# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cmpd1
_database_code_depnum_ccdc_archive 'CCDC 2039678'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2020-10-20 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, Br O3, H2 O'
_chemical_formula_sum            'C16 H38 Br N O4'
_chemical_formula_weight         388.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.8000(4)
_cell_length_b                   12.7411(5)
_cell_length_c                   16.7622(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.0239(13)
_cell_angle_gamma                90
_cell_volume                     2061.03(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    2.010
_shelx_estimated_absorpt_T_min   0.546
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            40837
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5101
_reflns_number_gt                4386
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0217P)²+1.1549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5101
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0571
_refine_ls_wR_factor_gt          0.0538
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.003
_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
N1 N 0.60907(12) 0.78311(9) 0.56501(7) 0.0155(2) Uani 1 1 d . . . . .
C1 C 0.54975(14) 0.88733(11) 0.58769(8) 0.0167(3) Uani 1 1 d . . . . .
H1A H 0.611270 0.944446 0.575271 0.020 Uiso 1 1 calc R U . . .
H1B H 0.458250 0.897740 0.552866 0.020 Uiso 1 1 calc R U . . .
C2 C 0.53204(17) 0.89790(12) 0.67559(9) 0.0225(3) Uani 1 1 d . . . . .
H2A H 0.621817 0.885093 0.711599 0.027 Uiso 1 1 calc R U . . .
H2B H 0.464832 0.844986 0.688082 0.027 Uiso 1 1 calc R U . . .
C3 C 0.48019(16) 1.00774(12) 0.69057(9) 0.0236(3) Uani 1 1 d . . . . .
H3A H 0.548751 1.060088 0.678923 0.028 Uiso 1 1 calc R U . . .
H3B H 0.392120 1.020855 0.653005 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4569(2) 1.02185(14) 0.77741(10) 0.0334(4) Uani 1 1 d . . . . .
H4A H 0.388258 0.970688 0.789001 0.050 Uiso 1 1 calc R U . . .
H4B H 0.422959 1.093040 0.784360 0.050 Uiso 1 1 calc R U . . .
H4C H 0.544431 1.010887 0.814745 0.050 Uiso 1 1 calc R U . . .
C5 C 0.60463(15) 0.78634(11) 0.47406(8) 0.0172(3) Uani 1 1 d . . . . .
H5A H 0.508757 0.802663 0.447343 0.021 Uiso 1 1 calc R U . . .
H5B H 0.664885 0.844255 0.461556 0.021 Uiso 1 1 calc R U . . .
C6 C 0.65010(16) 0.68559(12) 0.43805(9) 0.0222(3) Uani 1 1 d . . . . .
H6A H 0.580528 0.629991 0.440851 0.027 Uiso 1 1 calc R U . . .
H6B H 0.739510 0.662126 0.469957 0.027 Uiso 1 1 calc R U . . .
C7 C 0.66624(17) 0.70242(13) 0.34973(9) 0.0256(3) Uani 1 1 d . . . . .
H7A H 0.665647 0.633199 0.322844 0.031 Uiso 1 1 calc R U . . .
H7B H 0.585405 0.742560 0.321725 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7979(2) 0.76041(15) 0.34001(11) 0.0371(4) Uani 1 1 d . . . . .
H8A H 0.796955 0.830717 0.363622 0.056 Uiso 1 1 calc R U . . .
H8B H 0.802957 0.766373 0.282311 0.056 Uiso 1 1 calc R U . . .
H8C H 0.878621 0.721534 0.367830 0.056 Uiso 1 1 calc R U . . .
C9 C 0.52562(15) 0.69136(11) 0.58862(8) 0.0186(3) Uani 1 1 d . . . . .
H9A H 0.529135 0.693044 0.647986 0.022 Uiso 1 1 calc R U . . .
H9B H 0.570043 0.625280 0.575497 0.022 Uiso 1 1 calc R U . . .
C10 C 0.37478(15) 0.68996(12) 0.54730(9) 0.0223(3) Uani 1 1 d . . . . .
H10A H 0.369443 0.679866 0.488277 0.027 Uiso 1 1 calc R U . . .
H10B H 0.331012 0.758095 0.555922 0.027 Uiso 1 1 calc R U . . .
C11 C 0.29721(18) 0.60189(14) 0.58122(10) 0.0308(4) Uani 1 1 d . . . . .
H11A H 0.350747 0.535960 0.581510 0.037 Uiso 1 1 calc R U . . .
H11B H 0.289245 0.618543 0.637920 0.037 Uiso 1 1 calc R U . . .
C12 C 0.1534(2) 0.58577(17) 0.53210(11) 0.0420(5) Uani 1 1 d . . . . .
H12A H 0.099607 0.650546 0.532372 0.063 Uiso 1 1 calc R U . . .
H12B H 0.106868 0.528724 0.555984 0.063 Uiso 1 1 calc R U . . .
H12C H 0.160979 0.567617 0.476223 0.063 Uiso 1 1 calc R U . . .
C13 C 0.75675(14) 0.76901(11) 0.60988(8) 0.0191(3) Uani 1 1 d . . . . .
H13A H 0.786791 0.696442 0.600811 0.023 Uiso 1 1 calc R U . . .
H13B H 0.757014 0.777103 0.668647 0.023 Uiso 1 1 calc R U . . .
C14 C 0.86225(15) 0.84477(12) 0.58548(9) 0.0236(3) Uani 1 1 d . . . . .
H14A H 0.879625 0.826494 0.530726 0.028 Uiso 1 1 calc R U . . .
H14B H 0.824857 0.917089 0.583525 0.028 Uiso 1 1 calc R U . . .
C15 C 0.99718(17) 0.83995(15) 0.64550(10) 0.0334(4) Uani 1 1 d . . . . .
H15A H 0.979177 0.859165 0.699949 0.040 Uiso 1 1 calc R U . . .
H15B H 1.032550 0.767023 0.648263 0.040 Uiso 1 1 calc R U . . .
C16 C 1.10693(18) 0.91255(17) 0.62299(13) 0.0416(5) Uani 1 1 d . . . . .
H16A H 1.126912 0.892807 0.569703 0.062 Uiso 1 1 calc R U . . .
H16B H 1.191638 0.906735 0.663550 0.062 Uiso 1 1 calc R U . . .
H16C H 1.073211 0.985077 0.621161 0.062 Uiso 1 1 calc R U . . .
Br1 Br 0.82282(2) 0.17629(2) 0.64570(2) 0.02129(5) Uani 1 1 d . . . . .
O1 O 0.73911(12) 0.10237(9) 0.57313(6) 0.0270(2) Uani 1 1 d . . . . .
O2 O 0.70260(13) 0.24600(9) 0.67964(7) 0.0335(3) Uani 1 1 d . . . . .
O3 O 0.88837(14) 0.09763(11) 0.71975(7) 0.0411(3) Uani 1 1 d . . . . .
O1W O 0.66432(17) 0.46682(12) 0.64701(9) 0.0456(4) Uani 1 1 d . . . . .
H1WA H 0.675(2) 0.406(2) 0.6600(13) 0.049(7) Uiso 1 1 d . . . . .
H1WB H 0.660(3) 0.498(2) 0.6898(16) 0.062(8) Uiso 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
N1 C9 1.5180(17) . ?
N1 C5 1.5181(17) . ?
N1 C13 1.5212(17) . ?
N1 C1 1.5240(17) . ?
C1 C2 1.5193(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.525(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.518(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.531(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.520(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.519(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.522(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.517(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.515(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Br1 O3 1.6372(12) . ?
Br1 O1 1.6407(11) . ?
Br1 O2 1.6535(12) . ?
O1W H1WA 0.81(3) . ?
O1W H1WB 0.83(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C5 111.11(10) . . ?
C9 N1 C13 106.83(10) . . ?
C5 N1 C13 110.99(11) . . ?
C9 N1 C1 111.08(10) . . ?
C5 N1 C1 106.34(10) . . ?
C13 N1 C1 110.55(10) . . ?
C2 C1 N1 115.60(11) . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
N1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 C3 109.79(12) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 112.05(13) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 114.66(11) . . ?
C6 C5 H5A 108.6 . . ?
N1 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
N1 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 110.67(12) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 113.84(13) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 114.56(11) . . ?
N1 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 110.39(13) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 112.00(14) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 115.13(11) . . ?
N1 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
N1 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 110.53(13) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 112.63(15) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 Br1 O1 106.88(6) . . ?
O3 Br1 O2 106.08(6) . . ?
O1 Br1 O2 105.62(6) . . ?
H1WA O1W H1WB 105(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 53.74(15) . . . . ?
C5 N1 C1 C2 174.76(12) . . . . ?
C13 N1 C1 C2 -64.67(15) . . . . ?
N1 C1 C2 C3 176.68(12) . . . . ?
C1 C2 C3 C4 178.48(13) . . . . ?
C9 N1 C5 C6 -54.77(15) . . . . ?
C13 N1 C5 C6 63.95(15) . . . . ?
C1 N1 C5 C6 -175.77(11) . . . . ?
N1 C5 C6 C7 -170.17(12) . . . . ?
C5 C6 C7 C8 76.64(17) . . . . ?
C5 N1 C9 C10 -56.96(15) . . . . ?
C13 N1 C9 C10 -178.15(12) . . . . ?
C1 N1 C9 C10 61.21(15) . . . . ?
N1 C9 C10 C11 -174.27(12) . . . . ?
C9 C10 C11 C12 -170.20(14) . . . . ?
C9 N1 C13 C14 171.80(12) . . . . ?
C5 N1 C13 C14 50.54(15) . . . . ?
C1 N1 C13 C14 -67.22(15) . . . . ?
N1 C13 C14 C15 167.67(13) . . . . ?
C13 C14 C15 C16 178.87(15) . . . . ?

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
O1W H1WA O2 0.81(3) 2.08(3) 2.878(2) 174(2) . yes
O1W H1WB O3 0.83(3) 2.09(3) 2.904(2) 166(2) 2_656 yes

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_cmpd4
_database_code_depnum_ccdc_archive 'CCDC 2039681'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2020-10-20 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H30 N P2, Cl O3'
_chemical_formula_sum            'C36 H30 Cl N O3 P2'
_chemical_formula_weight         622.00

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'
P P 0.1023 0.0942 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.4093(11)
_cell_length_b                   19.713(2)
_cell_length_c                   16.8064(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.680(4)
_cell_angle_gamma                90
_cell_volume                     3028.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9782
_cell_measurement_theta_min      4.56
_cell_measurement_theta_max      56.62

_exptl_crystal_description       tablet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            60453
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.619
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7533
_reflns_number_gt                6383
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0452P)²+2.8657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7533
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.60935(5) 0.19682(2) 0.29600(3) 0.01147(10) Uani 1 1 d . . . . .
P2 P 0.82372(5) 0.29918(2) 0.37933(3) 0.01138(10) Uani 1 1 d . . . . .
N1 N 0.69518(17) 0.26618(8) 0.31262(10) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.6237(2) 0.14161(9) 0.38266(11) 0.0150(4) Uani 1 1 d . . . . .
C2 C 0.7386(2) 0.09522(10) 0.40342(12) 0.0189(4) Uani 1 1 d . . . . .
H2 H 0.804940 0.089733 0.369184 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7552(2) 0.05699(10) 0.47487(13) 0.0247(4) Uani 1 1 d . . . . .
H3 H 0.833801 0.025705 0.489635 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6581(3) 0.06436(12) 0.52415(13) 0.0309(5) Uani 1 1 d . . . . .
H4 H 0.669702 0.037920 0.572525 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5440(3) 0.11004(13) 0.50348(13) 0.0303(5) Uani 1 1 d . . . . .
H5 H 0.476930 0.114552 0.537454 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5267(2) 0.14943(11) 0.43327(12) 0.0221(4) Uani 1 1 d . . . . .
H6 H 0.449345 0.181488 0.419815 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4194(2) 0.21648(10) 0.25513(11) 0.0143(3) Uani 1 1 d . . . . .
C8 C 0.3120(2) 0.16601(10) 0.24539(12) 0.0181(4) Uani 1 1 d . . . . .
H8 H 0.337217 0.121252 0.264552 0.022 Uiso 1 1 calc R U . . .
C9 C 0.1682(2) 0.18197(11) 0.20746(13) 0.0230(4) Uani 1 1 d . . . . .
H9 H 0.094203 0.148288 0.201542 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1325(2) 0.24707(12) 0.17822(13) 0.0249(5) Uani 1 1 d . . . . .
H10 H 0.034491 0.257528 0.151073 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2390(2) 0.29695(11) 0.18836(12) 0.0231(4) Uani 1 1 d . . . . .
H11 H 0.213572 0.341512 0.168506 0.028 Uiso 1 1 calc R U . . .
C12 C 0.3823(2) 0.28203(10) 0.22733(11) 0.0169(4) Uani 1 1 d . . . . .
H12 H 0.454981 0.316435 0.235055 0.020 Uiso 1 1 calc R U . . .
C13 C 0.66875(19) 0.14988(9) 0.21762(11) 0.0133(3) Uani 1 1 d . . . . .
C14 C 0.6364(2) 0.08117(10) 0.20534(12) 0.0177(4) Uani 1 1 d . . . . .
H14 H 0.585768 0.058144 0.239976 0.021 Uiso 1 1 calc R U . . .
C15 C 0.6775(2) 0.04628(10) 0.14294(12) 0.0201(4) Uani 1 1 d . . . . .
H15 H 0.655663 -0.000635 0.134986 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7505(2) 0.07982(11) 0.09208(12) 0.0206(4) Uani 1 1 d . . . . .
H16 H 0.779447 0.055864 0.049454 0.025 Uiso 1 1 calc R U . . .
C17 C 0.7815(2) 0.14850(11) 0.10346(12) 0.0213(4) Uani 1 1 d . . . . .
H17 H 0.830097 0.171565 0.067900 0.026 Uiso 1 1 calc R U . . .
C18 C 0.7419(2) 0.18368(10) 0.16642(12) 0.0169(4) Uani 1 1 d . . . . .
H18 H 0.764556 0.230509 0.174533 0.020 Uiso 1 1 calc R U . . .
C19 C 0.9486(2) 0.23910(9) 0.43870(11) 0.0139(3) Uani 1 1 d . . . . .
C20 C 1.0397(2) 0.20299(10) 0.39924(12) 0.0197(4) Uani 1 1 d . . . . .
H20 H 1.043837 0.214780 0.345026 0.024 Uiso 1 1 calc R U . . .
C21 C 1.1243(2) 0.14989(11) 0.43916(13) 0.0234(4) Uani 1 1 d . . . . .
H21 H 1.186109 0.125190 0.412357 0.028 Uiso 1 1 calc R U . . .
C22 C 1.1180(2) 0.13306(11) 0.51850(14) 0.0259(5) Uani 1 1 d . . . . .
H22 H 1.176331 0.096958 0.546088 0.031 Uiso 1 1 calc R U . . .
C23 C 1.0273(2) 0.16851(11) 0.55765(13) 0.0249(4) Uani 1 1 d . . . . .
H23 H 1.023012 0.156311 0.611717 0.030 Uiso 1 1 calc R U . . .
C24 C 0.9426(2) 0.22180(10) 0.51832(11) 0.0178(4) Uani 1 1 d . . . . .
H24 H 0.880906 0.246312 0.545418 0.021 Uiso 1 1 calc R U . . .
C25 C 0.9254(2) 0.35337(9) 0.32676(11) 0.0134(3) Uani 1 1 d . . . . .
C26 C 0.8515(2) 0.38324(10) 0.25337(11) 0.0166(4) Uani 1 1 d . . . . .
H26 H 0.750840 0.373784 0.231342 0.020 Uiso 1 1 calc R U . . .
C27 C 0.9265(2) 0.42705(10) 0.21266(12) 0.0211(4) Uani 1 1 d . . . . .
H27 H 0.876813 0.447606 0.162678 0.025 Uiso 1 1 calc R U . . .
C28 C 1.0735(2) 0.44078(10) 0.24483(13) 0.0213(4) Uani 1 1 d . . . . .
H28 H 1.124268 0.470500 0.216667 0.026 Uiso 1 1 calc R U . . .
C29 C 1.1462(2) 0.41131(11) 0.31780(13) 0.0223(4) Uani 1 1 d . . . . .
H29 H 1.246879 0.420869 0.339653 0.027 Uiso 1 1 calc R U . . .
C30 C 1.0727(2) 0.36783(10) 0.35918(12) 0.0183(4) Uani 1 1 d . . . . .
H30 H 1.122627 0.347948 0.409529 0.022 Uiso 1 1 calc R U . . .
C31 C 0.7519(2) 0.35172(9) 0.44787(11) 0.0138(3) Uani 1 1 d . . . . .
C32 C 0.6014(2) 0.35936(10) 0.43501(12) 0.0181(4) Uani 1 1 d . . . . .
H32 H 0.537687 0.335882 0.391411 0.022 Uiso 1 1 calc R U . . .
C33 C 0.5444(2) 0.40124(11) 0.48584(12) 0.0221(4) Uani 1 1 d . . . . .
H33 H 0.441420 0.406478 0.476634 0.027 Uiso 1 1 calc R U . . .
C34 C 0.6353(2) 0.43556(10) 0.54984(12) 0.0215(4) Uani 1 1 d . . . . .
H34 H 0.595036 0.463534 0.584972 0.026 Uiso 1 1 calc R U . . .
C35 C 0.7861(2) 0.42887(10) 0.56246(12) 0.0220(4) Uani 1 1 d . . . . .
H35 H 0.849044 0.452851 0.605871 0.026 Uiso 1 1 calc R U . . .
C36 C 0.8448(2) 0.38717(10) 0.51170(12) 0.0190(4) Uani 1 1 d . . . . .
H36 H 0.947901 0.382743 0.520306 0.023 Uiso 1 1 calc R U . . .
Cl1 Cl 0.48393(5) 0.50358(2) 0.22374(3) 0.02096(11) Uani 1 1 d . . . . .
O1 O 0.33263(18) 0.52862(9) 0.19405(12) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.5340(2) 0.47945(14) 0.15347(14) 0.0632(7) Uani 1 1 d . . . . .
O3 O 0.4789(3) 0.44720(16) 0.27806(19) 0.0920(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
P1 N1 1.5789(16) . ?
P1 C1 1.7976(19) . ?
P1 C7 1.7991(19) . ?
P1 C13 1.8035(19) . ?
P2 N1 1.5817(16) . ?
P2 C31 1.7958(18) . ?
P2 C19 1.7958(19) . ?
P2 C25 1.7992(18) . ?
C1 C2 1.396(3) . ?
C1 C6 1.395(3) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.390(3) . ?
C7 C8 1.400(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.392(3) . ?
C13 C14 1.393(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.395(3) . ?
C19 C20 1.397(3) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.393(3) . ?
C25 C26 1.395(3) . ?
C26 C27 1.393(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.387(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.389(3) . ?
C31 C36 1.400(3) . ?
C32 C33 1.384(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
Cl1 O3 1.446(2) . ?
Cl1 O2 1.451(2) . ?
Cl1 O1 1.4777(17) . ?

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 P1 C1 116.35(8) . . ?
N1 P1 C7 107.55(9) . . ?
C1 P1 C7 108.49(9) . . ?
N1 P1 C13 109.86(9) . . ?
C1 P1 C13 107.71(9) . . ?
C7 P1 C13 106.45(8) . . ?
N1 P2 C31 110.55(9) . . ?
N1 P2 C19 114.39(8) . . ?
C31 P2 C19 108.67(8) . . ?
N1 P2 C25 107.61(8) . . ?
C31 P2 C25 107.29(8) . . ?
C19 P2 C25 108.07(9) . . ?
P1 N1 P2 139.02(11) . . ?
C2 C1 C6 119.97(18) . . ?
C2 C1 P1 120.29(15) . . ?
C6 C1 P1 119.50(15) . . ?
C3 C2 C1 119.43(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 120.30(17) . . ?
C12 C7 P1 118.44(14) . . ?
C8 C7 P1 121.08(15) . . ?
C9 C8 C7 119.39(19) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.01(19) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.40(19) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 119.69(19) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C18 C13 C14 119.78(17) . . ?
C18 C13 P1 119.32(14) . . ?
C14 C13 P1 120.83(14) . . ?
C15 C14 C13 120.32(18) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.94(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 119.94(18) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.46(18) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 119.55(18) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C24 C19 C20 119.98(17) . . ?
C24 C19 P2 121.63(14) . . ?
C20 C19 P2 117.83(14) . . ?
C21 C20 C19 120.07(19) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.64(19) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 120.46(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 119.51(18) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C30 C25 C26 120.09(17) . . ?
C30 C25 P2 121.65(14) . . ?
C26 C25 P2 118.21(14) . . ?
C27 C26 C25 119.41(18) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C28 C27 C26 120.25(19) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 120.16(18) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 120.18(19) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 119.89(18) . . ?
C29 C30 H30 120.1 . . ?
C25 C30 H30 120.1 . . ?
C32 C31 C36 119.62(17) . . ?
C32 C31 P2 119.16(14) . . ?
C36 C31 P2 121.16(14) . . ?
C33 C32 C31 119.87(18) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.88(19) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.60(18) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.15(19) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 119.87(18) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
O3 Cl1 O2 109.09(19) . . ?
O3 Cl1 O1 107.30(12) . . ?
O2 Cl1 O1 107.87(12) . . ?

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
C1 P1 N1 P2 18.1(2) . . . . ?
C7 P1 N1 P2 139.95(16) . . . . ?
C13 P1 N1 P2 -104.58(17) . . . . ?
C31 P2 N1 P1 -98.75(17) . . . . ?
C19 P2 N1 P1 24.3(2) . . . . ?
C25 P2 N1 P1 144.38(16) . . . . ?
N1 P1 C1 C2 -87.45(17) . . . . ?
C7 P1 C1 C2 151.19(15) . . . . ?
C13 P1 C1 C2 36.34(17) . . . . ?
N1 P1 C1 C6 86.97(17) . . . . ?
C7 P1 C1 C6 -34.39(18) . . . . ?
C13 P1 C1 C6 -149.24(15) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
P1 C1 C2 C3 174.44(15) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
P1 C1 C6 C5 -175.49(16) . . . . ?
N1 P1 C7 C12 14.46(17) . . . . ?
C1 P1 C7 C12 141.08(15) . . . . ?
C13 P1 C7 C12 -103.24(15) . . . . ?
N1 P1 C7 C8 -170.50(15) . . . . ?
C1 P1 C7 C8 -43.87(17) . . . . ?
C13 P1 C7 C8 71.81(17) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
P1 C7 C8 C9 -174.73(15) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
P1 C7 C12 C11 173.74(14) . . . . ?
N1 P1 C13 C18 -18.32(17) . . . . ?
C1 P1 C13 C18 -145.97(15) . . . . ?
C7 P1 C13 C18 97.84(16) . . . . ?
N1 P1 C13 C14 164.70(15) . . . . ?
C1 P1 C13 C14 37.05(17) . . . . ?
C7 P1 C13 C14 -79.14(17) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
P1 C13 C14 C15 177.46(15) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C13 -0.9(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
P1 C13 C18 C17 -176.86(15) . . . . ?
N1 P2 C19 C24 -102.28(16) . . . . ?
C31 P2 C19 C24 21.77(18) . . . . ?
C25 P2 C19 C24 137.89(15) . . . . ?
N1 P2 C19 C20 69.15(17) . . . . ?
C31 P2 C19 C20 -166.79(15) . . . . ?
C25 P2 C19 C20 -50.67(17) . . . . ?
C24 C19 C20 C21 0.0(3) . . . . ?
P2 C19 C20 C21 -171.58(16) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C22 C23 C24 C19 0.5(3) . . . . ?
C20 C19 C24 C23 -0.1(3) . . . . ?
P2 C19 C24 C23 171.11(16) . . . . ?
N1 P2 C25 C30 -153.43(15) . . . . ?
C31 P2 C25 C30 87.58(17) . . . . ?
C19 P2 C25 C30 -29.43(18) . . . . ?
N1 P2 C25 C26 29.08(17) . . . . ?
C31 P2 C25 C26 -89.91(16) . . . . ?
C19 P2 C25 C26 153.08(14) . . . . ?
C30 C25 C26 C27 0.5(3) . . . . ?
P2 C25 C26 C27 178.06(14) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
C27 C28 C29 C30 0.0(3) . . . . ?
C28 C29 C30 C25 0.5(3) . . . . ?
C26 C25 C30 C29 -0.8(3) . . . . ?
P2 C25 C30 C29 -178.28(15) . . . . ?
N1 P2 C31 C32 -1.85(18) . . . . ?
C19 P2 C31 C32 -128.15(15) . . . . ?
C25 P2 C31 C32 115.22(16) . . . . ?
N1 P2 C31 C36 -179.15(15) . . . . ?
C19 P2 C31 C36 54.54(18) . . . . ?
C25 P2 C31 C36 -62.09(17) . . . . ?
C36 C31 C32 C33 -0.8(3) . . . . ?
P2 C31 C32 C33 -178.11(15) . . . . ?
C31 C32 C33 C34 -0.3(3) . . . . ?
C32 C33 C34 C35 1.1(3) . . . . ?
C33 C34 C35 C36 -0.9(3) . . . . ?
C34 C35 C36 C31 -0.2(3) . . . . ?
C32 C31 C36 C35 1.0(3) . . . . ?
P2 C31 C36 C35 178.29(15) . . . . ?

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_cmpd3
_database_code_depnum_ccdc_archive 'CCDC 2039680'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2020-10-20 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H30 N P2, Br O3'
_chemical_formula_sum            'C36 H30 Br N O3 P2'
_chemical_formula_weight         666.46

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4724(4)
_cell_length_b                   19.7442(9)
_cell_length_c                   16.8171(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.8180(13)
_cell_angle_gamma                90
_cell_volume                     3054.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    1.489
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7891
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            61375
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         28.213
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7529
_reflns_number_gt                6504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0242P)²+2.8908P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7529
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.60815(4) 0.19902(2) 0.29594(3) 0.01223(9) Uani 1 1 d . . . . .
P2 P 0.82310(5) 0.30065(2) 0.37977(3) 0.01234(9) Uani 1 1 d . . . . .
N1 N 0.69525(16) 0.26767(7) 0.31309(9) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.62024(18) 0.14355(9) 0.38200(10) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.7349(2) 0.09758(9) 0.40390(11) 0.0186(4) Uani 1 1 d . . . . .
H2 H 0.802405 0.092914 0.370599 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7505(2) 0.05867(9) 0.47421(12) 0.0240(4) Uani 1 1 d . . . . .
H3 H 0.829608 0.027977 0.489512 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6507(2) 0.06464(10) 0.52202(12) 0.0287(5) Uani 1 1 d . . . . .
H4 H 0.660535 0.037544 0.569719 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5364(2) 0.11006(12) 0.50041(12) 0.0300(5) Uani 1 1 d . . . . .
H5 H 0.468079 0.113858 0.533371 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5210(2) 0.14994(10) 0.43114(11) 0.0226(4) Uani 1 1 d . . . . .
H6 H 0.443289 0.181497 0.417066 0.027 Uiso 1 1 calc R U . . .
C7 C 0.42018(18) 0.21970(9) 0.25396(10) 0.0150(3) Uani 1 1 d . . . . .
C8 C 0.31247(19) 0.17001(10) 0.24197(11) 0.0191(4) Uani 1 1 d . . . . .
H8 H 0.336070 0.124897 0.259951 0.023 Uiso 1 1 calc R U . . .
C9 C 0.1703(2) 0.18716(11) 0.20346(12) 0.0242(4) Uani 1 1 d . . . . .
H9 H 0.096034 0.153821 0.196003 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1365(2) 0.25256(11) 0.17593(12) 0.0262(4) Uani 1 1 d . . . . .
H10 H 0.039470 0.263624 0.148585 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2436(2) 0.30216(10) 0.18800(11) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.219575 0.346971 0.168934 0.028 Uiso 1 1 calc R U . . .
C12 C 0.38548(19) 0.28625(9) 0.22790(10) 0.0175(3) Uani 1 1 d . . . . .
H12 H 0.458512 0.320274 0.237440 0.021 Uiso 1 1 calc R U . . .
C13 C 0.66780(18) 0.15169(9) 0.21818(10) 0.0139(3) Uani 1 1 d . . . . .
C14 C 0.63280(19) 0.08319(9) 0.20525(11) 0.0174(3) Uani 1 1 d . . . . .
H14 H 0.580257 0.060659 0.238988 0.021 Uiso 1 1 calc R U . . .
C15 C 0.6746(2) 0.04801(9) 0.14324(11) 0.0199(4) Uani 1 1 d . . . . .
H15 H 0.651296 0.001352 0.134872 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7503(2) 0.08075(10) 0.09350(11) 0.0211(4) Uani 1 1 d . . . . .
H16 H 0.779150 0.056551 0.051169 0.025 Uiso 1 1 calc R U . . .
C17 C 0.7840(2) 0.14914(10) 0.10564(12) 0.0228(4) Uani 1 1 d . . . . .
H17 H 0.835133 0.171669 0.071151 0.027 Uiso 1 1 calc R U . . .
C18 C 0.74337(19) 0.18465(9) 0.16795(11) 0.0180(3) Uani 1 1 d . . . . .
H18 H 0.767068 0.231275 0.176247 0.022 Uiso 1 1 calc R U . . .
C19 C 0.94801(18) 0.24073(8) 0.43858(10) 0.0152(3) Uani 1 1 d . . . . .
C20 C 1.03993(19) 0.20556(9) 0.39882(11) 0.0190(4) Uani 1 1 d . . . . .
H20 H 1.044746 0.218094 0.344992 0.023 Uiso 1 1 calc R U . . .
C21 C 1.1239(2) 0.15236(10) 0.43841(12) 0.0238(4) Uani 1 1 d . . . . .
H21 H 1.186238 0.128343 0.411694 0.029 Uiso 1 1 calc R U . . .
C22 C 1.1166(2) 0.13433(10) 0.51688(12) 0.0258(4) Uani 1 1 d . . . . .
H22 H 1.173876 0.097765 0.543717 0.031 Uiso 1 1 calc R U . . .
C23 C 1.0265(2) 0.16912(10) 0.55666(12) 0.0246(4) Uani 1 1 d . . . . .
H23 H 1.022337 0.156347 0.610517 0.029 Uiso 1 1 calc R U . . .
C24 C 0.9421(2) 0.22274(9) 0.51782(11) 0.0193(4) Uani 1 1 d . . . . .
H24 H 0.880814 0.246900 0.545145 0.023 Uiso 1 1 calc R U . . .
C25 C 0.92254(18) 0.35494(8) 0.32679(10) 0.0147(3) Uani 1 1 d . . . . .
C26 C 0.8478(2) 0.38470(9) 0.25345(11) 0.0182(4) Uani 1 1 d . . . . .
H26 H 0.747678 0.375155 0.231854 0.022 Uiso 1 1 calc R U . . .
C27 C 0.9208(2) 0.42834(9) 0.21229(12) 0.0225(4) Uani 1 1 d . . . . .
H27 H 0.870327 0.448731 0.162421 0.027 Uiso 1 1 calc R U . . .
C28 C 1.0669(2) 0.44232(9) 0.24355(12) 0.0229(4) Uani 1 1 d . . . . .
H28 H 1.116282 0.472075 0.214956 0.027 Uiso 1 1 calc R U . . .
C29 C 1.1413(2) 0.41296(10) 0.31651(12) 0.0229(4) Uani 1 1 d . . . . .
H29 H 1.241499 0.422564 0.337693 0.027 Uiso 1 1 calc R U . . .
C30 C 1.06948(19) 0.36954(9) 0.35866(11) 0.0191(4) Uani 1 1 d . . . . .
H30 H 1.120106 0.349848 0.408940 0.023 Uiso 1 1 calc R U . . .
C31 C 0.75179(18) 0.35249(8) 0.44880(10) 0.0145(3) Uani 1 1 d . . . . .
C32 C 0.60224(19) 0.35921(9) 0.43668(11) 0.0186(4) Uani 1 1 d . . . . .
H32 H 0.538795 0.334964 0.393842 0.022 Uiso 1 1 calc R U . . .
C33 C 0.5456(2) 0.40160(10) 0.48753(11) 0.0226(4) Uani 1 1 d . . . . .
H33 H 0.443237 0.406515 0.478834 0.027 Uiso 1 1 calc R U . . .
C34 C 0.6366(2) 0.43649(10) 0.55038(11) 0.0232(4) Uani 1 1 d . . . . .
H34 H 0.597099 0.464658 0.585434 0.028 Uiso 1 1 calc R U . . .
C35 C 0.7862(2) 0.43037(10) 0.56232(12) 0.0237(4) Uani 1 1 d . . . . .
H35 H 0.848947 0.454872 0.605191 0.028 Uiso 1 1 calc R U . . .
C36 C 0.8444(2) 0.38872(9) 0.51205(11) 0.0196(4) Uani 1 1 d . . . . .
H36 H 0.946883 0.384700 0.520380 0.024 Uiso 1 1 calc R U . . .
Br1 Br 0.48229(2) 0.50962(2) 0.22376(2) 0.01929(5) Uani 1 1 d . . . . .
O1 O 0.31163(15) 0.53224(8) 0.18770(10) 0.0324(3) Uani 1 1 d . . . . .
O2 O 0.5359(2) 0.47518(12) 0.14875(12) 0.0579(6) Uani 1 1 d . . . . .
O3 O 0.4797(2) 0.45088(12) 0.29120(14) 0.0662(7) 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
P1 N1 1.5771(15) . ?
P1 C1 1.7967(17) . ?
P1 C7 1.7987(17) . ?
P1 C13 1.8043(17) . ?
P2 N1 1.5809(15) . ?
P2 C19 1.7942(17) . ?
P2 C31 1.7961(17) . ?
P2 C25 1.7974(17) . ?
C1 C2 1.396(2) . ?
C1 C6 1.398(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.395(2) . ?
C7 C12 1.399(2) . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.392(2) . ?
C13 C14 1.397(2) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.393(2) . ?
C19 C20 1.402(2) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.397(2) . ?
C25 C30 1.397(2) . ?
C26 C27 1.389(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.389(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.389(2) . ?
C31 C36 1.403(2) . ?
C32 C33 1.393(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.378(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
Br1 O2 1.6178(17) . ?
Br1 O3 1.6264(17) . ?
Br1 O1 1.6469(14) . ?

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 P1 C1 116.53(8) . . ?
N1 P1 C7 107.59(8) . . ?
C1 P1 C7 108.74(8) . . ?
N1 P1 C13 109.69(8) . . ?
C1 P1 C13 107.30(8) . . ?
C7 P1 C13 106.57(8) . . ?
N1 P2 C19 114.33(8) . . ?
N1 P2 C31 110.52(8) . . ?
C19 P2 C31 108.65(8) . . ?
N1 P2 C25 107.30(8) . . ?
C19 P2 C25 108.17(8) . . ?
C31 P2 C25 107.64(8) . . ?
P1 N1 P2 139.67(10) . . ?
C2 C1 C6 119.57(16) . . ?
C2 C1 P1 120.33(13) . . ?
C6 C1 P1 119.92(14) . . ?
C3 C2 C1 120.19(18) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.91(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.13(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.49(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.70(19) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C12 120.42(16) . . ?
C8 C7 P1 121.22(14) . . ?
C12 C7 P1 118.20(13) . . ?
C9 C8 C7 119.32(18) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.32(18) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.43(18) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.01(18) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 119.47(17) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C18 C13 C14 119.69(16) . . ?
C18 C13 P1 119.55(13) . . ?
C14 C13 P1 120.69(13) . . ?
C15 C14 C13 120.13(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.16(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.88(17) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.33(17) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 119.81(16) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C24 C19 C20 120.11(16) . . ?
C24 C19 P2 121.55(13) . . ?
C20 C19 P2 117.82(13) . . ?
C21 C20 C19 119.74(17) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 119.91(18) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.63(17) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.10(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 119.52(17) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C26 C25 C30 120.03(16) . . ?
C26 C25 P2 118.27(13) . . ?
C30 C25 P2 121.67(13) . . ?
C27 C26 C25 119.57(17) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C27 C26 120.37(18) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 120.16(17) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C30 120.13(18) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 119.73(17) . . ?
C29 C30 H30 120.1 . . ?
C25 C30 H30 120.1 . . ?
C32 C31 C36 119.62(16) . . ?
C32 C31 P2 119.18(13) . . ?
C36 C31 P2 121.13(13) . . ?
C31 C32 C33 119.78(17) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C34 C33 C32 120.58(18) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 119.84(17) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 120.34(18) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C31 119.83(17) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
O2 Br1 O3 107.69(13) . . ?
O2 Br1 O1 106.86(9) . . ?
O3 Br1 O1 105.85(9) . . ?

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
C1 P1 N1 P2 17.77(19) . . . . ?
C7 P1 N1 P2 140.11(15) . . . . ?
C13 P1 N1 P2 -104.35(16) . . . . ?
C19 P2 N1 P1 25.39(19) . . . . ?
C31 P2 N1 P1 -97.56(16) . . . . ?
C25 P2 N1 P1 145.35(15) . . . . ?
N1 P1 C1 C2 -85.92(16) . . . . ?
C7 P1 C1 C2 152.34(14) . . . . ?
C13 P1 C1 C2 37.45(16) . . . . ?
N1 P1 C1 C6 89.11(16) . . . . ?
C7 P1 C1 C6 -32.63(17) . . . . ?
C13 P1 C1 C6 -147.53(14) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
P1 C1 C2 C3 174.79(14) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
P1 C1 C6 C5 -175.84(15) . . . . ?
N1 P1 C7 C8 -171.79(14) . . . . ?
C1 P1 C7 C8 -44.75(16) . . . . ?
C13 P1 C7 C8 70.62(16) . . . . ?
N1 P1 C7 C12 12.82(16) . . . . ?
C1 P1 C7 C12 139.86(14) . . . . ?
C13 P1 C7 C12 -104.77(14) . . . . ?
C12 C7 C8 C9 0.3(3) . . . . ?
P1 C7 C8 C9 -174.96(14) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C7 1.5(3) . . . . ?
C8 C7 C12 C11 -1.7(3) . . . . ?
P1 C7 C12 C11 173.74(14) . . . . ?
N1 P1 C13 C18 -17.96(16) . . . . ?
C1 P1 C13 C18 -145.43(14) . . . . ?
C7 P1 C13 C18 98.23(15) . . . . ?
N1 P1 C13 C14 165.20(14) . . . . ?
C1 P1 C13 C14 37.72(16) . . . . ?
C7 P1 C13 C14 -78.61(15) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
P1 C13 C14 C15 177.57(14) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
P1 C13 C18 C17 -177.20(14) . . . . ?
N1 P2 C19 C24 -101.79(15) . . . . ?
C31 P2 C19 C24 22.17(17) . . . . ?
C25 P2 C19 C24 138.74(15) . . . . ?
N1 P2 C19 C20 69.92(16) . . . . ?
C31 P2 C19 C20 -166.12(13) . . . . ?
C25 P2 C19 C20 -49.55(16) . . . . ?
C24 C19 C20 C21 0.6(3) . . . . ?
P2 C19 C20 C21 -171.21(14) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C19 0.5(3) . . . . ?
C20 C19 C24 C23 -0.8(3) . . . . ?
P2 C19 C24 C23 170.68(15) . . . . ?
N1 P2 C25 C26 29.10(16) . . . . ?
C19 P2 C25 C26 152.90(13) . . . . ?
C31 P2 C25 C26 -89.87(15) . . . . ?
N1 P2 C25 C30 -153.19(14) . . . . ?
C19 P2 C25 C30 -29.38(17) . . . . ?
C31 P2 C25 C30 87.85(16) . . . . ?
C30 C25 C26 C27 0.5(3) . . . . ?
P2 C25 C26 C27 178.26(14) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C26 C27 C28 C29 -0.3(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C25 0.7(3) . . . . ?
C26 C25 C30 C29 -0.9(3) . . . . ?
P2 C25 C30 C29 -178.59(14) . . . . ?
N1 P2 C31 C32 -1.28(17) . . . . ?
C19 P2 C31 C32 -127.47(14) . . . . ?
C25 P2 C31 C32 115.61(15) . . . . ?
N1 P2 C31 C36 -178.17(14) . . . . ?
C19 P2 C31 C36 55.63(16) . . . . ?
C25 P2 C31 C36 -61.29(16) . . . . ?
C36 C31 C32 C33 -0.2(3) . . . . ?
P2 C31 C32 C33 -177.17(14) . . . . ?
C31 C32 C33 C34 -0.6(3) . . . . ?
C32 C33 C34 C35 1.2(3) . . . . ?
C33 C34 C35 C36 -0.8(3) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
C32 C31 C36 C35 0.6(3) . . . . ?
P2 C31 C36 C35 177.46(14) . . . . ?

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_cmpd2
_database_code_depnum_ccdc_archive 'CCDC 2039679'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2020-10-20 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;

_vrf_PLAT413_cmpd2               
;
RESPONSE: This close contact is a result of the disorder in the butyl chain
containing C27. The disorder is 0.87:0.13, and this clash is a result of
the position of the minor component. Presumably the hydrogen atoms bonded 
to C16 rotate slightly to accomodate this. However, there is no useful
new informaton to be obtained by modeling that disorder on C16.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, Cl O3'
_chemical_formula_sum            'C16 H36 Cl N O3'
_chemical_formula_weight         325.91

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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.0476(16)
_cell_length_b                   24.535(3)
_cell_length_c                   14.501(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.010(2)
_cell_angle_gamma                90
_cell_volume                     3915.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7012
_exptl_absorpt_correction_T_max  0.7844
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            75236
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.660
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9754
_reflns_number_gt                7784
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          
;
One tetrabutyl ammonium cation and one chlorate anion were disordered over
two sites. Each was refined with independent occupancies, yet both refined 
to about 0.87:0.13 occupancy. Minor component disorder was modeled with 
isotropic displacement parameters.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+2.0911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9754
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.009
_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
N1 N 0.53506(10) 0.37398(4) 0.45736(8) 0.0200(2) Uani 1 1 d . . . . .
C1 C 0.57001(13) 0.38316(5) 0.56938(10) 0.0215(3) Uani 1 1 d . . . . .
H1A H 0.636929 0.410108 0.593920 0.026 Uiso 1 1 calc R U . . .
H1B H 0.499590 0.399470 0.577877 0.026 Uiso 1 1 calc R U . . .
C2 C 0.60976(14) 0.33285(6) 0.63588(11) 0.0272(3) Uani 1 1 d . . . . .
H2A H 0.678865 0.315272 0.627197 0.033 Uiso 1 1 calc R U . . .
H2B H 0.541994 0.306365 0.615808 0.033 Uiso 1 1 calc R U . . .
C3 C 0.64793(15) 0.34906(6) 0.74689(11) 0.0304(3) Uani 1 1 d . . . . .
H3A H 0.584885 0.373222 0.752050 0.036 Uiso 1 1 calc R U . . .
H3B H 0.651807 0.315837 0.786830 0.036 Uiso 1 1 calc R U . . .
C4 C 0.76956(16) 0.37793(7) 0.79245(13) 0.0389(4) Uani 1 1 d . . . . .
H4A H 0.832373 0.354642 0.786443 0.058 Uiso 1 1 calc R U . . .
H4B H 0.790087 0.385555 0.863876 0.058 Uiso 1 1 calc R U . . .
H4C H 0.764857 0.412260 0.756496 0.058 Uiso 1 1 calc R U . . .
C5 C 0.43957(13) 0.32971(5) 0.41532(11) 0.0240(3) Uani 1 1 d . . . . .
H5A H 0.420059 0.325540 0.342458 0.029 Uiso 1 1 calc R U . . .
H5B H 0.475202 0.294864 0.448666 0.029 Uiso 1 1 calc R U . . .
C6 C 0.32220(13) 0.33914(6) 0.42767(12) 0.0272(3) Uani 1 1 d . . . . .
H6A H 0.278971 0.370941 0.386804 0.033 Uiso 1 1 calc R U . . .
H6B H 0.340070 0.346907 0.499319 0.033 Uiso 1 1 calc R U . . .
C7 C 0.24230(14) 0.28834(6) 0.39322(12) 0.0317(3) Uani 1 1 d . . . . .
H7A H 0.221843 0.281865 0.320733 0.038 Uiso 1 1 calc R U . . .
H7B H 0.288255 0.256336 0.431405 0.038 Uiso 1 1 calc R U . . .
C8 C 0.12546(15) 0.29403(8) 0.40910(14) 0.0402(4) Uani 1 1 d . . . . .
H8A H 0.145218 0.303428 0.479729 0.060 Uiso 1 1 calc R U . . .
H8B H 0.080855 0.259470 0.392689 0.060 Uiso 1 1 calc R U . . .
H8C H 0.075105 0.322859 0.365102 0.060 Uiso 1 1 calc R U . . .
C9 C 0.64311(13) 0.35505(5) 0.43700(11) 0.0230(3) Uani 1 1 d . . . . .
H9A H 0.666768 0.318202 0.466244 0.028 Uiso 1 1 calc R U . . .
H9B H 0.617080 0.351827 0.363074 0.028 Uiso 1 1 calc R U . . .
C10 C 0.75424(13) 0.39156(6) 0.47843(11) 0.0254(3) Uani 1 1 d . . . . .
H10A H 0.798200 0.385456 0.551955 0.031 Uiso 1 1 calc R U . . .
H10B H 0.728756 0.430237 0.467574 0.031 Uiso 1 1 calc R U . . .
C11 C 0.83820(14) 0.37923(6) 0.42572(13) 0.0312(3) Uani 1 1 d . . . . .
H11A H 0.858909 0.339962 0.433035 0.037 Uiso 1 1 calc R U . . .
H11B H 0.795035 0.387227 0.352777 0.037 Uiso 1 1 calc R U . . .
C12 C 0.95401(16) 0.41237(8) 0.46867(16) 0.0433(4) Uani 1 1 d . . . . .
H12A H 0.933800 0.451213 0.465273 0.065 Uiso 1 1 calc R U . . .
H12B H 1.002252 0.405443 0.429393 0.065 Uiso 1 1 calc R U . . .
H12C H 1.001003 0.401907 0.539165 0.065 Uiso 1 1 calc R U . . .
C13 C 0.48670(13) 0.42838(5) 0.40704(10) 0.0217(3) Uani 1 1 d . . . . .
H13A H 0.412320 0.437193 0.417282 0.026 Uiso 1 1 calc R U . . .
H13B H 0.547727 0.456801 0.441915 0.026 Uiso 1 1 calc R U . . .
C14 C 0.45677(15) 0.43165(6) 0.29521(11) 0.0300(3) Uani 1 1 d . . . . .
H14A H 0.402336 0.401204 0.259457 0.036 Uiso 1 1 calc R U . . .
H14B H 0.532207 0.428610 0.283875 0.036 Uiso 1 1 calc R U . . .
C15 C 0.39471(14) 0.48587(6) 0.25429(11) 0.0290(3) Uani 1 1 d . . . . .
H15A H 0.315409 0.486822 0.259672 0.035 Uiso 1 1 calc R U . . .
H15B H 0.445298 0.515803 0.296324 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3744(2) 0.49530(8) 0.14553(14) 0.0547(6) Uani 1 1 d . . . . .
H16A H 0.452667 0.494885 0.139826 0.082 Uiso 1 1 calc R U . . .
H16B H 0.335030 0.530730 0.123095 0.082 Uiso 1 1 calc R U . . .
H16C H 0.322205 0.466413 0.103180 0.082 Uiso 1 1 calc R U . . .
N2 N 0.75536(11) 0.63949(5) 0.11911(9) 0.0237(2) Uani 1 1 d . . . . .
C17 C 0.77222(16) 0.67269(7) 0.21411(12) 0.0262(4) Uani 0.8793(18) 1 d . . P A
1
H17A H 0.723964 0.655263 0.247295 0.031 Uiso 0.8793(18) 1 calc R U P A 1
H17B H 0.858759 0.670749 0.261719 0.031 Uiso 0.8793(18) 1 calc R U P A 1
C18 C 0.73563(18) 0.73247(7) 0.19561(14) 0.0323(4) Uani 0.8793(18) 1 d . . P A
1
H18A H 0.651024 0.735216 0.144283 0.039 Uiso 0.8793(18) 1 calc R U P A 1
H18B H 0.789115 0.751443 0.169163 0.039 Uiso 0.8793(18) 1 calc R U P A 1
C19 C 0.7454(2) 0.76012(8) 0.29353(19) 0.0383(5) Uani 0.8793(18) 1 d . . P A 1
H19A H 0.826628 0.752325 0.347214 0.046 Uiso 0.8793(18) 1 calc R U P A 1
H19B H 0.739037 0.800059 0.282879 0.046 Uiso 0.8793(18) 1 calc R U P A 1
C20 C 0.6497(2) 0.74213(9) 0.32937(15) 0.0398(5) Uani 0.8793(18) 1 d . . P A 1
H20A H 0.568866 0.749802 0.276892 0.060 Uiso 0.8793(18) 1 calc R U P A 1
H20B H 0.660438 0.761986 0.391063 0.060 Uiso 0.8793(18) 1 calc R U P A 1
H20C H 0.657812 0.702914 0.343420 0.060 Uiso 0.8793(18) 1 calc R U P A 1
C21 C 0.78707(15) 0.58089(7) 0.14866(13) 0.0258(3) Uani 0.8793(18) 1 d . . P A
1
H21A H 0.763735 0.559091 0.086111 0.031 Uiso 0.8793(18) 1 calc R U P A 1
H21B H 0.736686 0.568150 0.183913 0.031 Uiso 0.8793(18) 1 calc R U P A 1
C23 C 0.93956(18) 0.50826(8) 0.22988(16) 0.0353(4) Uani 0.8793(18) 1 d . . P A
1
H23A H 0.916616 0.490945 0.162968 0.042 Uiso 0.8793(18) 1 calc R U P A 1
H23B H 0.885290 0.493446 0.259870 0.042 Uiso 0.8793(18) 1 calc R U P A 1
C25 C 0.62275(15) 0.64256(7) 0.04264(12) 0.0263(3) Uani 0.8793(18) 1 d . . P A
1
H25A H 0.605540 0.680398 0.017014 0.032 Uiso 0.8793(18) 1 calc R U P A 1
H25B H 0.612849 0.618763 -0.015324 0.032 Uiso 0.8793(18) 1 calc R U P A 1
C26 C 0.52856(16) 0.62618(8) 0.08242(15) 0.0339(4) Uani 0.8793(18) 1 d . . P A
1
H26A H 0.536837 0.649739 0.140297 0.041 Uiso 0.8793(18) 1 calc R U P A 1
H26B H 0.542883 0.588007 0.106512 0.041 Uiso 0.8793(18) 1 calc R U P A 1
C27 C 0.40005(17) 0.63159(8) -0.00018(14) 0.0354(4) Uani 0.8793(18) 1 d . . P A
1
H27A H 0.341061 0.624999 0.030201 0.042 Uiso 0.8793(18) 1 calc R U P A 1
H27B H 0.388403 0.669521 -0.025676 0.042 Uiso 0.8793(18) 1 calc R U P A 1
C28 C 0.3714(2) 0.59340(11) -0.08842(18) 0.0504(6) Uani 0.8793(18) 1 d . . P A
1
H28A H 0.420604 0.603241 -0.125626 0.076 Uiso 0.8793(18) 1 calc R U P A 1
H28B H 0.285042 0.596263 -0.133303 0.076 Uiso 0.8793(18) 1 calc R U P A 1
H28C H 0.390041 0.555898 -0.063672 0.076 Uiso 0.8793(18) 1 calc R U P A 1
C29 C 0.83466(16) 0.66516(7) 0.07191(13) 0.0277(4) Uani 0.8793(18) 1 d . . P A
1
H29A H 0.801698 0.701703 0.046218 0.033 Uiso 0.8793(18) 1 calc R U P A 1
H29B H 0.917237 0.670349 0.125454 0.033 Uiso 0.8793(18) 1 calc R U P A 1
C30 C 0.84529(19) 0.63328(8) -0.01330(15) 0.0336(4) Uani 0.8793(18) 1 d . . P A
1
H30A H 0.763340 0.626974 -0.067065 0.040 Uiso 0.8793(18) 1 calc R U P A 1
H30B H 0.882819 0.597373 0.011972 0.040 Uiso 0.8793(18) 1 calc R U P A 1
C17A C 0.7534(13) 0.6925(6) 0.1453(11) 0.036(3) Uiso 0.1207(18) 1 d . . P A 2
H17C H 0.695426 0.712411 0.085757 0.043 Uiso 0.1207(18) 1 calc R U P A 2
H17D H 0.835000 0.708301 0.161993 0.043 Uiso 0.1207(18) 1 calc R U P A 2
C18A C 0.7203(12) 0.7023(5) 0.2298(10) 0.030(3) Uiso 0.1207(18) 1 d . . P A 2
H18C H 0.782710 0.686168 0.291714 0.036 Uiso 0.1207(18) 1 calc R U P A 2
H18D H 0.641863 0.684199 0.216576 0.036 Uiso 0.1207(18) 1 calc R U P A 2
C19A C 0.7094(13) 0.7612(6) 0.2461(12) 0.027(3) Uiso 0.1207(18) 1 d . . P A 2
H19C H 0.653257 0.777449 0.181432 0.032 Uiso 0.1207(18) 1 calc R U P A 2
H19D H 0.790041 0.778210 0.264094 0.032 Uiso 0.1207(18) 1 calc R U P A 2
C20A C 0.6641(16) 0.7763(8) 0.3279(13) 0.046(4) Uiso 0.1207(18) 1 d . . P A 2
H20D H 0.577869 0.766898 0.304481 0.069 Uiso 0.1207(18) 1 calc R U P A 2
H20E H 0.674486 0.815582 0.341364 0.069 Uiso 0.1207(18) 1 calc R U P A 2
H20F H 0.710995 0.756208 0.390039 0.069 Uiso 0.1207(18) 1 calc R U P A 2
C21A C 0.8679(11) 0.6075(5) 0.2042(9) 0.026(3) Uiso 0.1207(18) 1 d . . P A 2
H21C H 0.934013 0.634714 0.222144 0.031 Uiso 0.1207(18) 1 calc R U P A 2
H21D H 0.844419 0.607441 0.262169 0.031 Uiso 0.1207(18) 1 calc R U P A 2
C23A C 1.0030(14) 0.5280(6) 0.2824(12) 0.036(3) Uiso 0.1207(18) 1 d . . P A 2
H23C H 1.056426 0.553006 0.335549 0.044 Uiso 0.1207(18) 1 calc R U P A 2
H23D H 0.949202 0.512145 0.311821 0.044 Uiso 0.1207(18) 1 calc R U P A 2
C25A C 0.6503(13) 0.6011(6) 0.1017(11) 0.036(3) Uiso 0.1207(18) 1 d . . P A 2
H25C H 0.665720 0.565775 0.076157 0.044 Uiso 0.1207(18) 1 calc R U P A 2
H25D H 0.642927 0.594456 0.166281 0.044 Uiso 0.1207(18) 1 calc R U P A 2
C26A C 0.5370(13) 0.6247(6) 0.0284(13) 0.037(3) Uiso 0.1207(18) 1 d . . P A 2
H26C H 0.542410 0.629267 -0.037496 0.045 Uiso 0.1207(18) 1 calc R U P A 2
H26D H 0.524060 0.661084 0.051887 0.045 Uiso 0.1207(18) 1 calc R U P A 2
C27A C 0.4286(15) 0.5870(7) 0.0157(13) 0.047(4) Uiso 0.1207(18) 1 d . . P A 2
H27C H 0.443108 0.550819 -0.007563 0.056 Uiso 0.1207(18) 1 calc R U P A 2
H27D H 0.426016 0.581972 0.082526 0.056 Uiso 0.1207(18) 1 calc R U P A 2
C29A C 0.7873(15) 0.6322(7) 0.0225(12) 0.043(4) Uiso 0.1207(18) 1 d . . P A 2
H29C H 0.792621 0.592643 0.011339 0.052 Uiso 0.1207(18) 1 calc R U P A 2
H29D H 0.718114 0.646584 -0.037098 0.052 Uiso 0.1207(18) 1 calc R U P A 2
C28A C 0.306(2) 0.6077(10) -0.0575(17) 0.070(6) Uiso 0.1207(18) 1 d . . P A 2
H28D H 0.296142 0.645687 -0.041279 0.106 Uiso 0.1207(18) 1 calc R U P A 2
H28E H 0.241882 0.585329 -0.052208 0.106 Uiso 0.1207(18) 1 calc R U P A 2
H28F H 0.301789 0.605685 -0.126436 0.106 Uiso 0.1207(18) 1 calc R U P A 2
C30A C 0.9003(19) 0.6582(9) 0.0249(16) 0.059(5) Uiso 0.1207(18) 1 d . . P A 2
H30C H 0.904437 0.694982 0.054299 0.070 Uiso 0.1207(18) 1 calc R U P A 2
H30D H 0.969300 0.637224 0.073953 0.070 Uiso 0.1207(18) 1 calc R U P A 2
C22 C 0.91825(16) 0.56866(8) 0.21507(14) 0.0412(4) Uani 1 1 d . . . . .
H22A H 0.970858 0.583850 0.183806 0.049 Uiso 0.8793(18) 1 calc R U P A 1
H22B H 0.940516 0.586442 0.281511 0.049 Uiso 0.8793(18) 1 calc R U P A 1
H22C H 0.958603 0.575107 0.168684 0.049 Uiso 0.1207(18) 1 calc R U P A 2
H22D H 0.849633 0.544195 0.176519 0.049 Uiso 0.1207(18) 1 calc R U P A 2
C24 C 1.06863(18) 0.49251(9) 0.29623(18) 0.0555(5) Uani 1 1 d . . . . .
H24A H 1.123365 0.506881 0.267295 0.067 Uiso 0.8793(18) 1 calc R U P A 1
H24B H 1.075377 0.452696 0.300552 0.067 Uiso 0.8793(18) 1 calc R U P A 1
H24C H 1.090996 0.507708 0.363934 0.067 Uiso 0.8793(18) 1 calc R U P A 1
H24D H 1.076815 0.473331 0.357951 0.067 Uiso 0.1207(18) 1 calc R U P A 2
H24E H 1.148228 0.506279 0.303770 0.067 Uiso 0.1207(18) 1 calc R U P A 2
H24F H 1.037325 0.467322 0.238877 0.067 Uiso 0.1207(18) 1 calc R U P A 2
C31 C 0.9226(2) 0.66447(9) -0.05646(16) 0.0481(5) Uani 1 1 d . . . . .
H31A H 0.882048 0.699368 -0.085264 0.058 Uiso 0.8793(18) 1 calc R U P A 1
H31B H 1.002252 0.673045 -0.001290 0.058 Uiso 0.8793(18) 1 calc R U P A 1
H31C H 0.995786 0.687935 -0.030342 0.058 Uiso 0.1207(18) 1 calc R U P A 2
H31D H 0.855912 0.689234 -0.097539 0.058 Uiso 0.1207(18) 1 calc R U P A 2
C32 C 0.9426(3) 0.63290(11) -0.1366(2) 0.0725(7) Uani 1 1 d . . . . .
H32A H 0.979193 0.597552 -0.109338 0.109 Uiso 1 1 calc R U . . .
H32B H 0.997211 0.653307 -0.158866 0.109 Uiso 1 1 calc R U . . .
H32C H 0.864623 0.627132 -0.194049 0.109 Uiso 1 1 calc R U . . .
Cl1 Cl 0.73072(3) 0.55032(2) 0.39403(3) 0.02936(10) Uani 1 1 d . . . . .
O1 O 0.68147(11) 0.53175(4) 0.46654(9) 0.0335(3) Uani 1 1 d . . . . .
O2 O 0.70531(14) 0.50828(5) 0.31600(11) 0.0498(3) Uani 1 1 d . . . . .
O3 O 0.65894(16) 0.59871(5) 0.34312(11) 0.0552(4) Uani 1 1 d . . . . .
Cl2 Cl 0.55943(5) 0.74803(2) -0.16796(3) 0.03205(16) Uani 0.868(2) 1 d . . P B
1
Cl2A Cl 0.6276(4) 0.74337(14) -0.1687(3) 0.0385(11) Uiso 0.132(2) 1 d . . P B 2
O4 O 0.55387(16) 0.68960(5) -0.18182(10) 0.0571(4) Uani 1 1 d . . . . .
O5 O 0.65677(16) 0.76166(6) -0.07223(10) 0.0612(4) Uani 1 1 d . . . . .
O6 O 0.57706(19) 0.77373(7) -0.24902(12) 0.0773(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
N1 C5 1.5179(17) . ?
N1 C13 1.5190(17) . ?
N1 C1 1.5198(17) . ?
N1 C9 1.5200(17) . ?
C1 C2 1.5190(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.536(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.516(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.514(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.522(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5170(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.526(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.513(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.513(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.512(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N2 C17A 1.359(14) . ?
N2 C21 1.504(2) . ?
N2 C25A 1.514(14) . ?
N2 C29 1.5199(19) . ?
N2 C25 1.532(2) . ?
N2 C17 1.541(2) . ?
N2 C29A 1.607(16) . ?
N2 C21A 1.617(12) . ?
C17 C18 1.524(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.534(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.510(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.509(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 C22 1.504(3) . ?
C23 C24 1.508(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 C26 1.521(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.530(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.508(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.511(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.523(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C17A C18A 1.455(19) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A C19A 1.478(19) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A C20A 1.54(2) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C21A C22 1.105(12) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C23A C24 1.138(14) . ?
C23A C22 1.476(14) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
C25A C26A 1.47(2) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26A C27A 1.55(2) . ?
C26A H26C 0.9900 . ?
C26A H26D 0.9900 . ?
C27A C28A 1.51(3) . ?
C27A H27C 0.9900 . ?
C27A H27D 0.9900 . ?
C29A C30A 1.49(3) . ?
C29A H29C 0.9900 . ?
C29A H29D 0.9900 . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 0.9800 . ?
C30A C31 1.32(2) . ?
C30A H30C 0.9900 . ?
C30A H30D 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 H24D 0.9800 . ?
C24 H24E 0.9800 . ?
C24 H24F 0.9800 . ?
C31 C32 1.495(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 H31C 0.9900 . ?
C31 H31D 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
Cl1 O2 1.4684(14) . ?
Cl1 O1 1.4741(11) . ?
Cl1 O3 1.4774(13) . ?
Cl2 O6 1.4239(16) . ?
Cl2 O5 1.4454(14) . ?
Cl2 O4 1.4453(13) . ?
Cl2A O6 1.305(4) . ?
Cl2A O5 1.372(4) . ?
Cl2A O4 1.558(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
C5 N1 C13 110.85(10) . . ?
C5 N1 C1 111.74(10) . . ?
C13 N1 C1 105.57(10) . . ?
C5 N1 C9 105.81(10) . . ?
C13 N1 C9 111.50(10) . . ?
C1 N1 C9 111.48(11) . . ?
C2 C1 N1 115.89(11) . . ?
C2 C1 H1A 108.3 . . ?
N1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
N1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 C3 109.72(12) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 113.70(13) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 115.79(11) . . ?
C6 C5 H5A 108.3 . . ?
N1 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
N1 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C5 C6 C7 109.33(12) . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 C6 111.95(13) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 115.48(11) . . ?
C10 C9 H9A 108.4 . . ?
N1 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
N1 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C11 110.03(12) . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 112.06(13) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 116.04(11) . . ?
C14 C13 H13A 108.3 . . ?
N1 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
N1 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 C15 109.20(12) . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C16 C15 C14 112.68(13) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17A N2 C25A 122.3(8) . . ?
C21 N2 C29 113.01(12) . . ?
C21 N2 C25 108.82(12) . . ?
C29 N2 C25 108.38(11) . . ?
C21 N2 C17 108.95(11) . . ?
C29 N2 C17 107.76(12) . . ?
C25 N2 C17 109.90(12) . . ?
C17A N2 C29A 112.8(8) . . ?
C25A N2 C29A 105.4(8) . . ?
C17A N2 C21A 110.9(8) . . ?
C25A N2 C21A 102.1(7) . . ?
C29A N2 C21A 100.8(7) . . ?
C18 C17 N2 115.34(13) . . ?
C18 C17 H17A 108.4 . . ?
N2 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
N2 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 C19 110.79(15) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C18 114.03(18) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 116.78(14) . . ?
N2 C21 H21A 108.1 . . ?
C22 C21 H21A 108.1 . . ?
N2 C21 H21B 108.1 . . ?
C22 C21 H21B 108.1 . . ?
H21A C21 H21B 107.3 . . ?
C22 C23 C24 114.53(18) . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C26 C25 N2 115.57(13) . . ?
C26 C25 H25A 108.4 . . ?
N2 C25 H25A 108.4 . . ?
C26 C25 H25B 108.4 . . ?
N2 C25 H25B 108.4 . . ?
H25A C25 H25B 107.4 . . ?
C25 C26 C27 110.70(15) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C26 114.81(18) . . ?
C28 C27 H27A 108.6 . . ?
C26 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 N2 115.57(14) . . ?
C30 C29 H29A 108.4 . . ?
N2 C29 H29A 108.4 . . ?
C30 C29 H29B 108.4 . . ?
N2 C29 H29B 108.4 . . ?
H29A C29 H29B 107.4 . . ?
C29 C30 C31 110.21(16) . . ?
C29 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
C29 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
N2 C17A C18A 115.8(11) . . ?
N2 C17A H17C 108.3 . . ?
C18A C17A H17C 108.3 . . ?
N2 C17A H17D 108.3 . . ?
C18A C17A H17D 108.3 . . ?
H17C C17A H17D 107.4 . . ?
C17A C18A C19A 111.7(12) . . ?
C17A C18A H18C 109.3 . . ?
C19A C18A H18C 109.3 . . ?
C17A C18A H18D 109.3 . . ?
C19A C18A H18D 109.3 . . ?
H18C C18A H18D 107.9 . . ?
C18A C19A C20A 116.2(13) . . ?
C18A C19A H19C 108.2 . . ?
C20A C19A H19C 108.2 . . ?
C18A C19A H19D 108.2 . . ?
C20A C19A H19D 108.2 . . ?
H19C C19A H19D 107.4 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C22 C21A N2 140.2(10) . . ?
C22 C21A H21C 102.0 . . ?
N2 C21A H21C 102.0 . . ?
C22 C21A H21D 102.0 . . ?
N2 C21A H21D 102.0 . . ?
H21C C21A H21D 104.8 . . ?
C24 C23A C22 151.4(13) . . ?
C24 C23A H23C 98.8 . . ?
C22 C23A H23C 98.8 . . ?
C24 C23A H23D 98.8 . . ?
C22 C23A H23D 98.8 . . ?
H23C C23A H23D 103.9 . . ?
C26A C25A N2 110.2(11) . . ?
C26A C25A H25C 109.6 . . ?
N2 C25A H25C 109.6 . . ?
C26A C25A H25D 109.6 . . ?
N2 C25A H25D 109.6 . . ?
H25C C25A H25D 108.1 . . ?
C25A C26A C27A 110.0(13) . . ?
C25A C26A H26C 109.7 . . ?
C27A C26A H26C 109.7 . . ?
C25A C26A H26D 109.7 . . ?
C27A C26A H26D 109.7 . . ?
H26C C26A H26D 108.2 . . ?
C28A C27A C26A 114.6(15) . . ?
C28A C27A H27C 108.6 . . ?
C26A C27A H27C 108.6 . . ?
C28A C27A H27D 108.6 . . ?
C26A C27A H27D 108.6 . . ?
H27C C27A H27D 107.6 . . ?
C30A C29A N2 118.2(14) . . ?
C30A C29A H29C 107.8 . . ?
N2 C29A H29C 107.8 . . ?
C30A C29A H29D 107.8 . . ?
N2 C29A H29D 107.8 . . ?
H29C C29A H29D 107.1 . . ?
C27A C28A H28D 109.5 . . ?
C27A C28A H28E 109.5 . . ?
H28D C28A H28E 109.5 . . ?
C27A C28A H28F 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
C31 C30A C29A 122.9(17) . . ?
C31 C30A H30C 106.6 . . ?
C29A C30A H30C 106.6 . . ?
C31 C30A H30D 106.6 . . ?
C29A C30A H30D 106.6 . . ?
H30C C30A H30D 106.6 . . ?
C21A C22 C23A 150.2(9) . . ?
C23 C22 C21 111.14(15) . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C21A C22 H22C 99.1 . . ?
C23A C22 H22C 99.1 . . ?
C21A C22 H22D 99.1 . . ?
C23A C22 H22D 99.1 . . ?
H22C C22 H22D 104.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23A C24 H24D 109.5 . . ?
C23A C24 H24E 109.5 . . ?
H24D C24 H24E 109.5 . . ?
C23A C24 H24F 109.5 . . ?
H24D C24 H24F 109.5 . . ?
H24E C24 H24F 109.5 . . ?
C30A C31 C32 142.1(10) . . ?
C32 C31 C30 112.20(19) . . ?
C32 C31 H31A 109.2 . . ?
C30 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
C30 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C30A C31 H31C 101.5 . . ?
C32 C31 H31C 101.5 . . ?
C30A C31 H31D 101.5 . . ?
C32 C31 H31D 101.5 . . ?
H31C C31 H31D 104.6 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O2 Cl1 O1 108.31(7) . . ?
O2 Cl1 O3 106.46(9) . . ?
O1 Cl1 O3 106.34(7) . . ?
O6 Cl2 O5 110.80(10) . . ?
O6 Cl2 O4 109.79(10) . . ?
O5 Cl2 O4 109.67(9) . . ?
O6 Cl2A O5 123.8(3) . . ?
O6 Cl2A O4 109.8(3) . . ?
O5 Cl2A O4 107.3(2) . . ?

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
C5 N1 C1 C2 53.54(15) . . . . ?
C13 N1 C1 C2 174.12(12) . . . . ?
C9 N1 C1 C2 -64.64(15) . . . . ?
N1 C1 C2 C3 177.22(12) . . . . ?
C1 C2 C3 C4 -73.87(17) . . . . ?
C13 N1 C5 C6 -59.55(15) . . . . ?
C1 N1 C5 C6 57.91(15) . . . . ?
C9 N1 C5 C6 179.42(12) . . . . ?
N1 C5 C6 C7 -173.33(12) . . . . ?
C5 C6 C7 C8 176.90(14) . . . . ?
C5 N1 C9 C10 -176.46(12) . . . . ?
C13 N1 C9 C10 62.94(15) . . . . ?
C1 N1 C9 C10 -54.77(15) . . . . ?
N1 C9 C10 C11 -161.71(12) . . . . ?
C9 C10 C11 C12 -176.70(14) . . . . ?
C5 N1 C13 C14 -64.63(15) . . . . ?
C1 N1 C13 C14 174.20(12) . . . . ?
C9 N1 C13 C14 52.97(16) . . . . ?
N1 C13 C14 C15 172.76(12) . . . . ?
C13 C14 C15 C16 173.51(15) . . . . ?
C21 N2 C17 C18 -176.17(14) . . . . ?
C29 N2 C17 C18 60.87(18) . . . . ?
C25 N2 C17 C18 -57.03(17) . . . . ?
N2 C17 C18 C19 174.94(15) . . . . ?
C17 C18 C19 C20 -70.9(2) . . . . ?
C29 N2 C21 C22 53.10(18) . . . . ?
C25 N2 C21 C22 173.54(14) . . . . ?
C17 N2 C21 C22 -66.65(17) . . . . ?
C21 N2 C25 C26 65.25(18) . . . . ?
C29 N2 C25 C26 -171.49(15) . . . . ?
C17 N2 C25 C26 -53.97(18) . . . . ?
N2 C25 C26 C27 179.30(15) . . . . ?
C25 C26 C27 C28 65.1(2) . . . . ?
C21 N2 C29 C30 50.64(19) . . . . ?
C25 N2 C29 C30 -70.05(18) . . . . ?
C17 N2 C29 C30 171.07(14) . . . . ?
N2 C29 C30 C31 177.69(15) . . . . ?
C25A N2 C17A C18A 50.3(15) . . . . ?
C29A N2 C17A C18A 177.6(11) . . . . ?
C21A N2 C17A C18A -70.2(13) . . . . ?
N2 C17A C18A C19A -174.6(11) . . . . ?
C17A C18A C19A C20A 175.0(13) . . . . ?
C17A N2 C21A C22 -166.8(15) . . . . ?
C25A N2 C21A C22 61.4(17) . . . . ?
C29A N2 C21A C22 -47.2(17) . . . . ?
C17A N2 C25A C26A 53.1(15) . . . . ?
C29A N2 C25A C26A -77.4(13) . . . . ?
C21A N2 C25A C26A 177.6(11) . . . . ?
N2 C25A C26A C27A -176.5(11) . . . . ?
C25A C26A C27A C28A 179.3(16) . . . . ?
C17A N2 C29A C30A 53.7(17) . . . . ?
C25A N2 C29A C30A -170.4(14) . . . . ?
C21A N2 C29A C30A -64.5(15) . . . . ?
N2 C29A C30A C31 -165.7(14) . . . . ?
N2 C21A C22 C23A -163.9(13) . . . . ?
C24 C23A C22 C21A -161(2) . . . . ?
C24 C23 C22 C21 -179.56(17) . . . . ?
N2 C21 C22 C23 -174.15(14) . . . . ?
C29A C30A C31 C32 -63(2) . . . . ?
C29 C30 C31 C32 176.22(19) . . . . ?

_refine_diff_density_max         0.703
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.044

