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

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

data_UMD1369_a
_audit_block_doi                 10.5517/ccdc.csd.cc224grg
_database_code_depnum_ccdc_archive 'CCDC 1910925'
loop_
_audit_author_name
_audit_author_address
'James A Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2019-04-18 deposited with the CCDC.	2019-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 Br N3'
_chemical_formula_weight         284.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.2000(9)
_cell_length_b                   18.4716(17)
_cell_length_c                   7.3285(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.769(3)
_cell_angle_gamma                90
_cell_volume                     1371.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.15

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.978
_shelx_estimated_absorpt_T_min   0.422
_shelx_estimated_absorpt_T_max   0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.199
_exptl_absorpt_correction_T_max  0.259
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49382
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         25.404
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2515
_reflns_number_gt                2217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+2.3221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0147(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2515
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_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 0.76686(4) 0.41194(2) 0.28952(6) 0.0566(2) Uani 1 1 d . . . . .
N1 N 0.7969(3) 0.57506(16) 0.5717(4) 0.0451(7) Uani 1 1 d . . . . .
N2 N 0.6064(3) 0.61580(18) 0.4067(4) 0.0492(7) Uani 1 1 d . . . . .
N3 N 0.4229(4) 0.66474(19) 0.2452(5) 0.0584(9) Uani 1 1 d . . . . .
C1 C 0.9552(6) 0.8117(3) 0.4805(9) 0.0933(18) Uani 1 1 d . . . . .
H1A H 0.9781 0.8303 0.6024 0.140 Uiso 1 1 calc R U . . .
H1B H 0.8679 0.8275 0.4343 0.140 Uiso 1 1 calc R U . . .
H1C H 1.0171 0.8292 0.4018 0.140 Uiso 1 1 calc R U . . .
C2 C 0.9592(6) 0.7314(3) 0.4854(7) 0.0785(14) Uani 1 1 d . . . . .
H2A H 1.0388 0.7101 0.5317 0.094 Uiso 1 1 calc R U . . .
C3 C 0.8650(5) 0.6894(3) 0.4328(8) 0.0776(14) Uani 1 1 d . . . . .
H3A H 0.7845 0.7111 0.3930 0.093 Uiso 1 1 calc R U . . .
C4 C 0.8684(4) 0.6085(2) 0.4274(6) 0.0580(10) Uani 1 1 d . . . . .
H4A H 0.8290 0.5922 0.3076 0.070 Uiso 1 1 calc R U . . .
H4B H 0.9596 0.5925 0.4438 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8679(4) 0.5398(2) 0.7122(6) 0.0541(10) Uani 1 1 d . . . . .
H5A H 0.9591 0.5365 0.7142 0.065 Uiso 1 1 calc R U . . .
C6 C 0.8096(4) 0.5093(2) 0.8490(6) 0.0590(10) Uani 1 1 d . . . . .
H6A H 0.8595 0.4857 0.9455 0.071 Uiso 1 1 calc R U . . .
C7 C 0.6727(4) 0.5141(2) 0.8425(6) 0.0581(10) Uani 1 1 d . . . . .
H7A H 0.6306 0.4935 0.9358 0.070 Uiso 1 1 calc R U . . .
C8 C 0.6001(4) 0.5487(2) 0.7003(6) 0.0523(9) Uani 1 1 d . . . . .
H8A H 0.5089 0.5514 0.6972 0.063 Uiso 1 1 calc R U . . .
C9 C 0.6621(4) 0.58039(18) 0.5581(5) 0.0442(8) Uani 1 1 d . . . . .
C10 C 0.4809(4) 0.6308(2) 0.3904(5) 0.0496(9) Uani 1 1 d . . . . .
H10A H 0.4312 0.6173 0.4834 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4966(7) 0.6867(4) 0.0952(8) 0.106(2) Uani 1 1 d . . . . .
H11A H 0.5824 0.6645 0.1110 0.159 Uiso 1 1 calc R U . . .
H11B H 0.5062 0.7384 0.0959 0.159 Uiso 1 1 calc R U . . .
H11C H 0.4498 0.6716 -0.0198 0.159 Uiso 1 1 calc R U . . .
C12 C 0.2838(5) 0.6832(3) 0.2277(7) 0.0785(14) Uani 1 1 d . . . . .
H12A H 0.2439 0.6617 0.3268 0.118 Uiso 1 1 calc R U . . .
H12B H 0.2412 0.6654 0.1127 0.118 Uiso 1 1 calc R U . . .
H12C H 0.2742 0.7349 0.2320 0.118 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 C5 1.354(5) . ?
N1 C9 1.370(5) . ?
N1 C4 1.489(5) . ?
N2 C10 1.302(5) . ?
N2 C9 1.354(5) . ?
N3 C10 1.314(5) . ?
N3 C12 1.450(6) . ?
N3 C11 1.460(7) . ?
C1 C2 1.483(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.259(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.495(7) . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.348(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.394(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.365(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.407(5) . ?
C8 H8A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C9 122.2(3) . . ?
C5 N1 C4 118.5(3) . . ?
C9 N1 C4 119.4(3) . . ?
C10 N2 C9 119.4(3) . . ?
C10 N3 C12 121.7(4) . . ?
C10 N3 C11 121.3(4) . . ?
C12 N3 C11 117.0(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 126.2(6) . . ?
C3 C2 H2A 116.9 . . ?
C1 C2 H2A 116.9 . . ?
C2 C3 C4 127.2(6) . . ?
C2 C3 H3A 116.4 . . ?
C4 C3 H3A 116.4 . . ?
N1 C4 C3 112.4(4) . . ?
N1 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 N1 121.5(4) . . ?
C6 C5 H5A 119.2 . . ?
N1 C5 H5A 119.2 . . ?
C5 C6 C7 118.4(4) . . ?
C5 C6 H6A 120.8 . . ?
C7 C6 H6A 120.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C7 C8 C9 120.6(4) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
N2 C9 N1 114.5(3) . . ?
N2 C9 C8 128.7(4) . . ?
N1 C9 C8 116.8(3) . . ?
N2 C10 N3 121.3(4) . . ?
N2 C10 H10A 119.3 . . ?
N3 C10 H10A 119.3 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 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
C1 C2 C3 C4 176.6(5) . . . . ?
C5 N1 C4 C3 -111.0(4) . . . . ?
C9 N1 C4 C3 69.4(5) . . . . ?
C2 C3 C4 N1 108.1(6) . . . . ?
C9 N1 C5 C6 -1.6(6) . . . . ?
C4 N1 C5 C6 178.9(4) . . . . ?
N1 C5 C6 C7 0.7(6) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C6 C7 C8 C9 -0.2(7) . . . . ?
C10 N2 C9 N1 -172.5(3) . . . . ?
C10 N2 C9 C8 7.7(6) . . . . ?
C5 N1 C9 N2 -178.3(3) . . . . ?
C4 N1 C9 N2 1.3(5) . . . . ?
C5 N1 C9 C8 1.5(5) . . . . ?
C4 N1 C9 C8 -179.0(3) . . . . ?
C7 C8 C9 N2 179.1(4) . . . . ?
C7 C8 C9 N1 -0.6(6) . . . . ?
C9 N2 C10 N3 -179.6(4) . . . . ?
C12 N3 C10 N2 -178.5(4) . . . . ?
C11 N3 C10 N2 0.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5A Br1 0.93 2.96 3.832(4) 157.4 3_766
C6 H6A Br1 0.93 3.11 3.766(4) 129.1 1_556
C8 H8A Br1 0.93 2.91 3.823(4) 169.1 3_666
C10 H10A Br1 0.93 2.82 3.730(4) 167.1 3_666
C12 H12A Br1 0.96 3.14 4.038(6) 157.0 3_666

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_UMD1363_a
_audit_block_doi                 10.5517/ccdc.csd.cc224gvk
_database_code_depnum_ccdc_archive 'CCDC 1910928'
loop_
_audit_author_name
_audit_author_address
'James A Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2019-04-18 deposited with the CCDC.	2019-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N2'
_chemical_formula_weight         158.20

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4588(12)
_cell_length_b                   8.1981(17)
_cell_length_c                   8.3521(17)
_cell_angle_alpha                106.039(10)
_cell_angle_beta                 95.947(11)
_cell_angle_gamma                92.951(10)
_cell_volume                     421.25(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3120
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      25.34

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7413
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.084
_diffrn_reflns_theta_max         25.422
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1538
_reflns_number_gt                1212
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.1120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.39(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1538
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.50584(18) 0.50800(15) 0.75722(15) 0.0411(3) Uani 1 1 d . . . . .
N2 N 0.8310(2) 0.4268(2) 0.74170(19) 0.0625(5) Uani 1 1 d . . . . .
C1 C 0.3555(2) 0.6102(2) 0.8224(2) 0.0503(4) Uani 1 1 d . . . . .
H1A H 0.2168 0.5858 0.7747 0.060 Uiso 1 1 calc R U . . .
C2 C 0.4116(3) 0.7460(2) 0.9559(2) 0.0594(5) Uani 1 1 d . . . . .
H2A H 0.3110 0.8174 0.9991 0.071 Uiso 1 1 calc R U . . .
C3 C 0.6198(3) 0.7819(2) 1.0316(2) 0.0603(5) Uani 1 1 d . . . . .
H3A H 0.6557 0.8754 1.1250 0.072 Uiso 1 1 calc R U . . .
C4 C 0.7679(3) 0.6807(2) 0.9688(2) 0.0577(5) Uani 1 1 d . . . . .
H4A H 0.9052 0.7034 1.0202 0.069 Uiso 1 1 calc R U . . .
C5 C 0.7145(2) 0.5419(2) 0.8263(2) 0.0473(4) Uani 1 1 d . . . . .
C6 C 0.6932(3) 0.3199(2) 0.6192(2) 0.0595(5) Uani 1 1 d . . . . .
H6A H 0.7325 0.2263 0.5400 0.071 Uiso 1 1 calc R U . . .
C7 C 0.4919(2) 0.3623(2) 0.62296(19) 0.0458(4) Uani 1 1 d . . . . .
C8 C 0.2971(3) 0.2854(2) 0.5228(2) 0.0537(5) Uani 1 1 d . . . . .
H8A H 0.1774 0.3398 0.5504 0.064 Uiso 1 1 calc R U . . .
C9 C 0.2733(3) 0.1473(2) 0.3978(2) 0.0626(5) Uani 1 1 d . . . . .
H9A H 0.3935 0.0937 0.3702 0.075 Uiso 1 1 calc R U . . .
C10 C 0.0750(3) 0.0663(3) 0.2948(2) 0.0683(5) Uani 1 1 d . . . . .
H10A H 0.0891 0.0497 0.1782 0.103 Uiso 1 1 calc R U . . .
H10B H -0.0354 0.1386 0.3254 0.103 Uiso 1 1 calc R U . . .
H10C H 0.0426 -0.0418 0.3141 0.103 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 C1 1.372(2) . ?
N1 C7 1.386(2) . ?
N1 C5 1.3925(19) . ?
N2 C5 1.331(2) . ?
N2 C6 1.357(2) . ?
C1 C2 1.343(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.405(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.350(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.399(2) . ?
C4 H4A 0.9300 . ?
C6 C7 1.364(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.446(2) . ?
C8 C9 1.301(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.479(2) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 131.04(13) . . ?
C1 N1 C5 121.54(14) . . ?
C7 N1 C5 107.42(13) . . ?
C5 N2 C6 104.37(14) . . ?
C2 C1 N1 119.06(15) . . ?
C2 C1 H1A 120.5 . . ?
N1 C1 H1A 120.5 . . ?
C1 C2 C3 121.00(17) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 120.14(17) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 119.88(16) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
N2 C5 N1 110.77(14) . . ?
N2 C5 C4 130.87(15) . . ?
N1 C5 C4 118.33(15) . . ?
N2 C6 C7 113.83(16) . . ?
N2 C6 H6A 123.1 . . ?
C7 C6 H6A 123.1 . . ?
C6 C7 N1 103.61(14) . . ?
C6 C7 C8 133.14(16) . . ?
N1 C7 C8 123.24(14) . . ?
C9 C8 C7 126.15(17) . . ?
C9 C8 H8A 116.9 . . ?
C7 C8 H8A 116.9 . . ?
C8 C9 C10 126.83(18) . . ?
C8 C9 H9A 116.6 . . ?
C10 C9 H9A 116.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C7 N1 C1 C2 179.79(15) . . . . ?
C5 N1 C1 C2 0.0(2) . . . . ?
N1 C1 C2 C3 -1.5(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C6 N2 C5 N1 -0.29(18) . . . . ?
C6 N2 C5 C4 177.87(17) . . . . ?
C1 N1 C5 N2 -179.49(14) . . . . ?
C7 N1 C5 N2 0.67(17) . . . . ?
C1 N1 C5 C4 2.1(2) . . . . ?
C7 N1 C5 C4 -177.74(14) . . . . ?
C3 C4 C5 N2 179.31(18) . . . . ?
C3 C4 C5 N1 -2.7(2) . . . . ?
C5 N2 C6 C7 -0.2(2) . . . . ?
N2 C6 C7 N1 0.6(2) . . . . ?
N2 C6 C7 C8 -178.24(17) . . . . ?
C1 N1 C7 C6 179.44(15) . . . . ?
C5 N1 C7 C6 -0.74(16) . . . . ?
C1 N1 C7 C8 -1.6(3) . . . . ?
C5 N1 C7 C8 178.26(14) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
N1 C7 C8 C9 -178.52(17) . . . . ?
C7 C8 C9 C10 179.59(17) . . . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_UMD1749e_a
_database_code_depnum_ccdc_archive 'CCDC 1920095'
loop_
_audit_author_name
_audit_author_address
'James A Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 F3 N2'
_chemical_formula_weight         262.23

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.7552(7)
_cell_length_b                   9.5594(8)
_cell_length_c                   12.4421(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.316(2)
_cell_angle_gamma                90
_cell_volume                     1159.97(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9094
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.70

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42264
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.984
_diffrn_reflns_theta_max         25.729
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2203
_reflns_number_gt                2013
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+0.9899P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.215(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2203
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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_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
F1 F 0.41355(17) 0.3883(2) 0.43520(14) 0.0703(6) Uani 1 1 d . . . . .
F2 F 0.3007(2) 0.54780(16) 0.35279(13) 0.0698(6) Uani 1 1 d . . . . .
F3 F 0.22248(18) 0.34113(18) 0.35950(12) 0.0639(5) Uani 1 1 d . . . . .
N1 N 0.33277(16) 0.15555(17) 0.60562(12) 0.0275(4) Uani 1 1 d . . . . .
N2 N 0.18991(18) -0.01447(18) 0.55002(16) 0.0368(5) Uani 1 1 d . . . . .
C1 C 0.4541(2) 0.2107(2) 0.64519(16) 0.0340(5) Uani 1 1 d . . . . .
H1 H 0.4631 0.3085 0.6569 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5601(2) 0.1237(2) 0.66714(18) 0.0395(5) Uani 1 1 d . . . . .
H2 H 0.6446 0.1606 0.6940 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5462(2) -0.0223(2) 0.65041(17) 0.0386(5) Uani 1 1 d . . . . .
H3 H 0.6217 -0.0824 0.6658 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4266(2) -0.0769(2) 0.61269(17) 0.0346(5) Uani 1 1 d . . . . .
H4 H 0.4177 -0.1750 0.6024 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3145(2) 0.0129(2) 0.58857(15) 0.0296(5) Uani 1 1 d . . . . .
C6 C 0.1270(2) 0.1132(2) 0.54277(19) 0.0363(5) Uani 1 1 d . . . . .
H6 H 0.0353 0.1262 0.5174 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2107(2) 0.2193(2) 0.57602(16) 0.0307(5) Uani 1 1 d . . . . .
C8 C 0.18379(19) 0.3700(2) 0.59343(16) 0.0297(5) Uani 1 1 d . . . . .
C9 C 0.2171(2) 0.4746(2) 0.51954(16) 0.0312(5) Uani 1 1 d . . . . .
C10 C 0.1865(2) 0.6139(2) 0.54047(18) 0.0360(5) Uani 1 1 d . . . . .
H10 H 0.2081 0.6837 0.4893 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1251(2) 0.6514(2) 0.63467(19) 0.0419(6) Uani 1 1 d . . . . .
H11 H 0.1070 0.7471 0.6492 0.050 Uiso 1 1 calc R U . . .
C12 C 0.0896(2) 0.5494(2) 0.70862(19) 0.0433(6) Uani 1 1 d . . . . .
H12 H 0.0456 0.5744 0.7732 0.052 Uiso 1 1 calc R U . . .
C13 C 0.1189(2) 0.4115(2) 0.68698(18) 0.0369(5) Uani 1 1 d . . . . .
H13 H 0.0940 0.3420 0.7376 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2868(2) 0.4378(2) 0.41729(18) 0.0372(5) 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
F1 C14 1.337(3) . ?
F2 C14 1.332(3) . ?
F3 C14 1.321(3) . ?
N1 C1 1.376(3) . ?
N1 C7 1.380(2) . ?
N1 C5 1.391(2) . ?
N2 C5 1.323(3) . ?
N2 C6 1.368(3) . ?
C1 C2 1.351(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.353(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(3) . ?
C4 H4 0.9500 . ?
C6 C7 1.361(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.481(3) . ?
C8 C13 1.395(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.498(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 H13 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 C7 130.96(17) . . ?
C1 N1 C5 122.42(17) . . ?
C7 N1 C5 106.62(16) . . ?
C5 N2 C6 104.74(17) . . ?
C2 C1 N1 118.99(19) . . ?
C2 C1 H1 120.5 . . ?
N1 C1 H1 120.5 . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.65(19) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N2 C5 N1 111.25(17) . . ?
N2 C5 C4 130.92(19) . . ?
N1 C5 C4 117.82(18) . . ?
C7 C6 N2 112.35(18) . . ?
C7 C6 H6 123.8 . . ?
N2 C6 H6 123.8 . . ?
C6 C7 N1 105.04(17) . . ?
C6 C7 C8 131.49(19) . . ?
N1 C7 C8 123.06(17) . . ?
C13 C8 C9 117.48(19) . . ?
C13 C8 C7 118.92(18) . . ?
C9 C8 C7 123.59(19) . . ?
C10 C9 C8 120.39(19) . . ?
C10 C9 C14 119.20(19) . . ?
C8 C9 C14 120.41(18) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C8 122.4(2) . . ?
C12 C13 H13 118.8 . . ?
C8 C13 H13 118.8 . . ?
F3 C14 F2 106.1(2) . . ?
F3 C14 F1 105.62(19) . . ?
F2 C14 F1 105.86(19) . . ?
F3 C14 C9 114.04(18) . . ?
F2 C14 C9 112.37(18) . . ?
F1 C14 C9 112.17(18) . . ?

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
C7 N1 C1 C2 -179.4(2) . . . . ?
C5 N1 C1 C2 0.8(3) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C6 N2 C5 N1 -0.3(2) . . . . ?
C6 N2 C5 C4 -179.6(2) . . . . ?
C1 N1 C5 N2 -179.83(17) . . . . ?
C7 N1 C5 N2 0.3(2) . . . . ?
C1 N1 C5 C4 -0.4(3) . . . . ?
C7 N1 C5 C4 179.76(17) . . . . ?
C3 C4 C5 N2 178.9(2) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C5 N2 C6 C7 0.1(3) . . . . ?
N2 C6 C7 N1 0.1(2) . . . . ?
N2 C6 C7 C8 -172.5(2) . . . . ?
C1 N1 C7 C6 179.93(19) . . . . ?
C5 N1 C7 C6 -0.3(2) . . . . ?
C1 N1 C7 C8 -6.6(3) . . . . ?
C5 N1 C7 C8 173.17(18) . . . . ?
C6 C7 C8 C13 78.1(3) . . . . ?
N1 C7 C8 C13 -93.5(2) . . . . ?
C6 C7 C8 C9 -100.4(3) . . . . ?
N1 C7 C8 C9 88.1(3) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C10 178.82(19) . . . . ?
C13 C8 C9 C14 -179.94(18) . . . . ?
C7 C8 C9 C14 -1.5(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C14 C9 C10 C11 -178.6(2) . . . . ?
C9 C10 C11 C12 -1.9(4) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
C7 C8 C13 C12 -179.6(2) . . . . ?
C10 C9 C14 F3 -126.3(2) . . . . ?
C8 C9 C14 F3 54.0(3) . . . . ?
C10 C9 C14 F2 -5.4(3) . . . . ?
C8 C9 C14 F2 174.87(19) . . . . ?
C10 C9 C14 F1 113.7(2) . . . . ?
C8 C9 C14 F1 -66.0(3) . . . . ?

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.069

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_UMD1780g_a
_database_code_depnum_ccdc_archive 'CCDC 1922120'
loop_
_audit_author_name
_audit_author_address
'James A Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 Br N3 O'
_chemical_formula_weight         338.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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                   18.110(3)
_cell_length_b                   10.9556(18)
_cell_length_c                   17.217(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.622(5)
_cell_angle_gamma                90
_cell_volume                     3217.5(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      24.74

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.555
_shelx_estimated_absorpt_T_min   0.535
_shelx_estimated_absorpt_T_max   0.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39434
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_max         25.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2977
_reflns_number_gt                2305
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+2.6844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.40771(2) 0.30770(3) 0.55108(2) 0.05904(16) Uani 1 1 d . . . . .
O1 O 0.22685(17) 0.4170(2) 0.4780(2) 0.0865(9) Uani 1 1 d D . . . .
H1WB H 0.2719(17) 0.379(5) 0.486(4) 0.130 Uiso 1 1 d D U . . .
H1WA H 0.193(3) 0.357(3) 0.461(3) 0.130 Uiso 1 1 d D U . . .
N1 N 0.32470(14) 0.68487(19) 0.77341(15) 0.0431(6) Uani 1 1 d . . . . .
N2 N 0.24133(14) 0.7135(2) 0.64124(15) 0.0424(5) Uani 1 1 d . . . . .
N3 N 0.14860(14) 0.7314(2) 0.51269(16) 0.0501(6) Uani 1 1 d . . . . .
C1 C 0.32805(19) 0.9760(3) 0.73165(19) 0.0509(7) Uani 1 1 d . . . . .
H1A H 0.2902 0.9539 0.6820 0.061 Uiso 1 1 calc R U . . .
C2 C 0.3741(2) 1.0773(3) 0.7349(2) 0.0585(8) Uani 1 1 d . . . . .
H2A H 0.3675 1.1225 0.6873 0.070 Uiso 1 1 calc R U . . .
C3 C 0.42968(19) 1.1119(3) 0.8077(2) 0.0571(8) Uani 1 1 d . . . . .
H3A H 0.4606 1.1803 0.8094 0.069 Uiso 1 1 calc R U . . .
C4 C 0.43966(19) 1.0456(3) 0.8782(2) 0.0543(8) Uani 1 1 d . . . . .
H4A H 0.4773 1.0690 0.9276 0.065 Uiso 1 1 calc R U . . .
C5 C 0.39351(17) 0.9436(3) 0.87545(19) 0.0489(7) Uani 1 1 d . . . . .
H5A H 0.4000 0.8993 0.9234 0.059 Uiso 1 1 calc R U . . .
C6 C 0.33769(16) 0.9069(2) 0.80197(18) 0.0427(6) Uani 1 1 d . . . . .
C7 C 0.28933(18) 0.7942(2) 0.7992(2) 0.0485(7) Uani 1 1 d . . . . .
H7A H 0.2855 0.7798 0.8533 0.058 Uiso 1 1 calc R U . . .
H7B H 0.2368 0.8068 0.7608 0.058 Uiso 1 1 calc R U . . .
C8 C 0.38425(19) 0.6273(3) 0.8320(2) 0.0534(8) Uani 1 1 d . . . . .
H8A H 0.4007 0.6571 0.8857 0.064 Uiso 1 1 calc R U . . .
C9 C 0.4203(2) 0.5282(3) 0.8146(2) 0.0581(8) Uani 1 1 d . . . . .
H9A H 0.4610 0.4900 0.8554 0.070 Uiso 1 1 calc R U . . .
C10 C 0.39504(19) 0.4852(3) 0.7345(2) 0.0532(8) Uani 1 1 d . . . . .
H10A H 0.4189 0.4171 0.7211 0.064 Uiso 1 1 calc R U . . .
C11 C 0.33547(17) 0.5418(3) 0.67523(19) 0.0479(7) Uani 1 1 d . . . . .
H11A H 0.3189 0.5112 0.6217 0.057 Uiso 1 1 calc R U . . .
C12 C 0.29834(16) 0.6462(3) 0.69334(18) 0.0423(6) Uani 1 1 d . . . . .
C13 C 0.20380(16) 0.6699(3) 0.56770(19) 0.0448(7) Uani 1 1 d . . . . .
H13A H 0.2168 0.5926 0.5541 0.054 Uiso 1 1 calc R U . . .
C14 C 0.1242(2) 0.8510(3) 0.5307(3) 0.0784(11) Uani 1 1 d . . . . .
H14A H 0.1359 0.9107 0.4957 0.118 Uiso 1 1 calc R U . . .
H14B H 0.1518 0.8711 0.5874 0.118 Uiso 1 1 calc R U . . .
H14C H 0.0689 0.8505 0.5211 0.118 Uiso 1 1 calc R U . . .
C15 C 0.1032(2) 0.6772(3) 0.4339(2) 0.0689(10) Uani 1 1 d . . . . .
H15A H 0.1027 0.7315 0.3900 0.103 Uiso 1 1 calc R U . . .
H15B H 0.0504 0.6633 0.4326 0.103 Uiso 1 1 calc R U . . .
H15C H 0.1265 0.6009 0.4272 0.103 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
O1 H1WB 0.883(10) . ?
O1 H1WA 0.876(10) . ?
N1 C8 1.359(4) . ?
N1 C12 1.366(4) . ?
N1 C7 1.494(3) . ?
N2 C13 1.310(4) . ?
N2 C12 1.339(4) . ?
N3 C13 1.310(4) . ?
N3 C14 1.449(5) . ?
N3 C15 1.456(4) . ?
C1 C2 1.377(4) . ?
C1 C6 1.388(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.372(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.387(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.506(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.352(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.381(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.360(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.414(4) . ?
C11 H11A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1WB O1 H1WA 101(5) . . ?
C8 N1 C12 121.7(2) . . ?
C8 N1 C7 117.6(3) . . ?
C12 N1 C7 120.6(2) . . ?
C13 N2 C12 118.7(2) . . ?
C13 N3 C14 121.6(3) . . ?
C13 N3 C15 121.2(3) . . ?
C14 N3 C15 116.8(3) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 121.2(3) . . ?
N1 C7 C6 111.3(2) . . ?
N1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 N1 122.0(3) . . ?
C9 C8 H8A 119.0 . . ?
N1 C8 H8A 119.0 . . ?
C8 C9 C10 118.2(3) . . ?
C8 C9 H9A 120.9 . . ?
C10 C9 H9A 120.9 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
N2 C12 N1 115.8(2) . . ?
N2 C12 C11 127.9(3) . . ?
N1 C12 C11 116.3(3) . . ?
N3 C13 N2 122.2(3) . . ?
N3 C13 H13A 118.9 . . ?
N2 C13 H13A 118.9 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C6 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
C8 N1 C7 C6 81.7(3) . . . . ?
C12 N1 C7 C6 -97.4(3) . . . . ?
C5 C6 C7 N1 -94.7(3) . . . . ?
C1 C6 C7 N1 84.9(3) . . . . ?
C12 N1 C8 C9 -0.5(5) . . . . ?
C7 N1 C8 C9 -179.6(3) . . . . ?
N1 C8 C9 C10 -0.1(5) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C13 N2 C12 N1 -167.8(2) . . . . ?
C13 N2 C12 C11 13.6(4) . . . . ?
C8 N1 C12 N2 -177.7(3) . . . . ?
C7 N1 C12 N2 1.4(4) . . . . ?
C8 N1 C12 C11 1.1(4) . . . . ?
C7 N1 C12 C11 -179.8(2) . . . . ?
C10 C11 C12 N2 177.4(3) . . . . ?
C10 C11 C12 N1 -1.2(4) . . . . ?
C14 N3 C13 N2 -1.6(4) . . . . ?
C15 N3 C13 N2 -174.8(3) . . . . ?
C12 N2 C13 N3 -178.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A Br1 0.93 2.83 3.720(3) 159.7 6_566
C9 H9A Br1 0.93 3.11 4.006(3) 162.8 2_656
C13 H13A O1 0.93 2.37 3.266(4) 162.2 .
C15 H15C O1 0.96 2.66 3.546(5) 154.2 .
O1 H1WB Br1 0.883(10) 2.46(2) 3.313(3) 162(5) .
O1 H1WA Br1 0.876(10) 2.527(18) 3.381(3) 165(5) 7_556

_refine_diff_density_max         0.708
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_UMD1745H_B
_database_code_depnum_ccdc_archive 'CCDC 1920094'
loop_
_audit_author_name
_audit_author_address
'James A Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   22.620(5)
_cell_length_b                   3.9660(8)
_cell_length_c                   12.201(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1094.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6616
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      25.25

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.725
_shelx_estimated_absorpt_T_min   0.401
_shelx_estimated_absorpt_T_max   0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.458
_exptl_absorpt_correction_T_max  0.562
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III Cmos'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16352
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.339
_diffrn_reflns_theta_max         25.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1992
_reflns_number_gt                1780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. Basf 0.187
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.4132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0190(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.187(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1992
_refine_ls_number_parameters     147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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_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 0.22021(2) 0.47247(12) 0.30329(8) 0.0689(2) Uani 1 1 d . . . . .
N1 N 0.50110(15) 0.6917(8) 0.5341(2) 0.0343(7) Uani 1 1 d . . . . .
N2 N 0.5094(2) 0.9341(10) 0.6994(3) 0.0518(10) Uani 1 1 d . . . . .
C1 C 0.5222(2) 0.5283(10) 0.4420(4) 0.0427(10) Uani 1 1 d . . . . .
H1A H 0.4965 0.4620 0.3867 0.051 Uiso 1 1 calc R U . . .
C2 C 0.5801(2) 0.4670(12) 0.4336(4) 0.0531(12) Uani 1 1 d . . . . .
H2A H 0.5945 0.3568 0.3718 0.064 Uiso 1 1 calc R U . . .
C3 C 0.6199(2) 0.5656(12) 0.5164(5) 0.0553(12) Uani 1 1 d . . . . .
H3A H 0.6601 0.5230 0.5087 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5995(2) 0.7218(13) 0.6066(4) 0.0501(11) Uani 1 1 d . . . . .
H4A H 0.6257 0.7863 0.6614 0.060 Uiso 1 1 calc R U . . .
C5 C 0.53913(19) 0.7878(10) 0.6185(3) 0.0407(10) Uani 1 1 d . . . . .
C6 C 0.4523(2) 0.9275(12) 0.6664(4) 0.0478(11) Uani 1 1 d . . . . .
H6A H 0.4213 1.0147 0.7077 0.057 Uiso 1 1 calc R U . . .
C7 C 0.44485(19) 0.7806(10) 0.5668(3) 0.0376(9) Uani 1 1 d . . . . .
C8 C 0.39104(17) 0.7132(10) 0.5024(3) 0.0355(9) Uani 1 1 d . . . . .
C9 C 0.3419(2) 0.5793(11) 0.5542(3) 0.0441(10) Uani 1 1 d . . . . .
H9A H 0.3436 0.5330 0.6288 0.053 Uiso 1 1 calc R U . . .
C10 C 0.2902(2) 0.5130(11) 0.4971(4) 0.0469(11) Uani 1 1 d . . . . .
H10A H 0.2574 0.4244 0.5328 0.056 Uiso 1 1 calc R U . . .
C11 C 0.28853(19) 0.5805(11) 0.3869(4) 0.0431(10) Uani 1 1 d . . . . .
C12 C 0.33642(19) 0.7149(11) 0.3333(3) 0.0435(10) Uani 1 1 d . . . . .
H12A H 0.3343 0.7605 0.2586 0.052 Uiso 1 1 calc R U . . .
C13 C 0.38784(18) 0.7820(11) 0.3908(3) 0.0413(10) Uani 1 1 d . . . . .
H13A H 0.4203 0.8734 0.3547 0.050 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 C11 1.901(5) . ?
N1 C7 1.379(6) . ?
N1 C1 1.382(6) . ?
N1 C5 1.395(5) . ?
N2 C5 1.328(6) . ?
N2 C6 1.352(7) . ?
C1 C2 1.336(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.409(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.345(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.398(6) . ?
C4 H4A 0.9300 . ?
C6 C7 1.357(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.473(6) . ?
C8 C9 1.385(6) . ?
C8 C13 1.391(5) . ?
C9 C10 1.385(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.372(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.373(6) . ?
C12 C13 1.384(6) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?

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
C7 N1 C1 132.4(3) . . ?
C7 N1 C5 106.6(3) . . ?
C1 N1 C5 121.0(4) . . ?
C5 N2 C6 104.7(4) . . ?
C2 C1 N1 119.1(4) . . ?
C2 C1 H1A 120.4 . . ?
N1 C1 H1A 120.4 . . ?
C1 C2 C3 121.4(5) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
N2 C5 N1 110.8(4) . . ?
N2 C5 C4 130.9(4) . . ?
N1 C5 C4 118.3(4) . . ?
N2 C6 C7 113.2(4) . . ?
N2 C6 H6A 123.4 . . ?
C7 C6 H6A 123.4 . . ?
C6 C7 N1 104.7(4) . . ?
C6 C7 C8 131.2(4) . . ?
N1 C7 C8 124.1(3) . . ?
C9 C8 C13 118.7(4) . . ?
C9 C8 C7 119.3(4) . . ?
C13 C8 C7 122.0(4) . . ?
C8 C9 C10 121.4(4) . . ?
C8 C9 H9A 119.3 . . ?
C10 C9 H9A 119.3 . . ?
C11 C10 C9 118.6(4) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C10 C11 C12 121.4(4) . . ?
C10 C11 Br1 120.3(3) . . ?
C12 C11 Br1 118.2(3) . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C12 C13 C8 120.2(4) . . ?
C12 C13 H13A 119.9 . . ?
C8 C13 H13A 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C2 -178.1(4) . . . . ?
C5 N1 C1 C2 -1.0(6) . . . . ?
N1 C1 C2 C3 -0.1(7) . . . . ?
C1 C2 C3 C4 0.7(8) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C6 N2 C5 N1 0.6(5) . . . . ?
C6 N2 C5 C4 -179.7(5) . . . . ?
C7 N1 C5 N2 -1.0(5) . . . . ?
C1 N1 C5 N2 -178.8(4) . . . . ?
C7 N1 C5 C4 179.2(4) . . . . ?
C1 N1 C5 C4 1.5(6) . . . . ?
C3 C4 C5 N2 179.5(5) . . . . ?
C3 C4 C5 N1 -0.8(7) . . . . ?
C5 N2 C6 C7 0.1(5) . . . . ?
N2 C6 C7 N1 -0.7(5) . . . . ?
N2 C6 C7 C8 178.2(4) . . . . ?
C1 N1 C7 C6 178.4(4) . . . . ?
C5 N1 C7 C6 1.0(4) . . . . ?
C1 N1 C7 C8 -0.6(7) . . . . ?
C5 N1 C7 C8 -178.0(4) . . . . ?
C6 C7 C8 C9 -44.8(7) . . . . ?
N1 C7 C8 C9 133.9(4) . . . . ?
C6 C7 C8 C13 134.8(5) . . . . ?
N1 C7 C8 C13 -46.6(6) . . . . ?
C13 C8 C9 C10 0.1(6) . . . . ?
C7 C8 C9 C10 179.7(4) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C9 C10 C11 Br1 176.7(3) . . . . ?
C10 C11 C12 C13 0.5(7) . . . . ?
Br1 C11 C12 C13 -177.0(3) . . . . ?
C11 C12 C13 C8 0.1(7) . . . . ?
C9 C8 C13 C12 -0.4(6) . . . . ?
C7 C8 C13 C12 180.0(4) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_UMD1750c_a
_database_code_depnum_ccdc_archive 'CCDC 1920096'
loop_
_audit_author_name
_audit_author_address
'James A Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Cl2 F N3 O'
_chemical_formula_weight         346.22

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4862(9)
_cell_length_b                   10.3569(12)
_cell_length_c                   10.6667(12)
_cell_angle_alpha                117.555(3)
_cell_angle_beta                 93.859(4)
_cell_angle_gamma                95.336(4)
_cell_volume                     821.07(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.70

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.410
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34369
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.050
_diffrn_reflns_theta_max         25.752
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3136
_reflns_number_gt                2758
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.5434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.01240(6) 0.35923(6) 0.63850(6) 0.04962(19) Uani 1 1 d . . . . .
Cl2 Cl 0.07901(6) 0.27596(5) 1.10343(6) 0.04332(18) Uani 1 1 d . . . . .
F1 F 0.36359(15) -0.00946(14) 0.59249(12) 0.0448(3) Uani 1 1 d . . . . .
O1W O 0.1972(2) -0.0308(2) 0.9244(2) 0.0495(4) Uani 1 1 d . . . . .
H1WB H 0.158(4) 0.045(4) 0.974(3) 0.067(9) Uiso 1 1 d . . . . .
H1WA H 0.134(4) -0.091(4) 0.912(3) 0.065(10) Uiso 1 1 d . . . . .
N1 N 0.40573(17) 0.27585(15) 0.82712(14) 0.0252(3) Uani 1 1 d . . . . .
N2 N 0.43367(17) 0.44720(16) 0.74773(15) 0.0279(3) Uani 1 1 d . . . . .
N3 N 0.4602(2) 0.62992(18) 0.68191(18) 0.0376(4) Uani 1 1 d . . . . .
C1 C 0.0879(2) 0.2130(2) 0.5417(2) 0.0324(4) Uani 1 1 d . . . . .
C2 C 0.0526(2) 0.1407(3) 0.3949(2) 0.0413(5) Uani 1 1 d . . . . .
H2A H -0.0218 0.1734 0.3491 0.050 Uiso 1 1 calc R U . . .
C3 C 0.1268(2) 0.0202(2) 0.3155(2) 0.0425(5) Uani 1 1 d . . . . .
H3A H 0.1048 -0.0291 0.2145 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2326(2) -0.0290(2) 0.3821(2) 0.0380(5) Uani 1 1 d . . . . .
H4A H 0.2830 -0.1125 0.3283 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2632(2) 0.0459(2) 0.5282(2) 0.0317(4) Uani 1 1 d . . . . .
C6 C 0.1971(2) 0.17011(19) 0.61348(18) 0.0269(4) Uani 1 1 d . . . . .
C7 C 0.2333(2) 0.2476(2) 0.77351(18) 0.0290(4) Uani 1 1 d . . . . .
H7A H 0.1909 0.3427 0.8117 0.035 Uiso 1 1 calc R U . . .
H7B H 0.1765 0.1873 0.8109 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4588(2) 0.1987(2) 0.89198(18) 0.0314(4) Uani 1 1 d . . . . .
H8A H 0.3866 0.1252 0.8958 0.038 Uiso 1 1 calc R U . . .
C9 C 0.6127(2) 0.2246(2) 0.95118(19) 0.0344(4) Uani 1 1 d . . . . .
H9A H 0.6487 0.1701 0.9960 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7163(2) 0.3329(2) 0.94474(19) 0.0330(4) Uani 1 1 d . . . . .
H10A H 0.8240 0.3539 0.9870 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6648(2) 0.40958(19) 0.87816(19) 0.0295(4) Uani 1 1 d . . . . .
H11A H 0.7374 0.4824 0.8736 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5044(2) 0.38139(17) 0.81598(16) 0.0236(3) Uani 1 1 d . . . . .
C13 C 0.5193(2) 0.5558(2) 0.74069(19) 0.0314(4) Uani 1 1 d . . . . .
H13A H 0.6285 0.5813 0.7799 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2944(3) 0.5989(4) 0.6215(4) 0.0691(8) Uani 1 1 d . . . . .
H14A H 0.2607 0.4924 0.5723 0.104 Uiso 1 1 calc R U . . .
H14B H 0.2821 0.6373 0.5535 0.104 Uiso 1 1 calc R U . . .
H14C H 0.2284 0.6461 0.6979 0.104 Uiso 1 1 calc R U . . .
C15 C 0.5557(4) 0.7537(3) 0.6810(3) 0.0670(8) Uani 1 1 d . . . . .
H15A H 0.6659 0.7625 0.7213 0.100 Uiso 1 1 calc R U . . .
H15B H 0.5116 0.8443 0.7383 0.100 Uiso 1 1 calc R U . . .
H15C H 0.5540 0.7375 0.5828 0.100 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
Cl1 C1 1.731(2) . ?
F1 C5 1.379(2) . ?
O1W H1WB 0.84(3) . ?
O1W H1WA 0.74(3) . ?
N1 C8 1.363(2) . ?
N1 C12 1.369(2) . ?
N1 C7 1.486(2) . ?
N2 C13 1.316(2) . ?
N2 C12 1.353(2) . ?
N3 C13 1.307(2) . ?
N3 C14 1.449(3) . ?
N3 C15 1.456(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.383(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.374(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.385(3) . ?
C6 C7 1.506(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.357(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.390(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.368(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.416(2) . ?
C11 H11A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
H1WB O1W H1WA 104(3) . . ?
C8 N1 C12 122.12(15) . . ?
C8 N1 C7 117.97(15) . . ?
C12 N1 C7 119.85(14) . . ?
C13 N2 C12 118.03(15) . . ?
C13 N3 C14 121.98(18) . . ?
C13 N3 C15 121.52(19) . . ?
C14 N3 C15 116.42(18) . . ?
C2 C1 C6 122.56(18) . . ?
C2 C1 Cl1 118.07(16) . . ?
C6 C1 Cl1 119.35(14) . . ?
C3 C2 C1 119.18(19) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C4 C3 C2 120.38(18) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C3 118.28(19) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
C4 C5 F1 117.11(17) . . ?
C4 C5 C6 124.19(19) . . ?
F1 C5 C6 118.68(16) . . ?
C5 C6 C1 115.33(16) . . ?
C5 C6 C7 122.15(17) . . ?
C1 C6 C7 122.41(16) . . ?
N1 C7 C6 114.27(14) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 N1 121.39(17) . . ?
C9 C8 H8A 119.3 . . ?
N1 C8 H8A 119.3 . . ?
C8 C9 C10 118.42(17) . . ?
C8 C9 H9A 120.8 . . ?
C10 C9 H9A 120.8 . . ?
C11 C10 C9 120.66(17) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 120.61(17) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
N2 C12 N1 114.89(15) . . ?
N2 C12 C11 128.33(16) . . ?
N1 C12 C11 116.78(15) . . ?
N3 C13 N2 122.63(17) . . ?
N3 C13 H13A 118.7 . . ?
N2 C13 H13A 118.7 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C6 C1 C2 C3 0.7(3) . . . . ?
Cl1 C1 C2 C3 -177.65(15) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 F1 177.08(17) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C1 3.1(3) . . . . ?
F1 C5 C6 C1 -175.40(15) . . . . ?
C4 C5 C6 C7 179.41(17) . . . . ?
F1 C5 C6 C7 0.9(3) . . . . ?
C2 C1 C6 C5 -2.7(3) . . . . ?
Cl1 C1 C6 C5 175.64(13) . . . . ?
C2 C1 C6 C7 -178.99(17) . . . . ?
Cl1 C1 C6 C7 -0.7(2) . . . . ?
C8 N1 C7 C6 -110.56(17) . . . . ?
C12 N1 C7 C6 72.2(2) . . . . ?
C5 C6 C7 N1 47.9(2) . . . . ?
C1 C6 C7 N1 -136.06(17) . . . . ?
C12 N1 C8 C9 1.1(3) . . . . ?
C7 N1 C8 C9 -176.03(16) . . . . ?
N1 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C13 N2 C12 N1 176.04(14) . . . . ?
C13 N2 C12 C11 -2.9(3) . . . . ?
C8 N1 C12 N2 179.54(14) . . . . ?
C7 N1 C12 N2 -3.4(2) . . . . ?
C8 N1 C12 C11 -1.4(2) . . . . ?
C7 N1 C12 C11 175.71(14) . . . . ?
C10 C11 C12 N2 179.38(16) . . . . ?
C10 C11 C12 N1 0.4(2) . . . . ?
C14 N3 C13 N2 0.8(3) . . . . ?
C15 N3 C13 N2 177.3(2) . . . . ?
C12 N2 C13 N3 -177.33(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A Cl1 0.99 2.52 3.0567(19) 114.0 .
C8 H8A O1W 0.95 2.31 3.252(3) 173.2 .
C13 H13A Cl2 0.95 2.66 3.588(2) 164.3 2_667
C11 H11A Cl2 0.95 2.72 3.6612(19) 170.4 2_667
C9 H9A O1W 0.95 2.42 3.343(3) 164.2 2_657
C15 H15A Cl2 0.98 2.94 3.855(3) 155.7 2_667
C14 H14A Cl1 0.98 2.88 3.501(3) 122.1 .
C14 H14B Cl1 0.98 2.98 3.744(3) 135.6 2_566
O1W H1WB Cl2 0.84(3) 2.33(3) 3.159(2) 171(3) .
O1W H1WA Cl2 0.74(3) 2.44(4) 3.183(2) 174(3) 2_557

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.065

_shelxl_version_number           2014/6

