# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

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

data_2118mg16
_database_code_depnum_ccdc_archive 'CCDC 2176281'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_2118mg16            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: theta limit set by dual source diffractometer
;
# Added during the CSD deposition process: Wednesday 01 June 2022 09:38 AM
# end Validation Reply Form


_audit_creation_date             2022-05-30T15:54:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C28 H36 N2'
_chemical_formula_weight         400.59

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2887(6)
_cell_length_b                   9.7101(10)
_cell_length_c                   10.8010(14)
_cell_angle_alpha                73.723(11)
_cell_angle_beta                 77.522(10)
_cell_angle_gamma                79.838(8)
_cell_volume                     613.42(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    520
_cell_measurement_theta_min      4.78
_cell_measurement_theta_max      59.73
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             218

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      0.04854
_diffrn_orient_matrix_ub_12      0.058324
_diffrn_orient_matrix_ub_13      -0.150052
_diffrn_orient_matrix_ub_21      -0.05242
_diffrn_orient_matrix_ub_22      0.156011
_diffrn_orient_matrix_ub_23      0.015469
_diffrn_orient_matrix_ub_31      0.242536
_diffrn_orient_matrix_ub_32      0.000579
_diffrn_orient_matrix_ub_33      0.005625
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_number            3087
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.332
_diffrn_reflns_theta_max         61.543
_diffrn_reflns_theta_full        61.543
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             3087
_reflns_number_gt                1672
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3087
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_restrained_S_all      0.813
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C3 C 0.4850(4) 0.3701(3) 0.1737(2) 0.0366(7) Uani 1 1 d . . . . .
C11 C 0.5643(4) 0.4262(3) 0.0279(2) 0.0368(6) Uani 1 1 d . . . . .
H11 H 0.721111 0.441906 0.016117 0.044 Uiso 1 1 calc R U . . .
C6 C 0.3359(5) 0.2683(3) 0.4478(3) 0.0387(7) Uani 1 1 d . . . . .
N1 N 1.0742(5) 0.1640(3) 0.0223(3) 0.0660(8) Uani 1 1 d . . . . .
C4 C 0.2832(5) 0.3189(3) 0.2228(3) 0.0476(8) Uani 1 1 d . . . . .
H4 H 0.191546 0.318347 0.16361 0.057 Uiso 1 1 calc R U . . .
C12 C 0.5585(5) 0.3172(3) -0.0485(3) 0.0444(7) Uani 1 1 d . . . . .
H12A H 0.629756 0.353897 -0.140426 0.053 Uiso 1 1 calc R U . . .
H12B H 0.403316 0.310631 -0.048932 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2124(5) 0.2686(3) 0.3561(3) 0.0481(8) Uani 1 1 d . . . . .
H5 H 0.074034 0.233075 0.385745 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6711(4) 0.1646(3) 0.0052(3) 0.0499(8) Uani 1 1 d . . . . .
H13A H 0.588311 0.121873 0.092633 0.06 Uiso 1 1 calc R U . . .
H13B H 0.667426 0.103258 -0.053512 0.06 Uiso 1 1 calc R U . . .
C2 C 0.6090(5) 0.3696(3) 0.2654(3) 0.0497(8) Uani 1 1 d . . . . .
H2 H 0.74803 0.404282 0.235906 0.06 Uiso 1 1 calc R U . . .
C7 C 0.2519(5) 0.2154(3) 0.5947(3) 0.0476(8) Uani 1 1 d . . . . .
C1 C 0.5366(5) 0.3201(4) 0.3983(3) 0.0527(8) Uani 1 1 d . . . . .
H1 H 0.627405 0.321718 0.457614 0.063 Uiso 1 1 calc R U . . .
C14 C 0.8932(6) 0.1645(3) 0.0158(3) 0.0506(8) Uani 1 1 d . . . . .
C8 C 0.4312(6) 0.1872(5) 0.6752(3) 0.0888(14) Uani 1 1 d . . . . .
H8A H 0.499687 0.275461 0.657669 0.133 Uiso 1 1 calc R U . . .
H8B H 0.368116 0.157888 0.768559 0.133 Uiso 1 1 calc R U . . .
H8C H 0.54213 0.109829 0.651719 0.133 Uiso 1 1 calc R U . . .
C9 C 0.0751(6) 0.3326(5) 0.6364(3) 0.0964(15) Uani 1 1 d . . . . .
H9A H -0.042028 0.351674 0.584673 0.145 Uiso 1 1 calc R U . . .
H9B H 0.013857 0.299443 0.729606 0.145 Uiso 1 1 calc R U . . .
H9C H 0.140683 0.421527 0.621433 0.145 Uiso 1 1 calc R U . . .
C10 C 0.1499(8) 0.0763(5) 0.6246(4) 0.1016(16) Uani 1 1 d . . . . .
H10A H 0.032799 0.091867 0.573406 0.152 Uiso 1 1 calc R U . . .
H10B H 0.262573 -0.000315 0.60137 0.152 Uiso 1 1 calc R U . . .
H10C H 0.08856 0.047745 0.71821 0.152 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C3 C2 1.385(4) . ?
C3 C4 1.387(4) . ?
C3 C11 1.516(4) . ?
C11 C12 1.523(4) . ?
C11 C11 1.546(5) 2_665 ?
C6 C5 1.383(4) . ?
C6 C1 1.384(4) . ?
C6 C7 1.529(4) . ?
N1 C14 1.155(4) . ?
C4 C5 1.385(4) . ?
C12 C13 1.535(4) . ?
C13 C14 1.425(4) . ?
C2 C1 1.382(4) . ?
C7 C8 1.512(4) . ?
C7 C10 1.520(5) . ?
C7 C9 1.536(5) . ?

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 C3 C4 116.3(2) . . ?
C2 C3 C11 121.7(2) . . ?
C4 C3 C11 122.0(2) . . ?
C3 C11 C12 112.2(2) . . ?
C3 C11 C11 111.5(3) . 2_665 ?
C12 C11 C11 111.2(3) . 2_665 ?
C5 C6 C1 116.0(2) . . ?
C5 C6 C7 121.4(3) . . ?
C1 C6 C7 122.6(3) . . ?
C5 C4 C3 121.4(3) . . ?
C11 C12 C13 114.8(2) . . ?
C6 C5 C4 122.4(3) . . ?
C14 C13 C12 112.5(2) . . ?
C1 C2 C3 122.0(3) . . ?
C8 C7 C10 107.9(3) . . ?
C8 C7 C6 112.6(3) . . ?
C10 C7 C6 110.8(3) . . ?
C8 C7 C9 108.9(3) . . ?
C10 C7 C9 108.8(3) . . ?
C6 C7 C9 107.8(2) . . ?
C2 C1 C6 121.9(3) . . ?
N1 C14 C13 178.8(3) . . ?



# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_2214mg14
_database_code_depnum_ccdc_archive 'CCDC 2176286'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_2214mg14            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: theta limit set by dual source diffractometer
;
# Added during the CSD deposition process: Wednesday 01 June 2022 09:38 AM
# end Validation Reply Form


_audit_creation_date             2022-05-30T14:50:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C14 H12 Br N'
_chemical_formula_weight         274.16
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_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                   11.5971(6)
_cell_length_b                   17.1790(10)
_cell_length_c                   5.9922(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1193.81(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    194(2)
_cell_measurement_reflns_used    1171
_cell_measurement_theta_min      4.6
_cell_measurement_theta_max      61.34
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.471
_shelx_estimated_absorpt_T_max   0.917

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      194(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      0.091467
_diffrn_orient_matrix_ub_12      0.064391
_diffrn_orient_matrix_ub_13      0.026688
_diffrn_orient_matrix_ub_21      -0.090944
_diffrn_orient_matrix_ub_22      0.061894
_diffrn_orient_matrix_ub_23      -0.060112
_diffrn_orient_matrix_ub_31      -0.031806
_diffrn_orient_matrix_ub_32      0.008157
_diffrn_orient_matrix_ub_33      0.248495
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_number            2736
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.6
_diffrn_reflns_theta_max         61.486
_diffrn_reflns_theta_full        61.486
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.745
_diffrn_reflns_point_group_measured_fraction_max 0.745
_reflns_Friedel_fraction_full    0.43
_reflns_Friedel_fraction_max     0.43
_reflns_Friedel_coverage         0.346
_reflns_number_total             1382
_reflns_number_gt                1246
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1382
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.7673(5) 0.4442(4) 0.2398(10) 0.0364(14) Uani 1 1 d . . . . .
H1 H 0.839889 0.453798 0.171549 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7422(5) 0.4769(4) 0.4493(10) 0.0363(14) Uani 1 1 d . . . . .
H2 H 0.798408 0.507542 0.523833 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6370(4) 0.4645(3) 0.5460(10) 0.0338(12) Uani 1 1 d . . . . .
H3 H 0.62057 0.487304 0.686888 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5532(4) 0.4189(3) 0.4411(9) 0.0278(12) Uani 1 1 d . . . . .
C5 C 0.5780(5) 0.3845(3) 0.2293(8) 0.0292(13) Uani 1 1 d . . . . .
C6 C 0.6882(4) 0.3992(3) 0.1350(13) 0.0361(12) Uani 1 1 d . . . . .
H6 H 0.707005 0.376763 -0.005335 0.043 Uiso 1 1 calc R U . . .
C7 C 0.4430(4) 0.4043(3) 0.5378(10) 0.0309(12) Uani 1 1 d . . . . .
H7 H 0.425212 0.426571 0.678686 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3627(5) 0.3594(3) 0.4346(9) 0.0301(12) Uani 1 1 d . . . . .
C9 C 0.3897(5) 0.3248(3) 0.2258(9) 0.0366(14) Uani 1 1 d . . . . .
H9 H 0.334319 0.29282 0.153459 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4939(4) 0.3370(3) 0.1288(12) 0.0373(14) Uani 1 1 d . . . . .
H10 H 0.510512 0.31281 -0.010151 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2469(4) 0.3469(3) 0.5454(10) 0.0309(12) Uani 1 1 d . . . . .
H11 H 0.242528 0.382082 0.678015 0.037 Uiso 1 1 calc R U . . .
C12 C 0.1447(5) 0.3636(5) 0.3992(11) 0.0498(17) Uani 1 1 d . . . . .
H12A H 0.152541 0.332749 0.260578 0.06 Uiso 1 1 calc R U . . .
H12B H 0.14703 0.419303 0.356597 0.06 Uiso 1 1 calc R U . . .
C13 C 0.0263(6) 0.3465(5) 0.5008(13) 0.0550(19) Uani 1 1 d . . . . .
H13A H -0.034501 0.362952 0.394943 0.066 Uiso 1 1 calc R U . . .
H13B H 0.018486 0.289712 0.524467 0.066 Uiso 1 1 calc R U . . .
C14 C 0.0097(5) 0.3869(5) 0.7139(14) 0.057(2) Uani 1 1 d . . . . .
Br1 Br 0.24166(5) 0.23796(3) 0.6542(3) 0.0514(3) Uani 1 1 d . . . . .
N1 N -0.0008(5) 0.4179(6) 0.8772(16) 0.083(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C6 1.355(9) . ?
C1 C2 1.405(9) . ?
C2 C3 1.367(8) . ?
C3 C4 1.398(8) . ?
C4 C7 1.425(8) . ?
C4 C5 1.429(8) . ?
C5 C10 1.407(8) . ?
C5 C6 1.420(8) . ?
C7 C8 1.357(8) . ?
C8 C9 1.420(8) . ?
C8 C11 1.513(7) . ?
C9 C10 1.358(8) . ?
C11 C12 1.502(8) . ?
C11 Br1 1.983(5) . ?
C12 C13 1.530(10) . ?
C13 C14 1.466(12) . ?
C14 N1 1.121(11) . ?

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
C6 C1 C2 120.1(5) . . ?
C3 C2 C1 120.1(6) . . ?
C2 C3 C4 121.1(6) . . ?
C3 C4 C7 122.6(5) . . ?
C3 C4 C5 119.4(5) . . ?
C7 C4 C5 118.0(5) . . ?
C10 C5 C6 123.8(5) . . ?
C10 C5 C4 118.7(5) . . ?
C6 C5 C4 117.5(5) . . ?
C1 C6 C5 121.7(6) . . ?
C8 C7 C4 122.0(5) . . ?
C7 C8 C9 119.2(5) . . ?
C7 C8 C11 119.3(5) . . ?
C9 C8 C11 121.5(5) . . ?
C10 C9 C8 120.6(6) . . ?
C9 C10 C5 121.5(6) . . ?
C12 C11 C8 114.7(5) . . ?
C12 C11 Br1 110.4(4) . . ?
C8 C11 Br1 107.8(4) . . ?
C11 C12 C13 116.0(5) . . ?
C14 C13 C12 112.0(7) . . ?
N1 C14 C13 178.7(8) . . ?



# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate and petroleum ether'
####################################################################### 
# 
# 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_2208mg15
_database_code_depnum_ccdc_archive 'CCDC 2176284'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_2208mg15            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: theta limit set by dual source diffractometer
;
# Added during the CSD deposition process: Wednesday 01 June 2022 09:38 AM
# end Validation Reply Form


_audit_creation_date             2022-05-30T14:21:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C10 H9 Br2 N'
_chemical_formula_weight         303

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.3061(2)
_cell_length_b                   13.0601(4)
_cell_length_c                   13.0615(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.138(4)
_cell_angle_gamma                90
_cell_volume                     1062.07(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    2105
_cell_measurement_theta_min      4.8
_cell_measurement_theta_max      61.39
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      0.204999
_diffrn_orient_matrix_ub_12      -0.019926
_diffrn_orient_matrix_ub_13      -0.047349
_diffrn_orient_matrix_ub_21      0.138506
_diffrn_orient_matrix_ub_22      0.02408
_diffrn_orient_matrix_ub_23      0.105335
_diffrn_orient_matrix_ub_31      -0.00678
_diffrn_orient_matrix_ub_32      -0.1137
_diffrn_orient_matrix_ub_33      0.030564
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_number            4137
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.819
_diffrn_reflns_theta_max         61.704
_diffrn_reflns_theta_full        61.704
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             1645
_reflns_number_gt                1457
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²+0.4958P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1645
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.028
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.083

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.5359(6) 0.6507(3) 0.4559(3) 0.0312(8) Uani 1 1 d . . . . .
H1A H 0.408379 0.695949 0.446372 0.037 Uiso 1 1 calc R U . . .
H1B H 0.48367 0.579136 0.44899 0.037 Uiso 1 1 calc R U . . .
C2 C 0.6561(6) 0.6656(3) 0.5648(3) 0.0273(8) Uani 1 1 d . . . . .
H2 H 0.785548 0.620275 0.574619 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5268(6) 0.6440(3) 0.6499(3) 0.0263(8) Uani 1 1 d . . . . .
C4 C 0.3313(6) 0.6915(3) 0.6529(3) 0.0320(8) Uani 1 1 d . . . . .
H4 H 0.273569 0.736649 0.598611 0.038 Uiso 1 1 calc R U . . .
C5 C 0.2185(6) 0.6738(3) 0.7344(3) 0.0318(8) Uani 1 1 d . . . . .
H5 H 0.086145 0.707741 0.736874 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3015(6) 0.6067(3) 0.8112(3) 0.0269(8) Uani 1 1 d . . . . .
C7 C 0.4938(6) 0.5569(3) 0.8097(3) 0.0292(8) Uani 1 1 d . . . . .
H7 H 0.548706 0.510453 0.863355 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6060(6) 0.5760(3) 0.7282(3) 0.0294(8) Uani 1 1 d . . . . .
H8 H 0.738449 0.541971 0.726128 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6653(7) 0.6722(3) 0.3690(3) 0.0360(9) Uani 1 1 d . . . . .
H9A H 0.573544 0.658555 0.301552 0.043 Uiso 1 1 calc R U . . .
H9B H 0.704372 0.745708 0.37071 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8618(7) 0.6110(3) 0.3755(3) 0.0384(9) Uani 1 1 d . . . . .
Br1 Br 0.14793(7) 0.58548(3) 0.92354(3) 0.03802(15) Uani 1 1 d . . . . .
Br2 Br 0.75263(7) 0.81137(3) 0.58021(3) 0.03551(15) Uani 1 1 d . . . . .
N1 N 1.0131(8) 0.5638(3) 0.3806(4) 0.0622(11) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.514(5) . ?
C1 C9 1.526(5) . ?
C2 C3 1.506(5) . ?
C2 Br2 1.999(3) . ?
C3 C4 1.386(5) . ?
C3 C8 1.387(5) . ?
C4 C5 1.389(6) . ?
C5 C6 1.372(5) . ?
C6 C7 1.379(5) . ?
C6 Br1 1.903(3) . ?
C7 C8 1.391(5) . ?
C9 C10 1.466(6) . ?
C10 N1 1.129(6) . ?

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 C1 C9 115.4(3) . . ?
C3 C2 C1 114.9(3) . . ?
C3 C2 Br2 107.2(2) . . ?
C1 C2 Br2 108.4(2) . . ?
C4 C3 C8 118.9(3) . . ?
C4 C3 C2 121.7(3) . . ?
C8 C3 C2 119.4(3) . . ?
C3 C4 C5 120.9(3) . . ?
C6 C5 C4 118.9(3) . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 Br1 118.4(3) . . ?
C7 C6 Br1 119.9(3) . . ?
C6 C7 C8 118.8(3) . . ?
C3 C8 C7 120.8(3) . . ?
C10 C9 C1 113.8(3) . . ?
N1 C10 C9 179.9(5) . . ?



# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_2225mg16
_database_code_depnum_ccdc_archive 'CCDC 2176282'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;

_audit_creation_date             2022-05-30T15:31:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H18 F6 N2'
_chemical_formula_weight         424.38

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6660(11)
_cell_length_b                   12.0851(11)
_cell_length_c                   8.0892(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.741(12)
_cell_angle_gamma                90
_cell_volume                     987.41(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    2242
_cell_measurement_theta_min      5.71
_cell_measurement_theta_max      71.66
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.919

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      -0.138242
_diffrn_orient_matrix_ub_12      -0.027211
_diffrn_orient_matrix_ub_13      -0.128194
_diffrn_orient_matrix_ub_21      0.055129
_diffrn_orient_matrix_ub_22      -0.107119
_diffrn_orient_matrix_ub_23      -0.053418
_diffrn_orient_matrix_ub_31      -0.033561
_diffrn_orient_matrix_ub_32      -0.063181
_diffrn_orient_matrix_ub_33      0.14585
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6111 2744 1583 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.3889 2714 1583 nmt 1.0002 -0.0002 0.8494 -0.0002 -1.0000 -0.0009 -0.0002
0.0002 -0.9998
_oxdiff_twin_integration_method  simultaneous
_twin_special_details            
;
Component 2 rotated by 179.9827° 
 around [1.00 -0.00 -0.00] (reciprocal) or [0.92 -0.00 0.39] (direct)
;

_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_number            2718
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.377
_diffrn_reflns_theta_max         62.487
_diffrn_reflns_theta_full        62.487
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             2718
_reflns_number_gt                2225
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_special_details          
'Refined as a 2-component twin.,Twin,-CF3 groups rotationally disordered'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2718
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.83405(16) 0.58159(15) 0.4447(2) 0.0298(4) Uani 1 1 d . . . . .
C2 C 0.71264(17) 0.56464(15) 0.3172(3) 0.0324(4) Uani 1 1 d . . . . .
H2 H 0.692305 0.49384 0.264305 0.039 Uiso 1 1 calc R U . . .
C3 C 0.62043(16) 0.64928(15) 0.2655(3) 0.0340(5) Uani 1 1 d . . . . .
H3 H 0.536644 0.635986 0.180498 0.041 Uiso 1 1 calc R U . . .
C4 C 0.65150(17) 0.75303(16) 0.3388(3) 0.0321(4) Uani 1 1 d . . . . .
C5 C 0.77299(18) 0.77246(16) 0.4639(3) 0.0376(5) Uani 1 1 d . . . . .
H5 H 0.794649 0.844321 0.51223 0.045 Uiso 1 1 calc R U . . .
C6 C 0.86278(17) 0.68656(16) 0.5182(3) 0.0371(5) Uani 1 1 d . . . . .
H6 H 0.945002 0.699391 0.606784 0.045 Uiso 1 1 calc R U . . .
C7 C 0.55001(19) 0.84235(17) 0.2796(3) 0.0389(5) Uani 1 1 d . . . . .
C8 C 0.93033(15) 0.48565(15) 0.5051(3) 0.0312(4) Uani 1 1 d . . . . .
H8 H 0.895026 0.421806 0.425016 0.037 Uiso 1 1 calc R U . . .
C9 C 0.93918(18) 0.44952(16) 0.6904(3) 0.0374(5) Uani 1 1 d . . . . .
H9A H 1.004966 0.38915 0.728066 0.045 Uiso 1 1 calc R U . . .
H9B H 0.971034 0.512593 0.771105 0.045 Uiso 1 1 calc R U . . .
C10 C 0.8064(2) 0.40951(18) 0.7038(3) 0.0426(5) Uani 1 1 d . . . . .
H10A H 0.740561 0.469931 0.66785 0.051 Uiso 1 1 calc R U . . .
H10B H 0.773993 0.34652 0.623157 0.051 Uiso 1 1 calc R U . . .
C11 C 0.8188(2) 0.37507(19) 0.8813(4) 0.0472(5) Uani 1 1 d . . . . .
N1 N 0.8324(2) 0.3483(2) 1.0220(3) 0.0689(7) Uani 1 1 d . . . . .
F1 F 0.43689(14) 0.81574(13) 0.3059(4) 0.0712(9) Uani 0.942(6) 1 d . . P A 1
F2 F 0.5228(3) 0.86844(19) 0.1127(3) 0.0753(7) Uani 0.942(6) 1 d . . P A 1
F3 F 0.58747(18) 0.93783(13) 0.3661(2) 0.0575(6) Uani 0.942(6) 1 d . . P A 1
F1' F 0.537(3) 0.903(3) 0.399(4) 0.067(9) Uiso 0.058(6) 1 d . . P A 2
F2' F 0.429(2) 0.8042(18) 0.191(4) 0.039(6) Uiso 0.058(6) 1 d . . P A 2
F3' F 0.575(8) 0.893(6) 0.174(10) 0.15(3) Uiso 0.058(6) 1 d . . P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.387(3) . ?
C1 C6 1.393(3) . ?
C1 C8 1.521(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.381(3) . ?
C4 C5 1.384(3) . ?
C4 C7 1.494(3) . ?
C5 C6 1.385(3) . ?
C7 F3' 1.15(8) . ?
C7 F1' 1.25(3) . ?
C7 F2 1.324(3) . ?
C7 F1 1.330(3) . ?
C7 F2' 1.34(2) . ?
C7 F3 1.342(3) . ?
C8 C9 1.535(3) . ?
C8 C8 1.554(3) 3_766 ?
C9 C10 1.533(3) . ?
C10 C11 1.459(3) . ?
C11 N1 1.147(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.47(16) . . ?
C2 C1 C8 119.91(16) . . ?
C6 C1 C8 121.59(16) . . ?
C3 C2 C1 121.15(17) . . ?
C4 C3 C2 119.41(16) . . ?
C3 C4 C5 120.46(17) . . ?
C3 C4 C7 117.98(17) . . ?
C5 C4 C7 121.56(18) . . ?
C4 C5 C6 119.64(18) . . ?
C5 C6 C1 120.83(17) . . ?
F3' C7 F1' 112(4) . . ?
F2 C7 F1 107.9(2) . . ?
F3' C7 F2' 102(4) . . ?
F1' C7 F2' 106.7(17) . . ?
F2 C7 F3 104.9(2) . . ?
F1 C7 F3 104.94(19) . . ?
F3' C7 C4 107(4) . . ?
F1' C7 C4 115.0(14) . . ?
F2 C7 C4 113.41(18) . . ?
F1 C7 C4 112.03(18) . . ?
F2' C7 C4 113.3(10) . . ?
F3 C7 C4 112.98(17) . . ?
C1 C8 C9 110.71(15) . . ?
C1 C8 C8 111.80(18) . 3_766 ?
C9 C8 C8 110.82(18) . 3_766 ?
C10 C9 C8 112.99(16) . . ?
C11 C10 C9 111.47(18) . . ?
N1 C11 C10 178.0(2) . . ?



# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_2130lesley2
_database_code_depnum_ccdc_archive 'CCDC 2176285'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_2130lesley2         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: theta limit set by dual source diffractometer
;
# Added during the CSD deposition process: Wednesday 01 June 2022 09:38 AM
# end Validation Reply Form


_audit_creation_date             2022-05-30T14:31:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C14 H12 Cl N'
_chemical_formula_weight         229.7
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_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                   11.6527(6)
_cell_length_b                   16.6170(8)
_cell_length_c                   5.9865(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1159.18(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    813
_cell_measurement_theta_min      4.62
_cell_measurement_theta_max      60.88
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      -0.071392
_diffrn_orient_matrix_ub_12      -0.073053
_diffrn_orient_matrix_ub_13      0.076406
_diffrn_orient_matrix_ub_21      -0.109941
_diffrn_orient_matrix_ub_22      0.051402
_diffrn_orient_matrix_ub_23      -0.011069
_diffrn_orient_matrix_ub_31      -0.017039
_diffrn_orient_matrix_ub_32      -0.025015
_diffrn_orient_matrix_ub_33      -0.245371
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_number            2672
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.635
_diffrn_reflns_theta_max         61.428
_diffrn_reflns_theta_full        61.428
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.785
_reflns_Friedel_fraction_full    0.525
_reflns_Friedel_fraction_max     0.525
_reflns_Friedel_coverage         0.423
_reflns_number_total             1403
_reflns_number_gt                1206
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.4844P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1403
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.7647(5) 0.4393(3) 0.2318(10) 0.0419(14) Uani 1 1 d . . . . .
H1 H 0.837523 0.447991 0.164901 0.05 Uiso 1 1 calc R U . . .
C2 C 0.7396(5) 0.4732(3) 0.4400(11) 0.0423(15) Uani 1 1 d . . . . .
H2 H 0.795953 0.504719 0.514196 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6352(4) 0.4617(3) 0.5378(10) 0.0369(13) Uani 1 1 d . . . . .
H3 H 0.619515 0.485428 0.678876 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5500(4) 0.4148(3) 0.4314(9) 0.0311(12) Uani 1 1 d . . . . .
C5 C 0.5746(4) 0.3795(3) 0.2211(9) 0.0337(12) Uani 1 1 d . . . . .
C6 C 0.6843(4) 0.3936(3) 0.1250(12) 0.0408(13) Uani 1 1 d . . . . .
H6 H 0.702057 0.370722 -0.016261 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4413(4) 0.4017(3) 0.5302(10) 0.0326(12) Uani 1 1 d . . . . .
H7 H 0.424438 0.425612 0.670465 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3607(5) 0.3556(3) 0.4287(10) 0.0357(13) Uani 1 1 d . . . . .
C9 C 0.3851(5) 0.3196(3) 0.2219(11) 0.0439(15) Uani 1 1 d . . . . .
H9 H 0.329043 0.286717 0.15154 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4892(4) 0.3315(3) 0.1212(12) 0.0411(13) Uani 1 1 d . . . . .
H10 H 0.50411 0.306896 -0.019081 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2465(4) 0.3435(3) 0.5442(10) 0.0397(14) Uani 1 1 d . . . . .
H11 H 0.243849 0.379346 0.678325 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1440(5) 0.3622(4) 0.3990(11) 0.0467(15) Uani 1 1 d . . . . .
H12A H 0.150145 0.330121 0.26014 0.056 Uiso 1 1 calc R U . . .
H12B H 0.147422 0.419697 0.356239 0.056 Uiso 1 1 calc R U . . .
C13 C 0.0270(5) 0.3458(4) 0.5039(13) 0.0559(18) Uani 1 1 d . . . . .
H13A H -0.033814 0.363609 0.399435 0.067 Uiso 1 1 calc R U . . .
H13B H 0.018044 0.287145 0.526589 0.067 Uiso 1 1 calc R U . . .
C14 C 0.0112(5) 0.3871(4) 0.7193(15) 0.0546(18) Uani 1 1 d . . . . .
Cl1 Cl 0.24010(12) 0.23944(7) 0.6387(4) 0.0583(5) Uani 1 1 d . . . . .
N1 N 0.0015(5) 0.4184(5) 0.8842(15) 0.080(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C6 1.364(8) . ?
C1 C2 1.399(9) . ?
C2 C3 1.363(8) . ?
C3 C4 1.413(8) . ?
C4 C7 1.415(7) . ?
C4 C5 1.419(8) . ?
C5 C10 1.408(8) . ?
C5 C6 1.422(7) . ?
C7 C8 1.355(8) . ?
C8 C9 1.404(9) . ?
C8 C11 1.514(7) . ?
C9 C10 1.369(8) . ?
C11 C12 1.510(8) . ?
C11 Cl1 1.821(5) . ?
C12 C13 1.526(8) . ?
C13 C14 1.472(11) . ?
C14 N1 1.122(10) . ?

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
C6 C1 C2 119.9(5) . . ?
C3 C2 C1 120.8(6) . . ?
C2 C3 C4 120.7(6) . . ?
C3 C4 C7 121.7(5) . . ?
C3 C4 C5 119.1(5) . . ?
C7 C4 C5 119.2(5) . . ?
C10 C5 C4 117.9(5) . . ?
C10 C5 C6 123.9(5) . . ?
C4 C5 C6 118.2(5) . . ?
C1 C6 C5 121.3(6) . . ?
C8 C7 C4 121.3(5) . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 C11 118.6(5) . . ?
C9 C8 C11 121.6(5) . . ?
C10 C9 C8 120.4(5) . . ?
C9 C10 C5 121.4(6) . . ?
C12 C11 C8 113.9(5) . . ?
C12 C11 Cl1 110.0(4) . . ?
C8 C11 Cl1 107.7(3) . . ?
C11 C12 C13 115.7(6) . . ?
C14 C13 C12 112.9(6) . . ?
N1 C14 C13 178.6(7) . . ?



# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether'
####################################################################### 
# 
# 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_2227mn17
_database_code_depnum_ccdc_archive 'CCDC 2176283'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;

_audit_creation_date             2022-05-30T21:39:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H18 Cl2 N2'
_chemical_formula_weight         357.26

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5854(2)
_cell_length_b                   11.8999(2)
_cell_length_c                   7.67500(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.688(2)
_cell_angle_gamma                90
_cell_volume                     904.44(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    8910
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      71.57
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.444
_shelx_estimated_absorpt_T_max   0.738

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      0.105161
_diffrn_orient_matrix_ub_12      0.070917
_diffrn_orient_matrix_ub_13      0.150151
_diffrn_orient_matrix_ub_21      -0.114529
_diffrn_orient_matrix_ub_22      0.068225
_diffrn_orient_matrix_ub_23      0.029373
_diffrn_orient_matrix_ub_31      -0.004252
_diffrn_orient_matrix_ub_32      -0.084146
_diffrn_orient_matrix_ub_33      0.150422
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_number            12699
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.465
_diffrn_reflns_theta_max         62.486
_diffrn_reflns_theta_full        62.486
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             1443
_reflns_number_gt                1391
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1443
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.16979(13) 0.58292(12) 0.08811(18) 0.0292(3) Uani 1 1 d . . . . .
C2 C 0.29554(14) 0.56324(13) 0.0742(2) 0.0332(3) Uani 1 1 d . . . . .
H2 H 0.317702 0.48957 0.046793 0.04 Uiso 1 1 calc R U . . .
C3 C 0.38889(14) 0.64875(13) 0.0993(2) 0.0380(4) Uani 1 1 d . . . . .
H3 H 0.475222 0.633778 0.092665 0.046 Uiso 1 1 calc R U . . .
C4 C 0.35483(14) 0.75553(13) 0.1340(2) 0.0362(3) Uani 1 1 d . . . . .
C5 C 0.23059(15) 0.77873(13) 0.1477(2) 0.0371(3) Uani 1 1 d . . . . .
H5 H 0.208098 0.853076 0.171185 0.045 Uiso 1 1 calc R U . . .
C6 C 0.13983(14) 0.69186(12) 0.1264(2) 0.0346(3) Uani 1 1 d . . . . .
H6 H 0.055081 0.70686 0.138237 0.042 Uiso 1 1 calc R U . . .
C7 C 0.07193(13) 0.48643(12) 0.06927(19) 0.0302(3) Uani 1 1 d . . . . .
H7 H 0.106386 0.420094 0.019562 0.036 Uiso 1 1 calc R U . . .
C8 C 0.06762(14) 0.45395(12) 0.2609(2) 0.0338(3) Uani 1 1 d . . . . .
H8A H 0.037109 0.51948 0.315021 0.041 Uiso 1 1 calc R U . . .
H8B H 0.00107 0.392798 0.245056 0.041 Uiso 1 1 calc R U . . .
C9 C 0.20519(15) 0.41523(13) 0.3954(2) 0.0374(4) Uani 1 1 d . . . . .
H9A H 0.23844 0.352764 0.337998 0.045 Uiso 1 1 calc R U . . .
H9B H 0.270414 0.477979 0.417748 0.045 Uiso 1 1 calc R U . . .
C10 C 0.19846(17) 0.37773(13) 0.5736(2) 0.0411(4) Uani 1 1 d . . . . .
Cl1 Cl 0.46932(4) 0.86538(4) 0.16072(7) 0.05601(18) Uani 1 1 d . . . . .
N1 N 0.19046(19) 0.34865(14) 0.7108(2) 0.0615(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C6 1.390(2) . ?
C1 C2 1.3925(19) . ?
C1 C7 1.5188(19) . ?
C2 C3 1.384(2) . ?
C3 C4 1.372(2) . ?
C4 C5 1.383(2) . ?
C4 Cl1 1.7447(14) . ?
C5 C6 1.381(2) . ?
C7 C8 1.537(2) . ?
C7 C7 1.552(3) 3_565 ?
C8 C9 1.529(2) . ?
C9 C10 1.464(2) . ?
C10 N1 1.140(2) . ?

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
C6 C1 C2 117.95(13) . . ?
C6 C1 C7 121.75(12) . . ?
C2 C1 C7 120.26(13) . . ?
C3 C2 C1 121.37(14) . . ?
C4 C3 C2 118.97(13) . . ?
C3 C4 C5 121.42(13) . . ?
C3 C4 Cl1 119.82(11) . . ?
C5 C4 Cl1 118.76(12) . . ?
C6 C5 C4 118.81(14) . . ?
C5 C6 C1 121.45(13) . . ?
C1 C7 C8 110.42(11) . . ?
C1 C7 C7 112.27(14) . 3_565 ?
C8 C7 C7 110.75(14) . 3_565 ?
C9 C8 C7 112.27(11) . . ?
C10 C9 C8 111.95(13) . . ?
N1 C10 C9 178.63(18) . . ?



# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
