# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_is_rd234f2
_database_code_depnum_ccdc_archive 'CCDC 2250461'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N O2'
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29

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'

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

# 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'

_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                   9.9310(8)
_cell_length_b                   11.5257(9)
_cell_length_c                   31.731(3)
_cell_angle_alpha                90.580(3)
_cell_angle_beta                 92.359(3)
_cell_angle_gamma                109.744(3)
_cell_volume                     3414.4(5)
_cell_formula_units_Z            10
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      33.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   '(SADABS-2016/2; Sheldrick, 2015)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            101688
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.878
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13405
_reflns_number_gt                9982
_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       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+5.1497P] 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         13405
_refine_ls_number_parameters     955
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1724
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# 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
N1 N 1.5035(2) 0.9282(2) 0.04678(7) 0.0288(5) Uani 1 1 d . . . . .
O1 O 1.77372(18) 0.83148(16) 0.03377(5) 0.0214(4) Uani 1 1 d . . . . .
O2 O 1.8507(2) 0.8915(2) -0.09294(6) 0.0370(5) Uani 1 1 d . . . . .
C1 C 1.6571(3) 0.8245(2) 0.00527(8) 0.0194(5) Uani 1 1 d . . . . .
C2 C 1.5666(3) 0.6958(2) -0.01432(7) 0.0200(5) Uani 1 1 d . . . . .
H2 H 1.6299 0.6450 -0.0174 0.024 Uiso 1 1 calc R U . . .
C3 C 1.5586(3) 0.7608(2) -0.05642(8) 0.0256(6) Uani 1 1 d . . . . .
H3A H 1.5792 0.7184 -0.0814 0.031 Uiso 1 1 calc R U . . .
H3B H 1.4685 0.7786 -0.0613 0.031 Uiso 1 1 calc R U . . .
C4 C 1.6863(3) 0.8737(2) -0.04019(8) 0.0212(5) Uani 1 1 d . . . . .
H4 H 1.6703 0.9539 -0.0444 0.025 Uiso 1 1 calc R U . . .
C5 C 1.8265(3) 0.8722(2) -0.05593(8) 0.0229(5) Uani 1 1 d . . . . .
C6 C 1.9279(3) 0.8480(2) -0.02551(8) 0.0217(5) Uani 1 1 d . . . . .
C7 C 2.0594(3) 0.8437(2) -0.03870(9) 0.0279(6) Uani 1 1 d . . . . .
H7 H 2.0813 0.8556 -0.0675 0.033 Uiso 1 1 calc R U . . .
C8 C 2.1562(3) 0.8227(3) -0.01066(10) 0.0330(7) Uani 1 1 d . . . . .
H8 H 2.2443 0.8192 -0.0201 0.040 Uiso 1 1 calc R U . . .
C9 C 2.1254(3) 0.8063(3) 0.03184(10) 0.0333(7) Uani 1 1 d . . . . .
H9 H 2.1934 0.7926 0.0513 0.040 Uiso 1 1 calc R U . . .
C10 C 1.9970(3) 0.8098(2) 0.04587(9) 0.0268(6) Uani 1 1 d . . . . .
H10 H 1.9766 0.7991 0.0748 0.032 Uiso 1 1 calc R U . . .
C11 C 1.8981(3) 0.8291(2) 0.01700(8) 0.0201(5) Uani 1 1 d . . . . .
C12 C 1.5703(3) 0.8834(2) 0.02856(8) 0.0213(5) Uani 1 1 d . . . . .
C13 C 1.4307(3) 0.6193(2) 0.00480(8) 0.0201(5) Uani 1 1 d . . . . .
C14 C 1.4260(3) 0.5962(2) 0.04778(8) 0.0238(5) Uani 1 1 d . . . . .
H14 H 1.5103 0.6293 0.0654 0.029 Uiso 1 1 calc R U . . .
C15 C 1.2988(3) 0.5252(2) 0.06506(9) 0.0278(6) Uani 1 1 d . . . . .
H15 H 1.2965 0.5106 0.0945 0.033 Uiso 1 1 calc R U . . .
C16 C 1.1751(3) 0.4758(2) 0.03956(9) 0.0280(6) Uani 1 1 d . . . . .
H16 H 1.0880 0.4280 0.0515 0.034 Uiso 1 1 calc R U . . .
C17 C 1.1792(3) 0.4964(2) -0.00320(9) 0.0286(6) Uani 1 1 d . . . . .
H17 H 1.0951 0.4617 -0.0209 0.034 Uiso 1 1 calc R U . . .
C18 C 1.3062(3) 0.5679(2) -0.02052(8) 0.0249(6) Uani 1 1 d . . . . .
H18 H 1.3080 0.5819 -0.0500 0.030 Uiso 1 1 calc R U . . .
N2 N 1.5640(2) 0.5147(2) 0.15196(7) 0.0293(5) Uani 1 1 d . . . . .
O3 O 1.29476(17) 0.61466(16) 0.16342(5) 0.0196(4) Uani 1 1 d . . . . .
O4 O 1.2048(2) 0.54686(19) 0.28896(6) 0.0312(5) Uani 1 1 d . . . . .
C19 C 1.4095(2) 0.6197(2) 0.19268(7) 0.0158(5) Uani 1 1 d . . . . .
C20 C 1.4995(2) 0.7478(2) 0.21271(7) 0.0150(5) Uani 1 1 d . . . . .
H20 H 1.4358 0.7984 0.2154 0.018 Uiso 1 1 calc R U . . .
C21 C 1.5041(3) 0.6826(2) 0.25482(8) 0.0199(5) Uani 1 1 d . . . . .
H21A H 1.4820 0.7250 0.2795 0.024 Uiso 1 1 calc R U . . .
H21B H 1.5936 0.6643 0.2603 0.024 Uiso 1 1 calc R U . . .
C22 C 1.3762(2) 0.5698(2) 0.23773(7) 0.0169(5) Uani 1 1 d . . . . .
H22 H 1.3917 0.4893 0.2420 0.020 Uiso 1 1 calc R U . . .
C23 C 1.2342(3) 0.5704(2) 0.25243(8) 0.0187(5) Uani 1 1 d . . . . .
C24 C 1.1374(2) 0.6009(2) 0.22165(8) 0.0181(5) Uani 1 1 d . . . . .
C25 C 1.0070(3) 0.6087(2) 0.23432(8) 0.0222(5) Uani 1 1 d . . . . .
H25 H 0.9814 0.5930 0.2628 0.027 Uiso 1 1 calc R U . . .
C26 C 0.9156(3) 0.6386(2) 0.20618(9) 0.0260(6) Uani 1 1 d . . . . .
H26 H 0.8283 0.6450 0.2152 0.031 Uiso 1 1 calc R U . . .
C27 C 0.9521(3) 0.6596(2) 0.16422(9) 0.0269(6) Uani 1 1 d . . . . .
H27 H 0.8889 0.6799 0.1447 0.032 Uiso 1 1 calc R U . . .
C28 C 1.0792(3) 0.6511(2) 0.15080(8) 0.0222(5) Uani 1 1 d . . . . .
H28 H 1.1028 0.6643 0.1221 0.027 Uiso 1 1 calc R U . . .
C29 C 1.1724(2) 0.6228(2) 0.17975(8) 0.0170(5) Uani 1 1 d . . . . .
C30 C 1.4962(3) 0.5604(2) 0.16976(8) 0.0191(5) Uani 1 1 d . . . . .
C31 C 1.6356(2) 0.8254(2) 0.19372(7) 0.0157(5) Uani 1 1 d . . . . .
C32 C 1.6389(3) 0.8506(2) 0.15096(8) 0.0201(5) Uani 1 1 d . . . . .
H32 H 1.5541 0.8181 0.1334 0.024 Uiso 1 1 calc R U . . .
C33 C 1.7651(3) 0.9228(2) 0.13362(8) 0.0250(6) Uani 1 1 d . . . . .
H33 H 1.7665 0.9383 0.1043 0.030 Uiso 1 1 calc R U . . .
C34 C 1.8892(3) 0.9726(2) 0.15895(8) 0.0242(6) Uani 1 1 d . . . . .
H34 H 1.9756 1.0221 0.1471 0.029 Uiso 1 1 calc R U . . .
C35 C 1.8859(3) 0.9493(2) 0.20173(9) 0.0234(5) Uani 1 1 d . . . . .
H35 H 1.9700 0.9843 0.2194 0.028 Uiso 1 1 calc R U . . .
C36 C 1.7604(3) 0.8753(2) 0.21896(8) 0.0186(5) Uani 1 1 d . . . . .
H36 H 1.7597 0.8586 0.2482 0.022 Uiso 1 1 calc R U . . .
N3 N 0.4691(3) 0.7090(2) 0.44725(7) 0.0300(5) Uani 1 1 d . . . . .
O7 O 0.73888(18) 0.61024(16) 0.43553(5) 0.0221(4) Uani 1 1 d . . . . .
O8 O 0.8251(2) 0.6755(2) 0.30967(6) 0.0331(5) Uani 1 1 d . . . . .
C37 C 0.6229(3) 0.6038(2) 0.40652(7) 0.0192(5) Uani 1 1 d . . . . .
C38 C 0.5335(3) 0.4754(2) 0.38688(7) 0.0192(5) Uani 1 1 d . . . . .
H38 H 0.5974 0.4250 0.3843 0.023 Uiso 1 1 calc R U . . .
C39 C 0.5271(3) 0.5391(2) 0.34449(8) 0.0219(5) Uani 1 1 d . . . . .
H39A H 0.4369 0.5564 0.3390 0.026 Uiso 1 1 calc R U . . .
H39B H 0.5496 0.4965 0.3199 0.026 Uiso 1 1 calc R U . . .
C40 C 0.6540(3) 0.6528(2) 0.36128(8) 0.0215(5) Uani 1 1 d . . . . .
H40 H 0.6374 0.7328 0.3568 0.026 Uiso 1 1 calc R U . . .
C41 C 0.7963(3) 0.6526(2) 0.34617(8) 0.0223(5) Uani 1 1 d . . . . .
C42 C 0.8947(3) 0.6238(2) 0.37701(8) 0.0221(5) Uani 1 1 d . . . . .
C43 C 1.0256(3) 0.6172(2) 0.36428(9) 0.0264(6) Uani 1 1 d . . . . .
H43 H 1.0506 0.6323 0.3358 0.032 Uiso 1 1 calc R U . . .
C44 C 1.1182(3) 0.5891(3) 0.39260(9) 0.0303(6) Uani 1 1 d . . . . .
H44 H 1.2055 0.5829 0.3835 0.036 Uiso 1 1 calc R U . . .
C45 C 1.0835(3) 0.5698(3) 0.43440(9) 0.0311(6) Uani 1 1 d . . . . .
H45 H 1.1480 0.5513 0.4539 0.037 Uiso 1 1 calc R U . . .
C46 C 0.9561(3) 0.5772(2) 0.44809(9) 0.0266(6) Uani 1 1 d . . . . .
H46 H 0.9334 0.5648 0.4769 0.032 Uiso 1 1 calc R U . . .
C47 C 0.8616(3) 0.6031(2) 0.41907(8) 0.0215(5) Uani 1 1 d . . . . .
C48 C 0.5363(3) 0.6637(2) 0.42942(8) 0.0218(5) Uani 1 1 d . . . . .
C49 C 0.3974(3) 0.3982(2) 0.40613(8) 0.0199(5) Uani 1 1 d . . . . .
C50 C 0.3954(3) 0.3721(2) 0.44911(8) 0.0255(6) Uani 1 1 d . . . . .
H50 H 0.4807 0.4041 0.4665 0.031 Uiso 1 1 calc R U . . .
C51 C 0.2700(3) 0.2999(2) 0.46645(8) 0.0277(6) Uani 1 1 d . . . . .
H51 H 0.2692 0.2832 0.4957 0.033 Uiso 1 1 calc R U . . .
C52 C 0.1452(3) 0.2519(2) 0.44131(9) 0.0279(6) Uani 1 1 d . . . . .
H52 H 0.0589 0.2031 0.4534 0.033 Uiso 1 1 calc R U . . .
C53 C 0.1466(3) 0.2750(2) 0.39877(9) 0.0258(6) Uani 1 1 d . . . . .
H53 H 0.0616 0.2409 0.3814 0.031 Uiso 1 1 calc R U . . .
C54 C 0.2721(3) 0.3483(2) 0.38118(8) 0.0234(5) Uani 1 1 d . . . . .
H54 H 0.2722 0.3644 0.3519 0.028 Uiso 1 1 calc R U . . .
N4 N 1.5828(3) 0.3892(2) 0.24466(8) 0.0313(5) Uani 1 1 d . . . . .
O5 O 1.84548(18) 0.28073(16) 0.24508(5) 0.0217(4) Uani 1 1 d . . . . .
C55 C 1.7460(3) 0.2800(2) 0.21124(8) 0.0192(5) Uani 1 1 d . . . . .
C56 C 1.6594(3) 0.1546(2) 0.18860(8) 0.0209(5) Uani 1 1 d . . . . .
H56 H 1.7212 0.1018 0.1880 0.025 Uiso 1 1 calc R U . . .
C57 C 1.6750(3) 0.2260(3) 0.14711(8) 0.0291(6) Uani 1 1 d . . . . .
H57A H 1.7018 0.1841 0.1231 0.035 Uiso 1 1 calc R U . . .
H57B H 1.5911 0.2506 0.1392 0.035 Uiso 1 1 calc R U . . .
C58 C 1.8019(3) 0.3314(2) 0.16804(8) 0.0263(6) Uani 1 1 d . . . . .
H58 H 1.7975 0.4155 0.1628 0.032 Uiso 1 1 calc R U . . .
C59 C 1.9455(3) 0.3194(2) 0.15940(9) 0.0320(7) Uani 1 1 d . . . . .
O6 O 1.9902(3) 0.3394(2) 0.12413(7) 0.0496(6) Uani 1 1 d . . . . .
C60 C 2.0241(3) 0.2854(2) 0.19442(9) 0.0284(6) Uani 1 1 d . . . . .
C61 C 2.1563(3) 0.2689(3) 0.18776(11) 0.0401(8) Uani 1 1 d . . . . .
H61 H 2.1935 0.2789 0.1604 0.048 Uiso 1 1 calc R U . . .
C62 C 2.2315(3) 0.2383(3) 0.22063(13) 0.0462(9) Uani 1 1 d . . . . .
H62 H 2.3196 0.2261 0.2158 0.055 Uiso 1 1 calc R U . . .
C63 C 2.1798(3) 0.2252(3) 0.26048(12) 0.0449(9) Uani 1 1 d . . . . .
H63 H 2.2338 0.2062 0.2831 0.054 Uiso 1 1 calc R U . . .
C64 C 2.0504(3) 0.2393(2) 0.26792(10) 0.0317(6) Uani 1 1 d . . . . .
H64 H 2.0147 0.2297 0.2955 0.038 Uiso 1 1 calc R U . . .
C65 C 1.9729(3) 0.2680(2) 0.23457(9) 0.0237(6) Uani 1 1 d . . . . .
C66 C 1.6541(3) 0.3422(2) 0.22966(8) 0.0222(5) Uani 1 1 d . . . . .
C67 C 1.5147(3) 0.0783(2) 0.20227(8) 0.0200(5) Uani 1 1 d . . . . .
C68 C 1.4923(3) 0.0465(2) 0.24423(9) 0.0252(6) Uani 1 1 d . . . . .
H68 H 1.5697 0.0751 0.2647 0.030 Uiso 1 1 calc R U . . .
C69 C 1.3586(3) -0.0263(2) 0.25651(10) 0.0292(6) Uani 1 1 d . . . . .
H69 H 1.3444 -0.0471 0.2853 0.035 Uiso 1 1 calc R U . . .
C70 C 1.2453(3) -0.0690(2) 0.22681(11) 0.0352(7) Uani 1 1 d . . . . .
H70 H 1.1535 -0.1189 0.2353 0.042 Uiso 1 1 calc R U . . .
C71 C 1.2657(3) -0.0392(3) 0.18513(11) 0.0348(7) Uani 1 1 d . . . . .
H71 H 1.1882 -0.0688 0.1648 0.042 Uiso 1 1 calc R U . . .
C72 C 1.3999(3) 0.0344(3) 0.17276(9) 0.0286(6) Uani 1 1 d . . . . .
H72 H 1.4134 0.0548 0.1440 0.034 Uiso 1 1 calc R U . . .
N5 N -0.4562(3) 0.1590(2) 0.64546(8) 0.0327(6) Uani 1 1 d . . . . .
O9 O -0.19041(19) 0.05530(17) 0.64115(6) 0.0256(4) Uani 1 1 d . . . . .
C73 C -0.2948(3) 0.0536(2) 0.60885(8) 0.0223(5) Uani 1 1 d . . . . .
C74 C -0.3821(3) -0.0717(2) 0.58642(8) 0.0229(5) Uani 1 1 d . . . . .
H74 H -0.3195 -0.1236 0.5847 0.027 Uiso 1 1 calc R U . . .
C75 C -0.3744(4) -0.0007(3) 0.54504(9) 0.0352(7) Uani 1 1 d . . . . .
H75A H -0.3496 -0.0417 0.5204 0.042 Uiso 1 1 calc R U . . .
H75B H -0.4603 0.0221 0.5384 0.042 Uiso 1 1 calc R U . . .
C76 C -0.2469(3) 0.1057(3) 0.56505(8) 0.0310(6) Uani 1 1 d . . . . .
H76 H -0.2551 0.1889 0.5605 0.037 Uiso 1 1 calc R U . A 1
C77A C -0.1113(9) 0.0969(6) 0.5521(2) 0.0296(12) Uani 0.76(2) 1 d D U P B 1
O10A O -0.0772(12) 0.1162(5) 0.5156(2) 0.0534(18) Uani 0.76(2) 1 d D . P B 1
C78A C -0.0213(5) 0.0660(5) 0.5851(3) 0.0294(13) Uani 0.76(2) 1 d DG . P B 1
C79A C 0.1094(5) 0.0570(5) 0.5747(4) 0.0421(18) Uani 0.76(2) 1 d DG . P B 1
H79A H 0.1384 0.0683 0.5465 0.051 Uiso 0.76(2) 1 calc R U P B 1
C80A C 0.1977(3) 0.0312(6) 0.6057(4) 0.047(2) Uani 0.76(2) 1 d DG . P B 1
H80A H 0.2871 0.0250 0.5986 0.057 Uiso 0.76(2) 1 calc R U P B 1
C81A C 0.1553(5) 0.0146(5) 0.6470(4) 0.044(2) Uani 0.76(2) 1 d DG . P B 1
H81A H 0.2156 -0.0030 0.6682 0.053 Uiso 0.76(2) 1 calc R U P B 1
C82A C 0.0245(5) 0.0237(5) 0.6574(3) 0.0355(13) Uani 0.76(2) 1 d DG . P B 1
H82A H -0.0045 0.0123 0.6857 0.043 Uiso 0.76(2) 1 calc R U P B 1
C83A C -0.0638(4) 0.0494(6) 0.6265(3) 0.0280(13) Uani 0.76(2) 1 d DG . P B 1
C77B C -0.082(2) 0.098(2) 0.5596(5) 0.023(3) Uiso 0.24(2) 1 d D U P B 2
O10B O -0.0392(17) 0.1153(18) 0.5238(4) 0.033(3) Uiso 0.24(2) 1 d D U P B 2
C78B C -0.0080(15) 0.0574(19) 0.5945(4) 0.023(2) Uiso 0.24(2) 1 d DG U P B 2
C79B C 0.1224(14) 0.0416(14) 0.5880(3) 0.016(3) Uiso 0.24(2) 1 d DG U P B 2
H79B H 0.1592 0.0505 0.5606 0.019 Uiso 0.24(2) 1 calc R U P B 2
C80B C 0.1988(12) 0.0129(12) 0.6216(4) 0.020(3) Uiso 0.24(2) 1 d DG U P B 2
H80B H 0.2879 0.0021 0.6172 0.024 Uiso 0.24(2) 1 calc R U P B 2
C81B C 0.1448(13) -0.0001(13) 0.6617(4) 0.020(3) Uiso 0.24(2) 1 d DG U P B 2
H81B H 0.1971 -0.0197 0.6846 0.023 Uiso 0.24(2) 1 calc R U P B 2
C82B C 0.0145(15) 0.0157(18) 0.6681(3) 0.014(3) Uiso 0.24(2) 1 d DG U P B 2
H82B H -0.0224 0.0068 0.6955 0.016 Uiso 0.24(2) 1 calc R U P B 2
C83B C -0.0620(15) 0.044(2) 0.6346(4) 0.016(3) Uiso 0.24(2) 1 d DG U P B 2
C84 C -0.3860(3) 0.1140(2) 0.62887(8) 0.0235(6) Uani 1 1 d . . . . .
C85 C -0.5249(3) -0.1494(2) 0.60158(8) 0.0247(6) Uani 1 1 d . . . . .
C86 C -0.5433(3) -0.1767(2) 0.64374(9) 0.0272(6) Uani 1 1 d . . . . .
H86 H -0.4648 -0.1457 0.6637 0.033 Uiso 1 1 calc R U . . .
C87 C -0.6771(3) -0.2500(3) 0.65715(10) 0.0361(7) Uani 1 1 d . . . . .
H87 H -0.6895 -0.2684 0.6861 0.043 Uiso 1 1 calc R U . . .
C88 C -0.7907(3) -0.2953(3) 0.62829(12) 0.0416(8) Uani 1 1 d . . . . .
H88 H -0.8818 -0.3448 0.6374 0.050 Uiso 1 1 calc R U . . .
C89 C -0.7728(3) -0.2693(3) 0.58643(12) 0.0435(8) Uani 1 1 d . . . . .
H89 H -0.8514 -0.3014 0.5666 0.052 Uiso 1 1 calc R U . . .
C90 C -0.6410(3) -0.1967(3) 0.57289(10) 0.0344(7) Uani 1 1 d . . . . .
H90 H -0.6297 -0.1790 0.5438 0.041 Uiso 1 1 calc R U . . .


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

# 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
N1 C12 1.139(3) . ?
O1 C11 1.373(3) . ?
O1 C1 1.420(3) . ?
O2 C5 1.216(3) . ?
C1 C12 1.479(3) . ?
C1 C4 1.558(3) . ?
C1 C2 1.558(3) . ?
C2 C13 1.497(3) . ?
C2 C3 1.551(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.544(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.504(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.461(4) . ?
C6 C11 1.396(4) . ?
C6 C7 1.404(4) . ?
C7 C8 1.366(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9500 . ?
C13 C14 1.392(4) . ?
C13 C18 1.392(4) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N2 C30 1.147(3) . ?
O3 C29 1.372(3) . ?
O3 C19 1.425(3) . ?
O4 C23 1.218(3) . ?
C19 C30 1.476(3) . ?
C19 C22 1.553(3) . ?
C19 C20 1.557(3) . ?
C20 C31 1.500(3) . ?
C20 C21 1.546(3) . ?
C20 H20 1.0000 . ?
C21 C22 1.553(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.505(3) . ?
C22 H22 1.0000 . ?
C23 C24 1.469(3) . ?
C24 C29 1.392(3) . ?
C24 C25 1.403(3) . ?
C25 C26 1.375(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.383(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.395(3) . ?
C28 H28 0.9500 . ?
C31 C32 1.390(3) . ?
C31 C36 1.391(3) . ?
C32 C33 1.388(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N3 C48 1.140(3) . ?
O7 C47 1.372(3) . ?
O7 C37 1.426(3) . ?
O8 C41 1.215(3) . ?
C37 C48 1.478(3) . ?
C37 C40 1.552(3) . ?
C37 C38 1.554(3) . ?
C38 C49 1.503(3) . ?
C38 C39 1.548(3) . ?
C38 H38 1.0000 . ?
C39 C40 1.550(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.511(3) . ?
C40 H40 1.0000 . ?
C41 C42 1.473(4) . ?
C42 C47 1.391(4) . ?
C42 C43 1.403(4) . ?
C43 C44 1.378(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.386(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.383(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.394(4) . ?
C46 H46 0.9500 . ?
C49 C54 1.390(4) . ?
C49 C50 1.399(3) . ?
C50 C51 1.383(4) . ?
C50 H50 0.9500 . ?
C51 C52 1.387(4) . ?
C51 H51 0.9500 . ?
C52 C53 1.379(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.390(4) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
N4 C66 1.142(3) . ?
O5 C65 1.375(3) . ?
O5 C55 1.427(3) . ?
C55 C66 1.471(3) . ?
C55 C58 1.548(3) . ?
C55 C56 1.560(3) . ?
C56 C67 1.494(4) . ?
C56 C57 1.545(3) . ?
C56 H56 1.0000 . ?
C57 C58 1.545(4) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 C59 1.514(4) . ?
C58 H58 1.0000 . ?
C59 O6 1.217(3) . ?
C59 C60 1.463(4) . ?
C60 C65 1.383(4) . ?
C60 C61 1.413(4) . ?
C61 C62 1.375(5) . ?
C61 H61 0.9500 . ?
C62 C63 1.375(5) . ?
C62 H62 0.9500 . ?
C63 C64 1.378(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.391(4) . ?
C64 H64 0.9500 . ?
C67 C68 1.391(4) . ?
C67 C72 1.395(4) . ?
C68 C69 1.384(4) . ?
C68 H68 0.9500 . ?
C69 C70 1.388(4) . ?
C69 H69 0.9500 . ?
C70 C71 1.376(5) . ?
C70 H70 0.9500 . ?
C71 C72 1.390(4) . ?
C71 H71 0.9500 . ?
C72 H72 0.9500 . ?
N5 C84 1.140(3) . ?
O9 C83B 1.348(10) . ?
O9 C83A 1.382(4) . ?
O9 C73 1.422(3) . ?
C73 C84 1.475(3) . ?
C73 C76 1.548(4) . ?
C73 C74 1.558(4) . ?
C74 C85 1.500(4) . ?
C74 C75 1.545(4) . ?
C74 H74 1.0000 . ?
C75 C76 1.543(4) . ?
C75 H75A 0.9900 . ?
C75 H75B 0.9900 . ?
C76 C77A 1.459(7) . ?
C76 C77B 1.689(16) . ?
C76 H76 1.0000 . ?
C77A O10A 1.223(4) . ?
C77A C78A 1.472(5) . ?
C78A C79A 1.3900 . ?
C78A C83A 1.3900 . ?
C79A C80A 1.3900 . ?
C79A H79A 0.9500 . ?
C80A C81A 1.3900 . ?
C80A H80A 0.9500 . ?
C81A C82A 1.3900 . ?
C81A H81A 0.9500 . ?
C82A C83A 1.3900 . ?
C82A H82A 0.9500 . ?
C77B O10B 1.221(9) . ?
C77B C78B 1.467(8) . ?
C78B C79B 1.3900 . ?
C78B C83B 1.3900 . ?
C79B C80B 1.3900 . ?
C79B H79B 0.9500 . ?
C80B C81B 1.3900 . ?
C80B H80B 0.9500 . ?
C81B C82B 1.3900 . ?
C81B H81B 0.9500 . ?
C82B C83B 1.3900 . ?
C82B H82B 0.9500 . ?
C85 C86 1.383(4) . ?
C85 C90 1.391(4) . ?
C86 C87 1.398(4) . ?
C86 H86 0.9500 . ?
C87 C88 1.376(5) . ?
C87 H87 0.9500 . ?
C88 C89 1.370(5) . ?
C88 H88 0.9500 . ?
C89 C90 1.383(5) . ?
C89 H89 0.9500 . ?
C90 H90 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
C11 O1 C1 117.65(19) . . ?
O1 C1 C12 104.54(19) . . ?
O1 C1 C4 119.8(2) . . ?
C12 C1 C4 112.7(2) . . ?
O1 C1 C2 118.1(2) . . ?
C12 C1 C2 112.9(2) . . ?
C4 C1 C2 88.84(18) . . ?
C13 C2 C3 119.3(2) . . ?
C13 C2 C1 120.7(2) . . ?
C3 C2 C1 87.90(19) . . ?
C13 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C4 C3 C2 89.63(19) . . ?
C4 C3 H3A 113.7 . . ?
C2 C3 H3A 113.7 . . ?
C4 C3 H3B 113.7 . . ?
C2 C3 H3B 113.7 . . ?
H3A C3 H3B 111.0 . . ?
C5 C4 C3 112.4(2) . . ?
C5 C4 C1 113.7(2) . . ?
C3 C4 C1 88.17(18) . . ?
C5 C4 H4 113.4 . . ?
C3 C4 H4 113.4 . . ?
C1 C4 H4 113.4 . . ?
O2 C5 C6 123.2(2) . . ?
O2 C5 C4 119.0(2) . . ?
C6 C5 C4 117.8(2) . . ?
C11 C6 C7 118.2(2) . . ?
C11 C6 C5 121.7(2) . . ?
C7 C6 C5 120.1(2) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.1(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
O1 C11 C10 115.1(2) . . ?
O1 C11 C6 123.7(2) . . ?
C10 C11 C6 121.2(2) . . ?
N1 C12 C1 179.4(3) . . ?
C14 C13 C18 118.6(2) . . ?
C14 C13 C2 121.2(2) . . ?
C18 C13 C2 120.2(2) . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C29 O3 C19 117.06(18) . . ?
O3 C19 C30 104.32(19) . . ?
O3 C19 C22 119.66(19) . . ?
C30 C19 C22 112.96(19) . . ?
O3 C19 C20 117.70(19) . . ?
C30 C19 C20 113.21(19) . . ?
C22 C19 C20 89.05(17) . . ?
C31 C20 C21 120.5(2) . . ?
C31 C20 C19 120.65(19) . . ?
C21 C20 C19 88.08(17) . . ?
C31 C20 H20 108.6 . . ?
C21 C20 H20 108.6 . . ?
C19 C20 H20 108.6 . . ?
C20 C21 C22 89.46(17) . . ?
C20 C21 H21A 113.7 . . ?
C22 C21 H21A 113.7 . . ?
C20 C21 H21B 113.7 . . ?
C22 C21 H21B 113.7 . . ?
H21A C21 H21B 111.0 . . ?
C23 C22 C19 113.91(19) . . ?
C23 C22 C21 113.0(2) . . ?
C19 C22 C21 87.98(17) . . ?
C23 C22 H22 113.2 . . ?
C19 C22 H22 113.2 . . ?
C21 C22 H22 113.2 . . ?
O4 C23 C24 123.0(2) . . ?
O4 C23 C22 119.2(2) . . ?
C24 C23 C22 117.8(2) . . ?
C29 C24 C25 118.7(2) . . ?
C29 C24 C23 121.3(2) . . ?
C25 C24 C23 120.0(2) . . ?
C26 C25 C24 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 119.5(2) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 119.4(2) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
O3 C29 C24 124.0(2) . . ?
O3 C29 C28 115.2(2) . . ?
C24 C29 C28 120.7(2) . . ?
N2 C30 C19 179.7(3) . . ?
C32 C31 C36 118.9(2) . . ?
C32 C31 C20 120.9(2) . . ?
C36 C31 C20 120.3(2) . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 120.4(2) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 119.3(2) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 120.4(2) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 120.5(2) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C47 O7 C37 117.31(18) . . ?
O7 C37 C48 104.44(19) . . ?
O7 C37 C40 119.7(2) . . ?
C48 C37 C40 112.6(2) . . ?
O7 C37 C38 117.7(2) . . ?
C48 C37 C38 113.5(2) . . ?
C40 C37 C38 88.92(18) . . ?
C49 C38 C39 120.0(2) . . ?
C49 C38 C37 120.5(2) . . ?
C39 C38 C37 88.32(18) . . ?
C49 C38 H38 108.8 . . ?
C39 C38 H38 108.8 . . ?
C37 C38 H38 108.8 . . ?
C38 C39 C40 89.20(18) . . ?
C38 C39 H39A 113.8 . . ?
C40 C39 H39A 113.8 . . ?
C38 C39 H39B 113.8 . . ?
C40 C39 H39B 113.8 . . ?
H39A C39 H39B 111.0 . . ?
C41 C40 C39 112.5(2) . . ?
C41 C40 C37 113.8(2) . . ?
C39 C40 C37 88.30(18) . . ?
C41 C40 H40 113.3 . . ?
C39 C40 H40 113.3 . . ?
C37 C40 H40 113.3 . . ?
O8 C41 C42 122.7(2) . . ?
O8 C41 C40 119.6(2) . . ?
C42 C41 C40 117.6(2) . . ?
C47 C42 C43 118.4(2) . . ?
C47 C42 C41 121.5(2) . . ?
C43 C42 C41 120.1(2) . . ?
C44 C43 C42 120.8(3) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 119.7(3) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C46 C45 C44 120.9(3) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C45 C46 C47 119.0(3) . . ?
C45 C46 H46 120.5 . . ?
C47 C46 H46 120.5 . . ?
O7 C47 C42 123.8(2) . . ?
O7 C47 C46 115.0(2) . . ?
C42 C47 C46 121.1(2) . . ?
N3 C48 C37 179.5(3) . . ?
C54 C49 C50 118.8(2) . . ?
C54 C49 C38 120.4(2) . . ?
C50 C49 C38 120.7(2) . . ?
C51 C50 C49 120.3(3) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 H50 119.8 . . ?
C50 C51 C52 120.3(3) . . ?
C50 C51 H51 119.9 . . ?
C52 C51 H51 119.9 . . ?
C53 C52 C51 119.9(3) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
C52 C53 C54 120.1(3) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C49 C54 C53 120.5(2) . . ?
C49 C54 H54 119.7 . . ?
C53 C54 H54 119.7 . . ?
C65 O5 C55 117.13(19) . . ?
O5 C55 C66 103.65(19) . . ?
O5 C55 C58 119.7(2) . . ?
C66 C55 C58 113.1(2) . . ?
O5 C55 C56 118.61(19) . . ?
C66 C55 C56 113.1(2) . . ?
C58 C55 C56 88.91(18) . . ?
C67 C56 C57 120.4(2) . . ?
C67 C56 C55 121.3(2) . . ?
C57 C56 C55 87.20(19) . . ?
C67 C56 H56 108.7 . . ?
C57 C56 H56 108.7 . . ?
C55 C56 H56 108.7 . . ?
C58 C57 C56 89.56(19) . . ?
C58 C57 H57A 113.7 . . ?
C56 C57 H57A 113.7 . . ?
C58 C57 H57B 113.7 . . ?
C56 C57 H57B 113.7 . . ?
H57A C57 H57B 111.0 . . ?
C59 C58 C57 112.6(2) . . ?
C59 C58 C55 112.9(2) . . ?
C57 C58 C55 87.64(19) . . ?
C59 C58 H58 113.7 . . ?
C57 C58 H58 113.7 . . ?
C55 C58 H58 113.7 . . ?
O6 C59 C60 123.4(3) . . ?
O6 C59 C58 118.8(3) . . ?
C60 C59 C58 117.8(2) . . ?
C65 C60 C61 117.9(3) . . ?
C65 C60 C59 122.0(2) . . ?
C61 C60 C59 120.1(3) . . ?
C62 C61 C60 120.4(3) . . ?
C62 C61 H61 119.8 . . ?
C60 C61 H61 119.8 . . ?
C61 C62 C63 120.4(3) . . ?
C61 C62 H62 119.8 . . ?
C63 C62 H62 119.8 . . ?
C62 C63 C64 120.7(3) . . ?
C62 C63 H63 119.7 . . ?
C64 C63 H63 119.7 . . ?
C63 C64 C65 119.1(3) . . ?
C63 C64 H64 120.4 . . ?
C65 C64 H64 120.4 . . ?
O5 C65 C60 123.5(2) . . ?
O5 C65 C64 114.9(2) . . ?
C60 C65 C64 121.5(2) . . ?
N4 C66 C55 178.7(3) . . ?
C68 C67 C72 118.6(2) . . ?
C68 C67 C56 121.0(2) . . ?
C72 C67 C56 120.3(2) . . ?
C69 C68 C67 120.7(3) . . ?
C69 C68 H68 119.7 . . ?
C67 C68 H68 119.7 . . ?
C68 C69 C70 120.0(3) . . ?
C68 C69 H69 120.0 . . ?
C70 C69 H69 120.0 . . ?
C71 C70 C69 120.0(3) . . ?
C71 C70 H70 120.0 . . ?
C69 C70 H70 120.0 . . ?
C70 C71 C72 120.0(3) . . ?
C70 C71 H71 120.0 . . ?
C72 C71 H71 120.0 . . ?
C71 C72 C67 120.6(3) . . ?
C71 C72 H72 119.7 . . ?
C67 C72 H72 119.7 . . ?
C83B O9 C73 124.9(6) . . ?
C83A O9 C73 114.3(4) . . ?
O9 C73 C84 104.0(2) . . ?
O9 C73 C76 119.9(2) . . ?
C84 C73 C76 112.7(2) . . ?
O9 C73 C74 118.7(2) . . ?
C84 C73 C74 113.1(2) . . ?
C76 C73 C74 88.46(19) . . ?
C85 C74 C75 119.8(2) . . ?
C85 C74 C73 120.9(2) . . ?
C75 C74 C73 87.8(2) . . ?
C85 C74 H74 108.8 . . ?
C75 C74 H74 108.8 . . ?
C73 C74 H74 108.8 . . ?
C76 C75 C74 89.1(2) . . ?
C76 C75 H75A 113.8 . . ?
C74 C75 H75A 113.8 . . ?
C76 C75 H75B 113.8 . . ?
C74 C75 H75B 113.8 . . ?
H75A C75 H75B 111.0 . . ?
C77A C76 C75 110.7(4) . . ?
C77A C76 C73 115.7(4) . . ?
C75 C76 C73 88.2(2) . . ?
C75 C76 C77B 117.0(9) . . ?
C73 C76 C77B 106.5(5) . . ?
C77A C76 H76 113.3 . . ?
C75 C76 H76 113.3 . . ?
C73 C76 H76 113.3 . . ?
O10A C77A C76 119.9(5) . . ?
O10A C77A C78A 123.6(4) . . ?
C76 C77A C78A 116.5(3) . . ?
C79A C78A C83A 120.0 . . ?
C79A C78A C77A 119.1(2) . . ?
C83A C78A C77A 120.8(2) . . ?
C78A C79A C80A 120.0 . . ?
C78A C79A H79A 120.0 . . ?
C80A C79A H79A 120.0 . . ?
C81A C80A C79A 120.0 . . ?
C81A C80A H80A 120.0 . . ?
C79A C80A H80A 120.0 . . ?
C80A C81A C82A 120.0 . . ?
C80A C81A H81A 120.0 . . ?
C82A C81A H81A 120.0 . . ?
C83A C82A C81A 120.0 . . ?
C83A C82A H82A 120.0 . . ?
C81A C82A H82A 120.0 . . ?
O9 C83A C82A 113.9(3) . . ?
O9 C83A C78A 126.1(3) . . ?
C82A C83A C78A 120.0 . . ?
O10B C77B C78B 124.6(11) . . ?
O10B C77B C76 114.3(11) . . ?
C78B C77B C76 120.6(9) . . ?
C79B C78B C83B 120.0 . . ?
C79B C78B C77B 119.4(7) . . ?
C83B C78B C77B 120.4(7) . . ?
C78B C79B C80B 120.0 . . ?
C78B C79B H79B 120.0 . . ?
C80B C79B H79B 120.0 . . ?
C81B C80B C79B 120.0 . . ?
C81B C80B H80B 120.0 . . ?
C79B C80B H80B 120.0 . . ?
C80B C81B C82B 120.0 . . ?
C80B C81B H81B 120.0 . . ?
C82B C81B H81B 120.0 . . ?
C83B C82B C81B 120.0 . . ?
C83B C82B H82B 120.0 . . ?
C81B C82B H82B 120.0 . . ?
O9 C83B C82B 119.2(8) . . ?
O9 C83B C78B 120.8(8) . . ?
C82B C83B C78B 120.0 . . ?
N5 C84 C73 177.9(3) . . ?
C86 C85 C90 118.9(3) . . ?
C86 C85 C74 121.2(2) . . ?
C90 C85 C74 119.9(3) . . ?
C85 C86 C87 120.2(3) . . ?
C85 C86 H86 119.9 . . ?
C87 C86 H86 119.9 . . ?
C88 C87 C86 119.9(3) . . ?
C88 C87 H87 120.1 . . ?
C86 C87 H87 120.1 . . ?
C89 C88 C87 120.1(3) . . ?
C89 C88 H88 119.9 . . ?
C87 C88 H88 119.9 . . ?
C88 C89 C90 120.4(3) . . ?
C88 C89 H89 119.8 . . ?
C90 C89 H89 119.8 . . ?
C89 C90 C85 120.4(3) . . ?
C89 C90 H90 119.8 . . ?
C85 C90 H90 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
C11 O1 C1 C12 -155.4(2) . . . . ?
C11 O1 C1 C4 -28.0(3) . . . . ?
C11 O1 C1 C2 78.2(3) . . . . ?
O1 C1 C2 C13 95.9(3) . . . . ?
C12 C1 C2 C13 -26.4(3) . . . . ?
C4 C1 C2 C13 -140.6(2) . . . . ?
O1 C1 C2 C3 -141.0(2) . . . . ?
C12 C1 C2 C3 96.7(2) . . . . ?
C4 C1 C2 C3 -17.45(18) . . . . ?
C13 C2 C3 C4 142.0(2) . . . . ?
C1 C2 C3 C4 17.61(18) . . . . ?
C2 C3 C4 C5 97.3(2) . . . . ?
C2 C3 C4 C1 -17.61(19) . . . . ?
O1 C1 C4 C5 25.8(3) . . . . ?
C12 C1 C4 C5 149.3(2) . . . . ?
C2 C1 C4 C5 -96.2(2) . . . . ?
O1 C1 C4 C3 139.6(2) . . . . ?
C12 C1 C4 C3 -96.9(2) . . . . ?
C2 C1 C4 C3 17.52(18) . . . . ?
C3 C4 C5 O2 71.2(3) . . . . ?
C1 C4 C5 O2 169.4(2) . . . . ?
C3 C4 C5 C6 -109.1(2) . . . . ?
C1 C4 C5 C6 -10.9(3) . . . . ?
O2 C5 C6 C11 178.5(2) . . . . ?
C4 C5 C6 C11 -1.2(3) . . . . ?
O2 C5 C6 C7 -1.3(4) . . . . ?
C4 C5 C6 C7 179.0(2) . . . . ?
C11 C6 C7 C8 -0.6(4) . . . . ?
C5 C6 C7 C8 179.2(2) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C1 O1 C11 C10 -166.9(2) . . . . ?
C1 O1 C11 C6 14.9(3) . . . . ?
C9 C10 C11 O1 -179.9(2) . . . . ?
C9 C10 C11 C6 -1.6(4) . . . . ?
C7 C6 C11 O1 179.8(2) . . . . ?
C5 C6 C11 O1 0.0(4) . . . . ?
C7 C6 C11 C10 1.7(4) . . . . ?
C5 C6 C11 C10 -178.1(2) . . . . ?
C3 C2 C13 C14 -156.6(2) . . . . ?
C1 C2 C13 C14 -50.1(3) . . . . ?
C3 C2 C13 C18 24.4(4) . . . . ?
C1 C2 C13 C18 130.9(3) . . . . ?
C18 C13 C14 C15 -1.2(4) . . . . ?
C2 C13 C14 C15 179.8(2) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C13 0.2(4) . . . . ?
C14 C13 C18 C17 0.8(4) . . . . ?
C2 C13 C18 C17 179.9(2) . . . . ?
C29 O3 C19 C30 157.86(19) . . . . ?
C29 O3 C19 C22 30.4(3) . . . . ?
C29 O3 C19 C20 -75.7(3) . . . . ?
O3 C19 C20 C31 -94.4(2) . . . . ?
C30 C19 C20 C31 27.6(3) . . . . ?
C22 C19 C20 C31 142.2(2) . . . . ?
O3 C19 C20 C21 140.9(2) . . . . ?
C30 C19 C20 C21 -97.2(2) . . . . ?
C22 C19 C20 C21 17.51(17) . . . . ?
C31 C20 C21 C22 -142.4(2) . . . . ?
C19 C20 C21 C22 -17.51(17) . . . . ?
O3 C19 C22 C23 -24.8(3) . . . . ?
C30 C19 C22 C23 -148.2(2) . . . . ?
C20 C19 C22 C23 96.9(2) . . . . ?
O3 C19 C22 C21 -139.1(2) . . . . ?
C30 C19 C22 C21 97.5(2) . . . . ?
C20 C19 C22 C21 -17.43(17) . . . . ?
C20 C21 C22 C23 -97.6(2) . . . . ?
C20 C21 C22 C19 17.56(17) . . . . ?
C19 C22 C23 O4 -171.5(2) . . . . ?
C21 C22 C23 O4 -73.1(3) . . . . ?
C19 C22 C23 C24 7.9(3) . . . . ?
C21 C22 C23 C24 106.3(2) . . . . ?
O4 C23 C24 C29 -177.6(2) . . . . ?
C22 C23 C24 C29 3.0(3) . . . . ?
O4 C23 C24 C25 2.5(4) . . . . ?
C22 C23 C24 C25 -176.9(2) . . . . ?
C29 C24 C25 C26 -0.7(4) . . . . ?
C23 C24 C25 C26 179.2(2) . . . . ?
C24 C25 C26 C27 1.1(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C27 C28 C29 -0.9(4) . . . . ?
C19 O3 C29 C24 -18.8(3) . . . . ?
C19 O3 C29 C28 163.3(2) . . . . ?
C25 C24 C29 O3 -178.2(2) . . . . ?
C23 C24 C29 O3 1.9(4) . . . . ?
C25 C24 C29 C28 -0.5(3) . . . . ?
C23 C24 C29 C28 179.7(2) . . . . ?
C27 C28 C29 O3 179.1(2) . . . . ?
C27 C28 C29 C24 1.2(4) . . . . ?
C21 C20 C31 C32 158.6(2) . . . . ?
C19 C20 C31 C32 51.0(3) . . . . ?
C21 C20 C31 C36 -22.6(3) . . . . ?
C19 C20 C31 C36 -130.3(2) . . . . ?
C36 C31 C32 C33 0.9(4) . . . . ?
C20 C31 C32 C33 179.7(2) . . . . ?
C31 C32 C33 C34 -1.1(4) . . . . ?
C32 C33 C34 C35 0.0(4) . . . . ?
C33 C34 C35 C36 1.1(4) . . . . ?
C34 C35 C36 C31 -1.2(4) . . . . ?
C32 C31 C36 C35 0.2(3) . . . . ?
C20 C31 C36 C35 -178.6(2) . . . . ?
C47 O7 C37 C48 -157.3(2) . . . . ?
C47 O7 C37 C40 -30.1(3) . . . . ?
C47 O7 C37 C38 75.9(3) . . . . ?
O7 C37 C38 C49 95.1(3) . . . . ?
C48 C37 C38 C49 -27.2(3) . . . . ?
C40 C37 C38 C49 -141.5(2) . . . . ?
O7 C37 C38 C39 -140.6(2) . . . . ?
C48 C37 C38 C39 97.0(2) . . . . ?
C40 C37 C38 C39 -17.22(18) . . . . ?
C49 C38 C39 C40 141.9(2) . . . . ?
C37 C38 C39 C40 17.24(18) . . . . ?
C38 C39 C40 C41 97.9(2) . . . . ?
C38 C39 C40 C37 -17.26(18) . . . . ?
O7 C37 C40 C41 24.9(3) . . . . ?
C48 C37 C40 C41 148.2(2) . . . . ?
C38 C37 C40 C41 -96.7(2) . . . . ?
O7 C37 C40 C39 138.8(2) . . . . ?
C48 C37 C40 C39 -97.9(2) . . . . ?
C38 C37 C40 C39 17.20(18) . . . . ?
C39 C40 C41 O8 73.2(3) . . . . ?
C37 C40 C41 O8 171.7(2) . . . . ?
C39 C40 C41 C42 -106.7(3) . . . . ?
C37 C40 C41 C42 -8.2(3) . . . . ?
O8 C41 C42 C47 177.2(3) . . . . ?
C40 C41 C42 C47 -2.9(4) . . . . ?
O8 C41 C42 C43 -2.6(4) . . . . ?
C40 C41 C42 C43 177.3(2) . . . . ?
C47 C42 C43 C44 0.9(4) . . . . ?
C41 C42 C43 C44 -179.3(2) . . . . ?
C42 C43 C44 C45 -1.5(4) . . . . ?
C43 C44 C45 C46 0.7(4) . . . . ?
C44 C45 C46 C47 0.7(4) . . . . ?
C37 O7 C47 C42 18.3(3) . . . . ?
C37 O7 C47 C46 -163.8(2) . . . . ?
C43 C42 C47 O7 178.2(2) . . . . ?
C41 C42 C47 O7 -1.6(4) . . . . ?
C43 C42 C47 C46 0.5(4) . . . . ?
C41 C42 C47 C46 -179.3(2) . . . . ?
C45 C46 C47 O7 -179.2(2) . . . . ?
C45 C46 C47 C42 -1.3(4) . . . . ?
C39 C38 C49 C54 22.1(3) . . . . ?
C37 C38 C49 C54 129.6(3) . . . . ?
C39 C38 C49 C50 -159.9(2) . . . . ?
C37 C38 C49 C50 -52.4(3) . . . . ?
C54 C49 C50 C51 -1.3(4) . . . . ?
C38 C49 C50 C51 -179.4(2) . . . . ?
C49 C50 C51 C52 0.6(4) . . . . ?
C50 C51 C52 C53 0.7(4) . . . . ?
C51 C52 C53 C54 -1.2(4) . . . . ?
C50 C49 C54 C53 0.8(4) . . . . ?
C38 C49 C54 C53 178.9(2) . . . . ?
C52 C53 C54 C49 0.4(4) . . . . ?
C65 O5 C55 C66 -158.4(2) . . . . ?
C65 O5 C55 C58 -31.3(3) . . . . ?
C65 O5 C55 C56 75.3(3) . . . . ?
O5 C55 C56 C67 92.8(3) . . . . ?
C66 C55 C56 C67 -28.9(3) . . . . ?
C58 C55 C56 C67 -143.6(2) . . . . ?
O5 C55 C56 C57 -143.0(2) . . . . ?
C66 C55 C56 C57 95.4(2) . . . . ?
C58 C55 C56 C57 -19.34(19) . . . . ?
C67 C56 C57 C58 144.4(2) . . . . ?
C55 C56 C57 C58 19.38(19) . . . . ?
C56 C57 C58 C59 94.3(2) . . . . ?
C56 C57 C58 C55 -19.53(19) . . . . ?
O5 C55 C58 C59 28.4(3) . . . . ?
C66 C55 C58 C59 151.0(2) . . . . ?
C56 C55 C58 C59 -94.3(2) . . . . ?
O5 C55 C58 C57 142.0(2) . . . . ?
C66 C55 C58 C57 -95.4(2) . . . . ?
C56 C55 C58 C57 19.34(19) . . . . ?
C57 C58 C59 O6 71.8(3) . . . . ?
C55 C58 C59 O6 169.2(2) . . . . ?
C57 C58 C59 C60 -108.9(3) . . . . ?
C55 C58 C59 C60 -11.5(3) . . . . ?
O6 C59 C60 C65 177.4(3) . . . . ?
C58 C59 C60 C65 -1.9(4) . . . . ?
O6 C59 C60 C61 -2.9(4) . . . . ?
C58 C59 C60 C61 177.9(2) . . . . ?
C65 C60 C61 C62 -1.0(4) . . . . ?
C59 C60 C61 C62 179.3(2) . . . . ?
C60 C61 C62 C63 -0.9(4) . . . . ?
C61 C62 C63 C64 1.7(5) . . . . ?
C62 C63 C64 C65 -0.5(4) . . . . ?
C55 O5 C65 C60 16.7(3) . . . . ?
C55 O5 C65 C64 -165.1(2) . . . . ?
C61 C60 C65 O5 -179.7(2) . . . . ?
C59 C60 C65 O5 0.0(4) . . . . ?
C61 C60 C65 C64 2.2(4) . . . . ?
C59 C60 C65 C64 -178.1(2) . . . . ?
C63 C64 C65 O5 -179.8(2) . . . . ?
C63 C64 C65 C60 -1.5(4) . . . . ?
C57 C56 C67 C68 -159.0(2) . . . . ?
C55 C56 C67 C68 -52.2(3) . . . . ?
C57 C56 C67 C72 23.0(3) . . . . ?
C55 C56 C67 C72 129.8(2) . . . . ?
C72 C67 C68 C69 -0.6(4) . . . . ?
C56 C67 C68 C69 -178.6(2) . . . . ?
C67 C68 C69 C70 0.3(4) . . . . ?
C68 C69 C70 C71 0.1(4) . . . . ?
C69 C70 C71 C72 -0.4(4) . . . . ?
C70 C71 C72 C67 0.1(4) . . . . ?
C68 C67 C72 C71 0.4(4) . . . . ?
C56 C67 C72 C71 178.4(2) . . . . ?
C83B O9 C73 C84 -159.2(12) . . . . ?
C83A O9 C73 C84 -155.8(3) . . . . ?
C83B O9 C73 C76 -32.1(12) . . . . ?
C83A O9 C73 C76 -28.7(4) . . . . ?
C83B O9 C73 C74 74.1(12) . . . . ?
C83A O9 C73 C74 77.5(4) . . . . ?
O9 C73 C74 C85 93.5(3) . . . . ?
C84 C73 C74 C85 -28.8(3) . . . . ?
C76 C73 C74 C85 -142.9(2) . . . . ?
O9 C73 C74 C75 -142.8(2) . . . . ?
C84 C73 C74 C75 95.0(2) . . . . ?
C76 C73 C74 C75 -19.1(2) . . . . ?
C85 C74 C75 C76 143.9(2) . . . . ?
C73 C74 C75 C76 19.1(2) . . . . ?
C74 C75 C76 C77A 97.6(4) . . . . ?
C74 C75 C76 C73 -19.3(2) . . . . ?
C74 C75 C76 C77B 88.4(6) . . . . ?
O9 C73 C76 C77A 29.5(5) . . . . ?
C84 C73 C76 C77A 152.5(4) . . . . ?
C74 C73 C76 C77A -93.1(4) . . . . ?
O9 C73 C76 C75 141.7(2) . . . . ?
C84 C73 C76 C75 -95.3(2) . . . . ?
C74 C73 C76 C75 19.1(2) . . . . ?
O9 C73 C76 C77B 24.1(10) . . . . ?
C84 C73 C76 C77B 147.0(9) . . . . ?
C74 C73 C76 C77B -98.5(9) . . . . ?
C75 C76 C77A O10A 69.4(7) . . . . ?
C73 C76 C77A O10A 167.6(5) . . . . ?
C75 C76 C77A C78A -111.4(5) . . . . ?
C73 C76 C77A C78A -13.1(7) . . . . ?
O10A C77A C78A C79A -0.5(9) . . . . ?
C76 C77A C78A C79A -179.7(4) . . . . ?
O10A C77A C78A C83A 177.7(6) . . . . ?
C76 C77A C78A C83A -1.5(7) . . . . ?
C83A C78A C79A C80A 0.0 . . . . ?
C77A C78A C79A C80A 178.2(5) . . . . ?
C78A C79A C80A C81A 0.0 . . . . ?
C79A C80A C81A C82A 0.0 . . . . ?
C80A C81A C82A C83A 0.0 . . . . ?
C73 O9 C83A C82A -166.5(2) . . . . ?
C73 O9 C83A C78A 13.3(5) . . . . ?
C81A C82A C83A O9 179.8(5) . . . . ?
C81A C82A C83A C78A 0.0 . . . . ?
C79A C78A C83A O9 -179.7(6) . . . . ?
C77A C78A C83A O9 2.1(5) . . . . ?
C79A C78A C83A C82A 0.0 . . . . ?
C77A C78A C83A C82A -178.2(5) . . . . ?
C75 C76 C77B O10B 71(2) . . . . ?
C73 C76 C77B O10B 167.8(18) . . . . ?
C75 C76 C77B C78B -101(2) . . . . ?
C73 C76 C77B C78B -5(2) . . . . ?
O10B C77B C78B C79B 3(3) . . . . ?
C76 C77B C78B C79B 174.6(13) . . . . ?
O10B C77B C78B C83B 178(2) . . . . ?
C76 C77B C78B C83B -10(3) . . . . ?
C83B C78B C79B C80B 0.0 . . . . ?
C77B C78B C79B C80B 175(2) . . . . ?
C78B C79B C80B C81B 0.0 . . . . ?
C79B C80B C81B C82B 0.0 . . . . ?
C80B C81B C82B C83B 0.0 . . . . ?
C73 O9 C83B C82B -163.5(6) . . . . ?
C73 O9 C83B C78B 14.3(17) . . . . ?
C81B C82B C83B O9 177.8(19) . . . . ?
C81B C82B C83B C78B 0.0 . . . . ?
C79B C78B C83B O9 -177.8(19) . . . . ?
C77B C78B C83B O9 7.3(17) . . . . ?
C79B C78B C83B C82B 0.0 . . . . ?
C77B C78B C83B C82B -175(2) . . . . ?
C75 C74 C85 C86 -156.0(2) . . . . ?
C73 C74 C85 C86 -49.2(3) . . . . ?
C75 C74 C85 C90 24.9(4) . . . . ?
C73 C74 C85 C90 131.8(3) . . . . ?
C90 C85 C86 C87 -0.5(4) . . . . ?
C74 C85 C86 C87 -179.6(2) . . . . ?
C85 C86 C87 C88 0.2(4) . . . . ?
C86 C87 C88 C89 0.3(4) . . . . ?
C87 C88 C89 C90 -0.5(5) . . . . ?
C88 C89 C90 C85 0.2(4) . . . . ?
C86 C85 C90 C89 0.3(4) . . . . ?
C74 C85 C90 C89 179.4(3) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_is_rd242cf1
_database_code_depnum_ccdc_archive 'CCDC 2250463'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl N O2'
_chemical_formula_sum            'C18 H12 Cl N O2'
_chemical_formula_weight         309.74

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'

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

# 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'

_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                   8.0634(10)
_cell_length_b                   9.8825(12)
_cell_length_c                   10.1049(13)
_cell_angle_alpha                114.137(4)
_cell_angle_beta                 98.043(5)
_cell_angle_gamma                97.708(4)
_cell_volume                     711.10(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6564
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      31.87

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.275
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS-2016/2; Sheldrick, 2015)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            24788
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         30.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4529
_reflns_number_gt                3581
_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       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.2377P] 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         4529
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# 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 0.80286(4) 0.03969(4) 0.91916(4) 0.02718(9) Uani 1 1 d . . . . .
O1 O 0.29088(11) 0.43853(10) 0.58762(10) 0.02110(19) Uani 1 1 d . . . . .
O2 O -0.11553(13) 0.56891(12) 0.78625(13) 0.0322(2) Uani 1 1 d . . . . .
N1 N 0.19826(16) 0.06692(13) 0.47441(13) 0.0282(2) Uani 1 1 d . . . . .
C1 C 0.21005(15) 0.35075(13) 0.65169(13) 0.0169(2) Uani 1 1 d . . . . .
C2 C 0.28362(15) 0.38983(13) 0.81709(13) 0.0170(2) Uani 1 1 d . . . . .
H2 H 0.3262 0.5021 0.8742 0.020 Uiso 1 1 calc R U . . .
C3 C 0.09707(15) 0.34718(14) 0.83109(14) 0.0197(2) Uani 1 1 d . . . . .
H3A H 0.0690 0.4194 0.9227 0.024 Uiso 1 1 calc R U . . .
H3B H 0.0630 0.2414 0.8171 0.024 Uiso 1 1 calc R U . . .
C4 C 0.03299(15) 0.37088(13) 0.69101(13) 0.0175(2) Uani 1 1 d . . . . .
H4 H -0.0642 0.2882 0.6178 0.021 Uiso 1 1 calc R U . . .
C5 C 0.00172(16) 0.52813(14) 0.72673(14) 0.0199(2) Uani 1 1 d . . . . .
C6 C 0.11792(16) 0.62682(13) 0.68613(13) 0.0188(2) Uani 1 1 d . . . . .
C7 C 0.09157(18) 0.77236(14) 0.71237(14) 0.0233(3) Uani 1 1 d . . . . .
H7 H -0.0042 0.8046 0.7516 0.028 Uiso 1 1 calc R U . . .
C8 C 0.20301(19) 0.86923(14) 0.68194(15) 0.0264(3) Uani 1 1 d . . . . .
H8 H 0.1838 0.9674 0.6999 0.032 Uiso 1 1 calc R U . . .
C9 C 0.34371(19) 0.82241(15) 0.62476(15) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.4212 0.8898 0.6052 0.032 Uiso 1 1 calc R U . . .
C10 C 0.37205(17) 0.67888(15) 0.59604(14) 0.0230(3) Uani 1 1 d . . . . .
H10 H 0.4679 0.6474 0.5566 0.028 Uiso 1 1 calc R U . . .
C11 C 0.25790(15) 0.58115(13) 0.62577(13) 0.0182(2) Uani 1 1 d . . . . .
C12 C 0.20505(16) 0.19117(14) 0.55040(13) 0.0195(2) Uani 1 1 d . . . . .
C13 C 0.41825(14) 0.31107(13) 0.85203(13) 0.0164(2) Uani 1 1 d . . . . .
C14 C 0.55015(16) 0.28948(15) 0.77438(14) 0.0212(2) Uani 1 1 d . . . . .
H14 H 0.5585 0.3318 0.7058 0.025 Uiso 1 1 calc R U . . .
C15 C 0.66911(15) 0.20718(15) 0.79587(14) 0.0214(2) Uani 1 1 d . . . . .
H15 H 0.7561 0.1900 0.7402 0.026 Uiso 1 1 calc R U . . .
C16 C 0.65893(15) 0.15045(13) 0.89990(14) 0.0195(2) Uani 1 1 d . . . . .
C17 C 0.53513(16) 0.17706(13) 0.98461(13) 0.0193(2) Uani 1 1 d . . . . .
H17 H 0.5334 0.1421 1.0592 0.023 Uiso 1 1 calc R U . . .
C18 C 0.41334(15) 0.25582(13) 0.95850(13) 0.0184(2) Uani 1 1 d . . . . .
H18 H 0.3260 0.2721 1.0139 0.022 Uiso 1 1 calc R U . . .


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

# 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 C16 1.7421(12) . ?
O1 C11 1.3750(14) . ?
O1 C1 1.4221(14) . ?
O2 C5 1.2170(15) . ?
N1 C12 1.1399(17) . ?
C1 C12 1.4790(17) . ?
C1 C4 1.5512(16) . ?
C1 C2 1.5581(17) . ?
C2 C13 1.5010(16) . ?
C2 C3 1.5487(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5571(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5102(16) . ?
C4 H4 1.0000 . ?
C5 C6 1.4789(17) . ?
C6 C11 1.3978(17) . ?
C6 C7 1.4035(17) . ?
C7 C8 1.3805(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3847(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3951(17) . ?
C10 H10 0.9500 . ?
C13 C18 1.3942(16) . ?
C13 C14 1.3963(17) . ?
C14 C15 1.3871(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3856(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3871(17) . ?
C17 C18 1.3929(17) . ?
C17 H17 0.9500 . ?
C18 H18 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
C11 O1 C1 116.90(9) . . ?
O1 C1 C12 105.27(9) . . ?
O1 C1 C4 120.52(9) . . ?
C12 C1 C4 111.12(10) . . ?
O1 C1 C2 118.36(10) . . ?
C12 C1 C2 112.51(9) . . ?
C4 C1 C2 88.71(9) . . ?
C13 C2 C3 120.85(10) . . ?
C13 C2 C1 118.95(10) . . ?
C3 C2 C1 87.59(9) . . ?
C13 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C2 C3 C4 88.84(9) . . ?
C2 C3 H3A 113.8 . . ?
C4 C3 H3A 113.8 . . ?
C2 C3 H3B 113.8 . . ?
C4 C3 H3B 113.8 . . ?
H3A C3 H3B 111.1 . . ?
C5 C4 C1 113.15(10) . . ?
C5 C4 C3 113.57(10) . . ?
C1 C4 C3 87.54(9) . . ?
C5 C4 H4 113.4 . . ?
C1 C4 H4 113.4 . . ?
C3 C4 H4 113.4 . . ?
O2 C5 C6 122.68(11) . . ?
O2 C5 C4 120.03(11) . . ?
C6 C5 C4 117.29(10) . . ?
C11 C6 C7 118.42(11) . . ?
C11 C6 C5 121.79(11) . . ?
C7 C6 C5 119.77(11) . . ?
C8 C7 C6 120.83(13) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.73(12) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.80(12) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.10(13) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
O1 C11 C10 115.34(11) . . ?
O1 C11 C6 123.53(11) . . ?
C10 C11 C6 121.09(11) . . ?
N1 C12 C1 178.10(14) . . ?
C18 C13 C14 118.83(11) . . ?
C18 C13 C2 121.61(10) . . ?
C14 C13 C2 119.55(10) . . ?
C15 C14 C13 121.01(11) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 118.92(11) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.43(11) . . ?
C15 C16 Cl1 118.32(10) . . ?
C17 C16 Cl1 120.24(10) . . ?
C16 C17 C18 118.93(11) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 120.74(11) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?

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
C11 O1 C1 C12 156.98(10) . . . . ?
C11 O1 C1 C4 30.51(15) . . . . ?
C11 O1 C1 C2 -76.26(13) . . . . ?
O1 C1 C2 C13 -91.01(12) . . . . ?
C12 C1 C2 C13 32.20(14) . . . . ?
C4 C1 C2 C13 144.58(10) . . . . ?
O1 C1 C2 C3 144.72(10) . . . . ?
C12 C1 C2 C3 -92.08(10) . . . . ?
C4 C1 C2 C3 20.30(8) . . . . ?
C13 C2 C3 C4 -142.85(11) . . . . ?
C1 C2 C3 C4 -20.22(8) . . . . ?
O1 C1 C4 C5 -28.13(15) . . . . ?
C12 C1 C4 C5 -151.86(10) . . . . ?
C2 C1 C4 C5 94.44(10) . . . . ?
O1 C1 C4 C3 -142.76(11) . . . . ?
C12 C1 C4 C3 93.50(10) . . . . ?
C2 C1 C4 C3 -20.19(8) . . . . ?
C2 C3 C4 C5 -93.93(11) . . . . ?
C2 C3 C4 C1 20.32(8) . . . . ?
C1 C4 C5 O2 -166.01(11) . . . . ?
C3 C4 C5 O2 -68.22(15) . . . . ?
C1 C4 C5 C6 14.14(15) . . . . ?
C3 C4 C5 C6 111.94(12) . . . . ?
O2 C5 C6 C11 176.19(12) . . . . ?
C4 C5 C6 C11 -3.97(17) . . . . ?
O2 C5 C6 C7 -1.86(19) . . . . ?
C4 C5 C6 C7 177.98(11) . . . . ?
C11 C6 C7 C8 -1.20(18) . . . . ?
C5 C6 C7 C8 176.92(11) . . . . ?
C6 C7 C8 C9 -0.13(19) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C8 C9 C10 C11 -0.29(19) . . . . ?
C1 O1 C11 C10 163.05(10) . . . . ?
C1 O1 C11 C6 -18.83(16) . . . . ?
C9 C10 C11 O1 177.08(11) . . . . ?
C9 C10 C11 C6 -1.10(19) . . . . ?
C7 C6 C11 O1 -176.20(11) . . . . ?
C5 C6 C11 O1 5.72(18) . . . . ?
C7 C6 C11 C10 1.83(18) . . . . ?
C5 C6 C11 C10 -176.25(11) . . . . ?
C3 C2 C13 C18 -30.94(16) . . . . ?
C1 C2 C13 C18 -136.87(11) . . . . ?
C3 C2 C13 C14 147.76(11) . . . . ?
C1 C2 C13 C14 41.83(15) . . . . ?
C18 C13 C14 C15 3.65(18) . . . . ?
C2 C13 C14 C15 -175.08(11) . . . . ?
C13 C14 C15 C16 -2.18(19) . . . . ?
C14 C15 C16 C17 -1.41(19) . . . . ?
C14 C15 C16 Cl1 176.97(10) . . . . ?
C15 C16 C17 C18 3.39(18) . . . . ?
Cl1 C16 C17 C18 -174.95(9) . . . . ?
C16 C17 C18 C13 -1.84(18) . . . . ?
C14 C13 C18 C17 -1.61(18) . . . . ?
C2 C13 C18 C17 177.10(11) . . . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_is_rd242e
_database_code_depnum_ccdc_archive 'CCDC 2250462'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O3'
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32

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'

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

# CRYSTAL DATA

_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                   14.6451(9)
_cell_length_b                   6.3929(4)
_cell_length_c                   17.5863(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.361(2)
_cell_angle_gamma                90
_cell_volume                     1522.70(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      29.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS-2016/2; Sheldrick, 2015)'

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

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            56595
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4048
_reflns_number_gt                3300
_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       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

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

# REFINEMENT DATA 

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.6192P] 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         4048
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# 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 0.63002(6) 0.04206(13) 0.35043(5) 0.02164(19) Uani 1 1 d . . . . .
O2 O 0.69079(8) 0.48213(16) 0.20276(6) 0.0331(2) Uani 1 1 d . . . . .
O3 O 0.61242(7) 0.48362(16) 0.71916(6) 0.0311(2) Uani 1 1 d . . . . .
N1 N 0.83151(9) 0.04486(18) 0.51654(7) 0.0320(3) Uani 1 1 d . . . . .
C1 C 0.69401(8) 0.21230(17) 0.38831(7) 0.0185(2) Uani 1 1 d . . . . .
C2 C 0.64652(9) 0.41092(18) 0.40955(7) 0.0193(2) Uani 1 1 d . . . . .
H2 H 0.5786 0.4289 0.3667 0.023 Uiso 1 1 calc R U . . .
C3 C 0.71927(9) 0.54408(18) 0.38496(7) 0.0214(2) Uani 1 1 d . . . . .
H3A H 0.6879 0.6643 0.3490 0.026 Uiso 1 1 calc R U . . .
H3B H 0.7787 0.5888 0.4322 0.026 Uiso 1 1 calc R U . . .
C4 C 0.73688(8) 0.35320(17) 0.33811(7) 0.0185(2) Uani 1 1 d . . . . .
H4 H 0.8084 0.3262 0.3504 0.022 Uiso 1 1 calc R U . . .
C5 C 0.67440(9) 0.35427(18) 0.24731(7) 0.0206(2) Uani 1 1 d . . . . .
C6 C 0.59787(9) 0.19356(19) 0.21512(7) 0.0204(2) Uani 1 1 d . . . . .
C7 C 0.54334(10) 0.1800(2) 0.13019(8) 0.0271(3) Uani 1 1 d . . . . .
H7 H 0.5518 0.2832 0.0946 0.032 Uiso 1 1 calc R U . . .
C8 C 0.47765(10) 0.0185(2) 0.09790(8) 0.0329(3) Uani 1 1 d . . . . .
H8 H 0.4409 0.0108 0.0403 0.040 Uiso 1 1 calc R U . . .
C9 C 0.46537(10) -0.1335(2) 0.15007(8) 0.0312(3) Uani 1 1 d . . . . .
H9 H 0.4214 -0.2468 0.1276 0.037 Uiso 1 1 calc R U . . .
C10 C 0.51652(9) -0.1212(2) 0.23423(8) 0.0251(3) Uani 1 1 d . . . . .
H10 H 0.5070 -0.2239 0.2696 0.030 Uiso 1 1 calc R U . . .
C11 C 0.58218(8) 0.04354(18) 0.26652(7) 0.0196(2) Uani 1 1 d . . . . .
C12 C 0.77209(9) 0.11863(18) 0.46074(7) 0.0219(2) Uani 1 1 d . . . . .
C13 C 0.64127(8) 0.43235(18) 0.49282(7) 0.0203(2) Uani 1 1 d . . . . .
C14 C 0.58987(9) 0.2853(2) 0.51990(8) 0.0245(3) Uani 1 1 d . . . . .
H14 H 0.5597 0.1694 0.4858 0.029 Uiso 1 1 calc R U . . .
C15 C 0.58205(10) 0.3056(2) 0.59538(8) 0.0266(3) Uani 1 1 d . . . . .
H15 H 0.5470 0.2037 0.6129 0.032 Uiso 1 1 calc R U . . .
C16 C 0.62556(9) 0.4758(2) 0.64600(7) 0.0231(3) Uani 1 1 d . . . . .
C17 C 0.67724(10) 0.6229(2) 0.62049(8) 0.0264(3) Uani 1 1 d . . . . .
H17 H 0.7074 0.7388 0.6546 0.032 Uiso 1 1 calc R U . . .
C18 C 0.68470(10) 0.5994(2) 0.54415(8) 0.0257(3) Uani 1 1 d . . . . .
H18 H 0.7204 0.7003 0.5269 0.031 Uiso 1 1 calc R U . . .
C19 C 0.65452(12) 0.6558(2) 0.77242(9) 0.0354(3) Uani 1 1 d . . . . .
H19A H 0.6385 0.6444 0.8215 0.053 Uiso 1 1 calc R U . . .
H19B H 0.6276 0.7868 0.7437 0.053 Uiso 1 1 calc R U . . .
H19C H 0.7264 0.6546 0.7886 0.053 Uiso 1 1 calc R U . . .


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

# 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 C11 1.3718(14) . ?
O1 C1 1.4253(14) . ?
O2 C5 1.2176(15) . ?
O3 C16 1.3723(15) . ?
O3 C19 1.4247(16) . ?
N1 C12 1.1370(17) . ?
C1 C12 1.4766(16) . ?
C1 C4 1.5514(15) . ?
C1 C2 1.5599(16) . ?
C2 C13 1.5016(16) . ?
C2 C3 1.5484(16) . ?
C2 H2 1.0000 . ?
C3 C4 1.5479(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5085(16) . ?
C4 H4 1.0000 . ?
C5 C6 1.4661(17) . ?
C6 C11 1.3957(16) . ?
C6 C7 1.4030(17) . ?
C7 C8 1.378(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3836(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3932(17) . ?
C10 H10 0.9500 . ?
C13 C18 1.3865(17) . ?
C13 C14 1.3963(17) . ?
C14 C15 1.3811(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3968(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3845(18) . ?
C17 C18 1.3959(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C11 O1 C1 118.26(9) . . ?
C16 O3 C19 117.68(11) . . ?
O1 C1 C12 104.43(9) . . ?
O1 C1 C4 120.92(9) . . ?
C12 C1 C4 112.22(10) . . ?
O1 C1 C2 117.37(9) . . ?
C12 C1 C2 113.14(9) . . ?
C4 C1 C2 88.71(8) . . ?
C13 C2 C3 121.21(10) . . ?
C13 C2 C1 120.05(10) . . ?
C3 C2 C1 87.92(8) . . ?
C13 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C4 C3 C2 89.25(8) . . ?
C4 C3 H3A 113.8 . . ?
C2 C3 H3A 113.8 . . ?
C4 C3 H3B 113.8 . . ?
C2 C3 H3B 113.8 . . ?
H3A C3 H3B 111.0 . . ?
C5 C4 C3 113.77(10) . . ?
C5 C4 C1 113.03(9) . . ?
C3 C4 C1 88.25(8) . . ?
C5 C4 H4 113.2 . . ?
C3 C4 H4 113.2 . . ?
C1 C4 H4 113.2 . . ?
O2 C5 C6 122.07(11) . . ?
O2 C5 C4 119.70(11) . . ?
C6 C5 C4 118.18(10) . . ?
C11 C6 C7 118.66(11) . . ?
C11 C6 C5 121.44(10) . . ?
C7 C6 C5 119.75(11) . . ?
C8 C7 C6 120.70(12) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.71(12) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.78(12) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.18(12) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
O1 C11 C10 115.09(10) . . ?
O1 C11 C6 123.98(10) . . ?
C10 C11 C6 120.91(11) . . ?
N1 C12 C1 179.25(14) . . ?
C18 C13 C14 118.01(11) . . ?
C18 C13 C2 121.61(11) . . ?
C14 C13 C2 120.36(10) . . ?
C15 C14 C13 121.15(11) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.07(12) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
O3 C16 C17 124.62(11) . . ?
O3 C16 C15 115.66(11) . . ?
C17 C16 C15 119.71(11) . . ?
C16 C17 C18 119.40(11) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C17 121.66(11) . . ?
C13 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C11 O1 C1 C12 -148.04(10) . . . . ?
C11 O1 C1 C4 -20.50(15) . . . . ?
C11 O1 C1 C2 85.79(12) . . . . ?
O1 C1 C2 C13 92.00(12) . . . . ?
C12 C1 C2 C13 -29.77(14) . . . . ?
C4 C1 C2 C13 -143.46(10) . . . . ?
O1 C1 C2 C3 -142.69(10) . . . . ?
C12 C1 C2 C3 95.55(10) . . . . ?
C4 C1 C2 C3 -18.14(8) . . . . ?
C13 C2 C3 C4 142.50(11) . . . . ?
C1 C2 C3 C4 18.18(8) . . . . ?
C2 C3 C4 C5 96.20(10) . . . . ?
C2 C3 C4 C1 -18.28(8) . . . . ?
O1 C1 C4 C5 24.48(14) . . . . ?
C12 C1 C4 C5 148.43(10) . . . . ?
C2 C1 C4 C5 -97.02(10) . . . . ?
O1 C1 C4 C3 139.64(10) . . . . ?
C12 C1 C4 C3 -96.40(10) . . . . ?
C2 C1 C4 C3 18.14(8) . . . . ?
C3 C4 C5 O2 69.91(15) . . . . ?
C1 C4 C5 O2 168.59(11) . . . . ?
C3 C4 C5 C6 -112.59(12) . . . . ?
C1 C4 C5 C6 -13.91(15) . . . . ?
O2 C5 C6 C11 177.77(12) . . . . ?
C4 C5 C6 C11 0.34(17) . . . . ?
O2 C5 C6 C7 2.18(19) . . . . ?
C4 C5 C6 C7 -175.25(11) . . . . ?
C11 C6 C7 C8 -1.81(19) . . . . ?
C5 C6 C7 C8 173.89(12) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C8 C9 C10 C11 -1.1(2) . . . . ?
C1 O1 C11 C10 -176.41(10) . . . . ?
C1 O1 C11 C6 5.04(16) . . . . ?
C9 C10 C11 O1 -179.56(11) . . . . ?
C9 C10 C11 C6 -0.96(18) . . . . ?
C7 C6 C11 O1 -179.13(11) . . . . ?
C5 C6 C11 O1 5.24(18) . . . . ?
C7 C6 C11 C10 2.39(18) . . . . ?
C5 C6 C11 C10 -173.24(11) . . . . ?
C3 C2 C13 C18 13.88(17) . . . . ?
C1 C2 C13 C18 121.43(13) . . . . ?
C3 C2 C13 C14 -167.68(11) . . . . ?
C1 C2 C13 C14 -60.13(15) . . . . ?
C18 C13 C14 C15 0.24(19) . . . . ?
C2 C13 C14 C15 -178.26(11) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C19 O3 C16 C17 0.34(19) . . . . ?
C19 O3 C16 C15 -179.29(12) . . . . ?
C14 C15 C16 O3 179.07(12) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
O3 C16 C17 C18 -179.30(12) . . . . ?
C15 C16 C17 C18 0.32(19) . . . . ?
C14 C13 C18 C17 -0.51(19) . . . . ?
C2 C13 C18 C17 177.97(12) . . . . ?
C16 C17 C18 C13 0.2(2) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_is_rd242jf1
_database_code_depnum_ccdc_archive 'CCDC 2250464'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 Cl N O2'
_chemical_formula_weight         323.76

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'

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

# CRYSTAL DATA

_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                   9.4965(12)
_cell_length_b                   10.7884(13)
_cell_length_c                   15.316(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.883(5)
_cell_angle_gamma                90
_cell_volume                     1516.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      32.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.261
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS-2016/2; Sheldrick, 2015)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            49983
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         31.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5266
_reflns_number_gt                4501
_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       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.6507P] 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         5266
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# 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 0.77597(3) 0.20731(4) 0.45112(2) 0.03279(10) Uani 1 1 d . . . . .
O1 O 0.08601(8) 0.34753(7) 0.58700(5) 0.01831(15) Uani 1 1 d . . . . .
O2 O 0.02099(11) 0.11389(8) 0.78542(6) 0.02678(19) Uani 1 1 d . . . . .
N1 N 0.12602(11) 0.14764(11) 0.42894(7) 0.0259(2) Uani 1 1 d . . . . .
C1 C 0.14932(11) 0.22738(9) 0.59363(7) 0.01439(17) Uani 1 1 d . . . . .
C2 C 0.31045(11) 0.21434(9) 0.65340(7) 0.01372(17) Uani 1 1 d . . . . .
C3 C 0.26438(12) 0.09037(10) 0.68971(8) 0.0190(2) Uani 1 1 d . . . . .
H3A H 0.2943 0.0159 0.6612 0.023 Uiso 1 1 calc R U . . .
H3B H 0.2941 0.0835 0.7564 0.023 Uiso 1 1 calc R U . . .
C4 C 0.10208(11) 0.12532(9) 0.65147(7) 0.01657(18) Uani 1 1 d . . . . .
H4 H 0.0460 0.0576 0.6132 0.020 Uiso 1 1 calc R U . . .
C5 C 0.02389(12) 0.17396(10) 0.71869(7) 0.01826(19) Uani 1 1 d . . . . .
C6 C -0.05255(11) 0.29244(10) 0.69563(7) 0.01736(19) Uani 1 1 d . . . . .
C7 C -0.16282(13) 0.32673(12) 0.73704(8) 0.0227(2) Uani 1 1 d . . . . .
H7 H -0.1850 0.2742 0.7815 0.027 Uiso 1 1 calc R U . . .
C8 C -0.23906(13) 0.43568(13) 0.71396(8) 0.0267(2) Uani 1 1 d . . . . .
H8 H -0.3154 0.4572 0.7408 0.032 Uiso 1 1 calc R U . . .
C9 C -0.20258(14) 0.51397(12) 0.65056(8) 0.0268(2) Uani 1 1 d . . . . .
H9 H -0.2537 0.5899 0.6353 0.032 Uiso 1 1 calc R U . . .
C10 C -0.09351(13) 0.48307(11) 0.60962(8) 0.0217(2) Uani 1 1 d . . . . .
H10 H -0.0687 0.5378 0.5673 0.026 Uiso 1 1 calc R U . . .
C11 C -0.02039(11) 0.37089(10) 0.63107(7) 0.01645(18) Uani 1 1 d . . . . .
C12 C 0.13499(11) 0.18422(10) 0.50031(7) 0.01782(19) Uani 1 1 d . . . . .
C13 C 0.34375(12) 0.31358(10) 0.72677(7) 0.0195(2) Uani 1 1 d . . . . .
H13A H 0.3568 0.3937 0.6998 0.029 Uiso 1 1 calc R U . . .
H13B H 0.4332 0.2917 0.7724 0.029 Uiso 1 1 calc R U . . .
H13C H 0.2627 0.3191 0.7553 0.029 Uiso 1 1 calc R U . . .
C14 C 0.42743(11) 0.21125(9) 0.60309(7) 0.01499(18) Uani 1 1 d . . . . .
C15 C 0.44080(12) 0.30971(10) 0.54682(7) 0.0189(2) Uani 1 1 d . . . . .
H15 H 0.3764 0.3783 0.5412 0.023 Uiso 1 1 calc R U . . .
C16 C 0.54647(13) 0.30938(12) 0.49886(8) 0.0225(2) Uani 1 1 d . . . . .
H16 H 0.5537 0.3759 0.4596 0.027 Uiso 1 1 calc R U . . .
C17 C 0.64130(12) 0.20940(12) 0.50968(8) 0.0226(2) Uani 1 1 d . . . . .
C18 C 0.63263(12) 0.11122(12) 0.56586(8) 0.0246(2) Uani 1 1 d . . . . .
H18 H 0.6994 0.0441 0.5729 0.030 Uiso 1 1 calc R U . . .
C19 C 0.52405(12) 0.11249(11) 0.61205(8) 0.0209(2) Uani 1 1 d . . . . .
H19 H 0.5159 0.0449 0.6502 0.025 Uiso 1 1 calc R U . . .


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

# 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 C17 1.7407(11) . ?
O1 C11 1.3749(12) . ?
O1 C1 1.4215(12) . ?
O2 C5 1.2164(14) . ?
N1 C12 1.1446(15) . ?
C1 C12 1.4759(15) . ?
C1 C4 1.5499(14) . ?
C1 C2 1.5747(14) . ?
C2 C14 1.5062(14) . ?
C2 C13 1.5253(14) . ?
C2 C3 1.5539(14) . ?
C3 C4 1.5482(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5097(15) . ?
C4 H4 1.0000 . ?
C5 C6 1.4676(15) . ?
C6 C11 1.3937(15) . ?
C6 C7 1.4060(15) . ?
C7 C8 1.3781(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3822(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3920(15) . ?
C10 H10 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.3898(14) . ?
C14 C15 1.3940(15) . ?
C15 C16 1.3875(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3875(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3804(19) . ?
C18 C19 1.3923(16) . ?
C18 H18 0.9500 . ?
C19 H19 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
C11 O1 C1 118.87(8) . . ?
O1 C1 C12 106.64(8) . . ?
O1 C1 C4 120.62(8) . . ?
C12 C1 C4 111.17(9) . . ?
O1 C1 C2 116.94(8) . . ?
C12 C1 C2 111.65(8) . . ?
C4 C1 C2 89.14(7) . . ?
C14 C2 C13 110.60(8) . . ?
C14 C2 C3 118.46(8) . . ?
C13 C2 C3 111.38(9) . . ?
C14 C2 C1 116.03(8) . . ?
C13 C2 C1 110.62(8) . . ?
C3 C2 C1 87.94(7) . . ?
C4 C3 C2 89.96(7) . . ?
C4 C3 H3A 113.6 . . ?
C2 C3 H3A 113.6 . . ?
C4 C3 H3B 113.6 . . ?
C2 C3 H3B 113.6 . . ?
H3A C3 H3B 110.9 . . ?
C5 C4 C3 116.28(9) . . ?
C5 C4 C1 114.09(8) . . ?
C3 C4 C1 89.03(7) . . ?
C5 C4 H4 111.9 . . ?
C3 C4 H4 111.9 . . ?
C1 C4 H4 111.9 . . ?
O2 C5 C6 123.34(10) . . ?
O2 C5 C4 120.61(10) . . ?
C6 C5 C4 115.98(9) . . ?
C11 C6 C7 118.98(10) . . ?
C11 C6 C5 120.98(9) . . ?
C7 C6 C5 120.02(10) . . ?
C8 C7 C6 120.78(11) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.11(11) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 121.22(11) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 119.28(11) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
O1 C11 C10 115.37(10) . . ?
O1 C11 C6 124.02(9) . . ?
C10 C11 C6 120.56(10) . . ?
N1 C12 C1 177.98(12) . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.85(10) . . ?
C19 C14 C2 121.43(9) . . ?
C15 C14 C2 119.72(9) . . ?
C16 C15 C14 121.23(10) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 118.30(11) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C18 C17 C16 122.02(10) . . ?
C18 C17 Cl1 118.72(9) . . ?
C16 C17 Cl1 119.26(10) . . ?
C17 C18 C19 118.67(10) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C14 C19 C18 120.91(11) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?

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
C11 O1 C1 C12 126.44(9) . . . . ?
C11 O1 C1 C4 -1.51(14) . . . . ?
C11 O1 C1 C2 -107.84(10) . . . . ?
O1 C1 C2 C14 -99.98(10) . . . . ?
C12 C1 C2 C14 23.21(12) . . . . ?
C4 C1 C2 C14 135.70(8) . . . . ?
O1 C1 C2 C13 27.04(12) . . . . ?
C12 C1 C2 C13 150.23(9) . . . . ?
C4 C1 C2 C13 -97.28(9) . . . . ?
O1 C1 C2 C3 139.15(9) . . . . ?
C12 C1 C2 C3 -97.67(9) . . . . ?
C4 C1 C2 C3 14.83(7) . . . . ?
C14 C2 C3 C4 -133.53(9) . . . . ?
C13 C2 C3 C4 96.53(9) . . . . ?
C1 C2 C3 C4 -14.84(7) . . . . ?
C2 C3 C4 C5 -101.47(9) . . . . ?
C2 C3 C4 C1 15.08(8) . . . . ?
O1 C1 C4 C5 -17.52(13) . . . . ?
C12 C1 C4 C5 -143.40(9) . . . . ?
C2 C1 C4 C5 103.65(9) . . . . ?
O1 C1 C4 C3 -136.05(9) . . . . ?
C12 C1 C4 C3 98.07(9) . . . . ?
C2 C1 C4 C3 -14.88(7) . . . . ?
C3 C4 C5 O2 -55.43(14) . . . . ?
C1 C4 C5 O2 -156.98(10) . . . . ?
C3 C4 C5 C6 127.62(10) . . . . ?
C1 C4 C5 C6 26.07(13) . . . . ?
O2 C5 C6 C11 165.38(11) . . . . ?
C4 C5 C6 C11 -17.76(14) . . . . ?
O2 C5 C6 C7 -16.37(17) . . . . ?
C4 C5 C6 C7 160.48(10) . . . . ?
C11 C6 C7 C8 0.47(17) . . . . ?
C5 C6 C7 C8 -177.81(11) . . . . ?
C6 C7 C8 C9 -1.87(18) . . . . ?
C7 C8 C9 C10 1.13(19) . . . . ?
C8 C9 C10 C11 1.01(18) . . . . ?
C1 O1 C11 C10 -169.90(9) . . . . ?
C1 O1 C11 C6 12.42(15) . . . . ?
C9 C10 C11 O1 179.79(10) . . . . ?
C9 C10 C11 C6 -2.44(17) . . . . ?
C7 C6 C11 O1 179.28(10) . . . . ?
C5 C6 C11 O1 -2.46(16) . . . . ?
C7 C6 C11 C10 1.71(16) . . . . ?
C5 C6 C11 C10 179.97(10) . . . . ?
C13 C2 C14 C19 110.16(11) . . . . ?
C3 C2 C14 C19 -20.14(14) . . . . ?
C1 C2 C14 C19 -122.81(10) . . . . ?
C13 C2 C14 C15 -69.23(12) . . . . ?
C3 C2 C14 C15 160.47(10) . . . . ?
C1 C2 C14 C15 57.81(12) . . . . ?
C19 C14 C15 C16 1.18(16) . . . . ?
C2 C14 C15 C16 -179.42(10) . . . . ?
C14 C15 C16 C17 -1.36(17) . . . . ?
C15 C16 C17 C18 0.38(17) . . . . ?
C15 C16 C17 Cl1 -179.41(9) . . . . ?
C16 C17 C18 C19 0.77(18) . . . . ?
Cl1 C17 C18 C19 -179.44(9) . . . . ?
C15 C14 C19 C18 0.01(16) . . . . ?
C2 C14 C19 C18 -179.39(10) . . . . ?
C17 C18 C19 C14 -0.96(17) . . . . ?

_refine_diff_density_max         0.588
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_av_rd242lf1b
_database_code_depnum_ccdc_archive 'CCDC 2250465'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N2 O2'
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24

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'

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

# CRYSTAL DATA

_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                   10.2547(13)
_cell_length_b                   6.2786(8)
_cell_length_c                   18.091(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.081(5)
_cell_angle_gamma                90
_cell_volume                     1146.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8331
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6854
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   '(SADABS-2016/2; Sheldrick, 2015)'

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

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            35365
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3037
_reflns_number_gt                2544
_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       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

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

# REFINEMENT DATA 

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.4118P] 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         3037
_refine_ls_number_parameters     225
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# 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
O1A O 0.6091(2) 0.6566(3) 0.38808(12) 0.0264(4) Uani 0.782(2) 1 d D U P A 1
C1A C 0.71386(13) 0.5097(2) 0.40804(8) 0.0237(3) Uani 0.782(2) 1 d D . P A 1
C12A C 0.82580(15) 0.6343(3) 0.44914(11) 0.0265(3) Uani 0.782(2) 1 d D . P A 1
N1A N 0.9053(5) 0.7347(8) 0.4860(3) 0.0532(14) Uani 0.782(2) 1 d D . P A 1
C2A C 0.68338(13) 0.3057(2) 0.45404(8) 0.0251(3) Uani 0.782(2) 1 d D . P A 1
C13A C 0.53947(18) 0.2716(3) 0.44363(10) 0.0269(4) Uani 0.782(2) 1 d D . P A 1
N2A N 0.4282(3) 0.2455(7) 0.4370(2) 0.0399(7) Uani 0.782(2) 1 d D . P A 1
C14A C 0.74467(19) 0.2904(3) 0.53682(11) 0.0317(4) Uani 0.782(2) 1 d D . P A 1
H14A H 0.7281 0.1485 0.5557 0.048 Uiso 0.782(2) 1 calc R U P A 1
H14B H 0.7050 0.3984 0.5652 0.048 Uiso 0.782(2) 1 calc R U P A 1
H14C H 0.8404 0.3146 0.5429 0.048 Uiso 0.782(2) 1 calc R U P A 1
C3A C 0.74979(16) 0.1676(2) 0.39923(9) 0.0316(4) Uani 0.782(2) 1 d D . P A 1
H3A H 0.8384 0.1132 0.4219 0.038 Uiso 0.782(2) 1 calc R U P A 1
H3B H 0.6927 0.0507 0.3753 0.038 Uiso 0.782(2) 1 calc R U P A 1
C4A C 0.75474(14) 0.3614(2) 0.34735(8) 0.0251(3) Uani 0.782(2) 1 d D . P A 1
H4A H 0.8462 0.3915 0.3380 0.030 Uiso 0.782(2) 1 calc R U P A 1
C5A C 0.6526(3) 0.3442(6) 0.27410(15) 0.0385(8) Uani 0.782(2) 1 d D . P A 1
O2A O 0.6746(4) 0.2216(6) 0.22655(18) 0.0585(10) Uani 0.782(2) 1 d D . P A 1
C6A C 0.5479(2) 0.5063(4) 0.26197(16) 0.0275(6) Uani 0.782(2) 1 d D . P A 1
C7A C 0.4660(3) 0.5229(5) 0.19159(17) 0.0350(7) Uani 0.782(2) 1 d D . P A 1
H7A H 0.4756 0.4243 0.1531 0.042 Uiso 0.782(2) 1 calc R U P A 1
C8A C 0.3722(4) 0.6801(8) 0.1778(2) 0.0464(11) Uani 0.782(2) 1 d D . P A 1
H8A H 0.3174 0.6907 0.1298 0.056 Uiso 0.782(2) 1 calc R U P A 1
C9A C 0.3575(3) 0.8245(6) 0.2344(2) 0.0402(10) Uani 0.782(2) 1 d D . P A 1
H9A H 0.2930 0.9341 0.2244 0.048 Uiso 0.782(2) 1 calc R U P A 1
C10A C 0.4356(4) 0.8104(6) 0.30465(18) 0.0285(7) Uani 0.782(2) 1 d D . P A 1
H10A H 0.4244 0.9076 0.3433 0.034 Uiso 0.782(2) 1 calc R U P A 1
C11A C 0.5309(3) 0.6508(5) 0.31764(14) 0.0236(6) Uani 0.782(2) 1 d D . P A 1
O1B O 0.5964(11) 0.6260(11) 0.3807(5) 0.0293(18) Uiso 0.218(2) 1 d D U P A 2
C1B C 0.6264(4) 0.4115(7) 0.4028(2) 0.0203(10) Uiso 0.218(2) 1 d D U P A 2
C12B C 0.5118(6) 0.3276(10) 0.4333(4) 0.0199(14) Uiso 0.218(2) 1 d D U P A 2
N1B N 0.4250(14) 0.241(3) 0.4522(9) 0.037(3) Uiso 0.218(2) 1 d D U P A 2
C2B C 0.7658(4) 0.3935(7) 0.4536(2) 0.0224(10) Uiso 0.218(2) 1 d D U P A 2
C13B C 0.8291(6) 0.6002(9) 0.4768(4) 0.0222(14) Uiso 0.218(2) 1 d D U P A 2
N2B N 0.9139(12) 0.725(2) 0.4808(8) 0.0179(18) Uiso 0.218(2) 1 d D U P A 2
C14B C 0.7684(9) 0.2422(12) 0.5198(4) 0.035(2) Uiso 0.218(2) 1 d D U P A 2
H14D H 0.7256 0.1077 0.5020 0.053 Uiso 0.218(2) 1 calc R U P A 2
H14E H 0.8604 0.2148 0.5433 0.053 Uiso 0.218(2) 1 calc R U P A 2
H14F H 0.7209 0.3069 0.5566 0.053 Uiso 0.218(2) 1 calc R U P A 2
C3B C 0.8189(5) 0.2912(8) 0.3855(3) 0.0241(11) Uiso 0.218(2) 1 d D U P A 2
H3C H 0.8716 0.3903 0.3600 0.029 Uiso 0.218(2) 1 calc R U P A 2
H3D H 0.8667 0.1553 0.3978 0.029 Uiso 0.218(2) 1 calc R U P A 2
C4B C 0.6749(4) 0.2627(7) 0.3444(2) 0.0230(11) Uiso 0.218(2) 1 d D U P A 2
H4B H 0.6411 0.1133 0.3444 0.028 Uiso 0.218(2) 1 calc R U P A 2
C5B C 0.6589(9) 0.3655(15) 0.2656(4) 0.020(2) Uiso 0.218(2) 1 d D U P A 2
O2B O 0.6785(14) 0.2490(17) 0.2152(6) 0.0314(17) Uiso 0.218(2) 1 d D U P A 2
C6B C 0.5489(8) 0.5216(13) 0.2510(5) 0.025(2) Uiso 0.218(2) 1 d DG U P A 2
C7B C 0.4676(10) 0.5383(15) 0.1812(5) 0.027(2) Uiso 0.218(2) 1 d DG U P A 2
H7B H 0.4816 0.4480 0.1412 0.033 Uiso 0.218(2) 1 calc R U P A 2
C8B C 0.3657(10) 0.6873(18) 0.1700(5) 0.022(2) Uiso 0.218(2) 1 d DG U P A 2
H8B H 0.3101 0.6987 0.1223 0.027 Uiso 0.218(2) 1 calc R U P A 2
C9B C 0.3452(10) 0.8195(17) 0.2285(6) 0.026(3) Uiso 0.218(2) 1 d DG U P A 2
H9B H 0.2756 0.9213 0.2208 0.031 Uiso 0.218(2) 1 calc R U P A 2
C10B C 0.4266(14) 0.803(2) 0.2983(5) 0.029(2) Uiso 0.218(2) 1 d DG U P A 2
H10B H 0.4126 0.8932 0.3383 0.035 Uiso 0.218(2) 1 calc R U P A 2
C11B C 0.5284(13) 0.654(2) 0.3095(4) 0.029(2) Uiso 0.218(2) 1 d DG U P A 2


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

# 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
O1A C11A 1.382(2) . ?
O1A C1A 1.414(2) . ?
C1A C12A 1.478(2) . ?
C1A C4A 1.552(2) . ?
C1A C2A 1.588(2) . ?
C12A N1A 1.147(5) . ?
C2A C13A 1.470(2) . ?
C2A C14A 1.522(2) . ?
C2A C3A 1.561(2) . ?
C13A N2A 1.138(3) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C3A C4A 1.543(2) . ?
C3A H3A 0.9900 . ?
C3A H3B 0.9900 . ?
C4A C5A 1.542(3) . ?
C4A H4A 1.0000 . ?
C5A O2A 1.204(3) . ?
C5A C6A 1.468(3) . ?
C6A C11A 1.389(2) . ?
C6A C7A 1.401(3) . ?
C7A C8A 1.370(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.396(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.381(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.391(2) . ?
C10A H10A 0.9500 . ?
O1B C11B 1.363(7) . ?
O1B C1B 1.423(7) . ?
C1B C12B 1.480(6) . ?
C1B C4B 1.556(5) . ?
C1B C2B 1.562(5) . ?
C12B N1B 1.146(9) . ?
C2B C13B 1.479(6) . ?
C2B C14B 1.526(7) . ?
C2B C3B 1.569(6) . ?
C13B N2B 1.164(9) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C3B C4B 1.544(6) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C4B C5B 1.547(7) . ?
C4B H4B 1.0000 . ?
C5B O2B 1.213(7) . ?
C5B C6B 1.483(6) . ?
C6B C7B 1.3900 . ?
C6B C11B 1.3900 . ?
C7B C8B 1.3900 . ?
C7B H7B 0.9500 . ?
C8B C9B 1.3900 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3900 . ?
C10B H10B 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
C11A O1A C1A 120.70(19) . . ?
O1A C1A C12A 105.76(15) . . ?
O1A C1A C4A 119.86(14) . . ?
C12A C1A C4A 113.04(12) . . ?
O1A C1A C2A 116.72(15) . . ?
C12A C1A C2A 111.72(13) . . ?
C4A C1A C2A 89.38(11) . . ?
N1A C12A C1A 173.6(3) . . ?
C13A C2A C14A 110.43(14) . . ?
C13A C2A C3A 112.17(13) . . ?
C14A C2A C3A 116.05(14) . . ?
C13A C2A C1A 109.62(13) . . ?
C14A C2A C1A 118.76(12) . . ?
C3A C2A C1A 88.14(11) . . ?
N2A C13A C2A 178.7(3) . . ?
C2A C14A H14A 109.5 . . ?
C2A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C2A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C4A C3A C2A 90.73(11) . . ?
C4A C3A H3A 113.5 . . ?
C2A C3A H3A 113.5 . . ?
C4A C3A H3B 113.5 . . ?
C2A C3A H3B 113.5 . . ?
H3A C3A H3B 110.8 . . ?
C5A C4A C3A 112.20(18) . . ?
C5A C4A C1A 115.02(14) . . ?
C3A C4A C1A 90.06(11) . . ?
C5A C4A H4A 112.6 . . ?
C3A C4A H4A 112.6 . . ?
C1A C4A H4A 112.6 . . ?
O2A C5A C6A 124.0(3) . . ?
O2A C5A C4A 118.3(3) . . ?
C6A C5A C4A 116.7(2) . . ?
C11A C6A C7A 118.60(15) . . ?
C11A C6A C5A 121.7(2) . . ?
C7A C6A C5A 119.6(2) . . ?
C8A C7A C6A 120.63(18) . . ?
C8A C7A H7A 119.7 . . ?
C6A C7A H7A 119.7 . . ?
C7A C8A C9A 119.8(2) . . ?
C7A C8A H8A 120.1 . . ?
C9A C8A H8A 120.1 . . ?
C10A C9A C8A 120.92(18) . . ?
C10A C9A H9A 119.5 . . ?
C8A C9A H9A 119.5 . . ?
C9A C10A C11A 118.59(17) . . ?
C9A C10A H10A 120.7 . . ?
C11A C10A H10A 120.7 . . ?
O1A C11A C6A 124.00(19) . . ?
O1A C11A C10A 114.5(2) . . ?
C6A C11A C10A 121.47(17) . . ?
C11B O1B C1B 115.9(7) . . ?
O1B C1B C12B 107.2(6) . . ?
O1B C1B C4B 117.1(5) . . ?
C12B C1B C4B 114.1(4) . . ?
O1B C1B C2B 111.4(5) . . ?
C12B C1B C2B 117.4(4) . . ?
C4B C1B C2B 89.3(3) . . ?
N1B C12B C1B 171.8(11) . . ?
C13B C2B C14B 112.1(5) . . ?
C13B C2B C1B 114.5(4) . . ?
C14B C2B C1B 113.3(5) . . ?
C13B C2B C3B 112.8(4) . . ?
C14B C2B C3B 113.6(4) . . ?
C1B C2B C3B 88.6(3) . . ?
N2B C13B C2B 153.5(9) . . ?
C2B C14B H14D 109.5 . . ?
C2B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C2B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C4B C3B C2B 89.5(3) . . ?
C4B C3B H3C 113.7 . . ?
C2B C3B H3C 113.7 . . ?
C4B C3B H3D 113.7 . . ?
C2B C3B H3D 113.7 . . ?
H3C C3B H3D 111.0 . . ?
C3B C4B C5B 109.5(5) . . ?
C3B C4B C1B 89.8(3) . . ?
C5B C4B C1B 112.4(5) . . ?
C3B C4B H4B 114.3 . . ?
C5B C4B H4B 114.3 . . ?
C1B C4B H4B 114.3 . . ?
O2B C5B C6B 119.1(8) . . ?
O2B C5B C4B 115.9(7) . . ?
C6B C5B C4B 113.2(5) . . ?
C7B C6B C11B 120.0 . . ?
C7B C6B C5B 121.9(5) . . ?
C11B C6B C5B 118.1(5) . . ?
C8B C7B C6B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C7B C8B C9B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
O1B C11B C10B 118.1(6) . . ?
O1B C11B C6B 121.5(6) . . ?
C10B C11B C6B 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
C11A O1A C1A C12A 137.9(3) . . . . ?
C11A O1A C1A C4A 8.7(4) . . . . ?
C11A O1A C1A C2A -97.2(3) . . . . ?
O1A C1A C2A C13A 20.31(19) . . . . ?
C12A C1A C2A C13A 142.17(14) . . . . ?
C4A C1A C2A C13A -103.19(13) . . . . ?
O1A C1A C2A C14A -107.88(19) . . . . ?
C12A C1A C2A C14A 14.0(2) . . . . ?
C4A C1A C2A C14A 128.62(15) . . . . ?
O1A C1A C2A C3A 133.22(15) . . . . ?
C12A C1A C2A C3A -104.92(13) . . . . ?
C4A C1A C2A C3A 9.72(10) . . . . ?
C13A C2A C3A C4A 100.67(15) . . . . ?
C14A C2A C3A C4A -131.11(13) . . . . ?
C1A C2A C3A C4A -9.78(10) . . . . ?
C2A C3A C4A C5A -107.20(16) . . . . ?
C2A C3A C4A C1A 10.00(11) . . . . ?
O1A C1A C4A C5A -16.0(3) . . . . ?
C12A C1A C4A C5A -141.7(2) . . . . ?
C2A C1A C4A C5A 104.85(19) . . . . ?
O1A C1A C4A C3A -130.64(17) . . . . ?
C12A C1A C4A C3A 103.60(15) . . . . ?
C2A C1A C4A C3A -9.83(10) . . . . ?
C3A C4A C5A O2A -74.4(3) . . . . ?
C1A C4A C5A O2A -175.5(3) . . . . ?
C3A C4A C5A C6A 116.3(2) . . . . ?
C1A C4A C5A C6A 15.3(3) . . . . ?
O2A C5A C6A C11A -176.8(3) . . . . ?
C4A C5A C6A C11A -8.2(4) . . . . ?
O2A C5A C6A C7A 0.5(4) . . . . ?
C4A C5A C6A C7A 169.0(3) . . . . ?
C11A C6A C7A C8A 0.8(3) . . . . ?
C5A C6A C7A C8A -176.6(2) . . . . ?
C6A C7A C8A C9A -0.3(4) . . . . ?
C7A C8A C9A C10A -0.6(3) . . . . ?
C8A C9A C10A C11A 1.0(3) . . . . ?
C1A O1A C11A C6A -0.4(4) . . . . ?
C1A O1A C11A C10A -177.3(2) . . . . ?
C7A C6A C11A O1A -177.0(4) . . . . ?
C5A C6A C11A O1A 0.2(4) . . . . ?
C7A C6A C11A C10A -0.4(3) . . . . ?
C5A C6A C11A C10A 176.9(2) . . . . ?
C9A C10A C11A O1A 176.5(3) . . . . ?
C9A C10A C11A C6A -0.5(2) . . . . ?
C11B O1B C1B C12B -87.4(11) . . . . ?
C11B O1B C1B C4B 42.3(12) . . . . ?
C11B O1B C1B C2B 143.0(9) . . . . ?
O1B C1B C2B C13B 8.1(7) . . . . ?
C12B C1B C2B C13B -115.9(5) . . . . ?
C4B C1B C2B C13B 127.1(4) . . . . ?
O1B C1B C2B C14B 138.4(6) . . . . ?
C12B C1B C2B C14B 14.4(6) . . . . ?
C4B C1B C2B C14B -102.6(5) . . . . ?
O1B C1B C2B C3B -106.4(6) . . . . ?
C12B C1B C2B C3B 129.6(5) . . . . ?
C4B C1B C2B C3B 12.6(3) . . . . ?
C14B C2B C13B N2B 108(2) . . . . ?
C1B C2B C13B N2B -122(2) . . . . ?
C3B C2B C13B N2B -22(2) . . . . ?
C13B C2B C3B C4B -128.8(4) . . . . ?
C14B C2B C3B C4B 102.2(5) . . . . ?
C1B C2B C3B C4B -12.7(3) . . . . ?
C2B C3B C4B C5B 126.5(5) . . . . ?
C2B C3B C4B C1B 12.8(3) . . . . ?
O1B C1B C4B C3B 101.0(6) . . . . ?
C12B C1B C4B C3B -132.7(4) . . . . ?
C2B C1B C4B C3B -12.8(3) . . . . ?
O1B C1B C4B C5B -10.1(8) . . . . ?
C12B C1B C4B C5B 116.3(6) . . . . ?
C2B C1B C4B C5B -123.9(5) . . . . ?
C3B C4B C5B O2B 91.1(9) . . . . ?
C1B C4B C5B O2B -170.8(8) . . . . ?
C3B C4B C5B C6B -126.2(5) . . . . ?
C1B C4B C5B C6B -28.1(7) . . . . ?
O2B C5B C6B C7B 0.0(3) . . . . ?
C4B C5B C6B C7B -141.4(8) . . . . ?
O2B C5B C6B C11B -179.9(3) . . . . ?
C4B C5B C6B C11B 38.7(9) . . . . ?
C11B C6B C7B C8B 0.0 . . . . ?
C5B C6B C7B C8B -179.9(2) . . . . ?
C6B C7B C8B C9B 0.0 . . . . ?
C7B C8B C9B C10B 0.0 . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C1B O1B C11B C10B 138.3(7) . . . . ?
C1B O1B C11B C6B -34.4(16) . . . . ?
C9B C10B C11B O1B -172.8(14) . . . . ?
C9B C10B C11B C6B 0.0 . . . . ?
C7B C6B C11B O1B 172.5(14) . . . . ?
C5B C6B C11B O1B -7.6(14) . . . . ?
C7B C6B C11B C10B 0.0 . . . . ?
C5B C6B C11B C10B 179.9(2) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040

