# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1572147'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2017-12-14 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 H11 Br N, Cl O4'
_chemical_formula_sum            'C4 H11 Br Cl N O4'
_chemical_formula_weight         252.49

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   6.1256(12)
_cell_length_b                   7.9158(16)
_cell_length_c                   9.5663(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.29(3)
_cell_angle_gamma                90
_cell_volume                     451.44(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1104
_cell_measurement_theta_min      3.001
_cell_measurement_theta_max      27.483

_exptl_crystal_description       'Thick sheet'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   0.749
_exptl_transmission_factor_max   0.886
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    4.820
_shelx_estimated_absorpt_T_min   0.330
_shelx_estimated_absorpt_T_max   0.624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.216
_exptl_absorpt_correction_T_max  0.381
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4679
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.378
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1104
_reflns_number_gt                979
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_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)+(0.0273P)²+0.4959P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1104
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57264(9) 0.2500 -0.00519(5) 0.0552(2) Uani 1 2 d S T P . .
Cl1 Cl 0.94391(14) 0.2500 0.73631(9) 0.0325(2) Uani 1 2 d S T P . .
O1 O 1.0826(6) 0.2500 0.6357(4) 0.0691(10) Uani 1 2 d S T P . .
O2 O 0.7121(5) 0.2500 0.6607(4) 0.0599(9) Uani 1 2 d S T P . .
O3 O 0.9866(4) 0.3969(3) 0.8252(3) 0.0578(6) Uani 1 1 d . . . . .
C1 C 0.3626(6) 0.2500 0.1145(4) 0.0389(8) Uani 1 2 d S T P . .
H1A H 0.2675 0.3490 0.0928 0.047 Uiso 0.5 1 calc R U P . .
H1B H 0.2675 0.1510 0.0928 0.047 Uiso 0.5 1 calc R U P . .
C2 C 0.2901(7) 0.2500 0.3522(4) 0.0412(9) Uani 1 2 d S T P . .
H2A H 0.3545 0.2500 0.4534 0.049 Uiso 1 2 d R U P . .
H2B H 0.2047 0.1476 0.3317 0.049 Uiso 1 1 d R U . . .
C3 C 0.6142(5) 0.0949(3) 0.3123(3) 0.0394(6) Uani 1 1 d . . . . .
H3A H 0.7329 0.0938 0.2620 0.059 Uiso 1 1 calc R U . . .
H3B H 0.5222 -0.0036 0.2869 0.059 Uiso 1 1 calc R U . . .
H3C H 0.6771 0.0951 0.4139 0.059 Uiso 1 1 calc R U . . .
N1 N 0.4743(5) 0.2500 0.2719(3) 0.0278(6) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0786(4) 0.0552(3) 0.0403(3) 0.000 0.0310(2) 0.000
Cl1 0.0337(4) 0.0302(4) 0.0346(4) 0.000 0.0100(3) 0.000
O1 0.070(2) 0.087(3) 0.064(2) 0.000 0.0433(19) 0.000
O2 0.0411(16) 0.077(2) 0.0548(19) 0.000 -0.0028(14) 0.000
O3 0.0693(14) 0.0388(12) 0.0638(14) -0.0155(10) 0.0123(11) -0.0052(10)
C1 0.040(2) 0.043(2) 0.0318(18) 0.000 0.0056(15) 0.000
C2 0.042(2) 0.042(2) 0.045(2) 0.000 0.0209(17) 0.000
C3 0.0472(15) 0.0287(13) 0.0419(14) 0.0037(11) 0.0093(12) 0.0093(11)
N1 0.0323(14) 0.0238(14) 0.0287(14) 0.000 0.0101(11) 0.000

_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 1.909(4) . ?
Cl1 O1 1.423(3) . ?
Cl1 O3 1.429(2) . ?
Cl1 O3 1.429(2) 4_565 ?
Cl1 O2 1.438(3) . ?
C1 N1 1.504(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.504(4) . ?
C2 H2A 0.9583 . ?
C2 H2B 0.9600 . ?
C3 N1 1.496(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
N1 C3 1.496(3) 4_565 ?

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
O1 Cl1 O3 110.30(13) . . ?
O1 Cl1 O3 110.30(13) . 4_565 ?
O3 Cl1 O3 108.9(2) . 4_565 ?
O1 Cl1 O2 109.5(2) . . ?
O3 Cl1 O2 108.89(13) . . ?
O3 Cl1 O2 108.89(13) 4_565 . ?
N1 C1 Br1 112.7(2) . . ?
N1 C1 H1A 109.0 . . ?
Br1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
Br1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 106.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C3 N1 C3 110.3(3) 4_565 . ?
C3 N1 C2 108.69(18) 4_565 . ?
C3 N1 C2 108.70(18) . . ?
C3 N1 C1 111.12(18) 4_565 . ?
C3 N1 C1 111.12(18) . . ?
C2 N1 C1 106.8(3) . . ?

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 N1 C3 61.61(18) . . . 4_565 ?
Br1 C1 N1 C3 -61.61(18) . . . . ?
Br1 C1 N1 C2 180.000(0) . . . . ?

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
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646
C3 H3A O3 0.96 2.60 3.413(4) 143.2 2_746
C3 H3B O2 0.96 2.54 3.428(4) 154.1 3_656
C3 H3C O2 0.96 2.62 3.472(4) 147.4 .
C2 H2A O2 0.96 2.59 3.448(5) 148.4 .
C2 H2B O3 0.96 2.60 3.499(4) 156.1 2_646

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.076

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL 1 in P2(1)                  New: P21/m
CELL  0.71073    6.1256    7.9158    9.5663    90.000   103.290    90.000
ZERR  2           0.0012    0.0016    0.0019     0.000     0.030     0.000
LATT 1
SYMM             - X ,    0.50000 + Y ,            - Z
SFAC C  H  Br Cl N  O
UNIT 8 22 2 2 2 8
L.S. 20
ACTA
BOND $H
FMAP 2
PLAN 3
HTAB C2 O3_$3
HTAB C2 O2
HTAB C3 O2
HTAB C3 O2_$2
HTAB C3 O3_$1
HTAB C2 O3_$3
HTAB C2 O2
HTAB C3 O2
HTAB C3 O2_$2
HTAB C3 O3_$1
HTAB C2 O3_$3
HTAB C2 O2
HTAB C3 O2
HTAB C3 O2_$2
HTAB C3 O3_$1
HTAB C2 O3_$3
HTAB C2 O2
HTAB C3 O2
HTAB C3 O2_$2
HTAB C3 O3_$1
HTAB C2 O3_$3
EQIV $3 -x+1, y-1/2, -z+1
HTAB C2 O2
HTAB C3 O2
HTAB C3 O2_$2
EQIV $2 -x+1, -y, -z+1
HTAB C3 O3_$1
EQIV $1 -x+2, y-1/2, -z+1
CONF
HTAB
HTAB C3 O3_$1
HTAB C3 O2_$2
HTAB C3 O2
HTAB C2 O2
HTAB C2 O3_$3
HTAB C3 O3_$1
HTAB C3 O2_$2
HTAB C3 O2
HTAB C2 O2
HTAB C2 O3_$3
HTAB C3 O3_$1
HTAB C3 O2_$2
HTAB C3 O2
HTAB C2 O2
HTAB C2 O3_$3
HTAB C3 O3_$1
HTAB C3 O2_$2
HTAB C3 O2
HTAB C2 O2
HTAB C2 O3_$3
HTAB C3 O3_$1
HTAB C3 O2_$2
HTAB C3 O2
HTAB C2 O2
HTAB C2 O3_$3
HTAB C3 O3_$1
HTAB C3 O2_$2
HTAB C3 O2
HTAB C2 O2
HTAB C2 O3_$3
WGHT    0.027300    0.495900
EXTI    0.037736
FVAR       0.39184
BR1   3    0.572642    0.250000   -0.005191    10.50000    0.07860    0.05520 =
         0.04029    0.00000    0.03105    0.00000
CL1   4    0.943909    0.250000    0.736305    10.50000    0.03374    0.03019 =
         0.03459    0.00000    0.00997    0.00000
O1    6    1.082581    0.250000    0.635663    10.50000    0.07021    0.08670 =
         0.06401    0.00000    0.04331    0.00000
O2    6    0.712135    0.250000    0.660701    10.50000    0.04107    0.07716 =
         0.05484    0.00000   -0.00285    0.00000
O3    6    0.986560    0.396882    0.825218    11.00000    0.06927    0.03883 =
         0.06382   -0.01553    0.01232   -0.00518
C1    1    0.362577    0.250000    0.114462    10.50000    0.04005    0.04338 =
         0.03182    0.00000    0.00558    0.00000
AFIX  23
H1A   2    0.267515    0.349020    0.092818    10.50000   -1.20000
H1B   2    0.267515    0.150980    0.092818    10.50000   -1.20000
AFIX   0
C2    1    0.290053    0.250000    0.352184    10.50000    0.04194    0.04218 =
         0.04491    0.00000    0.02091    0.00000
AFIX   3
H2A   2    0.354493    0.250000    0.453444    10.50000   -1.20000
H2B   2    0.204653    0.147630    0.331734    11.00000   -1.20000
AFIX   0
C3    1    0.614166    0.094935    0.312304    11.00000    0.04721    0.02873 =
         0.04190    0.00368    0.00927    0.00931
AFIX 137
H3A   2    0.732934    0.093778    0.262025    11.00000   -1.50000
H3B   2    0.522210   -0.003579    0.286866    11.00000   -1.50000
H3C   2    0.677095    0.095087    0.413939    11.00000   -1.50000
AFIX   0
N1    5    0.474339    0.250000    0.271919    10.50000    0.03233    0.02376 =
         0.02875    0.00000    0.01010    0.00000
HKLF 4

REM  1 in P2(1)                  New: P21/m
REM R1 =  0.0314 for     979 Fo > 4sig(Fo)  and  0.0370 for all    1104 data
REM     63 parameters refined using      0 restraints

END

WGHT      0.0274      0.2937

REM Instructions for potential hydrogen bonds
HTAB C2 O2
HTAB C2 O3_$3
HTAB C3 O3_$1
HTAB C3 O2_$2
HTAB C3 O2

REM Highest difference peak  0.450,  deepest hole -0.476,  1-sigma level  0.076
Q1    1   0.6580  0.1733  0.0212  11.00000  0.05    0.45
Q2    1   0.5437  0.2500 -0.0387  10.50000  0.05    0.34
Q3    1   1.0059  0.1609  0.6151  11.00000  0.05    0.32
;
_shelx_res_checksum              97551
####################################################################### 
# 
# 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_P21M
_database_code_depnum_ccdc_archive 'CCDC 1572176'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2017-12-14 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         'Cl O4, C4 H11 Br N'
_chemical_formula_sum            'C4 H11 Br Cl N O4'
_chemical_formula_weight         252.50

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   6.250(12)
_cell_length_b                   8.164(16)
_cell_length_c                   9.64(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.49(4)
_cell_angle_gamma                90
_cell_volume                     482.0(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    363(2)
_cell_measurement_reflns_used    1169
_cell_measurement_theta_min      1.6988
_cell_measurement_theta_max      27.348

_exptl_crystal_description       'Thick sheet'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.515
_shelx_estimated_absorpt_T_min   0.279
_shelx_estimated_absorpt_T_max   0.465
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.239
_exptl_absorpt_correction_T_max  0.405
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      363(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3359
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.299
_diffrn_reflns_theta_max         27.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             1169
_reflns_number_gt                619
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2008)'
_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+13.8000P] 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_number_reflns         1133
_refine_ls_number_parameters     64
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.2346
_refine_ls_R_factor_gt           0.1910
_refine_ls_wR_factor_ref         0.4877
_refine_ls_wR_factor_gt          0.4587
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.5751(8) 0.2500 -0.0038(4) 0.111(2) Uani 1 2 d S T P . .
Cl1 Cl 0.9498(10) 0.2500 0.7267(6) 0.0614(16) Uani 1 2 d DS TU P . .
O1 O 1.100(3) 0.2500 0.635(2) 0.109(6) Uani 1 2 d DS TU P . .
O2 O 0.7240(17) 0.2500 0.666(2) 0.095(5) Uani 1 2 d DS TU P . .
O3 O 1.002(4) 0.120(3) 0.830(2) 0.086(5) Uani 0.5 1 d D U P . .
O3' O 0.944(6) 0.094(2) 0.796(3) 0.086(5) Uani 0.5 1 d D U P . .
C1 C 0.356(6) 0.2500 0.120(3) 0.078(8) Uani 1 2 d S T P . .
H1A H 0.2648 0.1550 0.0985 0.094 Uiso 0.5 1 d R U P . .
H1B H 0.2648 0.3450 0.0985 0.094 Uiso 0.5 1 d R U P . .
C2 C 0.274(5) 0.2500 0.359(3) 0.079(8) Uani 1 2 d S T P . .
H2A H 0.1838 0.3460 0.3399 0.119 Uiso 0.5 1 d R U P . .
H2B H 0.1840 0.1539 0.3400 0.119 Uiso 0.5 1 d R U P . .
H2C H 0.3462 0.2500 0.4569 0.119 Uiso 1 2 d R U P . .
C3 C 0.592(3) 0.093(2) 0.302(2) 0.068(5) Uani 1 1 d . . . . .
H3A H 0.6994 0.0913 0.2435 0.103 Uiso 1 1 d R U . . .
H3B H 0.6632 0.0937 0.3999 0.103 Uiso 1 1 d R U . . .
H3C H 0.5010 -0.0024 0.2830 0.103 Uiso 1 1 d R U . . .
N1 N 0.464(3) 0.2500 0.2680(17) 0.044(4) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.163(4) 0.109(3) 0.078(2) 0.000 0.064(2) 0.000
Cl1 0.064(3) 0.052(3) 0.064(3) 0.000 0.004(2) 0.000
O1 0.113(11) 0.115(13) 0.105(12) 0.000 0.038(9) 0.000
O2 0.079(8) 0.107(12) 0.089(11) 0.000 -0.011(8) 0.000
O3 0.096(10) 0.057(7) 0.093(9) 0.005(7) -0.011(7) -0.011(7)
O3' 0.096(10) 0.057(7) 0.093(9) 0.005(7) -0.011(7) -0.011(7)
C1 0.11(2) 0.070(16) 0.050(13) 0.000 0.013(13) 0.000
C2 0.12(3) 0.054(14) 0.071(16) 0.000 0.028(16) 0.000
C3 0.062(10) 0.052(9) 0.090(12) 0.002(8) 0.010(8) 0.027(8)
N1 0.056(10) 0.034(7) 0.050(8) 0.000 0.027(7) 0.000

_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 1.99(3) . ?
Cl1 O1 1.413(9) . ?
Cl1 O2 1.417(9) . ?
Cl1 O3' 1.445(10) 4_565 ?
Cl1 O3' 1.445(10) . ?
Cl1 O3 1.447(9) 4_565 ?
Cl1 O3 1.447(9) . ?
C1 N1 1.45(3) . ?
C2 N1 1.61(3) . ?
C3 N1 1.512(17) . ?
N1 C3 1.512(17) 4_565 ?

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
O1 Cl1 O2 118.1(11) . . ?
O1 Cl1 O3' 111.8(18) . 4_565 ?
O2 Cl1 O3' 94.5(14) . 4_565 ?
O1 Cl1 O3' 111.8(18) . . ?
O2 Cl1 O3' 94.5(14) . . ?
O3' Cl1 O3' 124(3) 4_565 . ?
O1 Cl1 O3 110.3(12) . 4_565 ?
O2 Cl1 O3 110.8(10) . 4_565 ?
O3' Cl1 O3 19.4(16) 4_565 4_565 ?
O3' Cl1 O3 110.3(15) . 4_565 ?
O1 Cl1 O3 110.3(12) . . ?
O2 Cl1 O3 110.8(10) . . ?
O3' Cl1 O3 110.3(15) 4_565 . ?
O3' Cl1 O3 19.4(16) . . ?
O3 Cl1 O3 94(2) 4_565 . ?
N1 C1 Br1 111(2) . . ?
C1 N1 C3 109.5(11) . 4_565 ?
C1 N1 C3 109.5(11) . . ?
C3 N1 C3 115.9(19) 4_565 . ?
C1 N1 C2 107(2) . . ?
C3 N1 C2 107.3(11) 4_565 . ?
C3 N1 C2 107.3(11) . . ?

_refine_diff_density_max         3.370
_refine_diff_density_min         -1.278
_refine_diff_density_rms         0.342

# start Validation Reply Form

_vrf_PLAT082_P21M                
;
PROBLEM: High R1 Value .................................. 0.19 Report

RESPONSE: The quality of crystal was effected by high temperature. 
          Besides, the CLO4 anions were disordered.
;
_vrf_PLAT084_P21M                
;
PROBLEM:High wR2 Value (i.e. > 0.25) ................... 0.49 Report

RESPONSE: The quality of crystal was effected by high temperature. 
          Besides, the CLO4 anions were disordered.
;

# end Validation Reply Form

_shelx_res_file                  
;

    P21M.res created by SHELXL-2014/7


TITL P21M in P2(1)/m
CELL 0.71073   6.2502   8.1641   9.6360  90.000 101.492  90.000
ZERR    2.00   0.0121   0.0165   0.0202   0.000   0.037   0.000
LATT 1
SYMM -X, 0.5+Y, -Z
SFAC C  H  N  O  Cl Br
UNIT 8 22 2 8 2 2
L.S. 40
ACTA
BOND
FMAP 2
PLAN 4
SIZE 0.38 0.28 0.20
EADP O3 O3'
DFIX 2.35 0.02 O1 O2 O1 O3 O2 O3
DFIX 1.44 0.01 CL1 O2 CL1 O1 CL1 O3 CL1 O3'
DELU 0.01 CL1 O1 O2 O3 O3'
SIMU 0.01 CL1 O1 O2 O3 O3'
SIZE 0.38 0.28 0.20
TEMP 90
WGHT    0.200000   13.800000
FVAR       0.76392
BR1   6    0.575087    0.250000   -0.003831    10.50000    0.16345    0.10876 =
         0.07751    0.00000    0.06370    0.00000
CL1   5    0.949794    0.250000    0.726678    10.50000    0.06443    0.05210 =
         0.06399    0.00000    0.00359    0.00000
O1    4    1.100011    0.250000    0.634866    10.50000    0.11323    0.11512 =
         0.10526    0.00000    0.03825    0.00000
O2    4    0.724018    0.250000    0.665638    10.50000    0.07896    0.10714 =
         0.08860    0.00000   -0.01110    0.00000
O3    4    1.001744    0.120473    0.830433    10.50000    0.09565    0.05654 =
         0.09287    0.00535   -0.01060   -0.01129
O3'   4    0.944259    0.093710    0.796222    10.50000    0.09565    0.05654 =
         0.09287    0.00535   -0.01060   -0.01129
C1    1    0.356046    0.250000    0.119788    10.50000    0.11327    0.06973 =
         0.05034    0.00000    0.01272    0.00000
AFIX   3
H1A   2    0.264786    0.155050    0.098528    10.50000   -1.20000
H1B   2    0.264786    0.344950    0.098528    10.50000   -1.20000
AFIX   0
C2    1    0.273592    0.250000    0.359206    10.50000    0.11736    0.05360 =
         0.07129    0.00000    0.02805    0.00000
AFIX   3
H2A   2    0.183822    0.345960    0.339895    10.50000   -1.50000
H2B   2    0.183982    0.153940    0.340006    10.50000   -1.50000
H2C   2    0.346232    0.250000    0.456866    10.50000   -1.50000
AFIX   0
C3    1    0.591733    0.093060    0.301976    11.00000    0.06204    0.05151 =
         0.08968    0.00159    0.01023    0.02670
AFIX   3
H3A   2    0.699422    0.091340    0.243516    11.00000   -1.50000
H3B   2    0.663203    0.093730    0.399876    11.00000   -1.50000
H3C   2    0.500951   -0.002420    0.283016    11.00000   -1.50000
AFIX   0
N1    3    0.463634    0.250000    0.268036    10.50000    0.05611    0.03402 =
         0.04985    0.00000    0.02657    0.00000

HKLF 4

REM  P21M in P2(1)/m
REM R1 =  0.1910 for     619 Fo > 4sig(Fo)  and  0.2346 for all    1133 data
REM     64 parameters refined using     47 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  3.370,  deepest hole -1.278,  1-sigma level  0.342
Q1    1   0.7425  0.1647  0.0757  11.00000  0.05    3.37
Q2    1   0.9400  0.2500  0.6894  10.50000  0.05    1.37
Q3    1   1.2441  0.2500  0.7174  10.50000  0.05    1.14
Q4    1   0.5159  0.2500  0.2437  10.50000  0.05    1.08
;
_shelx_res_checksum              3868
####################################################################### 
# 
# 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_P21M_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1572185'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2017-12-14 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 H11 Br N, B F4'
_chemical_formula_sum            'C4 H11 B Br F4 N'
_chemical_formula_weight         239.85

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   6.0331(12)
_cell_length_b                   7.8583(16)
_cell_length_c                   9.5127(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.67(3)
_cell_angle_gamma                90
_cell_volume                     438.22(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1073
_cell_measurement_theta_min      1.6988
_cell_measurement_theta_max      27.483

_exptl_crystal_description       Sheet
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.694
_shelx_estimated_absorpt_T_min   0.228
_shelx_estimated_absorpt_T_max   0.399
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.225
_exptl_absorpt_correction_T_max  0.391
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4265
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.403
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1073
_reflns_number_gt                897
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2008)'
_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)+(0.0273P)²+0.4959P] 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_number_reflns         1070
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57871(11) 0.2500 -0.00559(6) 0.0642(3) Uani 1 2 d S T P . .
F1 F 1.0766(7) 0.2500 0.6358(4) 0.0894(12) Uani 1 2 d S T P . .
F2 F 0.7121(6) 0.2500 0.6588(4) 0.0723(10) Uani 1 2 d S T P . .
F3 F 0.9799(4) 0.3926(3) 0.8196(3) 0.0733(7) Uani 1 1 d . . . . .
B1 B 0.9408(9) 0.2500 0.7328(6) 0.0424(12) Uani 1 2 d S T P . .
C1 C 0.3609(9) 0.2500 0.1125(5) 0.0489(11) Uani 1 2 d S T P . .
H1A H 0.2644 0.3498 0.0899 0.059 Uiso 0.5 1 calc R U P . .
H1B H 0.2644 0.1502 0.0899 0.059 Uiso 0.5 1 calc R U P . .
C2 C 0.2837(9) 0.2500 0.3486(6) 0.0528(13) Uani 1 2 d S T P . .
H2A H 0.3481 0.2500 0.4499 0.063 Uiso 1 2 d R U P . .
H2B H 0.1983 0.1476 0.3282 0.063 Uiso 1 1 d R U . . .
C3 C 0.6149(6) 0.0937(4) 0.3133(4) 0.0476(8) Uani 1 1 d . . . . .
H3A H 0.7379 0.0930 0.2652 0.071 Uiso 1 1 calc R U . . .
H3B H 0.5215 -0.0052 0.2856 0.071 Uiso 1 1 calc R U . . .
H3C H 0.6757 0.0929 0.4161 0.071 Uiso 1 1 calc R U . . .
N1 N 0.4741(6) 0.2500 0.2715(4) 0.0350(8) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0951(5) 0.0591(4) 0.0464(3) 0.000 0.0327(3) 0.000
F1 0.092(3) 0.111(3) 0.081(3) 0.000 0.052(2) 0.000
F2 0.055(2) 0.088(3) 0.065(2) 0.000 -0.0023(16) 0.000
F3 0.0851(17) 0.0529(13) 0.0793(17) -0.0170(12) 0.0145(14) -0.0093(12)
B1 0.044(3) 0.041(3) 0.042(3) 0.000 0.010(2) 0.000
C1 0.053(3) 0.054(3) 0.037(2) 0.000 0.004(2) 0.000
C2 0.053(3) 0.053(3) 0.059(3) 0.000 0.025(3) 0.000
C3 0.056(2) 0.0377(17) 0.0479(19) 0.0055(14) 0.0102(16) 0.0110(15)
N1 0.041(2) 0.0304(17) 0.0340(18) 0.000 0.0091(15) 0.000

_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 1.920(5) . ?
F1 B1 1.371(6) . ?
F2 B1 1.393(7) . ?
F3 B1 1.379(4) . ?
B1 F3 1.379(4) 4_565 ?
C1 N1 1.505(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.502(6) . ?
C2 H2A 0.9497 . ?
C2 H2B 0.9503 . ?
C3 N1 1.493(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
N1 C3 1.493(4) 4_565 ?

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 B1 F3 111.0(3) . . ?
F1 B1 F3 111.0(3) . 4_565 ?
F3 B1 F3 108.7(4) . 4_565 ?
F1 B1 F2 109.7(5) . . ?
F3 B1 F2 108.2(3) . . ?
F3 B1 F2 108.2(3) 4_565 . ?
N1 C1 Br1 112.2(3) . . ?
N1 C1 H1A 109.2 . . ?
Br1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
Br1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 H2A 108.6 . . ?
N1 C2 H2B 109.9 . . ?
H2A C2 H2B 106.2 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C3 N1 C3 110.7(4) . 4_565 ?
C3 N1 C2 108.8(2) . . ?
C3 N1 C2 108.8(2) 4_565 . ?
C3 N1 C1 111.2(2) . . ?
C3 N1 C1 111.2(2) 4_565 . ?
C2 N1 C1 105.9(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
Br1 C1 N1 C3 -62.0(2) . . . . ?
Br1 C1 N1 C3 62.0(2) . . . 4_565 ?
Br1 C1 N1 C2 180.000(1) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.091

_shelx_res_file                  
;

    P21M.res created by SHELXL-2014/7


TITL P21M in P2(1)/m             New: P21/m
CELL  0.71073    6.0331    7.8583    9.5127    90.000   103.670    90.000
ZERR  2           0.0012    0.0016    0.0019     0.000     0.030     0.000
LATT 1
SYMM             - X ,    0.50000 + Y ,            - Z
SFAC C  H  B Br F N
UNIT 8 22 2 2 8 2
L.S. 50
ACTA
BOND $H
FMAP 2
PLAN 3
CONF
WGHT    0.027300    0.495900
FVAR       0.80857
BR1   4    0.578707    0.250000   -0.005585    10.50000    0.09511    0.05908 =
         0.04639    0.00000    0.03273    0.00000
F1    5    1.076587    0.250000    0.635791    10.50000    0.09166    0.11134 =
         0.08097    0.00000    0.05182    0.00000
F2    5    0.712117    0.250000    0.658755    10.50000    0.05521    0.08792 =
         0.06550    0.00000   -0.00228    0.00000
F3    5    0.979941    0.392615    0.819623    11.00000    0.08515    0.05294 =
         0.07929   -0.01696    0.01453   -0.00933
B1    3    0.940776    0.250000    0.732827    10.50000    0.04401    0.04079 =
         0.04243    0.00000    0.01031    0.00000
C1    1    0.360930    0.250000    0.112515    10.50000    0.05255    0.05411 =
         0.03690    0.00000    0.00411    0.00000
AFIX  23
H1A   2    0.264427    0.349789    0.089945    10.50000   -1.20000
H1B   2    0.264427    0.150211    0.089945    10.50000   -1.20000
AFIX   0
C2    1    0.283696    0.250000    0.348632    10.50000    0.05273    0.05255 =
         0.05921    0.00000    0.02532    0.00000
AFIX   3
H2A   2    0.348136    0.250000    0.449892    10.50000   -1.20000
H2B   2    0.198296    0.147630    0.328182    11.00000   -1.20000
AFIX   0
C3    1    0.614858    0.093725    0.313319    11.00000    0.05619    0.03769 =
         0.04789    0.00545    0.01020    0.01102
AFIX 137
H3A   2    0.737917    0.092969    0.265183    11.00000   -1.50000
H3B   2    0.521498   -0.005248    0.285550    11.00000   -1.50000
H3C   2    0.675692    0.092944    0.416131    11.00000   -1.50000
AFIX   0
N1    6    0.474091    0.250000    0.271482    10.50000    0.04089    0.03040 =
         0.03396    0.00000    0.00908    0.00000
HKLF 4

REM  P21M in P2(1)/m             New: P21/m
REM R1 =  0.0450 for     897 Fo > 4sig(Fo)  and  0.0560 for all    1070 data
REM     62 parameters refined using      0 restraints

END

WGHT      0.0517      0.1533

REM Highest difference peak  0.362,  deepest hole -0.324,  1-sigma level  0.091
Q1    1   0.4347  0.2500  0.0499  10.50000  0.05    0.36
Q2    1   1.0102  0.1488  0.6130  11.00000  0.05    0.33
Q3    1   0.7299  0.2500  0.0860  10.50000  0.05    0.29
;
_shelx_res_checksum              35099
####################################################################### 
# 
# 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_P21M_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1572191'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2017-12-14 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         'B F4, C4 H11 Br N'
_chemical_formula_sum            'C4 H11 B Br F4 N'
_chemical_formula_weight         239.85

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'
B B 0.0013 0.0007 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   6.149(18)
_cell_length_b                   8.012(2)
_cell_length_c                   9.507(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.19(2)
_cell_angle_gamma                90
_cell_volume                     459.5(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    368(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      1.6988
_cell_measurement_theta_max      25.234

_exptl_crystal_description       Sheet
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.472
_shelx_estimated_absorpt_T_min   0.281
_shelx_estimated_absorpt_T_max   0.468
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.243
_exptl_absorpt_correction_T_max  0.409
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      368(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2870
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         25.234
_diffrn_reflns_theta_full        25.234
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             900
_reflns_number_gt                557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2008)'
_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+27.0000P] 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_number_reflns         898
_refine_ls_number_parameters     68
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.3247
_refine_ls_R_factor_gt           0.2759
_refine_ls_wR_factor_ref         0.5892
_refine_ls_wR_factor_gt          0.5531
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.5949(14) 0.2500 0.0027(7) 0.141(4) Uani 1 2 d DS T P . .
F3 F 1.011(5) 0.115(6) 0.799(5) 0.144(7) Uani 0.5 1 d D U P . .
F2 F 0.713(4) 0.2500 0.681(5) 0.144(7) Uani 0.5 2 d DS TU P . .
F1 F 1.027(9) 0.2500 0.597(4) 0.144(7) Uani 0.5 2 d DS TU P . .
F3' F 0.947(5) 0.118(6) 0.810(5) 0.144(7) Uani 0.5 1 d D U P . .
F2' F 0.743(6) 0.2500 0.623(5) 0.144(7) Uani 0.5 2 d DS TU P . .
F1' F 1.115(7) 0.2500 0.653(5) 0.144(7) Uani 0.5 2 d DS TU P . .
B1 B 0.938(4) 0.2500 0.717(3) 0.144(7) Uani 1 2 d DS TU P . .
C1 C 0.365(4) 0.2500 0.115(2) 0.059(6) Uani 1 2 d DS TU P . .
H1A H 0.2729 0.1532 0.0930 0.070 Uiso 0.5 1 d R U P . .
H1B H 0.2729 0.3468 0.0930 0.070 Uiso 0.5 1 d R U P . .
C3 C 0.611(3) 0.101(3) 0.313(3) 0.063(6) Uani 1 1 d D U . . .
H3A H 0.6802 0.0927 0.4121 0.095 Uiso 1 1 d R U . . .
H3B H 0.5207 0.0041 0.2855 0.095 Uiso 1 1 d R U . . .
H3C H 0.7226 0.1081 0.2553 0.095 Uiso 1 1 d R U . . .
C2 C 0.310(5) 0.2500 0.373(3) 0.057(6) Uani 1 2 d DS TU P . .
H2A H 0.2199 0.3486 0.3578 0.086 Uiso 0.5 1 d R U P . .
H2B H 0.2171 0.1530 0.3559 0.086 Uiso 0.5 1 d R U P . .
H2C H 0.3906 0.2500 0.4704 0.086 Uiso 1 2 d R U P . .
N1 N 0.465(3) 0.2500 0.271(2) 0.052(5) Uani 1 2 d DS TU P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.220(8) 0.118(5) 0.114(5) 0.000 0.105(5) 0.000
F3 0.157(13) 0.148(13) 0.136(13) 0.0003(19) 0.051(11) 0.000(2)
F2 0.157(13) 0.148(13) 0.136(13) 0.000 0.051(11) 0.000
F1 0.157(13) 0.149(13) 0.136(13) 0.000 0.051(11) 0.000
F3' 0.157(13) 0.148(13) 0.136(13) 0.0003(19) 0.051(11) 0.000(2)
F2' 0.157(13) 0.148(13) 0.136(13) 0.000 0.051(11) 0.000
F1' 0.157(13) 0.149(13) 0.136(13) 0.000 0.051(11) 0.000
B1 0.157(13) 0.149(13) 0.136(13) 0.000 0.051(11) 0.000
C1 0.048(11) 0.055(12) 0.064(11) 0.000 -0.011(9) 0.000
C3 0.042(9) 0.060(12) 0.081(13) 0.011(10) -0.007(9) 0.007(8)
C2 0.043(12) 0.057(15) 0.066(13) 0.000 -0.006(10) 0.000
N1 0.038(9) 0.049(10) 0.061(10) 0.000 -0.010(7) 0.000

_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 1.926(18) . ?
F3 B1 1.362(18) . ?
F2 F2' 0.62(6) . ?
F2 B1 1.359(19) . ?
F1 F1' 0.68(7) . ?
F1 B1 1.361(19) . ?
F3' B1 1.370(17) . ?
F2' B1 1.346(19) . ?
F1' B1 1.345(19) . ?
B1 F3 1.362(18) 4_565 ?
B1 F3' 1.370(17) 4_565 ?
C1 N1 1.491(19) . ?
C3 N1 1.501(16) . ?
C2 N1 1.487(19) . ?
N1 C3 1.501(17) 4_565 ?

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
F2' F2 B1 76(3) . . ?
F1' F1 B1 74(3) . . ?
F2 F2' B1 78(2) . . ?
F1 F1' B1 77(3) . . ?
F1' B1 F2' 113(2) . . ?
F1' B1 F2 140(3) . . ?
F2' B1 F2 26(2) . . ?
F1' B1 F1 29(3) . . ?
F2' B1 F1 84(3) . . ?
F2 B1 F1 110.3(19) . . ?
F1' B1 F3 93(2) . 4_565 ?
F2' B1 F3 122(2) . 4_565 ?
F2 B1 F3 110.6(18) . 4_565 ?
F1 B1 F3 109.8(18) . 4_565 ?
F1' B1 F3 93(2) . . ?
F2' B1 F3 122(3) . . ?
F2 B1 F3 110.6(18) . . ?
F1 B1 F3 109.8(17) . . ?
F3 B1 F3 105(5) 4_565 . ?
F1' B1 F3' 110.7(16) . 4_565 ?
F2' B1 F3' 110.3(17) . 4_565 ?
F2 B1 F3' 94.2(14) . 4_565 ?
F1 B1 F3' 125(3) . 4_565 ?
F3 B1 F3' 18(2) 4_565 4_565 ?
F3 B1 F3' 106(3) . 4_565 ?
F1' B1 F3' 110.7(16) . . ?
F2' B1 F3' 110.3(17) . . ?
F2 B1 F3' 94.2(14) . . ?
F1 B1 F3' 125(3) . . ?
F3 B1 F3' 106(3) 4_565 . ?
F3 B1 F3' 18(2) . . ?
F3' B1 F3' 101(6) 4_565 . ?
N1 C1 Br1 110.4(16) . . ?
C2 N1 C1 117(2) . . ?
C2 N1 C3 104.5(16) . . ?
C1 N1 C3 111.9(15) . . ?
C2 N1 C3 104.5(16) . 4_565 ?
C1 N1 C3 111.9(15) . 4_565 ?
C3 N1 C3 105(2) . 4_565 ?

_refine_diff_density_max         3.046
_refine_diff_density_min         -1.245
_refine_diff_density_rms         0.332

# start Validation Reply Form

_vrf_PLAT082_P21M                
;
PROBLEM:High R1 Value .................................. 0.28 Report

RESPONSE: The quality of crystal was effected by high temperature. 
          Besides, the BF4 anions were totally disordered.
;
_vrf_PLAT084_P21M                
;
PROBLEM:High wR2 Value (i.e. > 0.25) ................... 0.59 Report
RESPONSE: The quality of crystal was effected by high temperature. 
          Besides, the BF4 anions were totally disordered.
;

_vrf_PLAT971_P21M                
;
PROBLEM:Check Calcd Residual Density  1.31A From     Br1       3.04 eA-3  
RESPONSE: The quality of crystal was effected by high temperature. 
          Besides, the cations were totally disordered.
;

# end Validation Reply Form


_shelx_res_file                  
;

    P21M.res created by SHELXL-2014/7


TITL P21M in P2(1)/m
CELL 0.71073   6.1490   8.0124   9.5075  90.000 101.188  90.000
ZERR    2.00   0.0183   0.0226   0.0279   0.000   0.062   0.000
LATT 1
SYMM -X, 0.5+Y, -Z
SFAC C  H  B  N  F  Br
UNIT 8 22 2 2 8 2
OMIT -1 1 1
OMIT   0.00  50.50
L.S. 40
ACTA
BOND
FMAP 2
PLAN 5
DFIX 1.49 0.02 N1 C1 N1 C2 N1 C3
DFIX 1.90 0.02 C1 BR1
DELU 0.01 N1 C1 C2 C3
SIMU 0.01 N1 C1 C2 C3
DFIX 1.35 0.02 B1 F1 B1 F2 B1 F3
DFIX 2.24 0.02 F1 F2 F2 F3 F1 F3
DFIX 1.35 0.02 B1 F1' B1 F2' B1 F3'
DFIX 2.24 0.02 F1' F2' F2' F3' F1' F3'
DFIX 2.00 0.02 F2 F3'
DELU 0.002 B1 F1' F2' F3'
SIMU 0.002 B1 F1' F2' F3'
DELU 0.002 B1 F1 F2 F3
SIMU 0.002 B1 F1 F2 F3
EADP F3 F3'
EADP F2 F2'
EADP F1 F1'
SIZE 0.38 0.28 0.20
TEMP 95
WGHT    0.200000   27.000000
FVAR       0.78348
BR1   6    0.594854    0.250000    0.002686    10.50000    0.22005    0.11762 =
         0.11386    0.00000    0.10529    0.00000
F3    5    1.011344    0.114705    0.799204    10.50000    0.15728    0.14825 =
         0.13635    0.00027    0.05075    0.00022
F2    5    0.712554    0.250000    0.681283    10.25000    0.15706    0.14849 =
         0.13573    0.00000    0.05055    0.00000
F1    5    1.026770    0.250000    0.596595    10.25000    0.15708    0.14874 =
         0.13584    0.00000    0.05063    0.00000
F3'   5    0.946726    0.118077    0.809521    10.50000    0.15728    0.14825 =
         0.13635    0.00027    0.05075    0.00022
F2'   5    0.743234    0.250000    0.623028    10.25000    0.15706    0.14849 =
         0.13573    0.00000    0.05055    0.00000
F1'   5    1.114619    0.250000    0.653160    10.25000    0.15708    0.14874 =
         0.13584    0.00000    0.05063    0.00000
B1    3    0.937595    0.250000    0.716940    10.50000    0.15708    0.14851 =
         0.13579    0.00000    0.05060    0.00000
C1    1    0.365351    0.250000    0.114748    10.50000    0.04758    0.05528 =
         0.06398    0.00000   -0.01115    0.00000
AFIX   3
H1A   2    0.272861    0.153240    0.092988    10.50000   -1.20000
H1B   2    0.272861    0.346760    0.092988    10.50000   -1.20000
AFIX   0
C3    1    0.610773    0.101016    0.312817    11.00000    0.04158    0.05988 =
         0.08106    0.01051   -0.00656    0.00729
AFIX   3
H3A   2    0.680233    0.092716    0.412117    11.00000   -1.50000
H3B   2    0.520703    0.004076    0.285497    11.00000   -1.50000
H3C   2    0.722603    0.108146    0.255267    11.00000   -1.50000
AFIX   0
C2    1    0.310070    0.250000    0.373260    10.50000    0.04261    0.05669 =
         0.06614    0.00000   -0.00569    0.00000
AFIX   3
H2A   2    0.219930    0.348620    0.357780    10.50000   -1.50000
H2B   2    0.217120    0.152980    0.355920    10.50000   -1.50000
H2C   2    0.390630    0.250000    0.470440    10.50000   -1.50000
AFIX   0
N1    4    0.464654    0.250000    0.270781    10.50000    0.03824    0.04932 =
         0.06064    0.00000   -0.00965    0.00000

HKLF 4

REM  P21M in P2(1)/m
REM R1 =  0.2759 for     557 Fo > 4sig(Fo)  and  0.3247 for all     898 data
REM     68 parameters refined using     89 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  3.046,  deepest hole -1.245,  1-sigma level  0.332
Q1    1   0.7449  0.1545  0.0801  11.00000  0.05    3.05
Q2    1   0.9918  0.1207  0.6048  11.00000  0.05    1.30
Q3    1   0.5890  0.2500 -0.0433  10.50000  0.05    1.07
Q4    1   0.5257  0.2500  0.0069  10.50000  0.05    0.87
Q5    1   0.2153  0.2500  0.1207  10.50000  0.05    0.76
;
_shelx_res_checksum              7703
