# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_v611
_database_code_depnum_ccdc_archive 'CCDC 1885352'
_audit_update_record             
;
2018-12-16 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;

# start Validation Reply
_vrf_PLAT430_v611                
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.89 Ang.  
RESPONSE: Intermolecular head-to-head contact between two carbonyl oxygen
atoms O1...O1 (-x,1-y,1-z) according to topological analysis of calculated
electron density has an attractive nature and belongs to closed
shell interaction. More details in the pubslished article.
;
# end Validation Reply

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(2RS,3RS)-2-bromo-3-hydroxy-1-(4-methylphenyl)-3-(2-nitrophenyl)-propan-1-one
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H14 Br N O4'
_chemical_formula_sum            'C16 H14 Br N O4'
_exptl_crystal_recrystallization_method 
'slow evaporation of an ethanol solution at r.t.'
_chemical_melting_point          374

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         364.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

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

_cell_length_a                   7.8816(8)
_cell_length_b                   10.0220(10)
_cell_length_c                   10.4165(11)
_cell_angle_alpha                106.091(4)
_cell_angle_beta                 94.967(5)
_cell_angle_gamma                100.946(4)
_cell_volume                     767.68(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3957
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.546
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.288
_exptl_absorpt_coefficient_mu    2.694
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6111
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6923
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.661
_diffrn_reflns_theta_max         25.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2790
_reflns_number_gt                2175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0698P)²+0.7340P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2790
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.41023(6) 0.80624(5) 0.34044(5) 0.0724(2) Uani 1 1 d . . . . .
O1 O 0.0509(3) 0.5621(3) 0.3957(3) 0.0573(7) Uani 1 1 d . . . . .
O3 O 0.3152(4) 0.5724(4) 0.6076(3) 0.0615(8) Uani 1 1 d D . . . .
H3 H 0.212(3) 0.537(5) 0.592(5) 0.066(15) Uiso 1 1 d D . . . .
O11 O 0.3033(5) 0.9075(5) 0.7933(4) 0.1034(15) Uani 1 1 d . . . . .
O12 O 0.4178(5) 0.8354(5) 0.9463(5) 0.0944(13) Uani 1 1 d . . . . .
N1 N 0.4177(5) 0.8651(5) 0.8393(4) 0.0693(12) Uani 1 1 d . . . . .
C1 C 0.1788(5) 0.5497(4) 0.3397(4) 0.0498(9) Uani 1 1 d . . . . .
C2 C 0.3604(6) 0.6367(5) 0.4122(5) 0.0645(12) Uani 1 1 d . . . . .
H2 H 0.448290 0.579538 0.392468 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3678(6) 0.6967(6) 0.5584(5) 0.0698(14) Uani 1 1 d . . . . .
H31 H 0.284677 0.758568 0.576970 0.084 Uiso 1 1 calc R U . . .
C11 C 0.1670(5) 0.4623(4) 0.1983(4) 0.0449(8) Uani 1 1 d . . . . .
C12 C 0.0018(5) 0.3949(4) 0.1241(4) 0.0480(9) Uani 1 1 d . . . . .
H12 H -0.097791 0.402616 0.164948 0.058 Uiso 1 1 calc R U . . .
C13 C -0.0133(5) 0.3167(4) -0.0099(4) 0.0510(9) Uani 1 1 d . . . . .
H13 H -0.123813 0.271587 -0.058341 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1314(6) 0.3041(4) -0.0736(4) 0.0521(10) Uani 1 1 d . . . . .
C15 C 0.2942(6) 0.3677(5) 0.0006(5) 0.0588(11) Uani 1 1 d . . . . .
H15 H 0.393166 0.358267 -0.040646 0.071 Uiso 1 1 calc R U . . .
C16 C 0.3133(5) 0.4450(5) 0.1349(4) 0.0555(10) Uani 1 1 d . . . . .
H16 H 0.424554 0.485940 0.183499 0.067 Uiso 1 1 calc R U . . .
C17 C 0.1162(7) 0.2265(5) -0.2227(5) 0.0705(13) Uani 1 1 d . . . . .
H17A H 0.148973 0.294314 -0.270636 0.106 Uiso 1 1 calc R U . . .
H17B H -0.002317 0.175070 -0.256572 0.106 Uiso 1 1 calc R U . . .
H17C H 0.192126 0.161048 -0.235349 0.106 Uiso 1 1 calc R U . . .
C31 C 0.5489(5) 0.7770(5) 0.6342(4) 0.0547(11) Uani 1 1 d . . . . .
C32 C 0.5705(5) 0.8495(4) 0.7687(4) 0.0476(9) Uani 1 1 d . . . . .
C33 C 0.7310(5) 0.9054(4) 0.8475(4) 0.0526(10) Uani 1 1 d . . . . .
H33 H 0.738815 0.950574 0.939483 0.063 Uiso 1 1 calc R U . . .
C34 C 0.8797(5) 0.8944(4) 0.7901(4) 0.0526(10) Uani 1 1 d . . . . .
H34 H 0.989147 0.933516 0.842106 0.063 Uiso 1 1 calc R U . . .
C35 C 0.8649(5) 0.8255(5) 0.6556(5) 0.0606(11) Uani 1 1 d . . . . .
H35 H 0.965011 0.817725 0.615498 0.073 Uiso 1 1 calc R U . . .
C36 C 0.7026(5) 0.7673(5) 0.5787(5) 0.0640(12) Uani 1 1 d . . . . .
H36 H 0.695324 0.720128 0.487216 0.077 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 2.026(5) . ?
O1 C1 1.217(5) . ?
O3 C3 1.477(7) . ?
O3 H3 0.80(2) . ?
O11 N1 1.186(6) . ?
O12 N1 1.231(6) . ?
N1 C32 1.475(5) . ?
C1 C11 1.475(6) . ?
C1 C2 1.534(6) . ?
C2 C3 1.465(7) . ?
C2 H2 0.9800 . ?
C3 C31 1.525(5) . ?
C3 H31 0.9800 . ?
C11 C16 1.393(6) . ?
C11 C12 1.397(5) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(6) . ?
C14 C17 1.514(6) . ?
C15 C16 1.378(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C31 C32 1.366(6) . ?
C31 C36 1.396(6) . ?
C32 C33 1.373(5) . ?
C33 C34 1.370(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.363(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.378(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 H3 115(4) . . ?
O11 N1 O12 123.0(4) . . ?
O11 N1 C32 119.7(5) . . ?
O12 N1 C32 117.3(4) . . ?
O1 C1 C11 122.8(3) . . ?
O1 C1 C2 120.0(4) . . ?
C11 C1 C2 117.0(3) . . ?
C3 C2 C1 113.6(4) . . ?
C3 C2 Br1 105.6(3) . . ?
C1 C2 Br1 105.8(3) . . ?
C3 C2 H2 110.6 . . ?
C1 C2 H2 110.6 . . ?
Br1 C2 H2 110.6 . . ?
C2 C3 O3 105.0(4) . . ?
C2 C3 C31 114.7(4) . . ?
O3 C3 C31 107.1(4) . . ?
C2 C3 H31 109.9 . . ?
O3 C3 H31 109.9 . . ?
C31 C3 H31 109.9 . . ?
C16 C11 C12 118.5(4) . . ?
C16 C11 C1 122.9(3) . . ?
C12 C11 C1 118.6(3) . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 118.5(4) . . ?
C15 C14 C17 119.4(4) . . ?
C13 C14 C17 122.0(4) . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 120.4(4) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C32 C31 C36 115.6(3) . . ?
C32 C31 C3 120.4(4) . . ?
C36 C31 C3 123.5(4) . . ?
C31 C32 C33 123.4(3) . . ?
C31 C32 N1 120.6(3) . . ?
C33 C32 N1 116.0(3) . . ?
C34 C33 C32 119.7(4) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C35 C34 C33 119.1(3) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 120.4(4) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 121.8(4) . . ?
C35 C36 H36 119.1 . . ?
C31 C36 H36 119.1 . . ?

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
O1 C1 C2 C3 16.8(6) . . . . ?
C11 C1 C2 C3 -168.2(4) . . . . ?
O1 C1 C2 Br1 -98.5(4) . . . . ?
C11 C1 C2 Br1 76.5(4) . . . . ?
C1 C2 C3 O3 59.5(5) . . . . ?
Br1 C2 C3 O3 174.9(2) . . . . ?
C1 C2 C3 C31 176.9(4) . . . . ?
Br1 C2 C3 C31 -67.7(5) . . . . ?
O1 C1 C11 C16 -178.4(4) . . . . ?
C2 C1 C11 C16 6.7(6) . . . . ?
O1 C1 C11 C12 2.2(6) . . . . ?
C2 C1 C11 C12 -172.7(4) . . . . ?
C16 C11 C12 C13 -1.8(6) . . . . ?
C1 C11 C12 C13 177.6(4) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C15 2.1(6) . . . . ?
C12 C13 C14 C17 -176.1(4) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
C17 C14 C15 C16 176.8(4) . . . . ?
C14 C15 C16 C11 -0.9(7) . . . . ?
C12 C11 C16 C15 2.5(6) . . . . ?
C1 C11 C16 C15 -176.9(4) . . . . ?
C2 C3 C31 C32 173.7(4) . . . . ?
O3 C3 C31 C32 -70.1(5) . . . . ?
C2 C3 C31 C36 -14.8(7) . . . . ?
O3 C3 C31 C36 101.3(5) . . . . ?
C36 C31 C32 C33 -2.4(7) . . . . ?
C3 C31 C32 C33 169.8(5) . . . . ?
C36 C31 C32 N1 -179.1(4) . . . . ?
C3 C31 C32 N1 -7.0(7) . . . . ?
O11 N1 C32 C31 -50.8(6) . . . . ?
O12 N1 C32 C31 130.6(5) . . . . ?
O11 N1 C32 C33 132.2(5) . . . . ?
O12 N1 C32 C33 -46.3(6) . . . . ?
C31 C32 C33 C34 2.6(7) . . . . ?
N1 C32 C33 C34 179.5(4) . . . . ?
C32 C33 C34 C35 -1.2(7) . . . . ?
C33 C34 C35 C36 -0.2(7) . . . . ?
C34 C35 C36 C31 0.4(8) . . . . ?
C32 C31 C36 C35 0.9(7) . . . . ?
C3 C31 C36 C35 -171.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.80(2) 2.15(2) 2.937(4) 164(5) 2_566 yes
C2 H2 O3 0.98 2.62 3.586(6) 168.0 2_666 yes
C34 H34 O11 0.93 2.62 3.313(5) 132.2 1_655 yes

_refine_diff_density_max         0.965
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.080



####################################################################### 
# 
# 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_v519
_database_code_depnum_ccdc_archive 'CCDC 1885354'
_audit_update_record             
;
2018-12-16 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;

# start Validation Reply
_vrf_PLAT410_v519                
;
PROBLEM: Short Intra H...H Contact  H2       ..H16      .       1.97 Ang.  
RESPONSE: Intramolecular contact H2...H16 according to topological analysis
of calculated electron density in the crystal phase has an attractive
nature and belongs to closed shell interaction.
;
_vrf_PLAT430_v519                
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.89 Ang.  
RESPONSE: Intermolecular head-to-head contact between two carbonyl oxygen
atoms O1...O1 (1-x,-y,1-z) according to topological analysis of calculated
electron density has an attractive nature and belongs to closed
shell interaction. More details in the pubslished article.
;
# end Validation Reply

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(2RS,3RS)-2-bromo-3-hydroxy-3-(2-nitrophenyl)-1-phenylpropan-1-one
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H12 Br N O4'
_chemical_formula_sum            'C15 H12 Br N O4'
_exptl_crystal_recrystallization_method 
'slow evaporation of an ethanol solution at r.t.'
_chemical_melting_point          375

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         350.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

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

_cell_length_a                   7.746(2)
_cell_length_b                   7.881(2)
_cell_length_c                   12.467(4)
_cell_angle_alpha                92.370(4)
_cell_angle_beta                 103.440(4)
_cell_angle_gamma                94.136(4)
_cell_volume                     737.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5076
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.513
_exptl_crystal_size_min          0.278
_exptl_absorpt_coefficient_mu    2.803
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3569
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11025
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.682
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2789
_reflns_number_gt                2340
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0523P)²+0.9680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2789
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.77319(6) 0.51163(5) 0.56737(4) 0.0666(2) Uani 1 1 d . . . . .
O1 O 0.4967(3) 0.1779(3) 0.47698(19) 0.0430(5) Uani 1 1 d . . . . .
O3 O 0.8399(3) -0.0015(3) 0.5906(2) 0.0437(5) Uani 1 1 d . . . . .
H3 H 0.739366 -0.050072 0.578224 0.066 Uiso 1 1 calc R U . . .
O11 O 0.8689(6) 0.4877(8) 0.8832(4) 0.1283(19) Uani 1 1 d . . . . .
O12 O 0.7831(6) 0.2253(8) 0.8578(4) 0.1267(19) Uani 1 1 d . . . . .
N1 N 0.8871(5) 0.3409(7) 0.8533(3) 0.0745(13) Uani 1 1 d . . . . .
C1 C 0.6272(4) 0.2161(4) 0.4421(3) 0.0353(7) Uani 1 1 d . . . . .
C2 C 0.8010(4) 0.2763(4) 0.5252(3) 0.0359(7) Uani 1 1 d . . . . .
H2 H 0.900819 0.272490 0.489413 0.043 Uiso 1 1 calc R U . . .
C3 C 0.8349(4) 0.1702(4) 0.6270(2) 0.0332(6) Uani 1 1 d . . . . .
H31 H 0.740144 0.180123 0.666450 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6234(4) 0.2072(4) 0.3227(3) 0.0386(7) Uani 1 1 d . . . . .
C12 C 0.4595(5) 0.1941(5) 0.2473(3) 0.0547(9) Uani 1 1 d . . . . .
H12 H 0.355546 0.195747 0.272381 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4499(7) 0.1785(7) 0.1356(3) 0.0735(13) Uani 1 1 d . . . . .
H13 H 0.339498 0.170369 0.085598 0.088 Uiso 1 1 calc R U . . .
C14 C 0.6025(8) 0.1749(6) 0.0978(4) 0.0753(14) Uani 1 1 d . . . . .
H14 H 0.594925 0.164013 0.022278 0.090 Uiso 1 1 calc R U . . .
C15 C 0.7652(7) 0.1873(7) 0.1704(4) 0.0732(13) Uani 1 1 d . . . . .
H15 H 0.868231 0.184222 0.144401 0.088 Uiso 1 1 calc R U . . .
C16 C 0.7764(5) 0.2046(5) 0.2831(3) 0.0551(9) Uani 1 1 d . . . . .
H16 H 0.887385 0.214476 0.332499 0.066 Uiso 1 1 calc R U . . .
C31 C 1.0147(4) 0.2307(4) 0.7025(2) 0.0319(6) Uani 1 1 d . . . . .
C32 C 1.0405(4) 0.3135(5) 0.8053(3) 0.0428(8) Uani 1 1 d . . . . .
C33 C 1.2059(5) 0.3764(6) 0.8678(3) 0.0569(10) Uani 1 1 d . . . . .
H33 H 1.216957 0.433844 0.936068 0.068 Uiso 1 1 calc R U . . .
C34 C 1.3537(5) 0.3529(5) 0.8278(3) 0.0519(9) Uani 1 1 d . . . . .
H34 H 1.466404 0.392751 0.869260 0.062 Uiso 1 1 calc R U . . .
C35 C 1.3341(4) 0.2703(5) 0.7263(3) 0.0496(9) Uani 1 1 d . . . . .
H35 H 1.433898 0.254327 0.698717 0.060 Uiso 1 1 calc R U . . .
C36 C 1.1669(4) 0.2105(5) 0.6645(3) 0.0426(8) Uani 1 1 d . . . . .
H36 H 1.156325 0.155256 0.595636 0.051 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.947(3) . ?
O1 C1 1.214(4) . ?
O3 C3 1.416(4) . ?
O3 H3 0.8200 . ?
O11 N1 1.229(7) . ?
O12 N1 1.183(6) . ?
N1 C32 1.475(5) . ?
C1 C11 1.481(5) . ?
C1 C2 1.527(4) . ?
C2 C3 1.530(4) . ?
C2 H2 0.9800 . ?
C3 C31 1.519(4) . ?
C3 H31 0.9800 . ?
C11 C16 1.386(5) . ?
C11 C12 1.387(5) . ?
C12 C13 1.377(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C31 C32 1.379(4) . ?
C31 C36 1.386(4) . ?
C32 C33 1.381(5) . ?
C33 C34 1.373(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.370(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.382(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 H3 109.5 . . ?
O12 N1 O11 122.4(5) . . ?
O12 N1 C32 120.2(5) . . ?
O11 N1 C32 117.3(5) . . ?
O1 C1 C11 122.6(3) . . ?
O1 C1 C2 118.3(3) . . ?
C11 C1 C2 119.2(3) . . ?
C1 C2 C3 112.5(3) . . ?
C1 C2 Br1 104.8(2) . . ?
C3 C2 Br1 110.3(2) . . ?
C1 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
Br1 C2 H2 109.7 . . ?
O3 C3 C31 108.5(2) . . ?
O3 C3 C2 107.9(2) . . ?
C31 C3 C2 109.5(2) . . ?
O3 C3 H31 110.3 . . ?
C31 C3 H31 110.3 . . ?
C2 C3 H31 110.3 . . ?
C16 C11 C12 118.6(3) . . ?
C16 C11 C1 122.8(3) . . ?
C12 C11 C1 118.5(3) . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.5(4) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C32 C31 C36 115.9(3) . . ?
C32 C31 C3 125.4(3) . . ?
C36 C31 C3 118.6(3) . . ?
C31 C32 C33 123.3(3) . . ?
C31 C32 N1 120.2(3) . . ?
C33 C32 N1 116.5(3) . . ?
C34 C33 C32 119.0(3) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C35 C34 C33 119.5(3) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 120.4(3) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 121.8(3) . . ?
C35 C36 H36 119.1 . . ?
C31 C36 H36 119.1 . . ?

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
O1 C1 C2 C3 42.1(4) . . . . ?
C11 C1 C2 C3 -138.3(3) . . . . ?
O1 C1 C2 Br1 -77.8(3) . . . . ?
C11 C1 C2 Br1 101.8(3) . . . . ?
C1 C2 C3 O3 58.7(3) . . . . ?
Br1 C2 C3 O3 175.40(18) . . . . ?
C1 C2 C3 C31 176.7(2) . . . . ?
Br1 C2 C3 C31 -66.6(3) . . . . ?
O1 C1 C11 C16 -161.9(3) . . . . ?
C2 C1 C11 C16 18.5(5) . . . . ?
O1 C1 C11 C12 15.4(5) . . . . ?
C2 C1 C11 C12 -164.2(3) . . . . ?
C16 C11 C12 C13 0.1(6) . . . . ?
C1 C11 C12 C13 -177.3(4) . . . . ?
C11 C12 C13 C14 0.4(7) . . . . ?
C12 C13 C14 C15 -0.2(8) . . . . ?
C13 C14 C15 C16 -0.4(8) . . . . ?
C12 C11 C16 C15 -0.7(6) . . . . ?
C1 C11 C16 C15 176.7(4) . . . . ?
C14 C15 C16 C11 0.8(7) . . . . ?
O3 C3 C31 C32 -130.8(3) . . . . ?
C2 C3 C31 C32 111.6(4) . . . . ?
O3 C3 C31 C36 52.8(4) . . . . ?
C2 C3 C31 C36 -64.8(4) . . . . ?
C36 C31 C32 C33 1.0(6) . . . . ?
C3 C31 C32 C33 -175.5(4) . . . . ?
C36 C31 C32 N1 -179.8(4) . . . . ?
C3 C31 C32 N1 3.8(6) . . . . ?
O12 N1 C32 C31 51.3(6) . . . . ?
O11 N1 C32 C31 -125.6(4) . . . . ?
O12 N1 C32 C33 -129.4(5) . . . . ?
O11 N1 C32 C33 53.7(6) . . . . ?
C31 C32 C33 C34 -1.5(6) . . . . ?
N1 C32 C33 C34 179.2(4) . . . . ?
C32 C33 C34 C35 1.0(6) . . . . ?
C33 C34 C35 C36 -0.2(6) . . . . ?
C34 C35 C36 C31 -0.3(6) . . . . ?
C32 C31 C36 C35 -0.1(5) . . . . ?
C3 C31 C36 C35 176.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.82 1.98 2.793(3) 170.2 2_656 yes
C33 H33 O11 0.93 2.56 3.430(5) 156.4 2_767 yes
C36 H36 O3 0.93 2.58 3.509(4) 174.4 2_756 yes

_refine_diff_density_max         0.761
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_v530
_database_code_depnum_ccdc_archive 'CCDC 1885355'
_audit_update_record             
;
2018-12-16 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(2RS,3SR)-3-(2-nitrophenyl)-1-phenyl-2,3-epoxypropan-1-one
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H11 N O4'
_chemical_formula_sum            'C15 H11 N O4'
_exptl_crystal_recrystallization_method 
'slow evaporation of an ethanol solution at r.t.'
_chemical_melting_point          388

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         269.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_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'

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

_cell_length_a                   7.800(4)
_cell_length_b                   15.919(8)
_cell_length_c                   10.373(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.416(6)
_cell_angle_gamma                90
_cell_volume                     1274.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2072
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      22.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.352
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5989
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8812
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         25.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2345
_reflns_number_gt                1652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0399P)²+0.3327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2345
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4951(2) 0.31955(10) 0.22839(14) 0.0770(5) Uani 1 1 d . . . . .
O3 O 0.59350(19) 0.42254(8) 0.44089(12) 0.0615(4) Uani 1 1 d . . . . .
O11 O 0.5437(2) 0.20998(9) 0.64648(13) 0.0690(4) Uani 1 1 d . . . . .
O12 O 0.6097(2) 0.18733(10) 0.85080(14) 0.0795(5) Uani 1 1 d . . . . .
N1 N 0.6049(2) 0.23280(10) 0.75580(15) 0.0492(4) Uani 1 1 d . . . . .
C1 C 0.6061(2) 0.29163(12) 0.31137(17) 0.0477(5) Uani 1 1 d . . . . .
C2 C 0.6758(3) 0.34393(11) 0.42819(17) 0.0465(5) Uani 1 1 d . . . . .
H2 H 0.801850 0.343027 0.453484 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5733(2) 0.35848(11) 0.53400(17) 0.0454(4) Uani 1 1 d . . . . .
H3 H 0.459777 0.330968 0.525223 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6776(2) 0.20579(11) 0.30486(16) 0.0425(4) Uani 1 1 d . . . . .
C12 C 0.7757(2) 0.16842(11) 0.41229(17) 0.0471(5) Uani 1 1 d . . . . .
H12 H 0.800952 0.198252 0.489830 0.057 Uiso 1 1 calc R U . . .
C13 C 0.8357(3) 0.08739(13) 0.4046(2) 0.0571(5) Uani 1 1 d . . . . .
H13 H 0.899987 0.062585 0.477306 0.069 Uiso 1 1 calc R U . . .
C14 C 0.8012(3) 0.04324(14) 0.2903(2) 0.0661(6) Uani 1 1 d . . . . .
H14 H 0.842501 -0.011301 0.285523 0.079 Uiso 1 1 calc R U . . .
C15 C 0.7054(3) 0.07955(14) 0.1827(2) 0.0679(6) Uani 1 1 d . . . . .
H15 H 0.682527 0.049526 0.105171 0.082 Uiso 1 1 calc R U . . .
C16 C 0.6431(3) 0.16051(13) 0.18946(18) 0.0548(5) Uani 1 1 d . . . . .
H16 H 0.577985 0.184701 0.116619 0.066 Uiso 1 1 calc R U . . .
C31 C 0.6594(2) 0.37557(11) 0.67003(16) 0.0418(4) Uani 1 1 d . . . . .
C32 C 0.6754(2) 0.31823(11) 0.77350(16) 0.0415(4) Uani 1 1 d . . . . .
C33 C 0.7553(2) 0.33902(12) 0.89684(18) 0.0518(5) Uani 1 1 d . . . . .
H33 H 0.763568 0.299640 0.963680 0.062 Uiso 1 1 calc R U . . .
C34 C 0.8227(3) 0.41825(14) 0.9205(2) 0.0622(6) Uani 1 1 d . . . . .
H34 H 0.878295 0.432492 1.003128 0.075 Uiso 1 1 calc R U . . .
C35 C 0.8076(3) 0.47614(13) 0.8217(2) 0.0623(6) Uani 1 1 d . . . . .
H35 H 0.851737 0.529991 0.837944 0.075 Uiso 1 1 calc R U . . .
C36 C 0.7276(2) 0.45532(12) 0.69846(19) 0.0531(5) Uani 1 1 d . . . . .
H36 H 0.719085 0.495520 0.632774 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.213(2) . ?
O3 C2 1.421(2) . ?
O3 C3 1.429(2) . ?
O11 N1 1.2195(19) . ?
O12 N1 1.2188(19) . ?
N1 C32 1.469(2) . ?
C1 C11 1.481(3) . ?
C1 C2 1.505(3) . ?
C2 C3 1.468(2) . ?
C2 H2 0.9800 . ?
C3 C31 1.496(2) . ?
C3 H3 0.9800 . ?
C11 C16 1.389(2) . ?
C11 C12 1.390(2) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C31 C36 1.391(3) . ?
C31 C32 1.401(2) . ?
C32 C33 1.379(2) . ?
C33 C34 1.375(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.371(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.378(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O3 C3 61.98(11) . . ?
O12 N1 O11 122.44(17) . . ?
O12 N1 C32 118.83(15) . . ?
O11 N1 C32 118.73(15) . . ?
O1 C1 C11 122.71(17) . . ?
O1 C1 C2 120.33(18) . . ?
C11 C1 C2 116.96(16) . . ?
O3 C2 C3 59.27(11) . . ?
O3 C2 C1 116.56(15) . . ?
C3 C2 C1 121.16(17) . . ?
O3 C2 H2 115.9 . . ?
C3 C2 H2 115.9 . . ?
C1 C2 H2 115.9 . . ?
O3 C3 C2 58.75(11) . . ?
O3 C3 C31 115.39(16) . . ?
C2 C3 C31 121.01(16) . . ?
O3 C3 H3 116.3 . . ?
C2 C3 H3 116.3 . . ?
C31 C3 H3 116.3 . . ?
C16 C11 C12 118.90(18) . . ?
C16 C11 C1 119.42(17) . . ?
C12 C11 C1 121.67(16) . . ?
C13 C12 C11 120.40(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.13(19) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C36 C31 C32 116.35(16) . . ?
C36 C31 C3 118.09(16) . . ?
C32 C31 C3 125.55(16) . . ?
C33 C32 C31 122.14(17) . . ?
C33 C32 N1 116.65(16) . . ?
C31 C32 N1 121.20(15) . . ?
C34 C33 C32 119.68(19) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C35 C34 C33 119.63(19) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 120.65(19) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C31 121.54(19) . . ?
C35 C36 H36 119.2 . . ?
C31 C36 H36 119.2 . . ?

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
C3 O3 C2 C1 112.08(19) . . . . ?
O1 C1 C2 O3 5.8(3) . . . . ?
C11 C1 C2 O3 -173.38(15) . . . . ?
O1 C1 C2 C3 74.4(2) . . . . ?
C11 C1 C2 C3 -104.8(2) . . . . ?
C2 O3 C3 C31 112.28(18) . . . . ?
C1 C2 C3 O3 -104.38(18) . . . . ?
O3 C2 C3 C31 -102.73(18) . . . . ?
C1 C2 C3 C31 152.89(17) . . . . ?
O1 C1 C11 C16 12.7(3) . . . . ?
C2 C1 C11 C16 -168.12(16) . . . . ?
O1 C1 C11 C12 -165.90(18) . . . . ?
C2 C1 C11 C12 13.3(3) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
C1 C11 C12 C13 177.85(17) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
C1 C11 C16 C15 -178.46(18) . . . . ?
O3 C3 C31 C36 9.4(2) . . . . ?
C2 C3 C31 C36 76.7(2) . . . . ?
O3 C3 C31 C32 -171.78(16) . . . . ?
C2 C3 C31 C32 -104.4(2) . . . . ?
C36 C31 C32 C33 -0.5(3) . . . . ?
C3 C31 C32 C33 -179.33(17) . . . . ?
C36 C31 C32 N1 178.63(15) . . . . ?
C3 C31 C32 N1 -0.2(3) . . . . ?
O12 N1 C32 C33 4.9(2) . . . . ?
O11 N1 C32 C33 -175.10(17) . . . . ?
O12 N1 C32 C31 -174.26(17) . . . . ?
O11 N1 C32 C31 5.8(2) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
N1 C32 C33 C34 -179.37(17) . . . . ?
C32 C33 C34 C35 0.9(3) . . . . ?
C33 C34 C35 C36 -0.9(3) . . . . ?
C34 C35 C36 C31 0.2(3) . . . . ?
C32 C31 C36 C35 0.5(3) . . . . ?
C3 C31 C36 C35 179.44(17) . . . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.031



####################################################################### 
# 
# 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_v600
_database_code_depnum_ccdc_archive 'CCDC 1885353'
_audit_update_record             
;
2018-12-16 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;

# start Validation Reply
_vrf_PLAT430_v600                
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.78 Ang.  
RESPONSE: Intermolecular head-to-head contact between two carbonyl oxygen
atoms O1...O1 (1-x,-y,-z) according to topological analysis of calculated
electron density has an attractive nature and belongs to closed
shell interaction. More details in the pubslished article.
;
# end Validation Reply

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(2RS,3RS)-2-bromo-1-(4-chlorophenyl)-3-hydroxy-3-(2-nitrophenyl)-propan-1-one
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H11 Br Cl N O4'
_chemical_formula_sum            'C15 H11 Br Cl N O4'
_exptl_crystal_recrystallization_method 
'slow evaporation of an ethanol solution at r.t.'
_chemical_melting_point          398

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         384.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_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'

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

_cell_length_a                   14.847(11)
_cell_length_b                   7.932(6)
_cell_length_c                   14.919(11)
_cell_angle_alpha                90
_cell_angle_beta                 118.211(9)
_cell_angle_gamma                90
_cell_volume                     1548.1(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2580
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      19.78
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    2.844
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5321
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12347
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.665
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2844
_reflns_number_gt                2026
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_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     
'w=1/[σ²(Fo²)+(0.0674P)²+2.4189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2844
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.76467(5) 0.33959(9) 0.22048(4) 0.0785(3) Uani 1 1 d . . . . .
Cl1 Cl 0.45881(19) 0.2668(3) 0.47025(17) 0.1112(8) Uani 1 1 d . . . . .
O1 O 0.5658(2) 0.0492(4) 0.0992(2) 0.0482(8) Uani 1 1 d . . . . .
O3 O 0.5195(3) 0.2865(5) -0.0670(3) 0.0558(10) Uani 1 1 d . . . . .
H3 H 0.506(5) 0.186(8) -0.076(5) 0.08(2) Uiso 1 1 d . . . . .
O11 O 0.7128(5) 0.1363(5) -0.0973(5) 0.108(2) Uani 1 1 d . . . . .
O12 O 0.6556(6) 0.2646(7) -0.2400(5) 0.129(2) Uani 1 1 d . . . . .
N1 N 0.6888(5) 0.2631(7) -0.1477(5) 0.0806(17) Uani 1 1 d . . . . .
C1 C 0.5728(3) 0.1864(6) 0.1382(3) 0.0439(11) Uani 1 1 d . . . . .
C2 C 0.6213(4) 0.3340(6) 0.1090(4) 0.0549(13) Uani 1 1 d . . . . .
H2 H 0.586162 0.440209 0.105751 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6256(4) 0.3034(6) 0.0124(4) 0.0543(13) Uani 1 1 d . . . . .
H31 H 0.662408 0.198070 0.017933 0.065 Uiso 1 1 calc R U . . .
C11 C 0.5438(4) 0.2149(6) 0.2189(3) 0.0443(11) Uani 1 1 d . . . . .
C12 C 0.5132(4) 0.0744(7) 0.2553(4) 0.0534(13) Uani 1 1 d . . . . .
H12 H 0.510585 -0.031403 0.227383 0.064 Uiso 1 1 calc R U . . .
C13 C 0.4869(5) 0.0919(8) 0.3323(4) 0.0652(15) Uani 1 1 d . . . . .
H13 H 0.466549 -0.001205 0.356159 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4914(5) 0.2484(8) 0.3729(4) 0.0658(15) Uani 1 1 d . . . . .
C15 C 0.5194(5) 0.3884(8) 0.3386(5) 0.0707(16) Uani 1 1 d . . . . .
H15 H 0.520493 0.493832 0.366349 0.085 Uiso 1 1 calc R U . . .
C16 C 0.5460(5) 0.3705(6) 0.2620(4) 0.0607(14) Uani 1 1 d . . . . .
H16 H 0.565882 0.465104 0.238846 0.073 Uiso 1 1 calc R U . . .
C31 C 0.6742(4) 0.4460(6) -0.0184(4) 0.0482(12) Uani 1 1 d . . . . .
C32 C 0.6995(4) 0.4268(6) -0.0961(4) 0.0520(12) Uani 1 1 d . . . . .
C33 C 0.7325(4) 0.5593(7) -0.1341(5) 0.0626(15) Uani 1 1 d . . . . .
H33 H 0.746941 0.541753 -0.187565 0.075 Uiso 1 1 calc R U . . .
C34 C 0.7434(4) 0.7156(6) -0.0920(5) 0.0595(14) Uani 1 1 d . . . . .
H34 H 0.767464 0.804671 -0.115303 0.071 Uiso 1 1 calc R U . . .
C35 C 0.7192(4) 0.7405(6) -0.0161(4) 0.0573(14) Uani 1 1 d . . . . .
H35 H 0.725885 0.847436 0.011927 0.069 Uiso 1 1 calc R U . . .
C36 C 0.6846(4) 0.6081(6) 0.0201(4) 0.0542(13) Uani 1 1 d . . . . .
H36 H 0.667766 0.628563 0.071767 0.065 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.988(6) . ?
Cl1 C14 1.740(6) . ?
O1 C1 1.215(6) . ?
O3 C3 1.463(6) . ?
O3 H3 0.82(6) . ?
O11 N1 1.204(7) . ?
O12 N1 1.224(8) . ?
N1 C32 1.479(7) . ?
C1 C11 1.475(7) . ?
C1 C2 1.542(7) . ?
C2 C3 1.492(7) . ?
C2 H2 0.9800 . ?
C3 C31 1.525(7) . ?
C3 H31 0.9800 . ?
C11 C16 1.385(7) . ?
C11 C12 1.406(7) . ?
C12 C13 1.384(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(8) . ?
C15 C16 1.382(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C31 C32 1.385(7) . ?
C31 C36 1.386(7) . ?
C32 C33 1.389(7) . ?
C33 C34 1.364(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.354(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(7) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 H3 108(5) . . ?
O11 N1 O12 123.5(6) . . ?
O11 N1 C32 118.8(6) . . ?
O12 N1 C32 117.7(6) . . ?
O1 C1 C11 122.5(4) . . ?
O1 C1 C2 119.3(4) . . ?
C11 C1 C2 118.0(4) . . ?
C3 C2 C1 112.9(4) . . ?
C3 C2 Br1 107.1(4) . . ?
C1 C2 Br1 103.8(3) . . ?
C3 C2 H2 110.9 . . ?
C1 C2 H2 110.9 . . ?
Br1 C2 H2 110.9 . . ?
O3 C3 C2 106.0(4) . . ?
O3 C3 C31 107.8(4) . . ?
C2 C3 C31 114.4(4) . . ?
O3 C3 H31 109.5 . . ?
C2 C3 H31 109.5 . . ?
C31 C3 H31 109.5 . . ?
C16 C11 C12 117.9(5) . . ?
C16 C11 C1 124.3(4) . . ?
C12 C11 C1 117.8(4) . . ?
C13 C12 C11 120.7(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 122.0(5) . . ?
C15 C14 Cl1 119.9(5) . . ?
C13 C14 Cl1 118.1(5) . . ?
C14 C15 C16 118.9(5) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C11 121.4(5) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C32 C31 C36 115.3(4) . . ?
C32 C31 C3 121.6(4) . . ?
C36 C31 C3 122.6(5) . . ?
C31 C32 C33 123.0(5) . . ?
C31 C32 N1 121.8(4) . . ?
C33 C32 N1 115.1(5) . . ?
C34 C33 C32 119.3(5) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C35 C34 C33 119.8(5) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.6(5) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 122.0(5) . . ?
C31 C36 H36 119.0 . . ?
C35 C36 H36 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 17.6(7) . . . . ?
C11 C1 C2 C3 -167.1(4) . . . . ?
O1 C1 C2 Br1 -98.0(4) . . . . ?
C11 C1 C2 Br1 77.3(5) . . . . ?
C1 C2 C3 O3 62.0(5) . . . . ?
Br1 C2 C3 O3 175.6(3) . . . . ?
C1 C2 C3 C31 -179.4(4) . . . . ?
Br1 C2 C3 C31 -65.8(5) . . . . ?
O1 C1 C11 C16 -176.9(5) . . . . ?
C2 C1 C11 C16 8.0(7) . . . . ?
O1 C1 C11 C12 4.0(7) . . . . ?
C2 C1 C11 C12 -171.2(4) . . . . ?
C16 C11 C12 C13 -0.4(8) . . . . ?
C1 C11 C12 C13 178.7(5) . . . . ?
C11 C12 C13 C14 -0.2(9) . . . . ?
C12 C13 C14 C15 1.1(10) . . . . ?
C12 C13 C14 Cl1 -179.6(4) . . . . ?
C13 C14 C15 C16 -1.4(10) . . . . ?
Cl1 C14 C15 C16 179.3(5) . . . . ?
C14 C15 C16 C11 0.7(9) . . . . ?
C12 C11 C16 C15 0.2(8) . . . . ?
C1 C11 C16 C15 -179.0(5) . . . . ?
O3 C3 C31 C32 -73.2(6) . . . . ?
C2 C3 C31 C32 169.2(5) . . . . ?
O3 C3 C31 C36 98.7(6) . . . . ?
C2 C3 C31 C36 -18.9(8) . . . . ?
C36 C31 C32 C33 -0.3(8) . . . . ?
C3 C31 C32 C33 172.2(5) . . . . ?
C36 C31 C32 N1 -177.7(5) . . . . ?
C3 C31 C32 N1 -5.2(8) . . . . ?
O11 N1 C32 C31 -40.4(8) . . . . ?
O12 N1 C32 C31 139.4(6) . . . . ?
O11 N1 C32 C33 142.0(6) . . . . ?
O12 N1 C32 C33 -38.2(8) . . . . ?
C31 C32 C33 C34 1.7(9) . . . . ?
N1 C32 C33 C34 179.3(6) . . . . ?
C32 C33 C34 C35 -2.0(9) . . . . ?
C33 C34 C35 C36 0.8(9) . . . . ?
C32 C31 C36 C35 -0.9(8) . . . . ?
C3 C31 C36 C35 -173.3(5) . . . . ?
C34 C35 C36 C31 0.6(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.82(6) 2.09(7) 2.889(5) 164(6) 3_655 yes
C2 H2 O3 0.98 2.58 3.548(7) 171.1 3_665 yes

_refine_diff_density_max         1.132
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.076



