# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_rds778
_database_code_depnum_ccdc_archive 'CCDC 2119912'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;NC State University Molecular Education, Technology and Research Innovation Center
United States of America
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Spot 3'
_chemical_formula_moiety         'C6 H6 Br N O2'
_chemical_formula_sum            'C6 H6 Br N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         204.03

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   11.0877(9)
_cell_length_b                   11.2881(9)
_cell_length_c                   11.6866(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.7683(18)
_cell_angle_gamma                90
_cell_volume                     1392.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    184
_cell_measurement_theta_min      2.8431
_cell_measurement_theta_max      33.6074
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.091
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    5.834
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'mu from formula'
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_T_max  0.62

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16747
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         35.06
_diffrn_reflns_theta_full        35.06
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3079
_reflns_number_gt                2655
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0485
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_number_reflns         3079
_refine_ls_number_parameters     95
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0248P)²+0.7298P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.01953(2) 0.13543(2) 0.58486(2) 0.01547(4) Uani d . . . 1 . .
O O1 0.04578(8) 0.37383(7) 0.43444(8) 0.01421(15) Uani d . . . 1 . .
O O2 0.21145(7) 0.49732(7) 0.50250(7) 0.01364(14) Uani d . . . 1 . .
N N1 0.35826(9) 0.26404(9) 0.77729(9) 0.01356(16) Uani d . . . 1 . .
H H1 0.4296(15) 0.2562(14) 0.8326(15) 0.016 Uiso d U . . 1 . .
C C1 0.26202(11) 0.18290(10) 0.75502(10) 0.01334(18) Uani d . . . 1 . .
H H1A 0.259694 0.114045 0.801044 0.016 Uiso calc U . R 1 . .
C C2 0.16978(10) 0.21964(9) 0.65400(9) 0.01075(17) Uani d . . . 1 . .
C C3 0.21112(9) 0.32691(9) 0.61342(9) 0.00977(16) Uani d . . . 1 . .
C C4 0.32948(10) 0.35064(9) 0.69355(10) 0.01223(18) Uani d . . . 1 . .
H H4 0.381506 0.416589 0.690154 0.015 Uiso calc U . R 1 . .
C C5 0.14648(10) 0.39810(9) 0.50847(9) 0.00992(16) Uani d . . . 1 . .
C C6 0.15516(12) 0.57215(10) 0.39978(11) 0.0181(2) Uani d . . . 1 . .
H H6A 0.209651 0.64107 0.402283 0.027 Uiso calc U . R 1 . .
H H6B 0.071651 0.59883 0.401588 0.027 Uiso calc U . R 1 . .
H H6C 0.145985 0.527313 0.3258 0.027 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.8735(10) ?
O1 C5 . 1.2168(13) ?
O2 C5 . 1.3449(13) ?
O2 C6 . 1.4445(14) ?
N1 C4 . 1.3507(14) ?
N1 C1 . 1.3696(15) ?
N1 H1 . 0.860(16) ?
C1 C2 . 1.3692(15) ?
C1 H1A . 0.95 ?
C2 C3 . 1.4262(15) ?
C3 C4 . 1.3859(14) ?
C3 C5 . 1.4585(14) ?
C4 H4 . 0.95 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O2 C6 . . 115.32(8) ?
C4 N1 C1 . . 110.38(9) ?
C4 N1 H1 . . 125.4(11) ?
C1 N1 H1 . . 123.9(11) ?
C2 C1 N1 . . 107.15(9) ?
C2 C1 H1A . . 126.4 ?
N1 C1 H1A . . 126.4 ?
C1 C2 C3 . . 108.22(9) ?
C1 C2 Br1 . . 123.37(8) ?
C3 C2 Br1 . . 128.39(8) ?
C4 C3 C2 . . 105.88(9) ?
C4 C3 C5 . . 125.64(10) ?
C2 C3 C5 . . 128.48(9) ?
N1 C4 C3 . . 108.38(9) ?
N1 C4 H4 . . 125.8 ?
C3 C4 H4 . . 125.8 ?
O1 C5 O2 . . 122.71(10) ?
O1 C5 C3 . . 125.63(10) ?
O2 C5 C3 . . 111.65(9) ?
O2 C6 H6A . . 109.5 ?
O2 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
O2 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C2 . . . . 0.03(12) ?
N1 C1 C2 C3 . . . . -0.09(12) ?
N1 C1 C2 Br1 . . . . 178.49(8) ?
C1 C2 C3 C4 . . . . 0.12(12) ?
Br1 C2 C3 C4 . . . . -178.36(8) ?
C1 C2 C3 C5 . . . . 178.87(10) ?
Br1 C2 C3 C5 . . . . 0.38(16) ?
C1 N1 C4 C3 . . . . 0.05(13) ?
C2 C3 C4 N1 . . . . -0.10(12) ?
C5 C3 C4 N1 . . . . -178.90(10) ?
C6 O2 C5 O1 . . . . -1.67(15) ?
C6 O2 C5 C3 . . . . 178.92(9) ?
C4 C3 C5 O1 . . . . 175.68(11) ?
C2 C3 C5 O1 . . . . -2.84(18) ?
C4 C3 C5 O2 . . . . -4.93(15) ?
C2 C3 C5 O2 . . . . 176.55(10) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 8_556 0.860(16) 2.072(16) 2.7907(12) 140.6(14) ?

####################################################################### 
# 
# 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_mo_vippn_jsl_pn1_0m
_database_code_depnum_ccdc_archive 'CCDC 2125374'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;Vidyasirimedhi Institute of Science and Technology
Thailand
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_audit_creation_date             2021-11-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H26 N2 O7'
_chemical_formula_sum            'C17 H26 N2 O7'
_chemical_formula_weight         370.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.7410(18)
_cell_length_b                   11.4272(17)
_cell_length_c                   14.676(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.466(6)
_cell_angle_gamma                90
_cell_volume                     1867.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9789
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.41
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1617 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.9234.
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    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            54216
_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         26.371
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '4-axis goniometer diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3191
_reflns_number_total             3830
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.9823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0940
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54245(9) 0.63308(8) 0.83993(7) 0.0194(2) Uani 1 1 d . . . . .
O2 O 0.69153(8) 0.38483(8) 0.53203(7) 0.0189(2) Uani 1 1 d . . . . .
O3 O 0.70997(8) 0.53777(8) 0.82049(7) 0.0204(2) Uani 1 1 d . . . . .
O4 O 0.58748(8) 0.34790(8) 0.82294(8) 0.0221(2) Uani 1 1 d . . . . .
O5 O 0.41415(10) 0.05335(9) 0.68926(8) 0.0290(3) Uani 1 1 d . . . . .
O6 O 0.23309(9) 0.09296(9) 0.60044(8) 0.0283(3) Uani 1 1 d . . . . .
O7 O 0.55557(9) 0.42583(9) 0.60615(7) 0.0217(2) Uani 1 1 d . . . . .
N1 N 0.35368(11) 0.17005(10) 0.41569(9) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.33663(11) 0.12189(10) 0.64456(9) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.58006(15) 0.60833(14) 0.94042(11) 0.0284(4) Uani 1 1 d . . . . .
H1A H 0.565590 0.525553 0.950345 0.043 Uiso 1 1 calc R U . . .
H1B H 0.534489 0.657072 0.971567 0.043 Uiso 1 1 calc R U . . .
H1C H 0.665923 0.625358 0.968352 0.043 Uiso 1 1 calc R U . . .
C2 C 0.58570(12) 0.55238(11) 0.78582(10) 0.0162(3) Uani 1 1 d . . . . .
H2 H 0.562946 0.580528 0.717892 0.019 Uiso 1 1 calc R U . . .
C3 C 0.52804(12) 0.43217(12) 0.78707(10) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.39239(12) 0.43224(12) 0.74485(10) 0.0172(3) Uani 1 1 d . . . . .
H4A H 0.371085 0.477866 0.684440 0.021 Uiso 1 1 calc R U . . .
H4B H 0.360223 0.475481 0.789813 0.021 Uiso 1 1 calc R U . . .
C5 C 0.32523(11) 0.31437(12) 0.72237(10) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.37069(11) 0.24955(11) 0.64715(10) 0.0146(3) Uani 1 1 d . . . . .
H6 H 0.460332 0.254575 0.669049 0.018 Uiso 1 1 calc R U . . .
C7 C 0.32419(12) 0.29806(12) 0.54490(10) 0.0164(3) Uani 1 1 d . . . . .
H7A H 0.238973 0.275360 0.515799 0.020 Uiso 1 1 calc R U . . .
H7B H 0.328035 0.384592 0.547520 0.020 Uiso 1 1 calc R U . . .
C8 C 0.39438(12) 0.25480(11) 0.48246(9) 0.0154(3) Uani 1 1 d . . . . .
C9 C 0.50856(12) 0.28576(12) 0.48149(10) 0.0158(3) Uani 1 1 d . . . . .
C10 C 0.58343(12) 0.37191(12) 0.54518(10) 0.0159(3) Uani 1 1 d . . . . .
C11 C 0.77590(12) 0.45692(13) 0.60320(11) 0.0214(3) Uani 1 1 d . . . . .
H11A H 0.785712 0.427119 0.668581 0.026 Uiso 1 1 calc R U . . .
H11B H 0.746667 0.538641 0.598889 0.026 Uiso 1 1 calc R U . . .
C12 C 0.89355(14) 0.45168(15) 0.58285(14) 0.0350(4) Uani 1 1 d . . . . .
H12A H 0.923297 0.370970 0.590193 0.053 Uiso 1 1 calc R U . . .
H12B H 0.952106 0.502428 0.628081 0.053 Uiso 1 1 calc R U . . .
H12C H 0.881919 0.478236 0.517028 0.053 Uiso 1 1 calc R U . . .
C13 C 0.53559(12) 0.21537(13) 0.41111(10) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.607533 0.216777 0.394583 0.024 Uiso 1 1 calc R U . . .
C14 C 0.43865(13) 0.14576(13) 0.37213(11) 0.0219(3) Uani 1 1 d . . . . .
H14 H 0.430894 0.089532 0.322855 0.026 Uiso 1 1 calc R U . . .
C15 C 0.34801(13) 0.24126(13) 0.81419(10) 0.0212(3) Uani 1 1 d . . . . .
H15A H 0.329647 0.288279 0.863616 0.032 Uiso 1 1 calc R U . . .
H15B H 0.432410 0.217100 0.837327 0.032 Uiso 1 1 calc R U . . .
H15C H 0.296502 0.171732 0.800236 0.032 Uiso 1 1 calc R U . . .
C16 C 0.77328(14) 0.64069(13) 0.80907(13) 0.0289(4) Uani 1 1 d . . . . .
H16A H 0.750889 0.660944 0.740770 0.043 Uiso 1 1 calc R U . . .
H16B H 0.859910 0.626169 0.834072 0.043 Uiso 1 1 calc R U . . .
H16C H 0.752435 0.705542 0.844521 0.043 Uiso 1 1 calc R U . . .
C17 C 0.19036(12) 0.34115(13) 0.68326(11) 0.0214(3) Uani 1 1 d . . . . .
H17A H 0.165366 0.381843 0.732562 0.032 Uiso 1 1 calc R U . . .
H17B H 0.145425 0.267792 0.666064 0.032 Uiso 1 1 calc R U . . .
H17C H 0.174168 0.390915 0.626184 0.032 Uiso 1 1 calc R U . . .
H1 H 0.2804(18) 0.1389(16) 0.3973(14) 0.036(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4275(18) . ?
O1 C2 1.4122(16) . ?
O2 C10 1.3510(16) . ?
O2 C11 1.4475(17) . ?
O3 C2 1.3948(16) . ?
O3 C16 1.4292(17) . ?
O4 C3 1.2077(17) . ?
O5 N2 1.2222(16) . ?
O6 N2 1.2280(16) . ?
O7 C10 1.2136(17) . ?
N1 C8 1.3527(18) . ?
N1 C14 1.3730(18) . ?
N1 H1 0.89(2) . ?
N2 C6 1.5099(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2 1.0000 . ?
C2 C3 1.5341(19) . ?
C3 C4 1.5151(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5428(18) . ?
C5 C6 1.5575(18) . ?
C5 C15 1.535(2) . ?
C5 C17 1.5345(18) . ?
C6 H6 1.0000 . ?
C6 C7 1.5290(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.4973(18) . ?
C8 C9 1.3910(18) . ?
C9 C10 1.4473(19) . ?
C9 C13 1.4220(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.504(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.357(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C2 O1 C1 113.76(11) . . ?
C10 O2 C11 114.73(11) . . ?
C2 O3 C16 112.43(11) . . ?
C8 N1 C14 109.87(12) . . ?
C8 N1 H1 126.3(12) . . ?
C14 N1 H1 123.6(12) . . ?
O5 N2 O6 123.71(12) . . ?
O5 N2 C6 117.35(11) . . ?
O6 N2 C6 118.91(11) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 H2 108.7 . . ?
O1 C2 C3 109.84(11) . . ?
O3 C2 O1 113.20(11) . . ?
O3 C2 H2 108.7 . . ?
O3 C2 C3 107.64(10) . . ?
C3 C2 H2 108.7 . . ?
O4 C3 C2 121.53(12) . . ?
O4 C3 C4 124.48(12) . . ?
C4 C3 C2 113.91(11) . . ?
C3 C4 H4A 107.5 . . ?
C3 C4 H4B 107.5 . . ?
C3 C4 C5 119.14(11) . . ?
H4A C4 H4B 107.0 . . ?
C5 C4 H4A 107.5 . . ?
C5 C4 H4B 107.5 . . ?
C4 C5 C6 107.46(10) . . ?
C15 C5 C4 110.62(11) . . ?
C15 C5 C6 111.09(11) . . ?
C17 C5 C4 107.63(11) . . ?
C17 C5 C6 111.99(11) . . ?
C17 C5 C15 108.00(11) . . ?
N2 C6 C5 109.26(10) . . ?
N2 C6 H6 107.9 . . ?
N2 C6 C7 108.43(11) . . ?
C5 C6 H6 107.9 . . ?
C7 C6 C5 115.29(11) . . ?
C7 C6 H6 107.9 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.72(11) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
N1 C8 C7 122.90(12) . . ?
N1 C8 C9 107.17(12) . . ?
C9 C8 C7 129.90(12) . . ?
C8 C9 C10 123.82(12) . . ?
C8 C9 C13 107.52(12) . . ?
C13 C9 C10 128.62(12) . . ?
O2 C10 C9 112.83(11) . . ?
O7 C10 O2 122.32(12) . . ?
O7 C10 C9 124.83(12) . . ?
O2 C11 H11A 110.3 . . ?
O2 C11 H11B 110.3 . . ?
O2 C11 C12 107.21(12) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13 126.6 . . ?
C14 C13 C9 106.70(12) . . ?
C14 C13 H13 126.6 . . ?
N1 C14 H14 125.6 . . ?
C13 C14 N1 108.74(12) . . ?
C13 C14 H14 125.6 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C2 C3 O4 -116.61(14) . . . . ?
O1 C2 C3 C4 60.26(15) . . . . ?
O3 C2 C3 O4 7.04(18) . . . . ?
O3 C2 C3 C4 -176.09(11) . . . . ?
O4 C3 C4 C5 -15.8(2) . . . . ?
O5 N2 C6 C5 -99.39(13) . . . . ?
O5 N2 C6 C7 134.21(12) . . . . ?
O6 N2 C6 C5 78.69(14) . . . . ?
O6 N2 C6 C7 -47.71(15) . . . . ?
N1 C8 C9 C10 -178.18(12) . . . . ?
N1 C8 C9 C13 -0.23(15) . . . . ?
N2 C6 C7 C8 -72.45(13) . . . . ?
C1 O1 C2 O3 -53.12(15) . . . . ?
C1 O1 C2 C3 67.22(14) . . . . ?
C2 C3 C4 C5 167.46(12) . . . . ?
C3 C4 C5 C6 -60.65(16) . . . . ?
C3 C4 C5 C15 60.78(16) . . . . ?
C3 C4 C5 C17 178.56(12) . . . . ?
C4 C5 C6 N2 163.46(11) . . . . ?
C4 C5 C6 C7 -74.16(14) . . . . ?
C5 C6 C7 C8 164.73(11) . . . . ?
C6 C7 C8 N1 103.13(15) . . . . ?
C6 C7 C8 C9 -74.32(18) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C7 C8 C9 C13 177.53(13) . . . . ?
C8 N1 C14 C13 0.08(17) . . . . ?
C8 C9 C10 O2 178.54(12) . . . . ?
C8 C9 C10 O7 0.3(2) . . . . ?
C8 C9 C13 C14 0.27(16) . . . . ?
C9 C13 C14 N1 -0.22(16) . . . . ?
C10 O2 C11 C12 174.56(12) . . . . ?
C10 C9 C13 C14 178.09(14) . . . . ?
C11 O2 C10 O7 6.95(18) . . . . ?
C11 O2 C10 C9 -171.31(11) . . . . ?
C13 C9 C10 O2 1.0(2) . . . . ?
C13 C9 C10 O7 -177.16(14) . . . . ?
C14 N1 C8 C7 -177.86(12) . . . . ?
C14 N1 C8 C9 0.10(16) . . . . ?
C15 C5 C6 N2 42.32(14) . . . . ?
C15 C5 C6 C7 164.70(11) . . . . ?
C16 O3 C2 O1 -67.24(15) . . . . ?
C16 O3 C2 C3 171.18(12) . . . . ?
C17 C5 C6 N2 -78.54(14) . . . . ?
C17 C5 C6 C7 43.83(15) . . . . ?

_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_rds995
_database_code_depnum_ccdc_archive 'CCDC 2120134'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;NC State University
United States of America
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JHY-NS6-E
_chemical_formula_moiety         'C15 H20 N2 O2'
_chemical_formula_sum            'C15 H20 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         260.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.1910(2)
_cell_length_b                   11.9815(2)
_cell_length_c                   21.8035(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.5170(10)
_cell_angle_gamma                90
_cell_volume                     2923.40(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    602
_cell_measurement_theta_min      4.0044
_cell_measurement_theta_max      42.5719
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale orange'
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.036
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120

_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            52347
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         74.70
_diffrn_reflns_theta_full        74.70
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_refine_special_details          
;
The ester group of residue 1 is disordered over two positions. SAME/SADI
instructions are used to maintain consistent bond lengths and angles between
the two orientations.
Both pyrole hydrogens were located in the difference map. Their position were
allowed to refine, with isotopic displacement parameter set to 1.2 times the
parent atom.
DFIX instruction employed to keep H1_1 from moving too close to
;

_reflns_number_total             5965
_reflns_number_gt                5091
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0997
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         5965
_refine_ls_number_parameters     404
_refine_ls_number_restraints     9
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+1.1126P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1_1 0.23627(9) 0.13391(9) 0.56226(5) 0.0231(2) Uani d . . D 1.0 . .
H H1_1 0.1994(12) 0.1035(12) 0.5920(6) 0.028 Uiso d U . D 1.0 . .
N N2_1 0.60341(9) -0.02187(9) 0.64392(5) 0.0252(2) Uani d . . . 1.0 . .
C C1_1 0.18907(11) 0.19890(11) 0.51757(5) 0.0260(3) Uani d . . . 1.0 . .
H H1A_1 0.107464 0.21957 0.513292 0.031 Uiso calc U . R 1.0 . .
C C2_1 0.28076(11) 0.22981(11) 0.47928(5) 0.0259(3) Uani d . . D 1.0 . .
C C3_1 0.38727(11) 0.18145(10) 0.50255(5) 0.0247(3) Uani d . . . 1.0 . .
H H3_1 0.464729 0.188724 0.485528 0.03 Uiso calc U . R 1.0 . .
C C4_1 0.35816(10) 0.12185(10) 0.55440(5) 0.0216(2) Uani d . . . 1.0 . .
C C5_1 0.42648(11) 0.05358(10) 0.59677(5) 0.0222(2) Uani d . . . 1.0 . .
H H5_1 0.382783 0.007312 0.623933 0.027 Uiso calc U . R 1.0 . .
C C6_1 0.54589(11) 0.04987(10) 0.60105(5) 0.0223(2) Uani d . . . 1.0 . .
C C7_1 0.63866(11) 0.11346(10) 0.56560(6) 0.0256(3) Uani d . . . 1.0 . .
H H7A_1 0.618507 0.193828 0.563417 0.031 Uiso calc U . R 1.0 . .
H H7B_1 0.646101 0.083776 0.523438 0.031 Uiso calc U . R 1.0 . .
C C8_1 0.75495(11) 0.09450(10) 0.60293(6) 0.0255(3) Uani d . . . 1.0 . .
C C9_1 0.71611(11) -0.00155(10) 0.64400(6) 0.0263(3) Uani d . . . 1.0 . .
C C10_1 0.80154(13) -0.06488(13) 0.68349(7) 0.0374(3) Uani d . . . 1.0 . .
H H10A_1 0.843213 -0.01316 0.711165 0.056 Uiso calc U . R 1.0 . .
H H10B_1 0.859919 -0.103066 0.657644 0.056 Uiso calc U . R 1.0 . .
H H10C_1 0.757741 -0.120097 0.707663 0.056 Uiso calc U . R 1.0 . .
C C14_1 0.78453(12) 0.19580(11) 0.64347(6) 0.0330(3) Uani d . . . 1.0 . .
H H14A_1 0.802155 0.260303 0.617433 0.05 Uiso calc U . R 1.0 . .
H H14B_1 0.854293 0.178826 0.669313 0.05 Uiso calc U . R 1.0 . .
H H14C_1 0.716033 0.212923 0.669528 0.05 Uiso calc U . R 1.0 . .
C C15_1 0.86252(12) 0.06603(12) 0.56312(6) 0.0339(3) Uani d . . . 1.0 . .
H H15A_1 0.844267 -0.000007 0.53822 0.051 Uiso calc U . R 1.0 . .
H H15B_1 0.931978 0.050643 0.589479 0.051 Uiso calc U . R 1.0 . .
H H15C_1 0.880269 0.129194 0.536139 0.051 Uiso calc U . R 1.0 . .
O O1_1 0.3582(4) 0.3137(4) 0.3905(2) 0.0428(9) Uani d . P D 0.732(5) A 1
O O2_1 0.1590(2) 0.3158(2) 0.40475(10) 0.0278(4) Uani d . P D 0.732(5) A 1
C C11_1 0.2720(4) 0.2891(3) 0.42068(17) 0.0271(9) Uani d . P D 0.732(5) A 1
C C12_1 0.14566(18) 0.37169(19) 0.34579(11) 0.0319(6) Uani d . P D 0.732(5) A 1
H H12A_1 0.063361 0.360114 0.330008 0.038 Uiso calc U P R 0.732(5) A 1
H H12B_1 0.201625 0.338128 0.316106 0.038 Uiso calc U P R 0.732(5) A 1
C C13_1 0.1700(2) 0.4948(2) 0.35075(11) 0.0376(6) Uani d . P D 0.732(5) A 1
H H13A_1 0.15721 0.530008 0.31067 0.056 Uiso calc U P R 0.732(5) A 1
H H13B_1 0.252933 0.506554 0.364099 0.056 Uiso calc U P R 0.732(5) A 1
H H13C_1 0.115845 0.527982 0.38073 0.056 Uiso calc U P R 0.732(5) A 1
O O1A_1 0.3706(10) 0.3456(10) 0.4023(6) 0.0349(19) Uani d . P D 0.268(5) A 2
O O2A_1 0.1731(5) 0.3575(6) 0.4171(3) 0.0296(12) Uani d . P D 0.268(5) A 2
C C11A_1 0.2829(10) 0.3175(8) 0.4307(5) 0.023(2) Uani d . P D 0.268(5) A 2
C C12A_1 0.1641(5) 0.4378(6) 0.3674(2) 0.0285(14) Uani d . P D 0.268(5) A 2
H H12C_1 0.232315 0.490252 0.370065 0.034 Uiso calc U P R 0.268(5) A 2
H H12D_1 0.089679 0.481615 0.371997 0.034 Uiso calc U P R 0.268(5) A 2
C C13A_1 0.1636(5) 0.3829(5) 0.3056(3) 0.0387(17) Uani d . P D 0.268(5) A 2
H H13D_1 0.153016 0.439618 0.273671 0.058 Uiso calc U P R 0.268(5) A 2
H H13E_1 0.097882 0.328983 0.303253 0.058 Uiso calc U P R 0.268(5) A 2
H H13F_1 0.239722 0.344083 0.299582 0.058 Uiso calc U P R 0.268(5) A 2
O O1_2 0.14954(8) 0.01674(7) 0.66563(4) 0.0270(2) Uani d . . . 1.0 . .
O O2_2 0.06859(8) -0.02296(7) 0.75698(4) 0.02486(19) Uani d . . . 1.0 . .
N N1_2 0.01827(9) 0.31523(9) 0.77684(4) 0.0231(2) Uani d . . . 1.0 . .
H H1_2 -0.0182(13) 0.3621(13) 0.8024(7) 0.028 Uiso d U . . 1.0 . .
N N2_2 0.17879(10) 0.63423(9) 0.66792(5) 0.0281(2) Uani d . . . 1.0 . .
C C1_2 0.01697(11) 0.20268(10) 0.77859(5) 0.0230(2) Uani d . . . 1.0 . .
H H1A_2 -0.020849 0.157926 0.808699 0.028 Uiso calc U . R 1.0 . .
C C2_2 0.08042(10) 0.16406(10) 0.72882(5) 0.0211(2) Uani d . . . 1.0 . .
C C3_2 0.12090(11) 0.25871(10) 0.69592(5) 0.0225(2) Uani d . . . 1.0 . .
H H3_2 0.166163 0.257762 0.659272 0.027 Uiso calc U . R 1.0 . .
C C4_2 0.08261(10) 0.35238(10) 0.72682(5) 0.0220(2) Uani d . . . 1.0 . .
C C5_2 0.10406(11) 0.47050(10) 0.71855(5) 0.0242(2) Uani d . . . 1.0 . .
H H5_2 0.077759 0.51903 0.750133 0.029 Uiso calc U . R 1.0 . .
C C6_2 0.15779(11) 0.51758(10) 0.67024(5) 0.0246(3) Uani d . . . 1.0 . .
C C7_2 0.20464(13) 0.46221(11) 0.61342(6) 0.0303(3) Uani d . . . 1.0 . .
H H7A_2 0.141731 0.416968 0.593103 0.036 Uiso calc U . R 1.0 . .
H H7B_2 0.273714 0.413576 0.623268 0.036 Uiso calc U . R 1.0 . .
C C8_2 0.24243(13) 0.56068(11) 0.57256(6) 0.0344(3) Uani d . . . 1.0 . .
C C9_2 0.22795(12) 0.65794(11) 0.61647(6) 0.0291(3) Uani d . . . 1.0 . .
C C10_2 0.26652(14) 0.77342(12) 0.60049(7) 0.0384(3) Uani d . . . 1.0 . .
H H10A_2 0.241269 0.825145 0.632689 0.058 Uiso calc U . R 1.0 . .
H H10B_2 0.229896 0.795413 0.561318 0.058 Uiso calc U . R 1.0 . .
H H10C_2 0.353724 0.775588 0.596955 0.058 Uiso calc U . R 1.0 . .
C C11_2 0.10392(10) 0.04834(10) 0.71339(5) 0.0215(2) Uani d . . . 1.0 . .
C C12_2 0.08898(12) -0.14088(10) 0.74456(6) 0.0277(3) Uani d . . . 1.0 . .
H H12A_2 0.175679 -0.157277 0.744428 0.033 Uiso calc U . R 1.0 . .
H H12B_2 0.054763 -0.161537 0.7041 0.033 Uiso calc U . R 1.0 . .
C C13_2 0.02861(15) -0.20493(12) 0.79471(7) 0.0407(3) Uani d . . . 1.0 . .
H H13A_2 0.039281 -0.285121 0.787818 0.061 Uiso calc U . R 1.0 . .
H H13B_2 -0.056863 -0.187133 0.794637 0.061 Uiso calc U . R 1.0 . .
H H13C_2 0.064009 -0.18433 0.834392 0.061 Uiso calc U . R 1.0 . .
C C14_2 0.1527(2) 0.57668(16) 0.51918(7) 0.0616(5) Uani d . . . 1.0 . .
H H14A_2 0.152364 0.509894 0.493232 0.092 Uiso calc U . R 1.0 . .
H H14B_2 0.176182 0.641572 0.494723 0.092 Uiso calc U . R 1.0 . .
H H14C_2 0.072557 0.588741 0.535666 0.092 Uiso calc U . R 1.0 . .
C C15_2 0.36929(18) 0.54895(15) 0.54916(11) 0.0686(6) Uani d . . . 1.0 . .
H H15A_2 0.424581 0.541446 0.584033 0.103 Uiso calc U . R 1.0 . .
H H15B_2 0.390362 0.615272 0.525283 0.103 Uiso calc U . R 1.0 . .
H H15C_2 0.374763 0.482558 0.523087 0.103 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1_1 C1_1 . 1.3511(16) ?
N1_1 C4_1 . 1.3839(15) ?
N1_1 H1_1 . 0.853(12) ?
N2_1 C9_1 . 1.2845(17) ?
N2_1 C6_1 . 1.4199(15) ?
C1_1 C2_1 . 1.3793(17) ?
C1_1 H1A_1 . 0.95 ?
C2_1 C3_1 . 1.4152(17) ?
C2_1 C11_1 . 1.464(4) ?
C2_1 C11A_1 . 1.493(10) ?
C3_1 C4_1 . 1.3787(16) ?
C3_1 H3_1 . 0.95 ?
C4_1 C5_1 . 1.4471(16) ?
C5_1 C6_1 . 1.3395(17) ?
C5_1 H5_1 . 0.95 ?
C6_1 C7_1 . 1.5068(16) ?
C7_1 C8_1 . 1.5455(17) ?
C7_1 H7A_1 . 0.99 ?
C7_1 H7B_1 . 0.99 ?
C8_1 C9_1 . 1.5238(17) ?
C8_1 C15_1 . 1.5291(17) ?
C8_1 C14_1 . 1.5359(18) ?
C9_1 C10_1 . 1.4887(18) ?
C10_1 H10A_1 . 0.98 ?
C10_1 H10B_1 . 0.98 ?
C10_1 H10C_1 . 0.98 ?
C14_1 H14A_1 . 0.98 ?
C14_1 H14B_1 . 0.98 ?
C14_1 H14C_1 . 0.98 ?
C15_1 H15A_1 . 0.98 ?
C15_1 H15B_1 . 0.98 ?
C15_1 H15C_1 . 0.98 ?
O1_1 C11_1 . 1.209(5) ?
O2_1 C11_1 . 1.347(4) ?
O2_1 C12_1 . 1.456(3) ?
C12_1 C13_1 . 1.503(3) ?
C12_1 H12A_1 . 0.99 ?
C12_1 H12B_1 . 0.99 ?
C13_1 H13A_1 . 0.98 ?
C13_1 H13B_1 . 0.98 ?
C13_1 H13C_1 . 0.98 ?
O1A_1 C11A_1 . 1.212(12) ?
O2A_1 C11A_1 . 1.349(10) ?
O2A_1 C12A_1 . 1.453(9) ?
C12A_1 C13A_1 . 1.499(7) ?
C12A_1 H12C_1 . 0.99 ?
C12A_1 H12D_1 . 0.99 ?
C13A_1 H13D_1 . 0.98 ?
C13A_1 H13E_1 . 0.98 ?
C13A_1 H13F_1 . 0.98 ?
O1_2 C11_2 . 1.2239(14) ?
O2_2 C11_2 . 1.3403(14) ?
O2_2 C12_2 . 1.4569(15) ?
N1_2 C1_2 . 1.3491(16) ?
N1_2 C4_2 . 1.3856(15) ?
N1_2 H1_2 . 0.892(15) ?
N2_2 C9_2 . 1.2857(16) ?
N2_2 C6_2 . 1.4183(16) ?
C1_2 C2_2 . 1.3821(16) ?
C1_2 H1A_2 . 0.95 ?
C2_2 C3_2 . 1.4183(16) ?
C2_2 C11_2 . 1.4513(16) ?
C3_2 C4_2 . 1.3793(16) ?
C3_2 H3_2 . 0.95 ?
C4_2 C5_2 . 1.4470(17) ?
C5_2 C6_2 . 1.3420(17) ?
C5_2 H5_2 . 0.95 ?
C6_2 C7_2 . 1.5037(17) ?
C7_2 C8_2 . 1.5400(18) ?
C7_2 H7A_2 . 0.99 ?
C7_2 H7B_2 . 0.99 ?
C8_2 C9_2 . 1.5177(18) ?
C8_2 C15_2 . 1.519(2) ?
C8_2 C14_2 . 1.542(2) ?
C9_2 C10_2 . 1.4916(18) ?
C10_2 H10A_2 . 0.98 ?
C10_2 H10B_2 . 0.98 ?
C10_2 H10C_2 . 0.98 ?
C12_2 C13_2 . 1.5013(17) ?
C12_2 H12A_2 . 0.99 ?
C12_2 H12B_2 . 0.99 ?
C13_2 H13A_2 . 0.98 ?
C13_2 H13B_2 . 0.98 ?
C13_2 H13C_2 . 0.98 ?
C14_2 H14A_2 . 0.98 ?
C14_2 H14B_2 . 0.98 ?
C14_2 H14C_2 . 0.98 ?
C15_2 H15A_2 . 0.98 ?
C15_2 H15B_2 . 0.98 ?
C15_2 H15C_2 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1_1 N1_1 C4_1 . . 110.50(10) ?
C1_1 N1_1 H1_1 . . 127.3(10) ?
C4_1 N1_1 H1_1 . . 122.2(10) ?
C9_1 N2_1 C6_1 . . 108.99(10) ?
N1_1 C1_1 C2_1 . . 107.64(11) ?
N1_1 C1_1 H1A_1 . . 126.2 ?
C2_1 C1_1 H1A_1 . . 126.2 ?
C1_1 C2_1 C3_1 . . 107.57(11) ?
C1_1 C2_1 C11_1 . . 127.9(2) ?
C3_1 C2_1 C11_1 . . 124.1(2) ?
C1_1 C2_1 C11A_1 . . 129.4(4) ?
C3_1 C2_1 C11A_1 . . 121.6(4) ?
C4_1 C3_1 C2_1 . . 107.55(10) ?
C4_1 C3_1 H3_1 . . 126.2 ?
C2_1 C3_1 H3_1 . . 126.2 ?
C3_1 C4_1 N1_1 . . 106.73(10) ?
C3_1 C4_1 C5_1 . . 133.54(11) ?
N1_1 C4_1 C5_1 . . 119.71(10) ?
C6_1 C5_1 C4_1 . . 125.75(11) ?
C6_1 C5_1 H5_1 . . 117.1 ?
C4_1 C5_1 H5_1 . . 117.1 ?
C5_1 C6_1 N2_1 . . 120.80(10) ?
C5_1 C6_1 C7_1 . . 129.72(11) ?
N2_1 C6_1 C7_1 . . 109.48(10) ?
C6_1 C7_1 C8_1 . . 103.67(9) ?
C6_1 C7_1 H7A_1 . . 111.0 ?
C8_1 C7_1 H7A_1 . . 111.0 ?
C6_1 C7_1 H7B_1 . . 111.0 ?
C8_1 C7_1 H7B_1 . . 111.0 ?
H7A_1 C7_1 H7B_1 . . 109.0 ?
C9_1 C8_1 C15_1 . . 113.29(11) ?
C9_1 C8_1 C14_1 . . 108.65(10) ?
C15_1 C8_1 C14_1 . . 109.65(11) ?
C9_1 C8_1 C7_1 . . 100.21(9) ?
C15_1 C8_1 C7_1 . . 113.41(11) ?
C14_1 C8_1 C7_1 . . 111.28(10) ?
N2_1 C9_1 C10_1 . . 121.98(12) ?
N2_1 C9_1 C8_1 . . 115.31(11) ?
C10_1 C9_1 C8_1 . . 122.66(11) ?
C9_1 C10_1 H10A_1 . . 109.5 ?
C9_1 C10_1 H10B_1 . . 109.5 ?
H10A_1 C10_1 H10B_1 . . 109.5 ?
C9_1 C10_1 H10C_1 . . 109.5 ?
H10A_1 C10_1 H10C_1 . . 109.5 ?
H10B_1 C10_1 H10C_1 . . 109.5 ?
C8_1 C14_1 H14A_1 . . 109.5 ?
C8_1 C14_1 H14B_1 . . 109.5 ?
H14A_1 C14_1 H14B_1 . . 109.5 ?
C8_1 C14_1 H14C_1 . . 109.5 ?
H14A_1 C14_1 H14C_1 . . 109.5 ?
H14B_1 C14_1 H14C_1 . . 109.5 ?
C8_1 C15_1 H15A_1 . . 109.5 ?
C8_1 C15_1 H15B_1 . . 109.5 ?
H15A_1 C15_1 H15B_1 . . 109.5 ?
C8_1 C15_1 H15C_1 . . 109.5 ?
H15A_1 C15_1 H15C_1 . . 109.5 ?
H15B_1 C15_1 H15C_1 . . 109.5 ?
C11_1 O2_1 C12_1 . . 115.2(2) ?
O1_1 C11_1 O2_1 . . 123.6(4) ?
O1_1 C11_1 C2_1 . . 123.1(4) ?
O2_1 C11_1 C2_1 . . 113.3(3) ?
O2_1 C12_1 C13_1 . . 111.7(2) ?
O2_1 C12_1 H12A_1 . . 109.3 ?
C13_1 C12_1 H12A_1 . . 109.3 ?
O2_1 C12_1 H12B_1 . . 109.3 ?
C13_1 C12_1 H12B_1 . . 109.3 ?
H12A_1 C12_1 H12B_1 . . 107.9 ?
C12_1 C13_1 H13A_1 . . 109.5 ?
C12_1 C13_1 H13B_1 . . 109.5 ?
H13A_1 C13_1 H13B_1 . . 109.5 ?
C12_1 C13_1 H13C_1 . . 109.5 ?
H13A_1 C13_1 H13C_1 . . 109.5 ?
H13B_1 C13_1 H13C_1 . . 109.5 ?
C11A_1 O2A_1 C12A_1 . . 117.1(6) ?
O1A_1 C11A_1 O2A_1 . . 122.0(10) ?
O1A_1 C11A_1 C2_1 . . 125.1(10) ?
O2A_1 C11A_1 C2_1 . . 112.6(8) ?
O2A_1 C12A_1 C13A_1 . . 112.3(7) ?
O2A_1 C12A_1 H12C_1 . . 109.1 ?
C13A_1 C12A_1 H12C_1 . . 109.1 ?
O2A_1 C12A_1 H12D_1 . . 109.1 ?
C13A_1 C12A_1 H12D_1 . . 109.1 ?
H12C_1 C12A_1 H12D_1 . . 107.9 ?
C12A_1 C13A_1 H13D_1 . . 109.5 ?
C12A_1 C13A_1 H13E_1 . . 109.5 ?
H13D_1 C13A_1 H13E_1 . . 109.5 ?
C12A_1 C13A_1 H13F_1 . . 109.5 ?
H13D_1 C13A_1 H13F_1 . . 109.5 ?
H13E_1 C13A_1 H13F_1 . . 109.5 ?
C11_2 O2_2 C12_2 . . 116.01(9) ?
C1_2 N1_2 C4_2 . . 110.44(10) ?
C1_2 N1_2 H1_2 . . 127.4(10) ?
C4_2 N1_2 H1_2 . . 122.2(10) ?
C9_2 N2_2 C6_2 . . 108.74(11) ?
N1_2 C1_2 C2_2 . . 107.85(10) ?
N1_2 C1_2 H1A_2 . . 126.1 ?
C2_2 C1_2 H1A_2 . . 126.1 ?
C1_2 C2_2 C3_2 . . 107.35(10) ?
C1_2 C2_2 C11_2 . . 126.68(11) ?
C3_2 C2_2 C11_2 . . 125.96(10) ?
C4_2 C3_2 C2_2 . . 107.55(10) ?
C4_2 C3_2 H3_2 . . 126.2 ?
C2_2 C3_2 H3_2 . . 126.2 ?
C3_2 C4_2 N1_2 . . 106.80(10) ?
C3_2 C4_2 C5_2 . . 133.03(11) ?
N1_2 C4_2 C5_2 . . 120.01(10) ?
C6_2 C5_2 C4_2 . . 125.80(11) ?
C6_2 C5_2 H5_2 . . 117.1 ?
C4_2 C5_2 H5_2 . . 117.1 ?
C5_2 C6_2 N2_2 . . 121.18(11) ?
C5_2 C6_2 C7_2 . . 128.55(11) ?
N2_2 C6_2 C7_2 . . 110.26(10) ?
C6_2 C7_2 C8_2 . . 103.78(10) ?
C6_2 C7_2 H7A_2 . . 111.0 ?
C8_2 C7_2 H7A_2 . . 111.0 ?
C6_2 C7_2 H7B_2 . . 111.0 ?
C8_2 C7_2 H7B_2 . . 111.0 ?
H7A_2 C7_2 H7B_2 . . 109.0 ?
C9_2 C8_2 C15_2 . . 112.84(13) ?
C9_2 C8_2 C7_2 . . 101.06(10) ?
C15_2 C8_2 C7_2 . . 112.68(14) ?
C9_2 C8_2 C14_2 . . 107.95(13) ?
C15_2 C8_2 C14_2 . . 111.23(15) ?
C7_2 C8_2 C14_2 . . 110.58(12) ?
N2_2 C9_2 C10_2 . . 122.40(12) ?
N2_2 C9_2 C8_2 . . 115.45(11) ?
C10_2 C9_2 C8_2 . . 122.15(11) ?
C9_2 C10_2 H10A_2 . . 109.5 ?
C9_2 C10_2 H10B_2 . . 109.5 ?
H10A_2 C10_2 H10B_2 . . 109.5 ?
C9_2 C10_2 H10C_2 . . 109.5 ?
H10A_2 C10_2 H10C_2 . . 109.5 ?
H10B_2 C10_2 H10C_2 . . 109.5 ?
O1_2 C11_2 O2_2 . . 122.29(11) ?
O1_2 C11_2 C2_2 . . 124.79(10) ?
O2_2 C11_2 C2_2 . . 112.91(10) ?
O2_2 C12_2 C13_2 . . 106.74(11) ?
O2_2 C12_2 H12A_2 . . 110.4 ?
C13_2 C12_2 H12A_2 . . 110.4 ?
O2_2 C12_2 H12B_2 . . 110.4 ?
C13_2 C12_2 H12B_2 . . 110.4 ?
H12A_2 C12_2 H12B_2 . . 108.6 ?
C12_2 C13_2 H13A_2 . . 109.5 ?
C12_2 C13_2 H13B_2 . . 109.5 ?
H13A_2 C13_2 H13B_2 . . 109.5 ?
C12_2 C13_2 H13C_2 . . 109.5 ?
H13A_2 C13_2 H13C_2 . . 109.5 ?
H13B_2 C13_2 H13C_2 . . 109.5 ?
C8_2 C14_2 H14A_2 . . 109.5 ?
C8_2 C14_2 H14B_2 . . 109.5 ?
H14A_2 C14_2 H14B_2 . . 109.5 ?
C8_2 C14_2 H14C_2 . . 109.5 ?
H14A_2 C14_2 H14C_2 . . 109.5 ?
H14B_2 C14_2 H14C_2 . . 109.5 ?
C8_2 C15_2 H15A_2 . . 109.5 ?
C8_2 C15_2 H15B_2 . . 109.5 ?
H15A_2 C15_2 H15B_2 . . 109.5 ?
C8_2 C15_2 H15C_2 . . 109.5 ?
H15A_2 C15_2 H15C_2 . . 109.5 ?
H15B_2 C15_2 H15C_2 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4_1 N1_1 C1_1 C2_1 . . . . 0.39(14) ?
N1_1 C1_1 C2_1 C3_1 . . . . -0.34(14) ?
N1_1 C1_1 C2_1 C11_1 . . . . 172.3(2) ?
N1_1 C1_1 C2_1 C11A_1 . . . . -166.8(5) ?
C1_1 C2_1 C3_1 C4_1 . . . . 0.17(14) ?
C11_1 C2_1 C3_1 C4_1 . . . . -172.8(2) ?
C11A_1 C2_1 C3_1 C4_1 . . . . 167.9(5) ?
C2_1 C3_1 C4_1 N1_1 . . . . 0.06(14) ?
C2_1 C3_1 C4_1 C5_1 . . . . 178.45(12) ?
C1_1 N1_1 C4_1 C3_1 . . . . -0.28(13) ?
C1_1 N1_1 C4_1 C5_1 . . . . -178.94(11) ?
C3_1 C4_1 C5_1 C6_1 . . . . 13.9(2) ?
N1_1 C4_1 C5_1 C6_1 . . . . -167.85(11) ?
C4_1 C5_1 C6_1 N2_1 . . . . -179.03(11) ?
C4_1 C5_1 C6_1 C7_1 . . . . 1.0(2) ?
C9_1 N2_1 C6_1 C5_1 . . . . -172.98(11) ?
C9_1 N2_1 C6_1 C7_1 . . . . 7.03(14) ?
C5_1 C6_1 C7_1 C8_1 . . . . 166.06(12) ?
N2_1 C6_1 C7_1 C8_1 . . . . -13.94(13) ?
C6_1 C7_1 C8_1 C9_1 . . . . 14.29(12) ?
C6_1 C7_1 C8_1 C15_1 . . . . 135.33(11) ?
C6_1 C7_1 C8_1 C14_1 . . . . -100.48(12) ?
C6_1 N2_1 C9_1 C10_1 . . . . -178.83(12) ?
C6_1 N2_1 C9_1 C8_1 . . . . 3.49(15) ?
C15_1 C8_1 C9_1 N2_1 . . . . -132.97(12) ?
C14_1 C8_1 C9_1 N2_1 . . . . 104.92(13) ?
C7_1 C8_1 C9_1 N2_1 . . . . -11.83(14) ?
C15_1 C8_1 C9_1 C10_1 . . . . 49.37(17) ?
C14_1 C8_1 C9_1 C10_1 . . . . -72.75(15) ?
C7_1 C8_1 C9_1 C10_1 . . . . 170.51(12) ?
C12_1 O2_1 C11_1 O1_1 . . . . 3.5(5) ?
C12_1 O2_1 C11_1 C2_1 . . . . -178.1(3) ?
C1_1 C2_1 C11_1 O1_1 . . . . 179.2(3) ?
C3_1 C2_1 C11_1 O1_1 . . . . -9.3(5) ?
C1_1 C2_1 C11_1 O2_1 . . . . 0.8(4) ?
C3_1 C2_1 C11_1 O2_1 . . . . 172.31(19) ?
C11_1 O2_1 C12_1 C13_1 . . . . -82.3(3) ?
C12A_1 O2A_1 C11A_1 O1A_1 . . . . -1.0(13) ?
C12A_1 O2A_1 C11A_1 C2_1 . . . . -175.9(6) ?
C1_1 C2_1 C11A_1 O1A_1 . . . . 173.7(7) ?
C3_1 C2_1 C11A_1 O1A_1 . . . . 8.9(12) ?
C1_1 C2_1 C11A_1 O2A_1 . . . . -11.7(9) ?
C3_1 C2_1 C11A_1 O2A_1 . . . . -176.5(5) ?
C11A_1 O2A_1 C12A_1 C13A_1 . . . . 80.5(8) ?
C4_2 N1_2 C1_2 C2_2 . . . . -0.50(14) ?
N1_2 C1_2 C2_2 C3_2 . . . . -0.18(14) ?
N1_2 C1_2 C2_2 C11_2 . . . . 178.63(11) ?
C1_2 C2_2 C3_2 C4_2 . . . . 0.79(14) ?
C11_2 C2_2 C3_2 C4_2 . . . . -178.03(11) ?
C2_2 C3_2 C4_2 N1_2 . . . . -1.07(13) ?
C2_2 C3_2 C4_2 C5_2 . . . . 174.18(13) ?
C1_2 N1_2 C4_2 C3_2 . . . . 0.99(14) ?
C1_2 N1_2 C4_2 C5_2 . . . . -175.00(11) ?
C3_2 C4_2 C5_2 C6_2 . . . . 10.0(2) ?
N1_2 C4_2 C5_2 C6_2 . . . . -175.28(12) ?
C4_2 C5_2 C6_2 N2_2 . . . . -177.35(11) ?
C4_2 C5_2 C6_2 C7_2 . . . . 1.9(2) ?
C9_2 N2_2 C6_2 C5_2 . . . . -178.22(12) ?
C9_2 N2_2 C6_2 C7_2 . . . . 2.38(15) ?
C5_2 C6_2 C7_2 C8_2 . . . . 173.79(13) ?
N2_2 C6_2 C7_2 C8_2 . . . . -6.87(15) ?
C6_2 C7_2 C8_2 C9_2 . . . . 7.93(14) ?
C6_2 C7_2 C8_2 C15_2 . . . . 128.62(14) ?
C6_2 C7_2 C8_2 C14_2 . . . . -106.20(14) ?
C6_2 N2_2 C9_2 C10_2 . . . . -177.38(13) ?
C6_2 N2_2 C9_2 C8_2 . . . . 3.53(16) ?
C15_2 C8_2 C9_2 N2_2 . . . . -128.16(15) ?
C7_2 C8_2 C9_2 N2_2 . . . . -7.58(16) ?
C14_2 C8_2 C9_2 N2_2 . . . . 108.51(15) ?
C15_2 C8_2 C9_2 C10_2 . . . . 52.7(2) ?
C7_2 C8_2 C9_2 C10_2 . . . . 173.32(13) ?
C14_2 C8_2 C9_2 C10_2 . . . . -70.58(17) ?
C12_2 O2_2 C11_2 O1_2 . . . . 0.71(16) ?
C12_2 O2_2 C11_2 C2_2 . . . . 179.79(10) ?
C1_2 C2_2 C11_2 O1_2 . . . . 171.92(12) ?
C3_2 C2_2 C11_2 O1_2 . . . . -9.5(2) ?
C1_2 C2_2 C11_2 O2_2 . . . . -7.14(17) ?
C3_2 C2_2 C11_2 O2_2 . . . . 171.46(11) ?
C11_2 O2_2 C12_2 C13_2 . . . . -172.62(11) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1_1 H1_1 O1_2 . 0.853(12) 1.997(13) 2.8341(13) 166.9(14) ?
N1_2 H1_2 N2_1 2_556 0.892(15) 2.057(16) 2.9481(14) 175.9(14) ?

####################################################################### 
# 
# 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_mo_vippn_jsl_pn4
_database_code_depnum_ccdc_archive 'CCDC 2125378'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;Vidyasirimedhi Institute of Science and Technology
Thailand
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_audit_creation_date             2021-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H53 B N2 Si2'
_chemical_formula_sum            'C38 H53 B N2 Si2'
_chemical_formula_weight         604.81
_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'
B B 0.0013 0.0007 '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'
Si Si 0.0817 0.0704 '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                   7.7500(10)
_cell_length_b                   15.783(2)
_cell_length_c                   16.094(2)
_cell_angle_alpha                106.502(5)
_cell_angle_beta                 96.507(5)
_cell_angle_gamma                99.230(5)
_cell_volume                     1836.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1455 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40609
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.194
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6248
_reflns_number_total             7529
_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 V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.043
_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)+(0.0373P)²+0.9376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C13(H13), C15(H15), C18(H18), C24(H24), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C23(H23), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
 C37(H37)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C25(H25A,
 H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C),
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si -0.07619(5) 0.18223(2) 0.15822(3) 0.01778(10) Uani 1 1 d . . . . .
Si2 Si 0.66897(5) 0.82145(3) 0.37309(3) 0.01789(10) Uani 1 1 d . . . . .
N2 N 0.37457(17) 0.56681(8) 0.70093(8) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.463(2) 0.6011(12) 0.6904(11) 0.027 Uiso 1 1 d R . . . .
N4 N 0.10869(17) 0.45182(8) 0.65223(8) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.021(2) 0.4190(12) 0.6125(12) 0.026 Uiso 1 1 d R . . . .
C1 C -0.2710(3) 0.15584(14) -0.01248(12) 0.0466(5) Uani 1 1 d . . . . .
H1A H -0.329259 0.183699 -0.052070 0.070 Uiso 1 1 calc GR . . . .
H1B H -0.359961 0.112271 0.000923 0.070 Uiso 1 1 calc GR . . . .
H1C H -0.183428 0.124765 -0.040892 0.070 Uiso 1 1 calc GR . . . .
C2 C -0.1778(2) 0.22912(10) 0.07300(10) 0.0250(3) Uani 1 1 d . . . . .
H2A H -0.271245 0.260067 0.098637 0.030 Uiso 1 1 calc R . . . .
C3 C 0.13079(19) 0.34720(9) 0.30453(9) 0.0177(3) Uani 1 1 d . . . . .
C4 C 0.20406(18) 0.42831(9) 0.37620(9) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.18679(18) 0.43097(9) 0.46238(9) 0.0160(3) Uani 1 1 d . . . . .
H5 H 0.127168 0.378514 0.472916 0.019 Uiso 1 1 calc R . . . .
C6 C 0.25498(18) 0.50881(9) 0.53343(9) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.3801(2) 0.56567(9) 0.78773(9) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.23954(19) 0.50717(9) 0.80618(9) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.2393(2) 0.50531(10) 0.89399(10) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.1000(2) 0.44621(11) 0.91171(10) 0.0257(3) Uani 1 1 d . . . . .
H11 H 0.099103 0.443564 0.969905 0.031 Uiso 1 1 calc R . . . .
C12 C 0.3719(2) 0.88080(11) 0.30184(12) 0.0316(4) Uani 1 1 d . . . . .
H12A H 0.295780 0.925435 0.311923 0.047 Uiso 1 1 calc GR . . . .
H12B H 0.303366 0.821775 0.298670 0.047 Uiso 1 1 calc GR . . . .
H12C H 0.416033 0.876798 0.246439 0.047 Uiso 1 1 calc GR . . . .
C13 C 0.5290(2) 0.90957(10) 0.37775(10) 0.0233(3) Uani 1 1 d . . . . .
H13 H 0.477578 0.917290 0.433034 0.028 Uiso 1 1 calc R . . . .
C14 C 0.6390(2) 1.00234(10) 0.38481(12) 0.0296(4) Uani 1 1 d . . . . .
H14A H 0.695073 0.997646 0.332513 0.044 Uiso 1 1 calc GR . . . .
H14B H 0.730756 1.022396 0.437350 0.044 Uiso 1 1 calc GR . . . .
H14C H 0.561236 1.046074 0.389048 0.044 Uiso 1 1 calc GR . . . .
C15 C 0.7356(2) 0.77083(10) 0.26380(10) 0.0240(3) Uani 1 1 d . . . . .
H15 H 0.821091 0.732570 0.275121 0.029 Uiso 1 1 calc R . . . .
C16 C 0.5848(2) 0.70654(12) 0.19291(11) 0.0336(4) Uani 1 1 d . . . . .
H16A H 0.505210 0.741475 0.172367 0.050 Uiso 1 1 calc GR . . . .
H16B H 0.518278 0.664130 0.217684 0.050 Uiso 1 1 calc GR . . . .
H16C H 0.634689 0.672966 0.143410 0.050 Uiso 1 1 calc GR . . . .
C17 C 0.8387(3) 0.84060(13) 0.22811(12) 0.0371(4) Uani 1 1 d . . . . .
H17A H 0.887980 0.809349 0.177265 0.056 Uiso 1 1 calc GR . . . .
H17B H 0.935424 0.880193 0.274062 0.056 Uiso 1 1 calc GR . . . .
H17C H 0.758597 0.876754 0.210255 0.056 Uiso 1 1 calc GR . . . .
C18 C 0.8711(2) 0.86710(10) 0.46231(10) 0.0231(3) Uani 1 1 d . . . . .
H18 H 0.942741 0.919914 0.450810 0.028 Uiso 1 1 calc R . . . .
C19 C 0.8190(3) 0.90086(12) 0.55315(11) 0.0360(4) Uani 1 1 d . . . . .
H19A H 0.747384 0.850534 0.566042 0.054 Uiso 1 1 calc GR . . . .
H19B H 0.750017 0.947861 0.553827 0.054 Uiso 1 1 calc GR . . . .
H19C H 0.926323 0.925786 0.597715 0.054 Uiso 1 1 calc GR . . . .
C20 C 0.9883(2) 0.79748(11) 0.46086(12) 0.0343(4) Uani 1 1 d . . . . .
H20A H 1.083289 0.820706 0.512082 0.051 Uiso 1 1 calc GR . . . .
H20B H 1.040132 0.785997 0.406953 0.051 Uiso 1 1 calc GR . . . .
H20C H 0.916371 0.741158 0.462632 0.051 Uiso 1 1 calc GR . . . .
C21 C 0.45545(19) 0.66226(9) 0.41312(9) 0.0178(3) Uani 1 1 d . . . . .
C22 C 0.36122(18) 0.58388(9) 0.42980(9) 0.0155(3) Uani 1 1 d . . . . .
C23 C 0.29148(18) 0.50510(9) 0.35972(9) 0.0152(3) Uani 1 1 d . . . . .
H23 H 0.303435 0.503777 0.301289 0.018 Uiso 1 1 calc R . . . .
C24 C -0.2447(2) 0.13218(9) 0.21637(10) 0.0216(3) Uani 1 1 d . . . . .
H24 H -0.176028 0.115936 0.264030 0.026 Uiso 1 1 calc R . . . .
C25 C -0.3518(2) 0.20031(11) 0.26175(12) 0.0309(4) Uani 1 1 d . . . . .
H25A H -0.427195 0.215449 0.217181 0.046 Uiso 1 1 calc GR . . . .
H25B H -0.270366 0.255151 0.300016 0.046 Uiso 1 1 calc GR . . . .
H25C H -0.426108 0.173830 0.297013 0.046 Uiso 1 1 calc GR . . . .
C26 C -0.3681(2) 0.04467(10) 0.15711(11) 0.0267(4) Uani 1 1 d . . . . .
H26A H -0.445755 0.019614 0.192011 0.040 Uiso 1 1 calc GR . . . .
H26B H -0.297056 0.000945 0.131576 0.040 Uiso 1 1 calc GR . . . .
H26C H -0.440381 0.057539 0.109883 0.040 Uiso 1 1 calc GR . . . .
C27 C -0.0458(2) 0.30061(11) 0.05183(11) 0.0313(4) Uani 1 1 d . . . . .
H27A H 0.046827 0.272715 0.024879 0.047 Uiso 1 1 calc GR . . . .
H27B H 0.008416 0.349097 0.106173 0.047 Uiso 1 1 calc GR . . . .
H27C H -0.108397 0.325587 0.010939 0.047 Uiso 1 1 calc GR . . . .
C28 C 0.0587(2) 0.09565(10) 0.11384(10) 0.0232(3) Uani 1 1 d . . . . .
H28 H -0.025002 0.042881 0.070128 0.028 Uiso 1 1 calc R . . . .
C29 C 0.2032(2) 0.12761(11) 0.06529(11) 0.0288(4) Uani 1 1 d . . . . .
H29A H 0.285667 0.181023 0.105431 0.043 Uiso 1 1 calc GR . . . .
H29B H 0.148186 0.142862 0.014996 0.043 Uiso 1 1 calc GR . . . .
H29C H 0.268013 0.079351 0.044468 0.043 Uiso 1 1 calc GR . . . .
C30 C 0.1389(2) 0.06141(11) 0.18693(12) 0.0325(4) Uani 1 1 d . . . . .
H30A H 0.208946 0.016734 0.162443 0.049 Uiso 1 1 calc GR . . . .
H30B H 0.043351 0.033478 0.211534 0.049 Uiso 1 1 calc GR . . . .
H30C H 0.215534 0.112185 0.233403 0.049 Uiso 1 1 calc GR . . . .
C31 C 0.3787(2) 0.56254(11) 0.96091(10) 0.0267(3) Uani 1 1 d . . . . .
H31 H 0.378596 0.563295 1.020144 0.032 Uiso 1 1 calc R . . . .
C32 C 0.5134(2) 0.61669(11) 0.94062(10) 0.0277(4) Uani 1 1 d . . . . .
H32 H 0.606673 0.653912 0.986039 0.033 Uiso 1 1 calc R . . . .
C33 C 0.5162(2) 0.61825(10) 0.85376(10) 0.0237(3) Uani 1 1 d . . . . .
H33 H 0.611677 0.655491 0.840761 0.028 Uiso 1 1 calc R . . . .
C34 C -0.0332(2) 0.39299(11) 0.84528(11) 0.0256(3) Uani 1 1 d . . . . .
H34 H -0.126211 0.354191 0.858213 0.031 Uiso 1 1 calc R . . . .
C35 C -0.0350(2) 0.39466(10) 0.75814(10) 0.0217(3) Uani 1 1 d . . . . .
H35 H -0.129316 0.357741 0.713090 0.026 Uiso 1 1 calc R . . . .
C36 C 0.10019(19) 0.44992(9) 0.73828(9) 0.0175(3) Uani 1 1 d . . . . .
C37 C 0.34229(18) 0.58480(9) 0.51549(9) 0.0159(3) Uani 1 1 d . . . . .
H37 H 0.389983 0.638457 0.562767 0.019 Uiso 1 1 calc R . . . .
C38 C 0.5360(2) 0.72683(9) 0.39866(9) 0.0203(3) Uani 1 1 d . . . . .
C39 C 0.0652(2) 0.27931(9) 0.24509(9) 0.0202(3) Uani 1 1 d . . . . .
B1 B 0.2441(2) 0.50921(10) 0.63043(11) 0.0165(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C2 1.8889(16) . ?
Si1 C24 1.8897(15) . ?
Si1 C28 1.8825(16) . ?
Si1 C39 1.8439(15) . ?
Si2 C13 1.8866(16) . ?
Si2 C15 1.8812(16) . ?
Si2 C18 1.8907(16) . ?
Si2 C38 1.8474(15) . ?
N2 H2 0.869(18) . ?
N2 C8 1.3981(18) . ?
N2 B1 1.413(2) . ?
N4 H4 0.860(18) . ?
N4 C36 1.4024(18) . ?
N4 B1 1.416(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.535(2) . ?
C2 H2A 1.0000 . ?
C2 C27 1.537(2) . ?
C3 C4 1.4392(19) . ?
C3 C39 1.206(2) . ?
C4 C5 1.398(2) . ?
C4 C23 1.3992(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3974(19) . ?
C6 C37 1.4002(19) . ?
C6 B1 1.571(2) . ?
C8 C9 1.426(2) . ?
C8 C33 1.376(2) . ?
C9 C10 1.422(2) . ?
C9 C36 1.427(2) . ?
C10 C11 1.419(2) . ?
C10 C31 1.419(2) . ?
C11 H11 0.9500 . ?
C11 C34 1.370(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C13 1.534(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.538(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 1.0000 . ?
C15 C16 1.535(2) . ?
C15 C17 1.537(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.531(2) . ?
C18 C20 1.531(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.4420(19) . ?
C21 C38 1.202(2) . ?
C22 C23 1.4000(19) . ?
C22 C37 1.3994(19) . ?
C23 H23 0.9500 . ?
C24 H24 1.0000 . ?
C24 C25 1.535(2) . ?
C24 C26 1.534(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28 1.0000 . ?
C28 C29 1.536(2) . ?
C28 C30 1.538(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31 0.9500 . ?
C31 C32 1.370(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.408(2) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.409(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.379(2) . ?
C37 H37 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Si1 C24 113.25(7) . . ?
C28 Si1 C2 113.81(7) . . ?
C28 Si1 C24 108.38(7) . . ?
C39 Si1 C2 106.42(7) . . ?
C39 Si1 C24 104.55(7) . . ?
C39 Si1 C28 110.00(7) . . ?
C13 Si2 C18 110.21(7) . . ?
C15 Si2 C13 116.18(7) . . ?
C15 Si2 C18 110.36(7) . . ?
C38 Si2 C13 107.19(7) . . ?
C38 Si2 C15 105.93(7) . . ?
C38 Si2 C18 106.39(7) . . ?
C8 N2 H2 116.5(12) . . ?
C8 N2 B1 123.44(13) . . ?
B1 N2 H2 119.7(12) . . ?
C36 N4 H4 116.2(12) . . ?
C36 N4 B1 123.45(13) . . ?
B1 N4 H4 120.1(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
Si1 C2 H2A 106.7 . . ?
C1 C2 Si1 113.23(12) . . ?
C1 C2 H2A 106.7 . . ?
C1 C2 C27 109.68(14) . . ?
C27 C2 Si1 113.49(11) . . ?
C27 C2 H2A 106.7 . . ?
C39 C3 C4 178.32(16) . . ?
C5 C4 C3 120.17(12) . . ?
C5 C4 C23 119.76(12) . . ?
C23 C4 C3 120.06(12) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.69(12) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C37 117.60(12) . . ?
C5 C6 B1 121.13(12) . . ?
C37 C6 B1 121.17(12) . . ?
N2 C8 C9 117.69(13) . . ?
C33 C8 N2 121.88(13) . . ?
C33 C8 C9 120.43(13) . . ?
C8 C9 C36 121.39(13) . . ?
C10 C9 C8 119.26(13) . . ?
C10 C9 C36 119.35(13) . . ?
C11 C10 C9 118.96(14) . . ?
C31 C10 C9 118.80(14) . . ?
C31 C10 C11 122.24(14) . . ?
C10 C11 H11 119.9 . . ?
C34 C11 C10 120.28(14) . . ?
C34 C11 H11 119.9 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
Si2 C13 H13 106.6 . . ?
C12 C13 Si2 113.27(11) . . ?
C12 C13 H13 106.6 . . ?
C12 C13 C14 110.78(13) . . ?
C14 C13 Si2 112.62(11) . . ?
C14 C13 H13 106.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si2 C15 H15 105.4 . . ?
C16 C15 Si2 114.90(11) . . ?
C16 C15 H15 105.4 . . ?
C16 C15 C17 110.88(14) . . ?
C17 C15 Si2 113.81(11) . . ?
C17 C15 H15 105.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si2 C18 H18 107.6 . . ?
C19 C18 Si2 111.34(12) . . ?
C19 C18 H18 107.6 . . ?
C20 C18 Si2 111.86(10) . . ?
C20 C18 H18 107.6 . . ?
C20 C18 C19 110.65(14) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C38 C21 C22 178.94(16) . . ?
C23 C22 C21 119.65(12) . . ?
C37 C22 C21 120.82(12) . . ?
C37 C22 C23 119.51(12) . . ?
C4 C23 C22 119.64(12) . . ?
C4 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
Si1 C24 H24 106.5 . . ?
C25 C24 Si1 112.54(10) . . ?
C25 C24 H24 106.5 . . ?
C26 C24 Si1 113.38(11) . . ?
C26 C24 H24 106.5 . . ?
C26 C24 C25 110.88(13) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2 C27 H27A 109.5 . . ?
C2 C27 H27B 109.5 . . ?
C2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Si1 C28 H28 106.9 . . ?
C29 C28 Si1 114.14(11) . . ?
C29 C28 H28 106.9 . . ?
C29 C28 C30 110.62(14) . . ?
C30 C28 Si1 110.90(11) . . ?
C30 C28 H28 106.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C10 C31 H31 119.8 . . ?
C32 C31 C10 120.39(14) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 119.4 . . ?
C31 C32 C33 121.28(15) . . ?
C33 C32 H32 119.4 . . ?
C8 C33 C32 119.79(14) . . ?
C8 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C11 C34 H34 119.4 . . ?
C11 C34 C35 121.29(14) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 119.95(14) . . ?
C36 C35 H35 120.0 . . ?
N4 C36 C9 117.45(13) . . ?
C35 C36 N4 122.40(13) . . ?
C35 C36 C9 120.15(13) . . ?
C6 C37 H37 119.1 . . ?
C22 C37 C6 121.80(12) . . ?
C22 C37 H37 119.1 . . ?
C21 C38 Si2 176.39(14) . . ?
C3 C39 Si1 168.87(14) . . ?
N2 B1 N4 116.44(13) . . ?
N2 B1 C6 120.61(13) . . ?
N4 B1 C6 122.94(13) . . ?

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 C8 C9 C10 -178.98(13) . . . . ?
N2 C8 C9 C36 1.6(2) . . . . ?
N2 C8 C33 C32 178.20(14) . . . . ?
C2 Si1 C24 C25 -57.49(13) . . . . ?
C2 Si1 C24 C26 69.38(13) . . . . ?
C2 Si1 C28 C29 53.58(13) . . . . ?
C2 Si1 C28 C30 179.33(10) . . . . ?
C2 Si1 C39 C3 66.6(7) . . . . ?
C3 C4 C5 C6 -179.45(13) . . . . ?
C3 C4 C23 C22 179.55(13) . . . . ?
C4 C5 C6 C37 -0.1(2) . . . . ?
C4 C5 C6 B1 -176.50(13) . . . . ?
C5 C4 C23 C22 0.1(2) . . . . ?
C5 C6 C37 C22 0.1(2) . . . . ?
C5 C6 B1 N2 150.25(14) . . . . ?
C5 C6 B1 N4 -28.3(2) . . . . ?
C8 N2 B1 N4 3.6(2) . . . . ?
C8 N2 B1 C6 -175.02(13) . . . . ?
C8 C9 C10 C11 -179.32(13) . . . . ?
C8 C9 C10 C31 0.5(2) . . . . ?
C8 C9 C36 N4 1.4(2) . . . . ?
C8 C9 C36 C35 -179.38(13) . . . . ?
C9 C8 C33 C32 -2.2(2) . . . . ?
C9 C10 C11 C34 -1.0(2) . . . . ?
C9 C10 C31 C32 -1.7(2) . . . . ?
C10 C9 C36 N4 -178.02(13) . . . . ?
C10 C9 C36 C35 1.2(2) . . . . ?
C10 C11 C34 C35 0.6(2) . . . . ?
C10 C31 C32 C33 1.0(3) . . . . ?
C11 C10 C31 C32 178.11(15) . . . . ?
C11 C34 C35 C36 0.7(2) . . . . ?
C13 Si2 C15 C16 -71.83(13) . . . . ?
C13 Si2 C15 C17 57.54(15) . . . . ?
C13 Si2 C18 C19 55.55(13) . . . . ?
C13 Si2 C18 C20 179.93(11) . . . . ?
C15 Si2 C13 C12 48.01(13) . . . . ?
C15 Si2 C13 C14 -78.69(13) . . . . ?
C15 Si2 C18 C19 -174.80(11) . . . . ?
C15 Si2 C18 C20 -50.42(13) . . . . ?
C18 Si2 C13 C12 174.45(11) . . . . ?
C18 Si2 C13 C14 47.76(13) . . . . ?
C18 Si2 C15 C16 161.79(12) . . . . ?
C18 Si2 C15 C17 -68.84(14) . . . . ?
C21 C22 C23 C4 178.34(13) . . . . ?
C21 C22 C37 C6 -178.47(13) . . . . ?
C23 C4 C5 C6 0.0(2) . . . . ?
C23 C22 C37 C6 0.0(2) . . . . ?
C24 Si1 C2 C1 -76.81(15) . . . . ?
C24 Si1 C2 C27 157.31(11) . . . . ?
C24 Si1 C28 C29 -179.46(11) . . . . ?
C24 Si1 C28 C30 -53.71(12) . . . . ?
C24 Si1 C39 C3 -53.5(7) . . . . ?
C28 Si1 C2 C1 47.57(15) . . . . ?
C28 Si1 C2 C27 -78.31(13) . . . . ?
C28 Si1 C24 C25 175.23(11) . . . . ?
C28 Si1 C24 C26 -57.90(13) . . . . ?
C28 Si1 C39 C3 -169.7(7) . . . . ?
C31 C10 C11 C34 179.14(15) . . . . ?
C31 C32 C33 C8 1.0(2) . . . . ?
C33 C8 C9 C10 1.4(2) . . . . ?
C33 C8 C9 C36 -177.95(14) . . . . ?
C34 C35 C36 N4 177.56(14) . . . . ?
C34 C35 C36 C9 -1.6(2) . . . . ?
C36 N4 B1 N2 -0.3(2) . . . . ?
C36 N4 B1 C6 178.29(13) . . . . ?
C36 C9 C10 C11 0.1(2) . . . . ?
C36 C9 C10 C31 179.96(14) . . . . ?
C37 C6 B1 N2 -26.0(2) . . . . ?
C37 C6 B1 N4 155.47(14) . . . . ?
C37 C22 C23 C4 -0.1(2) . . . . ?
C38 Si2 C13 C12 -70.17(13) . . . . ?
C38 Si2 C13 C14 163.14(11) . . . . ?
C38 Si2 C15 C16 47.03(14) . . . . ?
C38 Si2 C15 C17 176.41(12) . . . . ?
C38 Si2 C18 C19 -60.34(13) . . . . ?
C38 Si2 C18 C20 64.04(13) . . . . ?
C39 Si1 C2 C1 168.89(13) . . . . ?
C39 Si1 C2 C27 43.01(13) . . . . ?
C39 Si1 C24 C25 57.94(13) . . . . ?
C39 Si1 C24 C26 -175.20(11) . . . . ?
C39 Si1 C28 C29 -65.72(13) . . . . ?
C39 Si1 C28 C30 60.03(12) . . . . ?
B1 N2 C8 C9 -4.2(2) . . . . ?
B1 N2 C8 C33 175.33(14) . . . . ?
B1 N4 C36 C9 -2.1(2) . . . . ?
B1 N4 C36 C35 178.70(14) . . . . ?
B1 C6 C37 C22 176.54(13) . . . . ?

_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_x08128
_database_code_depnum_ccdc_archive 'CCDC 2120288'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;NC State University
United States of America
;
_audit_update_record             
;
2021-11-04 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H34 N4'
_chemical_formula_weight         570.71

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   9.8399(2)
_cell_length_b                   14.8436(3)
_cell_length_c                   10.9447(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.3806(11)
_cell_angle_gamma                90.00
_cell_volume                     1548.49(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.00
_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius X8 Apex2'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            29745
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2741
_reflns_number_gt                2179
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SIR92
_computing_structure_refinement  XL
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0689P)²+0.4585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2741
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.92415(14) 0.07226(9) 0.13233(12) 0.0340(3) Uani 1 1 d . . .
H1 H 0.9592 0.0460 0.0748 0.041 Uiso 1 1 calc R . .
N2 N 1.18592(14) -0.02763(9) 0.13799(12) 0.0348(3) Uani 1 1 d . . .
C1 C 0.79458(17) 0.11145(11) 0.10846(15) 0.0347(4) Uani 1 1 d . . .
C2 C 0.77964(18) 0.14668(11) 0.22432(15) 0.0372(4) Uani 1 1 d . . .
H2 H 0.7006 0.1787 0.2367 0.045 Uiso 1 1 calc R . .
C3 C 0.89931(18) 0.12661(11) 0.31626(15) 0.0352(4) Uani 1 1 d . . .
C4 C 0.99245(17) 0.07900(11) 0.25713(15) 0.0339(4) Uani 1 1 d . . .
C5 C 1.12336(17) 0.04436(11) 0.31561(15) 0.0369(4) Uani 1 1 d . . .
H5 H 1.1562 0.0564 0.4033 0.044 Uiso 1 1 calc R . .
C6 C 1.21179(17) -0.00552(11) 0.26167(15) 0.0357(4) Uani 1 1 d . . .
C7 C 1.34651(18) -0.04661(13) 0.33862(16) 0.0424(4) Uani 1 1 d . . .
H7A H 1.3275 -0.0987 0.3884 0.051 Uiso 1 1 calc R . .
H7B H 1.4033 -0.0017 0.3964 0.051 Uiso 1 1 calc R . .
C8 C 1.42015(17) -0.07631(12) 0.23729(15) 0.0374(4) Uani 1 1 d . . .
C9 C 1.29780(17) -0.07423(11) 0.11997(15) 0.0339(4) Uani 1 1 d . . .
C10 C 1.30543(18) -0.11242(12) 0.00716(15) 0.0370(4) Uani 1 1 d . . .
H10 H 1.3900 -0.1436 0.0081 0.044 Uiso 1 1 calc R . .
C11 C 1.5279(2) -0.00555(14) 0.22148(19) 0.0519(5) Uani 1 1 d . . .
H11A H 1.5677 -0.0227 0.1511 0.078 Uiso 1 1 calc R . .
H11B H 1.6031 -0.0020 0.2992 0.078 Uiso 1 1 calc R . .
H11C H 1.4819 0.0533 0.2040 0.078 Uiso 1 1 calc R . .
C12 C 1.4905(2) -0.16773(13) 0.26283(17) 0.0479(5) Uani 1 1 d . . .
H12A H 1.4196 -0.2139 0.2640 0.072 Uiso 1 1 calc R . .
H12B H 1.5594 -0.1666 0.3447 0.072 Uiso 1 1 calc R . .
H12C H 1.5380 -0.1818 0.1963 0.072 Uiso 1 1 calc R . .
C13 C 0.93009(18) 0.14781(11) 0.44613(16) 0.0367(4) Uani 1 1 d . . .
C14 C 0.96045(18) 0.16509(12) 0.55642(16) 0.0392(4) Uani 1 1 d . . .
C15 C 0.99738(19) 0.18307(12) 0.68974(15) 0.0382(4) Uani 1 1 d . . .
C16 C 1.1118(2) 0.13951(12) 0.76817(17) 0.0437(5) Uani 1 1 d . . .
H16 H 1.1652 0.0978 0.7335 0.052 Uiso 1 1 calc R . .
C17 C 1.1477(2) 0.15670(13) 0.89577(17) 0.0490(5) Uani 1 1 d . . .
H17 H 1.2264 0.1273 0.9487 0.059 Uiso 1 1 calc R . .
C18 C 1.0707(2) 0.21580(15) 0.94638(18) 0.0576(6) Uani 1 1 d . . .
H18 H 1.0953 0.2268 1.0346 0.069 Uiso 1 1 calc R . .
C19 C 0.9563(2) 0.26000(14) 0.86962(19) 0.0549(5) Uani 1 1 d . . .
H19 H 0.9036 0.3014 0.9054 0.066 Uiso 1 1 calc R . .
C20 C 0.91949(19) 0.24384(12) 0.74182(17) 0.0429(4) Uani 1 1 d . . .
H20 H 0.8413 0.2740 0.6893 0.051 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 C1 1.366(2) . ?
N1 C4 1.368(2) . ?
N1 H1 0.8800 . ?
N2 C6 1.354(2) . ?
N2 C9 1.355(2) . ?
C1 C10 1.397(2) 3_755 ?
C1 C2 1.413(2) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9500 . ?
C3 C13 1.413(2) . ?
C3 C4 1.433(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.511(2) . ?
C7 C8 1.532(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C12 1.518(2) . ?
C8 C9 1.527(2) . ?
C8 C11 1.533(3) . ?
C9 C10 1.377(2) . ?
C10 C1 1.397(2) 3_755 ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.197(2) . ?
C14 C15 1.438(2) . ?
C15 C16 1.394(3) . ?
C15 C20 1.394(2) . ?
C16 C17 1.377(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.364(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 111.32(13) . . ?
C1 N1 H1 124.3 . . ?
C4 N1 H1 124.3 . . ?
C6 N2 C9 108.14(13) . . ?
N1 C1 C10 126.27(15) . 3_755 ?
N1 C1 C2 106.63(14) . . ?
C10 C1 C2 127.04(16) 3_755 . ?
C3 C2 C1 108.36(15) . . ?
C3 C2 H2 125.8 . . ?
C1 C2 H2 125.8 . . ?
C2 C3 C13 128.10(16) . . ?
C2 C3 C4 107.65(14) . . ?
C13 C3 C4 124.25(16) . . ?
N1 C4 C5 127.11(15) . . ?
N1 C4 C3 106.04(14) . . ?
C5 C4 C3 126.82(15) . . ?
C6 C5 C4 127.79(15) . . ?
C6 C5 H5 116.1 . . ?
C4 C5 H5 116.1 . . ?
N2 C6 C5 125.10(15) . . ?
N2 C6 C7 112.35(14) . . ?
C5 C6 C7 122.45(15) . . ?
C6 C7 C8 102.70(13) . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C12 C8 C9 113.67(14) . . ?
C12 C8 C7 113.58(14) . . ?
C9 C8 C7 100.78(13) . . ?
C12 C8 C11 109.68(15) . . ?
C9 C8 C11 108.33(14) . . ?
C7 C8 C11 110.45(15) . . ?
N2 C9 C10 124.58(15) . . ?
N2 C9 C8 112.78(14) . . ?
C10 C9 C8 122.57(15) . . ?
C9 C10 C1 128.66(16) . 3_755 ?
C9 C10 H10 115.7 . . ?
C1 C10 H10 115.7 3_755 . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 177.95(19) . . ?
C13 C14 C15 178.32(18) . . ?
C16 C15 C20 119.37(16) . . ?
C16 C15 C14 120.04(16) . . ?
C20 C15 C14 120.59(17) . . ?
C17 C16 C15 120.21(18) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.19(19) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.42(18) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.09(19) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 119.72(18) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?

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
C4 N1 C1 C10 -176.35(16) . . . 3_755 ?
C4 N1 C1 C2 0.95(18) . . . . ?
N1 C1 C2 C3 -1.11(19) . . . . ?
C10 C1 C2 C3 176.17(16) 3_755 . . . ?
C1 C2 C3 C13 -179.38(16) . . . . ?
C1 C2 C3 C4 0.85(19) . . . . ?
C1 N1 C4 C5 177.70(16) . . . . ?
C1 N1 C4 C3 -0.43(18) . . . . ?
C2 C3 C4 N1 -0.28(18) . . . . ?
C13 C3 C4 N1 179.95(15) . . . . ?
C2 C3 C4 C5 -178.42(16) . . . . ?
C13 C3 C4 C5 1.8(3) . . . . ?
N1 C4 C5 C6 -1.3(3) . . . . ?
C3 C4 C5 C6 176.51(17) . . . . ?
C9 N2 C6 C5 178.17(16) . . . . ?
C9 N2 C6 C7 -5.40(19) . . . . ?
C4 C5 C6 N2 1.8(3) . . . . ?
C4 C5 C6 C7 -174.26(17) . . . . ?
N2 C6 C7 C8 15.02(19) . . . . ?
C5 C6 C7 C8 -168.44(16) . . . . ?
C6 C7 C8 C12 -138.79(16) . . . . ?
C6 C7 C8 C9 -16.85(16) . . . . ?
C6 C7 C8 C11 97.51(16) . . . . ?
C6 N2 C9 C10 175.95(16) . . . . ?
C6 N2 C9 C8 -7.06(19) . . . . ?
C12 C8 C9 N2 137.65(15) . . . . ?
C7 C8 C9 N2 15.77(18) . . . . ?
C11 C8 C9 N2 -100.18(17) . . . . ?
C12 C8 C9 C10 -45.3(2) . . . . ?
C7 C8 C9 C10 -167.17(16) . . . . ?
C11 C8 C9 C10 76.9(2) . . . . ?
N2 C9 C10 C1 0.4(3) . . . 3_755 ?
C8 C9 C10 C1 -176.27(16) . . . 3_755 ?
C2 C3 C13 C14 -166(5) . . . . ?
C4 C3 C13 C14 13(5) . . . . ?
C3 C13 C14 C15 -73(9) . . . . ?
C13 C14 C15 C16 46(6) . . . . ?
C13 C14 C15 C20 -134(6) . . . . ?
C20 C15 C16 C17 -0.3(3) . . . . ?
C14 C15 C16 C17 179.84(16) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
C14 C15 C20 C19 179.87(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_x08184
_database_code_depnum_ccdc_archive 'CCDC 2120866'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;NC State University
United States of America
;
_audit_update_record             
;
2022-01-31 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_audit_creation_date             2022-01-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H24 Br2 N4'
_chemical_formula_sum            'C24 H24 Br2 N4'
_chemical_formula_weight         528.29
_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'
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'

_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   20.0268(6)
_cell_length_b                   20.0268(6)
_cell_length_c                   14.4186(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5008.1(3)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    8320
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      3.41
_shelx_estimated_absorpt_T_max   0.810
_shelx_estimated_absorpt_T_min   0.528
_exptl_absorpt_coefficient_mu    3.661
_exptl_absorpt_correction_T_max  0.8103
_exptl_absorpt_correction_T_min  0.5280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2394
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48159
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         28.029
_diffrn_reflns_theta_min         1.837
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius X8 Apex2'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2063
_reflns_number_total             2699
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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
_computing_data_collection       Apex2
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         1.117
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+11.7972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C10(H10)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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
Br1 Br 0.46980(2) 0.11145(2) 0.33061(2) 0.03648(11) Uani 1 1 d . . . . .
N1 N 0.35011(12) 0.11243(12) 0.55429(14) 0.0223(4) Uani 1 1 d . . . . .
H1 H 0.341843 0.134370 0.602404 0.027 Uiso 1 1 calc R U . . .
N2 N 0.43856(11) 0.26971(12) 0.64027(14) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.30160(14) 0.03760(14) 0.52618(17) 0.0238(5) Uani 1 1 d . . . . .
C2 C 0.33528(15) 0.02506(15) 0.44683(18) 0.0271(6) Uani 1 1 d . . . . .
H2 H 0.315203 -0.021418 0.412246 0.033 Uiso 1 1 calc R U . . .
C3 C 0.40212(15) 0.09227(15) 0.42913(17) 0.0246(5) Uani 1 1 d . . . . .
C4 C 0.41292(14) 0.14796(14) 0.49712(16) 0.0220(5) Uani 1 1 d . . . . .
C5 C 0.47473(14) 0.22267(14) 0.50520(17) 0.0224(5) Uani 1 1 d . . . . .
H5 H 0.513739 0.237477 0.459403 0.027 Uiso 1 1 calc R U . . .
C6 C 0.48759(14) 0.27863(14) 0.57051(16) 0.0220(5) Uani 1 1 d . . . . .
C7 C 0.55869(16) 0.35734(16) 0.56944(19) 0.0308(6) Uani 1 1 d . . . . .
H7A H 0.562454 0.384599 0.510692 0.037 Uiso 1 1 calc R U . . .
H7B H 0.605816 0.353553 0.577083 0.037 Uiso 1 1 calc R U . . .
C8 C 0.54761(15) 0.39913(15) 0.65244(18) 0.0271(6) Uani 1 1 d . . . . .
C9 C 0.46926(14) 0.33614(14) 0.68889(17) 0.0222(5) Uani 1 1 d . . . . .
C10 C 0.43435(14) 0.34748(14) 0.76551(17) 0.0248(5) Uani 1 1 d . . . . .
H10 H 0.461394 0.397168 0.793073 0.030 Uiso 1 1 calc R U . . .
C11 C 0.60995(16) 0.4199(2) 0.7256(2) 0.0422(8) Uani 1 1 d . . . . .
H11A H 0.611944 0.373582 0.742875 0.063 Uiso 1 1 calc R U . . .
H11B H 0.597989 0.440805 0.780497 0.063 Uiso 1 1 calc R U . . .
H11C H 0.659995 0.458582 0.700381 0.063 Uiso 1 1 calc R U . . .
C12 C 0.54433(19) 0.47004(17) 0.6218(3) 0.0454(8) Uani 1 1 d . . . . .
H12A H 0.594512 0.508362 0.596557 0.068 Uiso 1 1 calc R U . . .
H12B H 0.531726 0.492040 0.675150 0.068 Uiso 1 1 calc R U . . .
H12C H 0.504637 0.455443 0.573997 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.866(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.378(3) . ?
N1 C4 1.369(3) . ?
N2 C6 1.354(3) . ?
N2 C9 1.350(3) . ?
C1 C2 1.413(3) . ?
C1 C10 1.386(3) 13_556 ?
C2 H2 0.9500 . ?
C2 C3 1.366(4) . ?
C3 C4 1.418(3) . ?
C4 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 C7 1.506(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.539(4) . ?
C8 C9 1.533(3) . ?
C8 C11 1.525(4) . ?
C8 C12 1.519(4) . ?
C9 C10 1.385(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 N1 H1 124.7 . . ?
C4 N1 H1 124.7 . . ?
C4 N1 C1 110.7(2) . . ?
C9 N2 C6 108.2(2) . . ?
N1 C1 C2 107.0(2) . . ?
N1 C1 C10 125.7(2) . 13_556 ?
C10 C1 C2 127.3(2) 13_556 . ?
C1 C2 H2 126.4 . . ?
C3 C2 C1 107.2(2) . . ?
C3 C2 H2 126.4 . . ?
C2 C3 Br1 126.72(19) . . ?
C2 C3 C4 109.6(2) . . ?
C4 C3 Br1 123.71(19) . . ?
N1 C4 C3 105.6(2) . . ?
N1 C4 C5 127.0(2) . . ?
C5 C4 C3 127.5(2) . . ?
C4 C5 H5 115.4 . . ?
C6 C5 C4 129.2(2) . . ?
C6 C5 H5 115.4 . . ?
N2 C6 C5 124.7(2) . . ?
N2 C6 C7 112.9(2) . . ?
C5 C6 C7 122.4(2) . . ?
C6 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C6 C7 C8 104.1(2) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C9 C8 C7 100.7(2) . . ?
C11 C8 C7 111.4(2) . . ?
C11 C8 C9 110.4(2) . . ?
C12 C8 C7 111.6(2) . . ?
C12 C8 C9 111.3(2) . . ?
C12 C8 C11 111.0(3) . . ?
N2 C9 C8 114.0(2) . . ?
N2 C9 C10 123.9(2) . . ?
C10 C9 C8 122.1(2) . . ?
C1 C10 H10 115.8 13_556 . ?
C9 C10 C1 128.4(2) . 13_556 ?
C9 C10 H10 115.8 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
Br1 C3 C4 N1 177.87(17) . . . . ?
Br1 C3 C4 C5 -3.0(4) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
N1 C4 C5 C6 -0.8(4) . . . . ?
N2 C6 C7 C8 0.2(3) . . . . ?
N2 C9 C10 C1 1.1(4) . . . 13_556 ?
C1 N1 C4 C3 0.8(3) . . . . ?
C1 N1 C4 C5 -178.4(2) . . . . ?
C1 C2 C3 Br1 -177.93(18) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 N1 -1.1(3) . . . . ?
C2 C3 C4 C5 178.0(2) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
C4 N1 C1 C2 -0.2(3) . . . . ?
C4 N1 C1 C10 -179.0(2) . . . 13_556 ?
C4 C5 C6 N2 -1.3(4) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C5 C6 C7 C8 179.3(2) . . . . ?
C6 N2 C9 C8 -0.4(3) . . . . ?
C6 N2 C9 C10 -180.0(2) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C6 C7 C8 C11 116.7(2) . . . . ?
C6 C7 C8 C12 -118.6(2) . . . . ?
C7 C8 C9 N2 0.5(3) . . . . ?
C7 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 C1 -178.5(2) . . . 13_556 ?
C9 N2 C6 C5 -179.0(2) . . . . ?
C9 N2 C6 C7 0.1(3) . . . . ?
C10 C1 C2 C3 178.3(2) 13_556 . . . ?
C11 C8 C9 N2 -117.3(2) . . . . ?
C11 C8 C9 C10 62.2(3) . . . . ?
C12 C8 C9 N2 118.9(3) . . . . ?
C12 C8 C9 C10 -61.5(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 65.0 3.3 ?
2 0.333 0.667 0.667 65.0 3.3 ?
3 0.667 0.333 0.333 65.0 3.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
