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

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

data_paradiquat
_database_code_depnum_ccdc_archive 'CCDC 1896282'
loop_
_audit_author_name
_audit_author_address
'John Bacsa'
;Emory University
United States of America
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.05.03 svn.r3294 for OlexSys, GUI svn.r5176)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), C15 H18 N2, H2 O'
_chemical_formula_sum            'C15 H20 Br2 N2 O'
_chemical_formula_weight         404.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1474(10)
_cell_length_b                   14.4208(12)
_cell_length_c                   11.2139(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.1500(10)
_cell_angle_gamma                90
_cell_volume                     1644.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.615
_cell_measurement_theta_min      2.441
_shelx_estimated_absorpt_T_max   0.326
_shelx_estimated_absorpt_T_min   0.294
_exptl_absorpt_coefficient_mu    4.926
_exptl_absorpt_correction_T_max  0.3881
_exptl_absorpt_correction_T_min  0.2508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.6462.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method 'Slow evaporation from ethanol'
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.293
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21850
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.614
_diffrn_reflns_theta_min         2.002
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4201
_reflns_number_total             5049
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2015)'
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         5049
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.7003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0903
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H1WB-O1W = O1W-H1WA
 0.995 with sigma of 0.005
 H1WB-H1WA
 1.579 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), C13(H13), C6(H6), C9(H9), C12(H12)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 1.02924(2) 0.57477(2) 0.76976(2) 0.01726(7) Uani 1 1 d . . . . .
Br1 Br 0.49134(2) 0.68967(2) 0.49830(2) 0.01868(7) Uani 1 1 d . . . . .
N1 N 0.41352(18) 0.47243(14) 0.79009(18) 0.0133(4) Uani 1 1 d . . . . .
N2 N 0.23862(17) 0.57283(13) 0.54709(18) 0.0123(4) Uani 1 1 d . . . . .
O1W O 0.8031(2) 0.73389(15) 0.7041(2) 0.0371(5) Uani 1 1 d D . . . .
H1WA H 0.7148(13) 0.710(2) 0.647(3) 0.056 Uiso 1 1 d DR . . . .
C10 C 0.2778(2) 0.69818(15) 0.6953(2) 0.0132(4) Uani 1 1 d . . . . .
H10 H 0.3292 0.7255 0.7776 0.016 Uiso 1 1 calc R . . . .
C11 C 0.1684(2) 0.74541(16) 0.6055(2) 0.0137(4) Uani 1 1 d . . . . .
C4 C 0.3108(2) 0.61244(16) 0.6646(2) 0.0123(4) Uani 1 1 d . . . . .
C5 C 0.4275(2) 0.56188(16) 0.7588(2) 0.0121(4) Uani 1 1 d . . . . .
C8 C 0.6390(2) 0.46580(18) 0.9353(2) 0.0185(5) Uani 1 1 d . . . . .
H8 H 0.7108 0.4316 0.9960 0.022 Uiso 1 1 calc R . . . .
C13 C 0.1330(2) 0.61701(17) 0.4587(2) 0.0148(4) Uani 1 1 d . . . . .
H13 H 0.0828 0.5883 0.3772 0.018 Uiso 1 1 calc R . . . .
C6 C 0.5479(2) 0.60482(17) 0.8167(2) 0.0142(4) Uani 1 1 d . . . . .
H6 H 0.5568 0.6675 0.7956 0.017 Uiso 1 1 calc R . . . .
C1 C 0.2818(2) 0.42769(16) 0.7301(2) 0.0156(4) Uani 1 1 d . . . . .
H1A H 0.2147 0.4703 0.7359 0.019 Uiso 1 1 calc R . . . .
H1B H 0.2819 0.3705 0.7790 0.019 Uiso 1 1 calc R . . . .
C7 C 0.6573(2) 0.55762(18) 0.9062(2) 0.0159(4) Uani 1 1 d . . . . .
C9 C 0.5170(2) 0.42465(17) 0.8761(2) 0.0169(4) Uani 1 1 d . . . . .
H9 H 0.5056 0.3621 0.8960 0.020 Uiso 1 1 calc R . . . .
C3 C 0.2793(2) 0.48156(16) 0.5137(2) 0.0147(4) Uani 1 1 d . . . . .
H3A H 0.3750 0.4820 0.5368 0.018 Uiso 1 1 calc R . . . .
H3B H 0.2333 0.4707 0.4185 0.018 Uiso 1 1 calc R . . . .
C12 C 0.0970(2) 0.70322(17) 0.4854(2) 0.0165(4) Uani 1 1 d . . . . .
H12 H 0.0233 0.7340 0.4218 0.020 Uiso 1 1 calc R . . . .
C2 C 0.2465(2) 0.40356(17) 0.5874(2) 0.0168(4) Uani 1 1 d . . . . .
H2A H 0.1513 0.3898 0.5440 0.020 Uiso 1 1 calc R . . . .
H2B H 0.2948 0.3469 0.5832 0.020 Uiso 1 1 calc R . . . .
C15 C 0.1269(2) 0.83706(18) 0.6397(2) 0.0192(5) Uani 1 1 d . . . . .
H15A H 0.0518 0.8279 0.6625 0.029 Uiso 1 1 calc GR . . . .
H15B H 0.1018 0.8790 0.5646 0.029 Uiso 1 1 calc GR . . . .
H15C H 0.2001 0.8642 0.7143 0.029 Uiso 1 1 calc GR . . . .
C14 C 0.7891(2) 0.6030(2) 0.9664(2) 0.0244(5) Uani 1 1 d . . . . .
H14A H 0.8480 0.5653 1.0398 0.037 Uiso 1 1 calc GR . . . .
H14B H 0.7800 0.6648 0.9981 0.037 Uiso 1 1 calc GR . . . .
H14C H 0.8259 0.6086 0.9009 0.037 Uiso 1 1 calc GR . . . .
H1WB H 0.864(2) 0.6819(16) 0.713(4) 0.060(12) Uiso 1 1 d 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 1.362(3) . ?
N1 C1 1.489(3) . ?
N1 C9 1.351(3) . ?
N2 C4 1.358(3) . ?
N2 C13 1.349(3) . ?
N2 C3 1.489(3) . ?
O1W H1WA 0.991(5) . ?
O1W H1WB 0.992(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.400(3) . ?
C10 C4 1.373(3) . ?
C11 C12 1.393(3) . ?
C11 C15 1.501(3) . ?
C4 C5 1.489(3) . ?
C5 C6 1.376(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.399(4) . ?
C8 C9 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.376(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.523(3) . ?
C7 C14 1.494(3) . ?
C9 H9 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.526(3) . ?
C12 H12 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 119.32(18) . . ?
C9 N1 C5 120.83(19) . . ?
C9 N1 C1 119.8(2) . . ?
C4 N2 C3 119.71(18) . . ?
C13 N2 C4 120.4(2) . . ?
C13 N2 C3 119.80(19) . . ?
H1WA O1W H1WB 105.1(10) . . ?
C11 C10 H10 119.9 . . ?
C4 C10 H10 120.0 . . ?
C4 C10 C11 120.1(2) . . ?
C10 C11 C15 120.9(2) . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 C15 121.2(2) . . ?
N2 C4 C10 120.59(19) . . ?
N2 C4 C5 118.8(2) . . ?
C10 C4 C5 120.61(19) . . ?
N1 C5 C4 119.18(19) . . ?
N1 C5 C6 119.8(2) . . ?
C6 C5 C4 121.0(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.3(2) . . ?
N2 C13 H13 119.6 . . ?
N2 C13 C12 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.90(18) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C8 C7 C6 117.4(2) . . ?
C8 C7 C14 121.3(2) . . ?
C6 C7 C14 121.3(2) . . ?
N1 C9 C8 120.6(2) . . ?
N1 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 C2 110.52(18) . . ?
H3A C3 H3B 108.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C1 C2 C3 112.60(19) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA Br1 0.991(5) 2.382(9) 3.354(2) 167(3) .
O1W H1WB Br2 0.992(5) 2.283(8) 3.263(2) 169(3) .

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
N1 C5 C6 C7 0.9(3) . . . . ?
N1 C1 C2 C3 -43.8(3) . . . . ?
N2 C4 C5 N1 -52.3(3) . . . . ?
N2 C4 C5 C6 129.3(2) . . . . ?
N2 C13 C12 C11 -1.1(3) . . . . ?
N2 C3 C2 C1 -43.6(2) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C10 C4 C5 N1 128.6(2) . . . . ?
C10 C4 C5 C6 -49.8(3) . . . . ?
C11 C10 C4 N2 0.4(3) . . . . ?
C11 C10 C4 C5 179.5(2) . . . . ?
C4 N2 C13 C12 0.6(3) . . . . ?
C4 N2 C3 C2 74.9(2) . . . . ?
C4 C10 C11 C12 -0.8(3) . . . . ?
C4 C10 C11 C15 177.0(2) . . . . ?
C4 C5 C6 C7 179.4(2) . . . . ?
C5 N1 C1 C2 74.3(3) . . . . ?
C5 N1 C9 C8 0.7(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C5 C6 C7 C14 178.2(2) . . . . ?
C13 N2 C4 C10 -0.2(3) . . . . ?
C13 N2 C4 C5 -179.3(2) . . . . ?
C13 N2 C3 C2 -107.3(2) . . . . ?
C1 N1 C5 C4 -0.4(3) . . . . ?
C1 N1 C5 C6 178.0(2) . . . . ?
C1 N1 C9 C8 -178.3(2) . . . . ?
C7 C8 C9 N1 -0.4(4) . . . . ?
C9 N1 C5 C4 -179.4(2) . . . . ?
C9 N1 C5 C6 -0.9(3) . . . . ?
C9 N1 C1 C2 -106.8(2) . . . . ?
C9 C8 C7 C6 0.4(3) . . . . ?
C9 C8 C7 C14 -178.5(2) . . . . ?
C3 N2 C4 C10 177.5(2) . . . . ?
C3 N2 C4 C5 -1.6(3) . . . . ?
C3 N2 C13 C12 -177.2(2) . . . . ?
C15 C11 C12 C13 -176.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id paradiquat
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dq52
_database_code_depnum_ccdc_archive 'CCDC 1896283'
loop_
_audit_author_name
_audit_author_address
'John Bacsa'
;Emory University
United States of America
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;
_audit_creation_date             2019-02-08
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), C H4 O, C14 H16 N2'
_chemical_formula_sum            'C15 H20 Br2 N2 O'
_chemical_formula_weight         404.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30  H40  Br4  N4  O2  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3138(2)
_cell_length_b                   10.0105(3)
_cell_length_c                   12.1578(2)
_cell_angle_alpha                104.745(2)
_cell_angle_beta                 96.597(2)
_cell_angle_gamma                103.047(3)
_cell_volume                     824.44(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8364
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8750
_cell_measurement_theta_min      3.8070
_shelx_estimated_absorpt_T_max   0.396
_shelx_estimated_absorpt_T_min   0.295
_exptl_absorpt_coefficient_mu    6.213
_exptl_absorpt_correction_T_max  0.584
_exptl_absorpt_correction_T_min  0.350
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0862
1 0 0 0.0964
1 0 -1 0.1011
-1 0 1 0.1163
0 0 -1 0.1085
0 -1 2 0.1432
0 1 -2 0.1337
2 -1 0 0.1048
-2 1 -2 0.1151
-2 1 0 0.0988
2 -1 -2 0.0924
-2 1 2 0.1155
1 -2 -2 0.1081
-1 2 2 0.1226
1 -1 2 0.1230
1 2 0 0.0980
1 -2 7 0.1136
4 3 -4 0.0990
0 -1 8 0.1015
0 1 -8 0.1065
4 -4 0 0.1085
-4 4 1 0.1030
-4 4 3 0.1009
3 -3 -6 0.0903
4 -4 -2 0.0938
2 -6 -1 0.1091
-2 6 0 0.1105
0 3 6 0.1089
-1 -1 -6 0.1079
0 6 -1 0.0973
0 -6 0 0.1165
-2 0 -6 0.1012
2 -1 7 0.1088
-4 -1 0 0.0921
4 1 0 0.0928

_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.183
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9989 -0.0014 -0.0028 -0.1681 0.0906 0.1089
0.9989 0.0014 0.0028 0.1681 -0.0906 -0.1089
0.9990 0.0014 -0.9964 0.2164 -0.0905 0.0152
-0.9990 -0.0014 0.9964 -0.2164 0.0905 -0.0152
0.0000 0.0000 -0.9992 0.0483 0.0001 0.1241
0.0004 -0.9995 1.9972 -0.0494 0.1545 -0.2152
-0.0004 0.9995 -1.9972 0.0494 -0.1545 0.2152
1.9984 -0.9967 0.0045 0.3834 -0.0265 -0.1849
-1.9983 0.9967 -2.0029 -0.2868 0.0267 0.4331
-1.9984 0.9967 -0.0045 -0.3834 0.0265 0.1849
1.9985 -0.9966 -1.9940 0.4800 -0.0264 0.0633
-1.9985 0.9966 1.9940 -0.4800 0.0264 -0.0633
1.0000 -1.9974 -1.9980 0.3591 0.2188 0.2053
-1.0000 1.9974 1.9980 -0.3591 -0.2188 -0.2053
0.9994 -0.9981 2.0000 0.1187 0.0639 -0.3242
0.9979 2.0002 0.0052 0.0737 -0.3998 -0.1749
1.3213 -1.6320 7.2460 -0.0506 0.1325 -0.9899
3.5335 2.8438 -3.9175 0.6506 -0.7593 0.0091
-0.1095 -1.0319 7.7974 -0.3466 0.1690 -0.9227
0.1967 1.0286 -7.8132 0.3622 -0.1764 0.9153
4.4128 -3.6981 0.0176 0.9168 0.1731 -0.3599
-4.3831 3.7138 0.6887 -0.9467 -0.1783 0.2685
-4.0343 3.5438 2.8146 -0.9826 -0.1837 -0.0279
2.8076 -2.6729 -5.5476 0.8670 0.1601 0.4720
4.2204 -3.6517 -1.9793 0.9787 0.1835 -0.0925
1.6674 -6.0727 -0.7652 0.6039 0.7889 0.1137
-1.7947 6.1771 0.2840 -0.6070 -0.7935 -0.0436
0.2522 2.8494 5.5419 -0.3595 -0.4641 -0.8095
-0.9209 -1.2108 -6.4315 0.2126 0.2711 0.9388
0.0430 6.2471 -1.1464 -0.2316 -0.9704 -0.0679
-0.2728 -5.9923 0.1751 0.2278 0.9519 0.2051
-1.6181 -0.2891 -6.3993 0.0502 0.1916 0.9802
1.6576 -0.5964 6.7438 -0.0185 -0.0582 -0.9981
-4.1332 -1.4296 -0.0651 -0.6259 0.5950 0.5042
4.1448 1.4836 -0.1555 0.6359 -0.6044 -0.4798

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9300
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.039
_diffrn_reflns_theta_min         3.824
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     82.00 119.00   0.50    1.00    --  105.75-125.00-120.00   74
  2  ω     86.00 117.00   0.50    1.00    --  105.75-125.00  90.00   62
  3  ω     62.00 106.00   0.50    1.00    --  105.75-125.00  60.00   88
  4  ω     35.00  73.00   0.50    1.00    --  105.75-125.00  90.00   76
  5  ω     39.00  74.00   0.50    1.00    --  105.75-125.00-120.00   70
  6  ω   -104.00 -70.00   0.50    0.25    --  -49.66-125.00 -60.00   68
  7  ω   -120.00 -73.00   0.50    0.25    --  -49.66-125.00  60.00   94
  8  ω     81.00 107.00   0.50    1.00    --  105.75 -95.00 -60.00   52
  9  ω     65.00 108.00   0.50    1.00    --  105.75 -95.00 150.00   86
 10  ω     35.00  61.00   0.50    1.00    --  105.75 -95.00 -60.00   52
 11  ω     38.00  76.00   0.50    1.00    --  105.75 -77.00  60.00   76
 12  ω     69.00 100.00   0.50    1.00    --  105.75 -77.00 120.00   62
 13  ω     38.00  88.00   0.50    1.00    --  105.75 -77.00  90.00  100
 14  ω     35.00  62.00   0.50    1.00    --  105.75 -77.00 120.00   54
 15  ω     52.00  77.00   0.50    1.00    --  105.75 -45.00 -60.00   50
 16  ω     34.00  83.00   0.50    1.00    --  105.75 -45.00 -30.00   98
 17  ω     34.00  84.00   0.50    1.00    --  105.75 -45.00-180.00  100
 18  ω     37.00  64.00   0.50    1.00    --  105.75 -28.00  98.00   54
 19  ω     11.00  37.00   0.50    0.25    --   49.66 -28.00  98.00   52
 20  ω   -111.00 -45.00   0.50    0.25    --  -49.66 -28.00  98.00  132
 21  ω   -158.00 -81.00   0.50    1.00    --  -84.25 -28.00  98.00  154
 22  ω    -20.00  54.00   0.50    0.25    --   49.66 -19.00 -60.00  148
 23  ω     98.00 178.00   0.50    1.00    --  105.75  28.00 -99.00  160
 24  ω     68.00 118.00   0.50    0.25    --   49.66  28.00 -99.00  100
 25  ω    -10.00  19.00   0.50    0.25    --  -49.66  28.00 -99.00   58
 26  ω    -56.00 -15.00   0.50    0.25    --  -49.66  28.00 -99.00   82
 27  ω    -70.00 -37.00   0.50    1.00    --  -84.25  28.00 -99.00   66
 28  ω    102.00 176.00   0.50    1.00    --  105.75  30.00 -30.00  148
 29  ω     99.00 176.00   0.50    1.00    --  105.75  30.00   0.00  154
 30  ω    137.00 175.00   0.50    1.00    --  105.75 125.00  60.00   76
 31  ω    150.00 175.00   0.50    1.00    --  105.75 125.00  30.00   50
 32  ω    106.00 139.00   0.50    1.00    --  105.75 125.00  30.00   66
 33  ω     94.00 126.00   0.50    1.00    --  105.75 125.00  60.00   64
 34  ω    -58.00 -25.00   0.50    1.00    --  -84.25 125.00   0.00   66
 35  ω    -91.00 -35.00   0.50    1.00    --  -84.25 125.00 -90.00  112
 36  ω    -91.00 -64.00   0.50    1.00    --  -84.25 125.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1684762000
_diffrn_orient_matrix_UB_12      -0.0470997000
_diffrn_orient_matrix_UB_13      -0.0483181000
_diffrn_orient_matrix_UB_21      -0.0904463000
_diffrn_orient_matrix_UB_22      -0.1547328000
_diffrn_orient_matrix_UB_23      -0.0000758000
_diffrn_orient_matrix_UB_31      -0.1086510000
_diffrn_orient_matrix_UB_32      -0.0329092000
_diffrn_orient_matrix_UB_33      -0.1242112000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3210
_reflns_number_total             3321
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.7799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0800
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O1-H1
 0.955 with sigma of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C7(H7), C10(H10), C5(H5), C12(H12)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.10010(3) 0.22863(2) 0.64365(2) 0.01977(11) Uani 1 1 d . . . . .
Br2 Br 0.51816(3) 0.85555(2) 0.77817(2) 0.01984(11) Uani 1 1 d . . . . .
O1 O 0.1428(3) 0.2333(2) 0.88695(16) 0.0302(4) Uani 1 1 d D . . . .
N2 N 0.3072(3) 0.2484(2) 0.51005(16) 0.0156(4) Uani 1 1 d . . . . .
N1 N 0.4600(3) 0.2456(2) 0.73257(16) 0.0150(4) Uani 1 1 d . . . . .
C9 C 0.3055(3) 0.4905(2) 0.5805(2) 0.0159(4) Uani 1 1 d . . . . .
H9 H 0.339050 0.576414 0.639514 0.019 Uiso 1 1 calc R . . . .
C6 C 0.6555(3) 0.3626(3) 0.9173(2) 0.0187(5) Uani 1 1 d . . . . .
C8 C 0.5545(3) 0.4985(3) 0.7953(2) 0.0177(4) Uani 1 1 d . . . . .
H8 H 0.553774 0.586309 0.782795 0.021 Uiso 1 1 calc R . . . .
C1 C 0.4589(3) 0.3725(2) 0.71085(19) 0.0147(4) Uani 1 1 d . . . . .
C7 C 0.6516(3) 0.4937(3) 0.8988(2) 0.0187(5) Uani 1 1 d . . . . .
H7 H 0.714315 0.578526 0.955957 0.022 Uiso 1 1 calc R . . . .
C2 C 0.3550(3) 0.3712(2) 0.59903(19) 0.0152(4) Uani 1 1 d . . . . .
C4 C 0.3767(3) 0.1257(2) 0.52668(19) 0.0176(4) Uani 1 1 d . . . . .
H4A H 0.510561 0.141641 0.520800 0.021 Uiso 1 1 calc R . . . .
H4B H 0.305412 0.038489 0.467393 0.021 Uiso 1 1 calc R . . . .
C3 C 0.3503(3) 0.1112(2) 0.6443(2) 0.0185(5) Uani 1 1 d . . . . .
H3A H 0.216091 0.093054 0.649583 0.022 Uiso 1 1 calc R . . . .
H3B H 0.395280 0.031367 0.657163 0.022 Uiso 1 1 calc R . . . .
C10 C 0.2048(3) 0.4806(3) 0.4726(2) 0.0182(5) Uani 1 1 d . . . . .
H10 H 0.176112 0.561509 0.458957 0.022 Uiso 1 1 calc R . . . .
C5 C 0.5553(3) 0.2395(3) 0.8315(2) 0.0182(5) Uani 1 1 d . . . . .
H5 H 0.553871 0.150683 0.842423 0.022 Uiso 1 1 calc R . . . .
C12 C 0.2039(3) 0.2359(3) 0.4076(2) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.169758 0.148399 0.350426 0.021 Uiso 1 1 calc R . . . .
C11 C 0.1470(3) 0.3514(3) 0.3854(2) 0.0186(5) Uani 1 1 d . . . . .
C14 C 0.0297(4) 0.3327(3) 0.2707(2) 0.0232(5) Uani 1 1 d . . . . .
H14A H -0.099791 0.282198 0.267958 0.035 Uiso 1 1 calc GR . . . .
H14B H 0.080698 0.278986 0.210187 0.035 Uiso 1 1 calc GR . . . .
H14C H 0.032786 0.425035 0.260176 0.035 Uiso 1 1 calc GR . . . .
C13 C 0.7659(4) 0.3526(3) 1.0262(2) 0.0247(5) Uani 1 1 d . . . . .
H13A H 0.872105 0.315123 1.008164 0.037 Uiso 1 1 calc GR . . . .
H13B H 0.683928 0.290077 1.059004 0.037 Uiso 1 1 calc GR . . . .
H13C H 0.811777 0.446148 1.080903 0.037 Uiso 1 1 calc GR . . . .
C16 C 0.1043(5) 0.0931(4) 0.9008(3) 0.0398(7) Uani 1 1 d . . . . .
H16A H 0.145810 0.030976 0.840415 0.060 Uiso 1 1 calc GR . . . .
H16B H -0.030365 0.057040 0.896567 0.060 Uiso 1 1 calc GR . . . .
H16C H 0.171461 0.096906 0.974591 0.060 Uiso 1 1 calc GR . . . .
H1 H 0.068(5) 0.227(5) 0.8154(19) 0.060 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.424(4) . ?
O1 H1 0.954(5) . ?
N2 C2 1.358(3) . ?
N2 C4 1.481(3) . ?
N2 C12 1.341(3) . ?
N1 C1 1.363(3) . ?
N1 C3 1.478(3) . ?
N1 C5 1.341(3) . ?
C9 H9 0.9300 . ?
C9 C2 1.386(3) . ?
C9 C10 1.398(3) . ?
C6 C7 1.393(3) . ?
C6 C5 1.381(3) . ?
C6 C13 1.508(3) . ?
C8 H8 0.9300 . ?
C8 C1 1.383(3) . ?
C8 C7 1.390(3) . ?
C1 C2 1.474(3) . ?
C7 H7 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.503(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C11 1.388(4) . ?
C5 H5 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.390(3) . ?
C11 C14 1.496(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 H1 107(3) . . ?
C2 N2 C4 118.29(19) . . ?
C12 N2 C2 122.5(2) . . ?
C12 N2 C4 119.22(19) . . ?
C1 N1 C3 118.47(19) . . ?
C5 N1 C1 122.1(2) . . ?
C5 N1 C3 119.45(19) . . ?
C2 C9 H9 120.3 . . ?
C2 C9 C10 119.5(2) . . ?
C10 C9 H9 120.3 . . ?
C7 C6 C13 122.1(2) . . ?
C5 C6 C7 117.8(2) . . ?
C5 C6 C13 120.1(2) . . ?
C1 C8 H8 120.1 . . ?
C1 C8 C7 119.9(2) . . ?
C7 C8 H8 120.1 . . ?
N1 C1 C8 118.6(2) . . ?
N1 C1 C2 119.2(2) . . ?
C8 C1 C2 122.2(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
N2 C2 C9 118.5(2) . . ?
N2 C2 C1 118.7(2) . . ?
C9 C2 C1 122.7(2) . . ?
N2 C4 H4A 110.0 . . ?
N2 C4 H4B 110.0 . . ?
N2 C4 C3 108.55(18) . . ?
H4A C4 H4B 108.4 . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
N1 C3 C4 108.67(19) . . ?
N1 C3 H3A 110.0 . . ?
N1 C3 H3B 110.0 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
N1 C5 C6 121.3(2) . . ?
N1 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
N2 C12 H12 119.4 . . ?
N2 C12 C11 121.2(2) . . ?
C11 C12 H12 119.4 . . ?
C10 C11 C12 117.3(2) . . ?
C10 C11 C14 123.0(2) . . ?
C12 C11 C14 119.7(2) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9 Br2 0.93 2.79 3.695(2) 163.4 . yes
C8 H8 Br2 0.93 2.78 3.699(2) 169.9 . yes
C4 H4B Br1 0.97 2.67 3.608(2) 163.7 2_556 yes
C5 H5 Br2 0.93 2.80 3.672(2) 156.8 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C4 C3 N1 -59.5(2) . . . . ?
N2 C12 C11 C10 1.3(3) . . . . ?
N2 C12 C11 C14 -179.2(2) . . . . ?
N1 C1 C2 N2 -17.3(3) . . . . ?
N1 C1 C2 C9 163.3(2) . . . . ?
C9 C10 C11 C12 -4.0(3) . . . . ?
C9 C10 C11 C14 176.5(2) . . . . ?
C8 C1 C2 N2 163.2(2) . . . . ?
C8 C1 C2 C9 -16.2(3) . . . . ?
C1 N1 C3 C4 40.7(3) . . . . ?
C1 N1 C5 C6 0.9(3) . . . . ?
C1 C8 C7 C6 0.9(4) . . . . ?
C7 C6 C5 N1 1.1(4) . . . . ?
C7 C8 C1 N1 1.1(3) . . . . ?
C7 C8 C1 C2 -179.4(2) . . . . ?
C2 N2 C4 C3 43.7(3) . . . . ?
C2 N2 C12 C11 2.9(3) . . . . ?
C2 C9 C10 C11 2.7(3) . . . . ?
C4 N2 C2 C9 174.1(2) . . . . ?
C4 N2 C2 C1 -5.3(3) . . . . ?
C4 N2 C12 C11 -175.5(2) . . . . ?
C3 N1 C1 C8 177.2(2) . . . . ?
C3 N1 C1 C2 -2.3(3) . . . . ?
C3 N1 C5 C6 -178.4(2) . . . . ?
C10 C9 C2 N2 1.4(3) . . . . ?
C10 C9 C2 C1 -179.2(2) . . . . ?
C5 N1 C1 C8 -2.0(3) . . . . ?
C5 N1 C1 C2 178.5(2) . . . . ?
C5 N1 C3 C4 -140.1(2) . . . . ?
C5 C6 C7 C8 -2.0(3) . . . . ?
C12 N2 C2 C9 -4.2(3) . . . . ?
C12 N2 C2 C1 176.3(2) . . . . ?
C12 N2 C4 C3 -137.9(2) . . . . ?
C13 C6 C7 C8 177.4(2) . . . . ?
C13 C6 C5 N1 -178.3(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id DQ52
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.742
####################################################################### 
# 
# 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_mk-5-10-2016
_database_code_depnum_ccdc_archive 'CCDC 1896286'
loop_
_audit_author_name
_audit_author_address
'John Bacsa'
;Emory University
United States of America
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_mk-5-10-2016        
;
PROBLEM: D-H Without Acceptor O2B --H2BB . Please Check
RESPONSE: This donor is from a disordered water 
with 50% occupancy.
One of the hydrogen bond acceptors could be located
but the second is uncertain.

;
# end Validation Reply Form

_audit_creation_date             2019-02-08
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 N2, 2(Br), 4(H2 O)'
_chemical_formula_sum            'C15 H26 Br2 N2 O4'
_chemical_formula_weight         458.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C120  H192  Br16  N16  O24  '
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   21.061(2)
_cell_length_b                   6.7995(7)
_cell_length_c                   26.557(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.682(12)
_cell_angle_gamma                90
_cell_volume                     3790.4(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20087
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      3.079
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.297
_exptl_absorpt_correction_T_max  0.13186
_exptl_absorpt_correction_T_min  0.10037
_exptl_absorpt_correction_type   sphere
_exptl_crystal_size_rad          0.4
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.15a (Rigaku Oxford Diffraction, 2018) Spherical absorption correction using equivalent radius and absorption coefficient. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1856
_exptl_crystal_recrystallization_method 'Evaporation from water'
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.391
_exptl_crystal_size_min          0.144
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            24618
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.541
_diffrn_reflns_theta_min         1.539
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.495
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.76 200.24   0.50   20.00    --   31.63  73.80 -70.76  412
  2  ω     -5.76 200.24   0.50   20.00    --   31.63  73.80-160.76  412
  3  ω     -5.76 200.24   0.50   20.00    --   31.63  73.80  64.24  412
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0109470000
_diffrn_orient_matrix_UB_12      0.0141704000
_diffrn_orient_matrix_UB_13      0.0256692000
_diffrn_orient_matrix_UB_21      0.0312738000
_diffrn_orient_matrix_UB_22      0.0151263000
_diffrn_orient_matrix_UB_23      -0.0071347000
_diffrn_orient_matrix_UB_31      -0.0061539000
_diffrn_orient_matrix_UB_32      0.1020593000
_diffrn_orient_matrix_UB_33      -0.0025187000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5118
_reflns_number_total             5768
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.15a (Rigaku OD, 2018)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5768
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+9.4144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups, All O(H,H,H,H,H,H)
  groups
2. Restrained distances
 H1C-O1w = O1w-H1D
 0.995 with sigma of 0.002
 H1D-Br1_$1
 2.3 with sigma of 0.01
 H3C-O3w = O3w-H3D
 0.995 with sigma of 0.02
 H2C-Br1
 2.31 with sigma of 0.01
 H2D-O2w = O2w-H2C
 0.995 with sigma of 0.005
 H3BA-O3w
 1.973 with sigma of 0.02
 H3BB-Br2b_$3
 2.25 with sigma of 0.02
 H2BA-Br2a_$4
 2.25 with sigma of 0.02
 H1C-H1D
 1.579 with sigma of 0.01
 H3C-H3D
 1.6 with sigma of 0.04
 H2D-H2C
 1.55 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(Br2b) = Uanis(O3B)
Uanis(O2B) = Uanis(Br2a)
4. Rigid body (RIGU) restrains
 C3, C4
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
 C3, N1
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
 C4, C5
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
 C5, N2
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
 C1, C2
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C2, N1
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 N1, C3
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 N1, C6
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C6, C7
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C7, C8
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C7, C14
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C9, C2
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C1, C10
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C10, C11
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C11, C12
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C12, C13
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C12, C15
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
5. Others
 Fixed Sof: Br2a(0.5) Br2b(0.5) O3B(0.5) H3BA(0.5) H3BB(0.5) O2B(0.5)
 H2BA(0.5) H2BB(0.5)
6.a Free rotating group:
 O3B(H3BA,H3BB), O2B(H3C,H3D,H2C,H2D,H2BA,H2BB)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
6.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C9(H9), C11(H11), C8(H8), C10(H10)
6.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.12713(7) 0.7860(2) 0.07915(6) 0.0090(3) Uani 1 1 d . U . . .
N1 N 0.12103(7) 0.7723(2) 0.19260(6) 0.0095(2) Uani 1 1 d . U . . .
C14 C 0.11874(9) 1.0375(3) 0.31612(7) 0.0157(3) Uani 1 1 d . U . . .
H14A H 0.089250 1.136769 0.325080 0.024 Uiso 1 1 calc GR . . . .
H14B H 0.161513 1.084808 0.323032 0.024 Uiso 1 1 calc GR . . . .
H14C H 0.112890 0.920888 0.335575 0.024 Uiso 1 1 calc GR . . . .
C13 C 0.11915(8) 0.7397(2) 0.03003(6) 0.0098(3) Uani 1 1 d . U . . .
H13 H 0.154531 0.707688 0.012902 0.012 Uiso 1 1 calc R . . . .
C1 C 0.07690(8) 0.8338(2) 0.10569(6) 0.0092(3) Uani 1 1 d . U . . .
C6 C 0.13063(8) 0.8181(3) 0.24170(6) 0.0104(3) Uani 1 1 d . U . . .
H6 H 0.153621 0.732082 0.263454 0.012 Uiso 1 1 calc R . . . .
C3 C 0.14737(9) 0.5867(3) 0.17349(7) 0.0125(3) Uani 1 1 d . U . . .
H3A H 0.114715 0.519389 0.152107 0.015 Uiso 1 1 calc R . . . .
H3B H 0.160259 0.501153 0.201732 0.015 Uiso 1 1 calc R . . . .
C9 C 0.06441(8) 1.0695(3) 0.17615(7) 0.0115(3) Uani 1 1 d . U . . .
H9 H 0.042174 1.154558 0.153659 0.014 Uiso 1 1 calc R . . . .
C2 C 0.08809(8) 0.8943(2) 0.15923(6) 0.0093(3) Uani 1 1 d . U . . .
C5 C 0.19234(8) 0.7947(3) 0.10494(7) 0.0126(3) Uani 1 1 d . U . . .
H5A H 0.198236 0.920330 0.122001 0.015 Uiso 1 1 calc R . . . .
H5B H 0.223271 0.785847 0.079905 0.015 Uiso 1 1 calc R . . . .
C7 C 0.10710(8) 0.9909(3) 0.26087(7) 0.0106(3) Uani 1 1 d . U . . .
C11 C 0.00730(8) 0.7852(3) 0.03088(7) 0.0117(3) Uani 1 1 d . U . . .
H11 H -0.033544 0.785319 0.014672 0.014 Uiso 1 1 calc R . . . .
C8 C 0.07407(8) 1.1178(3) 0.22712(7) 0.0119(3) Uani 1 1 d . U . . .
H8 H 0.058299 1.235767 0.238675 0.014 Uiso 1 1 calc R . . . .
C12 C 0.05894(8) 0.7384(2) 0.00407(7) 0.0101(3) Uani 1 1 d . U . . .
C4 C 0.20436(8) 0.6286(3) 0.14352(7) 0.0138(3) Uani 1 1 d . U . . .
H4A H 0.215301 0.509874 0.125927 0.017 Uiso 1 1 calc R . . . .
H4B H 0.240520 0.663434 0.166784 0.017 Uiso 1 1 calc R . . . .
C10 C 0.01626(8) 0.8320(3) 0.08200(7) 0.0112(3) Uani 1 1 d . U . . .
H10 H -0.018515 0.861967 0.100041 0.013 Uiso 1 1 calc R . . . .
C15 C 0.05193(9) 0.6874(3) -0.05117(7) 0.0145(3) Uani 1 1 d . U . . .
H15A H 0.073367 0.565463 -0.056500 0.022 Uiso 1 1 calc GR . . . .
H15B H 0.070387 0.789757 -0.070154 0.022 Uiso 1 1 calc GR . . . .
H15C H 0.007561 0.674357 -0.062149 0.022 Uiso 1 1 calc GR . . . .
Br2 Br 0.47862(2) 0.94964(5) 0.19578(2) 0.01267(8) Uani 0.5 1 d D . P A 1
Br1 Br 0.36088(2) 0.76507(2) -0.05373(2) 0.01290(6) Uani 1 1 d D . . . .
Br3 Br 0.25674(2) 1.09680(6) 0.21603(2) 0.01267(8) Uani 0.5 1 d D . P B 1
O1 O 0.29603(7) 0.2775(2) 0.06520(6) 0.0193(3) Uani 1 1 d D . . . .
H1C H 0.3116(10) 0.163(2) 0.0858(9) 0.029 Uiso 1 1 d DR . . . .
O2 O 0.34360(8) 0.6588(2) 0.06651(6) 0.0238(3) Uani 1 1 d D . . . .
O3 O 0.34650(9) 0.9751(2) 0.13140(6) 0.0289(4) Uani 1 1 d D . . . .
O3B O 0.25751(14) 1.0092(5) 0.21166(11) 0.01267(8) Uani 0.5 1 d . . P C 2
H3BA H 0.292380 1.028558 0.187463 0.019 Uiso 0.5 1 d DG . P C 2
H3BB H 0.249020 1.149398 0.234088 0.019 Uiso 0.5 1 d DG . P C 2
O2B O 0.48601(14) 0.9810(4) 0.17768(12) 0.01267(8) Uani 0.5 1 d . . P D 2
H3C H 0.342232 0.870480 0.109780 0.019 Uiso 1 1 d DG . . . .
H3D H 0.381523 0.978310 0.150490 0.019 Uiso 1 1 d DG . . . .
H2C H 0.344570 0.690184 0.030010 0.019 Uiso 1 1 d DG . . . .
H2D H 0.328862 0.520742 0.066350 0.019 Uiso 1 1 d DG . . . .
H2BA H 0.497725 0.977731 0.215668 0.019 Uiso 0.5 1 d DG . P D 2
H2BB H 0.510303 0.939084 0.154507 0.019 Uiso 0.5 1 d G . P D 2
H1D H 0.24897(19) 0.262(4) 0.0605(12) 0.051(10) Uiso 1 1 d 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
N2 C13 1.339(2) . ?
N2 C1 1.358(2) . ?
N2 C5 1.485(2) . ?
N1 C6 1.340(2) . ?
N1 C3 1.485(2) . ?
N1 C2 1.362(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C7 1.502(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.393(2) . ?
C1 C2 1.481(2) . ?
C1 C10 1.377(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.521(3) . ?
C9 H9 0.9300 . ?
C9 C2 1.381(2) . ?
C9 C8 1.392(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.532(3) . ?
C7 C8 1.389(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(2) . ?
C11 C10 1.392(2) . ?
C8 H8 0.9300 . ?
C12 C15 1.503(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 H10 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O1 H1C 0.994(2) . ?
O1 H1D 0.995(2) . ?
O2 H2C 0.9945 . ?
O2 H2D 0.9889 . ?
O3 H3C 0.9141 . ?
O3 H3D 0.8607 . ?
O3B H3BA 1.0231 . ?
O3B H3BB 1.1456 . ?
O2B H2BA 1.0191 . ?
O2B H2BB 0.8792 . ?

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
C13 N2 C1 121.38(15) . . ?
C13 N2 C5 119.77(14) . . ?
C1 N2 C5 118.79(14) . . ?
C6 N1 C3 119.96(15) . . ?
C6 N1 C2 121.33(15) . . ?
C2 N1 C3 118.70(14) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
N2 C13 H13 119.3 . . ?
N2 C13 C12 121.35(16) . . ?
C12 C13 H13 119.3 . . ?
N2 C1 C2 119.69(15) . . ?
N2 C1 C10 119.59(16) . . ?
C10 C1 C2 120.68(15) . . ?
N1 C6 H6 119.2 . . ?
N1 C6 C7 121.60(16) . . ?
C7 C6 H6 119.2 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 C4 110.63(14) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C9 H9 120.3 . . ?
C2 C9 C8 119.47(16) . . ?
C8 C9 H9 120.3 . . ?
N1 C2 C1 119.24(15) . . ?
N1 C2 C9 119.49(16) . . ?
C9 C2 C1 121.25(15) . . ?
N2 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
N2 C5 C4 112.04(15) . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C7 C14 120.18(16) . . ?
C6 C7 C8 117.64(16) . . ?
C8 C7 C14 122.17(16) . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.28(16) . . ?
C10 C11 H11 119.9 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.46(16) . . ?
C7 C8 H8 119.8 . . ?
C13 C12 C15 119.83(16) . . ?
C11 C12 C13 117.75(16) . . ?
C11 C12 C15 122.42(16) . . ?
C3 C4 C5 113.21(14) . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C1 C10 C11 119.63(16) . . ?
C1 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H1C O1 H1D 105.4(9) . . ?
H2C O2 H2D 103.3 . . ?
H3C O3 H3D 115.2 . . ?
H3BA O3B H3BB 111.7 . . ?
H2BA O2B H2BB 125.3 . . ?

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
O1 H1C O3 0.994(2) 1.867(5) 2.853(2) 171(2) 1_545 yes
O3 H3C O2 0.91 1.84 2.753(2) 173.5 . yes
O2 H2D O1 0.99 1.79 2.779(2) 175.6 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C13 C12 C11 -0.5(2) . . . . ?
N2 C13 C12 C15 179.46(16) . . . . ?
N2 C1 C2 N1 -55.7(2) . . . . ?
N2 C1 C2 C9 125.94(18) . . . . ?
N2 C1 C10 C11 -1.3(3) . . . . ?
N2 C5 C4 C3 -39.9(2) . . . . ?
N1 C6 C7 C14 179.98(16) . . . . ?
N1 C6 C7 C8 -1.2(3) . . . . ?
N1 C3 C4 C5 -47.33(19) . . . . ?
C14 C7 C8 C9 179.81(17) . . . . ?
C13 N2 C1 C2 -176.78(15) . . . . ?
C13 N2 C1 C10 1.0(2) . . . . ?
C13 N2 C5 C4 -111.31(17) . . . . ?
C1 N2 C13 C12 0.0(2) . . . . ?
C1 N2 C5 C4 71.47(19) . . . . ?
C6 N1 C3 C4 -106.26(18) . . . . ?
C6 N1 C2 C1 -177.94(16) . . . . ?
C6 N1 C2 C9 0.4(2) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C3 N1 C6 C7 179.59(16) . . . . ?
C3 N1 C2 C1 3.0(2) . . . . ?
C3 N1 C2 C9 -178.65(15) . . . . ?
C2 N1 C6 C7 0.5(3) . . . . ?
C2 N1 C3 C4 72.84(19) . . . . ?
C2 C1 C10 C11 176.43(16) . . . . ?
C2 C9 C8 C7 -0.2(3) . . . . ?
C5 N2 C13 C12 -177.18(15) . . . . ?
C5 N2 C1 C2 0.4(2) . . . . ?
C5 N2 C1 C10 178.14(15) . . . . ?
C8 C9 C2 N1 -0.6(3) . . . . ?
C8 C9 C2 C1 177.75(16) . . . . ?
C12 C11 C10 C1 0.7(3) . . . . ?
C10 C1 C2 N1 126.57(18) . . . . ?
C10 C1 C2 C9 -51.8(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C15 -179.82(16) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id 
"5,5'-dimethyl-2,2'-bipyridine-Propyl bridged"
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.316
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# 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_mk-5-23-2016
_database_code_depnum_ccdc_archive 'CCDC 1896285'
loop_
_audit_author_name
_audit_author_address
'John Bacsa'
;Emory University
United States of America
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;
_audit_creation_date             2019-02-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), H2 O, C14 H16 N2'
_chemical_formula_sum            'C14 H18 Br2 N2 O'
_chemical_formula_weight         390.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C56  H68  Br8  N8  O4  '
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.6558(11)
_cell_length_b                   11.4656(3)
_cell_length_c                   6.9238(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.868(6)
_cell_angle_gamma                90
_cell_volume                     1487.73(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11646
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.3800
_cell_measurement_theta_min      2.0680
_shelx_estimated_absorpt_T_max   0.649
_shelx_estimated_absorpt_T_min   0.414
_exptl_absorpt_coefficient_mu    5.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  1.00000
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15a (Rigaku Oxford Diffraction, 2018)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.087
_exptl_crystal_size_rad          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16543
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.500
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.76 200.24   0.50   10.00    --   31.63  73.80 -70.76  412
  2  ω     -5.76 200.24   0.50   10.00    --   31.63  73.80 154.24  412
  3  ω     -5.76 200.24   0.50   10.00    --   31.63  73.80-160.76  412
  4  ω     -5.76 200.24   0.50   10.00    --   31.63  73.80 109.24  412
  5  ω     -2.76 200.24   0.50   10.00    --   31.63  73.80-115.76  406
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0171646000
_diffrn_orient_matrix_UB_12      -0.0225880000
_diffrn_orient_matrix_UB_13      0.0617235000
_diffrn_orient_matrix_UB_21      0.0177342000
_diffrn_orient_matrix_UB_22      0.0419674000
_diffrn_orient_matrix_UB_23      0.0802665000
_diffrn_orient_matrix_UB_31      -0.0286943000
_diffrn_orient_matrix_UB_32      0.0394474000
_diffrn_orient_matrix_UB_33      -0.0499799000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1887
_reflns_number_total             2261
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.15a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2261
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+5.6455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0855
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups
2. Restrained distances
 H1_$1-O1 = O1-H1
 0.975 with sigma of 0.02
 H1_$1-H1
 1.568 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C3, C4
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
 C4, C7
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
 C4, C5
 with sigma for 1-2 distances of 0.0003 and sigma for 1-3 distances of 0.0003
 C5, C6
 with sigma for 1-2 distances of 0.0003 and sigma for 1-3 distances of 0.0003
 C6, N1
 with sigma for 1-2 distances of 0.0003 and sigma for 1-3 distances of 0.0003
 N1, C2
 with sigma for 1-2 distances of 0.0003 and sigma for 1-3 distances of 0.0003
 C1, C1
 with sigma for 1-2 distances of 0.0003 and sigma for 1-3 distances of 0.0003
 C1, N1
 with sigma for 1-2 distances of 0.0003 and sigma for 1-3 distances of 0.0003
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.36673(2) 0.85590(2) 0.48762(4) 0.01361(9) Uani 1 1 d . . . . .
O1 O 0.500000 0.6784(3) 0.750000 0.0255(7) Uani 1 2 d DS T P . .
N1 N 0.43008(12) 0.22536(19) 0.5915(4) 0.0101(4) Uani 1 1 d . U . . .
C4 C 0.34848(15) 0.4253(2) 0.4973(4) 0.0104(4) Uani 1 1 d . U . . .
C5 C 0.42068(14) 0.4285(2) 0.6348(4) 0.0107(4) Uani 1 1 d . U . . .
H5 H 0.442089 0.500255 0.698200 0.013 Uiso 1 1 calc R . . . .
C6 C 0.46144(14) 0.3283(2) 0.6799(4) 0.0094(4) Uani 1 1 d . U . . .
C2 C 0.36014(14) 0.2187(3) 0.4630(4) 0.0128(5) Uani 1 1 d . U . . .
H2 H 0.339680 0.145348 0.405562 0.015 Uiso 1 1 calc R . . . .
C1 C 0.47430(15) 0.1193(2) 0.6352(5) 0.0141(5) Uani 1 1 d . U . . .
H1A H 0.500632 0.117985 0.544335 0.017 Uiso 1 1 calc R . . . .
H1B H 0.443599 0.049164 0.602929 0.017 Uiso 1 1 calc R . . . .
C3 C 0.31765(16) 0.3168(3) 0.4132(5) 0.0140(5) Uani 1 1 d . U . . .
H3 H 0.268137 0.311173 0.323098 0.017 Uiso 1 1 calc R . . . .
C7 C 0.30366(16) 0.5344(2) 0.4405(5) 0.0152(5) Uani 1 1 d . U . . .
H7A H 0.329214 0.596873 0.539943 0.023 Uiso 1 1 calc GR . . . .
H7B H 0.258330 0.519043 0.449499 0.023 Uiso 1 1 calc GR . . . .
H7C H 0.294277 0.558151 0.295190 0.023 Uiso 1 1 calc GR . . . .
H1 H 0.5413(9) 0.726(2) 0.817(5) 0.023 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.954(13) . ?
O1 H1 0.954(13) 2_656 ?
N1 C6 1.362(3) . ?
N1 C2 1.343(3) . ?
N1 C1 1.473(3) . ?
C4 C5 1.392(4) . ?
C4 C3 1.408(4) . ?
C4 C7 1.506(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(4) . ?
C6 C6 1.476(5) 2_656 ?
C2 H2 0.9500 . ?
C2 C3 1.378(4) . ?
C1 C1 1.495(6) 2_656 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1 O1 H1 110(3) . 2_656 ?
C6 N1 C1 119.1(2) . . ?
C2 N1 C6 121.5(2) . . ?
C2 N1 C1 119.4(2) . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 C7 121.4(2) . . ?
C3 C4 C7 120.3(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
N1 C6 C5 119.3(2) . . ?
N1 C6 C6 118.25(15) . 2_656 ?
C5 C6 C6 122.40(16) . 2_656 ?
N1 C2 H2 119.5 . . ?
N1 C2 C3 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
N1 C1 C1 108.68(19) . 2_656 ?
N1 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C1 C1 H1A 110.0 2_656 . ?
C1 C1 H1B 110.0 2_656 . ?
H1A C1 H1B 108.3 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 0.6(4) . . . . ?
C4 C5 C6 N1 -1.2(4) . . . . ?
C4 C5 C6 C6 178.3(3) . . . 2_656 ?
C5 C4 C3 C2 -2.4(4) . . . . ?
C6 N1 C2 C3 1.0(4) . . . . ?
C6 N1 C1 C1 41.0(4) . . . 2_656 ?
C2 N1 C6 C5 -0.7(4) . . . . ?
C2 N1 C6 C6 179.8(3) . . . 2_656 ?
C2 N1 C1 C1 -140.1(3) . . . 2_656 ?
C1 N1 C6 C5 178.2(2) . . . . ?
C1 N1 C6 C6 -1.3(4) . . . 2_656 ?
C1 N1 C2 C3 -177.9(3) . . . . ?
C3 C4 C5 C6 2.7(4) . . . . ?
C7 C4 C5 C6 -178.0(2) . . . . ?
C7 C4 C3 C2 178.3(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id DQ42
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_dq03
_database_code_depnum_ccdc_archive 'CCDC 1896284'
loop_
_audit_author_name
_audit_author_address
'John Bacsa'
;Emory University
United States of America
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_dq03                
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ... ? Check
RESPONSE: The potential lattice translation was tested by refinement in I2/a but 
this cell neglects the superlattice 
reflections.  The structure has a C-centered supercell with the c and b-axes doubled.
The structure refines better in the large cell and has much better-defined
thermal parameters.  The source of the superstructure Br ions and water molecules are 
swapping positions in the lattice.  
The sites are occupied about 90% of the time by Br- ions and 10% by water molecules.  
This disrupts the regular crystal symmetry but does not perturb the cation positions 
by much. 
The Br and water molecules are not exactly at the same positions but are split by 
about 1/2 Angstrom.
;
_vrf_PLAT112_dq03                
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem b/2 98 %Fit
RESPONSE: The (Pseudo) Symm. Elem b/2 98 %Fit correspond mainly to 
the organic cations positions. The structure has a C-centered supercell 
with the c and b-axes doubled.
The structure refines better in the large cell and has much better-defined
thermal parameters.  The source of the superstructure Br ions and water molecules are 
swapping positions in the lattice.  
The sites are occupied about 90% of the time by Br- ions and 10% by water molecules.  
This disrupts the regular crystal symmetry but does not perturb the cation positions 
by much. 
The Br and water molecules are not exactly at the same positions but are split by 
about 1/2 Angstrom.
;
_vrf_PLAT113_dq03                
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New Space Group I2/a Check
RESPONSE: was tested by refinement in I2/a but 
this cell neglects the superlattice 
reflections.  The structure has a C-centered supercell with the c and b-axes doubled.
The structure refines better in the large cell and has much better-defined
thermal parameters.  The source of the superstructure Br ions and water molecules are 
swapping positions in the lattice.  
;
# end Validation Reply Form
_audit_creation_date             2019-02-07
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), 0.5(O), C13 H14 N2'
_chemical_formula_sum            'C13 H15 Br2 N2 O0.50'
_chemical_formula_weight         367.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C416  H448  Br64  N64  O16  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   44.5365(10)
_cell_length_b                   14.2236(5)
_cell_length_c                   17.4936(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.743(2)
_cell_angle_gamma                90
_cell_volume                     11043.7(5)
_cell_formula_units_Z            32
_cell_measurement_reflns_used    3600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.456
_cell_measurement_theta_min      2.344
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.857
_exptl_absorpt_correction_T_max  0.12413
_exptl_absorpt_correction_T_min  0.09399
_exptl_absorpt_correction_type   sphere
_exptl_crystal_size_rad          0.4
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15a (Rigaku Oxford Diffraction, 2018)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             5791
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.687
_exptl_crystal_size_mid          0.467
_exptl_crystal_size_min          0.292
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       64
_diffrn_reflns_limit_h_min       -63
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            73108
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.999
_diffrn_reflns_theta_min         2.246
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.495
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.76 199.24   0.50   20.00    --   31.63  73.80  64.24  412
  2  ω     -6.76 199.24   0.50   20.00    --   31.63  73.80  19.24  412
  3  ω     -6.76 199.24   0.50   20.00    --   31.63  73.80-115.76  412
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0094378000
_diffrn_orient_matrix_UB_12      -0.0304062000
_diffrn_orient_matrix_UB_13      -0.0233194000
_diffrn_orient_matrix_UB_21      -0.0097700000
_diffrn_orient_matrix_UB_22      0.0381732000
_diffrn_orient_matrix_UB_23      -0.0102769000
_diffrn_orient_matrix_UB_31      0.0084332000
_diffrn_orient_matrix_UB_32      0.0099820000
_diffrn_orient_matrix_UB_33      -0.0317381000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10735
_reflns_number_total             17503
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.93
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.15a (Rigaku OD, 2018)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.331
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.161
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     658
_refine_ls_number_reflns         17503
_refine_ls_number_restraints     726
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+20.9503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Br2) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(Br9B) = Uanis(Br9)
Uanis(Br3) = Uanis(Br3B)
Uanis(Br4) = Uanis(Br4B)
Uanis(O2W) = Uanis(Br2)
Uanis(O1W) = Uanis(Br1)
Uanis(O3W) = Uanis(Br10)
Uanis(O4W) = Uanis(Br5)
3. Rigid body (RIGU) restrains
 N1_1, N2_1, C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1, C10_1,
 C11_1, C12_1, C13_1
 N1_2, N2_2, C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2, C9_2, C10_2,
 C11_2, C12_2, C13_2
 N1_3, N2_3, C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3, C8_3, C9_3, C10_3,
 C11_3, C12_3, C13_3
 N1_4, N2_4, C1_4, C2_4, C3_4, C4_4, C5_4, C6_4, C7_4, C8_4, C9_4, C10_4,
 C11_4, C12_4, C13_4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Same fragment restrains
{N1_2, N2_2, C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2, C9_2, C10_2,
C11_2, C12_2, C13_2}
{N1_3, N2_3, C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3, C8_3, C9_3, C10_3,
C11_3, C12_3, C13_3}
{N1_4, N2_4, C1_4, C2_4, C3_4, C4_4, C5_4, C6_4, C7_4, C8_4, C9_4, C10_4,
C11_4, C12_4, C13_4}
as
{N1_1, N2_1, C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1, C10_1,
C11_1, C12_1, C13_1} sigma for 1-2: 0.001 1-3: 0.001
5. Others
 Sof(Br11)=Sof(Br5)=Sof(O1W)=Sof(O2W)=1-FVAR(1)
 Sof(Br2)=Sof(Br1)=Sof(O3W)=Sof(O4W)=FVAR(1)
 Sof(Br9B)=1-FVAR(3)
 Sof(Br9)=FVAR(3)
 Sof(Br3)=1-FVAR(4)
 Sof(Br3B)=FVAR(4)
 Sof(Br4B)=1-FVAR(5)
 Sof(Br4)=FVAR(5)
6.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B),
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C6(H6),
  C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C6(H6),
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br6 Br 0.500000 0.26022(4) 0.250000 0.01675(12) Uani 1 2 d S T P . .
Br3 Br 0.42520(3) 0.59631(5) 0.01524(13) 0.0168(2) Uani 0.893(8) 1 d . . . A 1
Br4 Br 0.43469(4) 0.10046(7) -0.00932(12) 0.0177(2) Uani 0.926(10) 1 d . . . B
1
Br10 Br 0.31777(2) 0.35049(3) 0.00654(3) 0.02267(15) Uani 0.984(2) 1 d . . . C
1
Br7 Br 0.500000 0.72965(4) 0.250000 0.02025(13) Uani 1 2 d S T P . .
Br8 Br 0.24868(2) 0.50334(4) 0.25192(2) 0.01988(10) Uani 1 1 d . . . . .
Br11 Br 0.37778(2) 0.30881(3) -0.18744(2) 0.01874(11) Uani 0.9070(9) 1 d . . .
. .
Br9 Br 0.32239(2) 0.84560(4) -0.01272(7) 0.01976(19) Uani 0.933(5) 1 d . . . D
1
Br5 Br 0.37570(2) 0.05673(3) 0.19300(3) 0.01923(10) Uani 0.9070(9) 1 d . . . E
1
O1W O 0.37024(8) 0.2071(3) 0.3397(2) 0.0249(7) Uani 0.9070(9) 1 d . . . E 1
Br2 Br 0.3727(2) 0.5545(7) 0.1868(4) 0.0270(9) Uani 0.0930(9) 1 d . U . E 1
Br1 Br 0.37216(12) 0.1957(4) 0.3026(3) 0.0249(7) Uani 0.0930(9) 1 d . . . E 2
O2W O 0.37524(13) 0.5431(4) 0.1604(2) 0.0270(9) Uani 0.9070(9) 1 d . . . E 2
Br4B Br 0.4297(3) 0.0933(8) 0.0084(11) 0.0177(2) Uani 0.074(10) 1 d . . . B 2
Br9B Br 0.3163(3) 0.8474(6) 0.0107(9) 0.01976(19) Uani 0.067(5) 1 d . . . D 2
Br3B Br 0.42897(18) 0.5982(5) -0.0058(8) 0.0168(2) Uani 0.107(8) 1 d . . . A 2
O3W O 0.3276(8) 0.345(2) -0.023(2) 0.02267(15) Uani 0.0930(9) 1 d . . . E 2
O4W O 0.3794(7) 0.034(2) 0.1626(19) 0.01923(10) Uani 0.0930(9) 1 d . . . E 2
N1_1 N 0.43380(4) 0.35596(19) 0.02988(11) 0.0160(6) Uani 1 1 d D U . . .
N2_1 N 0.43004(6) 0.35595(16) 0.20142(11) 0.0166(6) Uani 1 1 d D U . . .
C1_1 C 0.45530(5) 0.3866(2) 0.08416(12) 0.0163(7) Uani 1 1 d D U . . .
C2_1 C 0.44649(6) 0.41612(18) 0.16097(12) 0.0171(7) Uani 1 1 d D U . . .
C3_1 C 0.42102(6) 0.26331(16) 0.16734(14) 0.0184(7) Uani 1 1 d D U . . .
H3A_1 H 0.414097 0.221662 0.207680 0.022 Uiso 1 1 calc R . . . .
H3B_1 H 0.438640 0.233355 0.146324 0.022 Uiso 1 1 calc R . . . .
C4_1 C 0.39569(6) 0.2753(2) 0.10325(14) 0.0202(8) Uani 1 1 d D U . . .
H4A_1 H 0.393199 0.215675 0.074167 0.024 Uiso 1 1 calc R . . . .
H4B_1 H 0.376589 0.288118 0.126495 0.024 Uiso 1 1 calc R . . . .
C5_1 C 0.40168(5) 0.3546(2) 0.04791(14) 0.0189(7) Uani 1 1 d D U . . .
H5A_1 H 0.388560 0.346490 -0.000150 0.023 Uiso 1 1 calc R . . . .
H5B_1 H 0.396581 0.415514 0.070956 0.023 Uiso 1 1 calc R . . . .
C6_1 C 0.42336(8) 0.3771(2) 0.27348(14) 0.0220(8) Uani 1 1 d D U . . .
H6_1 H 0.411962 0.333968 0.300816 0.026 Uiso 1 1 calc R . . . .
C7_1 C 0.43291(8) 0.4605(2) 0.30783(15) 0.0246(8) Uani 1 1 d D U . . .
H7_1 H 0.428081 0.474955 0.358401 0.030 Uiso 1 1 calc R . . . .
C8_1 C 0.44962(9) 0.5229(2) 0.26766(16) 0.0264(9) Uani 1 1 d D U . . .
H8_1 H 0.456292 0.580673 0.290357 0.032 Uiso 1 1 calc R . . . .
C9_1 C 0.45653(8) 0.49998(19) 0.19361(15) 0.0201(7) Uani 1 1 d D U . . .
H9_1 H 0.468119 0.541959 0.165712 0.024 Uiso 1 1 calc R . . . .
C10_1 C 0.48504(5) 0.3933(3) 0.06670(15) 0.0186(7) Uani 1 1 d D U . . .
H10_1 H 0.500149 0.414562 0.104265 0.022 Uiso 1 1 calc R . . . .
C11_1 C 0.49256(6) 0.3688(3) -0.00615(16) 0.0229(8) Uani 1 1 d D U . . .
H11_1 H 0.512758 0.374950 -0.019144 0.028 Uiso 1 1 calc R . . . .
C12_1 C 0.47056(6) 0.3354(3) -0.05975(15) 0.0231(8) Uani 1 1 d D U . . .
H12_1 H 0.475620 0.316598 -0.109198 0.028 Uiso 1 1 calc R . . . .
C13_1 C 0.44094(6) 0.3295(3) -0.04040(13) 0.0199(7) Uani 1 1 d D U . . .
H13_1 H 0.425673 0.306779 -0.076873 0.024 Uiso 1 1 calc R . . . .
N1_2 N 0.43062(4) -0.13844(19) 0.02440(11) 0.0158(6) Uani 1 1 d D U . . .
N2_2 N 0.43696(5) -0.13671(16) 0.19743(11) 0.0158(6) Uani 1 1 d D U . . .
C1_2 C 0.45567(5) -0.1144(2) 0.07040(12) 0.0154(7) Uani 1 1 d D U . . .
C2_2 C 0.45243(6) -0.08191(18) 0.15029(12) 0.0164(6) Uani 1 1 d D U . . .
C3_2 C 0.42260(6) -0.22486(16) 0.16666(14) 0.0171(7) Uani 1 1 d D U . . .
H3A_2 H 0.416778 -0.264330 0.209652 0.021 Uiso 1 1 calc R . . . .
H3B_2 H 0.437187 -0.260736 0.138411 0.021 Uiso 1 1 calc R . . . .
C4_2 C 0.39459(5) -0.2023(2) 0.11276(15) 0.0198(7) Uani 1 1 d D U . . .
H4A_2 H 0.387694 -0.260418 0.085492 0.024 Uiso 1 1 calc R . . . .
H4B_2 H 0.378229 -0.181025 0.143666 0.024 Uiso 1 1 calc R . . . .
C5_2 C 0.40039(5) -0.1267(2) 0.05391(14) 0.0182(7) Uani 1 1 d D U . . .
H5A_2 H 0.384653 -0.130326 0.010596 0.022 Uiso 1 1 calc R . . . .
H5B_2 H 0.399129 -0.063955 0.077856 0.022 Uiso 1 1 calc R . . . .
C6_2 C 0.43394(8) -0.1109(2) 0.27079(13) 0.0203(7) Uani 1 1 d D U . . .
H6_2 H 0.423132 -0.150288 0.302763 0.024 Uiso 1 1 calc R . . . .
C7_2 C 0.44637(8) -0.0280(2) 0.29983(14) 0.0215(8) Uani 1 1 d D U . . .
H7_2 H 0.444376 -0.010681 0.351602 0.026 Uiso 1 1 calc R . . . .
C8_2 C 0.46180(8) 0.0295(2) 0.25253(15) 0.0214(8) Uani 1 1 d D U . . .
H8_2 H 0.470450 0.086847 0.271547 0.026 Uiso 1 1 calc R . . . .
C9_2 C 0.46451(8) 0.00252(19) 0.17674(14) 0.0198(7) Uani 1 1 d D U . . .
H9_2 H 0.474642 0.042095 0.143463 0.024 Uiso 1 1 calc R . . . .
C10_2 C 0.48389(5) -0.1218(3) 0.04292(15) 0.0195(7) Uani 1 1 d D U . . .
H10_2 H 0.501422 -0.104818 0.074525 0.023 Uiso 1 1 calc R . . . .
C11_2 C 0.48632(6) -0.1543(3) -0.03120(16) 0.0222(8) Uani 1 1 d D U . . .
H11_2 H 0.505537 -0.158873 -0.050757 0.027 Uiso 1 1 calc R . . . .
C12_2 C 0.46069(6) -0.1799(3) -0.07647(14) 0.0217(8) Uani 1 1 d D U . . .
H12_2 H 0.462195 -0.203485 -0.126817 0.026 Uiso 1 1 calc R . . . .
C13_2 C 0.43269(6) -0.1708(3) -0.04740(14) 0.0192(7) Uani 1 1 d D U . . .
H13_2 H 0.414938 -0.187374 -0.078308 0.023 Uiso 1 1 calc R . . . .
N1_3 N 0.31976(4) 0.11455(19) -0.02788(11) 0.0161(6) Uani 1 1 d D U . . .
N2_3 N 0.31652(5) 0.11437(15) -0.20070(10) 0.0147(6) Uani 1 1 d D U . . .
C1_3 C 0.29586(5) 0.1418(2) -0.07659(12) 0.0152(7) Uani 1 1 d D U . . .
C2_3 C 0.30093(6) 0.17212(17) -0.15605(12) 0.0151(6) Uani 1 1 d D U . . .
C3_3 C 0.32926(6) 0.02513(16) -0.16761(13) 0.0164(7) Uani 1 1 d D U . . .
H3A_3 H 0.335280 -0.015980 -0.209378 0.020 Uiso 1 1 calc R . . . .
H3B_3 H 0.313712 -0.008229 -0.140694 0.020 Uiso 1 1 calc R . . . .
C4_3 C 0.35672(6) 0.0452(2) -0.11116(15) 0.0197(8) Uani 1 1 d D U . . .
H4A_3 H 0.362568 -0.013244 -0.083039 0.024 Uiso 1 1 calc R . . . .
H4B_3 H 0.373834 0.064421 -0.140333 0.024 Uiso 1 1 calc R . . . .
C5_3 C 0.35078(5) 0.1221(2) -0.05348(14) 0.0191(7) Uani 1 1 d D U . . .
H5A_3 H 0.365669 0.116920 -0.008422 0.023 Uiso 1 1 calc R . . . .
H5B_3 H 0.353320 0.184440 -0.077272 0.023 Uiso 1 1 calc R . . . .
C6_3 C 0.32052(8) 0.1371(2) -0.27421(13) 0.0187(7) Uani 1 1 d D U . . .
H6_3 H 0.331628 0.096142 -0.304183 0.022 Uiso 1 1 calc R . . . .
C7_3 C 0.30866(8) 0.2192(2) -0.30628(14) 0.0217(8) Uani 1 1 d D U . . .
H7_3 H 0.311455 0.234600 -0.358056 0.026 Uiso 1 1 calc R . . . .
C8_3 C 0.29263(8) 0.2789(2) -0.26201(15) 0.0230(8) Uani 1 1 d D U . . .
H8_3 H 0.284293 0.335577 -0.283176 0.028 Uiso 1 1 calc R . . . .
C9_3 C 0.28884(8) 0.25491(19) -0.18608(15) 0.0200(7) Uani 1 1 d D U . . .
H9_3 H 0.277977 0.295430 -0.155135 0.024 Uiso 1 1 calc R . . . .
C10_3 C 0.26701(5) 0.1394(3) -0.05230(15) 0.0198(7) Uani 1 1 d D U . . .
H10_3 H 0.250256 0.158461 -0.085877 0.024 Uiso 1 1 calc R . . . .
C11_3 C 0.26281(6) 0.1090(3) 0.02151(16) 0.0246(8) Uani 1 1 d D U . . .
H11_3 H 0.243173 0.108308 0.038990 0.030 Uiso 1 1 calc R . . . .
C12_3 C 0.28727(6) 0.0798(3) 0.06949(15) 0.0257(8) Uani 1 1 d D U . . .
H12_3 H 0.284531 0.057534 0.119629 0.031 Uiso 1 1 calc R . . . .
C13_3 C 0.31594(6) 0.0835(3) 0.04348(14) 0.0200(7) Uani 1 1 d D U . . .
H13_3 H 0.332894 0.064069 0.076163 0.024 Uiso 1 1 calc R . . . .
N1_4 N 0.31599(4) 0.60164(19) -0.02556(11) 0.0158(6) Uani 1 1 d D U . . .
N2_4 N 0.31622(6) 0.60520(16) -0.19805(11) 0.0184(6) Uani 1 1 d D U . . .
C1_4 C 0.29289(5) 0.6286(2) -0.07690(12) 0.0161(7) Uani 1 1 d D U . . .
C2_4 C 0.29947(6) 0.66114(18) -0.15477(12) 0.0175(6) Uani 1 1 d D U . . .
C3_4 C 0.32746(6) 0.51353(16) -0.16634(14) 0.0199(7) Uani 1 1 d D U . . .
H3A_4 H 0.334320 0.474206 -0.208229 0.024 Uiso 1 1 calc R . . . .
H3B_4 H 0.310897 0.479905 -0.143586 0.024 Uiso 1 1 calc R . . . .
C4_4 C 0.35363(6) 0.5285(2) -0.10494(15) 0.0206(8) Uani 1 1 d D U . . .
H4A_4 H 0.357528 0.469082 -0.076426 0.025 Uiso 1 1 calc R . . . .
H4B_4 H 0.372005 0.544511 -0.130402 0.025 Uiso 1 1 calc R . . . .
C5_4 C 0.34748(5) 0.6063(2) -0.04830(14) 0.0189(7) Uani 1 1 d D U . . .
H5A_4 H 0.361722 0.600272 -0.002023 0.023 Uiso 1 1 calc R . . . .
H5B_4 H 0.350889 0.668198 -0.071960 0.023 Uiso 1 1 calc R . . . .
C6_4 C 0.32180(9) 0.6305(2) -0.27005(14) 0.0274(9) Uani 1 1 d D U . . .
H6_4 H 0.333200 0.589883 -0.299642 0.033 Uiso 1 1 calc R . . . .
C7_4 C 0.31114(10) 0.7146(2) -0.30110(15) 0.0346(10) Uani 1 1 d D U . . .
H7_4 H 0.315508 0.732466 -0.351311 0.042 Uiso 1 1 calc R . . . .
C8_4 C 0.29400(10) 0.7725(2) -0.25814(16) 0.0325(10) Uani 1 1 d D U . . .
H8_4 H 0.286235 0.830081 -0.278921 0.039 Uiso 1 1 calc R . . . .
C9_4 C 0.28827(8) 0.7454(2) -0.18411(16) 0.0253(8) Uani 1 1 d D U . . .
H9_4 H 0.276695 0.784776 -0.153975 0.030 Uiso 1 1 calc R . . . .
C10_4 C 0.26366(5) 0.6299(3) -0.05505(16) 0.0253(8) Uani 1 1 d D U . . .
H10_4 H 0.247486 0.649480 -0.090247 0.030 Uiso 1 1 calc R . . . .
C11_4 C 0.25823(6) 0.6023(3) 0.01871(17) 0.0295(9) Uani 1 1 d D U . . .
H11_4 H 0.238324 0.603812 0.034429 0.035 Uiso 1 1 calc R . . . .
C12_4 C 0.28187(6) 0.5727(3) 0.06925(15) 0.0268(8) Uani 1 1 d D U . . .
H12_4 H 0.278293 0.552680 0.119500 0.032 Uiso 1 1 calc R . . . .
C13_4 C 0.31094(6) 0.5726(3) 0.04561(14) 0.0212(8) Uani 1 1 d D U . . .
H13_4 H 0.327299 0.551975 0.079781 0.025 Uiso 1 1 calc R . . . .


_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_1 C1_1 1.363(2) . ?
N1_1 C5_1 1.490(2) . ?
N1_1 C13_1 1.349(2) . ?
N2_1 C2_1 1.362(2) . ?
N2_1 C3_1 1.488(2) . ?
N2_1 C6_1 1.353(2) . ?
C1_1 C2_1 1.491(2) . ?
C1_1 C10_1 1.387(3) . ?
C2_1 C9_1 1.381(3) . ?
C3_1 C4_1 1.533(3) . ?
C4_1 C5_1 1.524(3) . ?
C6_1 C7_1 1.381(3) . ?
C7_1 C8_1 1.386(3) . ?
C8_1 C9_1 1.395(3) . ?
C10_1 C11_1 1.389(3) . ?
C11_1 C12_1 1.383(3) . ?
C12_1 C13_1 1.391(3) . ?
N1_2 C1_2 1.364(2) . ?
N1_2 C5_2 1.491(2) . ?
N1_2 C13_2 1.348(2) . ?
N2_2 C2_2 1.363(2) . ?
N2_2 C3_2 1.488(2) . ?
N2_2 C6_2 1.352(2) . ?
C1_2 C2_2 1.490(2) . ?
C1_2 C10_2 1.386(2) . ?
C2_2 C9_2 1.380(3) . ?
C3_2 C4_2 1.534(3) . ?
C4_2 C5_2 1.525(3) . ?
C6_2 C7_2 1.381(3) . ?
C7_2 C8_2 1.386(3) . ?
C8_2 C9_2 1.395(3) . ?
C10_2 C11_2 1.389(3) . ?
C11_2 C12_2 1.383(3) . ?
C12_2 C13_2 1.391(3) . ?
N1_3 C1_3 1.364(2) . ?
N1_3 C5_3 1.491(2) . ?
N1_3 C13_3 1.348(2) . ?
N2_3 C2_3 1.362(2) . ?
N2_3 C3_3 1.488(2) . ?
N2_3 C6_3 1.352(2) . ?
C1_3 C2_3 1.490(2) . ?
C1_3 C10_3 1.387(3) . ?
C2_3 C9_3 1.380(3) . ?
C3_3 C4_3 1.534(3) . ?
C4_3 C5_3 1.526(3) . ?
C6_3 C7_3 1.381(3) . ?
C7_3 C8_3 1.386(3) . ?
C8_3 C9_3 1.395(3) . ?
C10_3 C11_3 1.389(3) . ?
C11_3 C12_3 1.383(3) . ?
C12_3 C13_3 1.391(3) . ?
N1_4 C1_4 1.364(2) . ?
N1_4 C5_4 1.490(2) . ?
N1_4 C13_4 1.348(2) . ?
N2_4 C2_4 1.362(2) . ?
N2_4 C3_4 1.488(2) . ?
N2_4 C6_4 1.353(2) . ?
C1_4 C2_4 1.490(2) . ?
C1_4 C10_4 1.387(3) . ?
C2_4 C9_4 1.380(3) . ?
C3_4 C4_4 1.533(3) . ?
C4_4 C5_4 1.525(3) . ?
C6_4 C7_4 1.381(3) . ?
C7_4 C8_4 1.386(3) . ?
C8_4 C9_4 1.395(3) . ?
C10_4 C11_4 1.389(3) . ?
C11_4 C12_4 1.383(3) . ?
C12_4 C13_4 1.391(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
C1_1 N1_1 C5_1 119.21(15) . . ?
C13_1 N1_1 C1_1 121.28(16) . . ?
C13_1 N1_1 C5_1 119.48(16) . . ?
C2_1 N2_1 C3_1 119.16(15) . . ?
C6_1 N2_1 C2_1 120.91(17) . . ?
C6_1 N2_1 C3_1 119.82(17) . . ?
N1_1 C1_1 C2_1 119.73(16) . . ?
N1_1 C1_1 C10_1 119.81(17) . . ?
C10_1 C1_1 C2_1 120.43(17) . . ?
N2_1 C2_1 C1_1 118.97(17) . . ?
N2_1 C2_1 C9_1 119.84(17) . . ?
C9_1 C2_1 C1_1 121.02(17) . . ?
N2_1 C3_1 C4_1 110.66(17) . . ?
C5_1 C4_1 C3_1 112.95(16) . . ?
N1_1 C5_1 C4_1 111.42(16) . . ?
N2_1 C6_1 C7_1 120.85(19) . . ?
C6_1 C7_1 C8_1 119.22(19) . . ?
C7_1 C8_1 C9_1 119.4(2) . . ?
C2_1 C9_1 C8_1 119.79(19) . . ?
C1_1 C10_1 C11_1 119.46(19) . . ?
C12_1 C11_1 C10_1 119.84(19) . . ?
C11_1 C12_1 C13_1 119.23(19) . . ?
N1_1 C13_1 C12_1 120.33(19) . . ?
C1_2 N1_2 C5_2 119.05(15) . . ?
C13_2 N1_2 C1_2 121.32(16) . . ?
C13_2 N1_2 C5_2 119.61(16) . . ?
C2_2 N2_2 C3_2 119.14(15) . . ?
C6_2 N2_2 C2_2 120.94(17) . . ?
C6_2 N2_2 C3_2 119.91(16) . . ?
N1_2 C1_2 C2_2 119.55(16) . . ?
N1_2 C1_2 C10_2 119.80(17) . . ?
C10_2 C1_2 C2_2 120.65(17) . . ?
N2_2 C2_2 C1_2 118.91(17) . . ?
N2_2 C2_2 C9_2 119.85(17) . . ?
C9_2 C2_2 C1_2 121.24(17) . . ?
N2_2 C3_2 C4_2 110.47(16) . . ?
C5_2 C4_2 C3_2 112.80(16) . . ?
N1_2 C5_2 C4_2 111.30(16) . . ?
N2_2 C6_2 C7_2 120.82(19) . . ?
C6_2 C7_2 C8_2 119.22(19) . . ?
C7_2 C8_2 C9_2 119.4(2) . . ?
C2_2 C9_2 C8_2 119.74(19) . . ?
C1_2 C10_2 C11_2 119.46(19) . . ?
C12_2 C11_2 C10_2 119.86(19) . . ?
C11_2 C12_2 C13_2 119.22(19) . . ?
N1_2 C13_2 C12_2 120.32(19) . . ?
C1_3 N1_3 C5_3 119.12(15) . . ?
C13_3 N1_3 C1_3 121.31(16) . . ?
C13_3 N1_3 C5_3 119.54(16) . . ?
C2_3 N2_3 C3_3 119.17(15) . . ?
C6_3 N2_3 C2_3 120.96(17) . . ?
C6_3 N2_3 C3_3 119.88(16) . . ?
N1_3 C1_3 C2_3 119.64(16) . . ?
N1_3 C1_3 C10_3 119.80(17) . . ?
C10_3 C1_3 C2_3 120.56(17) . . ?
N2_3 C2_3 C1_3 118.93(17) . . ?
N2_3 C2_3 C9_3 119.83(17) . . ?
C9_3 C2_3 C1_3 121.16(17) . . ?
N2_3 C3_3 C4_3 110.46(16) . . ?
C5_3 C4_3 C3_3 112.73(16) . . ?
N1_3 C5_3 C4_3 111.28(16) . . ?
N2_3 C6_3 C7_3 120.83(19) . . ?
C6_3 C7_3 C8_3 119.21(19) . . ?
C7_3 C8_3 C9_3 119.4(2) . . ?
C2_3 C9_3 C8_3 119.78(19) . . ?
C1_3 C10_3 C11_3 119.47(19) . . ?
C12_3 C11_3 C10_3 119.85(19) . . ?
C11_3 C12_3 C13_3 119.23(19) . . ?
N1_3 C13_3 C12_3 120.32(19) . . ?
C1_4 N1_4 C5_4 119.15(15) . . ?
C13_4 N1_4 C1_4 121.32(16) . . ?
C13_4 N1_4 C5_4 119.53(16) . . ?
C2_4 N2_4 C3_4 119.19(15) . . ?
C6_4 N2_4 C2_4 120.91(17) . . ?
C6_4 N2_4 C3_4 119.87(17) . . ?
N1_4 C1_4 C2_4 119.64(16) . . ?
N1_4 C1_4 C10_4 119.76(17) . . ?
C10_4 C1_4 C2_4 120.52(17) . . ?
N2_4 C2_4 C1_4 118.99(17) . . ?
N2_4 C2_4 C9_4 119.86(17) . . ?
C9_4 C2_4 C1_4 121.13(17) . . ?
N2_4 C3_4 C4_4 110.62(17) . . ?
C5_4 C4_4 C3_4 112.92(16) . . ?
N1_4 C5_4 C4_4 111.39(16) . . ?
N2_4 C6_4 C7_4 120.84(19) . . ?
C6_4 C7_4 C8_4 119.22(19) . . ?
C7_4 C8_4 C9_4 119.4(2) . . ?
C2_4 C9_4 C8_4 119.8(2) . . ?
C1_4 C10_4 C11_4 119.47(19) . . ?
C12_4 C11_4 C10_4 119.87(19) . . ?
C11_4 C12_4 C13_4 119.21(19) . . ?
N1_4 C13_4 C12_4 120.32(19) . . ?

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
N1_1 C1_1 C2_1 N2_1 53.1(3) . . . . ?
N1_1 C1_1 C2_1 C9_1 -131.6(3) . . . . ?
N1_1 C1_1 C10_1 C11_1 0.1(5) . . . . ?
N2_1 C2_1 C9_1 C8_1 -0.4(5) . . . . ?
N2_1 C3_1 C4_1 C5_1 46.4(3) . . . . ?
N2_1 C6_1 C7_1 C8_1 -0.2(6) . . . . ?
C1_1 N1_1 C5_1 C4_1 -73.3(3) . . . . ?
C1_1 N1_1 C13_1 C12_1 -1.7(5) . . . . ?
C1_1 C2_1 C9_1 C8_1 -175.7(3) . . . . ?
C1_1 C10_1 C11_1 C12_1 -1.9(6) . . . . ?
C2_1 N2_1 C3_1 C4_1 -73.9(3) . . . . ?
C2_1 N2_1 C6_1 C7_1 0.4(5) . . . . ?
C2_1 C1_1 C10_1 C11_1 -177.6(3) . . . . ?
C3_1 N2_1 C2_1 C1_1 -0.8(3) . . . . ?
C3_1 N2_1 C2_1 C9_1 -176.2(3) . . . . ?
C3_1 N2_1 C6_1 C7_1 176.5(3) . . . . ?
C3_1 C4_1 C5_1 N1_1 40.9(3) . . . . ?
C5_1 N1_1 C1_1 C2_1 1.4(4) . . . . ?
C5_1 N1_1 C1_1 C10_1 -176.3(3) . . . . ?
C5_1 N1_1 C13_1 C12_1 176.4(3) . . . . ?
C6_1 N2_1 C2_1 C1_1 175.3(3) . . . . ?
C6_1 N2_1 C2_1 C9_1 -0.1(5) . . . . ?
C6_1 N2_1 C3_1 C4_1 109.9(3) . . . . ?
C6_1 C7_1 C8_1 C9_1 -0.3(6) . . . . ?
C7_1 C8_1 C9_1 C2_1 0.5(6) . . . . ?
C10_1 C1_1 C2_1 N2_1 -129.2(3) . . . . ?
C10_1 C1_1 C2_1 C9_1 46.2(4) . . . . ?
C10_1 C11_1 C12_1 C13_1 1.9(6) . . . . ?
C11_1 C12_1 C13_1 N1_1 -0.2(6) . . . . ?
C13_1 N1_1 C1_1 C2_1 179.4(3) . . . . ?
C13_1 N1_1 C1_1 C10_1 1.7(5) . . . . ?
C13_1 N1_1 C5_1 C4_1 108.7(3) . . . . ?
N1_2 C1_2 C2_2 N2_2 53.3(3) . . . . ?
N1_2 C1_2 C2_2 C9_2 -126.0(3) . . . . ?
N1_2 C1_2 C10_2 C11_2 -0.4(5) . . . . ?
N2_2 C2_2 C9_2 C8_2 2.4(5) . . . . ?
N2_2 C3_2 C4_2 C5_2 48.1(3) . . . . ?
N2_2 C6_2 C7_2 C8_2 0.7(6) . . . . ?
C1_2 N1_2 C5_2 C4_2 -74.2(3) . . . . ?
C1_2 N1_2 C13_2 C12_2 -0.3(5) . . . . ?
C1_2 C2_2 C9_2 C8_2 -178.2(3) . . . . ?
C1_2 C10_2 C11_2 C12_2 -0.8(6) . . . . ?
C2_2 N2_2 C3_2 C4_2 -73.3(3) . . . . ?
C2_2 N2_2 C6_2 C7_2 0.3(5) . . . . ?
C2_2 C1_2 C10_2 C11_2 178.5(3) . . . . ?
C3_2 N2_2 C2_2 C1_2 -2.8(3) . . . . ?
C3_2 N2_2 C2_2 C9_2 176.6(3) . . . . ?
C3_2 N2_2 C6_2 C7_2 -178.2(3) . . . . ?
C3_2 C4_2 C5_2 N1_2 39.5(3) . . . . ?
C5_2 N1_2 C1_2 C2_2 3.2(3) . . . . ?
C5_2 N1_2 C1_2 C10_2 -177.8(3) . . . . ?
C5_2 N1_2 C13_2 C12_2 178.4(3) . . . . ?
C6_2 N2_2 C2_2 C1_2 178.7(3) . . . . ?
C6_2 N2_2 C2_2 C9_2 -1.9(5) . . . . ?
C6_2 N2_2 C3_2 C4_2 105.2(3) . . . . ?
C6_2 C7_2 C8_2 C9_2 -0.1(6) . . . . ?
C7_2 C8_2 C9_2 C2_2 -1.4(6) . . . . ?
C10_2 C1_2 C2_2 N2_2 -125.6(3) . . . . ?
C10_2 C1_2 C2_2 C9_2 55.0(4) . . . . ?
C10_2 C11_2 C12_2 C13_2 1.4(6) . . . . ?
C11_2 C12_2 C13_2 N1_2 -0.9(6) . . . . ?
C13_2 N1_2 C1_2 C2_2 -178.0(3) . . . . ?
C13_2 N1_2 C1_2 C10_2 0.9(5) . . . . ?
C13_2 N1_2 C5_2 C4_2 107.0(3) . . . . ?
N1_3 C1_3 C2_3 N2_3 52.7(3) . . . . ?
N1_3 C1_3 C2_3 C9_3 -130.6(3) . . . . ?
N1_3 C1_3 C10_3 C11_3 -0.2(5) . . . . ?
N2_3 C2_3 C9_3 C8_3 0.1(5) . . . . ?
N2_3 C3_3 C4_3 C5_3 48.7(3) . . . . ?
N2_3 C6_3 C7_3 C8_3 0.4(6) . . . . ?
C1_3 N1_3 C5_3 C4_3 -74.5(3) . . . . ?
C1_3 N1_3 C13_3 C12_3 -0.9(5) . . . . ?
C1_3 C2_3 C9_3 C8_3 -176.6(3) . . . . ?
C1_3 C10_3 C11_3 C12_3 -1.2(6) . . . . ?
C2_3 N2_3 C3_3 C4_3 -73.3(3) . . . . ?
C2_3 N2_3 C6_3 C7_3 -0.6(5) . . . . ?
C2_3 C1_3 C10_3 C11_3 178.7(3) . . . . ?
C3_3 N2_3 C2_3 C1_3 -2.9(3) . . . . ?
C3_3 N2_3 C2_3 C9_3 -179.7(3) . . . . ?
C3_3 N2_3 C6_3 C7_3 179.4(3) . . . . ?
C3_3 C4_3 C5_3 N1_3 38.8(3) . . . . ?
C5_3 N1_3 C1_3 C2_3 4.2(3) . . . . ?
C5_3 N1_3 C1_3 C10_3 -176.9(3) . . . . ?
C5_3 N1_3 C13_3 C12_3 177.2(3) . . . . ?
C6_3 N2_3 C2_3 C1_3 177.1(3) . . . . ?
C6_3 N2_3 C2_3 C9_3 0.4(4) . . . . ?
C6_3 N2_3 C3_3 C4_3 106.6(3) . . . . ?
C6_3 C7_3 C8_3 C9_3 0.1(6) . . . . ?
C7_3 C8_3 C9_3 C2_3 -0.3(6) . . . . ?
C10_3 C1_3 C2_3 N2_3 -126.1(3) . . . . ?
C10_3 C1_3 C2_3 C9_3 50.6(4) . . . . ?
C10_3 C11_3 C12_3 C13_3 1.5(6) . . . . ?
C11_3 C12_3 C13_3 N1_3 -0.5(6) . . . . ?
C13_3 N1_3 C1_3 C2_3 -177.6(3) . . . . ?
C13_3 N1_3 C1_3 C10_3 1.2(5) . . . . ?
C13_3 N1_3 C5_3 C4_3 107.3(3) . . . . ?
N1_4 C1_4 C2_4 N2_4 53.2(3) . . . . ?
N1_4 C1_4 C2_4 C9_4 -128.5(3) . . . . ?
N1_4 C1_4 C10_4 C11_4 -0.9(5) . . . . ?
N2_4 C2_4 C9_4 C8_4 0.4(5) . . . . ?
N2_4 C3_4 C4_4 C5_4 45.6(3) . . . . ?
N2_4 C6_4 C7_4 C8_4 -1.3(7) . . . . ?
C1_4 N1_4 C5_4 C4_4 -73.2(3) . . . . ?
C1_4 N1_4 C13_4 C12_4 -2.3(5) . . . . ?
C1_4 C2_4 C9_4 C8_4 -177.9(3) . . . . ?
C1_4 C10_4 C11_4 C12_4 -0.9(6) . . . . ?
C2_4 N2_4 C3_4 C4_4 -74.1(3) . . . . ?
C2_4 N2_4 C6_4 C7_4 1.2(6) . . . . ?
C2_4 C1_4 C10_4 C11_4 -177.8(3) . . . . ?
C3_4 N2_4 C2_4 C1_4 -0.1(3) . . . . ?
C3_4 N2_4 C2_4 C9_4 -178.5(3) . . . . ?
C3_4 N2_4 C6_4 C7_4 178.9(4) . . . . ?
C3_4 C4_4 C5_4 N1_4 41.9(3) . . . . ?
C5_4 N1_4 C1_4 C2_4 0.6(4) . . . . ?
C5_4 N1_4 C1_4 C10_4 -176.2(3) . . . . ?
C5_4 N1_4 C13_4 C12_4 176.5(3) . . . . ?
C6_4 N2_4 C2_4 C1_4 177.6(3) . . . . ?
C6_4 N2_4 C2_4 C9_4 -0.7(5) . . . . ?
C6_4 N2_4 C3_4 C4_4 108.1(3) . . . . ?
C6_4 C7_4 C8_4 C9_4 1.0(7) . . . . ?
C7_4 C8_4 C9_4 C2_4 -0.5(6) . . . . ?
C10_4 C1_4 C2_4 N2_4 -130.0(3) . . . . ?
C10_4 C1_4 C2_4 C9_4 48.3(4) . . . . ?
C10_4 C11_4 C12_4 C13_4 1.1(6) . . . . ?
C11_4 C12_4 C13_4 N1_4 0.4(6) . . . . ?
C13_4 N1_4 C1_4 C2_4 179.4(3) . . . . ?
C13_4 N1_4 C1_4 C10_4 2.5(5) . . . . ?
C13_4 N1_4 C5_4 C4_4 108.0(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id DQ03
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.783
_oxdiff_exptl_absorpt_empirical_full_min 0.668
