# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_p20220902a
_audit_block_doi                 10.5517/ccdc.csd.cc2dndcv
_database_code_depnum_ccdc_archive 'CCDC 2224137'
loop_
_audit_author_name
_audit_author_address
'Peiyuan Yao'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2022-09-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-N-(3-(2-chlorophenyl)-2-methylpropyl)prop-2-en-1-amine hydrochloride'
_chemical_formula_moiety         'C13 H19 Cl N, Cl'
_chemical_formula_sum            'C13 H19 Cl2 N'
_chemical_formula_weight         260.19
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.95940(10)
_cell_length_b                   10.73110(10)
_cell_length_c                   27.2017(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1447.67(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13015
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      78.6220
_cell_measurement_theta_min      4.4180
_shelx_estimated_absorpt_T_max   0.580
_shelx_estimated_absorpt_T_min   0.473
_exptl_absorpt_coefficient_mu    3.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'white solid'
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18528
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.255
_diffrn_reflns_theta_min         4.429
_diffrn_ambient_temperature      294.15
_diffrn_detector                 pilatus
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  94.00   0.50    0.50    --    5.00  19.00 -14.00  294
  2  ω   -138.00   9.00   0.50    0.50    --  -49.00 -19.00 177.00  294
  3  ω   -199.00 -52.00   0.50    2.00    -- -110.00 -19.00 177.00  294
  4  ω   -168.00 -21.00   0.50    2.00    -- -110.00  19.00 -14.00  294
  5  ω    -79.00  40.00   0.50    0.50    --  -49.00  57.00-180.00  238
  6  ω    -82.00  40.00   0.50    0.50    --  -49.00  38.00 120.00  244
  7  ω   -144.00 -21.00   0.50    2.00    -- -110.00  72.00-180.00  246
  8  ω   -144.00 -21.00   0.50    2.00    -- -110.00  72.00 120.00  246
  9  ω   -199.00 -79.00   0.50    2.00    -- -110.00 -45.00-174.39  240
 10  ω   -144.00 -21.00   0.50    2.00    -- -110.00  72.00 -30.00  246
 11  ω   -144.00 -21.00   0.50    2.00    -- -110.00  72.00 150.00  246
 12  ω   -140.00 -21.00   0.50    2.00    -- -110.00  57.00-150.00  238
 13  ω   -143.00 -21.00   0.50    2.00    -- -110.00  38.00 -30.00  244
 14  ω    -84.00  35.00   0.50    0.50    --    5.00 -57.00 -60.00  238
 15  ω   -138.00 -17.00   0.50    0.50    --  -49.00 -64.00   5.84  242
 16  ω   -138.00 -17.00   0.50    0.50    --  -49.00 -66.00  85.70  242
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054471000
_diffrn_orient_matrix_UB_12      -0.0134760000
_diffrn_orient_matrix_UB_13      0.0563731000
_diffrn_orient_matrix_UB_21      -0.0772131000
_diffrn_orient_matrix_UB_22      0.1384957000
_diffrn_orient_matrix_UB_23      0.0049067000
_diffrn_orient_matrix_UB_31      -0.3008365000
_diffrn_orient_matrix_UB_32      -0.0353445000
_diffrn_orient_matrix_UB_33      -0.0022687000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   Rotating-anode
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2963
_reflns_number_total             3066
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1170 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.1592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.25087(15) 0.64631(8) 0.47669(2) 0.0781(2) Uani 1 1 d . . . . .
N1 N 0.5071(4) 0.64379(15) 0.25866(5) 0.0455(3) Uani 1 1 d . . . . .
H1A H 0.367986 0.592919 0.263638 0.055 Uiso 1 1 calc R U . . .
H1B H 0.656517 0.597875 0.258337 0.055 Uiso 1 1 calc R U . . .
C1 C 0.4917(5) 0.5350(2) 0.46123(8) 0.0577(5) Uani 1 1 d . . . . .
C2 C 0.6084(6) 0.4687(3) 0.49947(9) 0.0726(7) Uani 1 1 d . . . . .
H2 H 0.556562 0.484009 0.531769 0.087 Uiso 1 1 calc R U . . .
C3 C 0.7999(7) 0.3806(3) 0.48944(10) 0.0791(8) Uani 1 1 d . . . . .
H3 H 0.878838 0.335896 0.514943 0.095 Uiso 1 1 calc R U . . .
C4 C 0.8756(7) 0.3584(3) 0.44179(11) 0.0791(8) Uani 1 1 d . . . . .
H4 H 1.006031 0.298469 0.435089 0.095 Uiso 1 1 calc R U . . .
C5 C 0.7602(7) 0.4238(2) 0.40389(9) 0.0657(6) Uani 1 1 d . . . . .
H5 H 0.814701 0.407856 0.371788 0.079 Uiso 1 1 calc R U . . .
C6 C 0.5610(4) 0.5145(2) 0.41268(7) 0.0520(5) Uani 1 1 d . . . . .
C7 C 0.4393(5) 0.5832(2) 0.36950(8) 0.0536(5) Uani 1 1 d . . . . .
H7A H 0.276854 0.625588 0.380212 0.064 Uiso 1 1 calc R U . . .
H7B H 0.388488 0.523330 0.344428 0.064 Uiso 1 1 calc R U . . .
C8 C 0.6331(4) 0.67853(19) 0.34719(8) 0.0482(4) Uani 1 1 d . . . . .
H8 H 0.801571 0.635363 0.339180 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6992(7) 0.7835(2) 0.38317(10) 0.0725(8) Uani 1 1 d . . . . .
H9A H 0.537774 0.828993 0.390739 0.109 Uiso 1 1 calc R U . . .
H9B H 0.828796 0.838673 0.368568 0.109 Uiso 1 1 calc R U . . .
H9C H 0.772543 0.748764 0.412819 0.109 Uiso 1 1 calc R U . . .
C10 C 0.5225(5) 0.73528(18) 0.29989(7) 0.0513(4) Uani 1 1 d . . . . .
H10A H 0.343688 0.768258 0.306173 0.062 Uiso 1 1 calc R U . . .
H10B H 0.637030 0.804229 0.290098 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4751(7) 0.7065(2) 0.21001(8) 0.0617(6) Uani 1 1 d . . . . .
H11A H 0.308515 0.753852 0.209868 0.074 Uiso 1 1 calc R U . . .
H11B H 0.622950 0.764405 0.205125 0.074 Uiso 1 1 calc R U . . .
C12 C 0.4709(9) 0.6163(3) 0.16940(9) 0.0834(9) Uani 1 1 d . . . . .
H12 H 0.346094 0.551976 0.171986 0.100 Uiso 1 1 calc R U . . .
C13 C 0.6141(16) 0.6160(5) 0.13213(14) 0.164(3) Uani 1 1 d . . . . .
H13A H 0.742434 0.678144 0.127578 0.197 Uiso 1 1 calc R U . . .
H13B H 0.593295 0.553693 0.108686 0.197 Uiso 1 1 calc R U . . .
Cl2 Cl 1.00802(10) 0.46501(5) 0.26117(2) 0.05634(16) 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
Cl1 C1 1.741(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C10 1.492(2) . ?
N1 C11 1.493(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.382(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.407(4) . ?
C6 C7 1.512(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.530(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.528(3) . ?
C8 C10 1.525(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.469(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.238(6) . ?
C13 H13A 0.9300 . ?
C13 H13B 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
H1A N1 H1B 107.9 . . ?
C10 N1 H1A 109.2 . . ?
C10 N1 H1B 109.2 . . ?
C10 N1 C11 112.01(16) . . ?
C11 N1 H1A 109.2 . . ?
C11 N1 H1B 109.2 . . ?
C2 C1 Cl1 117.21(19) . . ?
C6 C1 Cl1 120.73(18) . . ?
C6 C1 C2 122.1(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 116.6(2) . . ?
C1 C6 C7 124.4(2) . . ?
C5 C6 C7 119.0(2) . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 C8 112.55(18) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8 107.9 . . ?
C9 C8 C7 112.0(2) . . ?
C9 C8 H8 107.9 . . ?
C10 C8 C7 112.09(18) . . ?
C10 C8 H8 107.9 . . ?
C10 C8 C9 108.86(18) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C8 112.92(16) . . ?
N1 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C8 C10 H10A 109.0 . . ?
C8 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N1 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 N1 111.78(19) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C11 C12 H12 116.2 . . ?
C13 C12 C11 127.5(4) . . ?
C13 C12 H12 116.2 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?

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
Cl1 C1 C2 C3 -179.6(2) . . . . ?
Cl1 C1 C6 C5 179.20(19) . . . . ?
Cl1 C1 C6 C7 -0.3(3) . . . . ?
N1 C11 C12 C13 -126.5(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 C8 106.1(3) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C2 C1 C6 C7 179.5(2) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C5 C6 C7 C8 -73.3(3) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C6 C7 C8 C9 -64.6(3) . . . . ?
C6 C7 C8 C10 172.73(18) . . . . ?
C7 C8 C10 N1 -67.9(3) . . . . ?
C9 C8 C10 N1 167.7(2) . . . . ?
C10 N1 C11 C12 177.7(3) . . . . ?
C11 N1 C10 C8 -163.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.576
_oxdiff_exptl_absorpt_empirical_full_min 0.701
####################################################################### 
# 
# 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_r20230205b_autored
_database_code_depnum_ccdc_archive 'CCDC 2241445'
loop_
_audit_author_name
_audit_author_address
'Zefei Xu'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2023-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-N-(3-(2-bromo-3-fluorophenyl)-2-methylpropyl)prop-2-en-1-amine hydrochloride'
_chemical_formula_moiety         'C13 H18 Br F N, Cl'
_chemical_formula_sum            'C13 H18 Br Cl F N'
_chemical_formula_weight         322.64
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.8988(2)
_cell_length_b                   10.7881(3)
_cell_length_c                   13.7759(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.020(3)
_cell_angle_gamma                90
_cell_volume                     720.92(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4817
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.0720
_cell_measurement_theta_min      2.3850
_shelx_estimated_absorpt_T_max   0.643
_shelx_estimated_absorpt_T_min   0.507
_exptl_absorpt_coefficient_mu    3.027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5945
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.407
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00  30.00   0.50    3.00    --  -30.00  15.00 180.00  246
  2  ω    -66.00  45.00   0.50    3.00    --  -30.00  70.00  90.00  222
  3  ω   -120.00 -10.00   0.50    3.00    --  -30.00 -70.00   0.00  220
  4  ω    -66.00  39.00   0.50    3.00    --  -30.00  70.00 180.00  210
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'rigaku saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0289750000
_diffrn_orient_matrix_UB_12      -0.0279841000
_diffrn_orient_matrix_UB_13      0.0469314000
_diffrn_orient_matrix_UB_21      -0.0067245000
_diffrn_orient_matrix_UB_22      -0.0594261000
_diffrn_orient_matrix_UB_23      -0.0222087000
_diffrn_orient_matrix_UB_31      0.1431360000
_diffrn_orient_matrix_UB_32      0.0029027000
_diffrn_orient_matrix_UB_33      -0.0030817000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                2677
_reflns_number_total             2820
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.970
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.153
_refine_ls_abs_structure_details 
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.091(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²+2.3076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1517
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.41955(17) 0.58772(9) 0.95867(6) 0.0241(3) Uani 1 1 d . . . . .
Cl1 Cl 1.0085(5) 0.3905(2) 0.52104(17) 0.0208(5) Uani 1 1 d . . . . .
F1 F 0.7949(14) 0.4235(6) 1.0861(4) 0.0352(16) Uani 1 1 d . . . . .
N1 N 0.5019(16) 0.5713(8) 0.5118(5) 0.0179(16) Uani 1 1 d . . . . .
H1A H 0.363577 0.518777 0.522336 0.022 Uiso 1 1 calc R . . . .
H1B H 0.657162 0.525459 0.510243 0.022 Uiso 1 1 calc R . . . .
C1 C 0.6588(19) 0.4675(9) 0.9190(7) 0.0196(19) Uani 1 1 d . . . . .
C2 C 0.821(2) 0.4004(10) 0.9912(7) 0.024(2) Uani 1 1 d . . . . .
C3 C 1.004(3) 0.3103(10) 0.9708(8) 0.030(2) Uani 1 1 d . . . . .
H3 H 1.109861 0.265123 1.021996 0.036 Uiso 1 1 calc R . . . .
C4 C 1.028(2) 0.2875(10) 0.8741(8) 0.028(2) Uani 1 1 d . . . . .
H4 H 1.154445 0.226411 0.858106 0.034 Uiso 1 1 calc R . . . .
C5 C 0.871(2) 0.3527(9) 0.8000(7) 0.024(2) Uani 1 1 d . . . . .
H5 H 0.890981 0.334952 0.733741 0.029 Uiso 1 1 calc R . . . .
C6 C 0.6831(19) 0.4445(9) 0.8198(7) 0.0200(19) Uani 1 1 d . . . . .
C7 C 0.523(2) 0.5135(10) 0.7354(7) 0.023(2) Uani 1 1 d . . . . .
H7A H 0.370072 0.559415 0.759242 0.028 Uiso 1 1 calc R . . . .
H7B H 0.440739 0.453206 0.685536 0.028 Uiso 1 1 calc R . . . .
C8 C 0.7038(18) 0.6052(9) 0.6876(6) 0.017(2) Uani 1 1 d . . . . .
H8 H 0.866579 0.558886 0.669868 0.021 Uiso 1 1 calc R . . . .
C9 C 0.550(2) 0.6624(8) 0.5938(7) 0.019(2) Uani 1 1 d . . . . .
H9A H 0.370240 0.694962 0.607557 0.022 Uiso 1 1 calc R . . . .
H9B H 0.658162 0.733022 0.573576 0.022 Uiso 1 1 calc R . . . .
C10 C 0.427(2) 0.6354(9) 0.4151(7) 0.022(2) Uani 1 1 d . . . . .
H10A H 0.265782 0.690078 0.418470 0.027 Uiso 1 1 calc R . . . .
H10B H 0.582583 0.687912 0.401453 0.027 Uiso 1 1 calc R . . . .
C11 C 0.359(3) 0.5447(10) 0.3340(8) 0.032(3) Uani 1 1 d . . . . .
H11 H 0.218654 0.485281 0.339715 0.038 Uiso 1 1 calc R . . . .
C12 C 0.480(4) 0.5418(14) 0.2560(10) 0.057(4) Uani 1 1 d . . . . .
H12A H 0.620481 0.599986 0.248204 0.068 Uiso 1 1 calc R . . . .
H12B H 0.427201 0.481482 0.206638 0.068 Uiso 1 1 calc R . . . .
C13 C 0.810(2) 0.7096(9) 0.7579(7) 0.024(2) Uani 1 1 d . . . . .
H13A H 0.653658 0.757679 0.774868 0.036 Uiso 1 1 calc GR . . . .
H13B H 0.931575 0.763890 0.726250 0.036 Uiso 1 1 calc GR . . . .
H13C H 0.912723 0.674102 0.817549 0.036 Uiso 1 1 calc GR . . . .


_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 C1 1.880(10) . ?
F1 C2 1.355(11) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C9 1.492(12) . ?
N1 C10 1.501(12) . ?
C1 C2 1.388(13) . ?
C1 C6 1.410(14) . ?
C2 C3 1.376(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.406(15) . ?
C6 C7 1.506(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.537(13) . ?
C8 H8 1.0000 . ?
C8 C9 1.532(12) . ?
C8 C13 1.528(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.488(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.298(17) . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
H1A N1 H1B 108.0 . . ?
C9 N1 H1A 109.4 . . ?
C9 N1 H1B 109.4 . . ?
C9 N1 C10 111.2(8) . . ?
C10 N1 H1A 109.4 . . ?
C10 N1 H1B 109.4 . . ?
C2 C1 Br1 118.0(7) . . ?
C2 C1 C6 119.1(9) . . ?
C6 C1 Br1 122.9(7) . . ?
F1 C2 C1 118.3(9) . . ?
F1 C2 C3 118.7(9) . . ?
C3 C2 C1 123.1(9) . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.1(10) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(10) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(10) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 123.8(9) . . ?
C5 C6 C1 117.3(9) . . ?
C5 C6 C7 118.9(9) . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C6 C7 C8 112.3(8) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8 108.1 . . ?
C9 C8 C7 112.0(7) . . ?
C9 C8 H8 108.1 . . ?
C13 C8 C7 111.6(8) . . ?
C13 C8 H8 108.1 . . ?
C13 C8 C9 108.7(8) . . ?
N1 C9 C8 112.3(8) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N1 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 N1 111.4(8) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11 118.1 . . ?
C12 C11 C10 123.9(12) . . ?
C12 C11 H11 118.1 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 F1 1.2(13) . . . . ?
Br1 C1 C2 C3 -179.9(9) . . . . ?
Br1 C1 C6 C5 179.5(7) . . . . ?
Br1 C1 C6 C7 0.3(13) . . . . ?
F1 C2 C3 C4 179.9(10) . . . . ?
N1 C10 C11 C12 -124.4(14) . . . . ?
C1 C2 C3 C4 1.0(17) . . . . ?
C1 C6 C7 C8 106.9(11) . . . . ?
C2 C1 C6 C5 0.6(14) . . . . ?
C2 C1 C6 C7 -178.5(9) . . . . ?
C2 C3 C4 C5 -0.7(17) . . . . ?
C3 C4 C5 C6 0.4(17) . . . . ?
C4 C5 C6 C1 -0.4(15) . . . . ?
C4 C5 C6 C7 178.8(10) . . . . ?
C5 C6 C7 C8 -72.3(12) . . . . ?
C6 C1 C2 F1 -179.9(9) . . . . ?
C6 C1 C2 C3 -1.0(16) . . . . ?
C6 C7 C8 C9 172.4(8) . . . . ?
C6 C7 C8 C13 -65.3(11) . . . . ?
C7 C8 C9 N1 -70.8(10) . . . . ?
C9 N1 C10 C11 -175.9(9) . . . . ?
C10 N1 C9 C8 -163.8(8) . . . . ?
C13 C8 C9 N1 165.3(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.510
_oxdiff_exptl_absorpt_empirical_full_min 0.588
####################################################################### 
# 
# 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_r20230205a_autored
_database_code_depnum_ccdc_archive 'CCDC 2241444'
loop_
_audit_author_name
_audit_author_address
'Zefei Xu'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2023-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-N-(3-(2-bromo-3-methylphenyl)-2-methylpropyl)prop-2-en-1-amine hydrochloride'
_chemical_formula_moiety         'C14 H21 Br N, Cl'
_chemical_formula_sum            'C14 H21 Br Cl N'
_chemical_formula_weight         318.68
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9604(2)
_cell_length_b                   10.8195(4)
_cell_length_c                   29.3754(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1576.55(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6722
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.5790
_cell_measurement_theta_min      2.7520
_shelx_estimated_absorpt_T_max   0.651
_shelx_estimated_absorpt_T_min   0.512
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7454
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.006
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  60.00   0.50   10.00    --  -30.00  70.00   0.00  252
  2  ω    -66.00  60.00   0.50   10.00    --  -30.00  70.00  90.00  252
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'rigaku saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0032445000
_diffrn_orient_matrix_UB_12      0.0118258000
_diffrn_orient_matrix_UB_13      -0.0237444000
_diffrn_orient_matrix_UB_21      -0.0172649000
_diffrn_orient_matrix_UB_22      -0.0639682000
_diffrn_orient_matrix_UB_23      -0.0043864000
_diffrn_orient_matrix_UB_31      -0.1419385000
_diffrn_orient_matrix_UB_32      0.0080160000
_diffrn_orient_matrix_UB_33      0.0000006000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3057
_reflns_number_total             3206
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.3839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0855
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C12(H12)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.e Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.78520(9) 0.65675(4) 0.53059(2) 0.02864(15) Uani 1 1 d . . . . .
N1 N 0.4978(7) 0.6669(3) 0.73806(11) 0.0185(7) Uani 1 1 d . . . . .
H1A H 0.639767 0.615221 0.733231 0.022 Uiso 1 1 calc R . . . .
H1B H 0.345028 0.620340 0.738418 0.022 Uiso 1 1 calc R . . . .
C1 C 0.4848(12) 0.4723(5) 0.46573(16) 0.0376(12) Uani 1 1 d . . . . .
H1C H 0.676948 0.454080 0.461779 0.056 Uiso 1 1 calc GR . . . .
H1D H 0.447913 0.556867 0.455544 0.056 Uiso 1 1 calc GR . . . .
H1E H 0.377816 0.414086 0.447656 0.056 Uiso 1 1 calc GR . . . .
C2 C 0.4095(10) 0.4595(4) 0.51616(15) 0.0250(9) Uani 1 1 d . . . . .
C3 C 0.2185(12) 0.3713(4) 0.52956(16) 0.0381(12) Uani 1 1 d . . . . .
H3 H 0.142700 0.317096 0.507586 0.046 Uiso 1 1 calc R . . . .
C4 C 0.1387(11) 0.3627(5) 0.57512(18) 0.0397(13) Uani 1 1 d . . . . .
H4 H 0.002518 0.305014 0.583180 0.048 Uiso 1 1 calc R . . . .
C5 C 0.2500(11) 0.4343(4) 0.60830(15) 0.0300(11) Uani 1 1 d . . . . .
H5 H 0.193790 0.425070 0.639027 0.036 Uiso 1 1 calc R . . . .
C6 C 0.4548(9) 0.5250(4) 0.59658(15) 0.0235(9) Uani 1 1 d . . . . .
C7 C 0.5234(9) 0.5355(4) 0.55004(14) 0.0215(9) Uani 1 1 d . . . . .
C8 C 0.5776(9) 0.6035(4) 0.63479(15) 0.0252(10) Uani 1 1 d . . . . .
H8A H 0.737515 0.647546 0.622804 0.030 Uiso 1 1 calc R . . . .
H8B H 0.639194 0.548161 0.659523 0.030 Uiso 1 1 calc R . . . .
C9 C 0.3778(9) 0.6997(4) 0.65483(15) 0.0218(9) Uani 1 1 d . . . . .
H9 H 0.204766 0.656067 0.661747 0.026 Uiso 1 1 calc R . . . .
C10 C 0.4815(10) 0.7587(4) 0.69933(14) 0.0222(9) Uani 1 1 d . . . . .
H10A H 0.662651 0.794141 0.693910 0.027 Uiso 1 1 calc R . . . .
H10B H 0.359646 0.827061 0.708134 0.027 Uiso 1 1 calc R . . . .
C11 C 0.5314(10) 0.7294(4) 0.78400(14) 0.0250(10) Uani 1 1 d . . . . .
H11A H 0.697885 0.779855 0.783831 0.030 Uiso 1 1 calc R . . . .
H11B H 0.376884 0.785412 0.789484 0.030 Uiso 1 1 calc R . . . .
C12 C 0.5469(11) 0.6358(4) 0.82171(15) 0.0325(11) Uani 1 1 d . . . . .
H12 H 0.682277 0.573907 0.819820 0.039 Uiso 1 1 calc R . . . .
C13 C 0.3864(18) 0.6342(6) 0.8568(2) 0.083(3) Uani 1 1 d . . . . .
H13A H 0.248983 0.694882 0.859743 0.099 Uiso 1 1 calc R . . . .
H13B H 0.406879 0.572434 0.879560 0.099 Uiso 1 1 calc R . . . .
C14 C 0.3166(11) 0.8040(4) 0.61987(16) 0.0319(11) Uani 1 1 d . . . . .
H14A H 0.481297 0.851425 0.614018 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.177621 0.858940 0.632203 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.252430 0.767261 0.591360 0.048 Uiso 1 1 calc GR . . . .
Cl1 Cl -0.0058(2) 0.48524(9) 0.73765(4) 0.0226(2) 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
Br1 C7 1.932(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C10 1.512(5) . ?
N1 C11 1.519(5) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 C2 1.534(6) . ?
C2 C3 1.401(7) . ?
C2 C7 1.409(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.454(7) . ?
C6 C7 1.413(6) . ?
C6 C8 1.534(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.553(6) . ?
C9 H9 1.0000 . ?
C9 C10 1.543(6) . ?
C9 C14 1.556(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.503(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.304(8) . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 107.8 . . ?
C10 N1 H1A 109.1 . . ?
C10 N1 H1B 109.1 . . ?
C10 N1 C11 112.4(3) . . ?
C11 N1 H1A 109.1 . . ?
C11 N1 H1B 109.1 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 C7 118.0(4) . . ?
C7 C2 C1 122.1(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.2(5) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C8 118.6(4) . . ?
C7 C6 C5 116.8(4) . . ?
C7 C6 C8 124.6(4) . . ?
C2 C7 Br1 117.2(3) . . ?
C2 C7 C6 122.7(4) . . ?
C6 C7 Br1 120.2(3) . . ?
C6 C8 H8A 108.9 . . ?
C6 C8 H8B 108.9 . . ?
C6 C8 C9 113.3(4) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9 108.0 . . ?
C8 C9 C14 111.1(4) . . ?
C10 C9 C8 112.7(4) . . ?
C10 C9 H9 108.0 . . ?
C10 C9 C14 108.9(3) . . ?
C14 C9 H9 108.0 . . ?
N1 C10 C9 112.6(3) . . ?
N1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 N1 111.1(3) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12 117.9 . . ?
C13 C12 C11 124.1(5) . . ?
C13 C12 H12 117.9 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C11 C12 C13 -123.7(7) . . . . ?
C1 C2 C3 C4 -177.0(5) . . . . ?
C1 C2 C7 Br1 -0.8(6) . . . . ?
C1 C2 C7 C6 179.8(4) . . . . ?
C2 C3 C4 C5 -3.1(8) . . . . ?
C3 C2 C7 Br1 -179.8(3) . . . . ?
C3 C2 C7 C6 0.8(7) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C7 1.5(7) . . . . ?
C4 C5 C6 C8 -179.6(4) . . . . ?
C5 C6 C7 Br1 178.1(3) . . . . ?
C5 C6 C7 C2 -2.5(6) . . . . ?
C5 C6 C8 C9 -70.2(5) . . . . ?
C6 C8 C9 C10 168.0(4) . . . . ?
C6 C8 C9 C14 -69.5(5) . . . . ?
C7 C2 C3 C4 2.0(7) . . . . ?
C7 C6 C8 C9 108.7(5) . . . . ?
C8 C6 C7 Br1 -0.8(6) . . . . ?
C8 C6 C7 C2 178.6(4) . . . . ?
C8 C9 C10 N1 -66.7(5) . . . . ?
C10 N1 C11 C12 -180.0(4) . . . . ?
C11 N1 C10 C9 -165.7(4) . . . . ?
C14 C9 C10 N1 169.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.662
####################################################################### 
# 
# 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_r20230204a_autored
_database_code_depnum_ccdc_archive 'CCDC 2241441'
loop_
_audit_author_name
_audit_author_address
'Zefei Xu'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2023-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-N-(3-(2-bromo-4-methylphenyl)-2-methylpropyl)prop-2-en-1-amine hydrochloride'
_chemical_formula_moiety         'C14 H21 Br N, Cl'
_chemical_formula_sum            'C14 H21 Br Cl N'
_chemical_formula_weight         318.68
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5543(2)
_cell_length_b                   6.5919(2)
_cell_length_c                   12.4634(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.424(2)
_cell_angle_gamma                90
_cell_volume                     776.49(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7370
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.1670
_cell_measurement_theta_min      1.6970
_shelx_estimated_absorpt_T_max   0.679
_shelx_estimated_absorpt_T_min   0.553
_exptl_absorpt_coefficient_mu    2.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11301
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.654
_diffrn_reflns_theta_min         2.155
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    1.50    --  -20.00   0.00 180.00  360
  2  ω   -110.00   7.00   0.50    1.50    --  -20.00 -70.00 180.00  234
  3  ω   -110.00 -19.00   0.50    1.50    --  -20.00 -70.00  90.00  182
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'rigaku saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0723872000
_diffrn_orient_matrix_UB_12      -0.0081356000
_diffrn_orient_matrix_UB_13      0.0062613000
_diffrn_orient_matrix_UB_21      0.0188267000
_diffrn_orient_matrix_UB_22      0.0039191000
_diffrn_orient_matrix_UB_23      0.0571553000
_diffrn_orient_matrix_UB_31      -0.0061923000
_diffrn_orient_matrix_UB_32      0.1072422000
_diffrn_orient_matrix_UB_33      -0.0015924000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.712
_reflns_number_gt                4742
_reflns_number_total             5531
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 1616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         5531
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0866
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C12(H12)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.e Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.17108(3) 0.25326(5) 0.05753(2) 0.04420(11) Uani 1 1 d . . . . .
N1 N 0.1664(2) 0.5980(3) 0.46466(15) 0.0207(4) Uani 1 1 d . . . . .
H1A H 0.155735 0.461157 0.458297 0.025 Uiso 1 1 calc R . . . .
H1B H 0.078519 0.653071 0.461465 0.025 Uiso 1 1 calc R . . . .
C1 C 0.7351(4) 0.2507(9) 0.1298(2) 0.0520(9) Uani 1 1 d . . . . .
H1C H 0.715786 0.105125 0.121525 0.078 Uiso 1 1 calc GR . . . .
H1D H 0.803885 0.273941 0.195073 0.078 Uiso 1 1 calc GR . . . .
H1E H 0.773725 0.300949 0.066147 0.078 Uiso 1 1 calc GR . . . .
C2 C 0.6005(3) 0.3611(6) 0.1399(2) 0.0350(6) Uani 1 1 d . . . . .
C3 C 0.4704(3) 0.2769(5) 0.10154(18) 0.0334(6) Uani 1 1 d . . . . .
H3 H 0.465669 0.147206 0.067952 0.040 Uiso 1 1 calc R . . . .
C4 C 0.3459(3) 0.3811(5) 0.11179(19) 0.0288(5) Uani 1 1 d . . . . .
C5 C 0.3459(3) 0.5734(4) 0.15777(18) 0.0241(5) Uani 1 1 d . . . . .
C6 C 0.4786(3) 0.6568(5) 0.1941(2) 0.0288(5) Uani 1 1 d . . . . .
H6 H 0.484106 0.788468 0.225408 0.035 Uiso 1 1 calc R . . . .
C7 C 0.6026(3) 0.5527(5) 0.1858(2) 0.0343(6) Uani 1 1 d . . . . .
H7 H 0.690926 0.614007 0.212208 0.041 Uiso 1 1 calc R . . . .
C8 C 0.2134(3) 0.6900(4) 0.16866(19) 0.0277(5) Uani 1 1 d . . . . .
H8A H 0.146613 0.674875 0.100482 0.033 Uiso 1 1 calc R . . . .
H8B H 0.237849 0.835665 0.176972 0.033 Uiso 1 1 calc R . . . .
C9 C 0.1370(3) 0.6260(5) 0.26400(19) 0.0269(5) Uani 1 1 d . . . . .
H9 H 0.118149 0.476810 0.259619 0.032 Uiso 1 1 calc R . . . .
C10 C 0.2309(2) 0.6737(4) 0.37064(17) 0.0194(4) Uani 1 1 d . . . . .
H10A H 0.324655 0.609631 0.370996 0.023 Uiso 1 1 calc R . . . .
H10B H 0.244959 0.822194 0.377294 0.023 Uiso 1 1 calc R . . . .
C11 C 0.2487(2) 0.6441(4) 0.57355(18) 0.0235(4) Uani 1 1 d . . . . .
H11A H 0.198695 0.586273 0.630667 0.028 Uiso 1 1 calc R . . . .
H11B H 0.253748 0.792989 0.583928 0.028 Uiso 1 1 calc R . . . .
C12 C 0.3956(3) 0.5596(4) 0.58558(19) 0.0253(5) Uani 1 1 d . . . . .
H12 H 0.407534 0.419597 0.571299 0.030 Uiso 1 1 calc R . . . .
C13 C 0.5085(3) 0.6709(5) 0.6150(2) 0.0319(6) Uani 1 1 d . . . . .
H13A H 0.498964 0.811253 0.629675 0.038 Uiso 1 1 calc R . . . .
H13B H 0.599879 0.611163 0.621664 0.038 Uiso 1 1 calc R . . . .
C14 C -0.0044(3) 0.7405(9) 0.2551(2) 0.0466(8) Uani 1 1 d . . . . .
H14A H 0.013222 0.886899 0.254287 0.070 Uiso 1 1 calc GR . . . .
H14B H -0.051687 0.706568 0.317480 0.070 Uiso 1 1 calc GR . . . .
H14C H -0.064938 0.700983 0.188017 0.070 Uiso 1 1 calc GR . . . .
Cl1 Cl -0.13507(7) 0.63975(11) 0.52720(6) 0.03504(16) 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
Br1 C4 1.905(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C10 1.488(3) . ?
N1 C11 1.497(3) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 C2 1.499(4) . ?
C2 C3 1.381(4) . ?
C2 C7 1.385(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(4) . ?
C4 C5 1.391(4) . ?
C5 C6 1.395(4) . ?
C5 C8 1.505(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(4) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.541(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.523(3) . ?
C9 C14 1.538(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.497(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.312(4) . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 107.5 . . ?
C10 N1 H1A 108.5 . . ?
C10 N1 H1B 108.5 . . ?
C10 N1 C11 115.01(18) . . ?
C11 N1 H1A 108.5 . . ?
C11 N1 H1B 108.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 C7 117.9(3) . . ?
C7 C2 C1 121.1(3) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 Br1 117.7(2) . . ?
C5 C4 Br1 119.8(2) . . ?
C5 C4 C3 122.5(3) . . ?
C4 C5 C6 116.0(2) . . ?
C4 C5 C8 123.6(3) . . ?
C6 C5 C8 120.4(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C2 C7 C6 121.4(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C5 C8 H8A 108.4 . . ?
C5 C8 H8B 108.4 . . ?
C5 C8 C9 115.4(2) . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C8 C9 H9 109.2 . . ?
C10 C9 C8 109.4(2) . . ?
C10 C9 H9 109.2 . . ?
C10 C9 C14 111.1(2) . . ?
C14 C9 C8 108.7(2) . . ?
C14 C9 H9 109.2 . . ?
N1 C10 C9 111.06(18) . . ?
N1 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N1 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
N1 C11 C12 112.06(19) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C11 C12 H12 118.6 . . ?
C13 C12 C11 122.7(3) . . ?
C13 C12 H12 118.6 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C5 C6 -179.19(19) . . . . ?
Br1 C4 C5 C8 0.5(3) . . . . ?
N1 C11 C12 C13 126.7(3) . . . . ?
C1 C2 C3 C4 179.8(3) . . . . ?
C1 C2 C7 C6 179.1(3) . . . . ?
C2 C3 C4 Br1 -179.6(2) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C2 C7 C6 0.5(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C8 179.3(2) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C4 C5 C8 C9 79.2(3) . . . . ?
C5 C6 C7 C2 0.6(4) . . . . ?
C5 C8 C9 C10 65.5(3) . . . . ?
C5 C8 C9 C14 -173.1(3) . . . . ?
C6 C5 C8 C9 -101.1(3) . . . . ?
C7 C2 C3 C4 -1.6(4) . . . . ?
C8 C5 C6 C7 179.6(2) . . . . ?
C8 C9 C10 N1 -175.1(2) . . . . ?
C10 N1 C11 C12 -58.0(3) . . . . ?
C11 N1 C10 C9 -178.0(2) . . . . ?
C14 C9 C10 N1 64.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.612
_oxdiff_exptl_absorpt_empirical_full_min 0.575
####################################################################### 
# 
# 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_r20230204b_autored
_database_code_depnum_ccdc_archive 'CCDC 2241442'
loop_
_audit_author_name
_audit_author_address
'Zefei Xu'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2023-02-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-N-(3-(2-bromo-4-fluorophenyl)-2-methylpropyl)prop-2-en-1-amine hydrochloride'
_chemical_formula_moiety         'C13 H18 Br F N, Cl'
_chemical_formula_sum            'C13 H18 Br Cl F N'
_chemical_formula_weight         322.64
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6197(2)
_cell_length_b                   14.1232(3)
_cell_length_c                   27.1001(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2916.37(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9281
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.2220
_cell_measurement_theta_min      2.6590
_shelx_estimated_absorpt_T_max   0.630
_shelx_estimated_absorpt_T_min   0.510
_exptl_absorpt_coefficient_mu    2.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16201
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.677
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00   6.00   0.50    2.00    --  -30.00 -70.00 180.00  252
  2  ω    -66.00  60.00   0.50    2.00    --  -30.00  70.00 180.00  252
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0044375000
_diffrn_orient_matrix_UB_12      -0.0368438000
_diffrn_orient_matrix_UB_13      -0.0177474000
_diffrn_orient_matrix_UB_21      0.0024778000
_diffrn_orient_matrix_UB_22      0.0340360000
_diffrn_orient_matrix_UB_23      -0.0192224000
_diffrn_orient_matrix_UB_31      0.0929645000
_diffrn_orient_matrix_UB_32      -0.0026904000
_diffrn_orient_matrix_UB_33      -0.0003306000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                6186
_reflns_number_total             7206
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Flack x determined using 2212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         7206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), N2(H2A,H2B), C20(H20A,
 H20B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C11(H11), C15(H15), C17(H17), C18(H18), C24(H24)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B), C25(H25A,H25B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.38839(7) 0.38676(3) 0.59303(2) 0.03454(14) Uani 1 1 d . . . . .
F1 F 0.4765(4) 0.2409(2) 0.42051(11) 0.0430(8) Uani 1 1 d . . . . .
N1 N 0.5749(5) 0.1404(2) 0.74567(13) 0.0214(8) Uani 1 1 d . . . . .
H1A H 0.580684 0.203539 0.752059 0.026 Uiso 1 1 calc R U . . .
H1B H 0.683249 0.120965 0.735831 0.026 Uiso 1 1 calc R U . . .
C1 C 0.4048(6) 0.2800(3) 0.55023(17) 0.0260(10) Uani 1 1 d . . . . .
C2 C 0.4365(7) 0.2988(3) 0.50087(19) 0.0316(11) Uani 1 1 d . . . . .
H2 H 0.451032 0.361876 0.489404 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4463(7) 0.2232(4) 0.46898(18) 0.0316(11) Uani 1 1 d . . . . .
C4 C 0.4266(7) 0.1312(3) 0.48453(19) 0.0352(12) Uani 1 1 d . . . . .
H4 H 0.435548 0.080158 0.461857 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3935(7) 0.1148(3) 0.53382(18) 0.0313(10) Uani 1 1 d . . . . .
H5 H 0.378898 0.051339 0.544743 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3808(6) 0.1881(3) 0.56828(17) 0.0254(9) Uani 1 1 d . . . . .
C7 C 0.3444(6) 0.1656(3) 0.62176(17) 0.0268(10) Uani 1 1 d . . . . .
H7A H 0.286681 0.102884 0.623563 0.032 Uiso 1 1 calc R U . . .
H7B H 0.260579 0.213005 0.634740 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5069(6) 0.1642(3) 0.65536(17) 0.0240(9) Uani 1 1 d . . . . .
H8 H 0.548409 0.230718 0.660394 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4476(6) 0.1237(3) 0.70506(16) 0.0238(9) Uani 1 1 d . . . . .
H9A H 0.333689 0.152611 0.714134 0.029 Uiso 1 1 calc R U . . .
H9B H 0.428883 0.054709 0.701438 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5253(7) 0.0889(3) 0.79209(18) 0.0302(11) Uani 1 1 d . . . . .
H10A H 0.408466 0.110824 0.803206 0.036 Uiso 1 1 calc R U . . .
H10B H 0.517045 0.020225 0.785069 0.036 Uiso 1 1 calc R U . . .
C11 C 0.6555(7) 0.1047(3) 0.83228(18) 0.0307(10) Uani 1 1 d . . . . .
H11 H 0.776346 0.095371 0.825102 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6115(9) 0.1309(3) 0.87730(19) 0.0377(12) Uani 1 1 d . . . . .
H12A H 0.491539 0.140634 0.885416 0.045 Uiso 1 1 calc R U . . .
H12B H 0.699654 0.140007 0.901617 0.045 Uiso 1 1 calc R U . . .
C13 C 0.6566(7) 0.1058(4) 0.63341(19) 0.0429(13) Uani 1 1 d . . . . .
H13A H 0.619284 0.039708 0.630125 0.064 Uiso 1 1 calc R U . . .
H13B H 0.759069 0.109282 0.655181 0.064 Uiso 1 1 calc R U . . .
H13C H 0.687379 0.130989 0.600840 0.064 Uiso 1 1 calc R U . . .
Br2 Br -0.14536(7) -0.06073(4) 0.53358(2) 0.04488(16) Uani 1 1 d . . . . .
F2 F 0.4635(5) -0.1663(2) 0.47190(12) 0.0509(9) Uani 1 1 d . . . . .
N2 N 0.0571(5) -0.1021(2) 0.75371(13) 0.0229(8) Uani 1 1 d . . . . .
H2A H 0.167287 -0.122742 0.746506 0.027 Uiso 1 1 calc R U . . .
H2B H 0.053362 -0.038736 0.747609 0.027 Uiso 1 1 calc R U . . .
C14 C 0.0907(6) -0.0993(3) 0.54587(18) 0.0297(10) Uani 1 1 d . . . . .
C15 C 0.1924(7) -0.1196(3) 0.50458(18) 0.0349(12) Uani 1 1 d . . . . .
H15 H 0.145592 -0.113843 0.472227 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3622(8) -0.1482(3) 0.51206(19) 0.0373(12) Uani 1 1 d . . . . .
C17 C 0.4320(7) -0.1573(3) 0.5578(2) 0.0347(12) Uani 1 1 d . . . . .
H17 H 0.549576 -0.178129 0.561983 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3285(7) -0.1357(3) 0.59843(18) 0.0301(11) Uani 1 1 d . . . . .
H18 H 0.377440 -0.141593 0.630521 0.036 Uiso 1 1 calc R U . . .
C19 C 0.1540(6) -0.1054(3) 0.59365(17) 0.0263(9) Uani 1 1 d . . . . .
C20 C 0.0521(6) -0.0833(3) 0.64040(17) 0.0267(10) Uani 1 1 d . . . . .
H20A H -0.057194 -0.049396 0.631557 0.032 Uiso 1 1 calc R U . . .
H20B H 0.123099 -0.040875 0.661526 0.032 Uiso 1 1 calc R U . . .
C21 C 0.0048(6) -0.1734(3) 0.66982(17) 0.0237(9) Uani 1 1 d . . . . .
H21 H 0.114308 -0.211437 0.674514 0.028 Uiso 1 1 calc R U . . .
C22 C -0.0714(6) -0.1512(3) 0.72058(16) 0.0246(9) Uani 1 1 d . . . . .
H22A H -0.176308 -0.110590 0.716515 0.030 Uiso 1 1 calc R U . . .
H22B H -0.109378 -0.210948 0.736408 0.030 Uiso 1 1 calc R U . . .
C23 C 0.0214(6) -0.1187(3) 0.80726(16) 0.0284(10) Uani 1 1 d . . . . .
H23A H 0.019914 -0.187664 0.813904 0.034 Uiso 1 1 calc R U . . .
H23B H -0.095375 -0.092839 0.815850 0.034 Uiso 1 1 calc R U . . .
C24 C 0.1587(7) -0.0725(3) 0.83859(17) 0.0323(11) Uani 1 1 d . . . . .
H24 H 0.276246 -0.093942 0.835173 0.039 Uiso 1 1 calc R U . . .
C25 C 0.1281(8) -0.0047(3) 0.87037(17) 0.0377(12) Uani 1 1 d . . . . .
H25A H 0.012054 0.018505 0.874754 0.045 Uiso 1 1 calc R U . . .
H25B H 0.221863 0.021403 0.889048 0.045 Uiso 1 1 calc R U . . .
C26 C -0.1297(8) -0.2352(3) 0.64241(17) 0.0340(11) Uani 1 1 d . . . . .
H26A H -0.244224 -0.203561 0.642551 0.051 Uiso 1 1 calc R U . . .
H26B H -0.139654 -0.296675 0.658921 0.051 Uiso 1 1 calc R U . . .
H26C H -0.091109 -0.244647 0.608268 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl 0.54470(14) 0.35501(7) 0.76683(4) 0.0261(2) Uani 1 1 d . . . . .
Cl2 Cl -0.01628(14) 0.11085(8) 0.73704(5) 0.0287(2) 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
Br1 C1 1.907(4) . ?
F1 C3 1.357(6) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C9 1.486(6) . ?
N1 C10 1.501(5) . ?
C1 C2 1.385(7) . ?
C1 C6 1.399(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(7) . ?
C3 C4 1.373(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(6) . ?
C6 C7 1.509(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.537(6) . ?
C8 H8 1.0000 . ?
C8 C9 1.532(6) . ?
C8 C13 1.528(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.490(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.318(7) . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
Br2 C14 1.909(5) . ?
F2 C16 1.358(6) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C22 1.499(6) . ?
N2 C23 1.495(5) . ?
C14 C15 1.391(7) . ?
C14 C19 1.384(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.371(8) . ?
C16 C17 1.354(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.403(7) . ?
C19 C20 1.518(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.545(6) . ?
C21 H21 1.0000 . ?
C21 C22 1.526(6) . ?
C21 C26 1.537(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.497(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.310(7) . ?
C25 H25A 0.9500 . ?
C25 H25B 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
H1A N1 H1B 107.9 . . ?
C9 N1 H1A 109.1 . . ?
C9 N1 H1B 109.1 . . ?
C9 N1 C10 112.3(3) . . ?
C10 N1 H1A 109.1 . . ?
C10 N1 H1B 109.1 . . ?
C2 C1 Br1 116.6(3) . . ?
C2 C1 C6 122.6(4) . . ?
C6 C1 Br1 120.8(4) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2 121.1 . . ?
F1 C3 C2 118.3(4) . . ?
F1 C3 C4 119.4(4) . . ?
C4 C3 C2 122.4(5) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.5(5) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.3(4) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C7 123.7(4) . . ?
C5 C6 C1 116.4(4) . . ?
C5 C6 C7 119.9(4) . . ?
C6 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C6 C7 C8 115.0(4) . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C7 C8 H8 108.9 . . ?
C9 C8 C7 106.7(4) . . ?
C9 C8 H8 108.9 . . ?
C13 C8 C7 112.2(4) . . ?
C13 C8 H8 108.9 . . ?
C13 C8 C9 111.1(4) . . ?
N1 C9 C8 113.6(4) . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N1 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 N1 111.9(4) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11 118.4 . . ?
C12 C11 C10 123.3(5) . . ?
C12 C11 H11 118.4 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H2A N2 H2B 107.8 . . ?
C22 N2 H2A 109.0 . . ?
C22 N2 H2B 109.0 . . ?
C23 N2 H2A 109.0 . . ?
C23 N2 H2B 109.0 . . ?
C23 N2 C22 112.9(3) . . ?
C15 C14 Br2 116.3(4) . . ?
C19 C14 Br2 120.6(4) . . ?
C19 C14 C15 123.1(5) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 C14 117.9(5) . . ?
C16 C15 H15 121.1 . . ?
F2 C16 C15 118.2(5) . . ?
C17 C16 F2 119.5(5) . . ?
C17 C16 C15 122.2(5) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(5) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 118.9 . . ?
C17 C18 C19 122.1(5) . . ?
C19 C18 H18 118.9 . . ?
C14 C19 C18 115.8(4) . . ?
C14 C19 C20 126.1(5) . . ?
C18 C19 C20 118.1(4) . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
C19 C20 C21 112.4(4) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C20 C21 H21 108.3 . . ?
C22 C21 C20 112.6(3) . . ?
C22 C21 H21 108.3 . . ?
C22 C21 C26 107.4(4) . . ?
C26 C21 C20 111.9(4) . . ?
C26 C21 H21 108.3 . . ?
N2 C22 C21 112.8(4) . . ?
N2 C22 H22A 109.0 . . ?
N2 C22 H22B 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 C24 110.8(4) . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C23 C24 H24 117.7 . . ?
C25 C24 C23 124.6(5) . . ?
C25 C24 H24 117.7 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -179.0(4) . . . . ?
Br1 C1 C6 C5 179.3(4) . . . . ?
Br1 C1 C6 C7 -1.2(7) . . . . ?
F1 C3 C4 C5 -179.1(4) . . . . ?
N1 C10 C11 C12 130.0(5) . . . . ?
C1 C2 C3 F1 179.7(4) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C1 C6 C7 C8 -80.7(6) . . . . ?
C2 C1 C6 C5 1.1(8) . . . . ?
C2 C1 C6 C7 -179.4(5) . . . . ?
C2 C3 C4 C5 0.9(8) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C4 C5 C6 C1 -0.5(8) . . . . ?
C4 C5 C6 C7 180.0(5) . . . . ?
C5 C6 C7 C8 98.8(5) . . . . ?
C6 C1 C2 C3 -0.8(8) . . . . ?
C6 C7 C8 C9 -170.4(4) . . . . ?
C6 C7 C8 C13 -48.4(5) . . . . ?
C7 C8 C9 N1 -165.0(4) . . . . ?
C9 N1 C10 C11 179.0(4) . . . . ?
C10 N1 C9 C8 -172.3(4) . . . . ?
C13 C8 C9 N1 72.5(5) . . . . ?
Br2 C14 C15 C16 -179.5(4) . . . . ?
Br2 C14 C19 C18 179.2(3) . . . . ?
Br2 C14 C19 C20 -0.4(6) . . . . ?
F2 C16 C17 C18 178.0(4) . . . . ?
N2 C23 C24 C25 117.4(5) . . . . ?
C14 C15 C16 F2 -178.6(4) . . . . ?
C14 C15 C16 C17 0.2(7) . . . . ?
C14 C19 C20 C21 107.9(5) . . . . ?
C15 C14 C19 C18 -1.3(6) . . . . ?
C15 C14 C19 C20 179.2(4) . . . . ?
C15 C16 C17 C18 -0.9(7) . . . . ?
C16 C17 C18 C19 0.5(7) . . . . ?
C17 C18 C19 C14 0.6(6) . . . . ?
C17 C18 C19 C20 -179.9(4) . . . . ?
C18 C19 C20 C21 -71.7(5) . . . . ?
C19 C14 C15 C16 0.9(7) . . . . ?
C19 C20 C21 C22 170.9(4) . . . . ?
C19 C20 C21 C26 -68.0(5) . . . . ?
C20 C21 C22 N2 -64.0(5) . . . . ?
C22 N2 C23 C24 177.0(4) . . . . ?
C23 N2 C22 C21 -153.7(4) . . . . ?
C26 C21 C22 N2 172.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.564
_oxdiff_exptl_absorpt_empirical_full_min 0.566
####################################################################### 
# 
# 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_r20230217e_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2242724'
loop_
_audit_author_name
_audit_author_address
'Zefei Xu'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2023-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-N-(3-(2-bromo-5-fluorophenyl)-2-methylpropyl)prop-2-en-1-amine hydrochloride'
_chemical_formula_moiety         'C13 H18 Br F N, Cl'
_chemical_formula_sum            'C13 H18 Br Cl F N'
_chemical_formula_weight         322.64
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H18 Br1 Cl1 F1 N1'
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.83350(10)
_cell_length_b                   26.0950(6)
_cell_length_c                   11.3444(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.954(2)
_cell_angle_gamma                90
_cell_volume                     1430.67(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17331
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      34.6170
_cell_measurement_theta_min      1.9940
_shelx_estimated_absorpt_T_max   0.641
_shelx_estimated_absorpt_T_min   0.390
_exptl_absorpt_coefficient_mu    3.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11088
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_min         1.561
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    2.00    --  -20.00   0.00  90.00  360
  2  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00 180.00  234
  3  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00   0.00  234
  4  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00  90.00  234
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 944'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0149038000
_diffrn_orient_matrix_UB_12      0.0269507000
_diffrn_orient_matrix_UB_13      0.0050336000
_diffrn_orient_matrix_UB_21      0.0000876000
_diffrn_orient_matrix_UB_22      -0.0021507000
_diffrn_orient_matrix_UB_23      0.0623208000
_diffrn_orient_matrix_UB_31      0.1460225000
_diffrn_orient_matrix_UB_32      -0.0027447000
_diffrn_orient_matrix_UB_33      0.0005628000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                10181
_reflns_number_total             11088
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.866
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.170
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.004(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         11088
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1259P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1472
_refine_special_details          
;
 Refined as a 3-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.47(5)
 0.37(2) 0.16(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C3(H3A,H3B), C11(H11A,H11B), N2(H2A,H2B), C14(H14A,
 H14B), C16(H16A,H16B), C24(H24A,H24B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C12(H12), C19(H19), C20(H20), C22(H22), C25(H25)
3.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B), C26(H26A,H26B)
3.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.00977(11) 0.51935(2) 0.63645(7) 0.0205(2) Uani 1 1 d . . . . .
F1 F 0.8418(9) 0.5800(2) 0.2779(5) 0.0325(13) Uani 1 1 d . . . . .
N1 N 0.3086(10) 0.7528(2) 0.6215(5) 0.0137(12) Uani 1 1 d . . . . .
H1A H 0.155161 0.748697 0.574871 0.016 Uiso 1 1 calc R . . . .
H1B H 0.459538 0.749786 0.575053 0.016 Uiso 1 1 calc R . . . .
C1 C 0.3162(13) 0.7115(3) 0.7130(7) 0.0174(15) Uani 1 1 d . . . . .
H1C H 0.128056 0.706605 0.744244 0.021 Uiso 1 1 calc R . . . .
H1D H 0.439027 0.722269 0.779177 0.021 Uiso 1 1 calc R . . . .
C2 C 0.4193(12) 0.6611(3) 0.6635(7) 0.0160(13) Uani 1 1 d . . . . .
H2 H 0.592476 0.668164 0.619314 0.019 Uiso 1 1 calc R . . . .
C3 C 0.2086(12) 0.6362(3) 0.5774(7) 0.0169(14) Uani 1 1 d . . . . .
H3A H 0.050474 0.622911 0.622572 0.020 Uiso 1 1 calc R . . . .
H3B H 0.136971 0.662637 0.522246 0.020 Uiso 1 1 calc R . . . .
C4 C 0.3329(12) 0.5930(3) 0.5076(7) 0.0162(15) Uani 1 1 d . . . . .
C5 C 0.2646(12) 0.5411(3) 0.5209(7) 0.0153(16) Uani 1 1 d . . . . .
C6 C 0.3819(12) 0.5031(3) 0.4526(8) 0.0207(16) Uani 1 1 d . . . . .
H6 H 0.329645 0.468402 0.463568 0.025 Uiso 1 1 calc R . . . .
C7 C 0.5770(14) 0.5157(3) 0.3676(8) 0.0232(16) Uani 1 1 d . . . . .
H7 H 0.656732 0.490282 0.318639 0.028 Uiso 1 1 calc R . . . .
C8 C 0.6472(13) 0.5664(3) 0.3583(7) 0.0209(16) Uani 1 1 d . . . . .
C9 C 0.5314(13) 0.6049(3) 0.4242(7) 0.0182(16) Uani 1 1 d . . . . .
H9 H 0.586602 0.639450 0.412792 0.022 Uiso 1 1 calc R . . . .
C10 C 0.4918(16) 0.6244(4) 0.7649(7) 0.0253(17) Uani 1 1 d . . . . .
H10A H 0.325348 0.617291 0.810268 0.038 Uiso 1 1 calc GR . . . .
H10B H 0.632322 0.640220 0.816534 0.038 Uiso 1 1 calc GR . . . .
H10C H 0.564092 0.592340 0.732829 0.038 Uiso 1 1 calc GR . . . .
C11 C 0.3050(15) 0.8060(3) 0.6760(8) 0.0242(17) Uani 1 1 d . . . . .
H11A H 0.134787 0.810346 0.722270 0.029 Uiso 1 1 calc R . . . .
H11B H 0.466228 0.810040 0.730179 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3148(15) 0.8458(3) 0.5826(8) 0.0262(17) Uani 1 1 d . . . . .
H12 H 0.454540 0.843314 0.524980 0.031 Uiso 1 1 calc R . . . .
C13 C 0.1394(18) 0.8845(4) 0.5754(9) 0.031(2) Uani 1 1 d . . . . .
H13A H -0.002314 0.887867 0.631902 0.038 Uiso 1 1 calc R . . . .
H13B H 0.154920 0.908888 0.513798 0.038 Uiso 1 1 calc R . . . .
Br2 Br 0.48476(11) 0.48069(2) 0.86209(7) 0.0200(2) Uani 1 1 d . . . . .
F2 F 1.3420(8) 0.4154(2) 1.2181(5) 0.0266(11) Uani 1 1 d . . . . .
N2 N 0.6709(10) 0.2470(3) 0.8787(6) 0.0163(12) Uani 1 1 d . . . . .
H2A H 0.527466 0.254797 0.926391 0.020 Uiso 1 1 calc R . . . .
H2B H 0.827678 0.245399 0.924061 0.020 Uiso 1 1 calc R . . . .
C14 C 0.7014(13) 0.2886(3) 0.7871(7) 0.0173(15) Uani 1 1 d . . . . .
H14A H 0.516756 0.297135 0.753539 0.021 Uiso 1 1 calc R . . . .
H14B H 0.817099 0.275702 0.722332 0.021 Uiso 1 1 calc R . . . .
C15 C 0.8329(12) 0.3369(3) 0.8388(7) 0.0159(14) Uani 1 1 d . . . . .
H15 H 1.009935 0.326765 0.879257 0.019 Uiso 1 1 calc R . . . .
C16 C 0.6490(12) 0.3629(3) 0.9305(7) 0.0165(14) Uani 1 1 d . . . . .
H16A H 0.481162 0.376567 0.890446 0.020 Uiso 1 1 calc R . . . .
H16B H 0.589457 0.336965 0.988554 0.020 Uiso 1 1 calc R . . . .
C17 C 0.7956(12) 0.4058(3) 0.9942(7) 0.0163(15) Uani 1 1 d . . . . .
C18 C 0.7414(12) 0.4576(3) 0.9799(8) 0.0169(17) Uani 1 1 d . . . . .
C19 C 0.8756(13) 0.4952(3) 1.0468(8) 0.0217(17) Uani 1 1 d . . . . .
H19 H 0.829871 0.530257 1.035756 0.026 Uiso 1 1 calc R . . . .
C20 C 1.0765(14) 0.4812(3) 1.1296(7) 0.0226(16) Uani 1 1 d . . . . .
H20 H 1.167614 0.506102 1.177383 0.027 Uiso 1 1 calc R . . . .
C21 C 1.1385(12) 0.4300(3) 1.1398(7) 0.0190(15) Uani 1 1 d . . . . .
C22 C 1.0039(13) 0.3922(3) 1.0776(7) 0.0177(16) Uani 1 1 d . . . . .
H22 H 1.050048 0.357269 1.090284 0.021 Uiso 1 1 calc R . . . .
C23 C 0.9041(15) 0.3725(3) 0.7376(7) 0.0228(16) Uani 1 1 d . . . . .
H23A H 1.028711 0.354830 0.683758 0.034 Uiso 1 1 calc GR . . . .
H23B H 0.995237 0.403253 0.768903 0.034 Uiso 1 1 calc GR . . . .
H23C H 0.734148 0.382242 0.694988 0.034 Uiso 1 1 calc GR . . . .
C24 C 0.6191(15) 0.1953(3) 0.8217(8) 0.0226(16) Uani 1 1 d . . . . .
H24A H 0.455411 0.197447 0.768261 0.027 Uiso 1 1 calc R . . . .
H24B H 0.780689 0.185539 0.774069 0.027 Uiso 1 1 calc R . . . .
C25 C 0.5713(14) 0.1556(3) 0.9129(7) 0.0242(16) Uani 1 1 d . . . . .
H25 H 0.425548 0.160779 0.966813 0.029 Uiso 1 1 calc R . . . .
C26 C 0.7211(19) 0.1136(4) 0.9230(9) 0.034(2) Uani 1 1 d . . . . .
H26A H 0.868041 0.107477 0.870175 0.040 Uiso 1 1 calc R . . . .
H26B H 0.682038 0.089342 0.982957 0.040 Uiso 1 1 calc R . . . .
Cl1 Cl 0.8013(3) 0.74547(8) 0.44669(17) 0.0188(4) Uani 1 1 d . . . . .
Cl2 Cl 0.1786(3) 0.25440(8) 1.05533(16) 0.0181(4) 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
Br1 C5 1.900(8) . ?
F1 C8 1.369(9) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.496(10) . ?
N1 C11 1.521(10) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.517(11) . ?
C2 H2 1.0000 . ?
C2 C3 1.543(10) . ?
C2 C10 1.532(11) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.510(10) . ?
C4 C5 1.402(11) . ?
C4 C9 1.394(10) . ?
C5 C6 1.385(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(11) . ?
C7 H7 0.9500 . ?
C7 C8 1.371(12) . ?
C8 C9 1.376(12) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.485(12) . ?
C12 H12 0.9500 . ?
C12 C13 1.319(12) . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
Br2 C18 1.905(8) . ?
F2 C21 1.368(8) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C14 1.511(10) . ?
N2 C24 1.515(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.525(11) . ?
C15 H15 1.0000 . ?
C15 C16 1.537(10) . ?
C15 C23 1.520(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.504(10) . ?
C17 C18 1.388(12) . ?
C17 C22 1.414(10) . ?
C18 C19 1.392(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(11) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(12) . ?
C21 C22 1.369(11) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.485(12) . ?
C25 H25 0.9500 . ?
C25 C26 1.318(12) . ?
C26 H26A 0.9500 . ?
C26 H26B 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
H1A N1 H1B 107.9 . . ?
C1 N1 H1A 109.2 . . ?
C1 N1 H1B 109.2 . . ?
C1 N1 C11 112.1(6) . . ?
C11 N1 H1A 109.2 . . ?
C11 N1 H1B 109.2 . . ?
N1 C1 H1C 109.2 . . ?
N1 C1 H1D 109.2 . . ?
N1 C1 C2 111.8(6) . . ?
H1C C1 H1D 107.9 . . ?
C2 C1 H1C 109.2 . . ?
C2 C1 H1D 109.2 . . ?
C1 C2 H2 108.0 . . ?
C1 C2 C3 112.4(6) . . ?
C1 C2 C10 109.7(7) . . ?
C3 C2 H2 108.0 . . ?
C10 C2 H2 108.0 . . ?
C10 C2 C3 110.6(6) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 112.5(5) . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C5 C4 C3 124.7(6) . . ?
C9 C4 C3 118.3(7) . . ?
C9 C4 C5 117.1(7) . . ?
C4 C5 Br1 121.3(6) . . ?
C6 C5 Br1 116.7(6) . . ?
C6 C5 C4 122.0(7) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(8) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 121.7 . . ?
C8 C7 C6 116.7(7) . . ?
C8 C7 H7 121.7 . . ?
F1 C8 C7 118.5(7) . . ?
F1 C8 C9 117.5(7) . . ?
C7 C8 C9 124.0(7) . . ?
C4 C9 H9 120.1 . . ?
C8 C9 C4 119.7(7) . . ?
C8 C9 H9 120.1 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 N1 110.4(7) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C11 C12 H12 118.3 . . ?
C13 C12 C11 123.4(8) . . ?
C13 C12 H12 118.3 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
H2A N2 H2B 108.0 . . ?
C14 N2 H2A 109.4 . . ?
C14 N2 H2B 109.4 . . ?
C14 N2 C24 111.3(6) . . ?
C24 N2 H2A 109.4 . . ?
C24 N2 H2B 109.4 . . ?
N2 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
N2 C14 C15 112.0(6) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C14 C15 H15 107.8 . . ?
C14 C15 C16 112.5(5) . . ?
C16 C15 H15 107.8 . . ?
C23 C15 C14 108.2(6) . . ?
C23 C15 H15 107.8 . . ?
C23 C15 C16 112.5(6) . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 112.4(5) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C18 C17 C16 125.7(6) . . ?
C18 C17 C22 116.9(7) . . ?
C22 C17 C16 117.4(7) . . ?
C17 C18 Br2 120.6(6) . . ?
C17 C18 C19 122.5(7) . . ?
C19 C18 Br2 116.9(6) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.9(8) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 121.3 . . ?
C21 C20 C19 117.5(7) . . ?
C21 C20 H20 121.3 . . ?
F2 C21 C20 118.6(7) . . ?
F2 C21 C22 117.7(7) . . ?
C22 C21 C20 123.7(7) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.5(8) . . ?
C21 C22 H22 120.2 . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
C15 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.6 . . ?
N2 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 N2 110.5(7) . . ?
C25 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C24 C25 H25 118.4 . . ?
C26 C25 C24 123.3(7) . . ?
C26 C25 H25 118.4 . . ?
C25 C26 H26A 120.0 . . ?
C25 C26 H26B 120.0 . . ?
H26A C26 H26B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C5 C6 C7 -178.3(5) . . . . ?
F1 C8 C9 C4 -179.8(6) . . . . ?
N1 C1 C2 C3 -70.5(7) . . . . ?
N1 C1 C2 C10 166.0(5) . . . . ?
N1 C11 C12 C13 129.1(9) . . . . ?
C1 N1 C11 C12 176.6(5) . . . . ?
C1 C2 C3 C4 167.0(6) . . . . ?
C2 C3 C4 C5 111.2(8) . . . . ?
C2 C3 C4 C9 -68.3(9) . . . . ?
C3 C4 C5 Br1 -2.4(10) . . . . ?
C3 C4 C5 C6 178.7(7) . . . . ?
C3 C4 C9 C8 -179.5(6) . . . . ?
C4 C5 C6 C7 0.5(11) . . . . ?
C5 C4 C9 C8 1.0(11) . . . . ?
C5 C6 C7 C8 1.4(11) . . . . ?
C6 C7 C8 F1 178.6(6) . . . . ?
C6 C7 C8 C9 -2.3(11) . . . . ?
C7 C8 C9 C4 1.1(12) . . . . ?
C9 C4 C5 Br1 177.1(5) . . . . ?
C9 C4 C5 C6 -1.7(11) . . . . ?
C10 C2 C3 C4 -70.0(8) . . . . ?
C11 N1 C1 C2 -160.0(5) . . . . ?
Br2 C18 C19 C20 -176.4(6) . . . . ?
F2 C21 C22 C17 -178.9(6) . . . . ?
N2 C14 C15 C16 -65.5(7) . . . . ?
N2 C14 C15 C23 169.6(5) . . . . ?
N2 C24 C25 C26 -122.9(9) . . . . ?
C14 N2 C24 C25 -176.3(5) . . . . ?
C14 C15 C16 C17 171.4(6) . . . . ?
C15 C16 C17 C18 108.5(8) . . . . ?
C15 C16 C17 C22 -72.6(8) . . . . ?
C16 C17 C18 Br2 -5.7(10) . . . . ?
C16 C17 C18 C19 176.4(7) . . . . ?
C16 C17 C22 C21 -178.5(6) . . . . ?
C17 C18 C19 C20 1.5(12) . . . . ?
C18 C17 C22 C21 0.6(11) . . . . ?
C18 C19 C20 C21 1.4(12) . . . . ?
C19 C20 C21 F2 177.9(7) . . . . ?
C19 C20 C21 C22 -3.5(12) . . . . ?
C20 C21 C22 C17 2.5(12) . . . . ?
C22 C17 C18 Br2 175.4(5) . . . . ?
C22 C17 C18 C19 -2.5(11) . . . . ?
C23 C15 C16 C17 -66.0(8) . . . . ?
C24 N2 C14 C15 -163.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.392
_oxdiff_exptl_absorpt_empirical_full_min 0.646
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.47(5)
2 0.37(2)
3 0.16(5)

_twin_special_details            
;
Component 2 rotated by 179.9842° 
around [1.00 0.00 -0.04] (reciprocal) or [1.00 0.00 -0.00] (direct)
;
####################################################################### 
# 
# 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_r20230204c_autored
_database_code_depnum_ccdc_archive 'CCDC 2241443'
loop_
_audit_author_name
_audit_author_address
'Zefei Xu'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2023-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(S)-N-(3-(2-bromo-6-fluorophenyl)-2-methylpropyl)prop-2-en-1-amine hydrochloride'
_chemical_formula_moiety         'C13 H18 Br F N, Cl'
_chemical_formula_sum            'C13 H18 Br Cl F N'
_chemical_formula_weight         322.64
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.7559(2)
_cell_length_b                   10.6799(4)
_cell_length_c                   28.6366(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1454.53(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5349
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      35.4200
_cell_measurement_theta_min      2.1030
_shelx_estimated_absorpt_T_max   0.614
_shelx_estimated_absorpt_T_min   0.498
_exptl_absorpt_coefficient_mu    3.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            8772
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         2.035
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  36.00   0.50    8.00    --  -30.00  70.00  90.00  204
  2  ω    -66.00  21.00   0.50    8.00    --  -30.00  70.00   0.00  174
  3  ω    -83.00   2.00   0.50    8.00    --  -30.00 -70.00  90.00  170
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'rigaku saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0176441000
_diffrn_orient_matrix_UB_12      0.0598813000
_diffrn_orient_matrix_UB_13      -0.0102875000
_diffrn_orient_matrix_UB_21      0.0174421000
_diffrn_orient_matrix_UB_22      0.0284674000
_diffrn_orient_matrix_UB_23      0.0221939000
_diffrn_orient_matrix_UB_31      0.1470797000
_diffrn_orient_matrix_UB_32      0.0038650000
_diffrn_orient_matrix_UB_33      -0.0038687000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3175
_reflns_number_total             3566
_reflns_odcompleteness_completeness 98.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1122 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+0.4073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0879
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.82195(10) 0.23597(4) 0.40593(2) 0.03695(15) Uani 1 1 d . . . . .
F1 F 0.3291(7) 0.6610(3) 0.44181(10) 0.0454(7) Uani 1 1 d . . . . .
N1 N 0.6690(7) 0.5196(3) 0.25138(9) 0.0158(6) Uani 1 1 d . . . . .
H1A H 0.807563 0.461145 0.253647 0.019 Uiso 1 1 calc R . . . .
H1B H 0.751185 0.596517 0.252249 0.019 Uiso 1 1 calc R . . . .
C1 C 0.7411(9) 0.3799(4) 0.44244(13) 0.0251(9) Uani 1 1 d . . . . .
C2 C 0.8710(11) 0.3889(5) 0.48611(15) 0.0353(11) Uani 1 1 d . . . . .
H2 H 0.996152 0.325511 0.496616 0.042 Uiso 1 1 calc R . . . .
C3 C 0.8127(12) 0.4925(5) 0.51381(16) 0.0406(12) Uani 1 1 d . . . . .
H3 H 0.901972 0.501041 0.543316 0.049 Uiso 1 1 calc R . . . .
C4 C 0.6269(12) 0.5832(5) 0.49892(15) 0.0395(12) Uani 1 1 d . . . . .
H4 H 0.583698 0.653287 0.518032 0.047 Uiso 1 1 calc R . . . .
C5 C 0.5054(10) 0.5692(5) 0.45551(15) 0.0309(10) Uani 1 1 d . . . . .
C6 C 0.5568(8) 0.4699(4) 0.42526(13) 0.0212(8) Uani 1 1 d . . . . .
C7 C 0.4288(8) 0.4667(4) 0.37701(13) 0.0206(8) Uani 1 1 d . . . . .
H7A H 0.255939 0.518406 0.376892 0.025 Uiso 1 1 calc R . . . .
H7B H 0.374159 0.379590 0.369511 0.025 Uiso 1 1 calc R . . . .
C8 C 0.6297(7) 0.5152(4) 0.33891(12) 0.0167(7) Uani 1 1 d . . . . .
H8 H 0.796582 0.458394 0.337603 0.020 Uiso 1 1 calc R . . . .
C9 C 0.4742(8) 0.5066(4) 0.29235(13) 0.0185(8) Uani 1 1 d . . . . .
H9A H 0.376590 0.424829 0.290461 0.022 Uiso 1 1 calc R . . . .
H9B H 0.329879 0.573248 0.290910 0.022 Uiso 1 1 calc R . . . .
C10 C 0.5199(9) 0.5039(4) 0.20540(13) 0.0218(9) Uani 1 1 d . . . . .
H10A H 0.444932 0.417634 0.202942 0.026 Uiso 1 1 calc R . . . .
H10B H 0.359611 0.562855 0.203666 0.026 Uiso 1 1 calc R . . . .
C11 C 0.7191(9) 0.5285(4) 0.16567(13) 0.0241(9) Uani 1 1 d . . . . .
H11 H 0.763656 0.613131 0.158614 0.029 Uiso 1 1 calc R . . . .
C12 C 0.8349(10) 0.4410(5) 0.14024(15) 0.0330(10) Uani 1 1 d . . . . .
H12A H 0.794734 0.355451 0.146393 0.040 Uiso 1 1 calc R . . . .
H12B H 0.959231 0.462947 0.115603 0.040 Uiso 1 1 calc R . . . .
C13 C 0.7330(8) 0.6477(4) 0.34894(14) 0.0224(8) Uani 1 1 d . . . . .
H13A H 0.571603 0.704533 0.350950 0.034 Uiso 1 1 calc GR . . . .
H13B H 0.857893 0.675103 0.323712 0.034 Uiso 1 1 calc GR . . . .
H13C H 0.835750 0.648655 0.378596 0.034 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.96147(17) 0.26338(9) 0.26169(3) 0.0219(2) 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
Br1 C1 1.899(4) . ?
F1 C5 1.348(6) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C9 1.502(5) . ?
N1 C10 1.505(4) . ?
C1 C2 1.398(6) . ?
C1 C6 1.391(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(6) . ?
C5 C6 1.391(6) . ?
C6 C7 1.510(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.540(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.527(5) . ?
C8 C13 1.525(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.504(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.306(6) . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
H1A N1 H1B 107.8 . . ?
C9 N1 H1A 109.1 . . ?
C9 N1 H1B 109.1 . . ?
C9 N1 C10 112.5(3) . . ?
C10 N1 H1A 109.1 . . ?
C10 N1 H1B 109.1 . . ?
C2 C1 Br1 117.3(3) . . ?
C6 C1 Br1 119.5(3) . . ?
C6 C1 C2 123.2(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.1(5) . . ?
C5 C4 H4 120.9 . . ?
F1 C5 C4 116.4(4) . . ?
F1 C5 C6 118.9(4) . . ?
C4 C5 C6 124.8(5) . . ?
C1 C6 C5 114.7(4) . . ?
C1 C6 C7 124.2(4) . . ?
C5 C6 C7 121.1(4) . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C6 C7 C8 113.0(3) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8 108.3 . . ?
C9 C8 C7 107.3(3) . . ?
C9 C8 H8 108.3 . . ?
C13 C8 C7 112.2(3) . . ?
C13 C8 H8 108.3 . . ?
C13 C8 C9 112.1(3) . . ?
N1 C9 C8 112.2(3) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N1 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 N1 110.2(3) . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C10 C11 H11 117.9 . . ?
C12 C11 C10 124.2(4) . . ?
C12 C11 H11 117.9 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -179.2(4) . . . . ?
Br1 C1 C6 C5 177.9(3) . . . . ?
Br1 C1 C6 C7 -4.8(6) . . . . ?
F1 C5 C6 C1 -180.0(4) . . . . ?
F1 C5 C6 C7 2.7(6) . . . . ?
N1 C10 C11 C12 103.0(5) . . . . ?
C1 C2 C3 C4 1.3(7) . . . . ?
C1 C6 C7 C8 -80.4(5) . . . . ?
C2 C1 C6 C5 -1.4(6) . . . . ?
C2 C1 C6 C7 175.8(4) . . . . ?
C2 C3 C4 C5 -1.3(8) . . . . ?
C3 C4 C5 F1 -178.7(4) . . . . ?
C3 C4 C5 C6 -0.1(8) . . . . ?
C4 C5 C6 C1 1.4(7) . . . . ?
C4 C5 C6 C7 -175.9(4) . . . . ?
C5 C6 C7 C8 96.7(4) . . . . ?
C6 C1 C2 C3 0.2(7) . . . . ?
C6 C7 C8 C9 179.9(4) . . . . ?
C6 C7 C8 C13 -56.5(4) . . . . ?
C7 C8 C9 N1 -165.4(3) . . . . ?
C9 N1 C10 C11 175.3(3) . . . . ?
C10 N1 C9 C8 176.8(3) . . . . ?
C13 C8 C9 N1 71.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.625
_oxdiff_exptl_absorpt_empirical_full_min 0.550
