   70.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega  118.00  148.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   64.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   18.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   10.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000   90.0000 57
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0249670000
_diffrn_orient_matrix_UB_12      -0.0116738000
_diffrn_orient_matrix_UB_13      0.1772162000
_diffrn_orient_matrix_UB_21      0.1151240000
_diffrn_orient_matrix_UB_22      0.0044193000
_diffrn_orient_matrix_UB_23      -0.0250429000
_diffrn_orient_matrix_UB_31      -0.0041270000
_diffrn_orient_matrix_UB_32      0.0543004000
_diffrn_orient_matrix_UB_33      0.0400193000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3268
_reflns_number_total             5660
_reflns_odcompleteness_completeness 99.69
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5660
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0787
_refine_ls_restrained_S_all      1.049
_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)+(0.1398P)²+0.3552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2820
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C10(H10A,H10B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C5(H5), C29(H29), C26(H26), C30(H30), C3(H3), C6(H6), C33(H33),
 C22(H22), C32(H32), C25(H25), C23(H23), C24(H24), C2(H2)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br1 Br 0.10660(10) 0.74032(3) 0.09935(11) 0.1666(6) Uani 1 1 d . . . . .
O4 O 0.2081(3) 0.48684(14) -0.1150(4) 0.0982(10) Uani 1 1 d . . . . .
O1 O 0.5769(3) 0.65620(17) -0.0006(5) 0.1174(14) Uani 1 1 d . . . . .
O5 O 0.1985(3) 0.26897(12) -0.6651(4) 0.1020(11) Uani 1 1 d . . . . .
O2 O 0.4035(4) 0.67850(17) -0.4781(5) 0.1305(16) Uani 1 1 d . . . . .
C12 C 0.3475(4) 0.53678(15) -0.1721(5) 0.0758(11) Uani 1 1 d . . . . .
C7 C 0.4040(4) 0.57832(18) -0.0849(5) 0.0833(12) Uani 1 1 d . . . . .
H7 H 0.4342 0.5648 0.0150 0.100 Uiso 1 1 calc R U . . .
O3 O 0.3363(3) 0.49222(14) 0.0679(4) 0.1054(11) Uani 1 1 d . . . . .
C27 C 0.3270(3) 0.44740(18) -0.3910(5) 0.0812(12) Uani 1 1 d . . . . .
H27 H 0.3786 0.4452 -0.3103 0.097 Uiso 1 1 calc R U . . .
C4 C 0.3297(4) 0.61702(18) -0.0392(5) 0.0823(12) Uani 1 1 d . . . . .
N1 N 0.4936(3) 0.67851(16) -0.2358(5) 0.0922(12) Uani 1 1 d . . . . .
C19 C 0.2925(3) 0.49185(17) -0.4225(5) 0.0765(11) Uani 1 1 d . . . . .
C5 C 0.2444(4) 0.62968(18) -0.1361(6) 0.0926(14) Uani 1 1 d . . . . .
H5 H 0.2307 0.6131 -0.2313 0.111 Uiso 1 1 calc R U . . .
C16 C 0.2985(4) 0.50295(16) -0.0632(5) 0.0800(11) Uani 1 1 d . . . . .
C29 C 0.2657(4) 0.39562(17) -0.6279(5) 0.0802(11) Uani 1 1 d . . . . .
H29 H 0.2669 0.4223 -0.6951 0.096 Uiso 1 1 calc R U . . .
C28 C 0.2950(3) 0.40113(16) -0.4656(5) 0.0760(11) Uani 1 1 d . . . . .
C26 C 0.0785(4) 0.54725(19) -0.4029(6) 0.0880(13) Uani 1 1 d . . . . .
H26 H 0.0773 0.5206 -0.3354 0.106 Uiso 1 1 calc R U . . .
C8 C 0.4934(4) 0.59632(19) -0.1781(5) 0.0849(12) Uani 1 1 d . . . . .
H8 H 0.5503 0.5734 -0.1645 0.102 Uiso 1 1 calc R U . . .
C21 C 0.1437(3) 0.54715(16) -0.5274(6) 0.0801(11) Uani 1 1 d . . . . .
C31 C 0.2338(4) 0.31107(17) -0.5938(5) 0.0822(12) Uani 1 1 d . . . . .
C30 C 0.2355(4) 0.35151(16) -0.6890(5) 0.0820(12) Uani 1 1 d . . . . .
H30 H 0.2157 0.3489 -0.7967 0.098 Uiso 1 1 calc R U . . .
C3 C 0.3463(4) 0.6425(2) 0.1055(6) 0.0961(15) Uani 1 1 d . . . . .
H3 H 0.4021 0.6344 0.1742 0.115 Uiso 1 1 calc R U . . .
C6 C 0.1795(5) 0.6661(2) -0.0951(6) 0.1050(17) Uani 1 1 d . . . . .
H6 H 0.1232 0.6740 -0.1628 0.126 Uiso 1 1 calc R U . . .
C33 C 0.2989(4) 0.35922(18) -0.3749(5) 0.0880(13) Uani 1 1 d . . . . .
H33 H 0.3232 0.3613 -0.2690 0.106 Uiso 1 1 calc R U . . .
C11 C 0.3398(3) 0.53366(17) -0.3308(5) 0.0796(11) Uani 1 1 d . . . . .
C22 C 0.1430(4) 0.5869(2) -0.6233(7) 0.1018(16) Uani 1 1 d . . . . .
H22 H 0.1857 0.5879 -0.7074 0.122 Uiso 1 1 calc R U . . .
C32 C 0.2688(4) 0.31505(17) -0.4340(5) 0.0877(13) Uani 1 1 d . . . . .
H32 H 0.2716 0.2879 -0.3685 0.105 Uiso 1 1 calc R U . . .
C20 C 0.2121(4) 0.50394(17) -0.5556(5) 0.0815(12) Uani 1 1 d . . . . .
H20A H 0.2469 0.5098 -0.6520 0.098 Uiso 1 1 calc R U . . .
H20B H 0.1689 0.4758 -0.5743 0.098 Uiso 1 1 calc R U . . .
C1 C 0.1976(5) 0.6907(2) 0.0451(6) 0.1038(16) Uani 1 1 d . . . . .
C10 C 0.3830(4) 0.5718(2) -0.4343(6) 0.1004(16) Uani 1 1 d . . . . .
H10A H 0.3272 0.5924 -0.4746 0.121 Uiso 1 1 calc R U . . .
H10B H 0.4104 0.5559 -0.5251 0.121 Uiso 1 1 calc R U . . .
C9 C 0.4657(4) 0.60372(19) -0.3573(5) 0.0836(12) Uani 1 1 d . . . . .
H9 H 0.5280 0.5970 -0.4120 0.100 Uiso 1 1 calc R U . . .
C25 C 0.0169(4) 0.5857(2) -0.3788(7) 0.0994(15) Uani 1 1 d . . . . .
H25 H -0.0260 0.5848 -0.2950 0.119 Uiso 1 1 calc R U . . .
C34 C 0.1889(5) 0.2278(2) -0.5680(7) 0.1113(18) Uani 1 1 d . . . . .
H34A H 0.1585 0.2019 -0.6304 0.167 Uiso 1 1 calc R U . . .
H34B H 0.1463 0.2355 -0.4828 0.167 Uiso 1 1 calc R U . . .
H34C H 0.2553 0.2181 -0.5247 0.167 Uiso 1 1 calc R U . . .
C13 C 0.5290(4) 0.6453(2) -0.1243(6) 0.0914(14) Uani 1 1 d . . . . .
C23 C 0.0800(5) 0.6260(2) -0.5976(9) 0.122(2) Uani 1 1 d . . . . .
H23 H 0.0808 0.6528 -0.6643 0.147 Uiso 1 1 calc R U . . .
C24 C 0.0163(5) 0.6254(2) -0.4740(9) 0.1142(19) Uani 1 1 d . . . . .
H24 H -0.0261 0.6516 -0.4559 0.137 Uiso 1 1 calc R U . . .
C14 C 0.4477(4) 0.6562(2) -0.3707(6) 0.0952(15) Uani 1 1 d . . . . .
C2 C 0.2817(5) 0.6788(2) 0.1467(7) 0.1119(18) Uani 1 1 d . . . . .
H2 H 0.2940 0.6954 0.2421 0.134 Uiso 1 1 calc R U . . .
C17 C 0.1617(6) 0.4504(3) -0.0206(8) 0.142(3) Uani 1 1 d . . . . .
H17A H 0.2135 0.4274 0.0176 0.170 Uiso 1 1 calc R U . . .
H17B H 0.1339 0.4655 0.0712 0.170 Uiso 1 1 calc R U . . .
C15 C 0.5028(6) 0.7307(2) -0.2156(9) 0.132(2) Uani 1 1 d . . . . .
H15A H 0.4456 0.7426 -0.1613 0.197 Uiso 1 1 calc R U . . .
H15B H 0.5037 0.7459 -0.3181 0.197 Uiso 1 1 calc R U . . .
H15C H 0.5651 0.7380 -0.1543 0.197 Uiso 1 1 calc R U . . .
C18 C 0.0873(9) 0.4270(4) -0.1042(12) 0.212(5) Uani 1 1 d . . . . .
H18A H 0.1089 0.4199 -0.2085 0.317 Uiso 1 1 calc R U . . .
H18B H 0.0271 0.4469 -0.1132 0.317 Uiso 1 1 calc R U . . .
H18C H 0.0722 0.3973 -0.0511 0.317 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.892(6) . ?
O4 C16 1.313(5) . ?
O4 C17 1.442(7) . ?
O1 C13 1.220(6) . ?
O5 C31 1.375(6) . ?
O5 C34 1.410(7) . ?
O2 C14 1.210(6) . ?
C12 C7 1.528(6) . ?
C12 C16 1.483(6) . ?
C12 C11 1.337(6) . ?
C7 C4 1.512(7) . ?
C7 C8 1.534(7) . ?
O3 C16 1.218(5) . ?
C27 C19 1.330(6) . ?
C27 C28 1.474(6) . ?
C4 C5 1.386(6) . ?
C4 C3 1.412(6) . ?
N1 C13 1.372(6) . ?
N1 C14 1.394(6) . ?
N1 C15 1.456(8) . ?
C19 C11 1.502(6) . ?
C19 C20 1.525(5) . ?
C5 C6 1.375(8) . ?
C29 C28 1.404(6) . ?
C29 C30 1.372(6) . ?
C28 C33 1.386(6) . ?
C26 C21 1.393(7) . ?
C26 C25 1.357(7) . ?
C8 C9 1.543(6) . ?
C8 C13 1.493(7) . ?
C21 C22 1.364(7) . ?
C21 C20 1.521(6) . ?
C31 C30 1.376(6) . ?
C31 C32 1.399(6) . ?
C3 C2 1.371(9) . ?
C6 C1 1.370(7) . ?
C33 C32 1.367(7) . ?
C11 C10 1.501(7) . ?
C22 C23 1.384(8) . ?
C1 C2 1.391(8) . ?
C10 C9 1.511(6) . ?
C9 C14 1.473(8) . ?
C25 C24 1.359(8) . ?
C23 C24 1.375(9) . ?
C17 C18 1.333(10) . ?

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
C16 O4 C17 117.2(4) . . ?
C31 O5 C34 118.0(4) . . ?
C16 C12 C7 113.1(3) . . ?
C11 C12 C7 122.2(4) . . ?
C11 C12 C16 124.7(4) . . ?
C12 C7 C8 111.1(4) . . ?
C4 C7 C12 110.7(4) . . ?
C4 C7 C8 115.2(4) . . ?
C19 C27 C28 129.2(4) . . ?
C5 C4 C7 122.4(4) . . ?
C5 C4 C3 117.2(5) . . ?
C3 C4 C7 120.3(4) . . ?
C13 N1 C14 111.9(4) . . ?
C13 N1 C15 124.0(5) . . ?
C14 N1 C15 124.1(5) . . ?
C27 C19 C11 118.9(4) . . ?
C27 C19 C20 124.0(4) . . ?
C11 C19 C20 116.9(4) . . ?
C6 C5 C4 121.7(5) . . ?
O4 C16 C12 115.1(4) . . ?
O3 C16 O4 121.7(5) . . ?
O3 C16 C12 123.1(4) . . ?
C30 C29 C28 121.1(4) . . ?
C29 C28 C27 124.2(4) . . ?
C33 C28 C27 119.3(4) . . ?
C33 C28 C29 116.4(4) . . ?
C25 C26 C21 120.8(5) . . ?
C7 C8 C9 113.8(4) . . ?
C13 C8 C7 111.9(4) . . ?
C13 C8 C9 103.1(4) . . ?
C26 C21 C20 120.9(4) . . ?
C22 C21 C26 117.6(5) . . ?
C22 C21 C20 121.5(5) . . ?
O5 C31 C30 116.7(4) . . ?
O5 C31 C32 124.5(4) . . ?
C30 C31 C32 118.7(4) . . ?
C29 C30 C31 121.2(4) . . ?
C2 C3 C4 121.3(5) . . ?
C1 C6 C5 120.2(5) . . ?
C32 C33 C28 123.1(4) . . ?
C12 C11 C19 124.5(4) . . ?
C12 C11 C10 121.9(4) . . ?
C10 C11 C19 113.5(4) . . ?
C21 C22 C23 121.2(6) . . ?
C33 C32 C31 119.3(4) . . ?
C21 C20 C19 116.4(4) . . ?
C6 C1 Br1 119.4(5) . . ?
C6 C1 C2 120.0(6) . . ?
C2 C1 Br1 120.6(4) . . ?
C11 C10 C9 116.5(4) . . ?
C10 C9 C8 117.4(4) . . ?
C14 C9 C8 103.4(4) . . ?
C14 C9 C10 115.8(4) . . ?
C26 C25 C24 121.7(6) . . ?
O1 C13 N1 123.6(5) . . ?
O1 C13 C8 128.1(5) . . ?
N1 C13 C8 108.2(4) . . ?
C24 C23 C22 120.3(6) . . ?
C25 C24 C23 118.4(6) . . ?
O2 C14 N1 123.0(5) . . ?
O2 C14 C9 128.7(5) . . ?
N1 C14 C9 108.3(4) . . ?
C3 C2 C1 119.6(5) . . ?
C18 C17 O4 111.6(6) . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rekha3_2
_database_code_depnum_ccdc_archive 'CCDC 1427915'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;
_audit_creation_date             2015-09-16
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H27 N O4'
_chemical_formula_sum            'C26 H27 N O4'
_chemical_formula_weight         417.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H27 N O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   14.7213(14)
_cell_length_b                   12.0482(10)
_cell_length_c                   13.0935(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.305(11)
_cell_angle_gamma                90
_cell_volume                     2191.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2518
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0010
_cell_measurement_theta_min      3.6710
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7718
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.164
_diffrn_reflns_theta_min         3.181
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3200
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.7006
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00  -46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -78.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega -154.00 -127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega -149.00  -98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
  6 omega  -46.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289  -77.0000   30.0000 130

#__ type_ start__ end____ width___ exp.time_
  7 omega  -45.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289  -30.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
  8 omega   59.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   77.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  9 omega   48.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   11.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega  104.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  178.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 13 omega    7.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 14 omega   80.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   64.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 15 omega    9.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -50.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   61.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   64.0000 -150.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1017423000
_diffrn_orient_matrix_UB_12      -0.0415235000
_diffrn_orient_matrix_UB_13      -0.0645515000
_diffrn_orient_matrix_UB_21      0.0184378000
_diffrn_orient_matrix_UB_22      -0.1070909000
_diffrn_orient_matrix_UB_23      0.0681059000
_diffrn_orient_matrix_UB_31      -0.0398959000
_diffrn_orient_matrix_UB_32      0.0563600000
_diffrn_orient_matrix_UB_33      0.0817629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2835
_reflns_number_total             4085
_reflns_odcompleteness_completeness 99.54
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0880P)²+0.2578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1723
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C3(H3), C7(H7), C22(H22), C6(H6), C4(H4A), C23(H23), C26(H26),
 C25(H25), C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O4 O 0.51256(15) 0.7174(2) 0.10084(18) 0.1007(8) Uani 1 1 d . . . . .
H4 H 0.4543 0.7276 0.0830 0.151 Uiso 1 1 calc R U . . .
N1 N 0.17150(14) 0.72964(17) 0.34799(16) 0.0557(5) Uani 1 1 d . . . . .
O1 O 0.21109(12) 0.25132(15) 0.52521(15) 0.0679(5) Uani 1 1 d . . . . .
C18 C 0.53214(15) 0.60572(18) 0.25972(17) 0.0475(5) Uani 1 1 d . . . . .
O3 O 0.30389(13) 0.76346(17) 0.49500(14) 0.0752(6) Uani 1 1 d . . . . .
O2 O 0.06831(12) 0.68067(17) 0.18178(15) 0.0738(5) Uani 1 1 d . . . . .
C13 C 0.24232(15) 0.67242(18) 0.22150(17) 0.0486(5) Uani 1 1 d . . . . .
H13 H 0.2404 0.7118 0.1553 0.058 Uiso 1 1 calc R U . . .
C9 C 0.36247(15) 0.54105(18) 0.19839(16) 0.0463(5) Uani 1 1 d . . . . .
C10 C 0.43395(15) 0.59860(19) 0.26758(17) 0.0480(5) Uani 1 1 d . . . . .
C8 C 0.26248(14) 0.54689(18) 0.20793(16) 0.0457(5) Uani 1 1 d . . . . .
H8 H 0.2171 0.5234 0.1380 0.055 Uiso 1 1 calc R U . . .
C2 C 0.21721(16) 0.32283(18) 0.44619(18) 0.0513(5) Uani 1 1 d . . . . .
C20 C 0.59664(16) 0.52457(19) 0.29407(18) 0.0505(5) Uani 1 1 d . . . . .
H20 H 0.5776 0.4641 0.3263 0.061 Uiso 1 1 calc R U . . .
C21 C 0.69454(16) 0.51908(18) 0.28706(18) 0.0511(5) Uani 1 1 d . . . . .
C3 C 0.30874(16) 0.34519(19) 0.44613(18) 0.0539(6) Uani 1 1 d . . . . .
H3 H 0.3611 0.3114 0.4971 0.065 Uiso 1 1 calc R U . . .
C12 C 0.31911(15) 0.72623(18) 0.31756(17) 0.0479(5) Uani 1 1 d . . . . .
H12 H 0.3309 0.8005 0.2941 0.057 Uiso 1 1 calc R U . . .
C7 C 0.13982(17) 0.3705(2) 0.36873(19) 0.0558(6) Uani 1 1 d . . . . .
H7 H 0.0774 0.3551 0.3670 0.067 Uiso 1 1 calc R U . . .
C22 C 0.76806(17) 0.4696(2) 0.3698(2) 0.0603(6) Uani 1 1 d . . . . .
H22 H 0.7550 0.4403 0.4292 0.072 Uiso 1 1 calc R U . . .
C16 C 0.14945(16) 0.69341(19) 0.2428(2) 0.0542(6) Uani 1 1 d . . . . .
C6 C 0.15577(15) 0.4418(2) 0.29321(18) 0.0513(5) Uani 1 1 d . . . . .
H6 H 0.1030 0.4723 0.2402 0.062 Uiso 1 1 calc R U . . .
C4 C 0.32390(15) 0.41702(19) 0.37154(18) 0.0507(5) Uani 1 1 d . . . . .
H4A H 0.3865 0.4310 0.3732 0.061 Uiso 1 1 calc R U . . .
C11 C 0.41584(15) 0.6672(2) 0.35641(18) 0.0527(6) Uani 1 1 d . . . . .
H11A H 0.4666 0.7219 0.3824 0.063 Uiso 1 1 calc R U . . .
H11B H 0.4181 0.6190 0.4165 0.063 Uiso 1 1 calc R U . . .
C14 C 0.26882(16) 0.74192(19) 0.39985(19) 0.0527(5) Uani 1 1 d . . . . .
C5 C 0.24759(15) 0.46926(17) 0.29366(16) 0.0449(5) Uani 1 1 d . . . . .
C23 C 0.8607(2) 0.4632(2) 0.3653(3) 0.0744(8) Uani 1 1 d . . . . .
H23 H 0.9093 0.4304 0.4218 0.089 Uiso 1 1 calc R U . . .
C1 C 0.1216(2) 0.2390(3) 0.5414(2) 0.0751(8) Uani 1 1 d . . . . .
H1A H 0.0781 0.1996 0.4813 0.113 Uiso 1 1 calc R U . . .
H1B H 0.0956 0.3109 0.5470 0.113 Uiso 1 1 calc R U . . .
H1C H 0.1303 0.1981 0.6068 0.113 Uiso 1 1 calc R U . . .
C26 C 0.71587(18) 0.5584(2) 0.1978(2) 0.0634(7) Uani 1 1 d . . . . .
H26 H 0.6673 0.5894 0.1401 0.076 Uiso 1 1 calc R U . . .
C15 C 0.0975(2) 0.7533(3) 0.3972(3) 0.0815(9) Uani 1 1 d . . . . .
H15A H 0.0956 0.8317 0.4095 0.122 Uiso 1 1 calc R U . . .
H15B H 0.1125 0.7146 0.4648 0.122 Uiso 1 1 calc R U . . .
H15C H 0.0360 0.7292 0.3494 0.122 Uiso 1 1 calc R U . . .
C25 C 0.8091(2) 0.5521(3) 0.1938(2) 0.0738(8) Uani 1 1 d . . . . .
H25 H 0.8225 0.5800 0.1341 0.089 Uiso 1 1 calc R U . . .
C17 C 0.37140(17) 0.4725(2) 0.10710(19) 0.0589(6) Uani 1 1 d . . . . .
H17A H 0.3315 0.5033 0.0396 0.088 Uiso 1 1 calc R U . . .
H17B H 0.3512 0.3978 0.1138 0.088 Uiso 1 1 calc R U . . .
H17C H 0.4372 0.4722 0.1093 0.088 Uiso 1 1 calc R U . . .
C19 C 0.55154(18) 0.7134(2) 0.2131(2) 0.0668(7) Uani 1 1 d . . . . .
H19A H 0.5250 0.7738 0.2433 0.080 Uiso 1 1 calc R U . . .
H19B H 0.6206 0.7246 0.2343 0.080 Uiso 1 1 calc R U . . .
C24 C 0.8810(2) 0.5052(2) 0.2771(3) 0.0765(8) Uani 1 1 d . . . . .
H24 H 0.9433 0.5017 0.2745 0.092 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C19 1.390(3) . ?
N1 C16 1.377(3) . ?
N1 C14 1.376(3) . ?
N1 C15 1.465(3) . ?
O1 C2 1.372(3) . ?
O1 C1 1.409(3) . ?
C18 C10 1.485(3) . ?
C18 C20 1.333(3) . ?
C18 C19 1.502(3) . ?
O3 C14 1.209(3) . ?
O2 C16 1.207(3) . ?
C13 C8 1.563(3) . ?
C13 C12 1.530(3) . ?
C13 C16 1.504(3) . ?
C9 C10 1.334(3) . ?
C9 C8 1.519(3) . ?
C9 C17 1.494(3) . ?
C10 C11 1.521(3) . ?
C8 C5 1.532(3) . ?
C2 C3 1.374(3) . ?
C2 C7 1.376(3) . ?
C20 C21 1.476(3) . ?
C21 C22 1.388(3) . ?
C21 C26 1.389(3) . ?
C3 C4 1.377(3) . ?
C12 C11 1.521(3) . ?
C12 C14 1.507(3) . ?
C7 C6 1.387(3) . ?
C22 C23 1.387(3) . ?
C6 C5 1.390(3) . ?
C4 C5 1.393(3) . ?
C23 C24 1.381(4) . ?
C26 C25 1.393(3) . ?
C25 C24 1.366(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C15 122.5(2) . . ?
C14 N1 C16 113.0(2) . . ?
C14 N1 C15 124.5(2) . . ?
C2 O1 C1 118.48(19) . . ?
C10 C18 C19 113.48(19) . . ?
C20 C18 C10 122.4(2) . . ?
C20 C18 C19 124.1(2) . . ?
C12 C13 C8 112.78(17) . . ?
C16 C13 C8 113.72(18) . . ?
C16 C13 C12 104.25(18) . . ?
C10 C9 C8 119.24(18) . . ?
C10 C9 C17 124.9(2) . . ?
C17 C9 C8 115.80(18) . . ?
C18 C10 C11 116.26(18) . . ?
C9 C10 C18 123.40(19) . . ?
C9 C10 C11 120.24(19) . . ?
C9 C8 C13 106.25(17) . . ?
C9 C8 C5 114.16(17) . . ?
C5 C8 C13 115.41(17) . . ?
O1 C2 C3 115.6(2) . . ?
O1 C2 C7 125.0(2) . . ?
C3 C2 C7 119.4(2) . . ?
C18 C20 C21 127.8(2) . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 C26 117.9(2) . . ?
C26 C21 C20 122.3(2) . . ?
C2 C3 C4 120.8(2) . . ?
C11 C12 C13 115.62(18) . . ?
C14 C12 C13 103.70(18) . . ?
C14 C12 C11 116.52(19) . . ?
C2 C7 C6 119.3(2) . . ?
C23 C22 C21 121.0(2) . . ?
N1 C16 C13 108.08(19) . . ?
O2 C16 N1 123.8(2) . . ?
O2 C16 C13 128.1(2) . . ?
C7 C6 C5 122.6(2) . . ?
C3 C4 C5 121.5(2) . . ?
C10 C11 C12 112.33(18) . . ?
N1 C14 C12 108.1(2) . . ?
O3 C14 N1 123.5(2) . . ?
O3 C14 C12 128.3(2) . . ?
C6 C5 C8 121.14(19) . . ?
C6 C5 C4 116.3(2) . . ?
C4 C5 C8 122.43(18) . . ?
C24 C23 C22 120.2(3) . . ?
C21 C26 C25 120.8(2) . . ?
C24 C25 C26 120.3(3) . . ?
O4 C19 C18 113.1(2) . . ?
C25 C24 C23 119.7(3) . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
