# 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 2024

####################################################################### 
# 
# 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_fgcupch0115_0mx
_database_code_depnum_ccdc_archive 'CCDC 2343474'
loop_
_audit_author_name
_audit_author_address
'Patrick Hillesheim'
;Ave Maria University
United States of America
;
_audit_update_record             
;
2024-03-26 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_audit_creation_date             2024-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H13 N2'
_chemical_formula_sum            'C7 H13 Br N2'
_chemical_formula_weight         205.10
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8003(4)
_cell_length_b                   17.1874(9)
_cell_length_c                   7.9486(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.531(2)
_cell_angle_gamma                90
_cell_volume                     910.28(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6319
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   0.717
_shelx_estimated_absorpt_T_min   0.372
_exptl_absorpt_coefficient_mu    4.450
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0855 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.6344.
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    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blocks
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0150
1.00 0.00 2.00 0.0510
1.00 -1.00 -2.00 0.1110
1.00 -1.00 1.00 0.0470
-1.00 2.00 0.00 0.0320
0.00 -1.00 0.00 0.0580
0.00 1.00 0.00 0.0380
-1.00 -2.00 0.00 0.0500

_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11610
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.922
_diffrn_reflns_theta_min         2.871
_diffrn_ambient_temperature      150.00
_diffrn_detector                 'Bruker PhotonII CPAD'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type            
;
charge-integrating pixel array detector (CPAD)
;
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest Eco diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   '1 kW fine focus sealed tube X-ray source'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1837
_reflns_number_total             2167
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.093
_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)+(0.0218P)²+0.6268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0597
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.86974(3) 0.62920(2) 0.23029(3) 0.03026(8) Uani 1 1 d . . . . .
N1 N 0.4250(3) 0.45066(10) 0.2683(2) 0.0263(4) Uani 1 1 d . . . . .
N3 N 0.4951(3) 0.34876(11) 0.4289(2) 0.0242(4) Uani 1 1 d . . . . .
C2 C 0.3483(3) 0.38469(12) 0.3179(3) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.6672(3) 0.39399(13) 0.4510(3) 0.0277(5) Uani 1 1 d . . . . .
H4 H 0.792616 0.382361 0.523492 0.033 Uiso 1 1 calc R U . . .
C5 C 0.6243(3) 0.45720(13) 0.3513(3) 0.0289(5) Uani 1 1 d . . . . .
H5 H 0.713310 0.498546 0.339621 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3161(4) 0.50793(14) 0.1476(3) 0.0354(5) Uani 1 1 d . . . . .
H6A H 0.265730 0.482834 0.036596 0.053 Uiso 1 1 calc R U . . .
H6B H 0.406741 0.550519 0.132426 0.053 Uiso 1 1 calc R U . . .
H6C H 0.202936 0.528654 0.193035 0.053 Uiso 1 1 calc R U . . .
C7 C 0.1384(3) 0.35775(15) 0.2608(3) 0.0361(5) Uani 1 1 d . . . . .
H7A H 0.131638 0.301507 0.279082 0.054 Uiso 1 1 calc R U . . .
H7B H 0.092908 0.369378 0.138505 0.054 Uiso 1 1 calc R U . . .
H7C H 0.051874 0.384571 0.327123 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4761(3) 0.27513(13) 0.5198(3) 0.0304(5) Uani 1 1 d . . . . .
H8A H 0.361502 0.245053 0.454839 0.036 Uiso 1 1 calc R U . . .
H8B H 0.447424 0.286839 0.634499 0.036 Uiso 1 1 calc R U . . .
C9 C 0.6642(4) 0.22640(15) 0.5409(3) 0.0367(5) Uani 1 1 d . . . . .
H9A H 0.697498 0.217254 0.428112 0.055 Uiso 1 1 calc R U . . .
H9B H 0.641907 0.176443 0.593467 0.055 Uiso 1 1 calc R U . . .
H9C H 0.775236 0.253886 0.614656 0.055 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
N1 C2 1.340(3) . ?
N1 C5 1.388(3) . ?
N1 C6 1.468(3) . ?
N3 C2 1.343(3) . ?
N3 C4 1.387(3) . ?
N3 C8 1.476(3) . ?
C2 C7 1.483(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.342(3) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.510(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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 N1 C5 109.24(19) . . ?
C2 N1 C6 125.8(2) . . ?
C5 N1 C6 125.0(2) . . ?
C2 N3 C4 108.84(18) . . ?
C2 N3 C8 126.12(18) . . ?
C4 N3 C8 124.97(18) . . ?
N1 C2 N3 107.48(19) . . ?
N1 C2 C7 125.6(2) . . ?
N3 C2 C7 126.9(2) . . ?
N3 C4 H4 126.3 . . ?
C5 C4 N3 107.5(2) . . ?
C5 C4 H4 126.3 . . ?
N1 C5 H5 126.5 . . ?
C4 C5 N1 106.9(2) . . ?
C4 C5 H5 126.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.2 . . ?
N3 C8 H8B 109.2 . . ?
N3 C8 C9 111.99(18) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
N3 C4 C5 N1 0.2(2) . . . . ?
C2 N1 C5 C4 0.3(2) . . . . ?
C2 N3 C4 C5 -0.6(2) . . . . ?
C2 N3 C8 C9 144.4(2) . . . . ?
C4 N3 C2 N1 0.8(2) . . . . ?
C4 N3 C2 C7 -178.5(2) . . . . ?
C4 N3 C8 C9 -38.7(3) . . . . ?
C5 N1 C2 N3 -0.7(2) . . . . ?
C5 N1 C2 C7 178.6(2) . . . . ?
C6 N1 C2 N3 -179.85(19) . . . . ?
C6 N1 C2 C7 -0.6(3) . . . . ?
C6 N1 C5 C4 179.5(2) . . . . ?
C8 N3 C2 N1 178.11(19) . . . . ?
C8 N3 C2 C7 -1.1(3) . . . . ?
C8 N3 C4 C5 -177.96(19) . . . . ?

_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_fgcupch0118_0m
_database_code_depnum_ccdc_archive 'CCDC 2343475'
loop_
_audit_author_name
_audit_author_address
'Patrick Hillesheim'
;Ave Maria University
United States of America
;
_audit_update_record             
;
2024-03-26 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_audit_creation_date             2024-03-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C7 H13 N2'
_chemical_formula_sum            'C7 H13 I N2'
_chemical_formula_weight         252.09
_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'
I I -0.4742 1.8119 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0499(4)
_cell_length_b                   7.8198(3)
_cell_length_c                   13.5789(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.8440(10)
_cell_angle_gamma                90
_cell_volume                     955.96(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.850
_shelx_estimated_absorpt_T_min   0.384
_exptl_absorpt_coefficient_mu    3.288
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0710 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.7318.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needles
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.1170
0.00 -1.00 0.00 0.1800
0.00 0.00 1.00 0.0140
0.00 0.00 -1.00 0.0350
-2.00 0.00 1.00 0.0150
2.00 0.00 -1.00 0.0230

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19287
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.595
_diffrn_reflns_theta_min         3.010
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type            
;
charge-integrating pixel array detector (CPAD)
;
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest Eco diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2731
_reflns_number_total             2932
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0216
_refine_ls_restrained_S_all      1.195
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0086P)²+1.0572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0439
_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
I1 I 0.23806(2) 0.17242(2) 0.57348(2) 0.02513(5) Uani 1 1 d . . . . .
N1 N 0.34383(18) 0.6657(2) 0.71412(12) 0.0214(3) Uani 1 1 d . . . . .
N3 N 0.11701(19) 0.5859(2) 0.72079(12) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.2133(2) 0.6432(2) 0.66014(14) 0.0198(3) Uani 1 1 d . . . . .
C4 C 0.1889(2) 0.5692(3) 0.81536(15) 0.0266(4) Uani 1 1 d . . . . .
H4 H 0.146398 0.530198 0.872446 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3305(2) 0.6190(3) 0.81081(15) 0.0255(4) Uani 1 1 d . . . . .
H5 H 0.406924 0.621552 0.864211 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4820(2) 0.7198(3) 0.67524(17) 0.0277(4) Uani 1 1 d . . . . .
H6A H 0.545730 0.779761 0.727961 0.033 Uiso 1 1 calc R U . . .
H6B H 0.458382 0.801215 0.620033 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5654(2) 0.5699(3) 0.63908(17) 0.0316(5) Uani 1 1 d . . . . .
H7A H 0.496470 0.496100 0.598155 0.047 Uiso 1 1 calc R U . . .
H7B H 0.611048 0.504832 0.695895 0.047 Uiso 1 1 calc R U . . .
H7C H 0.642922 0.611145 0.599596 0.047 Uiso 1 1 calc R U . . .
C8 C -0.0375(2) 0.5358(4) 0.69068(18) 0.0357(5) Uani 1 1 d . . . . .
H8A H -0.082667 0.617619 0.641889 0.054 Uiso 1 1 calc R U . . .
H8B H -0.093544 0.535086 0.748755 0.054 Uiso 1 1 calc R U . . .
H8C H -0.039360 0.421215 0.661334 0.054 Uiso 1 1 calc R U . . .
C9 C 0.1817(2) 0.6728(3) 0.55248(15) 0.0268(4) Uani 1 1 d . . . . .
H9A H 0.243803 0.766745 0.532432 0.040 Uiso 1 1 calc R U . . .
H9B H 0.076735 0.702600 0.537091 0.040 Uiso 1 1 calc R U . . .
H9C H 0.203748 0.568668 0.516564 0.040 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
N1 C2 1.337(2) . ?
N1 C5 1.380(3) . ?
N1 C6 1.469(3) . ?
N3 C2 1.336(3) . ?
N3 C4 1.385(3) . ?
N3 C8 1.470(3) . ?
C2 C9 1.479(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.347(3) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.503(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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 N1 C5 109.20(17) . . ?
C2 N1 C6 125.33(17) . . ?
C5 N1 C6 125.34(17) . . ?
C2 N3 C4 109.21(17) . . ?
C2 N3 C8 125.44(18) . . ?
C4 N3 C8 125.19(18) . . ?
N1 C2 C9 126.32(18) . . ?
N3 C2 N1 107.55(17) . . ?
N3 C2 C9 126.12(18) . . ?
N3 C4 H4 126.6 . . ?
C5 C4 N3 106.82(18) . . ?
C5 C4 H4 126.6 . . ?
N1 C5 H5 126.4 . . ?
C4 C5 N1 107.21(17) . . ?
C4 C5 H5 126.4 . . ?
N1 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
N1 C6 C7 111.51(17) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
N3 C4 C5 N1 0.1(2) . . . . ?
C2 N1 C5 C4 -0.7(2) . . . . ?
C2 N1 C6 C7 -86.3(2) . . . . ?
C2 N3 C4 C5 0.5(2) . . . . ?
C4 N3 C2 N1 -0.9(2) . . . . ?
C4 N3 C2 C9 177.93(19) . . . . ?
C5 N1 C2 N3 1.0(2) . . . . ?
C5 N1 C2 C9 -177.86(19) . . . . ?
C5 N1 C6 C7 89.1(2) . . . . ?
C6 N1 C2 N3 176.96(18) . . . . ?
C6 N1 C2 C9 -1.9(3) . . . . ?
C6 N1 C5 C4 -176.66(19) . . . . ?
C8 N3 C2 N1 -176.54(19) . . . . ?
C8 N3 C2 C9 2.3(3) . . . . ?
C8 N3 C4 C5 176.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
