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

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

data_Steroidal_compass_11
_database_code_depnum_ccdc_archive 'CCDC 1525776'
_audit_update_record             
;
2017-01-05 deposited with the CCDC.
2017-03-01 downloaded from the CCDC.
;
#============================================================================

_audit_creation_date             2016-11-10T18:07:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2,5-Bis(17alpha-ethynyl-5delta-androst-2-en-17beta-ol)-4-nitroaniline
;
_chemical_melting_point          483
_chemical_formula_moiety         'C48 H62 N2 O4'
_chemical_formula_sum            'C24 H31 N O2'
_chemical_formula_weight         365.50
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_cell_length_a                   39.169(8)
_cell_length_b                   7.5511(15)
_cell_length_c                   16.702(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.27(3)
_cell_angle_gamma                90
_cell_volume                     4918.9(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    33563
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_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'

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

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Needles
_exptl_crystal_colour            Yellow
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.987
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.963
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.023747
_diffrn_orient_matrix_ub_12      -0.004474
_diffrn_orient_matrix_ub_13      -0.017234
_diffrn_orient_matrix_ub_21      0.009559
_diffrn_orient_matrix_ub_22      -0.000887
_diffrn_orient_matrix_ub_23      0.057574
_diffrn_orient_matrix_ub_31      -0.000868
_diffrn_orient_matrix_ub_32      -0.132249
_diffrn_orient_matrix_ub_33      0.000197
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_number            27259
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.615
_diffrn_reflns_theta_max         27.641
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.97
_reflns_Friedel_fraction_full    0.98
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_coverage         0.87
_reflns_number_total             10522
_reflns_number_gt                5624
_reflns_threshold_expression     'I > 2σ(I)'
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
'Refined as a 2-component inversion twin., Twin,SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1601P)²+0.2279P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.019(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_number_reflns         10522
_refine_ls_number_parameters     497
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.1544
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.2703
_refine_ls_wR_factor_gt          0.2242
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2802(3) 0.397(4) 0.6386(11) 0.292(9) Uani 1 1 d . U . . .
H1A H 0.2912 0.4647 0.5987 0.351 Uiso 1 1 calc R U . . .
H1B H 0.2839 0.2729 0.6279 0.351 Uiso 1 1 calc R U . . .
C1A C 0.33449(16) 1.4799(10) 0.1583(5) 0.117(2) Uani 1 1 d . . . . .
H1AA H 0.3371 1.4208 0.2101 0.141 Uiso 1 1 calc R U . . .
H1AB H 0.3515 1.5736 0.1593 0.141 Uiso 1 1 calc R U . . .
C2 C 0.2426(5) 0.433(7) 0.6270(19) 0.42(2) Uani 1 1 d . U . . .
H2 H 0.2274 0.3815 0.5877 0.506 Uiso 1 1 calc R U . . .
C2A C 0.2992(2) 1.5616(12) 0.1468(6) 0.142(3) Uani 1 1 d . . . . .
H2A H 0.2950 1.6675 0.1726 0.170 Uiso 1 1 calc R U . . .
C3 C 0.2337(5) 0.558(6) 0.685(2) 0.381(16) Uani 1 1 d . U . . .
H3 H 0.2105 0.5860 0.6796 0.457 Uiso 1 1 calc R U . . .
C3A C 0.27389(18) 1.4850(14) 0.1005(7) 0.157(3) Uani 1 1 d . . . . .
H3A H 0.2525 1.5389 0.0968 0.188 Uiso 1 1 calc R U . . .
C4 C 0.2519(4) 0.649(5) 0.7501(13) 0.335(11) Uani 1 1 d . U . . .
H4A H 0.2478 0.5937 0.8008 0.402 Uiso 1 1 calc R U . . .
H4B H 0.2443 0.7712 0.7513 0.402 Uiso 1 1 calc R U . . .
C4A C 0.27755(15) 1.3250(11) 0.0558(6) 0.135(3) Uani 1 1 d . . . . .
H4BA H 0.2773 1.3547 -0.0007 0.161 Uiso 1 1 calc R U . . .
H4AA H 0.2579 1.2500 0.0619 0.161 Uiso 1 1 calc R U . . .
C5 C 0.2898(3) 0.640(3) 0.7373(11) 0.246(6) Uani 1 1 d . U . . .
H5 H 0.2949 0.7127 0.6912 0.295 Uiso 1 1 calc R U . . .
C5A C 0.31031(13) 1.2190(9) 0.0810(4) 0.1032(17) Uani 1 1 d . . . . .
H5A H 0.3074 1.1667 0.1336 0.124 Uiso 1 1 calc R U . . .
C6 C 0.3096(3) 0.705(3) 0.8135(9) 0.223(5) Uani 1 1 d . U . . .
H6A H 0.3045 0.6298 0.8582 0.267 Uiso 1 1 calc R U . . .
H6B H 0.3025 0.8246 0.8250 0.267 Uiso 1 1 calc R U . . .
C6A C 0.31596(13) 1.0709(9) 0.0257(5) 0.118(2) Uani 1 1 d . . . . .
H6AA H 0.3167 1.1178 -0.0282 0.142 Uiso 1 1 calc R U . . .
H6AB H 0.2966 0.9906 0.0247 0.142 Uiso 1 1 calc R U . . .
C7 C 0.3498(3) 0.7011(15) 0.8042(6) 0.160(3) Uani 1 1 d . U . . .
H7A H 0.3550 0.7819 0.7618 0.192 Uiso 1 1 calc R U . . .
H7B H 0.3623 0.7395 0.8539 0.192 Uiso 1 1 calc R U . . .
C7A C 0.34878(12) 0.9668(8) 0.0485(4) 0.1012(17) Uani 1 1 d . . . . .
H7AA H 0.3463 0.9013 0.0976 0.121 Uiso 1 1 calc R U . . .
H7AB H 0.3520 0.8816 0.0064 0.121 Uiso 1 1 calc R U . . .
C8 C 0.36046(16) 0.5191(11) 0.7843(4) 0.117(2) Uani 1 1 d . U . . .
H8 H 0.3573 0.4421 0.8303 0.140 Uiso 1 1 calc R U . . .
C8A C 0.38022(10) 1.0826(6) 0.0609(3) 0.0730(11) Uani 1 1 d . . . . .
H8A H 0.3845 1.1356 0.0092 0.088 Uiso 1 1 calc R U . . .
C9 C 0.33892(17) 0.4442(16) 0.7096(5) 0.140(3) Uani 1 1 d . U . . .
H9 H 0.3418 0.5244 0.6646 0.168 Uiso 1 1 calc R U . . .
C9A C 0.37367(10) 1.2332(6) 0.1205(3) 0.0705(11) Uani 1 1 d . . . . .
H9A H 0.3684 1.1748 0.1703 0.085 Uiso 1 1 calc R U . . .
C10 C 0.2984(3) 0.442(3) 0.7233(9) 0.215(5) Uani 1 1 d . U . . .
C10A C 0.34168(11) 1.3459(7) 0.0926(3) 0.0834(13) Uani 1 1 d . . . . .
C11 C 0.3511(2) 0.2601(16) 0.6856(5) 0.147(3) Uani 1 1 d . . . . .
H11A H 0.3465 0.1757 0.7271 0.176 Uiso 1 1 calc R U . . .
H11B H 0.3381 0.2238 0.6361 0.176 Uiso 1 1 calc R U . . .
C11A C 0.40597(11) 1.3442(7) 0.1426(3) 0.0807(12) Uani 1 1 d . . . . .
H11C H 0.4015 1.4277 0.1845 0.097 Uiso 1 1 calc R U . . .
H11D H 0.4114 1.4114 0.0959 0.097 Uiso 1 1 calc R U . . .
C12 C 0.38920(15) 0.2563(9) 0.6738(3) 0.1013(17) Uani 1 1 d . . . . .
H12A H 0.3961 0.1355 0.6637 0.122 Uiso 1 1 calc R U . . .
H12B H 0.3933 0.3270 0.6271 0.122 Uiso 1 1 calc R U . . .
C12A C 0.43714(10) 1.2279(7) 0.1720(3) 0.0751(11) Uani 1 1 d . . . . .
H12C H 0.4572 1.3024 0.1825 0.090 Uiso 1 1 calc R U . . .
H12D H 0.4328 1.1703 0.2220 0.090 Uiso 1 1 calc R U . . .
C13 C 0.41070(12) 0.3274(7) 0.7469(3) 0.0778(12) Uani 1 1 d . . . . .
C13A C 0.44401(9) 1.0892(6) 0.1104(2) 0.0607(9) Uani 1 1 d . . . . .
C14 C 0.39736(13) 0.5109(8) 0.7673(3) 0.0858(13) Uani 1 1 d . . . . .
H14 H 0.3994 0.5847 0.7197 0.103 Uiso 1 1 calc R U . . .
C14A C 0.41159(10) 0.9781(6) 0.0920(3) 0.0702(11) Uani 1 1 d . . . . .
H14A H 0.4063 0.9270 0.1434 0.084 Uiso 1 1 calc R U . . .
C15 C 0.42464(15) 0.5780(9) 0.8318(3) 0.1008(16) Uani 1 1 d . . . . .
H15A H 0.4199 0.5373 0.8847 0.121 Uiso 1 1 calc R U . . .
H15B H 0.4256 0.7063 0.8319 0.121 Uiso 1 1 calc R U . . .
C15A C 0.42360(13) 0.8255(7) 0.0427(3) 0.0859(13) Uani 1 1 d . . . . .
H15C H 0.4230 0.8578 -0.0137 0.103 Uiso 1 1 calc R U . . .
H15D H 0.4093 0.7220 0.0476 0.103 Uiso 1 1 calc R U . . .
C16 C 0.45881(14) 0.4979(8) 0.8076(3) 0.0903(14) Uani 1 1 d . . . . .
H16A H 0.4740 0.5906 0.7918 0.108 Uiso 1 1 calc R U . . .
H16B H 0.4704 0.4323 0.8521 0.108 Uiso 1 1 calc R U . . .
C16A C 0.46074(12) 0.7890(7) 0.0782(3) 0.0805(13) Uani 1 1 d . . . . .
H16C H 0.4622 0.6755 0.1055 0.097 Uiso 1 1 calc R U . . .
H16D H 0.4761 0.7876 0.0359 0.097 Uiso 1 1 calc R U . . .
C17 C 0.44854(12) 0.3735(7) 0.7362(2) 0.0749(12) Uani 1 1 d . . . . .
C17A C 0.47028(10) 0.9395(6) 0.1378(2) 0.0662(10) Uani 1 1 d . . . . .
C18 C 0.41014(16) 0.1967(9) 0.8163(3) 0.1042(17) Uani 1 1 d . . . . .
H18A H 0.4271 0.2303 0.8587 0.156 Uiso 1 1 calc R U . . .
H18B H 0.4151 0.0799 0.7979 0.156 Uiso 1 1 calc R U . . .
H18C H 0.3879 0.1978 0.8361 0.156 Uiso 1 1 calc R U . . .
C18A C 0.45623(13) 1.1781(7) 0.0355(3) 0.0829(13) Uani 1 1 d . . . . .
H18D H 0.4763 1.2476 0.0506 0.124 Uiso 1 1 calc R U . . .
H18E H 0.4384 1.2535 0.0113 0.124 Uiso 1 1 calc R U . . .
H18F H 0.4616 1.0889 -0.0023 0.124 Uiso 1 1 calc R U . . .
C19 C 0.2904(4) 0.312(3) 0.7873(12) 0.272(10) Uani 1 1 d . . . . .
H19A H 0.3057 0.3311 0.8348 0.409 Uiso 1 1 calc R U . . .
H19B H 0.2932 0.1935 0.7681 0.409 Uiso 1 1 calc R U . . .
H19C H 0.2671 0.3284 0.7998 0.409 Uiso 1 1 calc R U . . .
C19A C 0.34574(15) 1.4434(8) 0.0157(4) 0.1056(18) Uani 1 1 d . . . . .
H19D H 0.3248 1.5039 -0.0015 0.158 Uiso 1 1 calc R U . . .
H19E H 0.3510 1.3607 -0.0250 0.158 Uiso 1 1 calc R U . . .
H19F H 0.3640 1.5280 0.0243 0.158 Uiso 1 1 calc R U . . .
C20 C 0.45154(12) 0.4655(8) 0.6597(3) 0.0805(12) Uani 1 1 d . . . . .
C20A C 0.46635(11) 0.8845(7) 0.2221(3) 0.0730(11) Uani 1 1 d . . . . .
C21 C 0.45330(13) 0.5437(9) 0.5989(3) 0.0928(16) Uani 1 1 d . . . . .
C21A C 0.46348(11) 0.8385(7) 0.2885(3) 0.0782(12) Uani 1 1 d . . . . .
C22 C 0.45478(12) 0.6265(8) 0.5220(3) 0.0795(13) Uani 1 1 d . . . . .
C23 C 0.45550(15) 0.8026(8) 0.5106(3) 0.0872(15) Uani 1 1 d . . . . .
C24 C 0.45842(18) 0.8741(8) 0.4359(3) 0.0969(17) Uani 1 1 d . . . . .
H24 H 0.4592 0.9967 0.4311 0.116 Uiso 1 1 calc R U . . .
C25 C 0.46026(11) 0.7736(7) 0.3681(2) 0.0716(12) Uani 1 1 d . . . . .
C26 C 0.45895(16) 0.5923(8) 0.3791(3) 0.0916(15) Uani 1 1 d . . . . .
C27 C 0.4569(2) 0.5221(8) 0.4546(3) 0.114(2) Uani 1 1 d . . . . .
H27 H 0.4570 0.3997 0.4605 0.137 Uiso 1 1 calc R U . . .
N1 N 0.4576(3) 0.4794(12) 0.3191(4) 0.182(4) Uani 1 1 d . . . . .
H1BA H 0.4556 0.3680 0.3281 0.218 Uiso 1 1 calc R U . . .
H1C H 0.4588 0.5170 0.2708 0.218 Uiso 1 1 calc R U . . .
N2 N 0.4571(2) 0.9380(14) 0.5782(4) 0.147(3) Uani 1 1 d . . . . .
O1 O 0.50518(7) 0.9853(5) 0.13216(16) 0.0777(9) Uani 1 1 d . . . . .
H1ABB H 0.5105 1.0674 0.1629 0.117 Uiso 1 1 calc R U . . .
O2 O 0.47146(9) 0.2254(6) 0.74146(19) 0.0923(10) Uani 1 1 d D . . . .
O3 O 0.4483(3) 0.8869(13) 0.6423(4) 0.205(4) Uani 1 1 d . . . . .
O4 O 0.4660(3) 1.0869(14) 0.5704(6) 0.232(5) Uani 1 1 d . . . . .
H2B H 0.4673(14) 0.161(6) 0.698(2) 0.091(17) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.49(2) . ?
C1 C10 1.56(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1A C2A 1.510(10) . ?
C1A C10A 1.537(8) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2 C3 1.42(4) . ?
C2 H2 0.9300 . ?
C2A C3A 1.332(12) . ?
C2A H2A 0.9300 . ?
C3 C4 1.42(4) . ?
C3 H3 0.9300 . ?
C3A C4A 1.434(13) . ?
C3A H3A 0.9300 . ?
C4 C5 1.52(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4A C5A 1.538(9) . ?
C4A H4B 0.9700 . ?
C4A H4A 0.9700 . ?
C5 C6 1.51(2) . ?
C5 C10 1.56(3) . ?
C5 H5 0.9800 . ?
C5A C6A 1.480(10) . ?
C5A C10A 1.556(7) . ?
C5A H5A 0.9800 . ?
C6 C7 1.597(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6A C7A 1.525(8) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C7 C8 1.483(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7A C8A 1.509(7) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8 C14 1.500(8) . ?
C8 C9 1.548(12) . ?
C8 H8 0.9800 . ?
C8A C14A 1.511(6) . ?
C8A C9A 1.549(7) . ?
C8A H8A 0.9800 . ?
C9 C11 1.534(15) . ?
C9 C10 1.626(13) . ?
C9 H9 0.9800 . ?
C9A C11A 1.534(6) . ?
C9A C10A 1.550(6) . ?
C9A H9A 0.9800 . ?
C10 C19 1.51(2) . ?
C10A C19A 1.502(8) . ?
C11 C12 1.525(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11A C12A 1.547(7) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12 C13 1.516(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12A C13A 1.510(6) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C13 C18 1.524(7) . ?
C13 C14 1.530(8) . ?
C13 C17 1.549(7) . ?
C13A C14A 1.530(6) . ?
C13A C18A 1.535(6) . ?
C13A C17A 1.568(6) . ?
C14 C15 1.532(8) . ?
C14 H14 0.9800 . ?
C14A C15A 1.517(7) . ?
C14A H14A 0.9800 . ?
C15 C16 1.556(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15A C16A 1.544(7) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C16 C17 1.543(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16A C17A 1.534(7) . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?
C17 O2 1.432(6) . ?
C17 C20 1.467(7) . ?
C17A O1 1.422(5) . ?
C17A C20A 1.489(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18A H18D 0.9600 . ?
C18A H18E 0.9600 . ?
C18A H18F 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C20 C21 1.183(7) . ?
C20A C21A 1.178(6) . ?
C21 C22 1.435(7) . ?
C21A C25 1.433(6) . ?
C22 C23 1.344(8) . ?
C22 C27 1.383(8) . ?
C23 C24 1.375(7) . ?
C23 N2 1.521(9) . ?
C24 C25 1.370(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(8) . ?
C26 N1 1.313(9) . ?
C26 C27 1.376(8) . ?
C27 H27 0.9300 . ?
N1 H1B 0.8600 . ?
N1 H1C 0.8600 . ?
N2 O4 1.188(12) . ?
N2 O3 1.217(10) . ?
O1 H1A 0.8200 . ?
O2 H2B 0.871(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 116.1(19) . . ?
C2 C1 H1A 108.2 . . ?
C10 C1 H1A 108.2 . . ?
C2 C1 H1B 108.3 . . ?
C10 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C2A C1A C10A 113.8(6) . . ?
C2A C1A H1AA 108.8 . . ?
C10A C1A H1AA 108.8 . . ?
C2A C1A H1AB 108.8 . . ?
C10A C1A H1AB 108.8 . . ?
H1AA C1A H1AB 107.7 . . ?
C3 C2 C1 109(2) . . ?
C3 C2 H2 125.3 . . ?
C1 C2 H2 125.3 . . ?
C3A C2A C1A 121.3(7) . . ?
C3A C2A H2A 119.3 . . ?
C1A C2A H2A 119.3 . . ?
C4 C3 C2 135(2) . . ?
C4 C3 H3 112.5 . . ?
C2 C3 H3 112.5 . . ?
C2A C3A C4A 124.3(6) . . ?
C2A C3A H3A 117.9 . . ?
C4A C3A H3A 117.9 . . ?
C3 C4 C5 107.4(19) . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C3A C4A C5A 114.6(6) . . ?
C3A C4A H4B 108.6 . . ?
C5A C4A H4B 108.6 . . ?
C3A C4A H4A 108.6 . . ?
C5A C4A H4A 108.6 . . ?
H4B C4A H4A 107.6 . . ?
C6 C5 C4 107.3(15) . . ?
C6 C5 C10 109.6(13) . . ?
C4 C5 C10 106.8(19) . . ?
C6 C5 H5 111.0 . . ?
C4 C5 H5 111.0 . . ?
C10 C5 H5 111.0 . . ?
C6A C5A C4A 113.0(6) . . ?
C6A C5A C10A 112.4(5) . . ?
C4A C5A C10A 110.1(5) . . ?
C6A C5A H5A 107.0 . . ?
C4A C5A H5A 107.0 . . ?
C10A C5A H5A 107.0 . . ?
C5 C6 C7 110.2(10) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C5A C6A C7A 113.9(5) . . ?
C5A C6A H6AA 108.8 . . ?
C7A C6A H6AA 108.8 . . ?
C5A C6A H6AB 108.8 . . ?
C7A C6A H6AB 108.8 . . ?
H6AA C6A H6AB 107.7 . . ?
C8 C7 C6 109.9(11) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C8A C7A C6A 113.2(5) . . ?
C8A C7A H7AA 108.9 . . ?
C6A C7A H7AA 108.9 . . ?
C8A C7A H7AB 108.9 . . ?
C6A C7A H7AB 108.9 . . ?
H7AA C7A H7AB 107.7 . . ?
C7 C8 C14 112.2(7) . . ?
C7 C8 C9 112.0(7) . . ?
C14 C8 C9 107.1(5) . . ?
C7 C8 H8 108.5 . . ?
C14 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7A C8A C14A 111.9(4) . . ?
C7A C8A C9A 109.4(4) . . ?
C14A C8A C9A 109.9(3) . . ?
C7A C8A H8A 108.5 . . ?
C14A C8A H8A 108.5 . . ?
C9A C8A H8A 108.5 . . ?
C11 C9 C8 112.5(6) . . ?
C11 C9 C10 111.0(11) . . ?
C8 C9 C10 110.9(8) . . ?
C11 C9 H9 107.4 . . ?
C8 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
C11A C9A C8A 112.0(3) . . ?
C11A C9A C10A 113.5(4) . . ?
C8A C9A C10A 112.8(4) . . ?
C11A C9A H9A 106.0 . . ?
C8A C9A H9A 106.0 . . ?
C10A C9A H9A 106.0 . . ?
C19 C10 C5 117.4(14) . . ?
C19 C10 C1 113.2(18) . . ?
C5 C10 C1 104.9(16) . . ?
C19 C10 C9 112.1(11) . . ?
C5 C10 C9 103.8(14) . . ?
C1 C10 C9 104.1(10) . . ?
C19A C10A C1A 109.2(5) . . ?
C19A C10A C9A 112.3(4) . . ?
C1A C10A C9A 110.1(4) . . ?
C19A C10A C5A 109.8(5) . . ?
C1A C10A C5A 107.5(5) . . ?
C9A C10A C5A 107.9(4) . . ?
C12 C11 C9 112.4(7) . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C9A C11A C12A 112.1(4) . . ?
C9A C11A H11C 109.2 . . ?
C12A C11A H11C 109.2 . . ?
C9A C11A H11D 109.2 . . ?
C12A C11A H11D 109.2 . . ?
H11C C11A H11D 107.9 . . ?
C13 C12 C11 111.5(5) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C13A C12A C11A 111.2(4) . . ?
C13A C12A H12C 109.4 . . ?
C11A C12A H12C 109.4 . . ?
C13A C12A H12D 109.4 . . ?
C11A C12A H12D 109.4 . . ?
H12C C12A H12D 108.0 . . ?
C12 C13 C18 109.7(5) . . ?
C12 C13 C14 108.9(4) . . ?
C18 C13 C14 112.8(4) . . ?
C12 C13 C17 116.9(4) . . ?
C18 C13 C17 108.3(4) . . ?
C14 C13 C17 99.9(4) . . ?
C12A C13A C14A 108.7(3) . . ?
C12A C13A C18A 109.9(4) . . ?
C14A C13A C18A 113.0(3) . . ?
C12A C13A C17A 117.0(3) . . ?
C14A C13A C17A 100.0(3) . . ?
C18A C13A C17A 107.9(3) . . ?
C8 C14 C13 115.7(5) . . ?
C8 C14 C15 118.3(5) . . ?
C13 C14 C15 103.0(4) . . ?
C8 C14 H14 106.3 . . ?
C13 C14 H14 106.3 . . ?
C15 C14 H14 106.3 . . ?
C8A C14A C15A 119.5(4) . . ?
C8A C14A C13A 114.6(4) . . ?
C15A C14A C13A 103.5(3) . . ?
C8A C14A H14A 106.1 . . ?
C15A C14A H14A 106.1 . . ?
C13A C14A H14A 106.1 . . ?
C14 C15 C16 104.5(4) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C14A C15A C16A 104.8(4) . . ?
C14A C15A H15C 110.8 . . ?
C16A C15A H15C 110.8 . . ?
C14A C15A H15D 110.8 . . ?
C16A C15A H15D 110.8 . . ?
H15C C15A H15D 108.9 . . ?
C17 C16 C15 105.5(4) . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
C17A C16A C15A 106.4(4) . . ?
C17A C16A H16C 110.5 . . ?
C15A C16A H16C 110.5 . . ?
C17A C16A H16D 110.5 . . ?
C15A C16A H16D 110.5 . . ?
H16C C16A H16D 108.6 . . ?
O2 C17 C20 108.9(4) . . ?
O2 C17 C16 108.1(4) . . ?
C20 C17 C16 110.4(4) . . ?
O2 C17 C13 114.7(4) . . ?
C20 C17 C13 111.2(3) . . ?
C16 C17 C13 103.4(4) . . ?
O1 C17A C20A 108.3(3) . . ?
O1 C17A C16A 108.4(3) . . ?
C20A C17A C16A 111.5(4) . . ?
O1 C17A C13A 114.5(3) . . ?
C20A C17A C13A 110.8(3) . . ?
C16A C17A C13A 103.3(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13A C18A H18D 109.5 . . ?
C13A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C13A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10A C19A H19D 109.5 . . ?
C10A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C10A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C21 C20 C17 177.9(6) . . ?
C21A C20A C17A 178.9(5) . . ?
C20 C21 C22 175.7(7) . . ?
C20A C21A C25 177.2(6) . . ?
C23 C22 C27 116.5(4) . . ?
C23 C22 C21 124.1(5) . . ?
C27 C22 C21 119.4(5) . . ?
C22 C23 C24 121.4(5) . . ?
C22 C23 N2 124.1(6) . . ?
C24 C23 N2 114.1(6) . . ?
C25 C24 C23 123.2(5) . . ?
C25 C24 H24 118.4 . . ?
C23 C24 H24 118.4 . . ?
C24 C25 C26 115.6(4) . . ?
C24 C25 C21A 126.4(5) . . ?
C26 C25 C21A 118.0(4) . . ?
N1 C26 C27 116.6(6) . . ?
N1 C26 C25 122.7(5) . . ?
C27 C26 C25 120.6(4) . . ?
C26 C27 C22 122.6(5) . . ?
C26 C27 H27 118.7 . . ?
C22 C27 H27 118.7 . . ?
C26 N1 H1B 120.0 . . ?
C26 N1 H1C 120.0 . . ?
H1B N1 H1C 120.0 . . ?
O4 N2 O3 120.5(9) . . ?
O4 N2 C23 123.1(8) . . ?
O3 N2 C23 116.4(10) . . ?
C17A O1 H1A 109.5 . . ?
C17 O2 H2B 108(4) . . ?

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
C10 C1 C2 C3 21(4) . . . . ?
C10A C1A C2A C3A 19.8(12) . . . . ?
C1 C2 C3 C4 -1(6) . . . . ?
C1A C2A C3A C4A -2.0(16) . . . . ?
C2 C3 C4 C5 18(6) . . . . ?
C2A C3A C4A C5A 14.9(14) . . . . ?
C3 C4 C5 C6 -169(3) . . . . ?
C3 C4 C5 C10 -52(3) . . . . ?
C3A C4A C5A C6A -170.9(7) . . . . ?
C3A C4A C5A C10A -44.3(10) . . . . ?
C4 C5 C6 C7 -179.5(17) . . . . ?
C10 C5 C6 C7 64.9(19) . . . . ?
C4A C5A C6A C7A 178.6(6) . . . . ?
C10A C5A C6A C7A 53.2(7) . . . . ?
C5 C6 C7 C8 -57.7(17) . . . . ?
C5A C6A C7A C8A -52.1(8) . . . . ?
C6 C7 C8 C14 174.7(7) . . . . ?
C6 C7 C8 C9 54.1(10) . . . . ?
C6A C7A C8A C14A 173.9(5) . . . . ?
C6A C7A C8A C9A 51.9(7) . . . . ?
C7 C8 C9 C11 176.8(7) . . . . ?
C14 C8 C9 C11 53.4(8) . . . . ?
C7 C8 C9 C10 -58.3(12) . . . . ?
C14 C8 C9 C10 178.3(10) . . . . ?
C7A C8A C9A C11A 174.0(4) . . . . ?
C14A C8A C9A C11A 50.8(5) . . . . ?
C7A C8A C9A C10A -56.6(5) . . . . ?
C14A C8A C9A C10A -179.8(4) . . . . ?
C6 C5 C10 C19 59.9(16) . . . . ?
C4 C5 C10 C19 -56.1(18) . . . . ?
C6 C5 C10 C1 -173.4(13) . . . . ?
C4 C5 C10 C1 70.6(18) . . . . ?
C6 C5 C10 C9 -64.4(16) . . . . ?
C4 C5 C10 C9 179.6(12) . . . . ?
C2 C1 C10 C19 74(3) . . . . ?
C2 C1 C10 C5 -56(3) . . . . ?
C2 C1 C10 C9 -164(3) . . . . ?
C11 C9 C10 C19 58.5(14) . . . . ?
C8 C9 C10 C19 -67.3(16) . . . . ?
C11 C9 C10 C5 -173.8(10) . . . . ?
C8 C9 C10 C5 60.4(14) . . . . ?
C11 C9 C10 C1 -64.3(18) . . . . ?
C8 C9 C10 C1 170.0(15) . . . . ?
C2A C1A C10A C19A 71.5(7) . . . . ?
C2A C1A C10A C9A -164.8(6) . . . . ?
C2A C1A C10A C5A -47.6(8) . . . . ?
C11A C9A C10A C19A 64.6(6) . . . . ?
C8A C9A C10A C19A -64.0(5) . . . . ?
C11A C9A C10A C1A -57.2(6) . . . . ?
C8A C9A C10A C1A 174.1(4) . . . . ?
C11A C9A C10A C5A -174.2(4) . . . . ?
C8A C9A C10A C5A 57.2(5) . . . . ?
C6A C5A C10A C19A 67.9(6) . . . . ?
C4A C5A C10A C19A -59.0(7) . . . . ?
C6A C5A C10A C1A -173.4(5) . . . . ?
C4A C5A C10A C1A 59.6(7) . . . . ?
C6A C5A C10A C9A -54.8(6) . . . . ?
C4A C5A C10A C9A 178.2(6) . . . . ?
C8 C9 C11 C12 -54.0(9) . . . . ?
C10 C9 C11 C12 -178.9(7) . . . . ?
C8A C9A C11A C12A -52.3(5) . . . . ?
C10A C9A C11A C12A 178.6(4) . . . . ?
C9 C11 C12 C13 53.8(9) . . . . ?
C9A C11A C12A C13A 55.9(5) . . . . ?
C11 C12 C13 C18 70.4(7) . . . . ?
C11 C12 C13 C14 -53.5(7) . . . . ?
C11 C12 C13 C17 -165.7(6) . . . . ?
C11A C12A C13A C14A -56.7(5) . . . . ?
C11A C12A C13A C18A 67.5(5) . . . . ?
C11A C12A C13A C17A -168.9(4) . . . . ?
C7 C8 C14 C13 179.5(6) . . . . ?
C9 C8 C14 C13 -57.2(7) . . . . ?
C7 C8 C14 C15 56.5(8) . . . . ?
C9 C8 C14 C15 179.8(6) . . . . ?
C12 C13 C14 C8 58.4(6) . . . . ?
C18 C13 C14 C8 -63.7(6) . . . . ?
C17 C13 C14 C8 -178.5(4) . . . . ?
C12 C13 C14 C15 -170.9(4) . . . . ?
C18 C13 C14 C15 67.0(5) . . . . ?
C17 C13 C14 C15 -47.8(4) . . . . ?
C7A C8A C14A C15A 59.6(6) . . . . ?
C9A C8A C14A C15A -178.6(4) . . . . ?
C7A C8A C14A C13A -176.8(4) . . . . ?
C9A C8A C14A C13A -55.0(5) . . . . ?
C12A C13A C14A C8A 58.4(5) . . . . ?
C18A C13A C14A C8A -64.0(5) . . . . ?
C17A C13A C14A C8A -178.5(3) . . . . ?
C12A C13A C14A C15A -169.8(4) . . . . ?
C18A C13A C14A C15A 67.9(5) . . . . ?
C17A C13A C14A C15A -46.6(4) . . . . ?
C8 C14 C15 C16 162.7(5) . . . . ?
C13 C14 C15 C16 33.6(6) . . . . ?
C8A C14A C15A C16A 163.5(4) . . . . ?
C13A C14A C15A C16A 34.6(5) . . . . ?
C14 C15 C16 C17 -6.0(6) . . . . ?
C14A C15A C16A C17A -8.2(5) . . . . ?
C15 C16 C17 O2 -145.4(4) . . . . ?
C15 C16 C17 C20 95.6(5) . . . . ?
C15 C16 C17 C13 -23.4(5) . . . . ?
C12 C13 C17 O2 -81.7(5) . . . . ?
C18 C13 C17 O2 42.9(5) . . . . ?
C14 C13 C17 O2 161.1(4) . . . . ?
C12 C13 C17 C20 42.5(6) . . . . ?
C18 C13 C17 C20 167.0(5) . . . . ?
C14 C13 C17 C20 -74.8(5) . . . . ?
C12 C13 C17 C16 160.9(5) . . . . ?
C18 C13 C17 C16 -74.5(5) . . . . ?
C14 C13 C17 C16 43.7(4) . . . . ?
C15A C16A C17A O1 -142.2(4) . . . . ?
C15A C16A C17A C20A 98.6(4) . . . . ?
C15A C16A C17A C13A -20.4(5) . . . . ?
C12A C13A C17A O1 -84.4(4) . . . . ?
C14A C13A C17A O1 158.5(3) . . . . ?
C18A C13A C17A O1 40.1(4) . . . . ?
C12A C13A C17A C20A 38.4(5) . . . . ?
C14A C13A C17A C20A -78.7(4) . . . . ?
C18A C13A C17A C20A 163.0(4) . . . . ?
C12A C13A C17A C16A 157.9(3) . . . . ?
C14A C13A C17A C16A 40.8(4) . . . . ?
C18A C13A C17A C16A -77.5(4) . . . . ?
C27 C22 C23 C24 -0.4(9) . . . . ?
C21 C22 C23 C24 177.1(5) . . . . ?
C27 C22 C23 N2 -173.4(6) . . . . ?
C21 C22 C23 N2 4.1(9) . . . . ?
C22 C23 C24 C25 1.0(9) . . . . ?
N2 C23 C24 C25 174.7(6) . . . . ?
C23 C24 C25 C26 0.1(8) . . . . ?
C23 C24 C25 C21A -179.7(5) . . . . ?
C24 C25 C26 N1 174.3(7) . . . . ?
C21A C25 C26 N1 -5.9(9) . . . . ?
C24 C25 C26 C27 -1.8(9) . . . . ?
C21A C25 C26 C27 178.0(5) . . . . ?
N1 C26 C27 C22 -173.7(7) . . . . ?
C25 C26 C27 C22 2.6(10) . . . . ?
C23 C22 C27 C26 -1.4(9) . . . . ?
C21 C22 C27 C26 -179.0(6) . . . . ?
C22 C23 N2 O4 161.0(10) . . . . ?
C24 C23 N2 O4 -12.5(12) . . . . ?
C22 C23 N2 O3 -19.9(10) . . . . ?
C24 C23 N2 O3 166.6(7) . . . . ?

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
O1 H1A O2 0.82 2.07 2.868(5) 166.1 2_666
O2 H2B N2 0.871(14) 2.623(18) 3.490(9) 174(5) 1_545
O2 H2B O3 0.871(14) 2.37(3) 3.134(10) 147(5) 1_545
O2 H2B O4 0.871(14) 2.21(3) 3.032(10) 158(5) 1_545
O1 H1A O2 0.82 2.07 2.868(5) 166.1 2_666
O2 H2B N2 0.871(14) 2.623(18) 3.490(9) 174(5) 1_545
O2 H2B O3 0.871(14) 2.37(3) 3.134(10) 147(5) 1_545
O2 H2B O4 0.871(14) 2.21(3) 3.032(10) 158(5) 1_545

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.032



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2:Hexanes'
####################################################################### 
# 
# 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_Steroidal_compass_8
_database_code_depnum_ccdc_archive 'CCDC 1525777'
_audit_update_record             
;
2017-01-05 deposited with the CCDC.
2017-03-01 downloaded from the CCDC.
;
#============================================================================

_audit_creation_date             2016-10-18T13:06:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'2,5-Bis(17alpha-ethynyl-estra-1,3,5-(10)-trien-17beta-ol-3-methyl ether)-4-nitroaniline'
_chemical_melting_point          468
_chemical_formula_moiety         'C48 H54 N2 O6'
_chemical_formula_sum            'C48 H54 N2 O6'
_chemical_formula_weight         754.93
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
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'

_cell_length_a                   11.8249(2)
_cell_length_b                   13.9462(3)
_cell_length_c                   26.1937(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4319.67(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    128242
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  0.865
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.989

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.064669
_diffrn_orient_matrix_ub_12      0.000136
_diffrn_orient_matrix_ub_13      0.024601
_diffrn_orient_matrix_ub_21      -0.031923
_diffrn_orient_matrix_ub_22      -0.058206
_diffrn_orient_matrix_ub_23      -0.017012
_diffrn_orient_matrix_ub_31      0.044164
_diffrn_orient_matrix_ub_32      -0.041875
_diffrn_orient_matrix_ub_33      0.023726
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_number            43642
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.807
_reflns_number_total             9642
_reflns_number_gt                6766
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
'Refined as a 2-component inversion twin., Twin,SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0937P)²+0.0612P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9642
_refine_ls_number_parameters     574
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(15)
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.036
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.022 0.819 0.678 105 20 .
2 0.022 0.319 0.822 105 20 .
3 0.049 0.135 0.325 12 0 .
4 0.522 0.181 0.178 105 20 .
5 0.478 0.681 0.322 105 20 .
6 0.45 0.865 0.825 12 0 .
7 0.549 0.365 0.675 12 0 .
8 0.95 0.635 0.175 12 0 .

_platon_squeeze_void_probe_radius 1.2

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0904(3) -0.3902(2) 0.27736(12) 0.0512(7) Uani 1 1 d . . . . .
H1 H 0.054 -0.3389 0.26 0.061 Uiso 1 1 calc R U . . .
C1A C 0.8680(3) 0.5568(3) 0.51512(14) 0.0674(9) Uani 1 1 d . . . . .
H1B H 0.8049 0.5951 0.5057 0.081 Uiso 1 1 calc R U . . .
C2 C 0.1115(3) -0.4739(2) 0.25156(13) 0.0616(8) Uani 1 1 d . . . . .
H2A H 0.0895 -0.4801 0.2168 0.074 Uiso 1 1 calc R U . . .
C2A C 0.9270(4) 0.5803(3) 0.55784(16) 0.0790(11) Uani 1 1 d . . . . .
H2D H 0.9045 0.6341 0.5777 0.095 Uiso 1 1 calc R U . . .
C3 C 0.1640(3) -0.5481(2) 0.27562(14) 0.0636(9) Uani 1 1 d . . . . .
C3A C 1.0184(4) 0.5271(4) 0.57246(16) 0.0841(12) Uani 1 1 d . . . . .
C4 C 0.1958(3) -0.5395(2) 0.32616(14) 0.0622(9) Uani 1 1 d . . . . .
H4 H 0.2317 -0.5916 0.3431 0.075 Uiso 1 1 calc R U . . .
C4A C 1.0516(4) 0.4489(4) 0.54313(17) 0.0829(11) Uani 1 1 d . . . . .
H4A H 1.1159 0.4124 0.5529 0.099 Uiso 1 1 calc R U . . .
C5 C 0.1750(3) -0.4536(2) 0.35243(12) 0.0535(7) Uani 1 1 d . . . . .
C5A C 0.9901(3) 0.4233(3) 0.49888(15) 0.0716(10) Uani 1 1 d . . . . .
C6 C 0.2081(4) -0.4490(2) 0.40854(14) 0.0711(10) Uani 1 1 d . . . . .
H6A H 0.1595 -0.494 0.4279 0.085 Uiso 1 1 calc R U . . .
H6B H 0.2872 -0.4714 0.412 0.085 Uiso 1 1 calc R U . . .
C6A C 1.0287(3) 0.3375(3) 0.46937(18) 0.0815(11) Uani 1 1 d . . . . .
H6C H 1.0456 0.285 0.4937 0.098 Uiso 1 1 calc R U . . .
H6D H 1.0998 0.3538 0.4514 0.098 Uiso 1 1 calc R U . . .
C7 C 0.1984(3) -0.3507(2) 0.43240(12) 0.0566(8) Uani 1 1 d . . . . .
H7A H 0.2654 -0.3119 0.4231 0.068 Uiso 1 1 calc R U . . .
H7B H 0.1967 -0.357 0.47 0.068 Uiso 1 1 calc R U . . .
C7A C 0.9428(4) 0.3009(3) 0.43007(17) 0.0755(10) Uani 1 1 d . . . . .
H7C H 0.9814 0.258 0.4055 0.091 Uiso 1 1 calc R U . . .
H7D H 0.8836 0.2633 0.4477 0.091 Uiso 1 1 calc R U . . .
C8 C 0.0910(3) -0.2999(2) 0.41421(11) 0.0446(6) Uani 1 1 d . . . . .
C8A C 0.8879(3) 0.3837(3) 0.40119(15) 0.0620(9) Uani 1 1 d . . . . .
C9 C 0.0979(3) -0.28404(19) 0.35607(11) 0.0431(6) Uani 1 1 d . . . . .
C9A C 0.8237(3) 0.4481(2) 0.43940(14) 0.0599(8) Uani 1 1 d . . . . .
C10 C 0.1210(3) -0.3785(2) 0.32827(11) 0.0456(6) Uani 1 1 d . . . . .
C10A C 0.8968(3) 0.4780(2) 0.48439(14) 0.0627(9) Uani 1 1 d . . . . .
C11 C -0.0050(3) -0.2301(2) 0.33546(13) 0.0495(7) Uani 1 1 d . . . . .
C11A C 0.7656(3) 0.5311(2) 0.41164(16) 0.0681(10) Uani 1 1 d . . . . .
H11C H 0.8237 0.572 0.3954 0.082 Uiso 1 1 calc R U . . .
H11D H 0.7244 0.5708 0.4368 0.082 Uiso 1 1 calc R U . . .
C12 C -0.0259(3) -0.1352(2) 0.36377(12) 0.0478(7) Uani 1 1 d . . . . .
C12A C 0.6824(3) 0.4961(2) 0.37076(15) 0.0651(9) Uani 1 1 d . . . . .
H12C H 0.6197 0.4606 0.3872 0.078 Uiso 1 1 calc R U . . .
H12D H 0.6499 0.5519 0.3525 0.078 Uiso 1 1 calc R U . . .
C13 C -0.0328(2) -0.15066(18) 0.42102(11) 0.0428(6) Uani 1 1 d . . . . .
C13A C 0.7422(3) 0.4316(2) 0.33318(14) 0.0602(8) Uani 1 1 d . . . . .
C14 C 0.0733(3) -0.20307(19) 0.44003(11) 0.0429(6) Uani 1 1 d . . . . .
C14A C 0.8035(3) 0.3507(2) 0.36091(14) 0.0608(8) Uani 1 1 d . . . . .
C15 C 0.0657(3) -0.1972(2) 0.49841(11) 0.0533(7) Uani 1 1 d . . . . .
H15A H 0.142 -0.1967 0.514 0.064 Uiso 1 1 calc R U . . .
H15B H 0.0224 -0.252 0.5124 0.064 Uiso 1 1 calc R U . . .
C15A C 0.8420(4) 0.2830(3) 0.31778(17) 0.0825(12) Uani 1 1 d . . . . .
H15C H 0.8452 0.2157 0.3297 0.099 Uiso 1 1 calc R U . . .
H15D H 0.9174 0.3017 0.3046 0.099 Uiso 1 1 calc R U . . .
C16 C 0.0039(3) -0.1021(2) 0.50823(12) 0.0547(8) Uani 1 1 d . . . . .
C16A C 0.7490(4) 0.2962(3) 0.27612(16) 0.0818(12) Uani 1 1 d . . . . .
H16C H 0.7833 0.3175 0.2436 0.098 Uiso 1 1 calc R U . . .
H16D H 0.7087 0.2351 0.2701 0.098 Uiso 1 1 calc R U . . .
C17 C -0.0260(2) -0.0590(2) 0.45531(12) 0.0465(7) Uani 1 1 d . . . . .
C17A C 0.6675(3) 0.3721(3) 0.29623(14) 0.0641(9) Uani 1 1 d . . . . .
C18 C -0.1421(3) -0.2046(2) 0.43461(14) 0.0566(8) Uani 1 1 d . . . . .
H18A H -0.1458 -0.2645 0.415 0.085 Uiso 1 1 calc R U . . .
H18B H -0.2076 -0.1646 0.4263 0.085 Uiso 1 1 calc R U . . .
H18C H -0.1426 -0.2193 0.4712 0.085 Uiso 1 1 calc R U . . .
C18A C 0.8234(4) 0.4931(3) 0.29974(18) 0.0866(12) Uani 1 1 d . . . . .
H18D H 0.88 0.5239 0.3216 0.13 Uiso 1 1 calc R U . . .
H18E H 0.7799 0.5423 0.2817 0.13 Uiso 1 1 calc R U . . .
H18F H 0.8616 0.4517 0.2749 0.13 Uiso 1 1 calc R U . . .
C19 C 0.2317(6) -0.7090(3) 0.2695(2) 0.132(2) Uani 1 1 d . . . . .
H19A H 0.1864 -0.7296 0.2988 0.197 Uiso 1 1 calc R U . . .
H19B H 0.3078 -0.6915 0.281 0.197 Uiso 1 1 calc R U . . .
H19C H 0.2367 -0.7615 0.2447 0.197 Uiso 1 1 calc R U . . .
C19A C 1.1567(5) 0.4940(6) 0.6372(2) 0.132(2) Uani 1 1 d . . . . .
H19D H 1.1821 0.5205 0.6699 0.198 Uiso 1 1 calc R U . . .
H19E H 1.2207 0.4913 0.6135 0.198 Uiso 1 1 calc R U . . .
H19F H 1.1268 0.4293 0.6425 0.198 Uiso 1 1 calc R U . . .
C20 C 0.0648(3) 0.0050(2) 0.43777(11) 0.0464(7) Uani 1 1 d . . . . .
C20A C 0.5744(3) 0.3230(2) 0.32416(13) 0.0576(8) Uani 1 1 d . . . . .
C21 C 0.1409(2) 0.05528(19) 0.42489(12) 0.0471(7) Uani 1 1 d . . . . .
C21A C 0.5026(3) 0.2806(2) 0.34665(13) 0.0548(7) Uani 1 1 d . . . . .
C22 C 0.2341(2) 0.11244(18) 0.40655(11) 0.0445(6) Uani 1 1 d . . . . .
C23 C 0.2920(3) 0.08420(19) 0.36212(11) 0.0467(7) Uani 1 1 d . . . . .
C24 C 0.3814(3) 0.1408(2) 0.34420(12) 0.0494(7) Uani 1 1 d . . . . .
H24 H 0.4205 0.1219 0.3142 0.059 Uiso 1 1 calc R U . . .
C25 C 0.4143(2) 0.2247(2) 0.36953(12) 0.0477(7) Uani 1 1 d . . . . .
C26 C 0.3575(2) 0.24912(18) 0.41438(11) 0.0459(7) Uani 1 1 d . . . . .
C27 C 0.2683(2) 0.19382(19) 0.43265(12) 0.0455(6) Uani 1 1 d . . . . .
H27 H 0.2306 0.212 0.4632 0.055 Uiso 1 1 calc R U . . .
N1 N 0.3866(3) 0.33065(19) 0.44485(12) 0.0640(7) Uani 1 1 d . . . . .
N2 N 0.2624(3) 0.0030(2) 0.33656(14) 0.0718(9) Uani 1 1 d . . . . .
O1 O -0.13175(18) -0.01047(16) 0.45433(9) 0.0603(6) Uani 1 1 d D . . . .
O2 O 0.6186(3) 0.4253(2) 0.25468(10) 0.0793(8) Uani 1 1 d D . . . .
O3 O 0.3248(3) 0.35463(18) 0.47984(11) 0.0820(8) Uani 1 1 d . . . . .
O4 O 0.4734(4) 0.3724(3) 0.43663(16) 0.1454(18) Uani 1 1 d . . . . .
O5 O 0.1804(3) -0.62943(19) 0.24644(12) 0.0985(11) Uani 1 1 d . . . . .
O6 O 1.0715(3) 0.5529(3) 0.61668(13) 0.1173(12) Uani 1 1 d . . . . .
H1A H -0.139(3) 0.028(2) 0.4794(9) 0.062(10) Uiso 1 1 d D . . . .
H2 H 0.568(5) 0.469(4) 0.263(3) 0.18(4) Uiso 1 1 d D . . . .
H2B H 0.203(5) -0.038(4) 0.351(2) 0.115(16) Uiso 1 1 d . . . . .
H2C H 0.306(4) -0.024(3) 0.3096(18) 0.092(13) Uiso 1 1 d . . . . .
H8 H 0.024(2) -0.3438(19) 0.4225(10) 0.037(7) Uiso 1 1 d . . . . .
H8A H 0.945(3) 0.420(3) 0.3862(13) 0.061(9) Uiso 1 1 d . . . . .
H9 H 0.165(2) -0.2457(19) 0.3505(10) 0.031(6) Uiso 1 1 d . . . . .
H9A H 0.754(3) 0.411(2) 0.4521(13) 0.058(9) Uiso 1 1 d . . . . .
H11A H -0.077(3) -0.271(3) 0.3391(14) 0.067(10) Uiso 1 1 d . . . . .
H11B H 0.010(3) -0.219(2) 0.3010(14) 0.049(8) Uiso 1 1 d . . . . .
H12A H -0.094(3) -0.102(2) 0.3510(12) 0.051(8) Uiso 1 1 d . . . . .
H12B H 0.036(2) -0.089(2) 0.3565(11) 0.037(7) Uiso 1 1 d . . . . .
H14 H 0.138(2) -0.163(2) 0.4311(10) 0.039(7) Uiso 1 1 d . . . . .
H14A H 0.743(3) 0.316(2) 0.3797(13) 0.060(9) Uiso 1 1 d . . . . .
H16A H -0.062(3) -0.110(3) 0.5300(14) 0.065(10) Uiso 1 1 d . . . . .
H16B H 0.053(3) -0.062(3) 0.5247(15) 0.069(10) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.372(4) . ?
C1 C10 1.391(4) . ?
C1 H1 0.95 . ?
C1A C2A 1.359(6) . ?
C1A C10A 1.404(5) . ?
C1A H1B 0.95 . ?
C2 C3 1.361(5) . ?
C2 H2A 0.95 . ?
C2A C3A 1.365(6) . ?
C2A H2D 0.95 . ?
C3 O5 1.381(4) . ?
C3 C4 1.381(5) . ?
C3A O6 1.366(5) . ?
C3A C4A 1.391(7) . ?
C4 C5 1.404(4) . ?
C4 H4 0.95 . ?
C4A C5A 1.414(6) . ?
C4A H4A 0.95 . ?
C5 C10 1.380(4) . ?
C5 C6 1.522(5) . ?
C5A C10A 1.394(5) . ?
C5A C6A 1.496(6) . ?
C6 C7 1.511(4) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C6A C7A 1.533(6) . ?
C6A H6C 0.99 . ?
C6A H6D 0.99 . ?
C7 C8 1.531(4) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C7A C8A 1.526(5) . ?
C7A H7C 0.99 . ?
C7A H7D 0.99 . ?
C8 C14 1.524(4) . ?
C8 C9 1.541(4) . ?
C8 H8 1.03(3) . ?
C8A C14A 1.524(5) . ?
C8A C9A 1.544(5) . ?
C8A H8A 0.93(4) . ?
C9 C11 1.529(4) . ?
C9 C10 1.530(4) . ?
C9 H9 0.97(3) . ?
C9A C10A 1.520(5) . ?
C9A C11A 1.530(5) . ?
C9A H9A 1.03(3) . ?
C11 C12 1.537(4) . ?
C11 H11A 1.02(4) . ?
C11 H11B 0.93(3) . ?
C11A C12A 1.534(5) . ?
C11A H11C 0.99 . ?
C11A H11D 0.99 . ?
C12 C13 1.517(4) . ?
C12 H12A 0.98(3) . ?
C12 H12B 0.99(3) . ?
C12A C13A 1.510(5) . ?
C12A H12C 0.99 . ?
C12A H12D 0.99 . ?
C13 C14 1.536(4) . ?
C13 C18 1.537(4) . ?
C13 C17 1.564(4) . ?
C13A C14A 1.526(5) . ?
C13A C17A 1.551(5) . ?
C13A C18A 1.557(5) . ?
C14 C15 1.534(4) . ?
C14 H14 0.98(3) . ?
C14A C15A 1.541(5) . ?
C14A H14A 0.99(4) . ?
C15 C16 1.536(5) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C15A C16A 1.561(6) . ?
C15A H15C 0.99 . ?
C15A H15D 0.99 . ?
C16 C17 1.552(5) . ?
C16 H16A 0.97(4) . ?
C16 H16B 0.91(4) . ?
C16A C17A 1.525(6) . ?
C16A H16C 0.99 . ?
C16A H16D 0.99 . ?
C17 O1 1.422(4) . ?
C17 C20 1.470(4) . ?
C17A O2 1.439(5) . ?
C17A C20A 1.489(5) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C18A H18D 0.98 . ?
C18A H18E 0.98 . ?
C18A H18F 0.98 . ?
C19 O5 1.401(5) . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C19A O6 1.407(8) . ?
C19A H19D 0.98 . ?
C19A H19E 0.98 . ?
C19A H19F 0.98 . ?
C20 C21 1.190(4) . ?
C20A C21A 1.190(4) . ?
C21 C22 1.443(4) . ?
C21A C25 1.434(4) . ?
C22 C27 1.385(4) . ?
C22 C23 1.406(4) . ?
C23 N2 1.361(4) . ?
C23 C24 1.401(4) . ?
C24 C25 1.400(4) . ?
C24 H24 0.95 . ?
C25 C26 1.395(4) . ?
C26 C27 1.391(4) . ?
C26 N1 1.431(4) . ?
C27 H27 0.95 . ?
N1 O4 1.199(4) . ?
N1 O3 1.218(4) . ?
N2 H2B 0.97(6) . ?
N2 H2C 0.95(5) . ?
O1 H1A 0.852(13) . ?
O2 H2 0.873(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 121.6(3) . . ?
C2 C1 H1 119.2 . . ?
C10 C1 H1 119.2 . . ?
C2A C1A C10A 122.4(4) . . ?
C2A C1A H1B 118.8 . . ?
C10A C1A H1B 118.8 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C1A C2A C3A 120.4(4) . . ?
C1A C2A H2D 119.8 . . ?
C3A C2A H2D 119.8 . . ?
C2 C3 O5 115.6(3) . . ?
C2 C3 C4 120.1(3) . . ?
O5 C3 C4 124.3(3) . . ?
C2A C3A O6 117.3(4) . . ?
C2A C3A C4A 119.6(4) . . ?
O6 C3A C4A 123.0(5) . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C3A C4A C5A 120.4(4) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C10 C5 C4 120.3(3) . . ?
C10 C5 C6 122.0(3) . . ?
C4 C5 C6 117.6(3) . . ?
C10A C5A C4A 119.5(4) . . ?
C10A C5A C6A 122.6(4) . . ?
C4A C5A C6A 118.0(4) . . ?
C7 C6 C5 114.7(3) . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C5A C6A C7A 114.3(3) . . ?
C5A C6A H6C 108.7 . . ?
C7A C6A H6C 108.7 . . ?
C5A C6A H6D 108.7 . . ?
C7A C6A H6D 108.7 . . ?
H6C C6A H6D 107.6 . . ?
C6 C7 C8 110.7(3) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8A C7A C6A 111.3(3) . . ?
C8A C7A H7C 109.4 . . ?
C6A C7A H7C 109.4 . . ?
C8A C7A H7D 109.4 . . ?
C6A C7A H7D 109.4 . . ?
H7C C7A H7D 108 . . ?
C14 C8 C7 112.7(2) . . ?
C14 C8 C9 108.6(2) . . ?
C7 C8 C9 109.2(3) . . ?
C14 C8 H8 109.2(14) . . ?
C7 C8 H8 107.6(14) . . ?
C9 C8 H8 109.5(15) . . ?
C14A C8A C7A 113.1(3) . . ?
C14A C8A C9A 107.6(3) . . ?
C7A C8A C9A 109.2(3) . . ?
C14A C8A H8A 110(2) . . ?
C7A C8A H8A 108(2) . . ?
C9A C8A H8A 108(2) . . ?
C11 C9 C10 113.4(2) . . ?
C11 C9 C8 112.1(2) . . ?
C10 C9 C8 110.9(2) . . ?
C11 C9 H9 109.0(15) . . ?
C10 C9 H9 105.0(15) . . ?
C8 C9 H9 105.8(15) . . ?
C10A C9A C11A 114.7(3) . . ?
C10A C9A C8A 112.5(3) . . ?
C11A C9A C8A 110.7(3) . . ?
C10A C9A H9A 110.1(19) . . ?
C11A C9A H9A 100.1(18) . . ?
C8A C9A H9A 108.0(18) . . ?
C5 C10 C1 118.1(3) . . ?
C5 C10 C9 121.2(3) . . ?
C1 C10 C9 120.7(3) . . ?
C5A C10A C1A 117.7(4) . . ?
C5A C10A C9A 120.8(3) . . ?
C1A C10A C9A 121.4(3) . . ?
C9 C11 C12 112.4(3) . . ?
C9 C11 H11A 111(2) . . ?
C12 C11 H11A 108(2) . . ?
C9 C11 H11B 105.5(19) . . ?
C12 C11 H11B 111.0(18) . . ?
H11A C11 H11B 110(3) . . ?
C9A C11A C12A 112.3(3) . . ?
C9A C11A H11C 109.1 . . ?
C12A C11A H11C 109.1 . . ?
C9A C11A H11D 109.1 . . ?
C12A C11A H11D 109.1 . . ?
H11C C11A H11D 107.9 . . ?
C13 C12 C11 111.3(2) . . ?
C13 C12 H12A 111.0(18) . . ?
C11 C12 H12A 112.0(18) . . ?
C13 C12 H12B 108.8(16) . . ?
C11 C12 H12B 110.1(16) . . ?
H12A C12 H12B 103(2) . . ?
C13A C12A C11A 110.1(3) . . ?
C13A C12A H12C 109.6 . . ?
C11A C12A H12C 109.6 . . ?
C13A C12A H12D 109.6 . . ?
C11A C12A H12D 109.6 . . ?
H12C C12A H12D 108.1 . . ?
C12 C13 C14 110.1(2) . . ?
C12 C13 C18 110.1(3) . . ?
C14 C13 C18 112.3(2) . . ?
C12 C13 C17 116.7(2) . . ?
C14 C13 C17 99.2(2) . . ?
C18 C13 C17 108.1(2) . . ?
C12A C13A C14A 110.7(3) . . ?
C12A C13A C17A 117.3(3) . . ?
C14A C13A C17A 99.9(3) . . ?
C12A C13A C18A 109.1(3) . . ?
C14A C13A C18A 112.5(3) . . ?
C17A C13A C18A 107.2(3) . . ?
C8 C14 C15 119.8(2) . . ?
C8 C14 C13 112.9(2) . . ?
C15 C14 C13 104.5(2) . . ?
C8 C14 H14 107.5(16) . . ?
C15 C14 H14 104.6(16) . . ?
C13 C14 H14 106.5(15) . . ?
C8A C14A C13A 114.6(3) . . ?
C8A C14A C15A 120.0(3) . . ?
C13A C14A C15A 104.1(3) . . ?
C8A C14A H14A 106.0(19) . . ?
C13A C14A H14A 104.5(19) . . ?
C15A C14A H14A 106(2) . . ?
C14 C15 C16 103.9(2) . . ?
C14 C15 H15A 111 . . ?
C16 C15 H15A 111 . . ?
C14 C15 H15B 111 . . ?
C16 C15 H15B 111 . . ?
H15A C15 H15B 109 . . ?
C14A C15A C16A 103.4(3) . . ?
C14A C15A H15C 111.1 . . ?
C16A C15A H15C 111.1 . . ?
C14A C15A H15D 111.1 . . ?
C16A C15A H15D 111.1 . . ?
H15C C15A H15D 109 . . ?
C15 C16 C17 107.1(2) . . ?
C15 C16 H16A 112(2) . . ?
C17 C16 H16A 113(2) . . ?
C15 C16 H16B 108(2) . . ?
C17 C16 H16B 109(2) . . ?
H16A C16 H16B 107(3) . . ?
C17A C16A C15A 106.6(3) . . ?
C17A C16A H16C 110.4 . . ?
C15A C16A H16C 110.4 . . ?
C17A C16A H16D 110.4 . . ?
C15A C16A H16D 110.4 . . ?
H16C C16A H16D 108.6 . . ?
O1 C17 C20 110.3(2) . . ?
O1 C17 C16 113.7(2) . . ?
C20 C17 C16 110.3(3) . . ?
O1 C17 C13 109.5(2) . . ?
C20 C17 C13 110.8(2) . . ?
C16 C17 C13 102.0(2) . . ?
O2 C17A C20A 108.2(3) . . ?
O2 C17A C16A 110.5(3) . . ?
C20A C17A C16A 108.5(3) . . ?
O2 C17A C13A 115.2(3) . . ?
C20A C17A C13A 111.2(3) . . ?
C16A C17A C13A 103.1(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13A C18A H18D 109.5 . . ?
C13A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C13A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C19A H19D 109.5 . . ?
O6 C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
O6 C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C21 C20 C17 177.6(3) . . ?
C21A C20A C17A 177.4(4) . . ?
C20 C21 C22 176.4(3) . . ?
C20A C21A C25 174.8(4) . . ?
C27 C22 C23 119.7(3) . . ?
C27 C22 C21 120.7(3) . . ?
C23 C22 C21 119.5(2) . . ?
N2 C23 C24 119.9(3) . . ?
N2 C23 C22 121.0(3) . . ?
C24 C23 C22 119.1(2) . . ?
C23 C24 C25 121.5(3) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 117.9(3) . . ?
C26 C25 C21A 124.7(3) . . ?
C24 C25 C21A 117.3(3) . . ?
C27 C26 C25 121.3(2) . . ?
C27 C26 N1 115.5(3) . . ?
C25 C26 N1 123.2(3) . . ?
C22 C27 C26 120.4(3) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
O4 N1 O3 121.0(3) . . ?
O4 N1 C26 119.4(3) . . ?
O3 N1 C26 119.6(3) . . ?
C23 N2 H2B 119(3) . . ?
C23 N2 H2C 123(3) . . ?
H2B N2 H2C 117(4) . . ?
C17 O1 H1A 112(2) . . ?
C17A O2 H2 117(5) . . ?
C3 O5 C19 118.2(3) . . ?
C3A O6 C19A 120.0(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
C10 C1 C2 C3 -0.3(5) . . . . ?
C10A C1A C2A C3A 0.3(6) . . . . ?
C1 C2 C3 O5 179.4(3) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C1A C2A C3A O6 -177.9(4) . . . . ?
C1A C2A C3A C4A 0.5(6) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
O5 C3 C4 C5 -179.9(4) . . . . ?
C2A C3A C4A C5A -1.1(6) . . . . ?
O6 C3A C4A C5A 177.2(4) . . . . ?
C3 C4 C5 C10 1.3(5) . . . . ?
C3 C4 C5 C6 177.9(4) . . . . ?
C3A C4A C5A C10A 0.9(6) . . . . ?
C3A C4A C5A C6A -179.0(4) . . . . ?
C10 C5 C6 C7 -11.5(5) . . . . ?
C4 C5 C6 C7 171.9(3) . . . . ?
C10A C5A C6A C7A -13.7(5) . . . . ?
C4A C5A C6A C7A 166.2(4) . . . . ?
C5 C6 C7 C8 40.9(5) . . . . ?
C5A C6A C7A C8A 42.3(5) . . . . ?
C6 C7 C8 C14 176.1(3) . . . . ?
C6 C7 C8 C9 -63.1(4) . . . . ?
C6A C7A C8A C14A 178.8(3) . . . . ?
C6A C7A C8A C9A -61.3(4) . . . . ?
C14 C8 C9 C11 -54.7(3) . . . . ?
C7 C8 C9 C11 -177.9(2) . . . . ?
C14 C8 C9 C10 177.5(2) . . . . ?
C7 C8 C9 C10 54.2(3) . . . . ?
C14A C8A C9A C10A 174.5(3) . . . . ?
C7A C8A C9A C10A 51.4(4) . . . . ?
C14A C8A C9A C11A -55.8(4) . . . . ?
C7A C8A C9A C11A -178.9(3) . . . . ?
C4 C5 C10 C1 -1.3(5) . . . . ?
C6 C5 C10 C1 -177.8(3) . . . . ?
C4 C5 C10 C9 -179.7(3) . . . . ?
C6 C5 C10 C9 3.8(5) . . . . ?
C2 C1 C10 C5 0.8(5) . . . . ?
C2 C1 C10 C9 179.2(3) . . . . ?
C11 C9 C10 C5 -152.7(3) . . . . ?
C8 C9 C10 C5 -25.5(4) . . . . ?
C11 C9 C10 C1 28.9(4) . . . . ?
C8 C9 C10 C1 156.1(3) . . . . ?
C4A C5A C10A C1A -0.2(5) . . . . ?
C6A C5A C10A C1A 179.7(3) . . . . ?
C4A C5A C10A C9A -175.3(3) . . . . ?
C6A C5A C10A C9A 4.6(5) . . . . ?
C2A C1A C10A C5A -0.4(5) . . . . ?
C2A C1A C10A C9A 174.7(3) . . . . ?
C11A C9A C10A C5A -151.4(3) . . . . ?
C8A C9A C10A C5A -23.8(4) . . . . ?
C11A C9A C10A C1A 33.7(4) . . . . ?
C8A C9A C10A C1A 161.2(3) . . . . ?
C10 C9 C11 C12 -179.7(3) . . . . ?
C8 C9 C11 C12 53.8(4) . . . . ?
C10A C9A C11A C12A -173.3(3) . . . . ?
C8A C9A C11A C12A 58.2(4) . . . . ?
C9 C11 C12 C13 -53.3(4) . . . . ?
C9A C11A C12A C13A -56.3(4) . . . . ?
C11 C12 C13 C14 54.3(3) . . . . ?
C11 C12 C13 C18 -70.0(3) . . . . ?
C11 C12 C13 C17 166.4(3) . . . . ?
C11A C12A C13A C14A 53.4(4) . . . . ?
C11A C12A C13A C17A 167.1(3) . . . . ?
C11A C12A C13A C18A -70.9(4) . . . . ?
C7 C8 C14 C15 -57.6(4) . . . . ?
C9 C8 C14 C15 -178.8(3) . . . . ?
C7 C8 C14 C13 178.6(2) . . . . ?
C9 C8 C14 C13 57.5(3) . . . . ?
C12 C13 C14 C8 -58.3(3) . . . . ?
C18 C13 C14 C8 64.8(3) . . . . ?
C17 C13 C14 C8 178.7(2) . . . . ?
C12 C13 C14 C15 169.9(2) . . . . ?
C18 C13 C14 C15 -67.1(3) . . . . ?
C17 C13 C14 C15 46.9(3) . . . . ?
C7A C8A C14A C13A 176.9(3) . . . . ?
C9A C8A C14A C13A 56.2(4) . . . . ?
C7A C8A C14A C15A -58.0(5) . . . . ?
C9A C8A C14A C15A -178.7(3) . . . . ?
C12A C13A C14A C8A -56.3(4) . . . . ?
C17A C13A C14A C8A 179.4(3) . . . . ?
C18A C13A C14A C8A 66.1(4) . . . . ?
C12A C13A C14A C15A 170.7(3) . . . . ?
C17A C13A C14A C15A 46.4(3) . . . . ?
C18A C13A C14A C15A -66.9(4) . . . . ?
C8 C14 C15 C16 -158.7(3) . . . . ?
C13 C14 C15 C16 -31.0(3) . . . . ?
C8A C14A C15A C16A -160.5(3) . . . . ?
C13A C14A C15A C16A -30.6(4) . . . . ?
C14 C15 C16 C17 2.3(3) . . . . ?
C14A C15A C16A C17A 2.4(4) . . . . ?
C15 C16 C17 O1 144.0(2) . . . . ?
C15 C16 C17 C20 -91.4(3) . . . . ?
C15 C16 C17 C13 26.3(3) . . . . ?
C12 C13 C17 O1 77.1(3) . . . . ?
C14 C13 C17 O1 -164.7(2) . . . . ?
C18 C13 C17 O1 -47.5(3) . . . . ?
C12 C13 C17 C20 -44.8(4) . . . . ?
C14 C13 C17 C20 73.4(3) . . . . ?
C18 C13 C17 C20 -169.4(3) . . . . ?
C12 C13 C17 C16 -162.2(3) . . . . ?
C14 C13 C17 C16 -44.0(3) . . . . ?
C18 C13 C17 C16 73.2(3) . . . . ?
C15A C16A C17A O2 149.5(3) . . . . ?
C15A C16A C17A C20A -92.0(4) . . . . ?
C15A C16A C17A C13A 25.9(4) . . . . ?
C12A C13A C17A O2 75.8(4) . . . . ?
C14A C13A C17A O2 -164.6(3) . . . . ?
C18A C13A C17A O2 -47.3(4) . . . . ?
C12A C13A C17A C20A -47.7(4) . . . . ?
C14A C13A C17A C20A 71.9(3) . . . . ?
C18A C13A C17A C20A -170.7(3) . . . . ?
C12A C13A C17A C16A -163.7(3) . . . . ?
C14A C13A C17A C16A -44.2(3) . . . . ?
C18A C13A C17A C16A 73.2(4) . . . . ?
C27 C22 C23 N2 178.0(3) . . . . ?
C21 C22 C23 N2 -1.0(4) . . . . ?
C27 C22 C23 C24 -1.9(4) . . . . ?
C21 C22 C23 C24 179.1(3) . . . . ?
N2 C23 C24 C25 -179.9(3) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
C23 C24 C25 C26 1.9(4) . . . . ?
C23 C24 C25 C21A -176.6(3) . . . . ?
C24 C25 C26 C27 -2.1(4) . . . . ?
C21A C25 C26 C27 176.3(3) . . . . ?
C24 C25 C26 N1 177.2(3) . . . . ?
C21A C25 C26 N1 -4.4(5) . . . . ?
C23 C22 C27 C26 1.7(4) . . . . ?
C21 C22 C27 C26 -179.3(3) . . . . ?
C25 C26 C27 C22 0.3(4) . . . . ?
N1 C26 C27 C22 -179.1(3) . . . . ?
C27 C26 N1 O4 167.6(4) . . . . ?
C25 C26 N1 O4 -11.7(5) . . . . ?
C27 C26 N1 O3 -9.9(4) . . . . ?
C25 C26 N1 O3 170.8(3) . . . . ?
C2 C3 O5 C19 -178.6(5) . . . . ?
C4 C3 O5 C19 0.6(7) . . . . ?
C2A C3A O6 C19A 171.9(4) . . . . ?
C4A C3A O6 C19A -6.5(6) . . . . ?






# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
