# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1837694'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 N O2'
_chemical_formula_weight         261.27

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.812(2)
_cell_length_b                   15.260(3)
_cell_length_c                   18.464(4)
_cell_angle_alpha                108.25(3)
_cell_angle_beta                 98.59(3)
_cell_angle_gamma                92.69(3)
_cell_volume                     2583.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4815
_cell_measurement_theta_min      1.5183
_cell_measurement_theta_max      27.8426

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8150
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            31307
_diffrn_reflns_av_unetI/netI     0.1057
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.412
_diffrn_reflns_theta_max         27.864
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12234
_reflns_number_gt                6515
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0107(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12234
_refine_ls_number_parameters     722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_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
O1 O 0.49753(16) 0.84150(10) 1.02034(8) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.68686(17) 0.84291(11) 1.10201(9) 0.0397(4) Uani 1 1 d . . . . .
O3 O -0.10152(18) 0.39833(10) 0.16695(9) 0.0372(4) Uani 1 1 d . . . . .
O4 O 0.0700(2) 0.32835(11) 0.20859(10) 0.0478(5) Uani 1 1 d . . . . .
O5 O 0.33785(16) 0.90537(10) 0.42255(9) 0.0329(4) Uani 1 1 d . . . . .
O6 O 0.33724(17) 0.78007(11) 0.45776(10) 0.0428(4) Uani 1 1 d . . . . .
O7 O -0.13498(16) 0.56179(10) 0.58180(9) 0.0345(4) Uani 1 1 d . . . . .
O8 O -0.16548(18) 0.67852(12) 0.53661(10) 0.0467(5) Uani 1 1 d . . . . .
N1 N 0.9849(3) 0.74962(17) 0.99393(14) 0.0589(7) Uani 1 1 d . . . . .
N2 N 0.3784(2) 0.32549(16) 0.08453(14) 0.0578(7) Uani 1 1 d . . . . .
N3 N 0.4760(3) 0.58448(16) 0.35357(15) 0.0602(7) Uani 1 1 d . . . . .
N4 N 0.0407(3) 0.89670(16) 0.63019(14) 0.0581(7) Uani 1 1 d . . . . .
C1 C 0.4324(2) 0.85876(15) 0.95560(12) 0.0280(5) Uani 1 1 d . . . . .
C2 C 0.2906(2) 0.83345(16) 0.93564(13) 0.0343(6) Uani 1 1 d . . . . .
H2 H 0.2439 0.8037 0.9644 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2192(3) 0.85249(16) 0.87311(14) 0.0389(6) Uani 1 1 d . . . . .
H3 H 0.1224 0.8347 0.8580 0.047 Uiso 1 1 calc R U . . .
C4 C 0.2870(3) 0.89729(16) 0.83204(14) 0.0387(6) Uani 1 1 d . . . . .
H4 H 0.2356 0.9132 0.7909 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4293(2) 0.91898(15) 0.85069(13) 0.0319(5) Uani 1 1 d . . . . .
H5 H 0.4753 0.9475 0.8209 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5059(2) 0.89922(14) 0.91307(12) 0.0254(5) Uani 1 1 d . . . . .
C7 C 0.6559(2) 0.91363(14) 0.93344(12) 0.0253(5) Uani 1 1 d . . . . .
C8 C 0.7183(2) 0.89390(15) 0.99623(12) 0.0273(5) Uani 1 1 d . . . . .
C9 C 0.6384(2) 0.85833(15) 1.04347(13) 0.0304(5) Uani 1 1 d . . . . .
C10 C 0.8718(2) 0.90638(16) 1.02388(14) 0.0347(6) Uani 1 1 d . . . . .
H10A H 0.9157 0.9458 0.9985 0.042 Uiso 1 1 calc R U . . .
H10B H 0.8909 0.9393 1.0804 0.042 Uiso 1 1 calc R U . . .
C11 C 0.9350(3) 0.81813(19) 1.00780(14) 0.0387(6) Uani 1 1 d . . . . .
C12 C 0.7380(2) 0.94222(15) 0.88114(12) 0.0269(5) Uani 1 1 d . . . . .
C13 C 0.7401(2) 1.03039(15) 0.87441(12) 0.0312(5) Uani 1 1 d . . . . .
H13 H 0.6864 1.0746 0.9028 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8208(3) 1.05401(16) 0.82613(13) 0.0345(6) Uani 1 1 d . . . . .
H14 H 0.8235 1.1149 0.8228 0.041 Uiso 1 1 calc R U . . .
C15 C 0.8970(2) 0.98971(16) 0.78296(13) 0.0336(6) Uani 1 1 d . . . . .
H15 H 0.9516 1.0061 0.7499 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8928(2) 0.90129(16) 0.78837(12) 0.0325(6) Uani 1 1 d . . . . .
H16 H 0.9431 0.8563 0.7580 0.039 Uiso 1 1 calc R U . . .
C17 C 0.8156(2) 0.87774(15) 0.83798(12) 0.0294(5) Uani 1 1 d . . . . .
H17 H 0.8156 0.8174 0.8425 0.035 Uiso 1 1 calc R U . . .
C18 C -0.1489(3) 0.46982(16) 0.14205(13) 0.0333(6) Uani 1 1 d . . . . .
C19 C -0.2903(3) 0.47077(18) 0.12824(14) 0.0433(7) Uani 1 1 d . . . . .
H19 H -0.3497 0.4237 0.1346 0.052 Uiso 1 1 calc R U . . .
C20 C -0.3445(3) 0.54151(19) 0.10498(15) 0.0497(7) Uani 1 1 d . . . . .
H20 H -0.4420 0.5433 0.0953 0.060 Uiso 1 1 calc R U . . .
C21 C -0.2569(3) 0.61017(18) 0.09559(15) 0.0479(7) Uani 1 1 d . . . . .
H21 H -0.2948 0.6588 0.0798 0.057 Uiso 1 1 calc R U . . .
C22 C -0.1160(3) 0.60780(16) 0.10905(13) 0.0377(6) Uani 1 1 d . . . . .
H22 H -0.0571 0.6545 0.1019 0.045 Uiso 1 1 calc R U . . .
C23 C -0.0578(2) 0.53700(15) 0.13323(12) 0.0298(5) Uani 1 1 d . . . . .
C24 C 0.0902(2) 0.53073(15) 0.15062(12) 0.0276(5) Uani 1 1 d . . . . .
C25 C 0.1343(3) 0.45989(15) 0.17423(12) 0.0310(5) Uani 1 1 d . . . . .
C26 C 0.0380(3) 0.39100(16) 0.18458(13) 0.0338(6) Uani 1 1 d . . . . .
C27 C 0.2853(3) 0.44727(16) 0.19440(14) 0.0377(6) Uani 1 1 d . . . . .
H27A H 0.3411 0.5075 0.2067 0.045 Uiso 1 1 calc R U . . .
H27B H 0.2990 0.4282 0.2413 0.045 Uiso 1 1 calc R U . . .
C28 C 0.3357(3) 0.37813(18) 0.13208(15) 0.0391(6) Uani 1 1 d . . . . .
C29 C 0.1913(2) 0.60403(15) 0.14546(12) 0.0289(5) Uani 1 1 d . . . . .
C30 C 0.2604(3) 0.67081(17) 0.21251(14) 0.0445(7) Uani 1 1 d . . . . .
H30 H 0.2403 0.6710 0.2613 0.053 Uiso 1 1 calc R U . . .
C31 C 0.3587(3) 0.73747(18) 0.20925(14) 0.0489(8) Uani 1 1 d . . . . .
H31 H 0.4044 0.7831 0.2557 0.059 Uiso 1 1 calc R U . . .
C32 C 0.3898(3) 0.73770(17) 0.13949(14) 0.0405(6) Uani 1 1 d . . . . .
H32 H 0.4574 0.7829 0.1371 0.049 Uiso 1 1 calc R U . . .
C33 C 0.3219(3) 0.67158(18) 0.07288(14) 0.0492(7) Uani 1 1 d . . . . .
H33 H 0.3434 0.6711 0.0243 0.059 Uiso 1 1 calc R U . . .
C34 C 0.2227(3) 0.60571(17) 0.07556(14) 0.0468(7) Uani 1 1 d . . . . .
H34 H 0.1759 0.5612 0.0288 0.056 Uiso 1 1 calc R U . . .
C35 C 0.4031(2) 0.96941(15) 0.39675(12) 0.0270(5) Uani 1 1 d . . . . .
C36 C 0.3270(3) 1.03957(15) 0.38619(13) 0.0350(6) Uani 1 1 d . . . . .
H36 H 0.2342 1.0417 0.3953 0.042 Uiso 1 1 calc R U . . .
C37 C 0.3879(3) 1.10642(16) 0.36222(13) 0.0372(6) Uani 1 1 d . . . . .
H37 H 0.3373 1.1556 0.3552 0.045 Uiso 1 1 calc R U . . .
C38 C 0.5236(3) 1.10201(16) 0.34830(13) 0.0363(6) Uani 1 1 d . . . . .
H38 H 0.5658 1.1489 0.3327 0.044 Uiso 1 1 calc R U . . .
C39 C 0.5968(3) 1.03040(15) 0.35692(13) 0.0332(6) Uani 1 1 d . . . . .
H39 H 0.6886 1.0275 0.3462 0.040 Uiso 1 1 calc R U . . .
C40 C 0.5374(2) 0.96122(14) 0.38145(12) 0.0257(5) Uani 1 1 d . . . . .
C41 C 0.6083(2) 0.88412(15) 0.39292(11) 0.0252(5) Uani 1 1 d . . . . .
C42 C 0.5443(2) 0.82440(15) 0.42116(12) 0.0267(5) Uani 1 1 d . . . . .
C43 C 0.4036(2) 0.83343(16) 0.43624(12) 0.0297(5) Uani 1 1 d . . . . .
C44 C 0.6083(2) 0.74360(14) 0.43860(13) 0.0321(6) Uani 1 1 d . . . . .
H44A H 0.7053 0.7444 0.4297 0.038 Uiso 1 1 calc R U . . .
H44B H 0.6098 0.7506 0.4939 0.038 Uiso 1 1 calc R U . . .
C45 C 0.5331(3) 0.65456(18) 0.39086(15) 0.0380(6) Uani 1 1 d . . . . .
C46 C 0.7490(2) 0.87249(14) 0.37176(12) 0.0267(5) Uani 1 1 d . . . . .
C47 C 0.7627(3) 0.84727(15) 0.29374(13) 0.0341(6) Uani 1 1 d . . . . .
H47 H 0.6827 0.8376 0.2551 0.041 Uiso 1 1 calc R U . . .
C48 C 0.8920(3) 0.83633(15) 0.27241(14) 0.0363(6) Uani 1 1 d . . . . .
H48 H 0.9002 0.8182 0.2192 0.044 Uiso 1 1 calc R U . . .
C49 C 1.0092(3) 0.85175(15) 0.32841(14) 0.0350(6) Uani 1 1 d . . . . .
H49 H 1.0981 0.8452 0.3140 0.042 Uiso 1 1 calc R U . . .
C50 C 0.9958(2) 0.87682(15) 0.40565(14) 0.0340(6) Uani 1 1 d . . . . .
H50 H 1.0760 0.8871 0.4442 0.041 Uiso 1 1 calc R U . . .
C51 C 0.8673(2) 0.88703(15) 0.42728(13) 0.0323(6) Uani 1 1 d . . . . .
H51 H 0.8598 0.9041 0.4805 0.039 Uiso 1 1 calc R U . . .
C52 C -0.0482(3) 0.50902(15) 0.61267(12) 0.0305(5) Uani 1 1 d . . . . .
C53 C -0.1125(3) 0.43383(16) 0.62631(13) 0.0355(6) Uani 1 1 d . . . . .
H53 H -0.2105 0.4214 0.6160 0.043 Uiso 1 1 calc R U . . .
C54 C -0.0295(3) 0.37806(16) 0.65520(13) 0.0392(6) Uani 1 1 d . . . . .
H54 H -0.0711 0.3261 0.6646 0.047 Uiso 1 1 calc R U . . .
C55 C 0.1134(3) 0.39601(16) 0.67089(14) 0.0395(6) Uani 1 1 d . . . . .
H55 H 0.1690 0.3568 0.6910 0.047 Uiso 1 1 calc R U . . .
C56 C 0.1746(3) 0.47097(15) 0.65720(12) 0.0324(6) Uani 1 1 d . . . . .
H56 H 0.2726 0.4834 0.6683 0.039 Uiso 1 1 calc R U . . .
C57 C 0.0943(2) 0.52902(14) 0.62716(12) 0.0267(5) Uani 1 1 d . . . . .
C58 C 0.1527(2) 0.60773(14) 0.60940(12) 0.0262(5) Uani 1 1 d . . . . .
C59 C 0.0668(2) 0.65734(15) 0.57751(12) 0.0273(5) Uani 1 1 d . . . . .
C60 C -0.0824(3) 0.63608(16) 0.56348(13) 0.0323(5) Uani 1 1 d . . . . .
C61 C 0.1152(2) 0.73767(14) 0.55297(13) 0.0312(5) Uani 1 1 d . . . . .
H61A H 0.2176 0.7428 0.5593 0.037 Uiso 1 1 calc R U . . .
H61B H 0.0781 0.7245 0.4973 0.037 Uiso 1 1 calc R U . . .
C62 C 0.0723(3) 0.82647(18) 0.59706(14) 0.0345(6) Uani 1 1 d . . . . .
C63 C 0.3059(2) 0.63047(14) 0.62736(13) 0.0272(5) Uani 1 1 d . . . . .
C64 C 0.3868(2) 0.60473(16) 0.56957(13) 0.0331(6) Uani 1 1 d . . . . .
H64 H 0.3437 0.5733 0.5176 0.040 Uiso 1 1 calc R U . . .
C65 C 0.5293(3) 0.62455(16) 0.58721(14) 0.0368(6) Uani 1 1 d . . . . .
H65 H 0.5839 0.6063 0.5476 0.044 Uiso 1 1 calc R U . . .
C66 C 0.5921(3) 0.67117(16) 0.66291(15) 0.0372(6) Uani 1 1 d . . . . .
H66 H 0.6898 0.6852 0.6753 0.045 Uiso 1 1 calc R U . . .
C67 C 0.5124(3) 0.69721(16) 0.72044(14) 0.0377(6) Uani 1 1 d . . . . .
H67 H 0.5558 0.7296 0.7722 0.045 Uiso 1 1 calc R U . . .
C68 C 0.3703(2) 0.67653(15) 0.70339(13) 0.0330(6) Uani 1 1 d . . . . .
H68 H 0.3166 0.6937 0.7435 0.040 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.371(3) . ?
O1 C1 1.375(2) . ?
O2 C9 1.211(3) . ?
O3 C26 1.377(3) . ?
O3 C18 1.384(3) . ?
O4 C26 1.209(3) . ?
O5 C43 1.370(3) . ?
O5 C35 1.384(2) . ?
O6 C43 1.214(2) . ?
O7 C60 1.379(3) . ?
O7 C52 1.381(3) . ?
O8 C60 1.208(3) . ?
N1 C11 1.147(3) . ?
N2 C28 1.136(3) . ?
N3 C45 1.140(3) . ?
N4 C62 1.138(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.452(3) . ?
C7 C8 1.354(3) . ?
C7 C12 1.495(3) . ?
C8 C9 1.460(3) . ?
C8 C10 1.500(3) . ?
C10 C11 1.473(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C13 1.389(3) . ?
C12 C17 1.393(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.375(3) . ?
C18 C23 1.392(3) . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.372(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.406(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.454(3) . ?
C24 C25 1.352(3) . ?
C24 C29 1.495(3) . ?
C25 C26 1.456(3) . ?
C25 C27 1.509(3) . ?
C27 C28 1.463(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C29 C34 1.379(3) . ?
C29 C30 1.388(3) . ?
C30 C31 1.390(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.368(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.375(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.383(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.380(3) . ?
C35 C40 1.392(3) . ?
C36 C37 1.378(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.395(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.372(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.407(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.450(3) . ?
C41 C42 1.356(3) . ?
C41 C46 1.493(3) . ?
C42 C43 1.453(3) . ?
C42 C44 1.510(3) . ?
C44 C45 1.459(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C46 C51 1.387(3) . ?
C46 C47 1.399(3) . ?
C47 C48 1.386(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.384(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.384(3) . ?
C49 H49 0.9500 . ?
C50 C51 1.380(3) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 C57 1.384(3) . ?
C52 C53 1.392(3) . ?
C53 C54 1.375(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.385(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.377(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.399(3) . ?
C56 H56 0.9500 . ?
C57 C58 1.455(3) . ?
C58 C59 1.349(3) . ?
C58 C63 1.490(3) . ?
C59 C60 1.452(3) . ?
C59 C61 1.514(3) . ?
C61 C62 1.464(3) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C63 C68 1.393(3) . ?
C63 C64 1.394(3) . ?
C64 C65 1.384(3) . ?
C64 H64 0.9500 . ?
C65 C66 1.385(3) . ?
C65 H65 0.9500 . ?
C66 C67 1.382(3) . ?
C66 H66 0.9500 . ?
C67 C68 1.381(3) . ?
C67 H67 0.9500 . ?
C68 H68 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
C9 O1 C1 121.58(17) . . ?
C26 O3 C18 121.34(18) . . ?
C43 O5 C35 121.71(18) . . ?
C60 O7 C52 121.00(18) . . ?
O1 C1 C2 115.98(19) . . ?
O1 C1 C6 121.4(2) . . ?
C2 C1 C6 122.7(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.2(2) . . ?
C1 C6 C7 118.4(2) . . ?
C5 C6 C7 124.3(2) . . ?
C8 C7 C6 118.96(19) . . ?
C8 C7 C12 121.5(2) . . ?
C6 C7 C12 119.30(19) . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 C10 124.3(2) . . ?
C9 C8 C10 114.15(19) . . ?
O2 C9 O1 117.2(2) . . ?
O2 C9 C8 125.0(2) . . ?
O1 C9 C8 117.8(2) . . ?
C11 C10 C8 113.13(19) . . ?
C11 C10 H10A 109.0 . . ?
C8 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C8 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N1 C11 C10 178.6(3) . . ?
C13 C12 C17 119.1(2) . . ?
C13 C12 C7 122.4(2) . . ?
C17 C12 C7 118.43(19) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.3(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C19 C18 O3 115.7(2) . . ?
C19 C18 C23 122.7(2) . . ?
O3 C18 C23 121.5(2) . . ?
C18 C19 C20 118.7(2) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.8(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C18 C23 C22 117.3(2) . . ?
C18 C23 C24 118.5(2) . . ?
C22 C23 C24 124.2(2) . . ?
C25 C24 C23 119.0(2) . . ?
C25 C24 C29 120.8(2) . . ?
C23 C24 C29 120.1(2) . . ?
C24 C25 C26 121.9(2) . . ?
C24 C25 C27 123.4(2) . . ?
C26 C25 C27 114.7(2) . . ?
O4 C26 O3 116.8(2) . . ?
O4 C26 C25 125.5(2) . . ?
O3 C26 C25 117.6(2) . . ?
C28 C27 C25 113.1(2) . . ?
C28 C27 H27A 109.0 . . ?
C25 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C25 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
N2 C28 C27 178.2(3) . . ?
C34 C29 C30 118.2(2) . . ?
C34 C29 C24 121.9(2) . . ?
C30 C29 C24 119.9(2) . . ?
C29 C30 C31 120.9(2) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C32 C31 C30 120.3(2) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 119.1(2) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C32 C33 C34 121.0(2) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C29 C34 C33 120.6(2) . . ?
C29 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 O5 116.4(2) . . ?
C36 C35 C40 122.8(2) . . ?
O5 C35 C40 120.8(2) . . ?
C37 C36 C35 118.8(2) . . ?
C37 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
C36 C37 C38 120.1(2) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C39 C38 C37 120.5(2) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 120.7(2) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 H39 119.7 . . ?
C35 C40 C39 117.1(2) . . ?
C35 C40 C41 118.86(19) . . ?
C39 C40 C41 124.0(2) . . ?
C42 C41 C40 119.1(2) . . ?
C42 C41 C46 122.3(2) . . ?
C40 C41 C46 118.54(18) . . ?
C41 C42 C43 121.3(2) . . ?
C41 C42 C44 124.6(2) . . ?
C43 C42 C44 114.17(18) . . ?
O6 C43 O5 116.9(2) . . ?
O6 C43 C42 125.0(2) . . ?
O5 C43 C42 118.08(19) . . ?
C45 C44 C42 112.41(19) . . ?
C45 C44 H44A 109.1 . . ?
C42 C44 H44A 109.1 . . ?
C45 C44 H44B 109.1 . . ?
C42 C44 H44B 109.1 . . ?
H44A C44 H44B 107.9 . . ?
N3 C45 C44 179.1(3) . . ?
C51 C46 C47 118.8(2) . . ?
C51 C46 C41 122.0(2) . . ?
C47 C46 C41 119.2(2) . . ?
C48 C47 C46 120.5(2) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C49 C48 C47 120.1(2) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C48 C49 C50 119.4(2) . . ?
C48 C49 H49 120.3 . . ?
C50 C49 H49 120.3 . . ?
C51 C50 C49 120.8(2) . . ?
C51 C50 H50 119.6 . . ?
C49 C50 H50 119.6 . . ?
C50 C51 C46 120.4(2) . . ?
C50 C51 H51 119.8 . . ?
C46 C51 H51 119.8 . . ?
O7 C52 C57 121.5(2) . . ?
O7 C52 C53 116.0(2) . . ?
C57 C52 C53 122.5(2) . . ?
C54 C53 C52 117.8(2) . . ?
C54 C53 H53 121.1 . . ?
C52 C53 H53 121.1 . . ?
C53 C54 C55 121.4(2) . . ?
C53 C54 H54 119.3 . . ?
C55 C54 H54 119.3 . . ?
C56 C55 C54 119.7(2) . . ?
C56 C55 H55 120.2 . . ?
C54 C55 H55 120.2 . . ?
C55 C56 C57 120.8(2) . . ?
C55 C56 H56 119.6 . . ?
C57 C56 H56 119.6 . . ?
C52 C57 C56 117.7(2) . . ?
C52 C57 C58 118.8(2) . . ?
C56 C57 C58 123.5(2) . . ?
C59 C58 C57 119.1(2) . . ?
C59 C58 C63 122.5(2) . . ?
C57 C58 C63 118.4(2) . . ?
C58 C59 C60 121.4(2) . . ?
C58 C59 C61 124.1(2) . . ?
C60 C59 C61 114.5(2) . . ?
O8 C60 O7 116.8(2) . . ?
O8 C60 C59 125.0(2) . . ?
O7 C60 C59 118.2(2) . . ?
C62 C61 C59 113.39(19) . . ?
C62 C61 H61A 108.9 . . ?
C59 C61 H61A 108.9 . . ?
C62 C61 H61B 108.9 . . ?
C59 C61 H61B 108.9 . . ?
H61A C61 H61B 107.7 . . ?
N4 C62 C61 178.1(3) . . ?
C68 C63 C64 119.2(2) . . ?
C68 C63 C58 119.7(2) . . ?
C64 C63 C58 121.2(2) . . ?
C65 C64 C63 120.7(2) . . ?
C65 C64 H64 119.7 . . ?
C63 C64 H64 119.7 . . ?
C64 C65 C66 119.7(2) . . ?
C64 C65 H65 120.2 . . ?
C66 C65 H65 120.2 . . ?
C67 C66 C65 120.0(2) . . ?
C67 C66 H66 120.0 . . ?
C65 C66 H66 120.0 . . ?
C68 C67 C66 120.6(2) . . ?
C68 C67 H67 119.7 . . ?
C66 C67 H67 119.7 . . ?
C67 C68 C63 119.9(2) . . ?
C67 C68 H68 120.0 . . ?
C63 C68 H68 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C2 176.2(2) . . . . ?
C9 O1 C1 C6 -3.7(3) . . . . ?
O1 C1 C2 C3 177.5(2) . . . . ?
C6 C1 C2 C3 -2.6(3) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 C5 3.6(4) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
O1 C1 C6 C5 -176.41(19) . . . . ?
C2 C1 C6 C5 3.7(3) . . . . ?
O1 C1 C6 C7 6.7(3) . . . . ?
C2 C1 C6 C7 -173.2(2) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C7 175.6(2) . . . . ?
C1 C6 C7 C8 -4.9(3) . . . . ?
C5 C6 C7 C8 178.5(2) . . . . ?
C1 C6 C7 C12 170.09(19) . . . . ?
C5 C6 C7 C12 -6.5(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C12 C7 C8 C9 -174.63(19) . . . . ?
C6 C7 C8 C10 -179.5(2) . . . . ?
C12 C7 C8 C10 5.7(3) . . . . ?
C1 O1 C9 O2 178.5(2) . . . . ?
C1 O1 C9 C8 -1.1(3) . . . . ?
C7 C8 C9 O2 -176.8(2) . . . . ?
C10 C8 C9 O2 2.9(3) . . . . ?
C7 C8 C9 O1 2.8(3) . . . . ?
C10 C8 C9 O1 -177.50(19) . . . . ?
C7 C8 C10 C11 -106.4(3) . . . . ?
C9 C8 C10 C11 73.9(3) . . . . ?
C8 C7 C12 C13 -113.5(3) . . . . ?
C6 C7 C12 C13 71.6(3) . . . . ?
C8 C7 C12 C17 66.2(3) . . . . ?
C6 C7 C12 C17 -108.6(2) . . . . ?
C17 C12 C13 C14 -1.1(3) . . . . ?
C7 C12 C13 C14 178.6(2) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 -1.5(3) . . . . ?
C15 C16 C17 C12 1.9(3) . . . . ?
C13 C12 C17 C16 -0.6(3) . . . . ?
C7 C12 C17 C16 179.7(2) . . . . ?
C26 O3 C18 C19 -178.4(2) . . . . ?
C26 O3 C18 C23 0.4(3) . . . . ?
O3 C18 C19 C20 178.5(2) . . . . ?
C23 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
O3 C18 C23 C22 -178.83(19) . . . . ?
C19 C18 C23 C24 178.9(2) . . . . ?
O3 C18 C23 C24 0.2(3) . . . . ?
C21 C22 C23 C18 0.6(3) . . . . ?
C21 C22 C23 C24 -178.4(2) . . . . ?
C18 C23 C24 C25 0.4(3) . . . . ?
C22 C23 C24 C25 179.3(2) . . . . ?
C18 C23 C24 C29 -177.1(2) . . . . ?
C22 C23 C24 C29 1.8(3) . . . . ?
C23 C24 C25 C26 -1.5(3) . . . . ?
C29 C24 C25 C26 175.93(19) . . . . ?
C23 C24 C25 C27 -179.5(2) . . . . ?
C29 C24 C25 C27 -2.0(3) . . . . ?
C18 O3 C26 O4 177.4(2) . . . . ?
C18 O3 C26 C25 -1.5(3) . . . . ?
C24 C25 C26 O4 -176.7(2) . . . . ?
C27 C25 C26 O4 1.4(3) . . . . ?
C24 C25 C26 O3 2.1(3) . . . . ?
C27 C25 C26 O3 -179.78(19) . . . . ?
C24 C25 C27 C28 -100.2(3) . . . . ?
C26 C25 C27 C28 81.7(3) . . . . ?
C25 C24 C29 C34 103.3(3) . . . . ?
C23 C24 C29 C34 -79.2(3) . . . . ?
C25 C24 C29 C30 -74.2(3) . . . . ?
C23 C24 C29 C30 103.3(3) . . . . ?
C34 C29 C30 C31 0.0(4) . . . . ?
C24 C29 C30 C31 177.5(3) . . . . ?
C29 C30 C31 C32 -0.6(4) . . . . ?
C30 C31 C32 C33 0.4(4) . . . . ?
C31 C32 C33 C34 0.4(4) . . . . ?
C30 C29 C34 C33 0.8(4) . . . . ?
C24 C29 C34 C33 -176.7(2) . . . . ?
C32 C33 C34 C29 -1.0(5) . . . . ?
C43 O5 C35 C36 -179.02(19) . . . . ?
C43 O5 C35 C40 2.0(3) . . . . ?
O5 C35 C36 C37 178.59(19) . . . . ?
C40 C35 C36 C37 -2.5(3) . . . . ?
C35 C36 C37 C38 0.6(3) . . . . ?
C36 C37 C38 C39 1.2(4) . . . . ?
C37 C38 C39 C40 -1.3(4) . . . . ?
C36 C35 C40 C39 2.3(3) . . . . ?
O5 C35 C40 C39 -178.75(18) . . . . ?
C36 C35 C40 C41 -178.9(2) . . . . ?
O5 C35 C40 C41 0.1(3) . . . . ?
C38 C39 C40 C35 -0.4(3) . . . . ?
C38 C39 C40 C41 -179.2(2) . . . . ?
C35 C40 C41 C42 -2.7(3) . . . . ?
C39 C40 C41 C42 176.1(2) . . . . ?
C35 C40 C41 C46 176.29(19) . . . . ?
C39 C40 C41 C46 -5.0(3) . . . . ?
C40 C41 C42 C43 3.2(3) . . . . ?
C46 C41 C42 C43 -175.7(2) . . . . ?
C40 C41 C42 C44 -177.63(19) . . . . ?
C46 C41 C42 C44 3.5(3) . . . . ?
C35 O5 C43 O6 -179.01(19) . . . . ?
C35 O5 C43 C42 -1.4(3) . . . . ?
C41 C42 C43 O6 176.1(2) . . . . ?
C44 C42 C43 O6 -3.1(3) . . . . ?
C41 C42 C43 O5 -1.3(3) . . . . ?
C44 C42 C43 O5 179.53(18) . . . . ?
C41 C42 C44 C45 -117.2(2) . . . . ?
C43 C42 C44 C45 62.0(3) . . . . ?
C42 C41 C46 C51 -70.3(3) . . . . ?
C40 C41 C46 C51 110.8(2) . . . . ?
C42 C41 C46 C47 110.5(2) . . . . ?
C40 C41 C46 C47 -68.4(3) . . . . ?
C51 C46 C47 C48 0.5(3) . . . . ?
C41 C46 C47 C48 179.7(2) . . . . ?
C46 C47 C48 C49 -1.0(3) . . . . ?
C47 C48 C49 C50 0.9(3) . . . . ?
C48 C49 C50 C51 -0.4(3) . . . . ?
C49 C50 C51 C46 -0.1(4) . . . . ?
C47 C46 C51 C50 0.1(3) . . . . ?
C41 C46 C51 C50 -179.1(2) . . . . ?
C60 O7 C52 C57 0.7(3) . . . . ?
C60 O7 C52 C53 -177.79(19) . . . . ?
O7 C52 C53 C54 178.39(19) . . . . ?
C57 C52 C53 C54 -0.1(3) . . . . ?
C52 C53 C54 C55 0.4(3) . . . . ?
C53 C54 C55 C56 -0.2(4) . . . . ?
C54 C55 C56 C57 -0.4(3) . . . . ?
O7 C52 C57 C56 -178.88(19) . . . . ?
C53 C52 C57 C56 -0.5(3) . . . . ?
O7 C52 C57 C58 0.1(3) . . . . ?
C53 C52 C57 C58 178.5(2) . . . . ?
C55 C56 C57 C52 0.7(3) . . . . ?
C55 C56 C57 C58 -178.2(2) . . . . ?
C52 C57 C58 C59 -1.7(3) . . . . ?
C56 C57 C58 C59 177.2(2) . . . . ?
C52 C57 C58 C63 178.2(2) . . . . ?
C56 C57 C58 C63 -2.8(3) . . . . ?
C57 C58 C59 C60 2.5(3) . . . . ?
C63 C58 C59 C60 -177.5(2) . . . . ?
C57 C58 C59 C61 -176.99(19) . . . . ?
C63 C58 C59 C61 3.1(3) . . . . ?
C52 O7 C60 O8 179.9(2) . . . . ?
C52 O7 C60 C59 0.0(3) . . . . ?
C58 C59 C60 O8 178.5(2) . . . . ?
C61 C59 C60 O8 -2.0(3) . . . . ?
C58 C59 C60 O7 -1.6(3) . . . . ?
C61 C59 C60 O7 177.86(18) . . . . ?
C58 C59 C61 C62 -115.8(3) . . . . ?
C60 C59 C61 C62 64.7(3) . . . . ?
C59 C58 C63 C68 102.3(3) . . . . ?
C57 C58 C63 C68 -77.6(3) . . . . ?
C59 C58 C63 C64 -79.1(3) . . . . ?
C57 C58 C63 C64 101.0(2) . . . . ?
C68 C63 C64 C65 0.0(3) . . . . ?
C58 C63 C64 C65 -178.7(2) . . . . ?
C63 C64 C65 C66 -0.6(4) . . . . ?
C64 C65 C66 C67 0.3(3) . . . . ?
C65 C66 C67 C68 0.5(4) . . . . ?
C66 C67 C68 C63 -1.2(4) . . . . ?
C64 C63 C68 C67 0.9(3) . . . . ?
C58 C63 C68 C67 179.6(2) . . . . ?

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
C61 H61A O6 0.99 2.55 3.159(3) 119.9 .
C27 H27A N3 0.99 2.70 3.265(4) 116.8 .

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1851297'
_audit_update_record             
;
2018-06-24 deposited with the CCDC.
2018-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 Br N O2'
_chemical_formula_weight         340.17

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.067(2)
_cell_length_b                   9.1332(18)
_cell_length_c                   15.755(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.76(3)
_cell_angle_gamma                90
_cell_volume                     1406.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3709
_cell_measurement_theta_min      2.0829
_cell_measurement_theta_max      27.8984

_exptl_crystal_description       bulk
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.924
_shelx_estimated_absorpt_T_min   0.592
_shelx_estimated_absorpt_T_max   0.720
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14569
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3348
_reflns_number_gt                2002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3348
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.14954(3) -0.39711(3) 1.06758(2) 0.02852(11) Uani 1 1 d . . . . .
O1 O -0.12175(17) -0.0315(2) 0.83630(13) 0.0263(5) Uani 1 1 d . . . . .
O2 O -0.25362(19) 0.1131(2) 0.73905(14) 0.0336(5) Uani 1 1 d . . . . .
N1 N -0.0579(4) 0.2828(4) 0.5681(2) 0.0775(12) Uani 1 1 d . . . . .
C1 C 0.0052(3) -0.0688(3) 0.88831(19) 0.0223(7) Uani 1 1 d . . . . .
C2 C 0.0094(3) -0.1934(3) 0.93932(18) 0.0247(7) Uani 1 1 d . . . . .
H2 H -0.0703 -0.2497 0.9380 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1354(3) -0.2319(3) 0.99229(18) 0.0244(7) Uani 1 1 d . . . . .
C4 C 0.2530(3) -0.1511(3) 0.9941(2) 0.0274(7) Uani 1 1 d . . . . .
H4 H 0.3381 -0.1805 1.0305 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2449(3) -0.0286(3) 0.94297(18) 0.0250(7) Uani 1 1 d . . . . .
H5 H 0.3254 0.0266 0.9445 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1202(3) 0.0172(3) 0.88818(18) 0.0203(7) Uani 1 1 d . . . . .
C7 C 0.1038(3) 0.1486(3) 0.83550(19) 0.0207(7) Uani 1 1 d . . . . .
C8 C -0.0219(3) 0.1857(3) 0.78712(18) 0.0214(7) Uani 1 1 d . . . . .
C9 C -0.1399(3) 0.0923(3) 0.7845(2) 0.0238(7) Uani 1 1 d . . . . .
C10 C -0.0514(3) 0.3221(3) 0.73245(19) 0.0267(7) Uani 1 1 d . . . . .
H10A H -0.1400 0.3631 0.7381 0.032 Uiso 1 1 calc R U . . .
H10B H 0.0203 0.3955 0.7558 0.032 Uiso 1 1 calc R U . . .
C11 C -0.0572(3) 0.2986(4) 0.6398(2) 0.0405(9) Uani 1 1 d . . . . .
C12 C 0.2271(3) 0.2419(3) 0.83855(18) 0.0208(7) Uani 1 1 d . . . . .
C13 C 0.2431(3) 0.3724(3) 0.8849(2) 0.0286(7) Uani 1 1 d . . . . .
H13 H 0.1729 0.4050 0.9114 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3614(3) 0.4562(4) 0.8930(2) 0.0360(8) Uani 1 1 d . . . . .
H14 H 0.3721 0.5454 0.9249 0.043 Uiso 1 1 calc R U . . .
C15 C 0.4627(3) 0.4079(4) 0.8542(2) 0.0372(9) Uani 1 1 d . . . . .
H15 H 0.5438 0.4641 0.8600 0.045 Uiso 1 1 calc R U . . .
C16 C 0.4480(3) 0.2799(4) 0.8073(2) 0.0382(9) Uani 1 1 d . . . . .
H16 H 0.5179 0.2483 0.7802 0.046 Uiso 1 1 calc R U . . .
C17 C 0.3292(3) 0.1962(4) 0.7996(2) 0.0303(8) Uani 1 1 d . . . . .
H17 H 0.3188 0.1074 0.7673 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.904(3) . ?
O1 C9 1.381(3) . ?
O1 C1 1.386(3) . ?
O2 C9 1.212(3) . ?
N1 C11 1.138(4) . ?
C1 C2 1.388(4) . ?
C1 C6 1.399(4) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(4) . ?
C4 C5 1.369(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.446(4) . ?
C7 C8 1.356(4) . ?
C7 C12 1.497(4) . ?
C8 C9 1.455(4) . ?
C8 C10 1.503(4) . ?
C10 C11 1.463(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C17 1.382(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.396(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.400(4) . ?
C16 H16 0.9500 . ?
C17 H17 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
C9 O1 C1 121.6(2) . . ?
O1 C1 C2 116.2(2) . . ?
O1 C1 C6 120.5(3) . . ?
C2 C1 C6 123.3(3) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 Br1 119.9(2) . . ?
C4 C3 Br1 118.1(2) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 116.7(3) . . ?
C1 C6 C7 119.0(2) . . ?
C5 C6 C7 124.2(3) . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 C12 122.1(3) . . ?
C6 C7 C12 118.3(2) . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 C10 124.1(3) . . ?
C9 C8 C10 114.9(2) . . ?
O2 C9 O1 116.8(3) . . ?
O2 C9 C8 125.1(3) . . ?
O1 C9 C8 118.1(2) . . ?
C11 C10 C8 114.0(3) . . ?
C11 C10 H10A 108.8 . . ?
C8 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C8 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N1 C11 C10 177.8(4) . . ?
C17 C12 C13 119.2(3) . . ?
C17 C12 C7 120.8(3) . . ?
C13 C12 C7 119.9(3) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 120.5(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C2 178.2(3) . . . . ?
C9 O1 C1 C6 -1.5(4) . . . . ?
O1 C1 C2 C3 -179.6(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 Br1 177.7(2) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
Br1 C3 C4 C5 -177.7(2) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
O1 C1 C6 C5 180.0(2) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
O1 C1 C6 C7 2.3(4) . . . . ?
C2 C1 C6 C7 -177.3(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 177.3(3) . . . . ?
C1 C6 C7 C8 -0.2(4) . . . . ?
C5 C6 C7 C8 -177.7(3) . . . . ?
C1 C6 C7 C12 177.9(3) . . . . ?
C5 C6 C7 C12 0.4(4) . . . . ?
C6 C7 C8 C9 -2.6(4) . . . . ?
C12 C7 C8 C9 179.3(3) . . . . ?
C6 C7 C8 C10 177.9(3) . . . . ?
C12 C7 C8 C10 -0.2(4) . . . . ?
C1 O1 C9 O2 177.6(2) . . . . ?
C1 O1 C9 C8 -1.3(4) . . . . ?
C7 C8 C9 O2 -175.4(3) . . . . ?
C10 C8 C9 O2 4.2(4) . . . . ?
C7 C8 C9 O1 3.4(4) . . . . ?
C10 C8 C9 O1 -177.1(2) . . . . ?
C7 C8 C10 C11 98.1(3) . . . . ?
C9 C8 C10 C11 -81.4(3) . . . . ?
C8 C7 C12 C17 -109.8(3) . . . . ?
C6 C7 C12 C17 72.0(4) . . . . ?
C8 C7 C12 C13 73.6(4) . . . . ?
C6 C7 C12 C13 -104.5(3) . . . . ?
C17 C12 C13 C14 -0.7(4) . . . . ?
C7 C12 C13 C14 176.0(3) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C13 C12 C17 C16 0.5(4) . . . . ?
C7 C12 C17 C16 -176.1(3) . . . . ?
C15 C16 C17 C12 0.2(5) . . . . ?

_refine_diff_density_max         0.693
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.104

