# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_5-cl_1804
_database_code_depnum_ccdc_archive 'CCDC 1509612'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_publcif_datablock.id            {dd08427c-4d08-4f1e-ad9f-d6f8df9a81de}

_audit_creation_date             2016-10-09T10:05:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C14 H15 Cl N2 O2'
_chemical_formula_weight         278.73

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

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

_cell_length_a                   13.453(3)
_cell_length_b                   5.8751(12)
_cell_length_c                   17.417(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.50(3)
_cell_angle_gamma                90
_cell_volume                     1348.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3241
_cell_measurement_theta_min      4.0680
_cell_measurement_theta_max      27.5030

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.8357
_exptl_crystal_size_mid          0.1451
_exptl_crystal_size_min          0.0721
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584

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

_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0.0
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_number            11741
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2861
_reflns_number_gt                2507
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_molecular_graphics    MERCURY
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0424P)²+0.9560P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2861
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.04

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.39658(15) 0.4099(3) 0.56152(12) 0.0325(4) Uani 1 1 d . . .
C4 C 0.25731(16) 0.1773(4) 0.53777(13) 0.0420(5) Uani 1 1 d . . .
C5 C 0.30632(15) 0.1681(3) 0.46672(12) 0.0340(4) Uani 1 1 d . . .
C6 C 0.34146(18) -0.0724(4) 0.45169(14) 0.0463(5) Uani 1 1 d . . .
H6A H 0.4066 -0.1053 0.4851 0.056 Uiso 1 1 calc R . .
H6B H 0.2925 -0.1846 0.4614 0.056 Uiso 1 1 calc R . .
C7 C 0.3497(3) -0.0734(6) 0.36761(18) 0.0856(11) Uani 1 1 d . . .
H7A H 0.4192 -0.0447 0.3628 0.103 Uiso 1 1 calc R . .
H7B H 0.329 -0.22 0.3441 0.103 Uiso 1 1 calc R . .
C8 C 0.2822(3) 0.1082(7) 0.32802(17) 0.0945(12) Uani 1 1 d . . .
H8A H 0.2288 0.0426 0.2885 0.113 Uiso 1 1 calc R . .
H8B H 0.3205 0.2141 0.3026 0.113 Uiso 1 1 calc R . .
C9 C 0.23693(19) 0.2301(4) 0.38862(15) 0.0519(6) Uani 1 1 d . . .
H9A H 0.1681 0.1789 0.3874 0.062 Uiso 1 1 calc R . .
H9B H 0.2363 0.3933 0.3801 0.062 Uiso 1 1 calc R . .
C10 C 0.30149(16) 0.3585(4) 0.67014(12) 0.0409(5) Uani 1 1 d . . .
H10A H 0.2311 0.3294 0.6722 0.049 Uiso 1 1 calc R . .
H10B H 0.3153 0.5173 0.6833 0.049 Uiso 1 1 calc R . .
C11 C 0.36816(15) 0.2124(4) 0.73067(12) 0.0363(5) Uani 1 1 d . . .
C12 C 0.40631(17) 0.0049(4) 0.71257(13) 0.0426(5) Uani 1 1 d . . .
H12 H 0.3917 -0.0465 0.661 0.051 Uiso 1 1 calc R . .
C13 C 0.46539(17) -0.1270(4) 0.76915(14) 0.0460(6) Uani 1 1 d . . .
H13 H 0.4909 -0.2656 0.756 0.055 Uiso 1 1 calc R . .
C14 C 0.48621(17) -0.0517(4) 0.84517(14) 0.0461(6) Uani 1 1 d . . .
C15 C 0.44967(19) 0.1538(4) 0.86535(14) 0.0507(6) Uani 1 1 d . . .
H15 H 0.4644 0.204 0.917 0.061 Uiso 1 1 calc R . .
C16 C 0.39103(18) 0.2841(4) 0.80788(13) 0.0438(5) Uani 1 1 d . . .
H16 H 0.3662 0.4233 0.8212 0.053 Uiso 1 1 calc R . .
N1 N 0.39025(13) 0.3262(3) 0.48960(10) 0.0381(4) Uani 1 1 d . . .
H1 H 0.4316 0.3621 0.4597 0.046 Uiso 1 1 calc R . .
N3 N 0.31573(13) 0.3194(3) 0.59094(10) 0.0373(4) Uani 1 1 d . . .
O1 O 0.45878(11) 0.5418(3) 0.59759(8) 0.0428(4) Uani 1 1 d . . .
O2 O 0.18367(13) 0.0749(4) 0.54760(11) 0.0687(6) Uani 1 1 d . . .
Cl1 Cl 0.55980(5) -0.21980(14) 0.91714(4) 0.0687(2) Uani 1 1 d . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.219(2) . ?
C2 N1 1.333(3) . ?
C2 N3 1.397(2) . ?
C4 O2 1.200(3) . ?
C4 N3 1.372(3) . ?
C4 C5 1.515(3) . ?
C5 N1 1.455(3) . ?
C5 C6 1.529(3) . ?
C5 C9 1.532(3) . ?
C6 C7 1.490(4) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.480(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.501(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N3 1.448(3) . ?
C10 C11 1.509(3) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C12 1.383(3) . ?
C11 C16 1.384(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.93 . ?
C13 C14 1.371(3) . ?
C13 H13 0.93 . ?
C14 C15 1.376(3) . ?
C14 Cl1 1.741(2) . ?
C15 C16 1.377(3) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
N1 H1 0.86 . ?

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 C2 N1 128.88(18) . . ?
O1 C2 N3 123.90(18) . . ?
N1 C2 N3 107.22(17) . . ?
O2 C4 N3 125.9(2) . . ?
O2 C4 C5 127.2(2) . . ?
N3 C4 C5 106.82(16) . . ?
N1 C5 C4 101.17(16) . . ?
N1 C5 C6 112.79(17) . . ?
C4 C5 C6 111.90(18) . . ?
N1 C5 C9 113.16(18) . . ?
C4 C5 C9 115.42(18) . . ?
C6 C5 C9 102.83(18) . . ?
C7 C6 C5 105.0(2) . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.8 . . ?
C8 C7 C6 107.2(2) . . ?
C8 C7 H7A 110.3 . . ?
C6 C7 H7A 110.3 . . ?
C8 C7 H7B 110.3 . . ?
C6 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 C9 108.3(2) . . ?
C7 C8 H8A 110 . . ?
C9 C8 H8A 110 . . ?
C7 C8 H8B 110 . . ?
C9 C8 H8B 110 . . ?
H8A C8 H8B 108.4 . . ?
C8 C9 C5 104.5(2) . . ?
C8 C9 H9A 110.9 . . ?
C5 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C5 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
N3 C10 C11 113.71(17) . . ?
N3 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N3 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C16 118.0(2) . . ?
C12 C11 C10 122.6(2) . . ?
C16 C11 C10 119.46(19) . . ?
C13 C12 C11 121.4(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.0(2) . . ?
C13 C14 Cl1 119.31(19) . . ?
C15 C14 Cl1 119.66(19) . . ?
C14 C15 C16 119.0(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C11 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C2 N1 C5 113.18(16) . . ?
C2 N1 H1 123.4 . . ?
C5 N1 H1 123.4 . . ?
C4 N3 C2 111.54(17) . . ?
C4 N3 C10 124.94(17) . . ?
C2 N3 C10 123.34(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C4 C5 N1 179.9(2) . . . . ?
N3 C4 C5 N1 -2.5(2) . . . . ?
O2 C4 C5 C6 -59.8(3) . . . . ?
N3 C4 C5 C6 117.8(2) . . . . ?
O2 C4 C5 C9 57.4(3) . . . . ?
N3 C4 C5 C9 -125.0(2) . . . . ?
N1 C5 C6 C7 -87.8(3) . . . . ?
C4 C5 C6 C7 158.9(2) . . . . ?
C9 C5 C6 C7 34.4(3) . . . . ?
C5 C6 C7 C8 -23.7(4) . . . . ?
C6 C7 C8 C9 3.2(4) . . . . ?
C7 C8 C9 C5 18.4(4) . . . . ?
N1 C5 C9 C8 89.8(3) . . . . ?
C4 C5 C9 C8 -154.3(2) . . . . ?
C6 C5 C9 C8 -32.2(3) . . . . ?
N3 C10 C11 C12 -25.1(3) . . . . ?
N3 C10 C11 C16 156.30(19) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 -178.8(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 Cl1 179.28(17) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
Cl1 C14 C15 C16 -179.57(18) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
C10 C11 C16 C15 178.5(2) . . . . ?
O1 C2 N1 C5 178.7(2) . . . . ?
N3 C2 N1 C5 -1.8(2) . . . . ?
C4 C5 N1 C2 2.6(2) . . . . ?
C6 C5 N1 C2 -117.1(2) . . . . ?
C9 C5 N1 C2 126.7(2) . . . . ?
O2 C4 N3 C2 179.3(2) . . . . ?
C5 C4 N3 C2 1.7(2) . . . . ?
O2 C4 N3 C10 4.0(4) . . . . ?
C5 C4 N3 C10 -173.66(18) . . . . ?
O1 C2 N3 C4 179.5(2) . . . . ?
N1 C2 N3 C4 0.0(2) . . . . ?
O1 C2 N3 C10 -5.1(3) . . . . ?
N1 C2 N3 C10 175.40(19) . . . . ?
C11 C10 N3 C4 95.8(2) . . . . ?
C11 C10 N3 C2 -79.0(2) . . . . ?
####################################################################### 
# 
# 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_5br_1794
_database_code_depnum_ccdc_archive 'CCDC 1509613'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_publcif_datablock.id            {a4b90a40-aae1-482a-b3c5-202a911df63b}

_audit_creation_date             2016-10-09T10:03:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C14 H15 Br N2 O2'
_chemical_formula_weight         323.19

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

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

_cell_length_a                   13.622(3)
_cell_length_b                   5.9260(12)
_cell_length_c                   17.379(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.00(3)
_cell_angle_gamma                90
_cell_volume                     1377.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1692
_cell_measurement_theta_min      3.8500
_cell_measurement_theta_max      26.6630

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656

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

_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85963
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0.0
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_number            6989
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2715
_reflns_number_gt                2152
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_molecular_graphics    MERCURY
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0352P)²+1.0556P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2715
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.052

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.3939(2) 0.0883(4) 0.55886(16) 0.0335(6) Uani 1 1 d . . .
C4 C 0.2579(2) 0.3227(5) 0.53290(17) 0.0417(7) Uani 1 1 d . . .
C5 C 0.30926(19) 0.3310(4) 0.46290(16) 0.0349(6) Uani 1 1 d . . .
C6 C 0.3463(2) 0.5691(5) 0.44914(18) 0.0464(7) Uani 1 1 d . . .
H6A H 0.298 0.6816 0.4581 0.056 Uiso 1 1 calc R . .
H6B H 0.4096 0.5996 0.4838 0.056 Uiso 1 1 calc R . .
C7 C 0.3581(4) 0.5703(7) 0.3654(2) 0.0824(13) Uani 1 1 d . . .
H7A H 0.3392 0.7162 0.3419 0.099 Uiso 1 1 calc R . .
H7B H 0.4271 0.5408 0.3619 0.099 Uiso 1 1 calc R . .
C8 C 0.2923(4) 0.3916(8) 0.3241(2) 0.0915(14) Uani 1 1 d . . .
H8A H 0.3312 0.2857 0.2997 0.11 Uiso 1 1 calc R . .
H8B H 0.2416 0.4578 0.2835 0.11 Uiso 1 1 calc R . .
C9 C 0.2435(2) 0.2715(5) 0.38381(18) 0.0499(8) Uani 1 1 d . . .
H9A H 0.2422 0.1097 0.3752 0.06 Uiso 1 1 calc R . .
H9B H 0.1755 0.3245 0.3812 0.06 Uiso 1 1 calc R . .
C10 C 0.2958(2) 0.1426(5) 0.66592(16) 0.0400(7) Uani 1 1 d . . .
H10A H 0.3073 -0.0153 0.6793 0.048 Uiso 1 1 calc R . .
H10B H 0.2266 0.1764 0.6676 0.048 Uiso 1 1 calc R . .
C11 C 0.3627(2) 0.2852(4) 0.72627(16) 0.0365(6) Uani 1 1 d . . .
C12 C 0.3979(2) 0.4943(5) 0.70847(17) 0.0418(7) Uani 1 1 d . . .
H12 H 0.3808 0.5494 0.6576 0.05 Uiso 1 1 calc R . .
C13 C 0.4579(2) 0.6222(5) 0.76491(17) 0.0439(7) Uani 1 1 d . . .
H13 H 0.4817 0.7616 0.752 0.053 Uiso 1 1 calc R . .
C14 C 0.4823(2) 0.5429(5) 0.83998(17) 0.0430(7) Uani 1 1 d . . .
C15 C 0.4483(2) 0.3359(5) 0.86012(18) 0.0490(8) Uani 1 1 d . . .
H15 H 0.4652 0.2826 0.9113 0.059 Uiso 1 1 calc R . .
C16 C 0.3886(2) 0.2099(5) 0.80282(18) 0.0444(7) Uani 1 1 d . . .
H16 H 0.3652 0.0705 0.816 0.053 Uiso 1 1 calc R . .
N1 N 0.39073(17) 0.1717(4) 0.48699(13) 0.0392(6) Uani 1 1 d . . .
H1 H 0.4326 0.135 0.4579 0.047 Uiso 1 1 calc R . .
N3 N 0.31244(17) 0.1797(4) 0.58664(13) 0.0369(5) Uani 1 1 d . . .
O1 O 0.45354(14) -0.0432(3) 0.59580(11) 0.0431(5) Uani 1 1 d . . .
O2 O 0.18524(17) 0.4284(4) 0.54252(14) 0.0647(7) Uani 1 1 d . . .
Br1 Br 0.56313(3) 0.72198(6) 0.91797(2) 0.06282(15) Uani 1 1 d . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.217(3) . ?
C2 N1 1.336(3) . ?
C2 N3 1.400(3) . ?
C4 O2 1.209(3) . ?
C4 N3 1.370(4) . ?
C4 C5 1.516(4) . ?
C5 N1 1.456(3) . ?
C5 C9 1.532(4) . ?
C5 C6 1.532(4) . ?
C6 C7 1.494(5) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.481(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.513(5) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N3 1.455(3) . ?
C10 C11 1.510(4) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C16 1.384(4) . ?
C11 C12 1.385(4) . ?
C12 C13 1.378(4) . ?
C12 H12 0.93 . ?
C13 C14 1.367(4) . ?
C13 H13 0.93 . ?
C14 C15 1.380(4) . ?
C14 Br1 1.899(3) . ?
C15 C16 1.379(4) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
N1 H1 0.86 . ?

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 C2 N1 129.0(2) . . ?
O1 C2 N3 124.0(2) . . ?
N1 C2 N3 107.0(2) . . ?
O2 C4 N3 125.3(3) . . ?
O2 C4 C5 127.5(3) . . ?
N3 C4 C5 107.1(2) . . ?
N1 C5 C4 101.0(2) . . ?
N1 C5 C9 113.1(2) . . ?
C4 C5 C9 115.6(2) . . ?
N1 C5 C6 112.7(2) . . ?
C4 C5 C6 111.8(2) . . ?
C9 C5 C6 103.0(2) . . ?
C7 C6 C5 104.8(3) . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C8 C7 C6 107.5(3) . . ?
C8 C7 H7A 110.2 . . ?
C6 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 C9 108.0(3) . . ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C8 C9 C5 104.4(3) . . ?
C8 C9 H9A 110.9 . . ?
C5 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C5 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
N3 C10 C11 113.0(2) . . ?
N3 C10 H10A 109 . . ?
C11 C10 H10A 109 . . ?
N3 C10 H10B 109 . . ?
C11 C10 H10B 109 . . ?
H10A C10 H10B 107.8 . . ?
C16 C11 C12 117.9(3) . . ?
C16 C11 C10 119.8(2) . . ?
C12 C11 C10 122.3(3) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 Br1 119.5(2) . . ?
C15 C14 Br1 119.5(2) . . ?
C16 C15 C14 118.6(3) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C11 121.8(3) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
C2 N1 C5 113.3(2) . . ?
C2 N1 H1 123.4 . . ?
C5 N1 H1 123.4 . . ?
C4 N3 C2 111.5(2) . . ?
C4 N3 C10 125.2(2) . . ?
C2 N3 C10 123.0(2) . . ?

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
O2 C4 C5 N1 179.1(3) . . . . ?
N3 C4 C5 N1 2.2(3) . . . . ?
O2 C4 C5 C9 -58.4(4) . . . . ?
N3 C4 C5 C9 124.7(3) . . . . ?
O2 C4 C5 C6 59.0(4) . . . . ?
N3 C4 C5 C6 -117.9(3) . . . . ?
N1 C5 C6 C7 87.8(3) . . . . ?
C4 C5 C6 C7 -159.2(3) . . . . ?
C9 C5 C6 C7 -34.4(3) . . . . ?
C5 C6 C7 C8 23.4(4) . . . . ?
C6 C7 C8 C9 -2.8(5) . . . . ?
C7 C8 C9 C5 -18.8(5) . . . . ?
N1 C5 C9 C8 -89.6(3) . . . . ?
C4 C5 C9 C8 154.6(3) . . . . ?
C6 C5 C9 C8 32.4(3) . . . . ?
N3 C10 C11 C16 -152.4(3) . . . . ?
N3 C10 C11 C12 29.3(4) . . . . ?
C16 C11 C12 C13 0.9(4) . . . . ?
C10 C11 C12 C13 179.2(3) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C12 C13 C14 Br1 -178.9(2) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
Br1 C14 C15 C16 179.2(2) . . . . ?
C14 C15 C16 C11 0.2(5) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C10 C11 C16 C15 -179.0(3) . . . . ?
O1 C2 N1 C5 -178.3(3) . . . . ?
N3 C2 N1 C5 2.2(3) . . . . ?
C4 C5 N1 C2 -2.7(3) . . . . ?
C9 C5 N1 C2 -126.9(3) . . . . ?
C6 C5 N1 C2 116.7(3) . . . . ?
O2 C4 N3 C2 -178.2(3) . . . . ?
C5 C4 N3 C2 -1.2(3) . . . . ?
O2 C4 N3 C10 -4.2(5) . . . . ?
C5 C4 N3 C10 172.8(2) . . . . ?
O1 C2 N3 C4 179.9(3) . . . . ?
N1 C2 N3 C4 -0.5(3) . . . . ?
O1 C2 N3 C10 5.8(4) . . . . ?
N1 C2 N3 C10 -174.6(2) . . . . ?
C11 C10 N3 C4 -96.0(3) . . . . ?
C11 C10 N3 C2 77.3(3) . . . . ?
####################################################################### 
# 
# 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_6cl_1796
_database_code_depnum_ccdc_archive 'CCDC 1509614'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_publcif_datablock.id            {e19a49c3-6316-4808-97c2-49f152979766}

_audit_creation_date             2016-10-09T10:09:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C15 H17 Cl N2 O2'
_chemical_formula_weight         292.76

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

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

_cell_length_a                   13.287(3)
_cell_length_b                   5.9132(12)
_cell_length_c                   18.536(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.09(3)
_cell_angle_gamma                90
_cell_volume                     1438.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4647
_cell_measurement_theta_min      3.7770
_cell_measurement_theta_max      28.2250
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0.0
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.022
_diffrn_reflns_number            15320
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.453
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             2941
_reflns_number_gt                2461
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_molecular_graphics    MERCURY
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.4539P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2941
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.067

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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 0.40792(13) 0.3866(3) 0.56895(9) 0.0343(4) Uani 1 1 d . . . . .
C4 C 0.27622(14) 0.1343(3) 0.55783(10) 0.0390(4) Uani 1 1 d . . . . .
C5 C 0.30595(13) 0.1632(3) 0.48302(9) 0.0321(4) Uani 1 1 d . . . . .
C6 C 0.33402(16) -0.0599(3) 0.45060(12) 0.0466(5) Uani 1 1 d . . . . .
H6A H 0.2784 -0.1664 0.4501 0.056 Uiso 1 1 calc R U . . .
H6B H 0.3938 -0.1226 0.4808 0.056 Uiso 1 1 calc R U . . .
C7 C 0.3559(2) -0.0265(4) 0.37279(13) 0.0627(7) Uani 1 1 d . . . . .
H7A H 0.4163 0.0668 0.374 0.075 Uiso 1 1 calc R U . . .
H7B H 0.3696 -0.1721 0.3522 0.075 Uiso 1 1 calc R U . . .
C8 C 0.2673(2) 0.0846(5) 0.32469(12) 0.0723(7) Uani 1 1 d . . . . .
H8A H 0.285 0.1104 0.2766 0.087 Uiso 1 1 calc R U . . .
H8B H 0.2089 -0.0158 0.3193 0.087 Uiso 1 1 calc R U . . .
C9 C 0.2395(2) 0.3061(4) 0.35626(12) 0.0615(6) Uani 1 1 d . . . . .
H9A H 0.18 0.3685 0.3258 0.074 Uiso 1 1 calc R U . . .
H9B H 0.2952 0.4123 0.3566 0.074 Uiso 1 1 calc R U . . .
C10 C 0.21727(15) 0.2758(3) 0.43356(10) 0.0432(5) Uani 1 1 d . . . . .
H10A H 0.1565 0.1841 0.4324 0.052 Uiso 1 1 calc R U . . .
H10B H 0.204 0.4224 0.4536 0.052 Uiso 1 1 calc R U . . .
C11 C 0.32250(15) 0.3211(3) 0.67949(9) 0.0404(4) Uani 1 1 d . . . . .
H11A H 0.2503 0.3097 0.682 0.049 Uiso 1 1 calc R U . . .
H11B H 0.343 0.476 0.6911 0.049 Uiso 1 1 calc R U . . .
C12 C 0.37970(13) 0.1684(3) 0.73708(9) 0.0329(4) Uani 1 1 d . . . . .
C13 C 0.42170(14) -0.0372(3) 0.72220(10) 0.0400(4) Uani 1 1 d . . . . .
H13 H 0.4173 -0.0851 0.674 0.048 Uiso 1 1 calc R U . . .
C14 C 0.47008(15) -0.1727(3) 0.77800(11) 0.0436(4) Uani 1 1 d . . . . .
H14 H 0.4989 -0.3097 0.7675 0.052 Uiso 1 1 calc R U . . .
C15 C 0.47502(14) -0.1024(3) 0.84928(10) 0.0412(4) Uani 1 1 d . . . . .
C16 C 0.43388(16) 0.1012(3) 0.86561(10) 0.0446(5) Uani 1 1 d . . . . .
H16 H 0.4377 0.1477 0.9139 0.054 Uiso 1 1 calc R U . . .
C17 C 0.38703(15) 0.2348(3) 0.80933(10) 0.0404(4) Uani 1 1 d . . . . .
H17 H 0.3596 0.3732 0.8201 0.048 Uiso 1 1 calc R U . . .
N1 N 0.39281(11) 0.3156(3) 0.49975(8) 0.0371(4) Uani 1 1 d . . . . .
H1 H 0.4304 0.3556 0.4682 0.045 Uiso 1 1 calc R U . . .
N3 N 0.33726(12) 0.2744(3) 0.60487(8) 0.0373(4) Uani 1 1 d . . . . .
O1 O 0.47033(10) 0.5226(2) 0.59830(7) 0.0465(4) Uani 1 1 d . . . . .
O2 O 0.20979(12) 0.0140(3) 0.57383(8) 0.0639(5) Uani 1 1 d . . . . .
Cl1 Cl 0.53447(5) -0.27263(10) 0.92008(3) 0.0640(2) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.220(2) . ?
C2 N1 1.334(2) . ?
C2 N3 1.401(2) . ?
C4 O2 1.207(2) . ?
C4 N3 1.371(2) . ?
C4 C5 1.510(2) . ?
C5 N1 1.459(2) . ?
C5 C6 1.520(3) . ?
C5 C10 1.527(2) . ?
C6 C7 1.529(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.510(4) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.504(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.519(3) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N3 1.454(2) . ?
C11 C12 1.509(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.384(3) . ?
C12 C17 1.384(2) . ?
C13 C14 1.384(3) . ?
C13 H13 0.93 . ?
C14 C15 1.377(3) . ?
C14 H14 0.93 . ?
C15 C16 1.375(3) . ?
C15 Cl1 1.741(2) . ?
C16 C17 1.377(3) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?

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 C2 N1 128.66(16) . . ?
O1 C2 N3 124.03(16) . . ?
N1 C2 N3 107.31(15) . . ?
O2 C4 N3 125.57(17) . . ?
O2 C4 C5 126.87(17) . . ?
N3 C4 C5 107.54(14) . . ?
N1 C5 C4 100.81(13) . . ?
N1 C5 C6 112.64(15) . . ?
C4 C5 C6 112.39(15) . . ?
N1 C5 C10 111.57(14) . . ?
C4 C5 C10 108.16(15) . . ?
C6 C5 C10 110.82(15) . . ?
C5 C6 C7 110.86(16) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 111.48(19) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108 . . ?
C9 C8 C7 111.44(19) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108 . . ?
C8 C9 C10 111.14(19) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
C9 C10 C5 111.79(17) . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C5 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 C12 115.51(15) . . ?
N3 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
N3 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C17 118.24(17) . . ?
C13 C12 C11 123.98(16) . . ?
C17 C12 C11 117.73(16) . . ?
C14 C13 C12 120.94(17) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 119.25(17) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 121.01(18) . . ?
C16 C15 Cl1 119.26(15) . . ?
C14 C15 Cl1 119.73(15) . . ?
C15 C16 C17 118.91(17) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C12 121.64(17) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
C2 N1 C5 113.12(14) . . ?
C2 N1 H1 123.4 . . ?
C5 N1 H1 123.4 . . ?
C4 N3 C2 110.92(14) . . ?
C4 N3 C11 124.39(15) . . ?
C2 N3 C11 124.29(15) . . ?

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
O2 C4 C5 N1 -176.7(2) . . . . ?
N3 C4 C5 N1 4.64(18) . . . . ?
O2 C4 C5 C6 -56.5(3) . . . . ?
N3 C4 C5 C6 124.81(17) . . . . ?
O2 C4 C5 C10 66.2(3) . . . . ?
N3 C4 C5 C10 -112.53(16) . . . . ?
N1 C5 C6 C7 -71.2(2) . . . . ?
C4 C5 C6 C7 175.79(17) . . . . ?
C10 C5 C6 C7 54.6(2) . . . . ?
C5 C6 C7 C8 -55.6(2) . . . . ?
C6 C7 C8 C9 56.1(3) . . . . ?
C7 C8 C9 C10 -55.6(3) . . . . ?
C8 C9 C10 C5 55.2(3) . . . . ?
N1 C5 C10 C9 71.5(2) . . . . ?
C4 C5 C10 C9 -178.52(17) . . . . ?
C6 C5 C10 C9 -54.9(2) . . . . ?
N3 C11 C12 C13 -16.7(3) . . . . ?
N3 C11 C12 C17 165.83(16) . . . . ?
C17 C12 C13 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 -177.66(17) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C13 C14 C15 Cl1 179.30(14) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
Cl1 C15 C16 C17 179.99(15) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C11 C12 C17 C16 177.09(18) . . . . ?
O1 C2 N1 C5 -175.85(18) . . . . ?
N3 C2 N1 C5 4.3(2) . . . . ?
C4 C5 N1 C2 -5.50(19) . . . . ?
C6 C5 N1 C2 -125.49(17) . . . . ?
C10 C5 N1 C2 109.13(17) . . . . ?
O2 C4 N3 C2 178.7(2) . . . . ?
C5 C4 N3 C2 -2.6(2) . . . . ?
O2 C4 N3 C11 -8.3(3) . . . . ?
C5 C4 N3 C11 170.41(16) . . . . ?
O1 C2 N3 C4 179.20(18) . . . . ?
N1 C2 N3 C4 -0.9(2) . . . . ?
O1 C2 N3 C11 6.2(3) . . . . ?
N1 C2 N3 C11 -173.89(16) . . . . ?
C12 C11 N3 C4 92.0(2) . . . . ?
C12 C11 N3 C2 -95.9(2) . . . . ?
####################################################################### 
# 
# 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_6-br_1808
_database_code_depnum_ccdc_archive 'CCDC 1509615'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_publcif_datablock.id            {0f4b2ccd-0390-4567-a588-32225302944e}

_audit_creation_date             2016-10-09T10:07:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C15 H17 Br N2 O2'
_chemical_formula_weight         337.21

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

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

_cell_length_a                   13.505(3)
_cell_length_b                   5.9344(12)
_cell_length_c                   18.587(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.49(3)
_cell_angle_gamma                90
_cell_volume                     1476.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3876
_cell_measurement_theta_min      3.7260
_cell_measurement_theta_max      27.5090
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.8961
_exptl_crystal_size_mid          0.2552
_exptl_crystal_size_min          0.0707
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

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

_exptl_absorpt_coefficient_mu    2.790
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.213
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0.0
_diffrn_reflns_av_R_equivalents  0.08
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_number            15743
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.521
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3025
_reflns_number_gt                2557
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_molecular_graphics    MERCURY
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0993P)²+0.2147P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.392(17)
_refine_ls_number_reflns         3025
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.163
_refine_ls_wR_factor_gt          0.154
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.635
_refine_diff_density_min         -1.634
_refine_diff_density_rms         0.21

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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 0.5934(2) 0.1154(5) 0.43163(15) 0.0406(6) Uani 1 1 d . . . . .
C4 C 0.7231(2) 0.3656(6) 0.44363(16) 0.0437(7) Uani 1 1 d . . . . .
C5 C 0.6912(2) 0.3345(5) 0.51794(16) 0.0390(6) Uani 1 1 d . . . . .
C6 C 0.7760(3) 0.2173(6) 0.5662(2) 0.0523(8) Uani 1 1 d . . . . .
H6A H 0.7889 0.0723 0.5452 0.063 Uiso 1 1 calc R U . . .
H6B H 0.8362 0.3073 0.5677 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7524(4) 0.1823(8) 0.6425(2) 0.0738(12) Uani 1 1 d . . . . .
H7A H 0.8102 0.1189 0.672 0.089 Uiso 1 1 calc R U . . .
H7B H 0.6977 0.076 0.6419 0.089 Uiso 1 1 calc R U . . .
C8 C 0.7239(4) 0.4033(10) 0.6757(2) 0.0894(15) Uani 1 1 d . . . . .
H8A H 0.7041 0.3742 0.7232 0.107 Uiso 1 1 calc R U . . .
H8B H 0.7815 0.5023 0.6821 0.107 Uiso 1 1 calc R U . . .
C9 C 0.6397(4) 0.5187(7) 0.6290(3) 0.0789(14) Uani 1 1 d . . . . .
H9A H 0.6266 0.6628 0.6505 0.095 Uiso 1 1 calc R U . . .
H9B H 0.5798 0.4276 0.6276 0.095 Uiso 1 1 calc R U . . .
C10 C 0.6627(3) 0.5574(5) 0.5509(2) 0.0549(8) Uani 1 1 d . . . . .
H10A H 0.6045 0.6202 0.5217 0.066 Uiso 1 1 calc R U . . .
H10B H 0.7172 0.664 0.5513 0.066 Uiso 1 1 calc R U . . .
C11 C 0.6817(3) 0.1836(6) 0.32205(16) 0.0445(7) Uani 1 1 d . . . . .
H11A H 0.664 0.0281 0.3105 0.053 Uiso 1 1 calc R U . . .
H11B H 0.7525 0.2 0.3191 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6249(2) 0.3330(5) 0.26503(16) 0.0386(6) Uani 1 1 d . . . . .
C13 C 0.6166(3) 0.2643(5) 0.19330(19) 0.0474(8) Uani 1 1 d . . . . .
H13 H 0.6434 0.1262 0.1822 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5695(3) 0.3953(6) 0.13797(18) 0.0522(8) Uani 1 1 d . . . . .
H14 H 0.5654 0.3476 0.09 0.063 Uiso 1 1 calc R U . . .
C15 C 0.5284(2) 0.5991(5) 0.15494(17) 0.0451(7) Uani 1 1 d . . . . .
C16 C 0.5354(2) 0.6727(5) 0.2256(2) 0.0491(8) Uani 1 1 d . . . . .
H16 H 0.508 0.8106 0.2363 0.059 Uiso 1 1 calc R U . . .
C17 C 0.5835(2) 0.5397(5) 0.28054(17) 0.0458(7) Uani 1 1 d . . . . .
H17 H 0.5883 0.5888 0.3284 0.055 Uiso 1 1 calc R U . . .
N1 N 0.6047(2) 0.1848(4) 0.50042(14) 0.0444(6) Uani 1 1 d . . . . .
H1 H 0.5656 0.1462 0.5313 0.053 Uiso 1 1 calc R U . . .
N3 N 0.6646(2) 0.2274(4) 0.39615(15) 0.0427(6) Uani 1 1 d . . . . .
O1 O 0.53257(17) -0.0193(4) 0.40187(12) 0.0546(6) Uani 1 1 d . . . . .
O2 O 0.78930(18) 0.4863(5) 0.42826(13) 0.0685(8) Uani 1 1 d . . . . .
Br1 Br 0.46372(3) 0.78027(8) 0.07850(2) 0.0667(3) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.225(4) . ?
C2 N1 1.333(4) . ?
C2 N3 1.403(3) . ?
C4 O2 1.208(4) . ?
C4 N3 1.377(4) . ?
C4 C5 1.511(4) . ?
C5 N1 1.470(4) . ?
C5 C6 1.526(5) . ?
C5 C10 1.528(4) . ?
C6 C7 1.508(5) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.521(8) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.503(8) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.540(6) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N3 1.449(4) . ?
C11 C12 1.512(4) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.385(4) . ?
C12 C17 1.394(4) . ?
C13 C14 1.377(5) . ?
C13 H13 0.93 . ?
C14 C15 1.384(5) . ?
C14 H14 0.93 . ?
C15 C16 1.376(5) . ?
C15 Br1 1.901(3) . ?
C16 C17 1.384(5) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?

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 C2 N1 128.4(2) . . ?
O1 C2 N3 123.9(3) . . ?
N1 C2 N3 107.7(2) . . ?
O2 C4 N3 125.6(3) . . ?
O2 C4 C5 126.6(3) . . ?
N3 C4 C5 107.8(2) . . ?
N1 C5 C4 100.6(2) . . ?
N1 C5 C6 111.6(2) . . ?
C4 C5 C6 108.1(3) . . ?
N1 C5 C10 112.1(3) . . ?
C4 C5 C10 112.2(3) . . ?
C6 C5 C10 111.6(3) . . ?
C7 C6 C5 112.4(3) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 111.0(4) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108 . . ?
C9 C8 C7 111.8(3) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 112.5(3) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C5 C10 C9 110.0(3) . . ?
C5 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C5 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N3 C11 C12 115.6(3) . . ?
N3 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
N3 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C11 118.2(3) . . ?
C17 C12 C11 123.5(3) . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 118.9(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 Br1 120.1(2) . . ?
C14 C15 Br1 118.9(2) . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C2 N1 C5 112.8(2) . . ?
C2 N1 H1 123.6 . . ?
C5 N1 H1 123.6 . . ?
C4 N3 C2 110.7(2) . . ?
C4 N3 C11 124.5(2) . . ?
C2 N3 C11 124.4(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
O2 C4 C5 N1 175.8(3) . . . . ?
N3 C4 C5 N1 -5.5(3) . . . . ?
O2 C4 C5 C6 -67.0(4) . . . . ?
N3 C4 C5 C6 111.7(3) . . . . ?
O2 C4 C5 C10 56.5(5) . . . . ?
N3 C4 C5 C10 -124.8(3) . . . . ?
N1 C5 C6 C7 -71.4(4) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C10 C5 C6 C7 55.0(4) . . . . ?
C5 C6 C7 C8 -54.5(5) . . . . ?
C6 C7 C8 C9 54.6(5) . . . . ?
C7 C8 C9 C10 -55.3(5) . . . . ?
N1 C5 C10 C9 72.5(4) . . . . ?
C4 C5 C10 C9 -175.1(3) . . . . ?
C6 C5 C10 C9 -53.6(4) . . . . ?
C8 C9 C10 C5 54.5(4) . . . . ?
N3 C11 C12 C13 -163.1(3) . . . . ?
N3 C11 C12 C17 19.1(4) . . . . ?
C17 C12 C13 C14 0.5(5) . . . . ?
C11 C12 C13 C14 -177.4(3) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C16 1.0(5) . . . . ?
C13 C14 C15 Br1 179.8(3) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
Br1 C15 C16 C17 -179.4(2) . . . . ?
C15 C16 C17 C12 0.2(5) . . . . ?
C13 C12 C17 C16 -0.1(4) . . . . ?
C11 C12 C17 C16 177.7(3) . . . . ?
O1 C2 N1 C5 175.4(3) . . . . ?
N3 C2 N1 C5 -5.3(4) . . . . ?
C4 C5 N1 C2 6.6(3) . . . . ?
C6 C5 N1 C2 -107.9(3) . . . . ?
C10 C5 N1 C2 126.1(3) . . . . ?
O2 C4 N3 C2 -178.4(3) . . . . ?
C5 C4 N3 C2 2.9(3) . . . . ?
O2 C4 N3 C11 8.3(5) . . . . ?
C5 C4 N3 C11 -170.4(3) . . . . ?
O1 C2 N3 C4 -179.3(3) . . . . ?
N1 C2 N3 C4 1.4(4) . . . . ?
O1 C2 N3 C11 -5.9(5) . . . . ?
N1 C2 N3 C11 174.7(3) . . . . ?
C12 C11 N3 C4 -93.9(4) . . . . ?
C12 C11 N3 C2 93.6(4) . . . . ?
####################################################################### 
# 
# 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_7cl_1800
_database_code_depnum_ccdc_archive 'CCDC 1509616'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_publcif_datablock.id            {74158cfb-7280-4b8d-bf40-25fe67c9c9fb}

_audit_creation_date             2016-10-09T10:11:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16 H19 Cl N2 O2'
_chemical_formula_weight         306.78

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

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

_cell_length_a                   6.4340(13)
_cell_length_b                   13.594(3)
_cell_length_c                   18.649(4)
_cell_angle_alpha                72.12(3)
_cell_angle_beta                 84.92(3)
_cell_angle_gamma                84.41(3)
_cell_volume                     1542.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4170
_cell_measurement_theta_min      3.6680
_cell_measurement_theta_max      28.0250
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648

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

_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0.0
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.033
_diffrn_reflns_number            16450
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             6044
_reflns_number_gt                4542
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_molecular_graphics    MERCURY
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.7371P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6044
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.038

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2A C -0.1137(3) 0.57447(18) 0.57376(12) 0.0391(5) Uani 1 1 d . . .
C2B C 0.3521(3) 0.56088(17) 0.90474(12) 0.0346(5) Uani 1 1 d . . .
C4A C -0.3328(3) 0.53682(18) 0.67994(13) 0.0414(5) Uani 1 1 d . . .
C4B C 0.1455(3) 0.51177(17) 0.83063(13) 0.0383(5) Uani 1 1 d . . .
C5A C -0.3187(3) 0.44473(17) 0.64903(12) 0.0378(5) Uani 1 1 d . . .
C5B C 0.1932(3) 0.41716(16) 0.89781(12) 0.0350(5) Uani 1 1 d . . .
C6A C -0.2201(4) 0.34980(19) 0.70693(14) 0.0503(6) Uani 1 1 d . . .
H6A1 H -0.0988 0.3704 0.7246 0.06 Uiso 1 1 calc R . .
H6A2 H -0.3199 0.3285 0.7499 0.06 Uiso 1 1 calc R . .
C6B C -0.0079(4) 0.38463(19) 0.94784(15) 0.0486(6) Uani 1 1 d . . .
H6B1 H 0.0307 0.3556 0.9997 0.058 Uiso 1 1 calc R . .
H6B2 H -0.0985 0.4468 0.9452 0.058 Uiso 1 1 calc R . .
C7A C -0.1521(5) 0.2566(2) 0.67984(19) 0.0665(8) Uani 1 1 d . . .
H7A1 H -0.0607 0.2799 0.6347 0.08 Uiso 1 1 calc R . .
H7A2 H -0.0682 0.2083 0.718 0.08 Uiso 1 1 calc R . .
C7B C -0.1326(4) 0.3089(2) 0.93032(18) 0.0613(7) Uani 1 1 d . . .
H7B1 H -0.1315 0.3248 0.8759 0.074 Uiso 1 1 calc R . .
H7B2 H -0.2765 0.3186 0.9488 0.074 Uiso 1 1 calc R . .
C8A C -0.3099(7) 0.1994(3) 0.6629(4) 0.138(2) Uani 1 1 d . . .
H8A1 H -0.2468 0.1719 0.6232 0.165 Uiso 1 1 calc R . .
H8A2 H -0.329 0.1402 0.7073 0.165 Uiso 1 1 calc R . .
C8B C -0.0581(4) 0.1955(2) 0.9632(2) 0.0705(8) Uani 1 1 d . . .
H8B1 H -0.0445 0.1818 1.0168 0.085 Uiso 1 1 calc R . .
H8B2 H -0.1659 0.1536 0.9577 0.085 Uiso 1 1 calc R . .
C9A C -0.5161(7) 0.2410(3) 0.6408(3) 0.1235(18) Uani 1 1 d . . .
H9A1 H -0.6044 0.2335 0.6868 0.148 Uiso 1 1 calc R . .
H9A2 H -0.5665 0.1965 0.6153 0.148 Uiso 1 1 calc R . .
C9B C 0.1464(5) 0.1597(2) 0.9292(2) 0.0728(9) Uani 1 1 d . . .
H9B1 H 0.1247 0.1593 0.8785 0.087 Uiso 1 1 calc R . .
H9B2 H 0.1843 0.0888 0.9586 0.087 Uiso 1 1 calc R . .
C10A C -0.5548(5) 0.3480(3) 0.5929(2) 0.0776(9) Uani 1 1 d . . .
H10A H -0.6942 0.3555 0.575 0.093 Uiso 1 1 calc R . .
H10B H -0.4567 0.3591 0.549 0.093 Uiso 1 1 calc R . .
C10B C 0.3296(4) 0.22476(19) 0.92539(17) 0.0577(7) Uani 1 1 d . . .
H10C H 0.3424 0.2317 0.975 0.069 Uiso 1 1 calc R . .
H10D H 0.4575 0.1884 0.9122 0.069 Uiso 1 1 calc R . .
C11A C -0.5378(4) 0.4326(2) 0.62822(15) 0.0529(6) Uani 1 1 d . . .
H11A H -0.6302 0.4196 0.6736 0.064 Uiso 1 1 calc R . .
H11B H -0.5884 0.4979 0.5935 0.064 Uiso 1 1 calc R . .
C11B C 0.3085(4) 0.33159(18) 0.86907(14) 0.0447(6) Uani 1 1 d . . .
H11C H 0.2364 0.327 0.8268 0.054 Uiso 1 1 calc R . .
H11D H 0.4478 0.3523 0.8499 0.054 Uiso 1 1 calc R . .
C12A C -0.1772(4) 0.70737(19) 0.64334(15) 0.0489(6) Uani 1 1 d . . .
H12A H -0.0517 0.7331 0.6134 0.059 Uiso 1 1 calc R . .
H12B H -0.1503 0.6937 0.696 0.059 Uiso 1 1 calc R . .
C12B C 0.2345(3) 0.69693(17) 0.78819(12) 0.0404(5) Uani 1 1 d . . .
H12C H 0.2101 0.6935 0.7385 0.048 Uiso 1 1 calc R . .
H12D H 0.3716 0.7224 0.7855 0.048 Uiso 1 1 calc R . .
C13A C -0.3528(4) 0.79118(17) 0.62384(12) 0.0380(5) Uani 1 1 d . . .
C13B C 0.0716(3) 0.77243(16) 0.80921(12) 0.0375(5) Uani 1 1 d . . .
C14A C -0.3452(4) 0.87728(19) 0.64727(15) 0.0514(6) Uani 1 1 d . . .
H14A H -0.233 0.882 0.6739 0.062 Uiso 1 1 calc R . .
C14B C -0.1282(3) 0.74453(17) 0.83730(12) 0.0393(5) Uani 1 1 d . . .
H14B H -0.1622 0.6772 0.8441 0.047 Uiso 1 1 calc R . .
C15A C -0.5004(5) 0.9566(2) 0.63202(17) 0.0625(7) Uani 1 1 d . . .
H15A H -0.4936 1.014 0.6486 0.075 Uiso 1 1 calc R . .
C15B C -0.2775(4) 0.81445(18) 0.85537(14) 0.0473(6) Uani 1 1 d . . .
H15B H -0.4104 0.7945 0.8746 0.057 Uiso 1 1 calc R . .
C16A C -0.6648(4) 0.95033(19) 0.59220(16) 0.0546(7) Uani 1 1 d . . .
C16B C -0.2269(5) 0.9138(2) 0.84457(17) 0.0597(7) Uani 1 1 d . . .
C17A C -0.6762(4) 0.8666(2) 0.56753(16) 0.0601(7) Uani 1 1 d . . .
H17A H -0.7875 0.8632 0.54 0.072 Uiso 1 1 calc R . .
C17B C -0.0320(5) 0.9445(2) 0.81614(19) 0.0711(9) Uani 1 1 d . . .
H17B H -0.0002 1.0124 0.8085 0.085 Uiso 1 1 calc R . .
C18A C -0.5206(4) 0.7866(2) 0.58387(15) 0.0541(6) Uani 1 1 d . . .
H18A H -0.5292 0.7289 0.5677 0.065 Uiso 1 1 calc R . .
C18B C 0.1169(4) 0.87322(19) 0.79897(16) 0.0575(7) Uani 1 1 d . . .
H18B H 0.2499 0.8936 0.7802 0.069 Uiso 1 1 calc R . .
N1A N -0.1770(3) 0.48093(15) 0.58284(10) 0.0434(5) Uani 1 1 d . . .
H1A H -0.1378 0.4453 0.5524 0.052 Uiso 1 1 calc R . .
N1B N 0.3284(3) 0.46005(14) 0.93760(10) 0.0405(4) Uani 1 1 d . . .
H1B H 0.3869 0.4241 0.9781 0.049 Uiso 1 1 calc R . .
N3A N -0.2147(3) 0.61041(14) 0.63125(10) 0.0401(4) Uani 1 1 d . . .
N3B N 0.2339(3) 0.59297(13) 0.84148(10) 0.0338(4) Uani 1 1 d . . .
O1A O 0.0095(3) 0.62368(13) 0.52534(10) 0.0538(5) Uani 1 1 d . . .
O1B O 0.4553(3) 0.61792(12) 0.92430(9) 0.0463(4) Uani 1 1 d . . .
O2A O -0.4307(3) 0.54520(15) 0.73630(10) 0.0608(5) Uani 1 1 d . . .
O2B O 0.0467(3) 0.51567(14) 0.77762(10) 0.0587(5) Uani 1 1 d . . .
Cl1A Cl -0.86238(14) 1.05053(7) 0.57453(6) 0.0906(3) Uani 1 1 d . . .
Cl1B Cl -0.41467(17) 1.00126(7) 0.86916(7) 0.1099(4) Uani 1 1 d . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2A O1A 1.224(3) . ?
C2A N1A 1.330(3) . ?
C2A N3A 1.395(3) . ?
C2B O1B 1.222(3) . ?
C2B N1B 1.336(3) . ?
C2B N3B 1.392(3) . ?
C4A O2A 1.207(3) . ?
C4A N3A 1.368(3) . ?
C4A C5A 1.523(3) . ?
C4B O2B 1.207(3) . ?
C4B N3B 1.365(3) . ?
C4B C5B 1.523(3) . ?
C5A N1A 1.454(3) . ?
C5A C6A 1.530(3) . ?
C5A C11A 1.531(3) . ?
C5B N1B 1.458(3) . ?
C5B C11B 1.528(3) . ?
C5B C6B 1.545(3) . ?
C6A C7A 1.516(4) . ?
C6A H6A1 0.97 . ?
C6A H6A2 0.97 . ?
C6B C7B 1.492(4) . ?
C6B H6B1 0.97 . ?
C6B H6B2 0.97 . ?
C7A C8A 1.448(5) . ?
C7A H7A1 0.97 . ?
C7A H7A2 0.97 . ?
C7B C8B 1.520(4) . ?
C7B H7B1 0.97 . ?
C7B H7B2 0.97 . ?
C8A C9A 1.434(5) . ?
C8A H8A1 0.97 . ?
C8A H8A2 0.97 . ?
C8B C9B 1.512(4) . ?
C8B H8B1 0.97 . ?
C8B H8B2 0.97 . ?
C9A C10A 1.466(5) . ?
C9A H9A1 0.97 . ?
C9A H9A2 0.97 . ?
C9B C10B 1.526(4) . ?
C9B H9B1 0.97 . ?
C9B H9B2 0.97 . ?
C10A C11A 1.507(4) . ?
C10A H10A 0.97 . ?
C10A H10B 0.97 . ?
C10B C11B 1.510(4) . ?
C10B H10C 0.97 . ?
C10B H10D 0.97 . ?
C11A H11A 0.97 . ?
C11A H11B 0.97 . ?
C11B H11C 0.97 . ?
C11B H11D 0.97 . ?
C12A N3A 1.449(3) . ?
C12A C13A 1.508(3) . ?
C12A H12A 0.97 . ?
C12A H12B 0.97 . ?
C12B N3B 1.457(3) . ?
C12B C13B 1.507(3) . ?
C12B H12C 0.97 . ?
C12B H12D 0.97 . ?
C13A C14A 1.375(3) . ?
C13A C18A 1.382(3) . ?
C13B C18B 1.381(3) . ?
C13B C14B 1.387(3) . ?
C14A C15A 1.376(4) . ?
C14A H14A 0.93 . ?
C14B C15B 1.379(3) . ?
C14B H14B 0.93 . ?
C15A C16A 1.369(4) . ?
C15A H15A 0.93 . ?
C15B C16B 1.370(4) . ?
C15B H15B 0.93 . ?
C16A C17A 1.362(4) . ?
C16A Cl1A 1.744(3) . ?
C16B C17B 1.369(4) . ?
C16B Cl1B 1.744(3) . ?
C17A C18A 1.384(4) . ?
C17A H17A 0.93 . ?
C17B C18B 1.384(4) . ?
C17B H17B 0.93 . ?
C18A H18A 0.93 . ?
C18B H18B 0.93 . ?
N1A H1A 0.86 . ?
N1B H1B 0.86 . ?

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
O1A C2A N1A 128.8(2) . . ?
O1A C2A N3A 123.8(2) . . ?
N1A C2A N3A 107.42(19) . . ?
O1B C2B N1B 128.5(2) . . ?
O1B C2B N3B 124.0(2) . . ?
N1B C2B N3B 107.41(19) . . ?
O2A C4A N3A 125.5(2) . . ?
O2A C4A C5A 127.2(2) . . ?
N3A C4A C5A 107.27(17) . . ?
O2B C4B N3B 125.7(2) . . ?
O2B C4B C5B 127.1(2) . . ?
N3B C4B C5B 107.23(18) . . ?
N1A C5A C4A 100.46(17) . . ?
N1A C5A C6A 111.18(18) . . ?
C4A C5A C6A 108.81(19) . . ?
N1A C5A C11A 112.25(19) . . ?
C4A C5A C11A 108.00(19) . . ?
C6A C5A C11A 115.0(2) . . ?
N1B C5B C4B 100.47(17) . . ?
N1B C5B C11B 112.19(17) . . ?
C4B C5B C11B 108.97(18) . . ?
N1B C5B C6B 109.42(17) . . ?
C4B C5B C6B 110.71(18) . . ?
C11B C5B C6B 114.23(19) . . ?
C7A C6A C5A 116.3(2) . . ?
C7A C6A H6A1 108.2 . . ?
C5A C6A H6A1 108.2 . . ?
C7A C6A H6A2 108.2 . . ?
C5A C6A H6A2 108.2 . . ?
H6A1 C6A H6A2 107.4 . . ?
C7B C6B C5B 117.8(2) . . ?
C7B C6B H6B1 107.9 . . ?
C5B C6B H6B1 107.9 . . ?
C7B C6B H6B2 107.9 . . ?
C5B C6B H6B2 107.9 . . ?
H6B1 C6B H6B2 107.2 . . ?
C8A C7A C6A 119.2(3) . . ?
C8A C7A H7A1 107.5 . . ?
C6A C7A H7A1 107.5 . . ?
C8A C7A H7A2 107.5 . . ?
C6A C7A H7A2 107.5 . . ?
H7A1 C7A H7A2 107 . . ?
C6B C7B C8B 115.6(2) . . ?
C6B C7B H7B1 108.4 . . ?
C8B C7B H7B1 108.4 . . ?
C6B C7B H7B2 108.4 . . ?
C8B C7B H7B2 108.4 . . ?
H7B1 C7B H7B2 107.4 . . ?
C9A C8A C7A 125.3(3) . . ?
C9A C8A H8A1 106 . . ?
C7A C8A H8A1 106 . . ?
C9A C8A H8A2 106 . . ?
C7A C8A H8A2 106 . . ?
H8A1 C8A H8A2 106.3 . . ?
C9B C8B C7B 116.5(3) . . ?
C9B C8B H8B1 108.2 . . ?
C7B C8B H8B1 108.2 . . ?
C9B C8B H8B2 108.2 . . ?
C7B C8B H8B2 108.2 . . ?
H8B1 C8B H8B2 107.3 . . ?
C8A C9A C10A 121.4(4) . . ?
C8A C9A H9A1 107 . . ?
C10A C9A H9A1 107 . . ?
C8A C9A H9A2 107 . . ?
C10A C9A H9A2 107 . . ?
H9A1 C9A H9A2 106.7 . . ?
C8B C9B C10B 115.4(2) . . ?
C8B C9B H9B1 108.4 . . ?
C10B C9B H9B1 108.4 . . ?
C8B C9B H9B2 108.4 . . ?
C10B C9B H9B2 108.4 . . ?
H9B1 C9B H9B2 107.5 . . ?
C9A C10A C11A 116.9(3) . . ?
C9A C10A H10A 108.1 . . ?
C11A C10A H10A 108.1 . . ?
C9A C10A H10B 108.1 . . ?
C11A C10A H10B 108.1 . . ?
H10A C10A H10B 107.3 . . ?
C11B C10B C9B 113.8(2) . . ?
C11B C10B H10C 108.8 . . ?
C9B C10B H10C 108.8 . . ?
C11B C10B H10D 108.8 . . ?
C9B C10B H10D 108.8 . . ?
H10C C10B H10D 107.7 . . ?
C10A C11A C5A 116.1(2) . . ?
C10A C11A H11A 108.3 . . ?
C5A C11A H11A 108.3 . . ?
C10A C11A H11B 108.3 . . ?
C5A C11A H11B 108.3 . . ?
H11A C11A H11B 107.4 . . ?
C10B C11B C5B 116.6(2) . . ?
C10B C11B H11C 108.1 . . ?
C5B C11B H11C 108.1 . . ?
C10B C11B H11D 108.1 . . ?
C5B C11B H11D 108.1 . . ?
H11C C11B H11D 107.3 . . ?
N3A C12A C13A 115.2(2) . . ?
N3A C12A H12A 108.5 . . ?
C13A C12A H12A 108.5 . . ?
N3A C12A H12B 108.5 . . ?
C13A C12A H12B 108.5 . . ?
H12A C12A H12B 107.5 . . ?
N3B C12B C13B 113.12(17) . . ?
N3B C12B H12C 109 . . ?
C13B C12B H12C 109 . . ?
N3B C12B H12D 109 . . ?
C13B C12B H12D 109 . . ?
H12C C12B H12D 107.8 . . ?
C14A C13A C18A 118.1(2) . . ?
C14A C13A C12A 118.0(2) . . ?
C18A C13A C12A 123.9(2) . . ?
C18B C13B C14B 118.0(2) . . ?
C18B C13B C12B 120.2(2) . . ?
C14B C13B C12B 121.8(2) . . ?
C13A C14A C15A 121.3(3) . . ?
C13A C14A H14A 119.3 . . ?
C15A C14A H14A 119.3 . . ?
C15B C14B C13B 121.4(2) . . ?
C15B C14B H14B 119.3 . . ?
C13B C14B H14B 119.3 . . ?
C16A C15A C14A 119.5(2) . . ?
C16A C15A H15A 120.3 . . ?
C14A C15A H15A 120.3 . . ?
C16B C15B C14B 119.0(2) . . ?
C16B C15B H15B 120.5 . . ?
C14B C15B H15B 120.5 . . ?
C17A C16A C15A 120.8(3) . . ?
C17A C16A Cl1A 120.3(2) . . ?
C15A C16A Cl1A 119.0(2) . . ?
C17B C16B C15B 121.3(2) . . ?
C17B C16B Cl1B 120.0(2) . . ?
C15B C16B Cl1B 118.8(2) . . ?
C16A C17A C18A 119.4(3) . . ?
C16A C17A H17A 120.3 . . ?
C18A C17A H17A 120.3 . . ?
C16B C17B C18B 119.2(2) . . ?
C16B C17B H17B 120.4 . . ?
C18B C17B H17B 120.4 . . ?
C13A C18A C17A 121.0(2) . . ?
C13A C18A H18A 119.5 . . ?
C17A C18A H18A 119.5 . . ?
C13B C18B C17B 121.2(2) . . ?
C13B C18B H18B 119.4 . . ?
C17B C18B H18B 119.4 . . ?
C2A N1A C5A 113.57(17) . . ?
C2A N1A H1A 123.2 . . ?
C5A N1A H1A 123.2 . . ?
C2B N1B C5B 113.19(18) . . ?
C2B N1B H1B 123.4 . . ?
C5B N1B H1B 123.4 . . ?
C4A N3A C2A 111.14(18) . . ?
C4A N3A C12A 124.27(19) . . ?
C2A N3A C12A 124.10(19) . . ?
C4B N3B C2B 111.40(18) . . ?
C4B N3B C12B 125.00(18) . . ?
C2B N3B C12B 122.94(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2A C4A C5A N1A -178.8(2) . . . . ?
N3A C4A C5A N1A 1.9(2) . . . . ?
O2A C4A C5A C6A -62.0(3) . . . . ?
N3A C4A C5A C6A 118.8(2) . . . . ?
O2A C4A C5A C11A 63.5(3) . . . . ?
N3A C4A C5A C11A -115.8(2) . . . . ?
O2B C4B C5B N1B 175.7(2) . . . . ?
N3B C4B C5B N1B -4.8(2) . . . . ?
O2B C4B C5B C11B 57.7(3) . . . . ?
N3B C4B C5B C11B -122.85(18) . . . . ?
O2B C4B C5B C6B -68.7(3) . . . . ?
N3B C4B C5B C6B 110.72(19) . . . . ?
N1A C5A C6A C7A -58.0(3) . . . . ?
C4A C5A C6A C7A -167.8(2) . . . . ?
C11A C5A C6A C7A 70.9(3) . . . . ?
N1B C5B C6B C7B -160.2(2) . . . . ?
C4B C5B C6B C7B 90.0(3) . . . . ?
C11B C5B C6B C7B -33.5(3) . . . . ?
C5A C6A C7A C8A -68.8(4) . . . . ?
C5B C6B C7B C8B 83.2(3) . . . . ?
C6A C7A C8A C9A 25.7(8) . . . . ?
C6B C7B C8B C9B -70.1(4) . . . . ?
C7A C8A C9A C10A 35.8(9) . . . . ?
C7B C8B C9B C10B 51.8(4) . . . . ?
C8A C9A C10A C11A -71.2(6) . . . . ?
C8B C9B C10B C11B -69.5(4) . . . . ?
C9A C10A C11A C5A 67.1(4) . . . . ?
N1A C5A C11A C10A 67.4(3) . . . . ?
C4A C5A C11A C10A 177.2(2) . . . . ?
C6A C5A C11A C10A -61.1(3) . . . . ?
C9B C10B C11B C5B 88.4(3) . . . . ?
N1B C5B C11B C10B 82.0(3) . . . . ?
C4B C5B C11B C10B -167.7(2) . . . . ?
C6B C5B C11B C10B -43.3(3) . . . . ?
N3A C12A C13A C14A 167.7(2) . . . . ?
N3A C12A C13A C18A -12.3(3) . . . . ?
N3B C12B C13B C18B 141.1(2) . . . . ?
N3B C12B C13B C14B -40.6(3) . . . . ?
C18A C13A C14A C15A 0.4(4) . . . . ?
C12A C13A C14A C15A -179.6(2) . . . . ?
C18B C13B C14B C15B -0.7(3) . . . . ?
C12B C13B C14B C15B -179.0(2) . . . . ?
C13A C14A C15A C16A -0.6(4) . . . . ?
C13B C14B C15B C16B 0.6(4) . . . . ?
C14A C15A C16A C17A 0.0(4) . . . . ?
C14A C15A C16A Cl1A 179.0(2) . . . . ?
C14B C15B C16B C17B 0.2(4) . . . . ?
C14B C15B C16B Cl1B -178.8(2) . . . . ?
C15A C16A C17A C18A 0.8(4) . . . . ?
Cl1A C16A C17A C18A -178.3(2) . . . . ?
C15B C16B C17B C18B -0.8(5) . . . . ?
Cl1B C16B C17B C18B 178.2(2) . . . . ?
C14A C13A C18A C17A 0.3(4) . . . . ?
C12A C13A C18A C17A -179.7(2) . . . . ?
C16A C17A C18A C13A -0.9(4) . . . . ?
C14B C13B C18B C17B 0.0(4) . . . . ?
C12B C13B C18B C17B 178.4(3) . . . . ?
C16B C17B C18B C13B 0.8(5) . . . . ?
O1A C2A N1A C5A 177.5(2) . . . . ?
N3A C2A N1A C5A -2.5(3) . . . . ?
C4A C5A N1A C2A 0.4(2) . . . . ?
C6A C5A N1A C2A -114.7(2) . . . . ?
C11A C5A N1A C2A 114.9(2) . . . . ?
O1B C2B N1B C5B -179.7(2) . . . . ?
N3B C2B N1B C5B 0.6(2) . . . . ?
C4B C5B N1B C2B 2.6(2) . . . . ?
C11B C5B N1B C2B 118.2(2) . . . . ?
C6B C5B N1B C2B -113.9(2) . . . . ?
O2A C4A N3A C2A 177.1(2) . . . . ?
C5A C4A N3A C2A -3.6(3) . . . . ?
O2A C4A N3A C12A 4.8(4) . . . . ?
C5A C4A N3A C12A -175.9(2) . . . . ?
O1A C2A N3A C4A -176.1(2) . . . . ?
N1A C2A N3A C4A 3.8(3) . . . . ?
O1A C2A N3A C12A -3.8(4) . . . . ?
N1A C2A N3A C12A 176.2(2) . . . . ?
C13A C12A N3A C4A -79.9(3) . . . . ?
C13A C12A N3A C2A 108.8(3) . . . . ?
O2B C4B N3B C2B -174.9(2) . . . . ?
C5B C4B N3B C2B 5.7(2) . . . . ?
O2B C4B N3B C12B -4.0(3) . . . . ?
C5B C4B N3B C12B 176.54(17) . . . . ?
O1B C2B N3B C4B 176.21(19) . . . . ?
N1B C2B N3B C4B -4.1(2) . . . . ?
O1B C2B N3B C12B 5.1(3) . . . . ?
N1B C2B N3B C12B -175.15(17) . . . . ?
C13B C12B N3B C4B 100.9(2) . . . . ?
C13B C12B N3B C2B -89.2(2) . . . . ?
####################################################################### 
# 
# 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_5-7br_1733_smart
_database_code_depnum_ccdc_archive 'CCDC 1509617'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_publcif_datablock.id            {28d6bb54-71fa-4d93-97e5-c7ddab7fc7c9}

_audit_creation_date             2016-10-09T09:56:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16 H19 Br N2 O2'
_chemical_formula_weight         351.23

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

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

_cell_length_a                   6.4576(13)
_cell_length_b                   13.713(3)
_cell_length_c                   18.624(4)
_cell_angle_alpha                72.03(3)
_cell_angle_beta                 84.97(3)
_cell_angle_gamma                84.93(3)
_cell_volume                     1559.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2635
_cell_measurement_theta_min      3.7160
_cell_measurement_theta_max      26.1890
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6585
_exptl_crystal_size_mid          0.1402
_exptl_crystal_size_min          0.0971
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720

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

_exptl_absorpt_coefficient_mu    2.642
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.430
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0.0
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_number            11272
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.989
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             5709
_reflns_number_gt                4135
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_molecular_graphics    MERCURY
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+0.5245P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5709
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.069
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.083

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
C6A C 1.0104(5) 0.1129(3) 0.0523(2) 0.0495(8) Uani 1 1 d . . . . .
H1A H 1.0987 0.0509 0.0555 0.059 Uiso 1 1 calc R U . . .
H1B H 0.973 0.1414 0.0003 0.059 Uiso 1 1 calc R U . . .
C7A C 1.1382(5) 0.1884(3) 0.0695(2) 0.0618(10) Uani 1 1 d . . . . .
H2A H 1.2811 0.1786 0.0508 0.074 Uiso 1 1 calc R U . . .
H2B H 1.1377 0.1729 0.124 0.074 Uiso 1 1 calc R U . . .
C8A C 1.0660(6) 0.3008(3) 0.0362(3) 0.0699(11) Uani 1 1 d . . . . .
H3A H 1.1747 0.3424 0.0412 0.084 Uiso 1 1 calc R U . . .
H3B H 1.0518 0.3141 -0.0174 0.084 Uiso 1 1 calc R U . . .
C9A C 0.8646(6) 0.3370(3) 0.0700(3) 0.0738(12) Uani 1 1 d . . . . .
H4A H 0.8287 0.4073 0.0404 0.089 Uiso 1 1 calc R U . . .
H4B H 0.8865 0.3374 0.1208 0.089 Uiso 1 1 calc R U . . .
C10A C 0.6791(6) 0.2723(3) 0.0739(2) 0.0605(10) Uani 1 1 d . . . . .
H5A H 0.5527 0.3084 0.087 0.073 Uiso 1 1 calc R U . . .
H5B H 0.6662 0.2654 0.0242 0.073 Uiso 1 1 calc R U . . .
C11A C 0.6974(5) 0.1667(2) 0.1303(2) 0.0462(8) Uani 1 1 d . . . . .
H6A H 0.5581 0.1464 0.1493 0.055 Uiso 1 1 calc R U . . .
H6B H 0.7692 0.1712 0.1727 0.055 Uiso 1 1 calc R U . . .
C5A C 0.8098(4) 0.0818(2) 0.10207(17) 0.0366(7) Uani 1 1 d . . . . .
C4A C 0.8550(4) -0.0122(2) 0.16942(17) 0.0386(7) Uani 1 1 d . . . . .
C2A C 0.6473(4) -0.0604(2) 0.09535(16) 0.0357(7) Uani 1 1 d . . . . .
C12A C 0.7620(5) -0.1956(2) 0.21231(17) 0.0412(7) Uani 1 1 d . . . . .
H10A H 0.6253 -0.221 0.2148 0.049 Uiso 1 1 calc R U . . .
H10B H 0.786 -0.1923 0.2622 0.049 Uiso 1 1 calc R U . . .
C13A C 0.9243(5) -0.2701(2) 0.19119(16) 0.0373(7) Uani 1 1 d . . . . .
C14A C 1.1226(5) -0.2417(2) 0.16299(17) 0.0401(7) Uani 1 1 d . . . . .
H12 H 1.1566 -0.1748 0.156 0.048 Uiso 1 1 calc R U . . .
C15A C 1.2715(5) -0.3108(3) 0.14494(19) 0.0479(8) Uani 1 1 d . . . . .
H13 H 1.4042 -0.2908 0.1258 0.058 Uiso 1 1 calc R U . . .
C16A C 1.2194(6) -0.4093(3) 0.1558(2) 0.0561(9) Uani 1 1 d . . . . .
C17A C 1.0248(7) -0.4398(3) 0.1846(3) 0.0662(11) Uani 1 1 d . . . . .
H15 H 0.992 -0.5071 0.1923 0.079 Uiso 1 1 calc R U . . .
C18A C 0.8783(6) -0.3701(3) 0.2019(2) 0.0549(9) Uani 1 1 d . . . . .
H16 H 0.746 -0.3907 0.2212 0.066 Uiso 1 1 calc R U . . .
C6B C 1.5391(5) 0.0688(3) 0.3711(2) 0.0568(9) Uani 1 1 d . . . . .
H17A H 1.5905 0.0043 0.4057 0.068 Uiso 1 1 calc R U . . .
H17B H 1.6305 0.0825 0.3254 0.068 Uiso 1 1 calc R U . . .
C7B C 1.5560(7) 0.1528(4) 0.4066(3) 0.0815(14) Uani 1 1 d . . . . .
H18A H 1.4613 0.1403 0.4514 0.098 Uiso 1 1 calc R U . . .
H18B H 1.6961 0.1476 0.423 0.098 Uiso 1 1 calc R U . . .
C8B C 1.5114(10) 0.2575(4) 0.3589(5) 0.133(3) Uani 1 1 d . . . . .
H19A H 1.5622 0.3026 0.3837 0.16 Uiso 1 1 calc R U . . .
H19B H 1.5971 0.2658 0.3122 0.16 Uiso 1 1 calc R U . . .
C9B C 1.3078(10) 0.2968(4) 0.3382(5) 0.132(3) Uani 1 1 d . . . . .
H20A H 1.3251 0.3581 0.2954 0.158 Uiso 1 1 calc R U . . .
H20B H 1.2436 0.3199 0.3796 0.158 Uiso 1 1 calc R U . . .
C10B C 1.1523(6) 0.2408(3) 0.3183(3) 0.0676(11) Uani 1 1 d . . . . .
H21A H 1.0747 0.2891 0.2786 0.081 Uiso 1 1 calc R U . . .
H21B H 1.0554 0.2183 0.3621 0.081 Uiso 1 1 calc R U . . .
C11B C 1.2225(6) 0.1481(3) 0.29220(19) 0.0504(8) Uani 1 1 d . . . . .
H22A H 1.3229 0.1695 0.2494 0.061 Uiso 1 1 calc R U . . .
H22B H 1.103 0.1265 0.2743 0.061 Uiso 1 1 calc R U . . .
C5B C 1.3201(5) 0.0551(2) 0.35076(17) 0.0392(7) Uani 1 1 d . . . . .
C4B C 1.3337(5) -0.0368(3) 0.32021(18) 0.0434(7) Uani 1 1 d . . . . .
C2B C 1.1152(5) -0.0746(2) 0.42685(17) 0.0406(7) Uani 1 1 d . . . . .
C12B C 1.1745(5) -0.2055(3) 0.3569(2) 0.0484(8) Uani 1 1 d . . . . .
H26A H 1.1464 -0.191 0.3042 0.058 Uiso 1 1 calc R U . . .
H26B H 1.0496 -0.2312 0.3872 0.058 Uiso 1 1 calc R U . . .
C13B C 1.3473(5) -0.2885(2) 0.37538(17) 0.0393(7) Uani 1 1 d . . . . .
C14B C 1.5164(6) -0.2851(3) 0.4142(2) 0.0536(9) Uani 1 1 d . . . . .
H28 H 1.5279 -0.2286 0.4308 0.064 Uiso 1 1 calc R U . . .
C15B C 1.6705(6) -0.3647(3) 0.4291(2) 0.0564(9) Uani 1 1 d . . . . .
H29 H 1.7847 -0.3613 0.4552 0.068 Uiso 1 1 calc R U . . .
C16B C 1.6532(5) -0.4481(2) 0.4052(2) 0.0491(8) Uani 1 1 d . . . . .
C17B C 1.4859(6) -0.4531(3) 0.3662(2) 0.0562(9) Uani 1 1 d . . . . .
H31 H 1.4751 -0.5098 0.3496 0.067 Uiso 1 1 calc R U . . .
C18B C 1.3342(5) -0.3738(2) 0.3517(2) 0.0491(8) Uani 1 1 d . . . . .
H32 H 1.2207 -0.3776 0.3254 0.059 Uiso 1 1 calc R U . . .
N1A N 0.6736(4) 0.03931(19) 0.06205(14) 0.0422(6) Uani 1 1 d . . . . .
H1A1 H 0.6165 0.0749 0.0213 0.051 Uiso 1 1 calc R U . . .
N3A N 0.7644(4) -0.09263(18) 0.15896(13) 0.0354(6) Uani 1 1 d . . . . .
N1B N 1.1794(4) 0.0187(2) 0.41760(14) 0.0448(6) Uani 1 1 d . . . . .
H1B1 H 1.1415 0.0539 0.4481 0.054 Uiso 1 1 calc R U . . .
N3B N 1.2155(4) -0.11016(19) 0.36964(14) 0.0411(6) Uani 1 1 d . . . . .
O2A O 0.9538(4) -0.01650(19) 0.22240(14) 0.0595(7) Uani 1 1 d . . . . .
O1A O 0.5428(4) -0.11680(17) 0.07586(12) 0.0472(5) Uani 1 1 d . . . . .
O2B O 1.4309(4) -0.0449(2) 0.26400(14) 0.0628(7) Uani 1 1 d . . . . .
O1B O 0.9917(4) -0.12310(18) 0.47499(14) 0.0559(6) Uani 1 1 d . . . . .
Br1A Br 1.42282(9) -0.50257(4) 0.12831(4) 0.1023(2) Uani 1 1 d . . . . .
Br1B Br 1.86485(7) -0.55653(3) 0.42277(3) 0.07792(19) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6A C7A 1.503(5) . ?
C6A C5A 1.537(4) . ?
C6A H1A 0.97 . ?
C6A H1B 0.97 . ?
C7A C8A 1.520(6) . ?
C7A H2A 0.97 . ?
C7A H2B 0.97 . ?
C8A C9A 1.507(6) . ?
C8A H3A 0.97 . ?
C8A H3B 0.97 . ?
C9A C10A 1.537(5) . ?
C9A H4A 0.97 . ?
C9A H4B 0.97 . ?
C10A C11A 1.505(5) . ?
C10A H5A 0.97 . ?
C10A H5B 0.97 . ?
C11A C5A 1.522(4) . ?
C11A H6A 0.97 . ?
C11A H6B 0.97 . ?
C5A N1A 1.463(4) . ?
C5A C4A 1.523(4) . ?
C4A O2A 1.205(4) . ?
C4A N3A 1.365(4) . ?
C2A O1A 1.222(3) . ?
C2A N1A 1.335(4) . ?
C2A N3A 1.395(4) . ?
C12A N3A 1.455(4) . ?
C12A C13A 1.511(4) . ?
C12A H10A 0.97 . ?
C12A H10B 0.97 . ?
C13A C18A 1.378(5) . ?
C13A C14A 1.383(4) . ?
C14A C15A 1.383(4) . ?
C14A H12 0.93 . ?
C15A C16A 1.371(5) . ?
C15A H13 0.93 . ?
C16A C17A 1.370(5) . ?
C16A Br1A 1.900(4) . ?
C17A C18A 1.375(5) . ?
C17A H15 0.93 . ?
C18A H16 0.93 . ?
C6B C7B 1.510(6) . ?
C6B C5B 1.538(4) . ?
C6B H17A 0.97 . ?
C6B H17B 0.97 . ?
C7B C8B 1.456(7) . ?
C7B H18A 0.97 . ?
C7B H18B 0.97 . ?
C8B C9B 1.415(8) . ?
C8B H19A 0.97 . ?
C8B H19B 0.97 . ?
C9B C10B 1.453(6) . ?
C9B H20A 0.97 . ?
C9B H20B 0.97 . ?
C10B C11B 1.516(5) . ?
C10B H21A 0.97 . ?
C10B H21B 0.97 . ?
C11B C5B 1.528(5) . ?
C11B H22A 0.97 . ?
C11B H22B 0.97 . ?
C5B N1B 1.457(4) . ?
C5B C4B 1.527(4) . ?
C4B O2B 1.203(4) . ?
C4B N3B 1.373(4) . ?
C2B O1B 1.218(4) . ?
C2B N1B 1.335(4) . ?
C2B N3B 1.392(4) . ?
C12B N3B 1.448(4) . ?
C12B C13B 1.504(5) . ?
C12B H26A 0.97 . ?
C12B H26B 0.97 . ?
C13B C14B 1.374(5) . ?
C13B C18B 1.383(4) . ?
C14B C15B 1.389(5) . ?
C14B H28 0.93 . ?
C15B C16B 1.366(5) . ?
C15B H29 0.93 . ?
C16B C17B 1.371(5) . ?
C16B Br1B 1.898(3) . ?
C17B C18B 1.376(5) . ?
C17B H31 0.93 . ?
C18B H32 0.93 . ?
N1A H1A1 0.86 . ?
N1B H1B1 0.86 . ?

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
C7A C6A C5A 117.8(3) . . ?
C7A C6A H1A 107.8 . . ?
C5A C6A H1A 107.8 . . ?
C7A C6A H1B 107.8 . . ?
C5A C6A H1B 107.8 . . ?
H1A C6A H1B 107.2 . . ?
C6A C7A C8A 115.4(3) . . ?
C6A C7A H2A 108.4 . . ?
C8A C7A H2A 108.4 . . ?
C6A C7A H2B 108.4 . . ?
C8A C7A H2B 108.4 . . ?
H2A C7A H2B 107.5 . . ?
C9A C8A C7A 116.8(3) . . ?
C9A C8A H3A 108.1 . . ?
C7A C8A H3A 108.1 . . ?
C9A C8A H3B 108.1 . . ?
C7A C8A H3B 108.1 . . ?
H3A C8A H3B 107.3 . . ?
C8A C9A C10A 114.9(3) . . ?
C8A C9A H4A 108.5 . . ?
C10A C9A H4A 108.5 . . ?
C8A C9A H4B 108.5 . . ?
C10A C9A H4B 108.5 . . ?
H4A C9A H4B 107.5 . . ?
C11A C10A C9A 113.9(3) . . ?
C11A C10A H5A 108.8 . . ?
C9A C10A H5A 108.8 . . ?
C11A C10A H5B 108.8 . . ?
C9A C10A H5B 108.8 . . ?
H5A C10A H5B 107.7 . . ?
C10A C11A C5A 116.8(3) . . ?
C10A C11A H6A 108.1 . . ?
C5A C11A H6A 108.1 . . ?
C10A C11A H6B 108.1 . . ?
C5A C11A H6B 108.1 . . ?
H6A C11A H6B 107.3 . . ?
N1A C5A C11A 112.2(2) . . ?
N1A C5A C4A 100.3(2) . . ?
C11A C5A C4A 109.3(3) . . ?
N1A C5A C6A 109.2(2) . . ?
C11A C5A C6A 114.5(3) . . ?
C4A C5A C6A 110.4(3) . . ?
O2A C4A N3A 125.4(3) . . ?
O2A C4A C5A 127.1(3) . . ?
N3A C4A C5A 107.5(2) . . ?
O1A C2A N1A 128.4(3) . . ?
O1A C2A N3A 123.9(3) . . ?
N1A C2A N3A 107.6(2) . . ?
N3A C12A C13A 112.9(2) . . ?
N3A C12A H10A 109 . . ?
C13A C12A H10A 109 . . ?
N3A C12A H10B 109 . . ?
C13A C12A H10B 109 . . ?
H10A C12A H10B 107.8 . . ?
C18A C13A C14A 118.3(3) . . ?
C18A C13A C12A 120.0(3) . . ?
C14A C13A C12A 121.6(3) . . ?
C13A C14A C15A 121.4(3) . . ?
C13A C14A H12 119.3 . . ?
C15A C14A H12 119.3 . . ?
C16A C15A C14A 118.7(3) . . ?
C16A C15A H13 120.7 . . ?
C14A C15A H13 120.7 . . ?
C17A C16A C15A 121.1(3) . . ?
C17A C16A Br1A 120.6(3) . . ?
C15A C16A Br1A 118.3(3) . . ?
C16A C17A C18A 119.6(3) . . ?
C16A C17A H15 120.2 . . ?
C18A C17A H15 120.2 . . ?
C17A C18A C13A 121.0(3) . . ?
C17A C18A H16 119.5 . . ?
C13A C18A H16 119.5 . . ?
C7B C6B C5B 116.2(3) . . ?
C7B C6B H17A 108.2 . . ?
C5B C6B H17A 108.2 . . ?
C7B C6B H17B 108.2 . . ?
C5B C6B H17B 108.2 . . ?
H17A C6B H17B 107.4 . . ?
C8B C7B C6B 116.2(4) . . ?
C8B C7B H18A 108.2 . . ?
C6B C7B H18A 108.2 . . ?
C8B C7B H18B 108.2 . . ?
C6B C7B H18B 108.2 . . ?
H18A C7B H18B 107.4 . . ?
C9B C8B C7B 122.5(5) . . ?
C9B C8B H19A 106.7 . . ?
C7B C8B H19A 106.7 . . ?
C9B C8B H19B 106.7 . . ?
C7B C8B H19B 106.7 . . ?
H19A C8B H19B 106.6 . . ?
C8B C9B C10B 125.7(5) . . ?
C8B C9B H20A 105.9 . . ?
C10B C9B H20A 105.9 . . ?
C8B C9B H20B 105.9 . . ?
C10B C9B H20B 105.9 . . ?
H20A C9B H20B 106.2 . . ?
C9B C10B C11B 119.1(4) . . ?
C9B C10B H21A 107.6 . . ?
C11B C10B H21A 107.6 . . ?
C9B C10B H21B 107.6 . . ?
C11B C10B H21B 107.6 . . ?
H21A C10B H21B 107 . . ?
C10B C11B C5B 116.6(3) . . ?
C10B C11B H22A 108.2 . . ?
C5B C11B H22A 108.2 . . ?
C10B C11B H22B 108.2 . . ?
C5B C11B H22B 108.2 . . ?
H22A C11B H22B 107.3 . . ?
N1B C5B C4B 100.5(2) . . ?
N1B C5B C11B 111.6(3) . . ?
C4B C5B C11B 108.5(3) . . ?
N1B C5B C6B 112.2(3) . . ?
C4B C5B C6B 108.2(3) . . ?
C11B C5B C6B 114.8(3) . . ?
O2B C4B N3B 125.8(3) . . ?
O2B C4B C5B 127.1(3) . . ?
N3B C4B C5B 107.1(3) . . ?
O1B C2B N1B 128.7(3) . . ?
O1B C2B N3B 123.7(3) . . ?
N1B C2B N3B 107.5(3) . . ?
N3B C12B C13B 115.1(3) . . ?
N3B C12B H26A 108.5 . . ?
C13B C12B H26A 108.5 . . ?
N3B C12B H26B 108.5 . . ?
C13B C12B H26B 108.5 . . ?
H26A C12B H26B 107.5 . . ?
C14B C13B C18B 118.1(3) . . ?
C14B C13B C12B 124.3(3) . . ?
C18B C13B C12B 117.6(3) . . ?
C13B C14B C15B 121.1(3) . . ?
C13B C14B H28 119.5 . . ?
C15B C14B H28 119.4 . . ?
C16B C15B C14B 119.5(3) . . ?
C16B C15B H29 120.2 . . ?
C14B C15B H29 120.2 . . ?
C15B C16B C17B 120.4(3) . . ?
C15B C16B Br1B 120.3(3) . . ?
C17B C16B Br1B 119.2(3) . . ?
C16B C17B C18B 119.6(3) . . ?
C16B C17B H31 120.2 . . ?
C18B C17B H31 120.2 . . ?
C17B C18B C13B 121.2(3) . . ?
C17B C18B H32 119.4 . . ?
C13B C18B H32 119.4 . . ?
C2A N1A C5A 113.1(2) . . ?
C2A N1A H1A1 123.5 . . ?
C5A N1A H1A1 123.5 . . ?
C4A N3A C2A 111.2(2) . . ?
C4A N3A C12A 125.2(2) . . ?
C2A N3A C12A 123.1(2) . . ?
C2B N1B C5B 113.4(2) . . ?
C2B N1B H1B1 123.3 . . ?
C5B N1B H1B1 123.3 . . ?
C4B N3B C2B 111.3(3) . . ?
C4B N3B C12B 123.9(3) . . ?
C2B N3B C12B 124.2(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
C5A C6A C7A C8A -82.7(4) . . . . ?
C6A C7A C8A C9A 70.2(5) . . . . ?
C7A C8A C9A C10A -52.1(6) . . . . ?
C8A C9A C10A C11A 69.4(5) . . . . ?
C9A C10A C11A C5A -88.3(4) . . . . ?
C10A C11A C5A N1A -82.0(3) . . . . ?
C10A C11A C5A C4A 167.7(3) . . . . ?
C10A C11A C5A C6A 43.2(4) . . . . ?
C7A C6A C5A N1A 160.1(3) . . . . ?
C7A C6A C5A C11A 33.4(4) . . . . ?
C7A C6A C5A C4A -90.4(3) . . . . ?
N1A C5A C4A O2A -176.0(3) . . . . ?
C11A C5A C4A O2A -58.0(4) . . . . ?
C6A C5A C4A O2A 68.8(4) . . . . ?
N1A C5A C4A N3A 4.6(3) . . . . ?
C11A C5A C4A N3A 122.6(3) . . . . ?
C6A C5A C4A N3A -110.6(3) . . . . ?
N3A C12A C13A C18A -141.6(3) . . . . ?
N3A C12A C13A C14A 40.3(4) . . . . ?
C18A C13A C14A C15A 0.8(5) . . . . ?
C12A C13A C14A C15A 178.9(3) . . . . ?
C13A C14A C15A C16A -0.3(5) . . . . ?
C14A C15A C16A C17A -0.6(6) . . . . ?
C14A C15A C16A Br1A 178.4(3) . . . . ?
C15A C16A C17A C18A 0.8(6) . . . . ?
Br1A C16A C17A C18A -178.0(3) . . . . ?
C16A C17A C18A C13A -0.3(6) . . . . ?
C14A C13A C18A C17A -0.5(5) . . . . ?
C12A C13A C18A C17A -178.7(3) . . . . ?
C5B C6B C7B C8B -65.8(6) . . . . ?
C6B C7B C8B C9B 71.1(9) . . . . ?
C7B C8B C9B C10B -39.4(13) . . . . ?
C8B C9B C10B C11B -21.4(11) . . . . ?
C9B C10B C11B C5B 66.3(6) . . . . ?
C10B C11B C5B N1B 57.4(4) . . . . ?
C10B C11B C5B C4B 167.1(3) . . . . ?
C10B C11B C5B C6B -71.8(4) . . . . ?
C7B C6B C5B N1B -66.8(4) . . . . ?
C7B C6B C5B C4B -176.7(3) . . . . ?
C7B C6B C5B C11B 62.0(4) . . . . ?
N1B C5B C4B O2B 179.1(3) . . . . ?
C11B C5B C4B O2B 61.9(4) . . . . ?
C6B C5B C4B O2B -63.2(4) . . . . ?
N1B C5B C4B N3B -1.7(3) . . . . ?
C11B C5B C4B N3B -118.9(3) . . . . ?
C6B C5B C4B N3B 116.0(3) . . . . ?
N3B C12B C13B C14B 11.7(5) . . . . ?
N3B C12B C13B C18B -168.4(3) . . . . ?
C18B C13B C14B C15B 0.2(5) . . . . ?
C12B C13B C14B C15B -179.9(3) . . . . ?
C13B C14B C15B C16B -0.4(6) . . . . ?
C14B C15B C16B C17B 0.5(6) . . . . ?
C14B C15B C16B Br1B 178.5(3) . . . . ?
C15B C16B C17B C18B -0.5(6) . . . . ?
Br1B C16B C17B C18B -178.5(3) . . . . ?
C16B C17B C18B C13B 0.3(6) . . . . ?
C14B C13B C18B C17B -0.2(5) . . . . ?
C12B C13B C18B C17B 179.9(3) . . . . ?
O1A C2A N1A C5A 179.6(3) . . . . ?
N3A C2A N1A C5A -0.8(3) . . . . ?
C11A C5A N1A C2A -118.2(3) . . . . ?
C4A C5A N1A C2A -2.3(3) . . . . ?
C6A C5A N1A C2A 113.8(3) . . . . ?
O2A C4A N3A C2A 175.1(3) . . . . ?
C5A C4A N3A C2A -5.5(3) . . . . ?
O2A C4A N3A C12A 3.8(5) . . . . ?
C5A C4A N3A C12A -176.8(3) . . . . ?
O1A C2A N3A C4A -176.3(3) . . . . ?
N1A C2A N3A C4A 4.1(3) . . . . ?
O1A C2A N3A C12A -4.8(4) . . . . ?
N1A C2A N3A C12A 175.6(3) . . . . ?
C13A C12A N3A C4A -100.3(3) . . . . ?
C13A C12A N3A C2A 89.4(3) . . . . ?
O1B C2B N1B C5B -176.6(3) . . . . ?
N3B C2B N1B C5B 3.1(4) . . . . ?
C4B C5B N1B C2B -0.9(3) . . . . ?
C11B C5B N1B C2B 114.0(3) . . . . ?
C6B C5B N1B C2B -115.5(3) . . . . ?
O2B C4B N3B C2B -177.1(3) . . . . ?
C5B C4B N3B C2B 3.7(3) . . . . ?
O2B C4B N3B C12B -6.3(5) . . . . ?
C5B C4B N3B C12B 174.5(3) . . . . ?
O1B C2B N3B C4B 175.4(3) . . . . ?
N1B C2B N3B C4B -4.2(4) . . . . ?
O1B C2B N3B C12B 4.7(5) . . . . ?
N1B C2B N3B C12B -175.0(3) . . . . ?
C13B C12B N3B C4B 80.3(4) . . . . ?
C13B C12B N3B C2B -110.1(3) . . . . ?

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
