# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_kmm3out
_audit_block_doi                 10.5517/cc136qpq
_database_code_depnum_ccdc_archive 'CCDC 1019363'
_audit_update_record             
;
2014-08-14 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        CPAM
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 Br F N O3'
_chemical_formula_sum            'C15 H11 Br F N O3'
_chemical_formula_weight         352.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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                   6.5029(9)
_cell_length_b                   4.7911(7)
_cell_length_c                   43.180(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.145(4)
_cell_angle_gamma                90.00
_cell_volume                     1345.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            BEIGE
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    3.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15144
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         0.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2382
_reflns_number_gt                1779
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0693P)²+0.3565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2382
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2193(8) -0.7671(12) 0.20863(12) 0.0335(13) Uani 1 1 d . . .
H1 H 1.1296 -0.6241 0.2140 0.040 Uiso 1 1 calc R . .
C2 C 1.3889(8) -0.8198(12) 0.22717(13) 0.0341(13) Uani 1 1 d . . .
H2 H 1.4103 -0.7159 0.2451 0.041 Uiso 1 1 calc R . .
C3 C 1.5259(8) -1.0259(11) 0.21908(13) 0.0312(13) Uani 1 1 d . . .
C4 C 1.4928(8) -1.1857(10) 0.19223(13) 0.0304(13) Uani 1 1 d . . .
C5 C 1.3197(8) -1.1327(11) 0.17417(13) 0.0325(13) Uani 1 1 d . . .
H5 H 1.2962 -1.2387 0.1565 0.039 Uiso 1 1 calc R . .
C6 C 1.1802(8) -0.9224(11) 0.18222(12) 0.0296(13) Uani 1 1 d . . .
C7 C 0.9987(8) -0.8519(12) 0.16383(12) 0.0325(13) Uani 1 1 d . . .
H7 H 0.9375 -0.6818 0.1686 0.039 Uiso 1 1 calc R . .
C8 C 0.9081(8) -0.9955(12) 0.14126(13) 0.0334(13) Uani 1 1 d . . .
H8 H 0.9571 -1.1716 0.1360 0.040 Uiso 1 1 calc R . .
C9 C 0.7298(8) -0.8766(11) 0.12450(12) 0.0312(13) Uani 1 1 d . . .
C10 C 0.4695(8) -0.9857(11) 0.08520(12) 0.0296(12) Uani 1 1 d . . .
C11 C 0.4576(9) -1.1050(11) 0.05599(13) 0.0331(13) Uani 1 1 d . . .
C12 C 0.3005(9) -1.0378(13) 0.03552(14) 0.0392(14) Uani 1 1 d . . .
H12 H 0.2931 -1.1195 0.0160 0.047 Uiso 1 1 calc R . .
C13 C 0.1569(9) -0.8479(14) 0.04490(14) 0.0433(15) Uani 1 1 d . . .
C14 C 0.1603(9) -0.7267(13) 0.07391(14) 0.0414(15) Uani 1 1 d . . .
H14 H 0.0596 -0.5994 0.0798 0.050 Uiso 1 1 calc R . .
C15 C 0.3157(8) -0.7987(13) 0.09386(14) 0.0381(15) Uani 1 1 d . . .
H15 H 0.3186 -0.7211 0.1136 0.046 Uiso 1 1 calc R . .
N1 N 0.6344(7) -1.0537(9) 0.10508(10) 0.0332(11) Uani 1 1 d . . .
H1A H 0.6777 -1.2233 0.1048 0.040 Uiso 1 1 calc R . .
O1 O 1.7003(6) -1.0818(8) 0.23586(10) 0.0421(11) Uani 1 1 d . . .
H1B H 1.7070 -0.9752 0.2507 0.063 Uiso 1 1 calc R . .
O2 O 1.6362(6) -1.3836(8) 0.18661(10) 0.0456(11) Uani 1 1 d . . .
H2A H 1.6057 -1.4688 0.1708 0.068 Uiso 1 1 calc R . .
O3 O 0.6761(6) -0.6310(8) 0.12767(10) 0.0451(11) Uani 1 1 d . . .
F1 F 0.0060(6) -0.7725(9) 0.02471(9) 0.0634(11) Uani 1 1 d . . .
Br1 Br 0.66249(9) -1.35689(13) 0.042510(14) 0.0456(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.385(8) . ?
C1 C2 1.385(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(8) . ?
C2 H2 0.9300 . ?
C3 O1 1.371(6) . ?
C3 C4 1.406(8) . ?
C4 O2 1.352(6) . ?
C4 C5 1.391(8) . ?
C5 C6 1.400(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.460(7) . ?
C7 C8 1.329(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.479(8) . ?
C8 H8 0.9300 . ?
C9 O3 1.235(6) . ?
C9 N1 1.343(7) . ?
C10 C11 1.387(7) . ?
C10 C15 1.395(8) . ?
C10 N1 1.410(7) . ?
C11 C12 1.387(8) . ?
C11 Br1 1.890(5) . ?
C12 C13 1.366(8) . ?
C12 H12 0.9300 . ?
C13 F1 1.360(6) . ?
C13 C14 1.381(8) . ?
C14 C15 1.370(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N1 H1A 0.8600 . ?
O1 H1B 0.8200 . ?
O2 H2A 0.8200 . ?

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
C6 C1 C2 121.5(5) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
O1 C3 C2 122.8(5) . . ?
O1 C3 C4 117.0(5) . . ?
C2 C3 C4 120.2(5) . . ?
O2 C4 C5 125.8(5) . . ?
O2 C4 C3 115.2(5) . . ?
C5 C4 C3 119.0(5) . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.2(5) . . ?
C1 C6 C7 118.1(5) . . ?
C5 C6 C7 123.7(5) . . ?
C8 C7 C6 129.4(5) . . ?
C8 C7 H7 115.3 . . ?
C6 C7 H7 115.3 . . ?
C7 C8 C9 120.3(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O3 C9 N1 122.7(5) . . ?
O3 C9 C8 122.3(5) . . ?
N1 C9 C8 115.0(5) . . ?
C11 C10 C15 118.1(5) . . ?
C11 C10 N1 119.9(5) . . ?
C15 C10 N1 122.0(5) . . ?
C12 C11 C10 121.5(5) . . ?
C12 C11 Br1 118.1(4) . . ?
C10 C11 Br1 120.4(4) . . ?
C13 C12 C11 117.9(6) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
F1 C13 C12 118.7(6) . . ?
F1 C13 C14 118.7(5) . . ?
C12 C13 C14 122.7(5) . . ?
C15 C14 C13 118.3(5) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C10 121.4(5) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C9 N1 C10 125.7(5) . . ?
C9 N1 H1A 117.2 . . ?
C10 N1 H1A 117.2 . . ?
C3 O1 H1B 109.5 . . ?
C4 O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.6(8) . . . . ?
C1 C2 C3 O1 177.7(5) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
O1 C3 C4 O2 1.9(7) . . . . ?
C2 C3 C4 O2 -179.6(5) . . . . ?
O1 C3 C4 C5 -178.8(5) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
O2 C4 C5 C6 179.8(5) . . . . ?
C3 C4 C5 C6 0.5(8) . . . . ?
C2 C1 C6 C5 -1.3(8) . . . . ?
C2 C1 C6 C7 -179.6(5) . . . . ?
C4 C5 C6 C1 0.2(8) . . . . ?
C4 C5 C6 C7 178.4(5) . . . . ?
C1 C6 C7 C8 -166.7(6) . . . . ?
C5 C6 C7 C8 15.2(9) . . . . ?
C6 C7 C8 C9 -176.8(5) . . . . ?
C7 C8 C9 O3 9.9(9) . . . . ?
C7 C8 C9 N1 -171.7(5) . . . . ?
C15 C10 C11 C12 1.3(8) . . . . ?
N1 C10 C11 C12 -178.4(5) . . . . ?
C15 C10 C11 Br1 179.3(4) . . . . ?
N1 C10 C11 Br1 -0.4(7) . . . . ?
C10 C11 C12 C13 0.4(9) . . . . ?
Br1 C11 C12 C13 -177.6(4) . . . . ?
C11 C12 C13 F1 177.7(5) . . . . ?
C11 C12 C13 C14 -1.4(10) . . . . ?
F1 C13 C14 C15 -178.5(5) . . . . ?
C12 C13 C14 C15 0.7(10) . . . . ?
C13 C14 C15 C10 1.1(9) . . . . ?
C11 C10 C15 C14 -2.1(9) . . . . ?
N1 C10 C15 C14 177.6(5) . . . . ?
O3 C9 N1 C10 2.5(9) . . . . ?
C8 C9 N1 C10 -175.9(5) . . . . ?
C11 C10 N1 C9 142.9(6) . . . . ?
C15 C10 N1 C9 -36.8(8) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.159
