# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1941514'
loop_
_audit_author_name
_audit_author_address
'Brendan Twamley'
;TCD
Republic of Ireland
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

###original name tcd966

_audit_creation_date             2017-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H13 N3 O3'
_chemical_formula_sum            'C22 H13 N3 O3'
_chemical_formula_weight         367.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.2937(10)
_cell_length_b                   16.2786(15)
_cell_length_c                   9.2757(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.225(3)
_cell_angle_gamma                90
_cell_volume                     1660.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1647
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0644 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.9090. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1123
_diffrn_reflns_av_unetI/netI     0.1011
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10619
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.687
_diffrn_reflns_theta_min         3.114
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type            'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON 50'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1637
_reflns_number_total             3144
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      0.993
_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)+(0.0599P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C2 C 0.1238(3) 0.3461(2) -0.2102(4) 0.0312(9) Uani 1 1 d . . . . .
H2 H 0.049597 0.369433 -0.263625 0.037 Uiso 1 1 calc R . . . .
C3 C 0.1462(3) 0.2651(2) -0.2363(4) 0.0305(9) Uani 1 1 d . . . . .
H3 H 0.090593 0.234639 -0.309083 0.037 Uiso 1 1 calc R . . . .
C4 C 0.2497(3) 0.2292(2) -0.1555(4) 0.0266(9) Uani 1 1 d . . . . .
H4 H 0.267101 0.173121 -0.170485 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3293(3) 0.27644(19) -0.0509(4) 0.0204(8) Uani 1 1 d . . . . .
C6 C 0.4385(3) 0.2377(2) 0.0445(4) 0.0213(8) Uani 1 1 d . . . . .
C7 C 0.5154(3) 0.29065(19) 0.1601(4) 0.0205(8) Uani 1 1 d . . . . .
C8 C 0.4896(3) 0.37557(19) 0.1639(4) 0.0199(8) Uani 1 1 d . . . . .
C9 C 0.5681(3) 0.42493(19) 0.2683(4) 0.0209(8) Uani 1 1 d . . . . .
C10 C 0.5412(3) 0.50951(19) 0.2702(4) 0.0223(8) Uani 1 1 d . . . . .
H10 H 0.589946 0.545105 0.340729 0.027 Uiso 1 1 calc R . . . .
C11 C 0.4441(3) 0.5389(2) 0.1689(4) 0.0254(8) Uani 1 1 d . . . . .
H11 H 0.428699 0.596269 0.169439 0.031 Uiso 1 1 calc R . . . .
C13 C 0.3878(3) 0.41248(19) 0.0666(4) 0.0211(8) Uani 1 1 d . . . . .
C14 C 0.3026(3) 0.35955(19) -0.0359(4) 0.0206(8) Uani 1 1 d . . . . .
C17 C 0.6808(3) 0.30307(19) 0.3548(4) 0.0192(7) Uani 1 1 d . . . . .
C18 C 0.6686(3) 0.38687(19) 0.3678(4) 0.0200(8) Uani 1 1 d . . . . .
C19 C 0.7508(3) 0.43621(18) 0.4843(4) 0.0218(8) Uani 1 1 d . . . . .
C20 C 0.7575(3) 0.4196(2) 0.6329(4) 0.0246(8) Uani 1 1 d . . . . .
H20 H 0.712627 0.375218 0.660349 0.030 Uiso 1 1 calc R . . . .
C21 C 0.8295(3) 0.4677(2) 0.7400(4) 0.0288(9) Uani 1 1 d . . . . .
H21 H 0.834076 0.456547 0.841680 0.035 Uiso 1 1 calc R . . . .
C22 C 0.8955(3) 0.5324(2) 0.7004(4) 0.0287(9) Uani 1 1 d . . . . .
H22 H 0.945160 0.565361 0.774912 0.034 Uiso 1 1 calc R . . . .
C23 C 0.8891(3) 0.5489(2) 0.5534(4) 0.0294(9) Uani 1 1 d . . . . .
H23 H 0.934401 0.593195 0.526428 0.035 Uiso 1 1 calc R . . . .
C24 C 0.8167(3) 0.50116(19) 0.4452(4) 0.0253(8) Uani 1 1 d . . . . .
H24 H 0.811878 0.512782 0.343627 0.030 Uiso 1 1 calc R . . . .
C25 C 0.7858(3) 0.2577(2) 0.4515(4) 0.0224(8) Uani 1 1 d . . . . .
C28 C 0.8445(3) 0.1378(2) 0.5913(4) 0.0269(9) Uani 1 1 d . . . . .
H28A H 0.912872 0.133693 0.543012 0.040 Uiso 1 1 calc GR . . . .
H28B H 0.813027 0.082770 0.603374 0.040 Uiso 1 1 calc GR . . . .
H28C H 0.872002 0.163633 0.688659 0.040 Uiso 1 1 calc GR . . . .
N1 N 0.1997(3) 0.39433(17) -0.1146(3) 0.0287(8) Uani 1 1 d . . . . .
N12 N 0.3673(2) 0.49242(16) 0.0670(3) 0.0250(7) Uani 1 1 d . . . . .
N16 N 0.6061(2) 0.25476(16) 0.2540(3) 0.0208(7) Uani 1 1 d . . . . .
O15 O 0.4637(2) 0.16568(13) 0.0293(3) 0.0261(6) Uani 1 1 d . . . . .
O26 O 0.8899(2) 0.28062(14) 0.4771(3) 0.0317(7) Uani 1 1 d . . . . .
O27 O 0.7491(2) 0.18720(13) 0.5009(3) 0.0252(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
C2 H2 0.9500 . ?
C2 C3 1.374(5) . ?
C2 N1 1.337(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.368(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(5) . ?
C5 C6 1.484(4) . ?
C5 C14 1.400(4) . ?
C6 C7 1.490(5) . ?
C6 O15 1.222(4) . ?
C7 C8 1.415(4) . ?
C7 N16 1.319(4) . ?
C8 C9 1.406(4) . ?
C8 C13 1.422(4) . ?
C9 C10 1.411(4) . ?
C9 C18 1.429(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.357(4) . ?
C11 H11 0.9500 . ?
C11 N12 1.358(4) . ?
C13 C14 1.467(4) . ?
C13 N12 1.322(4) . ?
C14 N1 1.347(4) . ?
C17 C18 1.379(4) . ?
C17 C25 1.507(4) . ?
C17 N16 1.358(4) . ?
C18 C19 1.489(4) . ?
C19 C20 1.390(5) . ?
C19 C24 1.387(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.375(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(5) . ?
C24 H24 0.9500 . ?
C25 O26 1.203(4) . ?
C25 O27 1.336(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 O27 1.447(4) . ?

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
C3 C2 H2 117.8 . . ?
N1 C2 H2 117.8 . . ?
N1 C2 C3 124.4(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 C14 118.9(3) . . ?
C14 C5 C6 121.3(3) . . ?
C5 C6 C7 116.8(3) . . ?
O15 C6 C5 121.5(3) . . ?
O15 C6 C7 121.7(3) . . ?
C8 C7 C6 119.6(3) . . ?
N16 C7 C6 117.1(3) . . ?
N16 C7 C8 123.3(3) . . ?
C7 C8 C13 122.6(3) . . ?
C9 C8 C7 118.3(3) . . ?
C9 C8 C13 119.1(3) . . ?
C8 C9 C10 117.5(3) . . ?
C8 C9 C18 118.7(3) . . ?
C10 C9 C18 123.8(3) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.6(3) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 117.6 . . ?
C10 C11 N12 124.9(3) . . ?
N12 C11 H11 117.6 . . ?
C8 C13 C14 118.6(3) . . ?
N12 C13 C8 122.1(3) . . ?
N12 C13 C14 119.4(3) . . ?
C5 C14 C13 120.5(3) . . ?
N1 C14 C5 122.1(3) . . ?
N1 C14 C13 117.4(3) . . ?
C18 C17 C25 120.9(3) . . ?
N16 C17 C18 125.1(3) . . ?
N16 C17 C25 114.0(3) . . ?
C9 C18 C19 120.4(3) . . ?
C17 C18 C9 116.9(3) . . ?
C17 C18 C19 122.6(3) . . ?
C20 C19 C18 119.9(3) . . ?
C24 C19 C18 120.3(3) . . ?
C24 C19 C20 119.8(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
O26 C25 C17 124.5(3) . . ?
O26 C25 O27 124.3(3) . . ?
O27 C25 C17 111.2(3) . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O27 C28 H28A 109.5 . . ?
O27 C28 H28B 109.5 . . ?
O27 C28 H28C 109.5 . . ?
C2 N1 C14 117.0(3) . . ?
C13 N12 C11 117.8(3) . . ?
C7 N16 C17 117.7(3) . . ?
C25 O27 C28 115.3(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O15 0.95 2.45 3.158(4) 131.1 2_655

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
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C2 N1 C14 -2.2(6) . . . . ?
C3 C4 C5 C6 176.3(3) . . . . ?
C3 C4 C5 C14 -2.3(5) . . . . ?
C4 C5 C6 C7 -176.3(3) . . . . ?
C4 C5 C6 O15 3.3(5) . . . . ?
C4 C5 C14 C13 -176.3(3) . . . . ?
C4 C5 C14 N1 3.1(5) . . . . ?
C5 C6 C7 C8 -6.7(5) . . . . ?
C5 C6 C7 N16 173.9(3) . . . . ?
C5 C14 N1 C2 -0.9(5) . . . . ?
C6 C5 C14 C13 5.2(5) . . . . ?
C6 C5 C14 N1 -175.4(3) . . . . ?
C6 C7 C8 C9 -176.1(3) . . . . ?
C6 C7 C8 C13 4.0(5) . . . . ?
C6 C7 N16 C17 176.5(3) . . . . ?
C7 C8 C9 C10 179.9(3) . . . . ?
C7 C8 C9 C18 -1.3(5) . . . . ?
C7 C8 C13 C14 3.5(5) . . . . ?
C7 C8 C13 N12 -177.2(3) . . . . ?
C8 C7 N16 C17 -2.8(5) . . . . ?
C8 C9 C10 C11 -2.1(5) . . . . ?
C8 C9 C18 C17 -0.5(5) . . . . ?
C8 C9 C18 C19 -177.4(3) . . . . ?
C8 C13 C14 C5 -8.1(5) . . . . ?
C8 C13 C14 N1 172.4(3) . . . . ?
C8 C13 N12 C11 -2.9(5) . . . . ?
C9 C8 C13 C14 -176.5(3) . . . . ?
C9 C8 C13 N12 2.8(5) . . . . ?
C9 C10 C11 N12 2.1(5) . . . . ?
C9 C18 C19 C20 116.0(4) . . . . ?
C9 C18 C19 C24 -61.0(4) . . . . ?
C10 C9 C18 C17 178.2(3) . . . . ?
C10 C9 C18 C19 1.3(5) . . . . ?
C10 C11 N12 C13 0.5(5) . . . . ?
C13 C8 C9 C10 -0.2(5) . . . . ?
C13 C8 C9 C18 178.6(3) . . . . ?
C13 C14 N1 C2 178.5(3) . . . . ?
C14 C5 C6 C7 2.2(5) . . . . ?
C14 C5 C6 O15 -178.2(3) . . . . ?
C14 C13 N12 C11 176.3(3) . . . . ?
C17 C18 C19 C20 -60.7(5) . . . . ?
C17 C18 C19 C24 122.3(4) . . . . ?
C17 C25 O27 C28 178.1(3) . . . . ?
C18 C9 C10 C11 179.2(3) . . . . ?
C18 C17 C25 O26 -44.9(5) . . . . ?
C18 C17 C25 O27 137.4(3) . . . . ?
C18 C17 N16 C7 0.7(5) . . . . ?
C18 C19 C20 C21 -177.1(3) . . . . ?
C18 C19 C24 C23 177.3(3) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C19 C24 C23 0.3(5) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C19 -0.4(5) . . . . ?
C24 C19 C20 C21 -0.1(5) . . . . ?
C25 C17 C18 C9 178.2(3) . . . . ?
C25 C17 C18 C19 -5.1(5) . . . . ?
C25 C17 N16 C7 -176.7(3) . . . . ?
N1 C2 C3 C4 3.1(6) . . . . ?
N12 C13 C14 C5 172.6(3) . . . . ?
N12 C13 C14 N1 -6.9(5) . . . . ?
N16 C7 C8 C9 3.2(5) . . . . ?
N16 C7 C8 C13 -176.7(3) . . . . ?
N16 C17 C18 C9 0.9(5) . . . . ?
N16 C17 C18 C19 177.7(3) . . . . ?
N16 C17 C25 O26 132.6(4) . . . . ?
N16 C17 C25 O27 -45.1(4) . . . . ?
O15 C6 C7 C8 173.7(3) . . . . ?
O15 C6 C7 N16 -5.7(5) . . . . ?
O26 C25 O27 C28 0.4(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_original_sample_id MA3:21B
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1941515'
loop_
_audit_author_name
_audit_author_address
'Brendan Twamley'
;TCD
Republic of Ireland
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

####original name tcd1297

_audit_creation_date             2019-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H17 Br N3 O6 Re'
_chemical_formula_sum            'C27 H17 Br N3 O6 Re'
_chemical_formula_weight         745.54
_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'
Br Br -0.6763 1.2805 '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'
Re Re -5.2083 5.8923 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5421(3)
_cell_length_b                   10.0776(4)
_cell_length_c                   15.2032(6)
_cell_angle_alpha                83.1740(16)
_cell_angle_beta                 74.5305(15)
_cell_angle_gamma                78.6214(16)
_cell_volume                     1233.50(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.622
_cell_measurement_theta_min      3.0235
_shelx_estimated_absorpt_T_max   0.715
_shelx_estimated_absorpt_T_min   0.305
_exptl_absorpt_coefficient_mu    11.963
_exptl_absorpt_correction_T_max  0.9042
_exptl_absorpt_correction_T_min  0.4049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.007
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17848
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.537
_diffrn_reflns_theta_min         3.023
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 Kappa Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       APEX2
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4369
_reflns_number_total             4591
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         2.352
_refine_diff_density_min         -1.822
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4591
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+1.2791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          
'Br1 and trans CO groups (C33, O34) disordered and modelled in two positions with 95:5% occupancy with restraints (DFIX, SADI, SIMU).'
_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
2. Restrained distances
 C25-C10
 1.48 with sigma of 0.01
 Re1-C33 = Re1-C33A
 1.95 with sigma of 0.01
 O34-C33 = O34A-C33A
 1.15 with sigma of 0.01
 Re1-Br1A \\sim Re1-Br1
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Br1 \\sim Br1A \\sim O34 \\sim O34A \\sim C33 \\sim C33A: within 2A with sigma
of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: Br1(0.95) Br1A(0.05) O34(0.95) O34A(0.05) C33(0.95) C33A(0.05)
5.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
5.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Re1 Re 0.81788(2) 0.63714(2) 0.30302(2) 0.01557(10) Uani 1 1 d D . . . .
Br1 Br 0.71915(7) 0.42462(6) 0.40009(4) 0.02331(15) Uani 0.95 1 d D U P A 1
Br1A Br 0.911(2) 0.8583(11) 0.2187(12) 0.030(3) Uani 0.05 1 d D U P A 2
O7 O 0.1529(4) 0.9743(3) 0.5724(2) 0.0207(7) Uani 1 1 d . . . . .
O26 O 0.4463(5) 1.0477(4) 0.8518(2) 0.0288(8) Uani 1 1 d . . . . .
O27 O 0.3025(4) 0.8745(3) 0.8868(2) 0.0194(7) Uani 1 1 d . . . . .
O32 O 1.1880(4) 0.5195(4) 0.2767(2) 0.0244(7) Uani 1 1 d . . . . .
O34 O 0.9391(7) 0.8820(5) 0.1831(3) 0.0316(11) Uani 0.95 1 d D U P A 1
O34A O 0.741(9) 0.358(5) 0.394(5) 0.021(5) Uani 0.05 1 d D U P A 2
O36 O 0.8022(6) 0.5285(5) 0.1256(3) 0.0430(11) Uani 1 1 d . . . . .
N1 N 0.5580(4) 0.7313(4) 0.3392(3) 0.0154(8) Uani 1 1 d . . . . .
N9 N 0.3641(5) 0.9197(4) 0.6861(3) 0.0180(8) Uani 1 1 d . . . . .
N15 N 0.7787(5) 0.7120(4) 0.4361(2) 0.0140(7) Uani 1 1 d . . . . .
C2 C 0.4493(6) 0.7419(5) 0.2879(3) 0.0195(9) Uani 1 1 d . . . . .
H2 H 0.484822 0.703628 0.230221 0.023 Uiso 1 1 calc R . . . .
C3 C 0.2880(6) 0.8064(5) 0.3161(3) 0.0207(10) Uani 1 1 d . . . . .
H3 H 0.214727 0.811691 0.278067 0.025 Uiso 1 1 calc R . . . .
C4 C 0.2326(5) 0.8634(5) 0.3997(3) 0.0166(9) Uani 1 1 d . . . . .
H4 H 0.122010 0.908753 0.419596 0.020 Uiso 1 1 calc R . . . .
C5 C 0.3435(6) 0.8525(5) 0.4541(3) 0.0165(9) Uani 1 1 d . . . . .
C6 C 0.2885(5) 0.9088(5) 0.5460(3) 0.0177(9) Uani 1 1 d . . . . .
C8 C 0.4138(6) 0.8809(5) 0.6027(3) 0.0167(9) Uani 1 1 d . . . . .
C10 C 0.4743(6) 0.8942(5) 0.7377(3) 0.0169(9) Uani 1 1 d D . . . .
C11 C 0.6385(5) 0.8303(5) 0.7101(3) 0.0163(9) Uani 1 1 d . . . . .
C12 C 0.6936(5) 0.7918(4) 0.6182(3) 0.0146(8) Uani 1 1 d . . . . .
C13 C 0.8553(6) 0.7298(5) 0.5761(3) 0.0175(9) Uani 1 1 d . . . . .
H13 H 0.938545 0.714105 0.608718 0.021 Uiso 1 1 calc R . . . .
C14 C 0.8923(6) 0.6922(5) 0.4879(3) 0.0171(9) Uani 1 1 d . . . . .
H14 H 1.002043 0.650415 0.461296 0.021 Uiso 1 1 calc R . . . .
C16 C 0.6258(5) 0.7712(4) 0.4753(3) 0.0151(9) Uani 1 1 d . . . . .
C17 C 0.5042(5) 0.7862(5) 0.4211(3) 0.0145(8) Uani 1 1 d . . . . .
C18 C 0.5768(5) 0.8154(5) 0.5644(3) 0.0153(9) Uani 1 1 d . . . . .
C19 C 0.7432(6) 0.7980(5) 0.7758(3) 0.0181(9) Uani 1 1 d . . . . .
C20 C 0.8940(6) 0.8417(5) 0.7595(3) 0.0210(10) Uani 1 1 d . . . . .
H20 H 0.933167 0.894081 0.704670 0.025 Uiso 1 1 calc R . . . .
C21 C 0.9863(7) 0.8084(6) 0.8235(4) 0.0292(11) Uani 1 1 d . . . . .
H21 H 1.089082 0.838260 0.812245 0.035 Uiso 1 1 calc R . . . .
C22 C 0.9311(7) 0.7321(6) 0.9038(4) 0.0290(12) Uani 1 1 d . . . . .
H22 H 0.995259 0.710299 0.947509 0.035 Uiso 1 1 calc R . . . .
C23 C 0.7811(7) 0.6875(6) 0.9202(3) 0.0268(11) Uani 1 1 d . . . . .
H23 H 0.742233 0.635501 0.975312 0.032 Uiso 1 1 calc R . . . .
C24 C 0.6885(6) 0.7192(5) 0.8560(3) 0.0231(10) Uani 1 1 d . . . . .
H24 H 0.587305 0.687040 0.866546 0.028 Uiso 1 1 calc R . . . .
C25 C 0.4080(5) 0.9481(5) 0.8321(3) 0.0175(9) Uani 1 1 d D . . . .
C28 C 0.2295(6) 0.9187(6) 0.9796(3) 0.0269(11) Uani 1 1 d . . . . .
H28A H 0.112478 0.907184 0.999175 0.032 Uiso 1 1 calc R . . . .
H28B H 0.233653 1.016054 0.980273 0.032 Uiso 1 1 calc R . . . .
C29 C 0.3229(7) 0.8361(7) 1.0447(4) 0.0345(13) Uani 1 1 d . . . . .
H29A H 0.279327 0.872823 1.105741 0.041 Uiso 1 1 calc R . . . .
H29B H 0.440397 0.845717 1.023082 0.041 Uiso 1 1 calc R . . . .
C30 C 0.3110(9) 0.6870(7) 1.0537(4) 0.0463(16) Uani 1 1 d . . . . .
H30A H 0.356447 0.649260 0.993827 0.069 Uiso 1 1 calc GR . . . .
H30B H 0.195151 0.676414 1.076459 0.069 Uiso 1 1 calc GR . . . .
H30C H 0.373699 0.638740 1.096796 0.069 Uiso 1 1 calc GR . . . .
C31 C 1.0488(7) 0.5596(5) 0.2858(3) 0.0218(10) Uani 1 1 d . . . . .
C33 C 0.8895(7) 0.7970(5) 0.2301(4) 0.0205(12) Uani 0.95 1 d D U P A 1
C33A C 0.770(12) 0.459(5) 0.355(7) 0.022(5) Uani 0.05 1 d D U P A 2
C35 C 0.8128(7) 0.5679(5) 0.1913(3) 0.0252(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
Re1 Br1 2.6026(6) . ?
Re1 Br1A 2.594(5) . ?
Re1 N1 2.184(4) . ?
Re1 N15 2.162(4) . ?
Re1 C31 1.933(5) . ?
Re1 C33 1.950(5) . ?
Re1 C33A 1.952(10) . ?
Re1 C35 1.925(5) . ?
O7 C6 1.205(6) . ?
O26 C25 1.207(6) . ?
O27 C25 1.331(6) . ?
O27 C28 1.466(5) . ?
O32 C31 1.153(6) . ?
O34 C33 1.122(6) . ?
O34A C33A 1.152(10) . ?
O36 C35 1.150(7) . ?
N1 C2 1.345(6) . ?
N1 C17 1.351(6) . ?
N9 C8 1.306(6) . ?
N9 C10 1.349(6) . ?
N15 C14 1.377(6) . ?
N15 C16 1.334(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(6) . ?
C5 C6 1.492(6) . ?
C5 C17 1.390(6) . ?
C6 C8 1.512(6) . ?
C8 C18 1.418(6) . ?
C10 C11 1.397(6) . ?
C10 C25 1.518(5) . ?
C11 C12 1.425(6) . ?
C11 C19 1.480(6) . ?
C12 C13 1.410(6) . ?
C12 C18 1.420(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(6) . ?
C14 H14 0.9500 . ?
C16 C17 1.465(6) . ?
C16 C18 1.406(6) . ?
C19 C20 1.394(7) . ?
C19 C24 1.395(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(8) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(7) . ?
C24 H24 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.508(8) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.514(9) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
N1 Re1 Br1 85.35(10) . . ?
N1 Re1 Br1A 93.2(4) . . ?
N15 Re1 Br1 82.88(10) . . ?
N15 Re1 Br1A 92.5(4) . . ?
N15 Re1 N1 75.17(14) . . ?
C31 Re1 Br1 93.58(14) . . ?
C31 Re1 Br1A 87.3(4) . . ?
C31 Re1 N1 172.84(16) . . ?
C31 Re1 N15 97.67(17) . . ?
C31 Re1 C33 87.0(2) . . ?
C31 Re1 C33A 87(3) . . ?
C33 Re1 Br1 179.39(19) . . ?
C33 Re1 N1 94.1(2) . . ?
C33 Re1 N15 97.2(2) . . ?
C33A Re1 Br1A 173(3) . . ?
C33A Re1 N1 93(3) . . ?
C33A Re1 N15 93(3) . . ?
C35 Re1 Br1 91.90(16) . . ?
C35 Re1 Br1A 92.7(5) . . ?
C35 Re1 N1 96.02(19) . . ?
C35 Re1 N15 170.04(19) . . ?
C35 Re1 C31 91.1(2) . . ?
C35 Re1 C33 87.9(2) . . ?
C35 Re1 C33A 83(3) . . ?
C25 O27 C28 116.1(4) . . ?
C2 N1 Re1 126.8(3) . . ?
C2 N1 C17 117.6(4) . . ?
C17 N1 Re1 115.6(3) . . ?
C8 N9 C10 117.6(4) . . ?
C14 N15 Re1 126.0(3) . . ?
C16 N15 Re1 116.7(3) . . ?
C16 N15 C14 116.9(4) . . ?
N1 C2 H2 118.8 . . ?
N1 C2 C3 122.3(4) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.2(4) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 120.3(4) . . ?
C17 C5 C4 118.3(4) . . ?
C17 C5 C6 121.4(4) . . ?
O7 C6 C5 121.6(4) . . ?
O7 C6 C8 122.3(4) . . ?
C5 C6 C8 116.1(4) . . ?
N9 C8 C6 117.0(4) . . ?
N9 C8 C18 123.3(4) . . ?
C18 C8 C6 119.7(4) . . ?
N9 C10 C11 126.0(4) . . ?
N9 C10 C25 114.0(4) . . ?
C11 C10 C25 120.0(4) . . ?
C10 C11 C12 116.3(4) . . ?
C10 C11 C19 120.6(4) . . ?
C12 C11 C19 123.0(4) . . ?
C13 C12 C11 125.3(4) . . ?
C13 C12 C18 116.8(4) . . ?
C18 C12 C11 117.9(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
N15 C14 H14 118.3 . . ?
C13 C14 N15 123.4(4) . . ?
C13 C14 H14 118.3 . . ?
N15 C16 C17 116.4(4) . . ?
N15 C16 C18 123.8(4) . . ?
C18 C16 C17 119.7(4) . . ?
N1 C17 C5 123.3(4) . . ?
N1 C17 C16 116.0(4) . . ?
C5 C17 C16 120.8(4) . . ?
C8 C18 C12 119.0(4) . . ?
C16 C18 C8 122.1(4) . . ?
C16 C18 C12 118.9(4) . . ?
C20 C19 C11 122.3(4) . . ?
C20 C19 C24 119.5(4) . . ?
C24 C19 C11 118.1(4) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.7(5) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.9(5) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.7(5) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(5) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.4(5) . . ?
C23 C24 H24 119.8 . . ?
O26 C25 O27 126.0(4) . . ?
O26 C25 C10 122.4(4) . . ?
O27 C25 C10 111.6(4) . . ?
O27 C28 H28A 109.7 . . ?
O27 C28 H28B 109.7 . . ?
O27 C28 C29 109.8(4) . . ?
H28A C28 H28B 108.2 . . ?
C29 C28 H28A 109.7 . . ?
C29 C28 H28B 109.7 . . ?
C28 C29 H29A 108.9 . . ?
C28 C29 H29B 108.9 . . ?
C28 C29 C30 113.2(5) . . ?
H29A C29 H29B 107.8 . . ?
C30 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O32 C31 Re1 176.5(4) . . ?
O34 C33 Re1 174.3(5) . . ?
O34A C33A Re1 174(10) . . ?
O36 C35 Re1 176.9(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
_geom_hbond_publ_flag
C4 H4 O7 0.95 2.39 3.315(5) 165 2_576 yes
C21 H21 O27 0.95 2.49 3.304(6) 144 1_655 yes
C23 H23 O36 0.95 2.54 3.368(6) 145 1_556 yes

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
Re1 N1 C2 C3 -178.4(3) . . . . ?
Re1 N1 C17 C5 178.7(3) . . . . ?
Re1 N1 C17 C16 -1.8(5) . . . . ?
Re1 N15 C14 C13 -172.9(3) . . . . ?
Re1 N15 C16 C17 -3.7(5) . . . . ?
Re1 N15 C16 C18 174.7(3) . . . . ?
O7 C6 C8 N9 6.5(7) . . . . ?
O7 C6 C8 C18 -173.4(4) . . . . ?
O27 C28 C29 C30 -64.1(6) . . . . ?
N1 C2 C3 C4 0.1(7) . . . . ?
N9 C8 C18 C12 -0.8(7) . . . . ?
N9 C8 C18 C16 178.2(4) . . . . ?
N9 C10 C11 C12 1.5(7) . . . . ?
N9 C10 C11 C19 -174.9(4) . . . . ?
N9 C10 C25 O26 -105.1(5) . . . . ?
N9 C10 C25 O27 73.2(5) . . . . ?
N15 C16 C17 N1 3.6(6) . . . . ?
N15 C16 C17 C5 -176.8(4) . . . . ?
N15 C16 C18 C8 178.5(4) . . . . ?
N15 C16 C18 C12 -2.6(7) . . . . ?
C2 N1 C17 C5 -0.1(7) . . . . ?
C2 N1 C17 C16 179.4(4) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 C6 -178.2(4) . . . . ?
C3 C4 C5 C17 0.6(7) . . . . ?
C4 C5 C6 O7 -6.3(7) . . . . ?
C4 C5 C6 C8 174.8(4) . . . . ?
C4 C5 C17 N1 -0.3(7) . . . . ?
C4 C5 C17 C16 -179.8(4) . . . . ?
C5 C6 C8 N9 -174.7(4) . . . . ?
C5 C6 C8 C18 5.5(6) . . . . ?
C6 C5 C17 N1 178.6(4) . . . . ?
C6 C5 C17 C16 -0.9(7) . . . . ?
C6 C8 C18 C12 179.1(4) . . . . ?
C6 C8 C18 C16 -2.0(7) . . . . ?
C8 N9 C10 C11 0.4(7) . . . . ?
C8 N9 C10 C25 177.5(4) . . . . ?
C10 N9 C8 C6 179.4(4) . . . . ?
C10 N9 C8 C18 -0.8(7) . . . . ?
C10 C11 C12 C13 178.1(4) . . . . ?
C10 C11 C12 C18 -2.9(6) . . . . ?
C10 C11 C19 C20 -125.1(5) . . . . ?
C10 C11 C19 C24 55.9(6) . . . . ?
C11 C10 C25 O26 72.2(6) . . . . ?
C11 C10 C25 O27 -109.5(5) . . . . ?
C11 C12 C13 C14 177.3(4) . . . . ?
C11 C12 C18 C8 2.6(6) . . . . ?
C11 C12 C18 C16 -176.3(4) . . . . ?
C11 C19 C20 C21 180.0(5) . . . . ?
C11 C19 C24 C23 -179.2(5) . . . . ?
C12 C11 C19 C20 58.8(7) . . . . ?
C12 C11 C19 C24 -120.2(5) . . . . ?
C12 C13 C14 N15 0.2(7) . . . . ?
C13 C12 C18 C8 -178.3(4) . . . . ?
C13 C12 C18 C16 2.7(6) . . . . ?
C14 N15 C16 C17 -177.3(4) . . . . ?
C14 N15 C16 C18 1.1(6) . . . . ?
C16 N15 C14 C13 0.1(7) . . . . ?
C17 N1 C2 C3 0.2(7) . . . . ?
C17 C5 C6 O7 174.9(4) . . . . ?
C17 C5 C6 C8 -4.0(6) . . . . ?
C17 C16 C18 C8 -3.2(6) . . . . ?
C17 C16 C18 C12 175.8(4) . . . . ?
C18 C12 C13 C14 -1.7(7) . . . . ?
C18 C16 C17 N1 -174.8(4) . . . . ?
C18 C16 C17 C5 4.7(6) . . . . ?
C19 C11 C12 C13 -5.6(7) . . . . ?
C19 C11 C12 C18 173.4(4) . . . . ?
C19 C20 C21 C22 0.0(8) . . . . ?
C20 C19 C24 C23 1.8(7) . . . . ?
C20 C21 C22 C23 0.4(8) . . . . ?
C21 C22 C23 C24 0.3(8) . . . . ?
C22 C23 C24 C19 -1.4(8) . . . . ?
C24 C19 C20 C21 -1.1(7) . . . . ?
C25 O27 C28 C29 -97.6(5) . . . . ?
C25 C10 C11 C12 -175.5(4) . . . . ?
C25 C10 C11 C19 8.2(7) . . . . ?
C28 O27 C25 O26 -1.1(7) . . . . ?
C28 O27 C25 C10 -179.3(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_original_sample_id JCRe1
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1941516'
loop_
_audit_author_name
_audit_author_address
'Brendan Twamley'
;TCD
Republic of Ireland
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

#####original name tcd1209

_audit_creation_date             2019-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 N3 O3'
_chemical_formula_sum            'C24 H19 N3 O3'
_chemical_formula_weight         397.42
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3727(5)
_cell_length_b                   9.5629(5)
_cell_length_c                   10.6715(5)
_cell_angle_alpha                85.613(4)
_cell_angle_beta                 89.352(4)
_cell_angle_gamma                78.428(4)
_cell_volume                     934.29(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      4.16
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0799 before and 0.0609 after correction. The Ratio of minimum to maximum transmission is 0.8525. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11713
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.718
_diffrn_reflns_theta_min         4.155
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 Kappa Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       APEX2
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2078
_reflns_number_total             3423
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      0.994
_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)+(0.0896P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1743
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O10 O 0.3922(2) 0.1631(2) 0.47854(18) 0.0334(5) Uani 1 1 d . . . . .
O26 O 0.7065(2) 0.1561(2) 0.19665(19) 0.0360(5) Uani 1 1 d . . . . .
O27 O 0.6423(2) 0.3965(2) 0.15943(19) 0.0354(5) Uani 1 1 d . . . . .
N1 N 0.0931(3) 0.6938(3) 0.6060(2) 0.0354(6) Uani 1 1 d . . . . .
N7 N 0.4550(3) 0.4100(3) 0.3453(2) 0.0316(6) Uani 1 1 d . . . . .
N16 N 0.0249(3) 0.4483(3) 0.7186(2) 0.0373(6) Uani 1 1 d . . . . .
C2 C 0.1256(4) 0.8109(3) 0.5486(3) 0.0394(7) Uani 1 1 d . . . . .
H2 H 0.075317 0.900590 0.574030 0.047 Uiso 1 1 calc R . . . .
C3 C 0.2284(4) 0.8116(3) 0.4534(3) 0.0376(7) Uani 1 1 d . . . . .
H3 H 0.247555 0.899399 0.416157 0.045 Uiso 1 1 calc R . . . .
C4 C 0.3015(3) 0.6834(3) 0.4143(3) 0.0346(7) Uani 1 1 d . . . . .
H4 H 0.370923 0.680865 0.348586 0.042 Uiso 1 1 calc R . . . .
C5 C 0.2719(3) 0.5559(3) 0.4732(3) 0.0314(6) Uani 1 1 d . . . . .
C6 C 0.3464(3) 0.4174(3) 0.4385(3) 0.0306(6) Uani 1 1 d . . . . .
C8 C 0.5080(3) 0.2867(3) 0.3103(3) 0.0310(6) Uani 1 1 d . . . . .
C9 C 0.4622(3) 0.1479(3) 0.3562(3) 0.0317(6) Uani 1 1 d . . . . .
H9 H 0.552153 0.071531 0.366938 0.038 Uiso 1 1 calc R . . . .
C11 C 0.3179(3) 0.2967(3) 0.5017(3) 0.0315(6) Uani 1 1 d . . . . .
C12 C 0.2109(3) 0.3016(3) 0.5993(3) 0.0306(6) Uani 1 1 d . . . . .
C13 C 0.1781(3) 0.1770(3) 0.6609(3) 0.0337(7) Uani 1 1 d . . . . .
H13 H 0.230739 0.085290 0.642362 0.040 Uiso 1 1 calc R . . . .
C14 C 0.0692(4) 0.1899(3) 0.7479(3) 0.0381(7) Uani 1 1 d . . . . .
H14 H 0.043927 0.107570 0.790766 0.046 Uiso 1 1 calc R . . . .
C15 C -0.0037(4) 0.3263(3) 0.7719(3) 0.0389(7) Uani 1 1 d . . . . .
H15 H -0.080440 0.333430 0.831458 0.047 Uiso 1 1 calc R . . . .
C17 C 0.1329(3) 0.4356(3) 0.6322(3) 0.0314(6) Uani 1 1 d . . . . .
C18 C 0.1659(3) 0.5666(3) 0.5692(3) 0.0311(6) Uani 1 1 d . . . . .
C19 C 0.3642(3) 0.1017(3) 0.2624(3) 0.0313(6) Uani 1 1 d . . . . .
C20 C 0.4233(3) -0.0085(3) 0.1864(3) 0.0336(7) Uani 1 1 d . . . . .
H20 H 0.522678 -0.054663 0.195883 0.040 Uiso 1 1 calc R . . . .
C21 C 0.3370(4) -0.0501(3) 0.0974(3) 0.0375(7) Uani 1 1 d . . . . .
H21 H 0.377921 -0.122958 0.044188 0.045 Uiso 1 1 calc R . . . .
C22 C 0.1908(4) 0.0143(3) 0.0857(3) 0.0360(7) Uani 1 1 d . . . . .
H22 H 0.131543 -0.015211 0.025336 0.043 Uiso 1 1 calc R . . . .
C23 C 0.1313(3) 0.1217(3) 0.1622(3) 0.0362(7) Uani 1 1 d . . . . .
H23 H 0.030915 0.164945 0.154847 0.043 Uiso 1 1 calc R . . . .
C24 C 0.2178(3) 0.1663(3) 0.2496(3) 0.0341(7) Uani 1 1 d . . . . .
H24 H 0.177007 0.241158 0.300855 0.041 Uiso 1 1 calc R . . . .
C25 C 0.6318(3) 0.2707(3) 0.2163(3) 0.0313(6) Uani 1 1 d . . . . .
C28 C 0.7636(3) 0.4014(3) 0.0729(3) 0.0355(7) Uani 1 1 d . . . . .
H28A H 0.785415 0.313469 0.027038 0.043 Uiso 1 1 calc R . . . .
H28B H 0.851998 0.409232 0.119594 0.043 Uiso 1 1 calc R . . . .
C29 C 0.7173(4) 0.5308(3) -0.0174(3) 0.0387(7) Uani 1 1 d . . . . .
H29A H 0.640844 0.512807 -0.073752 0.046 Uiso 1 1 calc R . . . .
H29B H 0.801649 0.544974 -0.070030 0.046 Uiso 1 1 calc R . . . .
C30 C 0.6595(4) 0.6666(3) 0.0470(3) 0.0407(7) Uani 1 1 d . . . . .
H30A H 0.630426 0.746493 -0.016643 0.061 Uiso 1 1 calc GR . . . .
H30B H 0.735617 0.686962 0.100822 0.061 Uiso 1 1 calc GR . . . .
H30C H 0.574930 0.653998 0.098275 0.061 Uiso 1 1 calc GR . . . .


_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
O10 C9 1.459(3) . ?
O10 C11 1.366(3) . ?
O26 C25 1.208(4) . ?
O27 C25 1.327(3) . ?
O27 C28 1.462(3) . ?
N1 C2 1.322(4) . ?
N1 C18 1.353(4) . ?
N7 C6 1.410(4) . ?
N7 C8 1.267(4) . ?
N16 C15 1.333(4) . ?
N16 C17 1.355(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.371(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.404(4) . ?
C5 C6 1.441(4) . ?
C5 C18 1.414(4) . ?
C6 C11 1.363(4) . ?
C8 C9 1.520(4) . ?
C8 C25 1.517(4) . ?
C9 H9 1.0000 . ?
C9 C19 1.514(4) . ?
C11 C12 1.435(4) . ?
C12 C13 1.403(4) . ?
C12 C17 1.409(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.366(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(4) . ?
C15 H15 0.9500 . ?
C17 C18 1.462(4) . ?
C19 C20 1.400(4) . ?
C19 C24 1.391(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(4) . ?
C24 H24 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.503(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.516(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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 O10 C9 116.7(2) . . ?
C25 O27 C28 117.9(2) . . ?
C2 N1 C18 117.1(3) . . ?
C8 N7 C6 116.5(3) . . ?
C15 N16 C17 116.3(3) . . ?
N1 C2 H2 117.8 . . ?
N1 C2 C3 124.5(3) . . ?
C3 C2 H2 117.8 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.9(3) . . ?
C4 C5 C18 117.9(3) . . ?
C18 C5 C6 120.2(3) . . ?
N7 C6 C5 118.9(3) . . ?
C11 C6 N7 121.2(3) . . ?
C11 C6 C5 119.7(3) . . ?
N7 C8 C9 126.1(3) . . ?
N7 C8 C25 118.8(3) . . ?
C25 C8 C9 115.0(2) . . ?
O10 C9 C8 109.9(2) . . ?
O10 C9 H9 107.9 . . ?
O10 C9 C19 111.2(2) . . ?
C8 C9 H9 107.9 . . ?
C19 C9 C8 111.9(2) . . ?
C19 C9 H9 107.9 . . ?
O10 C11 C12 115.5(3) . . ?
C6 C11 O10 122.2(3) . . ?
C6 C11 C12 122.3(3) . . ?
C13 C12 C11 122.1(3) . . ?
C13 C12 C17 118.7(3) . . ?
C17 C12 C11 119.1(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.3(3) . . ?
C15 C14 H14 120.9 . . ?
N16 C15 C14 125.5(3) . . ?
N16 C15 H15 117.2 . . ?
C14 C15 H15 117.2 . . ?
N16 C17 C12 122.3(3) . . ?
N16 C17 C18 118.2(3) . . ?
C12 C17 C18 119.5(3) . . ?
N1 C18 C5 122.7(3) . . ?
N1 C18 C17 118.2(3) . . ?
C5 C18 C17 119.1(3) . . ?
C20 C19 C9 118.9(3) . . ?
C24 C19 C9 121.6(3) . . ?
C24 C19 C20 119.5(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.1(3) . . ?
C23 C24 H24 119.9 . . ?
O26 C25 O27 126.3(3) . . ?
O26 C25 C8 122.7(3) . . ?
O27 C25 C8 111.0(2) . . ?
O27 C28 H28A 110.4 . . ?
O27 C28 H28B 110.4 . . ?
O27 C28 C29 106.8(2) . . ?
H28A C28 H28B 108.6 . . ?
C29 C28 H28A 110.4 . . ?
C29 C28 H28B 110.4 . . ?
C28 C29 H29A 108.9 . . ?
C28 C29 H29B 108.9 . . ?
C28 C29 C30 113.4(3) . . ?
H29A C29 H29B 107.7 . . ?
C30 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9 O10 1.00 2.65 3.383(4) 130 2_656 yes
C13 H13 O26 0.95 2.74 3.398(4) 127 2_656 yes
C24 H24 N1 0.95 2.68 3.363(4) 129 2_566 yes

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
O10 C9 C19 C20 -134.2(3) . . . . ?
O10 C9 C19 C24 46.1(4) . . . . ?
O10 C11 C12 C13 -4.1(4) . . . . ?
O10 C11 C12 C17 177.8(3) . . . . ?
O27 C28 C29 C30 50.9(4) . . . . ?
N1 C2 C3 C4 0.6(5) . . . . ?
N7 C6 C11 O10 0.0(4) . . . . ?
N7 C6 C11 C12 178.2(3) . . . . ?
N7 C8 C9 O10 -22.4(4) . . . . ?
N7 C8 C9 C19 101.7(3) . . . . ?
N7 C8 C25 O26 165.3(3) . . . . ?
N7 C8 C25 O27 -16.2(4) . . . . ?
N16 C17 C18 N1 4.0(4) . . . . ?
N16 C17 C18 C5 -176.1(3) . . . . ?
C2 N1 C18 C5 -0.4(4) . . . . ?
C2 N1 C18 C17 179.5(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 -178.9(3) . . . . ?
C3 C4 C5 C18 0.9(4) . . . . ?
C4 C5 C6 N7 1.8(4) . . . . ?
C4 C5 C6 C11 177.5(3) . . . . ?
C4 C5 C18 N1 -0.1(4) . . . . ?
C4 C5 C18 C17 -180.0(3) . . . . ?
C5 C6 C11 O10 -175.5(3) . . . . ?
C5 C6 C11 C12 2.7(4) . . . . ?
C6 N7 C8 C9 2.1(5) . . . . ?
C6 N7 C8 C25 -176.2(2) . . . . ?
C6 C5 C18 N1 179.6(3) . . . . ?
C6 C5 C18 C17 -0.2(4) . . . . ?
C6 C11 C12 C13 177.6(3) . . . . ?
C6 C11 C12 C17 -0.5(4) . . . . ?
C8 N7 C6 C5 -173.9(3) . . . . ?
C8 N7 C6 C11 10.5(4) . . . . ?
C8 C9 C19 C20 102.5(3) . . . . ?
C8 C9 C19 C24 -77.2(3) . . . . ?
C9 O10 C11 C6 -22.4(4) . . . . ?
C9 O10 C11 C12 159.3(2) . . . . ?
C9 C8 C25 O26 -13.2(4) . . . . ?
C9 C8 C25 O27 165.3(2) . . . . ?
C9 C19 C20 C21 -178.2(3) . . . . ?
C9 C19 C24 C23 179.7(3) . . . . ?
C11 O10 C9 C8 30.7(3) . . . . ?
C11 O10 C9 C19 -93.7(3) . . . . ?
C11 C12 C13 C14 -176.3(3) . . . . ?
C11 C12 C17 N16 176.4(3) . . . . ?
C11 C12 C17 C18 -2.0(4) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C12 C17 C18 N1 -177.5(3) . . . . ?
C12 C17 C18 C5 2.4(4) . . . . ?
C13 C12 C17 N16 -1.8(5) . . . . ?
C13 C12 C17 C18 179.8(3) . . . . ?
C13 C14 C15 N16 -1.2(5) . . . . ?
C15 N16 C17 C12 0.3(5) . . . . ?
C15 N16 C17 C18 178.7(3) . . . . ?
C17 N16 C15 C14 1.2(5) . . . . ?
C17 C12 C13 C14 1.8(4) . . . . ?
C18 N1 C2 C3 0.2(5) . . . . ?
C18 C5 C6 N7 -177.9(3) . . . . ?
C18 C5 C6 C11 -2.3(4) . . . . ?
C19 C20 C21 C22 -1.9(5) . . . . ?
C20 C19 C24 C23 0.0(4) . . . . ?
C20 C21 C22 C23 0.7(5) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C22 C23 C24 C19 -1.1(5) . . . . ?
C24 C19 C20 C21 1.5(4) . . . . ?
C25 O27 C28 C29 155.7(2) . . . . ?
C25 C8 C9 O10 156.0(2) . . . . ?
C25 C8 C9 C19 -80.0(3) . . . . ?
C28 O27 C25 O26 -6.2(4) . . . . ?
C28 O27 C25 C8 175.3(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_original_sample_id Muhib_02_19
_olex2_submission_special_instructions 'No special instructions were received'
