# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

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

data_b170112a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1539269'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 N3 O5'
_chemical_formula_weight         499.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.851(5)
_cell_length_b                   10.081(6)
_cell_length_c                   28.437(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.989(15)
_cell_angle_gamma                90
_cell_volume                     2536(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9834
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      24.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29701
_diffrn_reflns_av_unetI/netI     0.1205
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         27.640
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11225
_reflns_number_gt                6644
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+0.5000P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(13)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         11225
_refine_ls_number_parameters     680
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0115(3) 1.3091(3) 0.62535(10) 0.0424(8) Uani 1 1 d . . . . .
O2 O 0.8882(4) 1.0229(3) 0.51846(10) 0.0449(8) Uani 1 1 d . . . . .
O3 O 1.0864(3) 1.0642(3) 0.59932(10) 0.0345(7) Uani 1 1 d . . . . .
H3 H 1.0638 1.1414 0.6047 0.052 Uiso 1 1 calc R U . . .
O4 O 1.1375(4) 0.8116(3) 0.58925(10) 0.0466(9) Uani 1 1 d . . . . .
O5 O 1.1049(3) 0.7905(3) 0.66687(10) 0.0409(8) Uani 1 1 d . . . . .
N1 N 0.9478(4) 1.3734(3) 0.69893(12) 0.0318(9) Uani 1 1 d . . . . .
N2 N 0.7278(4) 1.0539(3) 0.60685(11) 0.0294(9) Uani 1 1 d . . . . .
N3 N 0.8349(4) 0.8050(4) 0.53336(11) 0.0354(9) Uani 1 1 d . . . . .
C1 C 0.9522(5) 1.2875(4) 0.66255(15) 0.0317(10) Uani 1 1 d . . . . .
C2 C 0.8660(4) 1.1585(4) 0.67631(13) 0.0242(10) Uani 1 1 d . . . . .
C3 C 0.8225(4) 1.1913(4) 0.72618(13) 0.0260(10) Uani 1 1 d . . . . .
C4 C 0.7472(4) 1.1175(4) 0.75870(14) 0.0284(10) Uani 1 1 d . . . . .
H4 H 0.7153 1.0317 0.7517 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7194(5) 1.1738(4) 0.80234(14) 0.0343(11) Uani 1 1 d . . . . .
H5 H 0.6673 1.1260 0.8246 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7695(5) 1.3009(5) 0.81257(15) 0.0412(12) Uani 1 1 d . . . . .
H6 H 0.7504 1.3372 0.8418 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8476(5) 1.3758(4) 0.78037(16) 0.0366(12) Uani 1 1 d . . . . .
H7 H 0.8816 1.4609 0.7876 0.044 Uiso 1 1 calc R U . . .
C8 C 0.8724(5) 1.3186(4) 0.73745(14) 0.0284(10) Uani 1 1 d . . . . .
C9 C 1.0167(5) 1.5052(4) 0.69779(17) 0.0444(13) Uani 1 1 d . . . . .
H9A H 1.1072 1.5059 0.7174 0.067 Uiso 1 1 calc R U . . .
H9B H 0.9469 1.5696 0.7092 0.067 Uiso 1 1 calc R U . . .
H9C H 1.0413 1.5266 0.6661 0.067 Uiso 1 1 calc R U . . .
C10 C 0.7286(5) 1.1409(4) 0.64429(13) 0.0249(10) Uani 1 1 d . . . . .
C11 C 0.5910(5) 1.2049(4) 0.64311(14) 0.0318(11) Uani 1 1 d . . . . .
H11 H 0.5615 1.2705 0.6639 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5024(5) 1.1540(5) 0.60499(15) 0.0393(12) Uani 1 1 d . . . . .
H12 H 0.4044 1.1791 0.5961 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5883(5) 1.0607(5) 0.58366(16) 0.0408(12) Uani 1 1 d . . . . .
H13 H 0.5578 1.0099 0.5577 0.049 Uiso 1 1 calc R U . . .
C14 C 0.8372(5) 0.9470(4) 0.59856(14) 0.0277(10) Uani 1 1 d . . . . .
C15 C 0.8594(5) 0.9333(5) 0.54539(15) 0.0323(11) Uani 1 1 d . . . . .
C16 C 0.7825(5) 0.7292(4) 0.57185(15) 0.0310(11) Uani 1 1 d . . . . .
C17 C 0.7383(5) 0.5971(4) 0.57359(17) 0.0394(12) Uani 1 1 d . . . . .
C18 C 0.6793(5) 0.5557(5) 0.61617(17) 0.0422(12) Uani 1 1 d . . . . .
H18 H 0.6488 0.4677 0.6185 0.051 Uiso 1 1 calc R U . . .
C19 C 0.6631(5) 0.6368(5) 0.65514(16) 0.0368(11) Uani 1 1 d . . . . .
C20 C 0.7153(5) 0.7670(4) 0.65237(14) 0.0314(11) Uani 1 1 d . . . . .
H20 H 0.7098 0.8233 0.6782 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7752(4) 0.8118(4) 0.61096(13) 0.0268(10) Uani 1 1 d . . . . .
C22 C 0.8482(6) 0.7609(5) 0.48463(15) 0.0593(16) Uani 1 1 d . . . . .
H22A H 0.7510 0.7328 0.4723 0.089 Uiso 1 1 calc R U . . .
H22B H 0.9180 0.6880 0.4836 0.089 Uiso 1 1 calc R U . . .
H22C H 0.8845 0.8327 0.4660 0.089 Uiso 1 1 calc R U . . .
C23 C 0.7475(7) 0.4981(5) 0.5337(2) 0.0659(17) Uani 1 1 d . . . . .
H23A H 0.6838 0.5268 0.5077 0.099 Uiso 1 1 calc R U . . .
H23B H 0.7146 0.4127 0.5442 0.099 Uiso 1 1 calc R U . . .
H23C H 0.8501 0.4921 0.5240 0.099 Uiso 1 1 calc R U . . .
C24 C 0.5912(6) 0.5846(5) 0.69928(17) 0.0532(14) Uani 1 1 d . . . . .
H24A H 0.4841 0.5762 0.6937 0.080 Uiso 1 1 calc R U . . .
H24B H 0.6109 0.6453 0.7248 0.080 Uiso 1 1 calc R U . . .
H24C H 0.6334 0.4994 0.7072 0.080 Uiso 1 1 calc R U . . .
C25 C 0.9675(4) 1.0331(4) 0.67468(13) 0.0258(10) Uani 1 1 d . . . . .
H25A H 1.0645 1.0537 0.6899 0.031 Uiso 1 1 calc R U . . .
H25B H 0.9213 0.9636 0.6929 0.031 Uiso 1 1 calc R U . . .
C26 C 0.9952(5) 0.9789(4) 0.62524(14) 0.0260(10) Uani 1 1 d . . . . .
C27 C 1.0854(5) 0.8489(4) 0.63045(17) 0.0330(11) Uani 1 1 d . . . . .
C28 C 1.2242(6) 0.6872(5) 0.58782(19) 0.0629(17) Uani 1 1 d . . . . .
H28A H 1.2729 0.6700 0.6183 0.076 Uiso 1 1 calc R U . . .
H28B H 1.1573 0.6137 0.5800 0.076 Uiso 1 1 calc R U . . .
C29 C 1.3385(6) 0.7013(6) 0.5519(2) 0.0720(18) Uani 1 1 d . . . . .
H29A H 1.2892 0.7179 0.5218 0.108 Uiso 1 1 calc R U . . .
H29B H 1.3966 0.6211 0.5503 0.108 Uiso 1 1 calc R U . . .
H29C H 1.4042 0.7741 0.5599 0.108 Uiso 1 1 calc R U . . .
O6 O 1.2745(3) 0.7393(3) 0.77393(11) 0.0420(8) Uani 1 1 d . . . . .
O7 O 1.0519(4) 0.5228(3) 0.90019(11) 0.0447(9) Uani 1 1 d . . . . .
O8 O 1.0176(3) 0.6506(3) 0.81160(10) 0.0337(7) Uani 1 1 d . . . . .
H8 H 1.1020 0.6693 0.8026 0.051 Uiso 1 1 calc R U . . .
O9 O 0.7283(3) 0.6468(3) 0.85271(9) 0.0322(7) Uani 1 1 d . . . . .
O10 O 0.7048(4) 0.8115(3) 0.80074(12) 0.0587(10) Uani 1 1 d . . . . .
N4 N 1.3218(4) 0.9537(4) 0.75063(13) 0.0373(10) Uani 1 1 d . . . . .
N5 N 1.1603(4) 0.8048(3) 0.89290(11) 0.0277(8) Uani 1 1 d . . . . .
N6 N 0.9046(4) 0.6391(4) 0.95076(12) 0.0323(9) Uani 1 1 d . . . . .
C30 C 1.2611(5) 0.8606(5) 0.77879(15) 0.0338(11) Uani 1 1 d . . . . .
C31 C 1.1700(5) 0.9311(4) 0.81685(14) 0.0265(10) Uani 1 1 d . . . . .
C32 C 1.1999(5) 1.0758(4) 0.80564(14) 0.0288(10) Uani 1 1 d . . . . .
C33 C 1.1593(5) 1.1900(4) 0.82830(16) 0.0368(12) Uani 1 1 d . . . . .
H33 H 1.0997 1.1857 0.8546 0.044 Uiso 1 1 calc R U . . .
C34 C 1.2079(5) 1.3125(5) 0.81174(17) 0.0439(12) Uani 1 1 d . . . . .
H34 H 1.1819 1.3902 0.8271 0.053 Uiso 1 1 calc R U . . .
C35 C 1.2952(5) 1.3178(5) 0.77220(19) 0.0513(14) Uani 1 1 d . . . . .
H35 H 1.3258 1.3999 0.7610 0.062 Uiso 1 1 calc R U . . .
C36 C 1.3380(5) 1.2034(5) 0.74900(17) 0.0469(13) Uani 1 1 d . . . . .
H36 H 1.3971 1.2072 0.7226 0.056 Uiso 1 1 calc R U . . .
C37 C 1.2891(5) 1.0831(5) 0.76669(15) 0.0343(11) Uani 1 1 d . . . . .
C38 C 1.4082(6) 0.9234(6) 0.70913(18) 0.0589(16) Uani 1 1 d . . . . .
H38A H 1.5123 0.9464 0.7151 0.088 Uiso 1 1 calc R U . . .
H38B H 1.3685 0.9734 0.6828 0.088 Uiso 1 1 calc R U . . .
H38C H 1.4005 0.8303 0.7023 0.088 Uiso 1 1 calc R U . . .
C39 C 1.2321(5) 0.8948(4) 0.86508(14) 0.0276(10) Uani 1 1 d . . . . .
C40 C 1.3658(5) 0.9304(5) 0.88768(16) 0.0391(12) Uani 1 1 d . . . . .
H40 H 1.4373 0.9891 0.8765 0.047 Uiso 1 1 calc R U . . .
C41 C 1.3747(5) 0.8619(5) 0.93086(16) 0.0388(12) Uani 1 1 d . . . . .
H41 H 1.4532 0.8670 0.9534 0.047 Uiso 1 1 calc R U . . .
C42 C 1.2471(5) 0.7867(5) 0.93354(14) 0.0360(11) Uani 1 1 d . . . . .
H42 H 1.2229 0.7324 0.9586 0.043 Uiso 1 1 calc R U . . .
C43 C 1.0011(4) 0.7626(4) 0.88793(13) 0.0246(10) Uani 1 1 d . . . . .
C44 C 0.9898(5) 0.6246(4) 0.91156(14) 0.0306(11) Uani 1 1 d . . . . .
C45 C 0.8511(4) 0.7708(4) 0.95578(14) 0.0290(10) Uani 1 1 d . . . . .
C46 C 0.7683(5) 0.8258(5) 0.99209(14) 0.0350(11) Uani 1 1 d . . . . .
C47 C 0.7294(5) 0.9595(5) 0.98612(15) 0.0348(11) Uani 1 1 d . . . . .
H47 H 0.6721 0.9991 1.0091 0.042 Uiso 1 1 calc R U . . .
C48 C 0.7700(5) 1.0363(4) 0.94860(15) 0.0327(11) Uani 1 1 d . . . . .
C49 C 0.8609(5) 0.9793(4) 0.91477(14) 0.0280(10) Uani 1 1 d . . . . .
H49 H 0.8944 1.0300 0.8899 0.034 Uiso 1 1 calc R U . . .
C50 C 0.9004(5) 0.8471(4) 0.91864(14) 0.0248(10) Uani 1 1 d . . . . .
C51 C 0.8694(5) 0.5232(5) 0.97940(17) 0.0450(13) Uani 1 1 d . . . . .
H51A H 0.9186 0.4464 0.9671 0.068 Uiso 1 1 calc R U . . .
H51B H 0.7620 0.5091 0.9785 0.068 Uiso 1 1 calc R U . . .
H51C H 0.9043 0.5380 1.0113 0.068 Uiso 1 1 calc R U . . .
C52 C 0.7261(6) 0.7546(5) 1.03644(17) 0.0640(16) Uani 1 1 d . . . . .
H52A H 0.6511 0.6884 1.0289 0.096 Uiso 1 1 calc R U . . .
H52B H 0.6861 0.8172 1.0582 0.096 Uiso 1 1 calc R U . . .
H52C H 0.8142 0.7128 1.0504 0.096 Uiso 1 1 calc R U . . .
C53 C 0.7169(6) 1.1784(4) 0.94255(17) 0.0501(14) Uani 1 1 d . . . . .
H53A H 0.6630 1.2050 0.9697 0.075 Uiso 1 1 calc R U . . .
H53B H 0.6512 1.1849 0.9151 0.075 Uiso 1 1 calc R U . . .
H53C H 0.8027 1.2353 0.9390 0.075 Uiso 1 1 calc R U . . .
C54 C 1.0005(5) 0.8928(4) 0.81084(14) 0.0248(10) Uani 1 1 d . . . . .
H54A H 0.9404 0.9639 0.8235 0.030 Uiso 1 1 calc R U . . .
H54B H 0.9750 0.8866 0.7775 0.030 Uiso 1 1 calc R U . . .
C55 C 0.9551(4) 0.7625(4) 0.83431(13) 0.0264(10) Uani 1 1 d . . . . .
C56 C 0.7817(5) 0.7455(4) 0.82726(15) 0.0326(11) Uani 1 1 d . . . . .
C57 C 0.5642(5) 0.6205(5) 0.84736(16) 0.0424(13) Uani 1 1 d . . . . .
H57A H 0.5422 0.5736 0.8181 0.051 Uiso 1 1 calc R U . . .
H57B H 0.5087 0.7035 0.8466 0.051 Uiso 1 1 calc R U . . .
C58 C 0.5179(5) 0.5384(5) 0.88819(18) 0.0513(14) Uani 1 1 d . . . . .
H58A H 0.5725 0.4561 0.8885 0.077 Uiso 1 1 calc R U . . .
H58B H 0.4114 0.5207 0.8854 0.077 Uiso 1 1 calc R U . . .
H58C H 0.5400 0.5856 0.9169 0.077 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.217(5) . ?
O2 C15 1.217(5) . ?
O3 C26 1.405(4) . ?
O3 H3 0.8200 . ?
O4 C27 1.328(5) . ?
O4 C28 1.471(5) . ?
O5 C27 1.199(5) . ?
N1 C1 1.351(5) . ?
N1 C8 1.415(5) . ?
N1 C9 1.463(5) . ?
N2 C10 1.379(5) . ?
N2 C13 1.381(5) . ?
N2 C14 1.473(5) . ?
N3 C15 1.354(6) . ?
N3 C16 1.426(5) . ?
N3 C22 1.464(5) . ?
C1 C2 1.564(6) . ?
C2 C10 1.504(6) . ?
C2 C3 1.519(5) . ?
C2 C25 1.553(5) . ?
C3 C4 1.376(5) . ?
C3 C8 1.392(6) . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(6) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.378(6) . ?
C11 C12 1.413(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C21 1.516(6) . ?
C14 C15 1.538(6) . ?
C14 C26 1.601(6) . ?
C16 C17 1.389(6) . ?
C16 C21 1.393(5) . ?
C17 C18 1.399(6) . ?
C17 C23 1.515(6) . ?
C18 C19 1.388(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(6) . ?
C19 C24 1.521(6) . ?
C20 C21 1.384(5) . ?
C20 H20 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.536(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.539(6) . ?
C28 C29 1.470(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
O6 C30 1.236(5) . ?
O7 C44 1.213(5) . ?
O8 C55 1.422(5) . ?
O8 H8 0.8200 . ?
O9 C56 1.327(5) . ?
O9 C57 1.478(5) . ?
O10 C56 1.200(5) . ?
N4 C30 1.357(6) . ?
N4 C37 1.416(6) . ?
N4 C38 1.460(5) . ?
N5 C39 1.374(5) . ?
N5 C42 1.378(5) . ?
N5 C43 1.474(5) . ?
N6 C44 1.375(5) . ?
N6 C45 1.418(6) . ?
N6 C51 1.465(5) . ?
C30 C31 1.545(6) . ?
C31 C39 1.505(6) . ?
C31 C32 1.518(6) . ?
C31 C54 1.553(6) . ?
C32 C33 1.373(6) . ?
C32 C37 1.384(6) . ?
C33 C34 1.395(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.388(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.388(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.388(6) . ?
C36 H36 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.374(6) . ?
C40 C41 1.409(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.364(6) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C50 1.529(5) . ?
C43 C44 1.550(6) . ?
C43 C55 1.565(5) . ?
C45 C50 1.390(6) . ?
C45 C46 1.402(6) . ?
C46 C47 1.399(6) . ?
C46 C52 1.509(6) . ?
C47 C48 1.376(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.398(5) . ?
C48 C53 1.516(6) . ?
C49 C50 1.381(5) . ?
C49 H49 0.9300 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 C55 1.533(5) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C55 C56 1.550(6) . ?
C57 C58 1.495(6) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?

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
C26 O3 H3 109.5 . . ?
C27 O4 C28 117.6(4) . . ?
C1 N1 C8 111.7(3) . . ?
C1 N1 C9 122.9(4) . . ?
C8 N1 C9 125.5(4) . . ?
C10 N2 C13 108.5(3) . . ?
C10 N2 C14 127.1(3) . . ?
C13 N2 C14 122.8(4) . . ?
C15 N3 C16 111.8(3) . . ?
C15 N3 C22 120.8(4) . . ?
C16 N3 C22 127.1(4) . . ?
O1 C1 N1 125.1(4) . . ?
O1 C1 C2 126.5(4) . . ?
N1 C1 C2 108.3(3) . . ?
C10 C2 C3 111.4(3) . . ?
C10 C2 C25 110.0(3) . . ?
C3 C2 C25 111.8(3) . . ?
C10 C2 C1 109.7(3) . . ?
C3 C2 C1 101.2(3) . . ?
C25 C2 C1 112.4(3) . . ?
C4 C3 C8 120.1(4) . . ?
C4 C3 C2 130.9(4) . . ?
C8 C3 C2 109.1(3) . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.9(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 117.1(4) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C3 122.1(4) . . ?
C7 C8 N1 128.2(4) . . ?
C3 C8 N1 109.7(4) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 107.4(4) . . ?
C11 C10 C2 130.9(4) . . ?
N2 C10 C2 121.7(4) . . ?
C10 C11 C12 108.4(4) . . ?
C10 C11 H11 125.8 . . ?
C12 C11 H11 125.8 . . ?
C13 C12 C11 106.8(4) . . ?
C13 C12 H12 126.6 . . ?
C11 C12 H12 126.6 . . ?
C12 C13 N2 108.9(4) . . ?
C12 C13 H13 125.5 . . ?
N2 C13 H13 125.5 . . ?
N2 C14 C21 112.1(3) . . ?
N2 C14 C15 109.3(3) . . ?
C21 C14 C15 102.0(3) . . ?
N2 C14 C26 110.2(3) . . ?
C21 C14 C26 112.8(3) . . ?
C15 C14 C26 110.2(3) . . ?
O2 C15 N3 125.8(4) . . ?
O2 C15 C14 126.1(4) . . ?
N3 C15 C14 108.0(4) . . ?
C17 C16 C21 121.6(4) . . ?
C17 C16 N3 129.8(4) . . ?
C21 C16 N3 108.5(4) . . ?
C16 C17 C18 115.5(4) . . ?
C16 C17 C23 125.6(4) . . ?
C18 C17 C23 118.9(4) . . ?
C19 C18 C17 124.6(4) . . ?
C19 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
C18 C19 C20 117.7(4) . . ?
C18 C19 C24 120.9(4) . . ?
C20 C19 C24 121.4(4) . . ?
C21 C20 C19 119.5(4) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C16 120.9(4) . . ?
C20 C21 C14 130.1(4) . . ?
C16 C21 C14 109.0(3) . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C2 115.3(3) . . ?
C26 C25 H25A 108.4 . . ?
C2 C25 H25A 108.4 . . ?
C26 C25 H25B 108.4 . . ?
C2 C25 H25B 108.4 . . ?
H25A C25 H25B 107.5 . . ?
O3 C26 C25 112.1(3) . . ?
O3 C26 C27 105.4(3) . . ?
C25 C26 C27 108.3(3) . . ?
O3 C26 C14 112.5(3) . . ?
C25 C26 C14 109.9(3) . . ?
C27 C26 C14 108.4(3) . . ?
O5 C27 O4 125.4(4) . . ?
O5 C27 C26 124.1(4) . . ?
O4 C27 C26 110.5(4) . . ?
C29 C28 O4 108.0(4) . . ?
C29 C28 H28A 110.1 . . ?
O4 C28 H28A 110.1 . . ?
C29 C28 H28B 110.1 . . ?
O4 C28 H28B 110.1 . . ?
H28A C28 H28B 108.4 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C55 O8 H8 109.5 . . ?
C56 O9 C57 116.5(3) . . ?
C30 N4 C37 110.9(4) . . ?
C30 N4 C38 124.2(4) . . ?
C37 N4 C38 124.9(4) . . ?
C39 N5 C42 108.3(4) . . ?
C39 N5 C43 126.5(3) . . ?
C42 N5 C43 123.1(3) . . ?
C44 N6 C45 112.1(3) . . ?
C44 N6 C51 119.9(4) . . ?
C45 N6 C51 127.8(4) . . ?
O6 C30 N4 125.2(4) . . ?
O6 C30 C31 126.0(4) . . ?
N4 C30 C31 108.8(4) . . ?
C39 C31 C32 111.4(3) . . ?
C39 C31 C30 110.1(4) . . ?
C32 C31 C30 101.3(3) . . ?
C39 C31 C54 111.1(3) . . ?
C32 C31 C54 113.0(3) . . ?
C30 C31 C54 109.5(3) . . ?
C33 C32 C37 119.7(4) . . ?
C33 C32 C31 131.1(4) . . ?
C37 C32 C31 109.1(4) . . ?
C32 C33 C34 119.7(4) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C35 C34 C33 119.7(5) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 121.4(5) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C37 C36 C35 117.4(4) . . ?
C37 C36 H36 121.3 . . ?
C35 C36 H36 121.3 . . ?
C32 C37 C36 122.0(4) . . ?
C32 C37 N4 109.7(4) . . ?
C36 C37 N4 128.2(4) . . ?
N4 C38 H38A 109.5 . . ?
N4 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N4 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 N5 108.1(4) . . ?
C40 C39 C31 130.1(4) . . ?
N5 C39 C31 121.6(4) . . ?
C39 C40 C41 107.5(4) . . ?
C39 C40 H40 126.2 . . ?
C41 C40 H40 126.2 . . ?
C42 C41 C40 107.4(4) . . ?
C42 C41 H41 126.3 . . ?
C40 C41 H41 126.3 . . ?
C41 C42 N5 108.6(4) . . ?
C41 C42 H42 125.7 . . ?
N5 C42 H42 125.7 . . ?
N5 C43 C50 111.0(3) . . ?
N5 C43 C44 107.1(3) . . ?
C50 C43 C44 101.9(3) . . ?
N5 C43 C55 108.0(3) . . ?
C50 C43 C55 114.8(3) . . ?
C44 C43 C55 113.8(3) . . ?
O7 C44 N6 124.9(4) . . ?
O7 C44 C43 127.4(4) . . ?
N6 C44 C43 107.5(4) . . ?
C50 C45 C46 121.8(4) . . ?
C50 C45 N6 109.1(3) . . ?
C46 C45 N6 129.0(4) . . ?
C47 C46 C45 115.1(4) . . ?
C47 C46 C52 119.5(4) . . ?
C45 C46 C52 125.3(4) . . ?
C48 C47 C46 124.5(4) . . ?
C48 C47 H47 117.8 . . ?
C46 C47 H47 117.8 . . ?
C47 C48 C49 118.3(4) . . ?
C47 C48 C53 122.1(4) . . ?
C49 C48 C53 119.6(4) . . ?
C50 C49 C48 119.4(4) . . ?
C50 C49 H49 120.3 . . ?
C48 C49 H49 120.3 . . ?
C49 C50 C45 120.7(4) . . ?
C49 C50 C43 130.1(4) . . ?
C45 C50 C43 109.2(3) . . ?
N6 C51 H51A 109.5 . . ?
N6 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N6 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C46 C52 H52A 109.5 . . ?
C46 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C46 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C48 C53 H53A 109.5 . . ?
C48 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C48 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C55 C54 C31 115.6(3) . . ?
C55 C54 H54A 108.4 . . ?
C31 C54 H54A 108.4 . . ?
C55 C54 H54B 108.4 . . ?
C31 C54 H54B 108.4 . . ?
H54A C54 H54B 107.4 . . ?
O8 C55 C54 111.7(3) . . ?
O8 C55 C56 104.6(3) . . ?
C54 C55 C56 108.2(3) . . ?
O8 C55 C43 110.5(3) . . ?
C54 C55 C43 111.1(3) . . ?
C56 C55 C43 110.4(3) . . ?
O10 C56 O9 123.6(4) . . ?
O10 C56 C55 123.9(4) . . ?
O9 C56 C55 112.5(4) . . ?
O9 C57 C58 108.3(4) . . ?
O9 C57 H57A 110.0 . . ?
C58 C57 H57A 110.0 . . ?
O9 C57 H57B 110.0 . . ?
C58 C57 H57B 110.0 . . ?
H57A C57 H57B 108.4 . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 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
C8 N1 C1 O1 -179.3(4) . . . . ?
C9 N1 C1 O1 -0.5(7) . . . . ?
C8 N1 C1 C2 1.8(5) . . . . ?
C9 N1 C1 C2 -179.4(4) . . . . ?
O1 C1 C2 C10 -63.1(5) . . . . ?
N1 C1 C2 C10 115.8(4) . . . . ?
O1 C1 C2 C3 179.1(4) . . . . ?
N1 C1 C2 C3 -2.0(4) . . . . ?
O1 C1 C2 C25 59.7(6) . . . . ?
N1 C1 C2 C25 -121.4(4) . . . . ?
C10 C2 C3 C4 65.1(6) . . . . ?
C25 C2 C3 C4 -58.4(6) . . . . ?
C1 C2 C3 C4 -178.3(4) . . . . ?
C10 C2 C3 C8 -115.1(4) . . . . ?
C25 C2 C3 C8 121.4(4) . . . . ?
C1 C2 C3 C8 1.5(4) . . . . ?
C8 C3 C4 C5 1.4(6) . . . . ?
C2 C3 C4 C5 -178.8(4) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C5 C6 C7 C8 0.5(7) . . . . ?
C6 C7 C8 C3 -0.1(7) . . . . ?
C6 C7 C8 N1 179.9(4) . . . . ?
C4 C3 C8 C7 -0.8(6) . . . . ?
C2 C3 C8 C7 179.4(4) . . . . ?
C4 C3 C8 N1 179.2(4) . . . . ?
C2 C3 C8 N1 -0.6(5) . . . . ?
C1 N1 C8 C7 179.3(4) . . . . ?
C9 N1 C8 C7 0.5(7) . . . . ?
C1 N1 C8 C3 -0.8(5) . . . . ?
C9 N1 C8 C3 -179.5(4) . . . . ?
C13 N2 C10 C11 -2.2(4) . . . . ?
C14 N2 C10 C11 -167.8(4) . . . . ?
C13 N2 C10 C2 -179.1(4) . . . . ?
C14 N2 C10 C2 15.3(6) . . . . ?
C3 C2 C10 C11 35.8(6) . . . . ?
C25 C2 C10 C11 160.3(4) . . . . ?
C1 C2 C10 C11 -75.5(5) . . . . ?
C3 C2 C10 N2 -148.1(4) . . . . ?
C25 C2 C10 N2 -23.6(5) . . . . ?
C1 C2 C10 N2 100.6(4) . . . . ?
N2 C10 C11 C12 1.6(5) . . . . ?
C2 C10 C11 C12 178.1(4) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 N2 -1.0(5) . . . . ?
C10 N2 C13 C12 2.0(5) . . . . ?
C14 N2 C13 C12 168.4(4) . . . . ?
C10 N2 C14 C21 102.3(4) . . . . ?
C13 N2 C14 C21 -61.4(5) . . . . ?
C10 N2 C14 C15 -145.4(4) . . . . ?
C13 N2 C14 C15 50.8(5) . . . . ?
C10 N2 C14 C26 -24.2(5) . . . . ?
C13 N2 C14 C26 172.0(4) . . . . ?
C16 N3 C15 O2 -171.4(4) . . . . ?
C22 N3 C15 O2 2.7(7) . . . . ?
C16 N3 C15 C14 6.0(5) . . . . ?
C22 N3 C15 C14 -179.9(4) . . . . ?
N2 C14 C15 O2 50.6(6) . . . . ?
C21 C14 C15 O2 169.4(4) . . . . ?
C26 C14 C15 O2 -70.6(6) . . . . ?
N2 C14 C15 N3 -126.8(4) . . . . ?
C21 C14 C15 N3 -8.0(4) . . . . ?
C26 C14 C15 N3 112.0(4) . . . . ?
C15 N3 C16 C17 176.8(5) . . . . ?
C22 N3 C16 C17 3.0(7) . . . . ?
C15 N3 C16 C21 -1.1(5) . . . . ?
C22 N3 C16 C21 -174.8(4) . . . . ?
C21 C16 C17 C18 3.2(6) . . . . ?
N3 C16 C17 C18 -174.4(4) . . . . ?
C21 C16 C17 C23 -177.5(5) . . . . ?
N3 C16 C17 C23 4.9(8) . . . . ?
C16 C17 C18 C19 0.1(7) . . . . ?
C23 C17 C18 C19 -179.2(5) . . . . ?
C17 C18 C19 C20 -2.9(7) . . . . ?
C17 C18 C19 C24 177.3(5) . . . . ?
C18 C19 C20 C21 2.4(6) . . . . ?
C24 C19 C20 C21 -177.8(4) . . . . ?
C19 C20 C21 C16 0.8(6) . . . . ?
C19 C20 C21 C14 179.2(4) . . . . ?
C17 C16 C21 C20 -3.7(6) . . . . ?
N3 C16 C21 C20 174.3(4) . . . . ?
C17 C16 C21 C14 177.6(4) . . . . ?
N3 C16 C21 C14 -4.4(4) . . . . ?
N2 C14 C21 C20 -54.4(5) . . . . ?
C15 C14 C21 C20 -171.2(4) . . . . ?
C26 C14 C21 C20 70.7(5) . . . . ?
N2 C14 C21 C16 124.2(4) . . . . ?
C15 C14 C21 C16 7.4(4) . . . . ?
C26 C14 C21 C16 -110.7(4) . . . . ?
C10 C2 C25 C26 45.9(4) . . . . ?
C3 C2 C25 C26 170.2(3) . . . . ?
C1 C2 C25 C26 -76.7(4) . . . . ?
C2 C25 C26 O3 69.0(4) . . . . ?
C2 C25 C26 C27 -175.1(3) . . . . ?
C2 C25 C26 C14 -56.9(4) . . . . ?
N2 C14 C26 O3 -83.2(4) . . . . ?
C21 C14 C26 O3 150.7(3) . . . . ?
C15 C14 C26 O3 37.5(5) . . . . ?
N2 C14 C26 C25 42.5(4) . . . . ?
C21 C14 C26 C25 -83.6(4) . . . . ?
C15 C14 C26 C25 163.1(3) . . . . ?
N2 C14 C26 C27 160.6(3) . . . . ?
C21 C14 C26 C27 34.5(4) . . . . ?
C15 C14 C26 C27 -78.7(4) . . . . ?
C28 O4 C27 O5 1.2(7) . . . . ?
C28 O4 C27 C26 -178.9(4) . . . . ?
O3 C26 C27 O5 132.2(4) . . . . ?
C25 C26 C27 O5 12.1(6) . . . . ?
C14 C26 C27 O5 -107.1(5) . . . . ?
O3 C26 C27 O4 -47.8(4) . . . . ?
C25 C26 C27 O4 -167.9(3) . . . . ?
C14 C26 C27 O4 72.9(4) . . . . ?
C27 O4 C28 C29 -147.6(5) . . . . ?
C37 N4 C30 O6 -178.3(4) . . . . ?
C38 N4 C30 O6 2.2(7) . . . . ?
C37 N4 C30 C31 3.1(5) . . . . ?
C38 N4 C30 C31 -176.4(4) . . . . ?
O6 C30 C31 C39 60.6(6) . . . . ?
N4 C30 C31 C39 -120.9(4) . . . . ?
O6 C30 C31 C32 178.5(4) . . . . ?
N4 C30 C31 C32 -2.9(4) . . . . ?
O6 C30 C31 C54 -61.9(6) . . . . ?
N4 C30 C31 C54 116.7(4) . . . . ?
C39 C31 C32 C33 -58.2(6) . . . . ?
C30 C31 C32 C33 -175.2(4) . . . . ?
C54 C31 C32 C33 67.7(6) . . . . ?
C39 C31 C32 C37 118.7(4) . . . . ?
C30 C31 C32 C37 1.7(4) . . . . ?
C54 C31 C32 C37 -115.4(4) . . . . ?
C37 C32 C33 C34 0.2(6) . . . . ?
C31 C32 C33 C34 176.9(4) . . . . ?
C32 C33 C34 C35 0.8(7) . . . . ?
C33 C34 C35 C36 -1.1(8) . . . . ?
C34 C35 C36 C37 0.5(7) . . . . ?
C33 C32 C37 C36 -1.0(7) . . . . ?
C31 C32 C37 C36 -178.3(4) . . . . ?
C33 C32 C37 N4 177.4(4) . . . . ?
C31 C32 C37 N4 0.0(5) . . . . ?
C35 C36 C37 C32 0.6(7) . . . . ?
C35 C36 C37 N4 -177.4(5) . . . . ?
C30 N4 C37 C32 -2.1(5) . . . . ?
C38 N4 C37 C32 177.4(4) . . . . ?
C30 N4 C37 C36 176.1(5) . . . . ?
C38 N4 C37 C36 -4.4(7) . . . . ?
C42 N5 C39 C40 1.6(5) . . . . ?
C43 N5 C39 C40 165.5(4) . . . . ?
C42 N5 C39 C31 176.9(4) . . . . ?
C43 N5 C39 C31 -19.2(6) . . . . ?
C32 C31 C39 C40 -40.6(6) . . . . ?
C30 C31 C39 C40 70.9(6) . . . . ?
C54 C31 C39 C40 -167.6(4) . . . . ?
C32 C31 C39 N5 145.3(4) . . . . ?
C30 C31 C39 N5 -103.2(4) . . . . ?
C54 C31 C39 N5 18.3(5) . . . . ?
N5 C39 C40 C41 -1.0(5) . . . . ?
C31 C39 C40 C41 -175.7(4) . . . . ?
C39 C40 C41 C42 0.0(5) . . . . ?
C40 C41 C42 N5 1.0(5) . . . . ?
C39 N5 C42 C41 -1.6(5) . . . . ?
C43 N5 C42 C41 -166.2(4) . . . . ?
C39 N5 C43 C50 -92.8(5) . . . . ?
C42 N5 C43 C50 68.9(5) . . . . ?
C39 N5 C43 C44 156.8(4) . . . . ?
C42 N5 C43 C44 -41.5(5) . . . . ?
C39 N5 C43 C55 33.8(5) . . . . ?
C42 N5 C43 C55 -164.5(4) . . . . ?
C45 N6 C44 O7 177.8(4) . . . . ?
C51 N6 C44 O7 -6.9(7) . . . . ?
C45 N6 C44 C43 2.3(5) . . . . ?
C51 N6 C44 C43 177.5(4) . . . . ?
N5 C43 C44 O7 -62.7(5) . . . . ?
C50 C43 C44 O7 -179.3(4) . . . . ?
C55 C43 C44 O7 56.6(6) . . . . ?
N5 C43 C44 N6 112.8(4) . . . . ?
C50 C43 C44 N6 -3.9(4) . . . . ?
C55 C43 C44 N6 -128.0(4) . . . . ?
C44 N6 C45 C50 0.6(5) . . . . ?
C51 N6 C45 C50 -174.3(4) . . . . ?
C44 N6 C45 C46 -176.3(4) . . . . ?
C51 N6 C45 C46 8.8(7) . . . . ?
C50 C45 C46 C47 4.8(6) . . . . ?
N6 C45 C46 C47 -178.6(4) . . . . ?
C50 C45 C46 C52 -172.4(4) . . . . ?
N6 C45 C46 C52 4.1(7) . . . . ?
C45 C46 C47 C48 -1.6(6) . . . . ?
C52 C46 C47 C48 175.8(4) . . . . ?
C46 C47 C48 C49 -2.4(7) . . . . ?
C46 C47 C48 C53 176.4(4) . . . . ?
C47 C48 C49 C50 3.3(6) . . . . ?
C53 C48 C49 C50 -175.5(4) . . . . ?
C48 C49 C50 C45 -0.2(6) . . . . ?
C48 C49 C50 C43 -177.8(4) . . . . ?
C46 C45 C50 C49 -4.1(6) . . . . ?
N6 C45 C50 C49 178.8(4) . . . . ?
C46 C45 C50 C43 174.0(4) . . . . ?
N6 C45 C50 C43 -3.2(5) . . . . ?
N5 C43 C50 C49 68.4(5) . . . . ?
C44 C43 C50 C49 -177.9(4) . . . . ?
C55 C43 C50 C49 -54.5(6) . . . . ?
N5 C43 C50 C45 -109.4(4) . . . . ?
C44 C43 C50 C45 4.3(4) . . . . ?
C55 C43 C50 C45 127.7(4) . . . . ?
C39 C31 C54 C55 -37.4(5) . . . . ?
C32 C31 C54 C55 -163.5(3) . . . . ?
C30 C31 C54 C55 84.4(4) . . . . ?
C31 C54 C55 O8 -68.9(4) . . . . ?
C31 C54 C55 C56 176.5(3) . . . . ?
C31 C54 C55 C43 55.1(4) . . . . ?
N5 C43 C55 O8 75.6(4) . . . . ?
C50 C43 C55 O8 -160.0(3) . . . . ?
C44 C43 C55 O8 -43.2(4) . . . . ?
N5 C43 C55 C54 -49.0(4) . . . . ?
C50 C43 C55 C54 75.4(4) . . . . ?
C44 C43 C55 C54 -167.8(3) . . . . ?
N5 C43 C55 C56 -169.1(3) . . . . ?
C50 C43 C55 C56 -44.7(4) . . . . ?
C44 C43 C55 C56 72.1(4) . . . . ?
C57 O9 C56 O10 -0.5(6) . . . . ?
C57 O9 C56 C55 -178.4(3) . . . . ?
O8 C55 C56 O10 -107.1(5) . . . . ?
C54 C55 C56 O10 12.2(6) . . . . ?
C43 C55 C56 O10 134.0(5) . . . . ?
O8 C55 C56 O9 70.9(4) . . . . ?
C54 C55 C56 O9 -169.9(3) . . . . ?
C43 C55 C56 O9 -48.0(4) . . . . ?
C56 O9 C57 C58 -162.7(4) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_b170113a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1539270'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cl2 F N3 O5'
_chemical_formula_weight         572.40

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.2486(5)
_cell_length_b                   10.5812(5)
_cell_length_c                   21.0573(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.509(2)
_cell_angle_gamma                90
_cell_volume                     2724.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9762
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.600
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.846
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65836
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.546
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6251
_reflns_number_gt                5111
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+2.7904P] 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         6251
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.3114
_refine_ls_wR_factor_gt          0.2893
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2081(2) 0.6558(2) 0.31937(13) 0.0204(5) Uani 1 1 d . . . . .
C2 C 0.2086(2) 0.5540(2) 0.37264(12) 0.0175(5) Uani 1 1 d . . . . .
C3 C 0.1503(2) 0.6232(2) 0.42417(13) 0.0216(6) Uani 1 1 d . . . . .
C4 C 0.1150(2) 0.5832(3) 0.48171(15) 0.0289(6) Uani 1 1 d . . . . .
H4 H 0.1257 0.5001 0.4950 0.035 Uiso 1 1 calc R U . . .
C5 C 0.0628(3) 0.6698(4) 0.51970(16) 0.0383(8) Uani 1 1 d . . . . .
H5 H 0.0386 0.6436 0.5586 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0466(3) 0.7936(4) 0.50061(19) 0.0428(9) Uani 1 1 d . . . . .
H6 H 0.0126 0.8506 0.5266 0.051 Uiso 1 1 calc R U . . .
C7 C 0.0814(3) 0.8319(3) 0.44256(18) 0.0371(8) Uani 1 1 d . . . . .
C8 C 0.1330(2) 0.7482(3) 0.40387(15) 0.0256(6) Uani 1 1 d . . . . .
C9 C 0.1710(3) 0.8846(3) 0.30858(18) 0.0361(7) Uani 1 1 d . . . . .
H9A H 0.2083 0.8732 0.2702 0.054 Uiso 1 1 calc R U . . .
H9B H 0.2084 0.9475 0.3346 0.054 Uiso 1 1 calc R U . . .
H9C H 0.0973 0.9118 0.2981 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1497(2) 0.4367(2) 0.34860(11) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.0440(2) 0.4223(3) 0.32415(13) 0.0240(6) Uani 1 1 d . . . . .
H11 H -0.0071 0.4866 0.3169 0.029 Uiso 1 1 calc R U . . .
C12 C 0.0267(2) 0.2921(3) 0.31192(15) 0.0284(6) Uani 1 1 d . . . . .
H12 H -0.0378 0.2552 0.2954 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1220(2) 0.2304(2) 0.32887(15) 0.0266(6) Uani 1 1 d . . . . .
H13 H 0.1341 0.1440 0.3255 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3119(2) 0.2925(2) 0.36917(12) 0.0183(5) Uani 1 1 d . . . . .
C15 C 0.3777(2) 0.2962(2) 0.30764(13) 0.0223(5) Uani 1 1 d . . . . .
C16 C 0.4101(2) 0.1044(3) 0.35432(15) 0.0273(6) Uani 1 1 d . . . . .
C17 C 0.4532(3) -0.0151(3) 0.3667(2) 0.0400(8) Uani 1 1 d . . . . .
H17 H 0.5032 -0.0513 0.3406 0.048 Uiso 1 1 calc R U . . .
C18 C 0.4191(3) -0.0780(3) 0.4192(2) 0.0459(9) Uani 1 1 d . . . . .
H18 H 0.4469 -0.1580 0.4286 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3449(3) -0.0252(3) 0.45794(19) 0.0434(9) Uani 1 1 d . . . . .
H19 H 0.3234 -0.0700 0.4930 0.052 Uiso 1 1 calc R U . . .
C20 C 0.3015(3) 0.0953(3) 0.44515(16) 0.0320(7) Uani 1 1 d . . . . .
H20 H 0.2507 0.1305 0.4710 0.038 Uiso 1 1 calc R U . . .
C21 C 0.3358(2) 0.1603(2) 0.39363(14) 0.0237(6) Uani 1 1 d . . . . .
C22 C 0.4987(3) 0.1520(4) 0.2515(2) 0.0467(9) Uani 1 1 d . . . . .
H22A H 0.4976 0.2207 0.2217 0.070 Uiso 1 1 calc R U . . .
H22B H 0.4702 0.0773 0.2306 0.070 Uiso 1 1 calc R U . . .
H22C H 0.5725 0.1369 0.2677 0.070 Uiso 1 1 calc R U . . .
C23 C 0.3314(2) 0.5275(2) 0.39101(12) 0.0183(5) Uani 1 1 d . . . . .
H23A H 0.3729 0.5364 0.3535 0.022 Uiso 1 1 calc R U . . .
H23B H 0.3582 0.5899 0.4219 0.022 Uiso 1 1 calc R U . . .
C24 C 0.3504(2) 0.3957(2) 0.41890(12) 0.0195(5) Uani 1 1 d . . . . .
C25 C 0.4715(2) 0.3752(2) 0.44012(14) 0.0242(6) Uani 1 1 d . . . . .
C26 C 0.6538(3) 0.3688(4) 0.4094(2) 0.0490(10) Uani 1 1 d . . . . .
H26A H 0.6823 0.4269 0.4420 0.059 Uiso 1 1 calc R U . . .
H26B H 0.6634 0.2833 0.4255 0.059 Uiso 1 1 calc R U . . .
C27 C 0.7112(4) 0.3843(7) 0.3531(3) 0.0794(17) Uani 1 1 d . . . . .
H27A H 0.6753 0.3366 0.3191 0.119 Uiso 1 1 calc R U . . .
H27B H 0.7849 0.3545 0.3605 0.119 Uiso 1 1 calc R U . . .
H27C H 0.7121 0.4721 0.3416 0.119 Uiso 1 1 calc R U . . .
C28 C 0.1824(5) 0.3975(7) 0.1677(3) 0.0806(17) Uani 1 1 d . . . . .
Cl1 Cl 0.1767(5) 0.2340(5) 0.1532(3) 0.1178(14) Uiso 0.5 1 d . . P A 1
Cl2 Cl 0.2032(4) 0.5224(4) 0.1111(2) 0.0951(11) Uiso 0.5 1 d . . P A 1
Cl2A Cl 0.2369(5) 0.4704(6) 0.1079(3) 0.1198(15) Uiso 0.5 1 d . . P A 2
Cl1A Cl 0.2286(7) 0.2536(7) 0.1338(4) 0.161(2) Uiso 0.5 1 d . . P A 2
F1 F 0.0642(2) 0.9533(2) 0.42255(14) 0.0585(7) Uani 1 1 d . . . . .
N1 N 0.1695(2) 0.7662(2) 0.34300(13) 0.0268(5) Uani 1 1 d . . . . .
N2 N 0.19722(17) 0.3189(2) 0.35195(11) 0.0189(5) Uani 1 1 d . . . . .
N3 N 0.4317(2) 0.1841(2) 0.30382(13) 0.0287(6) Uani 1 1 d . . . . .
O1 O 0.23920(19) 0.6427(2) 0.26618(10) 0.0316(5) Uani 1 1 d . . . . .
O2 O 0.37832(18) 0.38091(19) 0.26912(10) 0.0288(5) Uani 1 1 d . . . . .
O3 O 0.28948(17) 0.3808(2) 0.47321(9) 0.0264(5) Uani 1 1 d . . . . .
H3 H 0.3262 0.3422 0.5007 0.040 Uiso 1 1 calc R U . . .
O4 O 0.53681(16) 0.3943(2) 0.39417(11) 0.0337(5) Uani 1 1 d . . . . .
O5 O 0.49914(19) 0.3440(2) 0.49387(11) 0.0374(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.213(3) . ?
C1 N1 1.366(3) . ?
C1 C2 1.555(3) . ?
C2 C10 1.507(3) . ?
C2 C3 1.523(3) . ?
C2 C23 1.555(3) . ?
C3 C4 1.378(4) . ?
C3 C8 1.402(4) . ?
C4 C5 1.397(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(6) . ?
C6 H6 0.9300 . ?
C7 F1 1.365(4) . ?
C7 C8 1.382(4) . ?
C8 N1 1.396(4) . ?
C9 N1 1.448(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.373(4) . ?
C10 N2 1.376(3) . ?
C11 C12 1.416(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(4) . ?
C12 H12 0.9300 . ?
C13 N2 1.380(3) . ?
C13 H13 0.9300 . ?
C14 N2 1.456(3) . ?
C14 C21 1.514(3) . ?
C14 C24 1.565(3) . ?
C14 C15 1.567(4) . ?
C15 O2 1.209(4) . ?
C15 N3 1.363(3) . ?
C16 C17 1.390(4) . ?
C16 N3 1.394(4) . ?
C16 C21 1.398(4) . ?
C17 C18 1.376(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9300 . ?
C22 N3 1.453(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.525(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O3 1.412(3) . ?
C24 C25 1.538(3) . ?
C25 O5 1.207(4) . ?
C25 O4 1.308(4) . ?
C26 C27 1.426(7) . ?
C26 O4 1.474(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 Cl2A 1.653(8) . ?
C28 Cl1 1.757(9) . ?
C28 Cl1A 1.789(10) . ?
C28 Cl2 1.809(8) . ?
O3 H3 0.8200 . ?

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
O1 C1 N1 124.7(2) . . ?
O1 C1 C2 126.9(2) . . ?
N1 C1 C2 108.4(2) . . ?
C10 C2 C3 113.6(2) . . ?
C10 C2 C1 110.3(2) . . ?
C3 C2 C1 101.5(2) . . ?
C10 C2 C23 111.75(19) . . ?
C3 C2 C23 113.5(2) . . ?
C1 C2 C23 105.38(19) . . ?
C4 C3 C8 120.6(3) . . ?
C4 C3 C2 131.7(3) . . ?
C8 C3 C2 107.8(2) . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
F1 C7 C6 120.0(3) . . ?
F1 C7 C8 119.3(3) . . ?
C6 C7 C8 120.8(3) . . ?
C7 C8 N1 129.6(3) . . ?
C7 C8 C3 119.4(3) . . ?
N1 C8 C3 111.0(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 107.7(2) . . ?
C11 C10 C2 129.7(2) . . ?
N2 C10 C2 122.5(2) . . ?
C10 C11 C12 107.6(2) . . ?
C10 C11 H11 126.2 . . ?
C12 C11 H11 126.2 . . ?
C13 C12 C11 107.6(2) . . ?
C13 C12 H12 126.2 . . ?
C11 C12 H12 126.2 . . ?
C12 C13 N2 108.0(2) . . ?
C12 C13 H13 126.0 . . ?
N2 C13 H13 126.0 . . ?
N2 C14 C21 115.1(2) . . ?
N2 C14 C24 106.25(19) . . ?
C21 C14 C24 111.9(2) . . ?
N2 C14 C15 109.0(2) . . ?
C21 C14 C15 101.9(2) . . ?
C24 C14 C15 112.7(2) . . ?
O2 C15 N3 125.6(3) . . ?
O2 C15 C14 126.7(2) . . ?
N3 C15 C14 107.6(2) . . ?
C17 C16 N3 127.3(3) . . ?
C17 C16 C21 121.8(3) . . ?
N3 C16 C21 110.9(2) . . ?
C18 C17 C16 117.4(3) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C19 121.6(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 118.5(3) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C16 119.9(3) . . ?
C20 C21 C14 132.1(3) . . ?
C16 C21 C14 108.0(2) . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C2 112.6(2) . . ?
C24 C23 H23A 109.1 . . ?
C2 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C2 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
O3 C24 C23 109.7(2) . . ?
O3 C24 C25 107.3(2) . . ?
C23 C24 C25 111.3(2) . . ?
O3 C24 C14 108.1(2) . . ?
C23 C24 C14 110.3(2) . . ?
C25 C24 C14 110.0(2) . . ?
O5 C25 O4 125.9(3) . . ?
O5 C25 C24 121.4(3) . . ?
O4 C25 C24 112.7(2) . . ?
C27 C26 O4 108.6(4) . . ?
C27 C26 H26A 110.0 . . ?
O4 C26 H26A 110.0 . . ?
C27 C26 H26B 110.0 . . ?
O4 C26 H26B 110.0 . . ?
H26A C26 H26B 108.3 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Cl2A C28 Cl1A 86.6(4) . . ?
Cl1 C28 Cl2 127.6(4) . . ?
C1 N1 C8 110.8(2) . . ?
C1 N1 C9 122.9(3) . . ?
C8 N1 C9 126.3(3) . . ?
C10 N2 C13 109.0(2) . . ?
C10 N2 C14 125.8(2) . . ?
C13 N2 C14 124.8(2) . . ?
C15 N3 C16 111.5(2) . . ?
C15 N3 C22 123.1(3) . . ?
C16 N3 C22 125.4(3) . . ?
C24 O3 H3 109.5 . . ?
C25 O4 C26 116.1(3) . . ?

_refine_diff_density_max         1.147
_refine_diff_density_min         -1.638
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_g170505d
_database_code_depnum_ccdc_archive 'CCDC 1548552'
_audit_update_record             
;
2017-05-06 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;
_audit_creation_date             2017-05-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29 N3 O5'
_chemical_formula_sum            'C29 H29 N3 O5'
_chemical_formula_weight         499.55
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.6120(5)
_cell_length_b                   9.9405(4)
_cell_length_c                   52.933(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5057.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3129
_cell_measurement_temperature    210.01(10)
_cell_measurement_theta_max      72.3870
_cell_measurement_theta_min      4.5040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0932
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            18051
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.526
_diffrn_ambient_temperature      210.01(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -113.00  -11.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  -57.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2343    0.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega   44.00   71.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   29.00   90.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00   99.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   97.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522 -111.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega   33.00   95.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000 -120.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   90.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega  148.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  114.0000  -80.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega  122.00  175.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  111.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega -114.00  -60.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  -57.0000  -30.0000 54
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0919468000
_diffrn_orient_matrix_UB_12      0.0560058000
_diffrn_orient_matrix_UB_13      -0.0213975000
_diffrn_orient_matrix_UB_21      0.1281992000
_diffrn_orient_matrix_UB_22      -0.0088503000
_diffrn_orient_matrix_UB_23      0.0173860000
_diffrn_orient_matrix_UB_31      0.0277541000
_diffrn_orient_matrix_UB_32      -0.1442318000
_diffrn_orient_matrix_UB_33      -0.0093779000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6565
_reflns_number_total             9040
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         9040
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1169
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B), C46(H46A,H46B), C49(H49A,H49B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C12(H12), C13(H13), C14(H14), C25(H25), C26(H26), C27(H27),
 C28(H28), C31(H31), C33(H33), C41(H41), C42(H42), C43(H43), C54(H54), C55(H55),
  C56(H56), C57(H57)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C),
 C23(H23A,H23B,H23C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C40(H40A,H40B,
 H40C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9136(4) 0.9917(3) 0.30061(7) 0.0388(9) Uani 1 1 d . . . . .
O2 O 0.6682(4) 0.8537(3) 0.31935(7) 0.0360(8) Uani 1 1 d . . . . .
H2 H 0.6314 0.8403 0.3054 0.054 Uiso 1 1 calc GR . . . .
O3 O 0.7899(5) 0.6683(4) 0.36869(7) 0.0547(11) Uani 1 1 d . . . . .
O4 O 0.8273(4) 0.8852(3) 0.35897(7) 0.0437(9) Uani 1 1 d . . . . .
O5 O 0.4949(4) 0.7578(3) 0.28388(7) 0.0425(9) Uani 1 1 d . . . . .
N1 N 1.0877(4) 0.8787(3) 0.32155(7) 0.0291(9) Uani 1 1 d . . . . .
N2 N 0.8605(4) 0.7120(4) 0.28351(7) 0.0297(9) Uani 1 1 d . . . . .
N3 N 0.4251(5) 0.5381(4) 0.27843(8) 0.0388(10) Uani 1 1 d . . . . .
C1 C 1.2349(5) 0.6925(5) 0.34031(9) 0.0318(11) Uani 1 1 d . . . . .
C2 C 1.2405(6) 0.5521(5) 0.34306(10) 0.0363(12) Uani 1 1 d . . . . .
H2A H 1.3188 0.5138 0.3509 0.044 Uiso 1 1 calc R . . . .
C3 C 1.1347(6) 0.4671(4) 0.33470(10) 0.0375(13) Uani 1 1 d . . . . .
C4 C 1.0169(5) 0.5230(4) 0.32343(10) 0.0322(11) Uani 1 1 d . . . . .
H4 H 0.9444 0.4673 0.3177 0.039 Uiso 1 1 calc R . . . .
C5 C 1.0077(5) 0.6617(4) 0.32074(9) 0.0269(10) Uani 1 1 d . . . . .
C6 C 1.1176(5) 0.7437(4) 0.32821(9) 0.0278(10) Uani 1 1 d . . . . .
C7 C 1.3521(5) 0.7753(5) 0.35110(11) 0.0419(13) Uani 1 1 d . . . . .
H7A H 1.4113 0.7184 0.3614 0.063 Uiso 1 1 calc GR . . . .
H7B H 1.3140 0.8470 0.3614 0.063 Uiso 1 1 calc GR . . . .
H7C H 1.4062 0.8137 0.3374 0.063 Uiso 1 1 calc GR . . . .
C8 C 1.1468(7) 0.3158(5) 0.33776(14) 0.064(2) Uani 1 1 d . . . . .
H8A H 1.2194 0.2821 0.3267 0.095 Uiso 1 1 calc GR . . . .
H8B H 1.0589 0.2739 0.3334 0.095 Uiso 1 1 calc GR . . . .
H8C H 1.1699 0.2947 0.3551 0.095 Uiso 1 1 calc GR . . . .
C9 C 0.9608(5) 0.8894(4) 0.31001(9) 0.0313(11) Uani 1 1 d . . . . .
C10 C 0.8927(5) 0.7480(4) 0.30970(9) 0.0279(10) Uani 1 1 d . . . . .
C11 C 1.1875(6) 0.9894(5) 0.32079(11) 0.0465(15) Uani 1 1 d . . . . .
H11A H 1.2068 1.0196 0.3379 0.070 Uiso 1 1 calc GR . . . .
H11B H 1.1489 1.0632 0.3111 0.070 Uiso 1 1 calc GR . . . .
H11C H 1.2731 0.9589 0.3129 0.070 Uiso 1 1 calc GR . . . .
C12 C 0.9525(5) 0.7311(5) 0.26388(9) 0.0354(12) Uani 1 1 d . . . . .
H12 H 1.0239 0.7957 0.2635 0.043 Uiso 1 1 calc R . . . .
C13 C 0.9234(6) 0.6415(5) 0.24512(10) 0.0396(13) Uani 1 1 d . . . . .
H13 H 0.9701 0.6330 0.2296 0.048 Uiso 1 1 calc R . . . .
C14 C 0.8078(6) 0.5630(5) 0.25367(10) 0.0380(12) Uani 1 1 d . . . . .
H14 H 0.7639 0.4939 0.2445 0.046 Uiso 1 1 calc R . . . .
C15 C 0.7725(5) 0.6051(4) 0.27713(9) 0.0305(11) Uani 1 1 d . . . . .
C16 C 0.6536(5) 0.5681(4) 0.29410(9) 0.0284(11) Uani 1 1 d . . . . .
C17 C 0.6821(5) 0.6062(4) 0.32199(9) 0.0311(11) Uani 1 1 d . . . . .
H17A H 0.5934 0.6078 0.3311 0.037 Uiso 1 1 calc R . . . .
H17B H 0.7400 0.5360 0.3296 0.037 Uiso 1 1 calc R . . . .
C18 C 0.7548(5) 0.7428(4) 0.32560(9) 0.0294(11) Uani 1 1 d . . . . .
C19 C 0.7916(5) 0.7584(5) 0.35363(10) 0.0342(12) Uani 1 1 d . . . . .
C20 C 0.8614(8) 0.9143(6) 0.38530(10) 0.0576(17) Uani 1 1 d . . . . .
H20A H 0.9323 0.8515 0.3915 0.069 Uiso 1 1 calc R . . . .
H20B H 0.7784 0.9058 0.3959 0.069 Uiso 1 1 calc R . . . .
C21 C 0.9152(8) 1.0554(6) 0.38599(12) 0.066(2) Uani 1 1 d . . . . .
H21A H 0.9990 1.0616 0.3759 0.099 Uiso 1 1 calc GR . . . .
H21B H 0.9362 1.0802 0.4033 0.099 Uiso 1 1 calc GR . . . .
H21C H 0.8452 1.1160 0.3793 0.099 Uiso 1 1 calc GR . . . .
C22 C 0.5162(5) 0.6361(5) 0.28477(10) 0.0357(12) Uani 1 1 d . . . . .
C23 C 0.2839(6) 0.5663(6) 0.26940(11) 0.0516(16) Uani 1 1 d . . . . .
H23A H 0.2169 0.5358 0.2818 0.077 Uiso 1 1 calc GR . . . .
H23B H 0.2683 0.5195 0.2536 0.077 Uiso 1 1 calc GR . . . .
H23C H 0.2731 0.6624 0.2668 0.077 Uiso 1 1 calc GR . . . .
C24 C 0.4789(5) 0.4083(5) 0.28267(10) 0.0351(12) Uani 1 1 d . . . . .
C25 C 0.4156(6) 0.2859(5) 0.27897(10) 0.0439(13) Uani 1 1 d . . . . .
H25 H 0.3236 0.2804 0.2730 0.053 Uiso 1 1 calc R . . . .
C26 C 0.4917(6) 0.1704(5) 0.28428(11) 0.0453(14) Uani 1 1 d . . . . .
H26 H 0.4502 0.0857 0.2819 0.054 Uiso 1 1 calc R . . . .
C27 C 0.6293(6) 0.1776(5) 0.29306(10) 0.0403(13) Uani 1 1 d . . . . .
H27 H 0.6796 0.0987 0.2967 0.048 Uiso 1 1 calc R . . . .
C28 C 0.6904(6) 0.3044(5) 0.29639(10) 0.0378(12) Uani 1 1 d . . . . .
H28 H 0.7831 0.3111 0.3019 0.045 Uiso 1 1 calc R . . . .
C29 C 0.6151(5) 0.4189(5) 0.29158(9) 0.0332(11) Uani 1 1 d . . . . .
O6 O 1.1704(4) 0.3902(4) 0.54850(7) 0.0467(10) Uani 1 1 d . . . . .
O7 O 1.0144(4) 0.5759(3) 0.57656(6) 0.0343(8) Uani 1 1 d . . . . .
H7 H 1.0130 0.6125 0.5625 0.051 Uiso 1 1 calc GR . . . .
O8 O 0.7992(4) 0.4210(4) 0.61833(7) 0.0404(9) Uani 1 1 d . . . . .
O9 O 1.0318(4) 0.4105(4) 0.61422(6) 0.0385(8) Uani 1 1 d . . . . .
O10 O 0.9509(4) 0.7232(3) 0.53613(7) 0.0389(9) Uani 1 1 d . . . . .
N4 N 1.0998(4) 0.1970(4) 0.56835(8) 0.0335(10) Uani 1 1 d . . . . .
N5 N 0.8701(4) 0.3851(4) 0.53504(7) 0.0323(9) Uani 1 1 d . . . . .
N6 N 0.7350(5) 0.8145(3) 0.52897(8) 0.0336(10) Uani 1 1 d . . . . .
C30 C 0.9469(6) 0.0082(4) 0.58467(9) 0.0343(12) Uani 1 1 d . . . . .
C31 C 0.8085(6) -0.0222(4) 0.59011(10) 0.0354(12) Uani 1 1 d . . . . .
H31 H 0.7884 -0.1077 0.5968 0.043 Uiso 1 1 calc R . . . .
C32 C 0.6987(5) 0.0657(5) 0.58634(10) 0.0367(12) Uani 1 1 d . . . . .
C33 C 0.7281(5) 0.1936(5) 0.57640(9) 0.0318(11) Uani 1 1 d . . . . .
H33 H 0.6558 0.2551 0.5733 0.038 Uiso 1 1 calc R . . . .
C34 C 0.8636(5) 0.2279(4) 0.57127(9) 0.0268(10) Uani 1 1 d . . . . .
C35 C 0.9713(5) 0.1377(4) 0.57556(9) 0.0284(10) Uani 1 1 d . . . . .
C36 C 1.0566(6) -0.0977(5) 0.58898(12) 0.0510(15) Uani 1 1 d . . . . .
H36A H 1.1172 -0.0698 0.6027 0.077 Uiso 1 1 calc GR . . . .
H36B H 1.1109 -0.1093 0.5737 0.077 Uiso 1 1 calc GR . . . .
H36C H 1.0122 -0.1822 0.5934 0.077 Uiso 1 1 calc GR . . . .
C37 C 0.5511(6) 0.0248(6) 0.59318(13) 0.0584(18) Uani 1 1 d . . . . .
H37A H 0.5059 -0.0138 0.5785 0.088 Uiso 1 1 calc GR . . . .
H37B H 0.4997 0.1033 0.5988 0.088 Uiso 1 1 calc GR . . . .
H37C H 0.5537 -0.0413 0.6067 0.088 Uiso 1 1 calc GR . . . .
C38 C 1.0809(5) 0.3224(4) 0.55814(10) 0.0336(11) Uani 1 1 d . . . . .
C39 C 0.9247(5) 0.3578(4) 0.56038(9) 0.0270(10) Uani 1 1 d . . . . .
C40 C 1.2387(5) 0.1420(5) 0.57164(11) 0.0466(14) Uani 1 1 d . . . . .
H40A H 1.2509 0.1139 0.5891 0.070 Uiso 1 1 calc GR . . . .
H40B H 1.3072 0.2102 0.5675 0.070 Uiso 1 1 calc GR . . . .
H40C H 1.2508 0.0652 0.5606 0.070 Uiso 1 1 calc GR . . . .
C41 C 0.8850(6) 0.2936(5) 0.51573(9) 0.0420(14) Uani 1 1 d . . . . .
H41 H 0.9490 0.2221 0.5153 0.050 Uiso 1 1 calc R . . . .
C42 C 0.7913(7) 0.3244(5) 0.49727(10) 0.0463(15) Uani 1 1 d . . . . .
H42 H 0.7795 0.2783 0.4819 0.056 Uiso 1 1 calc R . . . .
C43 C 0.7147(6) 0.4390(5) 0.50550(10) 0.0401(13) Uani 1 1 d . . . . .
H43 H 0.6429 0.4824 0.4966 0.048 Uiso 1 1 calc R . . . .
C44 C 0.7653(5) 0.4743(4) 0.52890(9) 0.0311(11) Uani 1 1 d . . . . .
C45 C 0.7338(5) 0.5923(4) 0.54560(9) 0.0299(11) Uani 1 1 d . . . . .
C46 C 0.7632(5) 0.5530(4) 0.57331(9) 0.0295(11) Uani 1 1 d . . . . .
H46A H 0.7581 0.6346 0.5837 0.035 Uiso 1 1 calc R . . . .
H46B H 0.6890 0.4926 0.5790 0.035 Uiso 1 1 calc R . . . .
C47 C 0.9035(5) 0.4844(4) 0.57838(9) 0.0278(10) Uani 1 1 d . . . . .
C48 C 0.9031(6) 0.4347(4) 0.60590(9) 0.0321(11) Uani 1 1 d . . . . .
C49 C 1.0446(6) 0.3621(5) 0.64021(10) 0.0435(13) Uani 1 1 d . . . . .
H49A H 0.9657 0.3944 0.6502 0.052 Uiso 1 1 calc R . . . .
H49B H 1.1303 0.3972 0.6478 0.052 Uiso 1 1 calc R . . . .
C50 C 1.0474(8) 0.2119(5) 0.64048(11) 0.065(2) Uani 1 1 d . . . . .
H50A H 1.1313 0.1804 0.6322 0.098 Uiso 1 1 calc GR . . . .
H50B H 0.9666 0.1774 0.6316 0.098 Uiso 1 1 calc GR . . . .
H50C H 1.0461 0.1802 0.6578 0.098 Uiso 1 1 calc GR . . . .
C51 C 0.8238(6) 0.7157(5) 0.53658(10) 0.0334(12) Uani 1 1 d . . . . .
C52 C 0.7807(6) 0.9461(4) 0.51985(11) 0.0456(15) Uani 1 1 d . . . . .
H52A H 0.7540 1.0148 0.5319 0.068 Uiso 1 1 calc GR . . . .
H52B H 0.7374 0.9647 0.5037 0.068 Uiso 1 1 calc GR . . . .
H52C H 0.8811 0.9460 0.5179 0.068 Uiso 1 1 calc GR . . . .
C53 C 0.5941(5) 0.7771(4) 0.53245(9) 0.0323(11) Uani 1 1 d . . . . .
C54 C 0.4761(6) 0.8524(5) 0.52760(10) 0.0412(13) Uani 1 1 d . . . . .
H54 H 0.4820 0.9397 0.5209 0.049 Uiso 1 1 calc R . . . .
C55 C 0.3485(6) 0.7937(5) 0.53307(10) 0.0437(14) Uani 1 1 d . . . . .
H55 H 0.2665 0.8429 0.5302 0.052 Uiso 1 1 calc R . . . .
C56 C 0.3396(6) 0.6633(5) 0.54269(10) 0.0436(14) Uani 1 1 d . . . . .
H56 H 0.2522 0.6257 0.5464 0.052 Uiso 1 1 calc R . . . .
C57 C 0.4610(6) 0.5885(5) 0.54685(10) 0.0399(13) Uani 1 1 d . . . . .
H57 H 0.4553 0.4996 0.5528 0.048 Uiso 1 1 calc R . . . .
C58 C 0.5888(5) 0.6457(4) 0.54212(9) 0.0304(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.219(5) . ?
O2 C18 1.420(5) . ?
O3 C19 1.199(6) . ?
O4 C19 1.336(6) . ?
O4 C20 1.461(6) . ?
O5 C22 1.229(6) . ?
N1 C6 1.417(5) . ?
N1 C9 1.368(6) . ?
N1 C11 1.460(6) . ?
N2 C10 1.465(6) . ?
N2 C12 1.378(6) . ?
N2 C15 1.399(6) . ?
N3 C22 1.352(7) . ?
N3 C23 1.466(7) . ?
N3 C24 1.408(7) . ?
C1 C2 1.405(6) . ?
C1 C6 1.393(7) . ?
C1 C7 1.507(7) . ?
C2 C3 1.393(7) . ?
C3 C4 1.396(7) . ?
C3 C8 1.517(6) . ?
C4 C5 1.389(6) . ?
C5 C6 1.392(7) . ?
C5 C10 1.516(6) . ?
C9 C10 1.550(6) . ?
C10 C18 1.571(6) . ?
C12 C13 1.363(7) . ?
C13 C14 1.431(7) . ?
C14 C15 1.354(7) . ?
C15 C16 1.500(7) . ?
C16 C17 1.549(7) . ?
C16 C22 1.564(7) . ?
C16 C29 1.534(6) . ?
C17 C18 1.540(6) . ?
C18 C19 1.533(7) . ?
C20 C21 1.496(8) . ?
C24 C25 1.375(7) . ?
C24 C29 1.395(7) . ?
C25 C26 1.390(8) . ?
C26 C27 1.403(8) . ?
C27 C28 1.402(7) . ?
C28 C29 1.372(7) . ?
O6 C38 1.206(6) . ?
O7 C47 1.404(5) . ?
O8 C48 1.203(6) . ?
O9 C48 1.335(6) . ?
O9 C49 1.463(6) . ?
O10 C51 1.225(6) . ?
N4 C35 1.421(6) . ?
N4 C38 1.371(6) . ?
N4 C40 1.454(6) . ?
N5 C39 1.465(6) . ?
N5 C41 1.376(6) . ?
N5 C44 1.381(6) . ?
N6 C51 1.361(6) . ?
N6 C52 1.462(6) . ?
N6 C53 1.417(6) . ?
C30 C31 1.395(7) . ?
C30 C35 1.395(6) . ?
C30 C36 1.507(7) . ?
C31 C32 1.385(7) . ?
C32 C33 1.405(7) . ?
C32 C37 1.519(7) . ?
C33 C34 1.374(7) . ?
C34 C35 1.387(6) . ?
C34 C39 1.531(6) . ?
C38 C39 1.547(7) . ?
C39 C47 1.592(6) . ?
C41 C42 1.364(8) . ?
C42 C43 1.425(7) . ?
C43 C44 1.376(7) . ?
C44 C45 1.499(6) . ?
C45 C46 1.544(7) . ?
C45 C51 1.575(6) . ?
C45 C58 1.504(7) . ?
C46 C47 1.535(6) . ?
C47 C48 1.538(7) . ?
C49 C50 1.493(7) . ?
C53 C54 1.382(7) . ?
C53 C58 1.404(6) . ?
C54 C55 1.389(8) . ?
C55 C56 1.395(7) . ?
C56 C57 1.402(7) . ?
C57 C58 1.376(7) . ?

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
C19 O4 C20 116.5(4) . . ?
C6 N1 C11 126.0(4) . . ?
C9 N1 C6 111.5(4) . . ?
C9 N1 C11 120.9(4) . . ?
C12 N2 C10 123.0(4) . . ?
C12 N2 C15 108.1(4) . . ?
C15 N2 C10 122.8(4) . . ?
C22 N3 C23 122.9(5) . . ?
C22 N3 C24 112.5(4) . . ?
C24 N3 C23 124.5(5) . . ?
C2 C1 C7 118.3(5) . . ?
C6 C1 C2 116.2(5) . . ?
C6 C1 C7 125.4(4) . . ?
C3 C2 C1 122.8(5) . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 C8 120.7(5) . . ?
C4 C3 C8 120.1(5) . . ?
C5 C4 C3 119.4(5) . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 C10 130.4(5) . . ?
C6 C5 C10 109.4(4) . . ?
C1 C6 N1 128.7(4) . . ?
C5 C6 N1 109.2(4) . . ?
C5 C6 C1 122.1(4) . . ?
O1 C9 N1 125.4(5) . . ?
O1 C9 C10 126.4(5) . . ?
N1 C9 C10 108.1(4) . . ?
N2 C10 C5 112.4(4) . . ?
N2 C10 C9 108.7(4) . . ?
N2 C10 C18 108.7(4) . . ?
C5 C10 C9 101.6(4) . . ?
C5 C10 C18 112.9(4) . . ?
C9 C10 C18 112.4(4) . . ?
C13 C12 N2 109.1(5) . . ?
C12 C13 C14 106.6(5) . . ?
C15 C14 C13 108.4(5) . . ?
N2 C15 C16 120.1(4) . . ?
C14 C15 N2 107.7(5) . . ?
C14 C15 C16 131.7(5) . . ?
C15 C16 C17 112.1(4) . . ?
C15 C16 C22 110.4(4) . . ?
C15 C16 C29 111.6(4) . . ?
C17 C16 C22 110.2(4) . . ?
C29 C16 C17 111.2(4) . . ?
C29 C16 C22 100.7(4) . . ?
C18 C17 C16 114.5(4) . . ?
O2 C18 C10 110.1(4) . . ?
O2 C18 C17 112.9(4) . . ?
O2 C18 C19 106.4(4) . . ?
C17 C18 C10 110.2(4) . . ?
C19 C18 C10 108.7(4) . . ?
C19 C18 C17 108.3(4) . . ?
O3 C19 O4 124.6(5) . . ?
O3 C19 C18 124.4(4) . . ?
O4 C19 C18 111.0(4) . . ?
O4 C20 C21 106.6(5) . . ?
O5 C22 N3 126.3(5) . . ?
O5 C22 C16 125.4(5) . . ?
N3 C22 C16 108.3(4) . . ?
C25 C24 N3 128.8(5) . . ?
C25 C24 C29 122.0(5) . . ?
C29 C24 N3 109.2(4) . . ?
C24 C25 C26 118.0(5) . . ?
C25 C26 C27 121.4(5) . . ?
C28 C27 C26 118.8(5) . . ?
C29 C28 C27 120.1(5) . . ?
C24 C29 C16 109.2(4) . . ?
C28 C29 C16 131.1(5) . . ?
C28 C29 C24 119.7(5) . . ?
C48 O9 C49 116.6(4) . . ?
C35 N4 C40 127.6(4) . . ?
C38 N4 C35 111.6(4) . . ?
C38 N4 C40 120.7(4) . . ?
C41 N5 C39 121.4(4) . . ?
C41 N5 C44 109.0(4) . . ?
C44 N5 C39 126.5(4) . . ?
C51 N6 C52 123.7(5) . . ?
C51 N6 C53 111.8(4) . . ?
C53 N6 C52 124.4(4) . . ?
C31 C30 C36 119.0(4) . . ?
C35 C30 C31 115.6(5) . . ?
C35 C30 C36 125.4(5) . . ?
C32 C31 C30 124.1(4) . . ?
C31 C32 C33 118.1(5) . . ?
C31 C32 C37 120.5(5) . . ?
C33 C32 C37 121.3(5) . . ?
C34 C33 C32 119.3(5) . . ?
C33 C34 C35 121.0(4) . . ?
C33 C34 C39 130.3(4) . . ?
C35 C34 C39 108.7(4) . . ?
C30 C35 N4 128.4(5) . . ?
C34 C35 N4 109.7(4) . . ?
C34 C35 C30 121.9(5) . . ?
O6 C38 N4 125.4(5) . . ?
O6 C38 C39 126.7(4) . . ?
N4 C38 C39 107.8(4) . . ?
N5 C39 C34 111.3(4) . . ?
N5 C39 C38 108.6(4) . . ?
N5 C39 C47 110.9(4) . . ?
C34 C39 C38 102.1(4) . . ?
C34 C39 C47 113.1(4) . . ?
C38 C39 C47 110.5(4) . . ?
C42 C41 N5 108.4(5) . . ?
C41 C42 C43 107.6(5) . . ?
C44 C43 C42 107.2(5) . . ?
N5 C44 C45 120.7(4) . . ?
C43 C44 N5 107.8(4) . . ?
C43 C44 C45 131.2(5) . . ?
C44 C45 C46 109.0(4) . . ?
C44 C45 C51 108.7(4) . . ?
C44 C45 C58 113.0(4) . . ?
C46 C45 C51 112.6(4) . . ?
C58 C45 C46 112.0(4) . . ?
C58 C45 C51 101.3(4) . . ?
C47 C46 C45 116.0(4) . . ?
O7 C47 C39 111.9(4) . . ?
O7 C47 C46 111.5(3) . . ?
O7 C47 C48 106.0(4) . . ?
C46 C47 C39 111.0(4) . . ?
C46 C47 C48 107.8(4) . . ?
C48 C47 C39 108.3(4) . . ?
O8 C48 O9 124.6(5) . . ?
O8 C48 C47 123.8(5) . . ?
O9 C48 C47 111.6(4) . . ?
O9 C49 C50 109.9(5) . . ?
O10 C51 N6 125.2(5) . . ?
O10 C51 C45 126.9(5) . . ?
N6 C51 C45 107.9(4) . . ?
C54 C53 N6 128.2(4) . . ?
C54 C53 C58 122.8(5) . . ?
C58 C53 N6 109.0(4) . . ?
C53 C54 C55 117.3(5) . . ?
C54 C55 C56 121.4(5) . . ?
C55 C56 C57 119.9(5) . . ?
C58 C57 C56 119.7(4) . . ?
C53 C58 C45 109.9(4) . . ?
C57 C58 C45 131.2(4) . . ?
C57 C58 C53 118.9(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O5 0.83 1.92 2.685(5) 152.5 .
O7 H7 O10 0.83 1.87 2.664(5) 158.7 .

_olex2_submission_special_instructions 'No special instructions were received'
