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

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

data_indole
_database_code_depnum_ccdc_archive 'CCDC 1482067'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_audit_creation_date             2016-05-11
_audit_creation_method           
#==========================================================================

# SUBMISSION DETAILS
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
#==========================================================================
# CHEMICAL DATA
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#==========================================================================

# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.451(4)
_cell_length_b                   14.313(4)
_cell_length_c                   15.248(4)
_cell_angle_alpha                86.714(4)
_cell_angle_beta                 63.827(3)
_cell_angle_gamma                90.014(4)
_cell_volume                     2629.3(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.428
_cell_measurement_theta_min      2.240
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
#==========================================================================

# Experimental data 
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0695 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.8807.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23224
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.590
_diffrn_reflns_theta_max         24.590
_diffrn_reflns_theta_min         1.426
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6320
_reflns_number_total             8719
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         8719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1378
#==========================================================================

# Refinement data
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5340(14) 0.4660(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), N1B(H1B), C2B(H2B), C3B(H3B), C6B(H6B), C8B(H8B), C12B(H12B),
 C13B(H13B), C15B(H15B), C16B(H16B), N1D(H1D), C2D(H2D), C3D(H3D), C6D(H6D),
 C8D(H8D), C12D(H12D), C13D(H13D), C15D(H15D), C16D(H16D), N1F(H1F), C2F(H2F),
 C3F(H3F), C6F(H6F), C8F(H8F), C12F(H12F), C13F(H13F), C15F(H15F), C16F(H16F)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C17(H17A,H17B,H17C), C7B(H7BA,H7BB,H7BC), C17B(H17D,H17E,
 H17F), C7D(H7DA,H7DB,H7DC), C17D(H17G,H17H,H17I), C7F(H7FA,H7FB,H7FC),
 C17F(H17J,H17K,H17L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 -0.0694(2) 0.82086(19) 0.3858(2) 0.0344(8) Uani 1 1 d . . . . .
O2 O 0.0698(2) 0.31075(19) 0.3842(2) 0.0290(7) Uani 1 1 d . . . . .
N1 N -0.0024(3) 0.4875(2) 0.3896(2) 0.0227(8) Uani 1 1 d . . . . .
H1 H 0.0576 0.4831 0.3989 0.027 Uiso 1 1 calc R . . . .
C1 C -0.0868(4) 0.7278(3) 0.3814(3) 0.0288(11) Uani 1 1 d . . . . .
C2 C -0.1817(4) 0.7073(3) 0.3683(3) 0.0321(12) Uani 1 1 d . . . . .
H2 H -0.2254 0.7571 0.3623 0.039 Uiso 1 1 calc R . . . .
C3 C -0.2120(4) 0.6179(3) 0.3640(3) 0.0295(10) Uani 1 1 d . . . . .
H3 H -0.2770 0.6050 0.3564 0.035 Uiso 1 1 calc R . . . .
C4 C -0.1466(4) 0.5454(3) 0.3709(3) 0.0245(10) Uani 1 1 d . . . . .
C5 C -0.0522(4) 0.5687(3) 0.3842(3) 0.0266(11) Uani 1 1 d . . . . .
C6 C -0.0201(3) 0.6585(3) 0.3892(3) 0.0237(10) Uani 1 1 d . . . . .
H6 H 0.0443 0.6718 0.3975 0.028 Uiso 1 1 calc R . . . .
C7 C 0.0211(4) 0.8463(3) 0.4054(3) 0.0327(12) Uani 1 1 d . . . . .
H7A H 0.0908 0.8287 0.3515 0.049 Uiso 1 1 calc GR . . . .
H7B H 0.0126 0.8135 0.4666 0.049 Uiso 1 1 calc GR . . . .
H7C H 0.0222 0.9140 0.4114 0.049 Uiso 1 1 calc GR . . . .
C8 C -0.1507(4) 0.4465(3) 0.3681(3) 0.0205(10) Uani 1 1 d . . . . .
H8 H -0.2055 0.4107 0.3606 0.025 Uiso 1 1 calc R . . . .
C9 C -0.0603(4) 0.4123(3) 0.3784(3) 0.0235(11) Uani 1 1 d . . . . .
C10 C -0.0196(3) 0.3207(3) 0.3799(3) 0.0229(10) Uani 1 1 d . . . . .
C11 C -0.0802(4) 0.2369(3) 0.3752(3) 0.0249(10) Uani 1 1 d . . . . .
C12 C -0.1946(4) 0.2282(3) 0.4160(3) 0.0279(10) Uani 1 1 d . . . . .
H12 H -0.2385 0.2791 0.4477 0.034 Uiso 1 1 calc R . . . .
C13 C -0.2446(4) 0.1479(3) 0.4113(3) 0.0304(11) Uani 1 1 d . . . . .
H13 H -0.3232 0.1443 0.4402 0.036 Uiso 1 1 calc R . . . .
C14 C -0.1865(4) 0.0705(3) 0.3665(3) 0.0274(10) Uani 1 1 d . . . . .
C15 C -0.0720(4) 0.0794(3) 0.3254(3) 0.0274(10) Uani 1 1 d . . . . .
H15 H -0.0286 0.0285 0.2929 0.033 Uiso 1 1 calc R . . . .
C16 C -0.0188(4) 0.1613(3) 0.3305(3) 0.0268(11) Uani 1 1 d . . . . .
H16 H 0.0598 0.1649 0.3033 0.032 Uiso 1 1 calc R . . . .
C17 C -0.2438(4) -0.0164(3) 0.3646(3) 0.0347(12) Uani 1 1 d . . . . .
H17A H -0.2540 -0.0586 0.4210 0.052 Uiso 1 1 calc GR . . . .
H17B H -0.1993 -0.0469 0.3040 0.052 Uiso 1 1 calc GR . . . .
H17C H -0.3163 -0.0016 0.3674 0.052 Uiso 1 1 calc GR . . . .
O1B O 0.3504(3) 0.0181(2) 0.3658(2) 0.0356(8) Uani 1 1 d . . . . .
O2B O 0.2047(2) 0.52938(19) 0.3842(2) 0.0306(7) Uani 1 1 d . . . . .
N1B N 0.2718(3) 0.3492(2) 0.3894(2) 0.0245(8) Uani 1 1 d . . . . .
H1B H 0.2014 0.3516 0.4020 0.029 Uiso 1 1 calc R . . . .
C1B C 0.3721(4) 0.1116(3) 0.3646(3) 0.0291(11) Uani 1 1 d . . . . .
C2B C 0.4821(4) 0.1356(3) 0.3448(3) 0.0286(11) Uani 1 1 d . . . . .
H2B H 0.5341 0.0875 0.3340 0.034 Uiso 1 1 calc R . . . .
C3B C 0.5148(3) 0.2243(3) 0.3410(3) 0.0257(10) Uani 1 1 d . . . . .
H3B H 0.5893 0.2388 0.3274 0.031 Uiso 1 1 calc R . . . .
C4B C 0.4394(4) 0.2962(3) 0.3569(3) 0.0267(10) Uani 1 1 d . . . . .
C5B C 0.3296(4) 0.2696(3) 0.3776(3) 0.0250(11) Uani 1 1 d . . . . .
C6B C 0.2936(4) 0.1783(3) 0.3816(3) 0.0264(11) Uani 1 1 d . . . . .
H6B H 0.2193 0.1627 0.3953 0.032 Uiso 1 1 calc R . . . .
C7B C 0.2430(4) -0.0100(3) 0.3817(3) 0.0356(13) Uani 1 1 d . . . . .
H7BA H 0.2265 0.0196 0.3302 0.053 Uiso 1 1 calc GR . . . .
H7BB H 0.1888 0.0091 0.4457 0.053 Uiso 1 1 calc GR . . . .
H7BC H 0.2389 -0.0782 0.3802 0.053 Uiso 1 1 calc GR . . . .
C8B C 0.4437(4) 0.3949(3) 0.3580(3) 0.0240(11) Uani 1 1 d . . . . .
H8B H 0.5069 0.4326 0.3465 0.029 Uiso 1 1 calc R . . . .
C9B C 0.3392(4) 0.4263(3) 0.3787(3) 0.0217(10) Uani 1 1 d . . . . .
C10B C 0.2963(4) 0.5178(3) 0.3837(3) 0.0239(10) Uani 1 1 d . . . . .
C11B C 0.3612(3) 0.6001(3) 0.3850(3) 0.0239(10) Uani 1 1 d . . . . .
C12B C 0.4274(3) 0.5973(3) 0.4346(3) 0.0268(10) Uani 1 1 d . . . . .
H12B H 0.4340 0.5402 0.4663 0.032 Uiso 1 1 calc R . . . .
C13B C 0.4834(3) 0.6770(3) 0.4378(3) 0.0292(10) Uani 1 1 d . . . . .
H13B H 0.5269 0.6744 0.4728 0.035 Uiso 1 1 calc R . . . .
C14B C 0.4767(4) 0.7600(3) 0.3911(3) 0.0285(11) Uani 1 1 d . . . . .
C15B C 0.4108(4) 0.7630(3) 0.3422(3) 0.0273(11) Uani 1 1 d . . . . .
H15B H 0.4056 0.8200 0.3096 0.033 Uiso 1 1 calc R . . . .
C16B C 0.3527(4) 0.6845(3) 0.3403(3) 0.0268(11) Uani 1 1 d . . . . .
H16B H 0.3065 0.6884 0.3079 0.032 Uiso 1 1 calc R . . . .
C17B C 0.5368(4) 0.8467(3) 0.3948(3) 0.0323(12) Uani 1 1 d . . . . .
H17D H 0.5354 0.8482 0.4595 0.048 Uiso 1 1 calc GR . . . .
H17E H 0.5005 0.9020 0.3828 0.048 Uiso 1 1 calc GR . . . .
H17F H 0.6138 0.8466 0.3446 0.048 Uiso 1 1 calc GR . . . .
O1D O 0.3169(2) -0.32445(18) 0.1219(2) 0.0302(8) Uani 1 1 d . . . . .
O2D O 0.4532(2) 0.18895(19) 0.1121(2) 0.0288(7) Uani 1 1 d . . . . .
N1D N 0.3836(3) 0.0105(2) 0.1163(2) 0.0244(8) Uani 1 1 d . . . . .
H1D H 0.4528 0.0156 0.1070 0.029 Uiso 1 1 calc R . . . .
C1D C 0.2920(4) -0.2316(3) 0.1277(3) 0.0256(11) Uani 1 1 d . . . . .
C2D C 0.1843(4) -0.2131(3) 0.1450(3) 0.0289(11) Uani 1 1 d . . . . .
H2D H 0.1350 -0.2640 0.1533 0.035 Uiso 1 1 calc R . . . .
C3D C 0.1468(3) -0.1255(3) 0.1506(3) 0.0268(10) Uani 1 1 d . . . . .
H3D H 0.0729 -0.1141 0.1613 0.032 Uiso 1 1 calc R . . . .
C4D C 0.2208(4) -0.0510(3) 0.1400(3) 0.0231(10) Uani 1 1 d . . . . .
C5D C 0.3286(4) -0.0714(3) 0.1239(3) 0.0205(10) Uani 1 1 d . . . . .
C6D C 0.3670(4) -0.1620(3) 0.1175(3) 0.0250(10) Uani 1 1 d . . . . .
H6D H 0.4406 -0.1750 0.1068 0.030 Uiso 1 1 calc R . . . .
C7D C 0.4300(4) -0.3473(3) 0.0886(3) 0.0365(13) Uani 1 1 d . . . . .
H7DA H 0.4735 -0.3180 0.0227 0.055 Uiso 1 1 calc GR . . . .
H7DB H 0.4369 -0.4154 0.0868 0.055 Uiso 1 1 calc GR . . . .
H7DC H 0.4577 -0.3242 0.1332 0.055 Uiso 1 1 calc GR . . . .
C8D C 0.2128(4) 0.0483(3) 0.1412(3) 0.0265(11) Uani 1 1 d . . . . .
H8D H 0.1491 0.0832 0.1511 0.032 Uiso 1 1 calc R . . . .
C9D C 0.3152(4) 0.0839(3) 0.1252(3) 0.0219(11) Uani 1 1 d . . . . .
C10D C 0.3577(4) 0.1776(3) 0.1196(3) 0.0235(10) Uani 1 1 d . . . . .
C11D C 0.2919(3) 0.2602(3) 0.1244(3) 0.0238(11) Uani 1 1 d . . . . .
C12D C 0.2133(4) 0.2637(3) 0.0881(3) 0.0257(10) Uani 1 1 d . . . . .
H12D H 0.1986 0.2106 0.0605 0.031 Uiso 1 1 calc R . . . .
C13D C 0.1568(4) 0.3453(3) 0.0929(3) 0.0274(10) Uani 1 1 d . . . . .
H13D H 0.1030 0.3475 0.0683 0.033 Uiso 1 1 calc R . . . .
C14D C 0.1760(4) 0.4234(3) 0.1321(3) 0.0279(10) Uani 1 1 d . . . . .
C15D C 0.2544(4) 0.4190(3) 0.1676(3) 0.0284(11) Uani 1 1 d . . . . .
H15D H 0.2684 0.4722 0.1953 0.034 Uiso 1 1 calc R . . . .
C16D C 0.3111(4) 0.3409(3) 0.1635(3) 0.0234(10) Uani 1 1 d . . . . .
H16D H 0.3653 0.3402 0.1875 0.028 Uiso 1 1 calc R . . . .
C17D C 0.1149(4) 0.5106(3) 0.1330(3) 0.0344(13) Uani 1 1 d . . . . .
H17G H 0.1199 0.5255 0.0676 0.052 Uiso 1 1 calc GR . . . .
H17H H 0.1477 0.5624 0.1517 0.052 Uiso 1 1 calc GR . . . .
H17I H 0.0369 0.5012 0.1803 0.052 Uiso 1 1 calc GR . . . .
O1F O 0.7125(3) 0.48530(19) 0.1337(2) 0.0372(8) Uani 1 1 d . . . . .
O2F O 0.5921(2) -0.02943(18) 0.1073(2) 0.0297(7) Uani 1 1 d . . . . .
N1F N 0.6618(3) 0.1530(2) 0.1022(2) 0.0251(8) Uani 1 1 d . . . . .
H1F H 0.6059 0.1502 0.0872 0.030 Uiso 1 1 calc R . . . .
C1F C 0.7315(4) 0.3908(3) 0.1342(3) 0.0289(11) Uani 1 1 d . . . . .
C2F C 0.8179(4) 0.3684(3) 0.1587(3) 0.0292(11) Uani 1 1 d . . . . .
H2F H 0.8556 0.4171 0.1728 0.035 Uiso 1 1 calc R . . . .
C3F C 0.8494(4) 0.2779(3) 0.1628(3) 0.0314(11) Uani 1 1 d . . . . .
H3F H 0.9078 0.2629 0.1798 0.038 Uiso 1 1 calc R . . . .
C4F C 0.7921(4) 0.2086(3) 0.1411(3) 0.0242(10) Uani 1 1 d . . . . .
C5F C 0.7062(4) 0.2332(3) 0.1166(3) 0.0239(10) Uani 1 1 d . . . . .
C6F C 0.6749(4) 0.3250(3) 0.1128(3) 0.0273(11) Uani 1 1 d . . . . .
H6F H 0.6166 0.3408 0.0961 0.033 Uiso 1 1 calc R . . . .
C7F C 0.6258(4) 0.5132(3) 0.1091(4) 0.0401(13) Uani 1 1 d . . . . .
H7FA H 0.6401 0.4906 0.0453 0.060 Uiso 1 1 calc GR . . . .
H7FB H 0.6228 0.5817 0.1060 0.060 Uiso 1 1 calc GR . . . .
H7FC H 0.5549 0.4866 0.1590 0.060 Uiso 1 1 calc GR . . . .
C8F C 0.7988(4) 0.1083(3) 0.1387(3) 0.0272(12) Uani 1 1 d . . . . .
H8F H 0.8497 0.0705 0.1512 0.033 Uiso 1 1 calc R . . . .
C9F C 0.7178(4) 0.0779(3) 0.1149(3) 0.0278(12) Uani 1 1 d . . . . .
C10F C 0.6826(3) -0.0151(3) 0.1082(3) 0.0239(10) Uani 1 1 d . . . . .
C11F C 0.7512(4) -0.0954(3) 0.1067(3) 0.0251(11) Uani 1 1 d . . . . .
C12F C 0.8652(3) -0.0900(3) 0.0615(3) 0.0290(10) Uani 1 1 d . . . . .
H12F H 0.9024 -0.0321 0.0310 0.035 Uiso 1 1 calc R . . . .
C13F C 0.9261(4) -0.1683(3) 0.0601(3) 0.0292(10) Uani 1 1 d . . . . .
H13F H 1.0047 -0.1638 0.0267 0.035 Uiso 1 1 calc R . . . .
C14F C 0.8751(4) -0.2524(3) 0.1061(3) 0.0305(11) Uani 1 1 d . . . . .
C15F C 0.7607(4) -0.2570(3) 0.1499(3) 0.0306(11) Uani 1 1 d . . . . .
H15F H 0.7239 -0.3147 0.1813 0.037 Uiso 1 1 calc R . . . .
C16F C 0.6989(4) -0.1820(3) 0.1496(3) 0.0274(11) Uani 1 1 d . . . . .
H16F H 0.6204 -0.1884 0.1786 0.033 Uiso 1 1 calc R . . . .
C17F C 0.9413(4) -0.3357(3) 0.1062(3) 0.0375(13) Uani 1 1 d . . . . .
H17J H 1.0146 -0.3292 0.0499 0.056 Uiso 1 1 calc GR . . . .
H17K H 0.9032 -0.3924 0.1018 0.056 Uiso 1 1 calc GR . . . .
H17L H 0.9499 -0.3405 0.1668 0.056 Uiso 1 1 calc GR . . . .

#==========================================================================

# 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
O1 C1 1.363(5) . ?
O1 C7 1.427(6) . ?
O2 C10 1.240(5) . ?
N1 H1 0.8800 . ?
N1 C5 1.359(5) . ?
N1 C9 1.391(5) . ?
C1 C2 1.410(7) . ?
C1 C6 1.373(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.356(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(6) . ?
C4 C5 1.414(6) . ?
C4 C8 1.419(6) . ?
C5 C6 1.372(6) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.380(6) . ?
C9 C10 1.423(6) . ?
C10 C11 1.473(6) . ?
C11 C12 1.384(6) . ?
C11 C16 1.382(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.353(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(6) . ?
C14 C15 1.385(6) . ?
C14 C17 1.472(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.397(6) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O1B C1B 1.367(5) . ?
O1B C7B 1.411(6) . ?
O2B C10B 1.239(5) . ?
N1B H1B 0.8800 . ?
N1B C5B 1.355(5) . ?
N1B C9B 1.384(5) . ?
C1B C2B 1.413(7) . ?
C1B C6B 1.371(6) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.333(6) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.399(6) . ?
C4B C5B 1.414(6) . ?
C4B C8B 1.415(6) . ?
C5B C6B 1.383(6) . ?
C6B H6B 0.9500 . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
C8B H8B 0.9500 . ?
C8B C9B 1.380(6) . ?
C9B C10B 1.424(6) . ?
C10B C11B 1.472(6) . ?
C11B C12B 1.399(6) . ?
C11B C16B 1.383(5) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.381(6) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.374(5) . ?
C14B C15B 1.386(6) . ?
C14B C17B 1.498(6) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.378(6) . ?
C16B H16B 0.9500 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
O1D C1D 1.369(5) . ?
O1D C7D 1.420(6) . ?
O2D C10D 1.249(5) . ?
N1D H1D 0.8800 . ?
N1D C5D 1.356(5) . ?
N1D C9D 1.370(5) . ?
C1D C2D 1.381(7) . ?
C1D C6D 1.371(6) . ?
C2D H2D 0.9500 . ?
C2D C3D 1.345(5) . ?
C3D H3D 0.9500 . ?
C3D C4D 1.411(6) . ?
C4D C5D 1.394(6) . ?
C4D C8D 1.425(6) . ?
C5D C6D 1.389(6) . ?
C6D H6D 0.9500 . ?
C7D H7DA 0.9800 . ?
C7D H7DB 0.9800 . ?
C7D H7DC 0.9800 . ?
C8D H8D 0.9500 . ?
C8D C9D 1.380(7) . ?
C9D C10D 1.441(6) . ?
C10D C11D 1.462(6) . ?
C11D C12D 1.394(6) . ?
C11D C16D 1.404(6) . ?
C12D H12D 0.9500 . ?
C12D C13D 1.381(6) . ?
C13D H13D 0.9500 . ?
C13D C14D 1.374(6) . ?
C14D C15D 1.380(6) . ?
C14D C17D 1.493(6) . ?
C15D H15D 0.9500 . ?
C15D C16D 1.343(6) . ?
C16D H16D 0.9500 . ?
C17D H17G 0.9800 . ?
C17D H17H 0.9800 . ?
C17D H17I 0.9800 . ?
O1F C1F 1.377(5) . ?
O1F C7F 1.424(5) . ?
O2F C10F 1.240(5) . ?
N1F H1F 0.8800 . ?
N1F C5F 1.366(5) . ?
N1F C9F 1.365(5) . ?
C1F C2F 1.402(7) . ?
C1F C6F 1.351(6) . ?
C2F H2F 0.9500 . ?
C2F C3F 1.369(6) . ?
C3F H3F 0.9500 . ?
C3F C4F 1.397(6) . ?
C4F C5F 1.402(6) . ?
C4F C8F 1.439(6) . ?
C5F C6F 1.385(6) . ?
C6F H6F 0.9500 . ?
C7F H7FA 0.9800 . ?
C7F H7FB 0.9800 . ?
C7F H7FC 0.9800 . ?
C8F H8F 0.9500 . ?
C8F C9F 1.369(7) . ?
C9F C10F 1.437(6) . ?
C10F C11F 1.469(6) . ?
C11F C12F 1.376(6) . ?
C11F C16F 1.401(6) . ?
C12F H12F 0.9500 . ?
C12F C13F 1.383(5) . ?
C13F H13F 0.9500 . ?
C13F C14F 1.376(6) . ?
C14F C15F 1.380(6) . ?
C14F C17F 1.490(6) . ?
C15F H15F 0.9500 . ?
C15F C16F 1.358(6) . ?
C16F H16F 0.9500 . ?
C17F H17J 0.9800 . ?
C17F H17K 0.9800 . ?
C17F H17L 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 116.9(4) . . ?
C5 N1 H1 125.0 . . ?
C5 N1 C9 109.9(4) . . ?
C9 N1 H1 125.0 . . ?
O1 C1 C2 113.9(4) . . ?
O1 C1 C6 124.5(5) . . ?
C6 C1 C2 121.6(4) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 117.9(4) . . ?
C3 C4 C8 134.8(4) . . ?
C5 C4 C8 107.3(4) . . ?
N1 C5 C4 107.3(4) . . ?
N1 C5 C6 128.4(4) . . ?
C6 C5 C4 124.2(4) . . ?
C1 C6 H6 122.1 . . ?
C5 C6 C1 115.8(4) . . ?
C5 C6 H6 122.1 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8 126.3 . . ?
C9 C8 C4 107.3(4) . . ?
C9 C8 H8 126.3 . . ?
N1 C9 C10 118.5(4) . . ?
C8 C9 N1 108.1(4) . . ?
C8 C9 C10 133.5(4) . . ?
O2 C10 C9 119.6(4) . . ?
O2 C10 C11 118.8(4) . . ?
C9 C10 C11 121.7(4) . . ?
C12 C11 C10 124.1(4) . . ?
C16 C11 C10 117.7(4) . . ?
C16 C11 C12 118.2(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 118.5 . . ?
C12 C13 C14 123.1(4) . . ?
C14 C13 H13 118.5 . . ?
C13 C14 C17 121.6(4) . . ?
C15 C14 C13 116.2(4) . . ?
C15 C14 C17 122.2(4) . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C11 C16 C15 120.2(5) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1B O1B C7B 117.8(4) . . ?
C5B N1B H1B 124.9 . . ?
C5B N1B C9B 110.3(4) . . ?
C9B N1B H1B 124.9 . . ?
O1B C1B C2B 115.2(4) . . ?
O1B C1B C6B 123.2(4) . . ?
C6B C1B C2B 121.6(4) . . ?
C1B C2B H2B 119.3 . . ?
C3B C2B C1B 121.5(4) . . ?
C3B C2B H2B 119.3 . . ?
C2B C3B H3B 120.0 . . ?
C2B C3B C4B 120.1(4) . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B C5B 116.9(4) . . ?
C3B C4B C8B 135.8(5) . . ?
C5B C4B C8B 107.3(4) . . ?
N1B C5B C4B 107.1(4) . . ?
N1B C5B C6B 128.7(4) . . ?
C6B C5B C4B 124.2(4) . . ?
C1B C6B C5B 115.7(4) . . ?
C1B C6B H6B 122.2 . . ?
C5B C6B H6B 122.2 . . ?
O1B C7B H7BA 109.5 . . ?
O1B C7B H7BB 109.5 . . ?
O1B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C4B C8B H8B 126.3 . . ?
C9B C8B C4B 107.4(4) . . ?
C9B C8B H8B 126.3 . . ?
N1B C9B C10B 119.6(4) . . ?
C8B C9B N1B 107.9(4) . . ?
C8B C9B C10B 132.4(4) . . ?
O2B C10B C9B 120.2(4) . . ?
O2B C10B C11B 119.1(4) . . ?
C9B C10B C11B 120.7(4) . . ?
C12B C11B C10B 122.2(4) . . ?
C16B C11B C10B 119.4(4) . . ?
C16B C11B C12B 118.3(4) . . ?
C11B C12B H12B 119.7 . . ?
C13B C12B C11B 120.5(4) . . ?
C13B C12B H12B 119.7 . . ?
C12B C13B H13B 119.6 . . ?
C14B C13B C12B 120.8(4) . . ?
C14B C13B H13B 119.6 . . ?
C13B C14B C15B 118.8(4) . . ?
C13B C14B C17B 120.9(4) . . ?
C15B C14B C17B 120.3(4) . . ?
C14B C15B H15B 119.5 . . ?
C16B C15B C14B 121.0(4) . . ?
C16B C15B H15B 119.5 . . ?
C11B C16B H16B 119.7 . . ?
C15B C16B C11B 120.6(4) . . ?
C15B C16B H16B 119.7 . . ?
C14B C17B H17D 109.5 . . ?
C14B C17B H17E 109.5 . . ?
C14B C17B H17F 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C1D O1D C7D 117.4(4) . . ?
C5D N1D H1D 125.1 . . ?
C5D N1D C9D 109.8(4) . . ?
C9D N1D H1D 125.1 . . ?
O1D C1D C2D 114.6(4) . . ?
O1D C1D C6D 123.2(4) . . ?
C6D C1D C2D 122.2(4) . . ?
C1D C2D H2D 118.8 . . ?
C3D C2D C1D 122.3(4) . . ?
C3D C2D H2D 118.8 . . ?
C2D C3D H3D 121.0 . . ?
C2D C3D C4D 117.9(4) . . ?
C4D C3D H3D 121.0 . . ?
C3D C4D C8D 134.4(4) . . ?
C5D C4D C3D 118.8(4) . . ?
C5D C4D C8D 106.8(4) . . ?
N1D C5D C4D 108.2(4) . . ?
N1D C5D C6D 128.9(4) . . ?
C6D C5D C4D 123.0(4) . . ?
C1D C6D C5D 115.8(4) . . ?
C1D C6D H6D 122.1 . . ?
C5D C6D H6D 122.1 . . ?
O1D C7D H7DA 109.5 . . ?
O1D C7D H7DB 109.5 . . ?
O1D C7D H7DC 109.5 . . ?
H7DA C7D H7DB 109.5 . . ?
H7DA C7D H7DC 109.5 . . ?
H7DB C7D H7DC 109.5 . . ?
C4D C8D H8D 126.5 . . ?
C9D C8D C4D 107.0(4) . . ?
C9D C8D H8D 126.5 . . ?
N1D C9D C8D 108.3(4) . . ?
N1D C9D C10D 118.7(4) . . ?
C8D C9D C10D 133.0(4) . . ?
O2D C10D C9D 119.1(4) . . ?
O2D C10D C11D 118.6(4) . . ?
C9D C10D C11D 122.3(4) . . ?
C12D C11D C10D 122.7(4) . . ?
C12D C11D C16D 118.0(4) . . ?
C16D C11D C10D 119.3(4) . . ?
C11D C12D H12D 120.4 . . ?
C13D C12D C11D 119.1(4) . . ?
C13D C12D H12D 120.4 . . ?
C12D C13D H13D 119.0 . . ?
C14D C13D C12D 122.0(4) . . ?
C14D C13D H13D 119.0 . . ?
C13D C14D C15D 118.3(4) . . ?
C13D C14D C17D 119.8(4) . . ?
C15D C14D C17D 121.9(4) . . ?
C14D C15D H15D 119.4 . . ?
C16D C15D C14D 121.1(5) . . ?
C16D C15D H15D 119.4 . . ?
C11D C16D H16D 119.3 . . ?
C15D C16D C11D 121.4(5) . . ?
C15D C16D H16D 119.3 . . ?
C14D C17D H17G 109.5 . . ?
C14D C17D H17H 109.5 . . ?
C14D C17D H17I 109.5 . . ?
H17G C17D H17H 109.5 . . ?
H17G C17D H17I 109.5 . . ?
H17H C17D H17I 109.5 . . ?
C1F O1F C7F 115.9(4) . . ?
C5F N1F H1F 125.3 . . ?
C9F N1F H1F 125.3 . . ?
C9F N1F C5F 109.4(4) . . ?
O1F C1F C2F 112.9(4) . . ?
C6F C1F O1F 124.9(5) . . ?
C6F C1F C2F 122.2(4) . . ?
C1F C2F H2F 119.2 . . ?
C3F C2F C1F 121.6(4) . . ?
C3F C2F H2F 119.2 . . ?
C2F C3F H3F 121.4 . . ?
C2F C3F C4F 117.3(4) . . ?
C4F C3F H3F 121.4 . . ?
C3F C4F C5F 119.8(4) . . ?
C3F C4F C8F 134.0(4) . . ?
C5F C4F C8F 106.2(4) . . ?
N1F C5F C4F 108.2(4) . . ?
N1F C5F C6F 129.4(4) . . ?
C6F C5F C4F 122.4(4) . . ?
C1F C6F C5F 116.7(4) . . ?
C1F C6F H6F 121.7 . . ?
C5F C6F H6F 121.7 . . ?
O1F C7F H7FA 109.5 . . ?
O1F C7F H7FB 109.5 . . ?
O1F C7F H7FC 109.5 . . ?
H7FA C7F H7FB 109.5 . . ?
H7FA C7F H7FC 109.5 . . ?
H7FB C7F H7FC 109.5 . . ?
C4F C8F H8F 126.5 . . ?
C9F C8F C4F 106.9(4) . . ?
C9F C8F H8F 126.5 . . ?
N1F C9F C8F 109.3(4) . . ?
N1F C9F C10F 119.7(4) . . ?
C8F C9F C10F 130.9(4) . . ?
O2F C10F C9F 120.7(4) . . ?
O2F C10F C11F 118.9(4) . . ?
C9F C10F C11F 120.4(4) . . ?
C12F C11F C10F 122.7(4) . . ?
C12F C11F C16F 118.4(4) . . ?
C16F C11F C10F 118.8(4) . . ?
C11F C12F H12F 119.8 . . ?
C11F C12F C13F 120.5(4) . . ?
C13F C12F H12F 119.8 . . ?
C12F C13F H13F 119.3 . . ?
C14F C13F C12F 121.3(4) . . ?
C14F C13F H13F 119.3 . . ?
C13F C14F C15F 117.5(4) . . ?
C13F C14F C17F 120.9(4) . . ?
C15F C14F C17F 121.6(4) . . ?
C14F C15F H15F 118.8 . . ?
C16F C15F C14F 122.4(4) . . ?
C16F C15F H15F 118.8 . . ?
C11F C16F H16F 120.1 . . ?
C15F C16F C11F 119.8(4) . . ?
C15F C16F H16F 120.1 . . ?
C14F C17F H17J 109.5 . . ?
C14F C17F H17K 109.5 . . ?
C14F C17F H17L 109.5 . . ?
H17J C17F H17K 109.5 . . ?
H17J C17F H17L 109.5 . . ?
H17K C17F H17L 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.9(4) . . . . ?
O1 C1 C6 C5 179.2(4) . . . . ?
O2 C10 C11 C12 147.2(4) . . . . ?
O2 C10 C11 C16 -30.2(5) . . . . ?
N1 C5 C6 C1 180.0(4) . . . . ?
N1 C9 C10 O2 -5.0(6) . . . . ?
N1 C9 C10 C11 175.8(3) . . . . ?
C1 C2 C3 C4 -1.3(6) . . . . ?
C2 C1 C6 C5 -0.5(6) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C2 C3 C4 C8 -179.0(4) . . . . ?
C3 C4 C5 N1 179.5(3) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C3 C4 C8 C9 179.6(5) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C4 C8 C9 N1 1.4(5) . . . . ?
C4 C8 C9 C10 -179.0(4) . . . . ?
C5 N1 C9 C8 -1.6(5) . . . . ?
C5 N1 C9 C10 178.7(3) . . . . ?
C5 C4 C8 C9 -0.7(5) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
C7 O1 C1 C2 176.1(4) . . . . ?
C7 O1 C1 C6 -3.6(6) . . . . ?
C8 C4 C5 N1 -0.3(4) . . . . ?
C8 C4 C5 C6 179.1(4) . . . . ?
C8 C9 C10 O2 175.4(5) . . . . ?
C8 C9 C10 C11 -3.8(7) . . . . ?
C9 N1 C5 C4 1.2(4) . . . . ?
C9 N1 C5 C6 -178.2(4) . . . . ?
C9 C10 C11 C12 -33.6(6) . . . . ?
C9 C10 C11 C16 149.0(4) . . . . ?
C10 C11 C12 C13 -178.0(4) . . . . ?
C10 C11 C16 C15 179.0(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C12 C11 C16 C15 1.4(6) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C12 C13 C14 C17 178.7(4) . . . . ?
C13 C14 C15 C16 1.0(6) . . . . ?
C14 C15 C16 C11 -1.7(6) . . . . ?
C16 C11 C12 C13 -0.6(6) . . . . ?
C17 C14 C15 C16 -177.9(4) . . . . ?
O1B C1B C2B C3B 179.7(4) . . . . ?
O1B C1B C6B C5B 179.9(4) . . . . ?
O2B C10B C11B C12B 144.9(4) . . . . ?
O2B C10B C11B C16B -31.7(5) . . . . ?
N1B C5B C6B C1B 178.6(4) . . . . ?
N1B C9B C10B O2B -9.7(6) . . . . ?
N1B C9B C10B C11B 172.3(3) . . . . ?
C1B C2B C3B C4B 0.1(6) . . . . ?
C2B C1B C6B C5B 0.3(6) . . . . ?
C2B C3B C4B C5B 0.6(6) . . . . ?
C2B C3B C4B C8B -179.5(4) . . . . ?
C3B C4B C5B N1B -179.4(3) . . . . ?
C3B C4B C5B C6B -0.9(6) . . . . ?
C3B C4B C8B C9B -180.0(5) . . . . ?
C4B C5B C6B C1B 0.4(6) . . . . ?
C4B C8B C9B N1B -0.5(5) . . . . ?
C4B C8B C9B C10B -175.9(4) . . . . ?
C5B N1B C9B C8B 1.0(5) . . . . ?
C5B N1B C9B C10B 177.0(3) . . . . ?
C5B C4B C8B C9B -0.1(5) . . . . ?
C6B C1B C2B C3B -0.6(7) . . . . ?
C7B O1B C1B C2B -177.8(4) . . . . ?
C7B O1B C1B C6B 2.6(6) . . . . ?
C8B C4B C5B N1B 0.6(4) . . . . ?
C8B C4B C5B C6B 179.2(4) . . . . ?
C8B C9B C10B O2B 165.2(5) . . . . ?
C8B C9B C10B C11B -12.8(7) . . . . ?
C9B N1B C5B C4B -1.0(5) . . . . ?
C9B N1B C5B C6B -179.4(4) . . . . ?
C9B C10B C11B C12B -37.1(6) . . . . ?
C9B C10B C11B C16B 146.3(4) . . . . ?
C10B C11B C12B C13B -177.1(4) . . . . ?
C10B C11B C16B C15B 178.6(4) . . . . ?
C11B C12B C13B C14B -1.2(6) . . . . ?
C12B C11B C16B C15B 1.9(6) . . . . ?
C12B C13B C14B C15B 1.4(6) . . . . ?
C12B C13B C14B C17B 179.7(4) . . . . ?
C13B C14B C15B C16B 0.0(6) . . . . ?
C14B C15B C16B C11B -1.7(7) . . . . ?
C16B C11B C12B C13B -0.5(6) . . . . ?
C17B C14B C15B C16B -178.3(4) . . . . ?
O1D C1D C2D C3D -178.5(3) . . . . ?
O1D C1D C6D C5D 179.0(3) . . . . ?
O2D C10D C11D C12D 149.2(4) . . . . ?
O2D C10D C11D C16D -28.2(6) . . . . ?
N1D C5D C6D C1D -179.6(4) . . . . ?
N1D C9D C10D O2D -3.9(6) . . . . ?
N1D C9D C10D C11D 177.5(3) . . . . ?
C1D C2D C3D C4D -1.2(6) . . . . ?
C2D C1D C6D C5D -1.2(6) . . . . ?
C2D C3D C4D C5D 0.3(6) . . . . ?
C2D C3D C4D C8D 179.9(4) . . . . ?
C3D C4D C5D N1D -179.9(3) . . . . ?
C3D C4D C5D C6D 0.1(6) . . . . ?
C3D C4D C8D C9D -179.2(5) . . . . ?
C4D C5D C6D C1D 0.3(6) . . . . ?
C4D C8D C9D N1D -1.1(5) . . . . ?
C4D C8D C9D C10D -179.2(4) . . . . ?
C5D N1D C9D C8D 1.4(5) . . . . ?
C5D N1D C9D C10D 179.8(3) . . . . ?
C5D C4D C8D C9D 0.4(5) . . . . ?
C6D C1D C2D C3D 1.7(7) . . . . ?
C7D O1D C1D C2D 170.0(4) . . . . ?
C7D O1D C1D C6D -10.2(6) . . . . ?
C8D C4D C5D N1D 0.4(5) . . . . ?
C8D C4D C5D C6D -179.6(4) . . . . ?
C8D C9D C10D O2D 174.1(5) . . . . ?
C8D C9D C10D C11D -4.6(8) . . . . ?
C9D N1D C5D C4D -1.1(5) . . . . ?
C9D N1D C5D C6D 178.9(4) . . . . ?
C9D C10D C11D C12D -32.1(6) . . . . ?
C9D C10D C11D C16D 150.5(4) . . . . ?
C10D C11D C12D C13D -178.1(4) . . . . ?
C10D C11D C16D C15D 178.6(4) . . . . ?
C11D C12D C13D C14D 0.2(6) . . . . ?
C12D C11D C16D C15D 1.1(6) . . . . ?
C12D C13D C14D C15D 0.0(6) . . . . ?
C12D C13D C14D C17D 178.3(4) . . . . ?
C13D C14D C15D C16D 0.4(6) . . . . ?
C14D C15D C16D C11D -1.0(6) . . . . ?
C16D C11D C12D C13D -0.7(6) . . . . ?
C17D C14D C15D C16D -177.9(4) . . . . ?
O1F C1F C2F C3F -179.8(4) . . . . ?
O1F C1F C6F C5F 179.6(4) . . . . ?
O2F C10F C11F C12F 147.3(4) . . . . ?
O2F C10F C11F C16F -30.1(6) . . . . ?
N1F C5F C6F C1F 177.4(4) . . . . ?
N1F C9F C10F O2F -12.1(6) . . . . ?
N1F C9F C10F C11F 170.7(3) . . . . ?
C1F C2F C3F C4F 0.3(6) . . . . ?
C2F C1F C6F C5F 0.2(6) . . . . ?
C2F C3F C4F C5F -0.1(6) . . . . ?
C2F C3F C4F C8F -179.0(4) . . . . ?
C3F C4F C5F N1F -177.9(4) . . . . ?
C3F C4F C5F C6F 0.0(6) . . . . ?
C3F C4F C8F C9F 178.1(5) . . . . ?
C4F C5F C6F C1F 0.0(6) . . . . ?
C4F C8F C9F N1F 0.2(5) . . . . ?
C4F C8F C9F C10F -175.7(4) . . . . ?
C5F N1F C9F C8F 0.6(5) . . . . ?
C5F N1F C9F C10F 177.0(4) . . . . ?
C5F C4F C8F C9F -0.9(5) . . . . ?
C6F C1F C2F C3F -0.3(7) . . . . ?
C7F O1F C1F C2F 179.8(4) . . . . ?
C7F O1F C1F C6F 0.4(6) . . . . ?
C8F C4F C5F N1F 1.2(5) . . . . ?
C8F C4F C5F C6F 179.1(4) . . . . ?
C8F C9F C10F O2F 163.5(5) . . . . ?
C8F C9F C10F C11F -13.8(7) . . . . ?
C9F N1F C5F C4F -1.1(5) . . . . ?
C9F N1F C5F C6F -178.8(4) . . . . ?
C9F C10F C11F C12F -35.4(6) . . . . ?
C9F C10F C11F C16F 147.1(4) . . . . ?
C10F C11F C12F C13F -178.4(4) . . . . ?
C10F C11F C16F C15F -179.4(4) . . . . ?
C11F C12F C13F C14F -2.0(6) . . . . ?
C12F C11F C16F C15F 3.0(6) . . . . ?
C12F C13F C14F C15F 2.9(6) . . . . ?
C12F C13F C14F C17F -178.6(4) . . . . ?
C13F C14F C15F C16F -0.8(7) . . . . ?
C14F C15F C16F C11F -2.2(7) . . . . ?
C16F C11F C12F C13F -1.0(6) . . . . ?
C17F C14F C15F C16F -179.3(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5340(14)
2 0.4660(14)
# End of CIF  ============================================================
####################################################################### 
# 
# 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_cham19
_database_code_depnum_ccdc_archive 'CCDC 1482068'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_audit_creation_date             2015-12-19
_audit_creation_method           
#==========================================================================

# SUBMISSION DETAILS
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014-3
#==========================================================================
# CHEMICAL DATA
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H20 Cl N O3'
_chemical_formula_sum            'C26 H20 Cl N O3'
_chemical_formula_weight         429.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#==========================================================================

# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3875(4)
_cell_length_b                   11.6702(6)
_cell_length_c                   13.4944(7)
_cell_angle_alpha                64.6470(10)
_cell_angle_beta                 82.9110(10)
_cell_angle_gamma                77.6900(10)
_cell_volume                     1026.50(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      36.342
_cell_measurement_theta_min      2.824
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
#==========================================================================

# Experimental data 
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1157 before and 0.0365 after correction.
The Ratio of minimum to maximum transmission is 0.9521.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            55806
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.399
_diffrn_reflns_theta_min         2.824
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9095
_reflns_number_total             9907
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         9907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.037
_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)+(0.0469P)²+0.2986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0913
#==========================================================================

# Refinement data 
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.10466(2) 0.90205(2) 0.11974(2) 0.01862(4) Uani 1 1 d . . . . .
O1 O 0.85982(7) 0.53449(5) 0.33864(4) 0.01661(9) Uani 1 1 d . . . . .
O2 O 1.24354(7) 0.32732(5) -0.01279(4) 0.01531(8) Uani 1 1 d . . . . .
O3 O 1.07758(6) 0.22600(5) 0.48568(4) 0.01561(9) Uani 1 1 d . . . . .
N1 N 0.45461(7) 0.28834(5) 0.48636(4) 0.01088(8) Uani 1 1 d . . . . .
H1 H 0.3352 0.2893 0.5021 0.013 Uiso 1 1 calc R . . . .
C1 C 0.52945(8) 0.38807(5) 0.40386(5) 0.01012(8) Uani 1 1 d . . . . .
C2 C 0.71924(8) 0.35076(5) 0.40536(5) 0.01005(8) Uani 1 1 d . . . . .
C3 C 0.76148(8) 0.22398(5) 0.49174(5) 0.01014(8) Uani 1 1 d . . . . .
C4 C 0.59130(8) 0.18825(5) 0.53997(5) 0.01033(9) Uani 1 1 d . . . . .
C5 C 0.41762(8) 0.51005(5) 0.33359(5) 0.01014(8) Uani 1 1 d . . . . .
C6 C 0.25677(8) 0.56556(6) 0.37486(5) 0.01149(9) Uani 1 1 d . . . . .
H6 H 0.2149 0.5214 0.4485 0.014 Uiso 1 1 calc R . . . .
C7 C 0.15768(8) 0.68520(6) 0.30855(5) 0.01261(9) Uani 1 1 d . . . . .
H7 H 0.0471 0.7221 0.3360 0.015 Uiso 1 1 calc R . . . .
C8 C 0.22254(9) 0.74975(6) 0.20196(5) 0.01259(9) Uani 1 1 d . . . . .
C9 C 0.37933(9) 0.69560(6) 0.15797(5) 0.01335(9) Uani 1 1 d . . . . .
H9 H 0.4200 0.7401 0.0841 0.016 Uiso 1 1 calc R . . . .
C10 C 0.47533(8) 0.57530(6) 0.22387(5) 0.01228(9) Uani 1 1 d . . . . .
H10 H 0.5814 0.5366 0.1944 0.015 Uiso 1 1 calc R . . . .
C11 C 0.85167(8) 0.43423(6) 0.33213(5) 0.01101(9) Uani 1 1 d . . . . .
C12 C 0.95884(8) 0.39774(5) 0.24640(5) 0.01048(9) Uani 1 1 d . . . . .
C13 C 1.09651(8) 0.46714(6) 0.18278(5) 0.01183(9) Uani 1 1 d . . . . .
H13 H 1.1254 0.5332 0.1982 0.014 Uiso 1 1 calc R . . . .
C14 C 1.19052(8) 0.44041(6) 0.09795(5) 0.01264(9) Uani 1 1 d . . . . .
H14 H 1.2842 0.4875 0.0557 0.015 Uiso 1 1 calc R . . . .
C15 C 1.14743(8) 0.34371(6) 0.07427(5) 0.01156(9) Uani 1 1 d . . . . .
C16 C 1.01298(9) 0.27237(6) 0.13781(5) 0.01323(9) Uani 1 1 d . . . . .
H16 H 0.9853 0.2055 0.1229 0.016 Uiso 1 1 calc R . . . .
C17 C 0.91979(8) 0.30021(6) 0.22331(5) 0.01233(9) Uani 1 1 d . . . . .
H17 H 0.8280 0.2519 0.2666 0.015 Uiso 1 1 calc R . . . .
C18 C 1.18882(11) 0.23947(7) -0.04632(6) 0.02025(12) Uani 1 1 d . . . . .
H18A H 1.2505 0.2475 -0.1170 0.030 Uiso 1 1 calc GR . . . .
H18B H 1.0541 0.2594 -0.0538 0.030 Uiso 1 1 calc GR . . . .
H18C H 1.2243 0.1512 0.0088 0.030 Uiso 1 1 calc GR . . . .
C19 C 0.95016(8) 0.16536(6) 0.52984(5) 0.01151(9) Uani 1 1 d . . . . .
C20 C 0.98931(9) 0.03497(6) 0.62393(6) 0.01615(10) Uani 1 1 d . . . . .
H20A H 0.9628 -0.0304 0.6031 0.024 Uiso 1 1 calc GR . . . .
H20B H 0.9107 0.0352 0.6879 0.024 Uiso 1 1 calc GR . . . .
H20C H 1.1200 0.0150 0.6422 0.024 Uiso 1 1 calc GR . . . .
C21 C 0.54090(8) 0.07352(6) 0.63353(5) 0.01105(9) Uani 1 1 d . . . . .
C22 C 0.58554(9) -0.04821(6) 0.63174(5) 0.01391(10) Uani 1 1 d . . . . .
H22 H 0.6505 -0.0580 0.5697 0.017 Uiso 1 1 calc R . . . .
C23 C 0.53519(10) -0.15509(6) 0.72043(6) 0.01775(11) Uani 1 1 d . . . . .
H23 H 0.5653 -0.2375 0.7187 0.021 Uiso 1 1 calc R . . . .
C24 C 0.44080(10) -0.14135(7) 0.81169(6) 0.01943(12) Uani 1 1 d . . . . .
H24 H 0.4077 -0.2146 0.8725 0.023 Uiso 1 1 calc R . . . .
C25 C 0.39485(10) -0.02054(7) 0.81390(6) 0.01971(12) Uani 1 1 d . . . . .
H25 H 0.3302 -0.0113 0.8762 0.024 Uiso 1 1 calc R . . . .
C26 C 0.44366(9) 0.08713(7) 0.72473(5) 0.01600(10) Uani 1 1 d . . . . .
H26 H 0.4108 0.1698 0.7260 0.019 Uiso 1 1 calc R . . . .

#==========================================================================

# 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
Cl1 C8 1.7430(6) . ?
O1 C11 1.2247(7) . ?
O2 C15 1.3600(7) . ?
O2 C18 1.4277(9) . ?
O3 C19 1.2355(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.3830(7) . ?
N1 C4 1.3643(8) . ?
C1 C2 1.3766(8) . ?
C1 C5 1.4642(8) . ?
C2 C3 1.4356(8) . ?
C2 C11 1.4919(8) . ?
C3 C4 1.4026(8) . ?
C3 C19 1.4644(8) . ?
C4 C21 1.4745(8) . ?
C5 C6 1.3996(8) . ?
C5 C10 1.4040(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.3935(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.3863(9) . ?
C8 C9 1.3903(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.3881(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.4828(8) . ?
C12 C13 1.4027(8) . ?
C12 C17 1.3935(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.3811(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.4014(8) . ?
C15 C16 1.3950(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.3930(8) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.5032(9) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.3983(9) . ?
C21 C26 1.3987(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.3915(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.3921(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.3904(11) . ?
C25 H25 0.9500 . ?
C25 C26 1.3957(10) . ?
C26 H26 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
C15 O2 C18 116.74(5) . . ?
C1 N1 H1 124.7 . . ?
C4 N1 H1 124.7 . . ?
C4 N1 C1 110.66(5) . . ?
N1 C1 C5 123.45(5) . . ?
C2 C1 N1 107.39(5) . . ?
C2 C1 C5 129.14(5) . . ?
C1 C2 C3 107.87(5) . . ?
C1 C2 C11 124.12(5) . . ?
C3 C2 C11 127.93(5) . . ?
C2 C3 C19 122.01(5) . . ?
C4 C3 C2 106.62(5) . . ?
C4 C3 C19 130.11(5) . . ?
N1 C4 C3 107.46(5) . . ?
N1 C4 C21 119.27(5) . . ?
C3 C4 C21 133.20(5) . . ?
C6 C5 C1 121.14(5) . . ?
C6 C5 C10 119.06(5) . . ?
C10 C5 C1 119.76(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.40(5) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.17(5) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 Cl1 119.66(5) . . ?
C7 C8 C9 121.65(5) . . ?
C9 C8 Cl1 118.69(5) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.81(6) . . ?
C10 C9 H9 120.6 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.83(5) . . ?
C9 C10 H10 119.6 . . ?
O1 C11 C2 119.99(5) . . ?
O1 C11 C12 121.76(5) . . ?
C12 C11 C2 118.04(5) . . ?
C13 C12 C11 119.50(5) . . ?
C17 C12 C11 121.58(5) . . ?
C17 C12 C13 118.83(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.70(5) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.88(5) . . ?
C15 C14 H14 120.1 . . ?
O2 C15 C14 115.46(5) . . ?
O2 C15 C16 124.37(5) . . ?
C16 C15 C14 120.17(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.25(5) . . ?
C17 C16 H16 120.4 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.14(5) . . ?
C16 C17 H17 119.4 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 C3 119.18(5) . . ?
O3 C19 C20 119.83(5) . . ?
C3 C19 C20 120.96(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C4 121.13(5) . . ?
C22 C21 C26 119.45(5) . . ?
C26 C21 C4 119.42(5) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.24(6) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.08(6) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.06(6) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.06(6) . . ?
C26 C25 H25 120.0 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.10(6) . . ?
C25 C26 H26 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.88 2.25 3.0271(7) 147.1 1_455

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
Cl1 C8 C9 C10 178.88(5) . . . . ?
O1 C11 C12 C13 11.02(9) . . . . ?
O1 C11 C12 C17 -165.57(6) . . . . ?
O2 C15 C16 C17 -178.24(6) . . . . ?
N1 C1 C2 C3 -0.02(6) . . . . ?
N1 C1 C2 C11 -177.02(5) . . . . ?
N1 C1 C5 C6 35.66(9) . . . . ?
N1 C1 C5 C10 -146.61(6) . . . . ?
N1 C4 C21 C22 119.58(6) . . . . ?
N1 C4 C21 C26 -59.18(8) . . . . ?
C1 N1 C4 C3 0.57(7) . . . . ?
C1 N1 C4 C21 178.05(5) . . . . ?
C1 C2 C3 C4 0.36(6) . . . . ?
C1 C2 C3 C19 -168.03(5) . . . . ?
C1 C2 C11 O1 63.32(8) . . . . ?
C1 C2 C11 C12 -111.51(7) . . . . ?
C1 C5 C6 C7 176.38(5) . . . . ?
C1 C5 C10 C9 -175.17(6) . . . . ?
C2 C1 C5 C6 -142.07(6) . . . . ?
C2 C1 C5 C10 35.67(9) . . . . ?
C2 C3 C4 N1 -0.56(6) . . . . ?
C2 C3 C4 C21 -177.54(6) . . . . ?
C2 C3 C19 O3 -0.81(9) . . . . ?
C2 C3 C19 C20 177.15(6) . . . . ?
C2 C11 C12 C13 -174.24(5) . . . . ?
C2 C11 C12 C17 9.17(8) . . . . ?
C3 C2 C11 O1 -113.06(7) . . . . ?
C3 C2 C11 C12 72.11(8) . . . . ?
C3 C4 C21 C22 -63.72(9) . . . . ?
C3 C4 C21 C26 117.52(8) . . . . ?
C4 N1 C1 C2 -0.34(7) . . . . ?
C4 N1 C1 C5 -178.49(5) . . . . ?
C4 C3 C19 O3 -166.21(6) . . . . ?
C4 C3 C19 C20 11.75(10) . . . . ?
C4 C21 C22 C23 -179.39(6) . . . . ?
C4 C21 C26 C25 179.96(6) . . . . ?
C5 C1 C2 C3 177.99(6) . . . . ?
C5 C1 C2 C11 0.99(10) . . . . ?
C5 C6 C7 C8 -1.33(9) . . . . ?
C6 C5 C10 C9 2.61(9) . . . . ?
C6 C7 C8 Cl1 -177.67(5) . . . . ?
C6 C7 C8 C9 2.92(9) . . . . ?
C7 C8 C9 C10 -1.71(9) . . . . ?
C8 C9 C10 C5 -1.10(9) . . . . ?
C10 C5 C6 C7 -1.37(9) . . . . ?
C11 C2 C3 C4 177.21(6) . . . . ?
C11 C2 C3 C19 8.82(9) . . . . ?
C11 C12 C13 C14 -176.00(6) . . . . ?
C11 C12 C17 C16 175.72(6) . . . . ?
C12 C13 C14 C15 0.51(9) . . . . ?
C13 C12 C17 C16 -0.90(9) . . . . ?
C13 C14 C15 O2 178.06(6) . . . . ?
C13 C14 C15 C16 -1.53(9) . . . . ?
C14 C15 C16 C17 1.32(9) . . . . ?
C15 C16 C17 C12 -0.10(9) . . . . ?
C17 C12 C13 C14 0.69(9) . . . . ?
C18 O2 C15 C14 -173.41(6) . . . . ?
C18 O2 C15 C16 6.17(9) . . . . ?
C19 C3 C4 N1 166.55(6) . . . . ?
C19 C3 C4 C21 -10.43(11) . . . . ?
C21 C22 C23 C24 -0.31(10) . . . . ?
C22 C21 C26 C25 1.18(10) . . . . ?
C22 C23 C24 C25 0.70(11) . . . . ?
C23 C24 C25 C26 -0.15(11) . . . . ?
C24 C25 C26 C21 -0.79(11) . . . . ?
C26 C21 C22 C23 -0.63(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
####################################################################### 
# 
# 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_cham2
_database_code_depnum_ccdc_archive 'CCDC 1482069'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_audit_creation_date             2015-12-19
_audit_creation_method           

#==========================================================================

# SUBMISSION DETAILS
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014-3
#==========================================================================
# CHEMICAL DATA
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C2 H6 O S, C21 H18 N2 O5'
_chemical_formula_sum            'C23 H24 N2 O6 S'
_chemical_formula_weight         456.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#==========================================================================

# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5455(4)
_cell_length_b                   12.0470(6)
_cell_length_c                   12.1501(6)
_cell_angle_alpha                60.7330(10)
_cell_angle_beta                 81.883(2)
_cell_angle_gamma                87.112(2)
_cell_volume                     1079.97(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9788
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      27.508
_cell_measurement_theta_min      2.883
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.6908
_exptl_absorpt_correction_T_min  0.4271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
#==========================================================================

# Experimental data 
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1639 before and 0.1181 after correction.
The Ratio of minimum to maximum transmission is 0.6183.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.394
_exptl_crystal_size_min          0.052
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42203
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.883
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4310
_reflns_number_total             4967
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.069
_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)+(0.0736P)²+0.5035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1296
#==========================================================================

# Refinement data 
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C4S(H4SA,H4SB,H4SC), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 
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
S1S S 0.65116(5) 0.40617(4) 0.88756(3) 0.01298(12) Uani 1 1 d . . . . .
O2S O 0.52602(15) 0.50458(11) 0.83177(11) 0.0189(3) Uani 1 1 d . . . . .
C3S C 0.7700(2) 0.46859(17) 0.95571(18) 0.0211(4) Uani 1 1 d . . . . .
H3SA H 0.8242 0.5471 0.8881 0.032 Uiso 1 1 calc GR . . . .
H3SB H 0.8484 0.4059 0.9996 0.032 Uiso 1 1 calc GR . . . .
H3SC H 0.7024 0.4870 1.0167 0.032 Uiso 1 1 calc GR . . . .
C4S C 0.55319(19) 0.28165(15) 1.03249(15) 0.0143(3) Uani 1 1 d . . . . .
H4SA H 0.4933 0.3182 1.0816 0.021 Uiso 1 1 calc GR . . . .
H4SB H 0.6317 0.2234 1.0822 0.021 Uiso 1 1 calc GR . . . .
H4SC H 0.4807 0.2349 1.0132 0.021 Uiso 1 1 calc GR . . . .
O1 O 0.98259(16) 0.19765(12) 0.54846(13) 0.0242(3) Uani 1 1 d . . . . .
O2 O 1.08370(18) 0.33123(14) 0.35633(14) 0.0325(3) Uani 1 1 d . . . . .
O3 O 0.52571(14) 0.79415(11) 0.17881(10) 0.0146(2) Uani 1 1 d . . . . .
O4 O 1.03981(13) 1.24085(11) -0.06907(11) 0.0155(2) Uani 1 1 d . . . . .
O5 O 0.36450(14) 1.02466(11) 0.22889(11) 0.0181(3) Uani 1 1 d . . . . .
N1 N 0.51347(15) 0.68289(13) 0.57691(12) 0.0115(3) Uani 1 1 d . . . . .
H1 H 0.5230 0.6197 0.6535 0.014 Uiso 1 1 calc R . . . .
N2 N 0.99258(17) 0.30386(14) 0.45423(14) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.59199(18) 0.69239(14) 0.46481(14) 0.0102(3) Uani 1 1 d . . . . .
C2 C 0.54516(17) 0.80324(14) 0.36635(14) 0.0091(3) Uani 1 1 d . . . . .
C3 C 0.43615(18) 0.86346(14) 0.42089(14) 0.0109(3) Uani 1 1 d . . . . .
C4 C 0.42018(18) 0.78407(15) 0.55263(15) 0.0119(3) Uani 1 1 d . . . . .
C5 C 0.69670(18) 0.59271(14) 0.46422(14) 0.0104(3) Uani 1 1 d . . . . .
C6 C 0.68187(18) 0.46778(15) 0.56643(14) 0.0118(3) Uani 1 1 d . . . . .
H6 H 0.6042 0.4478 0.6379 0.014 Uiso 1 1 calc R . . . .
C7 C 0.77926(18) 0.37326(15) 0.56421(15) 0.0127(3) Uani 1 1 d . . . . .
H7 H 0.7701 0.2891 0.6340 0.015 Uiso 1 1 calc R . . . .
C8 C 0.89053(18) 0.40370(15) 0.45818(15) 0.0130(3) Uani 1 1 d . . . . .
C9 C 0.90895(19) 0.52615(15) 0.35536(15) 0.0141(3) Uani 1 1 d . . . . .
H9 H 0.9861 0.5449 0.2838 0.017 Uiso 1 1 calc R . . . .
C10 C 0.81272(18) 0.62020(15) 0.35933(15) 0.0127(3) Uani 1 1 d . . . . .
H10 H 0.8251 0.7047 0.2902 0.015 Uiso 1 1 calc R . . . .
C11 C 0.58548(18) 0.84741(14) 0.22677(14) 0.0101(3) Uani 1 1 d . . . . .
C12 C 0.70440(17) 0.95266(14) 0.15158(14) 0.0097(3) Uani 1 1 d . . . . .
C13 C 0.80493(18) 0.98628(14) 0.21180(14) 0.0115(3) Uani 1 1 d . . . . .
H13 H 0.7944 0.9437 0.3021 0.014 Uiso 1 1 calc R . . . .
C14 C 0.92071(18) 1.08139(15) 0.14162(15) 0.0124(3) Uani 1 1 d . . . . .
H14 H 0.9898 1.1030 0.1834 0.015 Uiso 1 1 calc R . . . .
C15 C 0.93363(18) 1.14427(14) 0.00939(15) 0.0114(3) Uani 1 1 d . . . . .
C16 C 0.83329(18) 1.11140(14) -0.05241(14) 0.0117(3) Uani 1 1 d . . . . .
H16 H 0.8427 1.1549 -0.1427 0.014 Uiso 1 1 calc R . . . .
C17 C 0.72081(18) 1.01572(14) 0.01821(14) 0.0107(3) Uani 1 1 d . . . . .
H17 H 0.6540 0.9924 -0.0237 0.013 Uiso 1 1 calc R . . . .
C18 C 1.1548(2) 1.26980(16) -0.01167(17) 0.0187(3) Uani 1 1 d . . . . .
H18A H 1.2283 1.3360 -0.0782 0.028 Uiso 1 1 calc GR . . . .
H18B H 1.2134 1.1930 0.0374 0.028 Uiso 1 1 calc GR . . . .
H18C H 1.1016 1.3003 0.0451 0.028 Uiso 1 1 calc GR . . . .
C19 C 0.35301(18) 0.97987(15) 0.34459(15) 0.0126(3) Uani 1 1 d . . . . .
C20 C 0.2544(2) 1.04545(17) 0.40851(17) 0.0210(4) Uani 1 1 d . . . . .
H20A H 0.2268 1.1302 0.3438 0.031 Uiso 1 1 calc GR . . . .
H20B H 0.3150 1.0535 0.4671 0.031 Uiso 1 1 calc GR . . . .
H20C H 0.1575 0.9951 0.4561 0.031 Uiso 1 1 calc GR . . . .
C21 C 0.3226(2) 0.79246(17) 0.66087(15) 0.0181(3) Uani 1 1 d . . . . .
H21A H 0.3296 0.7128 0.7402 0.027 Uiso 1 1 calc GR . . . .
H21B H 0.2121 0.8068 0.6451 0.027 Uiso 1 1 calc GR . . . .
H21C H 0.3623 0.8633 0.6681 0.027 Uiso 1 1 calc GR . . . .

#==========================================================================

# 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
S1S O2S 1.5166(12) . ?
S1S C3S 1.7905(18) . ?
S1S C4S 1.7830(17) . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
O1 N2 1.2273(19) . ?
O2 N2 1.229(2) . ?
O3 C11 1.2226(19) . ?
O4 C15 1.3651(18) . ?
O4 C18 1.428(2) . ?
O5 C19 1.225(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.3842(19) . ?
N1 C4 1.351(2) . ?
N2 C8 1.466(2) . ?
C1 C2 1.376(2) . ?
C1 C5 1.463(2) . ?
C2 C3 1.436(2) . ?
C2 C11 1.500(2) . ?
C3 C4 1.396(2) . ?
C3 C19 1.465(2) . ?
C4 C21 1.499(2) . ?
C5 C6 1.404(2) . ?
C5 C10 1.407(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.487(2) . ?
C12 C13 1.393(2) . ?
C12 C17 1.402(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(2) . ?
C15 C16 1.401(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.512(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2S S1S C3S 105.53(8) . . ?
O2S S1S C4S 105.31(7) . . ?
C4S S1S C3S 97.81(8) . . ?
S1S C3S H3SA 109.5 . . ?
S1S C3S H3SB 109.5 . . ?
S1S C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
S1S C4S H4SA 109.5 . . ?
S1S C4S H4SB 109.5 . . ?
S1S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
C15 O4 C18 117.41(13) . . ?
C1 N1 H1 124.7 . . ?
C4 N1 H1 124.7 . . ?
C4 N1 C1 110.66(13) . . ?
O1 N2 O2 123.52(15) . . ?
O1 N2 C8 118.45(14) . . ?
O2 N2 C8 118.04(14) . . ?
N1 C1 C5 121.68(13) . . ?
C2 C1 N1 107.22(13) . . ?
C2 C1 C5 131.03(14) . . ?
C1 C2 C3 107.68(13) . . ?
C1 C2 C11 126.69(13) . . ?
C3 C2 C11 125.33(13) . . ?
C2 C3 C19 123.29(14) . . ?
C4 C3 C2 106.47(13) . . ?
C4 C3 C19 130.03(14) . . ?
N1 C4 C3 107.97(13) . . ?
N1 C4 C21 119.61(14) . . ?
C3 C4 C21 132.42(14) . . ?
C6 C5 C1 121.00(14) . . ?
C6 C5 C10 118.70(14) . . ?
C10 C5 C1 120.29(14) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.74(15) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.83(14) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 N2 119.20(14) . . ?
C7 C8 C9 122.12(14) . . ?
C9 C8 N2 118.68(14) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.59(15) . . ?
C10 C9 H9 120.7 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 121.01(14) . . ?
C9 C10 H10 119.5 . . ?
O3 C11 C2 120.13(13) . . ?
O3 C11 C12 121.81(14) . . ?
C12 C11 C2 118.00(13) . . ?
C13 C12 C11 120.81(13) . . ?
C13 C12 C17 119.21(14) . . ?
C17 C12 C11 119.92(13) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.03(14) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.94(14) . . ?
C15 C14 H14 120.5 . . ?
O4 C15 C14 124.17(14) . . ?
O4 C15 C16 115.21(13) . . ?
C14 C15 C16 120.61(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.82(14) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.36(14) . . ?
C16 C17 H17 119.8 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 C3 120.01(14) . . ?
O5 C19 C20 120.04(15) . . ?
C3 C19 C20 119.95(14) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C21 H21A 109.5 . . ?
C4 C21 H21B 109.5 . . ?
C4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2S 0.88 1.92 2.7895(17) 168.6 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C8 C7 -4.2(2) . . . . ?
O1 N2 C8 C9 175.61(15) . . . . ?
O2 N2 C8 C7 175.75(15) . . . . ?
O2 N2 C8 C9 -4.4(2) . . . . ?
O3 C11 C12 C13 -160.55(15) . . . . ?
O3 C11 C12 C17 16.7(2) . . . . ?
O4 C15 C16 C17 -179.46(13) . . . . ?
N1 C1 C2 C3 0.69(16) . . . . ?
N1 C1 C2 C11 -173.19(14) . . . . ?
N1 C1 C5 C6 22.2(2) . . . . ?
N1 C1 C5 C10 -159.05(14) . . . . ?
N2 C8 C9 C10 -179.92(14) . . . . ?
C1 N1 C4 C3 0.11(18) . . . . ?
C1 N1 C4 C21 179.32(14) . . . . ?
C1 C2 C3 C4 -0.63(17) . . . . ?
C1 C2 C3 C19 -175.82(14) . . . . ?
C1 C2 C11 O3 71.6(2) . . . . ?
C1 C2 C11 C12 -105.63(18) . . . . ?
C1 C5 C6 C7 178.70(14) . . . . ?
C1 C5 C10 C9 -177.76(14) . . . . ?
C2 C1 C5 C6 -154.50(16) . . . . ?
C2 C1 C5 C10 24.3(2) . . . . ?
C2 C3 C4 N1 0.31(17) . . . . ?
C2 C3 C4 C21 -178.76(17) . . . . ?
C2 C3 C19 O5 6.2(2) . . . . ?
C2 C3 C19 C20 -173.13(15) . . . . ?
C2 C11 C12 C13 16.7(2) . . . . ?
C2 C11 C12 C17 -166.04(13) . . . . ?
C3 C2 C11 O3 -101.20(18) . . . . ?
C3 C2 C11 C12 81.52(19) . . . . ?
C4 N1 C1 C2 -0.51(17) . . . . ?
C4 N1 C1 C5 -177.89(13) . . . . ?
C4 C3 C19 O5 -167.74(16) . . . . ?
C4 C3 C19 C20 12.9(3) . . . . ?
C5 C1 C2 C3 177.74(15) . . . . ?
C5 C1 C2 C11 3.9(3) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C5 C10 C9 1.0(2) . . . . ?
C6 C7 C8 N2 -179.14(14) . . . . ?
C6 C7 C8 C9 1.1(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C5 -0.9(2) . . . . ?
C10 C5 C6 C7 -0.1(2) . . . . ?
C11 C2 C3 C4 173.36(14) . . . . ?
C11 C2 C3 C19 -1.8(2) . . . . ?
C11 C12 C13 C14 177.43(14) . . . . ?
C11 C12 C17 C16 -178.46(13) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C12 C17 C16 -1.1(2) . . . . ?
C13 C14 C15 O4 178.41(14) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C15 C16 C17 C12 1.1(2) . . . . ?
C17 C12 C13 C14 0.1(2) . . . . ?
C18 O4 C15 C14 6.6(2) . . . . ?
C18 O4 C15 C16 -174.09(13) . . . . ?
C19 C3 C4 N1 175.06(15) . . . . ?
C19 C3 C4 C21 -4.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
