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

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

data_PMN21
_database_code_depnum_ccdc_archive 'CCDC 1978969'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Southeast University
China
;
_audit_update_record             
;
2020-01-19 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H8 F2 N, Cl'
_chemical_formula_sum            'C4 H8 Cl F2 N'
_chemical_formula_weight         143.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'

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

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

_cell_length_a                   6.0473(4)
_cell_length_b                   7.0878(5)
_cell_length_c                   7.6493(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     327.86(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1435
_cell_measurement_theta_min      2.8640
_cell_measurement_theta_max      26.2930

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.519
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3075
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         31.227
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1161
_reflns_number_gt                807
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.720
_reflns_Friedel_fraction_full    0.970

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.0268P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 306 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.69(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1161
_refine_ls_number_parameters     46
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0000 0.5168(4) 0.3944(5) 0.0454(7) Uani 1 2 d S T P . .
H1A H 0.1268 0.4573 0.4156 0.068 Uiso 1 1 d R U . . .
H1B H 0.0000 0.5348 0.2798 0.068 Uiso 1 2 d R U P . .
Cl1 Cl 0.0000 0.60563(14) 0.98644(11) 0.0515(3) Uani 1 2 d S T P . .
F2 F 0.0000 1.1013(4) 0.5697(4) 0.0611(7) Uani 1 2 d S T P . .
C3 C 0.0000 0.7012(5) 0.4844(6) 0.0393(6) Uani 1 2 d S T P . .
H3 H 0.0000 0.6854 0.6117 0.047 Uiso 1 2 calc R U P . .
F1 F 0.0000 1.1141(3) 0.2894(4) 0.0780(10) Uani 1 2 d S T P . .
C2 C 0.1792(4) 0.8407(4) 0.4263(4) 0.0492(7) Uani 1 1 d . . . . .
H2A H 0.2939 0.8622 0.5126 0.059 Uiso 1 1 calc R U . . .
H2B H 0.2418 0.8137 0.3122 0.059 Uiso 1 1 calc R U . . .
C1 C 0.0000 0.9893(5) 0.4245(5) 0.0435(8) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.477(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8856 . ?
F2 C1 1.365(5) . ?
C3 C2 1.533(4) . ?
C3 C2 1.533(4) 4 ?
C3 H3 0.9800 . ?
F1 C1 1.360(5) . ?
C2 C1 1.511(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 C2 1.511(4) 4 ?

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
C3 N1 H1A 109.5 . . ?
C3 N1 H1B 109.5 . . ?
H1A N1 H1B 104.4 . . ?
N1 C3 C2 115.8(3) . . ?
N1 C3 C2 115.8(3) . 4 ?
C2 C3 C2 90.0(3) . 4 ?
N1 C3 H3 111.2 . . ?
C2 C3 H3 111.2 . . ?
C2 C3 H3 111.2 4 . ?
C1 C2 C3 86.88(19) . . ?
C1 C2 H2A 114.2 . . ?
C3 C2 H2A 114.2 . . ?
C1 C2 H2B 114.2 . . ?
C3 C2 H2B 114.2 . . ?
H2A C2 H2B 111.3 . . ?
F1 C1 F2 103.9(3) . . ?
F1 C1 C2 117.4(2) . 4 ?
F2 C1 C2 113.4(2) . 4 ?
F1 C1 C2 117.4(2) . . ?
F2 C1 C2 113.4(2) . . ?
C2 C1 C2 91.6(3) 4 . ?

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 C3 C2 C1 135.1(3) . . . . ?
C2 C3 C2 C1 16.1(3) 4 . . . ?
C3 C2 C1 F1 -138.6(3) . . . . ?
C3 C2 C1 F2 100.1(3) . . . . ?
C3 C2 C1 C2 -16.4(3) . . . 4 ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_PCA21
_database_code_depnum_ccdc_archive 'CCDC 1978970'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Southeast University
China
;
_audit_update_record             
;
2020-01-19 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 F N, Cl'
_chemical_formula_sum            'C4 H9 Cl F N'
_chemical_formula_weight         125.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   9.6909(5)
_cell_length_b                   7.0939(4)
_cell_length_c                   9.3284(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     641.29(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2975
_cell_measurement_theta_min      2.8910
_cell_measurement_theta_max      29.3940

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    0.499
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5489
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.871
_diffrn_reflns_theta_max         31.603
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2160
_reflns_number_gt                1460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.695
_reflns_Friedel_fraction_full    0.937

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1529P)²+0.4484P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.99(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2160
_refine_ls_number_parameters     59
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2405
_refine_ls_wR_factor_gt          0.2313
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0844(4) 0.5143(5) 0.1478(5) 0.0600(7) Uani 1 1 d . U . . .
H1 H 0.1650 0.5766 0.1056 0.072 Uiso 1 1 calc R U . . .
C2 C 0.0466(5) 0.3507(5) 0.0605(4) 0.0640(10) Uani 1 1 d . U . . .
H2A H 0.0756 0.3595 -0.0388 0.077 Uiso 1 1 calc R U . . .
H2B H -0.0499 0.3154 0.0677 0.077 Uiso 1 1 calc R U . . .
C3 C 0.1422(4) 0.2344(5) 0.1542(5) 0.0600(7) Uani 1 1 d . U . . .
H3 H 0.2355 0.2286 0.1140 0.072 Uiso 1 1 calc R U . . .
C4 C 0.1308(4) 0.3886(5) 0.2714(5) 0.0540(9) Uani 1 1 d . U . . .
H4A H 0.0606 0.3651 0.3433 0.065 Uiso 1 1 calc R U . . .
H4B H 0.2180 0.4246 0.3145 0.065 Uiso 1 1 calc R U . . .
Cl1 Cl 0.17594(8) 0.88394(11) 0.89030(12) 0.05320(18) Uani 1 1 d . U . . .
F1 F -0.0150(3) 0.6485(3) 0.1811(4) 0.0764(7) Uani 1 1 d . U . . .
N1 N 0.0928(3) 0.0457(4) 0.1974(3) 0.0479(6) Uani 1 1 d . U . . .
H1A H 0.1545 -0.0077 0.2553 0.072 Uiso 1 1 calc R U . . .
H1B H 0.0814 -0.0257 0.1199 0.072 Uiso 1 1 calc R U . . .
H1C H 0.0126 0.0568 0.2432 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.389(4) . ?
C1 C2 1.465(6) . ?
C1 C4 1.525(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.518(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.478(5) . ?
C3 C4 1.551(6) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?

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
F1 C1 C2 119.6(3) . . ?
F1 C1 C4 115.8(4) . . ?
C2 C1 C4 91.8(3) . . ?
F1 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C4 C1 H1 109.5 . . ?
C1 C2 C3 87.5(3) . . ?
C1 C2 H2A 114.1 . . ?
C3 C2 H2A 114.1 . . ?
C1 C2 H2B 114.1 . . ?
C3 C2 H2B 114.1 . . ?
H2A C2 H2B 111.2 . . ?
N1 C3 C2 116.9(3) . . ?
N1 C3 C4 115.1(3) . . ?
C2 C3 C4 88.8(3) . . ?
N1 C3 H3 111.4 . . ?
C2 C3 H3 111.4 . . ?
C4 C3 H3 111.4 . . ?
C1 C4 C3 84.3(3) . . ?
C1 C4 H4A 114.6 . . ?
C3 C4 H4A 114.6 . . ?
C1 C4 H4B 114.6 . . ?
C3 C4 H4B 114.6 . . ?
H4A C4 H4B 111.7 . . ?
C3 N1 H1A 109.5 . . ?
C3 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C3 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 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
F1 C1 C2 C3 -142.3(4) . . . . ?
C4 C1 C2 C3 -21.1(3) . . . . ?
C1 C2 C3 N1 138.4(3) . . . . ?
C1 C2 C3 C4 20.7(3) . . . . ?
F1 C1 C4 C3 145.0(3) . . . . ?
C2 C1 C4 C3 20.7(3) . . . . ?
N1 C3 C4 C1 -139.2(3) . . . . ?
C2 C3 C4 C1 -19.9(3) . . . . ?

_refine_diff_density_max         1.560
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.100



####################################################################### 
# 
# 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_PCA21_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1978973'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Southeast University
China
;
_audit_update_record             
;
2020-01-19 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 F N, Cl'
_chemical_formula_sum            'C4 H9 Cl F N'
_chemical_formula_weight         125.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   9.7193(18)
_cell_length_b                   7.1016(10)
_cell_length_c                   9.3503(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     645.38(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    360(2)
_cell_measurement_reflns_used    1549
_cell_measurement_theta_min      3.5270
_cell_measurement_theta_max      29.2630

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.496
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      360(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2743
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.868
_diffrn_reflns_theta_max         30.816
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.796
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.796
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.693
_diffrn_reflns_point_group_measured_fraction_full 0.920
_reflns_number_total             2018
_reflns_number_gt                1054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_max     0.577
_reflns_Friedel_fraction_full    0.848

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     74
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_ref         0.3092
_refine_ls_wR_factor_gt          0.2659
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1435(5) 0.2648(6) 0.1929(6) 0.0607(12) Uani 1 1 d . . . . .
H1D H 0.2364 0.2704 0.2332 0.073 Uiso 1 1 calc R U . . .
C2 C 0.0456(9) 0.1509(7) 0.2872(6) 0.0824(19) Uani 1 1 d . . . . .
H2A H -0.0289 0.2230 0.3266 0.099 Uiso 1 1 d R U . . .
H2B H 0.0914 0.0784 0.3597 0.099 Uiso 1 1 d R U . . .
C3 C 0.0072(18) 0.0437(16) 0.159(2) 0.095(4) Uani 0.5 1 d . U P . .
H3A H -0.0728 0.1010 0.1175 0.114 Uiso 0.5 1 d R U P . .
C3' C 0.0875(9) -0.0157(11) 0.2027(13) 0.064(3) Uani 0.5 1 d . U P . .
H3'A H 0.1664 -0.0757 0.2444 0.076 Uiso 0.5 1 d R U P . .
C4 C 0.1300(7) 0.1104(7) 0.0809(6) 0.0673(14) Uani 1 1 d . . . . .
H4A H 0.2057 0.0236 0.0798 0.081 Uiso 1 1 d R U . . .
H4B H 0.1098 0.1561 -0.0135 0.081 Uiso 1 1 d R U . . .
Cl1 Cl 0.17489(12) 0.61417(17) 0.4610(2) 0.0665(3) Uani 1 1 d . . . . .
F1 F -0.0146(5) -0.1487(4) 0.1689(6) 0.1044(15) Uani 1 1 d . . . . .
N1 N 0.0930(4) 0.4522(5) 0.1512(5) 0.0584(10) Uani 1 1 d . . . . .
H1A H 0.1512 0.5038 0.0890 0.088 Uiso 1 1 calc R U . . .
H1B H 0.0868 0.5251 0.2283 0.088 Uiso 1 1 calc R U . . .
H1C H 0.0104 0.4412 0.1109 0.088 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.471(6) . ?
C1 C4 1.522(7) . ?
C1 C2 1.528(8) . ?
C1 H1D 0.9800 . ?
C2 C3 1.468(18) . ?
C2 C3' 1.480(11) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C3 C3' 0.976(19) . ?
C3 F1 1.386(12) . ?
C3 C4 1.478(18) . ?
C3 H3A 0.9600 . ?
C3' F1 1.406(9) . ?
C3' C4 1.507(12) . ?
C3' H3'A 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9601 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?

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
N1 C1 C4 116.1(4) . . ?
N1 C1 C2 115.1(5) . . ?
C4 C1 C2 87.9(4) . . ?
N1 C1 H1D 111.9 . . ?
C4 C1 H1D 111.9 . . ?
C2 C1 H1D 111.9 . . ?
C3 C2 C3' 38.7(7) . . ?
C3 C2 C1 87.8(7) . . ?
C3' C2 C1 86.8(6) . . ?
C3 C2 H2A 113.4 . . ?
C3' C2 H2A 146.9 . . ?
C1 C2 H2A 114.1 . . ?
C3 C2 H2B 114.5 . . ?
C3' C2 H2B 79.7 . . ?
C1 C2 H2B 113.8 . . ?
H2A C2 H2B 111.4 . . ?
C3' C3 F1 70.7(9) . . ?
C3' C3 C2 71.3(13) . . ?
F1 C3 C2 119.8(13) . . ?
C3' C3 C4 72.5(12) . . ?
F1 C3 C4 118.2(11) . . ?
C2 C3 C4 91.8(9) . . ?
C3' C3 H3A 179.0 . . ?
F1 C3 H3A 108.7 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.5 . . ?
C3 C3' F1 68.4(9) . . ?
C3 C3' C2 70.0(11) . . ?
F1 C3' C2 117.6(8) . . ?
C3 C3' C4 69.3(12) . . ?
F1 C3' C4 115.0(8) . . ?
C2 C3' C4 90.2(5) . . ?
C3 C3' H3'A 179.0 . . ?
F1 C3' H3'A 110.9 . . ?
C2 C3' H3'A 111.0 . . ?
C4 C3' H3'A 110.6 . . ?
C3' C4 C3 38.2(7) . . ?
C3' C4 C1 86.1(5) . . ?
C3 C4 C1 87.7(7) . . ?
C3' C4 H4A 80.6 . . ?
C3 C4 H4A 114.7 . . ?
C1 C4 H4A 113.8 . . ?
C3' C4 H4B 147.1 . . ?
C3 C4 H4B 113.5 . . ?
C1 C4 H4B 114.0 . . ?
H4A C4 H4B 111.3 . . ?
C3 F1 C3' 40.9(8) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 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 C1 C2 C3 101.7(8) . . . . ?
C4 C1 C2 C3 -16.2(7) . . . . ?
N1 C1 C2 C3' 140.4(6) . . . . ?
C4 C1 C2 C3' 22.5(6) . . . . ?
C1 C2 C3 C3' 87.6(11) . . . . ?
C3' C2 C3 F1 53.4(11) . . . . ?
C1 C2 C3 F1 141.0(13) . . . . ?
C3' C2 C3 C4 -70.8(11) . . . . ?
C1 C2 C3 C4 16.7(7) . . . . ?
C2 C3 C3' F1 132.4(9) . . . . ?
C4 C3 C3' F1 -129.5(9) . . . . ?
F1 C3 C3' C2 -132.4(9) . . . . ?
C4 C3 C3' C2 98.1(6) . . . . ?
F1 C3 C3' C4 129.5(9) . . . . ?
C2 C3 C3' C4 -98.1(6) . . . . ?
C1 C2 C3' C3 -90.6(12) . . . . ?
C3 C2 C3' F1 -50.8(12) . . . . ?
C1 C2 C3' F1 -141.3(8) . . . . ?
C3 C2 C3' C4 67.9(12) . . . . ?
C1 C2 C3' C4 -22.7(5) . . . . ?
F1 C3' C4 C3 52.4(11) . . . . ?
C2 C3' C4 C3 -68.5(11) . . . . ?
C3 C3' C4 C1 91.3(11) . . . . ?
F1 C3' C4 C1 143.7(7) . . . . ?
C2 C3' C4 C1 22.8(6) . . . . ?
F1 C3 C4 C3' -55.8(11) . . . . ?
C2 C3 C4 C3' 69.8(12) . . . . ?
C3' C3 C4 C1 -86.6(10) . . . . ?
F1 C3 C4 C1 -142.3(13) . . . . ?
C2 C3 C4 C1 -16.8(7) . . . . ?
N1 C1 C4 C3' -139.1(5) . . . . ?
C2 C1 C4 C3' -22.1(5) . . . . ?
N1 C1 C4 C3 -100.9(8) . . . . ?
C2 C1 C4 C3 16.1(7) . . . . ?
C2 C3 F1 C3' -53.7(13) . . . . ?
C4 C3 F1 C3' 56.7(13) . . . . ?
C2 C3' F1 C3 51.5(13) . . . . ?
C4 C3' F1 C3 -52.9(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C Cl1 0.89 2.32 3.188(5) 166.5 2_564
N1 H1B F1 0.89 2.58 3.025(5) 111.9 1_565
N1 H1B Cl1 0.89 2.42 3.217(5) 148.9 .
N1 H1A Cl1 0.89 2.21 3.094(4) 169.7 4_554
C3 H3A Cl1 0.96 2.69 3.531(16) 147.1 2_564
C1 H1D F1 0.98 2.64 3.431(7) 138.1 3

_refine_diff_density_max         0.735
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.225



####################################################################### 
# 
# 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_P213
_database_code_depnum_ccdc_archive 'CCDC 1978971'
loop_
_audit_author_name
_audit_author_address
'Han-Yue zhanghanyue'
;Southeast University
China
;
_audit_update_record             
;
2021-12-10 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N, Cl'
_chemical_formula_sum            'C4 H10 Cl N'
_chemical_formula_weight         107.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           198
_space_group_name_H-M_alt        'P 21 3'
_space_group_name_Hall           'P 2ac 2ab 3'

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

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

_cell_length_a                   8.5648(3)
_cell_length_b                   8.5648(3)
_cell_length_c                   8.5648(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     628.28(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    343(2)
_cell_measurement_reflns_used    726
_cell_measurement_theta_min      3.3540
_cell_measurement_theta_max      25.2220

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.477
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      343(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1991
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.364
_diffrn_reflns_theta_max         31.325
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             700
_reflns_number_gt                309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_max     0.797
_reflns_Friedel_fraction_full    0.987

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 97 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.34(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         700
_refine_ls_number_parameters     20
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.3194
_refine_ls_wR_factor_gt          0.2794
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.011

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
C2 C 0.0162(6) 0.3458(8) 0.1061(9) 0.195(4) Uani 0.6667 1 d D . P . .
H2A H 0.0495 0.2568 0.0467 0.234 Uiso 0.6667 1 d R U P . .
H2B H 0.0862 0.3649 0.1916 0.234 Uiso 0.6667 1 d R U P . .
Cl1 Cl 0.40874(10) 0.59126(10) 0.09126(10) 0.1008(4) Uani 1 3 d S T P . .
C3 C -0.1564(5) 0.3436(5) 0.1564(5) 0.191(2) Uani 1 3 d DS T P . .
H3A H -0.1775 0.2984 0.2619 0.230 Uiso 0.3333 1 d R U P . .
H3B H -0.2291 0.3056 0.0819 0.230 Uiso 0.3333 1 d R U P . .
N1 N 0.0809(2) 0.5809(2) -0.0809(2) 0.0921(11) Uani 1 3 d DS T P . .
H1A H 0.0227 0.6582 -0.1240 0.138 Uiso 0.3333 1 d R U P . .
H1B H 0.1574 0.6240 -0.0234 0.138 Uiso 0.3333 1 d R U P . .
H1C H 0.1232 0.5234 -0.1582 0.138 Uiso 0.3333 1 d R U P . .
C1 C -0.0157(4) 0.4843(4) 0.0157(4) 0.191(2) Uani 1 3 d DS T P . .
H1D H -0.0916 0.4450 -0.0562 0.230 Uiso 0.3333 1 d R U P . .


_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
C2 C1 1.442(8) . ?
C2 C3 1.540(7) . ?
C2 C2 1.843(10) 8 ?
C2 C2 1.843(10) 11_455 ?
C3 C2 1.540(7) 8 ?
C3 C2 1.540(7) 11_455 ?
C3 C1 2.087(9) . ?
N1 C1 1.433(7) . ?
C1 C2 1.442(8) 11_455 ?
C1 C2 1.442(8) 8 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C3 88.7(4) . . ?
C1 C2 C2 50.3(2) . 8 ?
C3 C2 C2 53.2(2) . 8 ?
C1 C2 C2 50.3(2) . 11_455 ?
C3 C2 C2 53.2(2) . 11_455 ?
C2 C2 C2 60.0 8 11_455 ?
C2 C3 C2 73.5(5) . 8 ?
C2 C3 C2 73.5(5) . 11_455 ?
C2 C3 C2 73.5(5) 8 11_455 ?
C2 C3 C1 43.7(3) . . ?
C2 C3 C1 43.7(3) 8 . ?
C2 C3 C1 43.7(3) 11_455 . ?
N1 C1 C2 132.5(3) . 11_455 ?
N1 C1 C2 132.5(3) . 8 ?
C2 C1 C2 79.4(4) 11_455 8 ?
N1 C1 C2 132.5(3) . . ?
C2 C1 C2 79.4(4) 11_455 . ?
C2 C1 C2 79.4(4) 8 . ?
N1 C1 C3 180.0(2) . . ?
C2 C1 C3 47.5(3) 11_455 . ?
C2 C1 C3 47.5(3) 8 . ?
C2 C1 C3 47.5(3) . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_P212121
_database_code_depnum_ccdc_archive 'CCDC 1978972'
loop_
_audit_author_name
_audit_author_address
'Han-Yue zhanghanyue'
;Southeast University
China
;
_audit_update_record             
;
2021-12-10 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N, Cl'
_chemical_formula_sum            'C4 H10 Cl N'
_chemical_formula_weight         107.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

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

_cell_length_a                   7.8522(6)
_cell_length_b                   8.8201(6)
_cell_length_c                   8.9227(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     617.96(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2028
_cell_measurement_theta_min      3.2360
_cell_measurement_theta_max      27.2670

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.485
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4693
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.248
_diffrn_reflns_theta_max         31.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2066
_reflns_number_gt                1226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.604
_reflns_Friedel_fraction_max     0.740
_reflns_Friedel_fraction_full    0.984

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0871P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.18(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2066
_refine_ls_number_parameters     56
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6837(5) 0.7570(4) 0.2488(4) 0.0634(8) Uani 1 1 d . . . . .
H1 H 0.5771 0.8148 0.2493 0.076 Uiso 1 1 calc R U . . .
C2 C 0.7300(6) 0.7069(6) 0.4045(4) 0.0967(16) Uani 1 1 d . . . . .
H2A H 0.6855 0.7717 0.4831 0.116 Uiso 1 1 calc R U . . .
H2B H 0.8506 0.6876 0.4186 0.116 Uiso 1 1 calc R U . . .
C3 C 0.6232(6) 0.5629(5) 0.3762(4) 0.0871(13) Uani 1 1 d . . . . .
H3A H 0.6752 0.4702 0.4127 0.105 Uiso 1 1 calc R U . . .
H3B H 0.5054 0.5710 0.4080 0.105 Uiso 1 1 calc R U . . .
C4 C 0.6513(5) 0.5925(4) 0.2081(4) 0.0716(9) Uani 1 1 d . . . . .
H4A H 0.7494 0.5408 0.1663 0.086 Uiso 1 1 calc R U . . .
H4B H 0.5507 0.5768 0.1468 0.086 Uiso 1 1 calc R U . . .
Cl1 Cl 0.16486(12) 0.65410(10) 0.16764(9) 0.0655(3) Uani 1 1 d . . . . .
N1 N 0.8177(3) 0.8385(3) 0.1629(3) 0.0602(6) Uani 1 1 d . . . . .
H1A H 0.9115 0.7820 0.1592 0.090 Uiso 1 1 calc R U . . .
H1B H 0.8409 0.9262 0.2078 0.090 Uiso 1 1 calc R U . . .
H1C H 0.7808 0.8561 0.0702 0.090 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.487(4) . ?
C1 C2 1.503(5) . ?
C1 C4 1.517(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.542(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.538(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?

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
N1 C1 C2 116.6(3) . . ?
N1 C1 C4 117.2(3) . . ?
C2 C1 C4 88.9(3) . . ?
N1 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
C4 C1 H1 110.8 . . ?
C1 C2 C3 87.7(3) . . ?
C1 C2 H2A 114.0 . . ?
C3 C2 H2A 114.0 . . ?
C1 C2 H2B 114.0 . . ?
C3 C2 H2B 114.0 . . ?
H2A C2 H2B 111.2 . . ?
C4 C3 C2 86.7(3) . . ?
C4 C3 H3A 114.2 . . ?
C2 C3 H3A 114.2 . . ?
C4 C3 H3B 114.2 . . ?
C2 C3 H3B 114.2 . . ?
H3A C3 H3B 111.4 . . ?
C1 C4 C3 87.3(3) . . ?
C1 C4 H4A 114.1 . . ?
C3 C4 H4A 114.1 . . ?
C1 C4 H4B 114.1 . . ?
C3 C4 H4B 114.1 . . ?
H4A C4 H4B 111.3 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 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 C1 C2 C3 -143.3(3) . . . . ?
C4 C1 C2 C3 -23.2(4) . . . . ?
C1 C2 C3 C4 22.9(3) . . . . ?
N1 C1 C4 C3 142.8(3) . . . . ?
C2 C1 C4 C3 23.2(4) . . . . ?
C2 C3 C4 C1 -22.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.89 2.29 3.175(3) 174.0 1_655
N1 H1B Cl1 0.89 2.30 3.171(3) 166.9 3_655
N1 H1C Cl1 0.89 2.31 3.184(3) 167.1 4_565

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.060



