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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1533213'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;
_audit_creation_date             2016-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H12 Br N O'
_chemical_formula_sum            'C19 H12 Br N O'
_chemical_formula_weight         350.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   11.5066(15)
_cell_length_b                   10.2017(13)
_cell_length_c                   12.3497(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.332(4)
_cell_angle_gamma                90
_cell_volume                     1443.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5074
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.600
_exptl_absorpt_coefficient_mu    2.848
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             704
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18101
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         3.057
_diffrn_ambient_temperature      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9627
	          2theta: -15.0947
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9627
	          2theta: -15.0947
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9627
	          2theta: -15.0947
;
_diffrn_measurement_device       
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.070561
_diffrn_orient_matrix_UB_12      -0.019154
_diffrn_orient_matrix_UB_13      0.047675
_diffrn_orient_matrix_UB_21      -0.047537
_diffrn_orient_matrix_UB_22      -0.027213
_diffrn_orient_matrix_UB_23      -0.081291
_diffrn_orient_matrix_UB_31      0.020905
_diffrn_orient_matrix_UB_32      -0.077393
_diffrn_orient_matrix_UB_33      0.013683
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3014
_reflns_number_total             3305
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0205
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.3440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0570
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.06963(2) 0.22316(2) 0.81253(2) 0.01848(6) Uani 1 1 d . . . . .
O1 O 0.10260(10) 0.85993(10) 0.78472(8) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.15845(10) 0.80167(11) 0.61982(9) 0.0113(2) Uani 1 1 d . . . . .
C1 C 0.22134(11) 0.71657(12) 0.55500(10) 0.0107(2) Uani 1 1 d . . . . .
C2 C 0.26099(11) 0.58923(13) 0.57495(11) 0.0137(3) Uani 1 1 d . . . . .
H2 H 0.2425 0.5425 0.6376 0.016 Uiso 1 1 calc R . . . .
C3 C 0.32877(12) 0.53280(14) 0.49965(11) 0.0163(3) Uani 1 1 d . . . . .
H3 H 0.3560 0.4455 0.5108 0.020 Uiso 1 1 calc R . . . .
C4 C 0.35772(12) 0.60175(14) 0.40805(11) 0.0168(3) Uani 1 1 d . . . . .
H4 H 0.4039 0.5606 0.3579 0.020 Uiso 1 1 calc R . . . .
C5 C 0.31977(12) 0.72941(14) 0.38960(11) 0.0144(3) Uani 1 1 d . . . . .
H5 H 0.3400 0.7764 0.3276 0.017 Uiso 1 1 calc R . . . .
C6 C 0.25124(11) 0.78782(12) 0.46387(11) 0.0112(2) Uani 1 1 d . . . . .
C7 C 0.20794(11) 0.92037(13) 0.47341(10) 0.0120(2) Uani 1 1 d . . . . .
C8 C 0.21319(12) 1.03124(14) 0.40814(11) 0.0152(3) Uani 1 1 d . . . . .
H8 H 0.2475 1.0269 0.3412 0.018 Uiso 1 1 calc R . . . .
C9 C 0.16738(12) 1.14806(14) 0.44295(12) 0.0191(3) Uani 1 1 d . . . . .
H9 H 0.1708 1.2247 0.3997 0.023 Uiso 1 1 calc R . . . .
C10 C 0.11623(12) 1.15384(14) 0.54131(12) 0.0191(3) Uani 1 1 d . . . . .
H10 H 0.0857 1.2350 0.5637 0.023 Uiso 1 1 calc R . . . .
C11 C 0.10884(12) 1.04416(14) 0.60733(11) 0.0154(3) Uani 1 1 d . . . . .
H11 H 0.0735 1.0484 0.6738 0.018 Uiso 1 1 calc R . . . .
C12 C 0.15562(11) 0.92784(13) 0.57140(10) 0.0121(2) Uani 1 1 d . . . . .
C13 C 0.11263(12) 0.77408(13) 0.71810(11) 0.0130(3) Uani 1 1 d . . . . .
C14 C 0.07082(11) 0.63825(13) 0.73645(10) 0.0113(2) Uani 1 1 d . . . . .
C15 C 0.08627(11) 0.58774(14) 0.84180(10) 0.0142(3) Uani 1 1 d . . . . .
H15 H 0.1257 0.6383 0.8985 0.017 Uiso 1 1 calc R . . . .
C16 C 0.04442(12) 0.46396(14) 0.86438(11) 0.0147(3) Uani 1 1 d . . . . .
H16 H 0.0571 0.4282 0.9355 0.018 Uiso 1 1 calc R . . . .
C17 C -0.01632(11) 0.39341(13) 0.78115(11) 0.0129(3) Uani 1 1 d . . . . .
C18 C -0.03752(11) 0.44393(13) 0.67659(10) 0.0132(3) Uani 1 1 d . . . . .
H18 H -0.0820 0.3958 0.6214 0.016 Uiso 1 1 calc R . . . .
C19 C 0.00774(11) 0.56621(13) 0.65452(10) 0.0125(3) Uani 1 1 d . . . . .
H19 H -0.0043 0.6012 0.5831 0.015 Uiso 1 1 calc R . . . .


_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 C17 1.8940(14) . ?
O1 C13 1.2145(17) . ?
N1 C1 1.4233(17) . ?
N1 C12 1.4184(17) . ?
N1 C13 1.3961(17) . ?
C1 C2 1.3912(18) . ?
C1 C6 1.4090(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3926(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3973(19) . ?
C6 C7 1.4497(18) . ?
C7 C8 1.3934(19) . ?
C7 C12 1.4029(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3925(19) . ?
C13 C14 1.4911(19) . ?
C14 C15 1.3953(18) . ?
C14 C19 1.3979(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3890(19) . ?
C17 C18 1.3907(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3885(19) . ?
C19 H19 0.9500 . ?

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
C12 N1 C1 108.02(10) . . ?
C13 N1 C1 128.23(11) . . ?
C13 N1 C12 123.62(11) . . ?
C2 C1 N1 130.20(12) . . ?
C2 C1 C6 121.51(12) . . ?
C6 C1 N1 108.01(11) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.56(12) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.50(13) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.70(13) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.77(13) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 107.76(11) . . ?
C5 C6 C1 119.93(12) . . ?
C5 C6 C7 132.09(12) . . ?
C8 C7 C6 132.56(12) . . ?
C8 C7 C12 120.01(12) . . ?
C12 C7 C6 107.40(11) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.67(13) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.51(13) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.88(13) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.6 . . ?
C10 C11 C12 116.87(13) . . ?
C12 C11 H11 121.6 . . ?
C7 C12 N1 108.63(11) . . ?
C11 C12 N1 129.30(12) . . ?
C11 C12 C7 122.05(13) . . ?
O1 C13 N1 120.72(12) . . ?
O1 C13 C14 120.99(12) . . ?
N1 C13 C14 118.21(11) . . ?
C15 C14 C13 118.03(12) . . ?
C15 C14 C19 119.56(12) . . ?
C19 C14 C13 122.12(12) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.42(12) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.85(12) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 Br1 118.29(10) . . ?
C16 C17 C18 121.86(12) . . ?
C18 C17 Br1 119.84(10) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.59(12) . . ?
C19 C18 H18 120.7 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.61(12) . . ?
C18 C19 H19 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C17 C18 C19 -176.73(10) . . . . ?
O1 C13 C14 C15 -38.09(19) . . . . ?
O1 C13 C14 C19 135.76(14) . . . . ?
N1 C1 C2 C3 -175.13(13) . . . . ?
N1 C1 C6 C5 176.25(11) . . . . ?
N1 C1 C6 C7 1.07(14) . . . . ?
N1 C13 C14 C15 145.01(13) . . . . ?
N1 C13 C14 C19 -41.15(18) . . . . ?
C1 N1 C12 C7 4.37(14) . . . . ?
C1 N1 C12 C11 -176.94(13) . . . . ?
C1 N1 C13 O1 150.89(14) . . . . ?
C1 N1 C13 C14 -32.20(19) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C1 C6 C7 C8 179.47(14) . . . . ?
C1 C6 C7 C12 1.61(14) . . . . ?
C2 C1 C6 C5 1.67(19) . . . . ?
C2 C1 C6 C7 -173.52(12) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.46(19) . . . . ?
C4 C5 C6 C7 173.36(14) . . . . ?
C5 C6 C7 C8 5.1(2) . . . . ?
C5 C6 C7 C12 -172.77(14) . . . . ?
C6 C1 C2 C3 -1.88(19) . . . . ?
C6 C7 C8 C9 -176.76(13) . . . . ?
C6 C7 C12 N1 -3.67(14) . . . . ?
C6 C7 C12 C11 177.52(12) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C7 C12 N1 178.15(11) . . . . ?
C8 C7 C12 C11 -0.66(19) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 N1 -178.55(13) . . . . ?
C10 C11 C12 C7 -0.01(19) . . . . ?
C12 N1 C1 C2 170.63(13) . . . . ?
C12 N1 C1 C6 -3.33(14) . . . . ?
C12 N1 C13 O1 -24.5(2) . . . . ?
C12 N1 C13 C14 152.46(12) . . . . ?
C12 C7 C8 C9 0.88(19) . . . . ?
C13 N1 C1 C2 -5.3(2) . . . . ?
C13 N1 C1 C6 -179.25(12) . . . . ?
C13 N1 C12 C7 -179.47(12) . . . . ?
C13 N1 C12 C11 -0.8(2) . . . . ?
C13 C14 C15 C16 177.19(12) . . . . ?
C13 C14 C19 C18 -175.07(12) . . . . ?
C14 C15 C16 C17 -2.1(2) . . . . ?
C15 C14 C19 C18 -1.3(2) . . . . ?
C15 C16 C17 Br1 178.56(10) . . . . ?
C15 C16 C17 C18 -0.8(2) . . . . ?
C16 C17 C18 C19 2.6(2) . . . . ?
C17 C18 C19 C14 -1.54(19) . . . . ?
C19 C14 C15 C16 3.2(2) . . . . ?

_shelx_SHELXL_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1540850'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;
_audit_creation_date             2017-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H12 Br N O'
_chemical_formula_sum            'C19 H12 Br N O'
_chemical_formula_weight         350.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   8.2389(16)
_cell_length_b                   9.5522(18)
_cell_length_c                   18.470(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.861(5)
_cell_angle_gamma                90
_cell_volume                     1452.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4655
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.601
_shelx_estimated_absorpt_T_min   0.484
_exptl_absorpt_coefficient_mu    2.830
_exptl_absorpt_correction_T_max  0.6014
_exptl_absorpt_correction_T_min  0.4840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14481
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         3.069
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2484
_reflns_number_total             3284
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0742
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.48672(3) 0.67418(2) 1.02215(2) 0.02717(9) Uani 1 1 d . . . . .
O1 O 0.5067(2) 0.84288(19) 0.83001(10) 0.0402(5) Uani 1 1 d . . . . .
N1 N 0.3434(2) 0.65817(19) 0.85330(10) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.4259(3) 0.5571(3) 0.81119(12) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.5779(3) 0.5645(3) 0.78074(13) 0.0335(6) Uani 1 1 d . . . . .
H2 H 0.6404 0.6480 0.7827 0.040 Uiso 1 1 calc R . . . .
C3 C 0.6343(3) 0.4449(4) 0.74741(14) 0.0420(7) Uani 1 1 d . . . . .
H3 H 0.7381 0.4462 0.7265 0.050 Uiso 1 1 calc R . . . .
C4 C 0.5427(4) 0.3234(3) 0.74395(15) 0.0418(7) Uani 1 1 d . . . . .
H4 H 0.5847 0.2433 0.7205 0.050 Uiso 1 1 calc R . . . .
C5 C 0.3917(3) 0.3165(3) 0.77383(14) 0.0335(6) Uani 1 1 d . . . . .
H5 H 0.3297 0.2327 0.7714 0.040 Uiso 1 1 calc R . . . .
C6 C 0.3322(3) 0.4357(2) 0.80774(12) 0.0222(5) Uani 1 1 d . . . . .
C7 C 0.1843(3) 0.4616(2) 0.84588(11) 0.0200(5) Uani 1 1 d . . . . .
C8 C 0.0455(3) 0.3813(3) 0.85496(13) 0.0261(5) Uani 1 1 d . . . . .
H8 H 0.0374 0.2898 0.8351 0.031 Uiso 1 1 calc R . . . .
C9 C -0.0801(3) 0.4369(3) 0.89323(13) 0.0283(6) Uani 1 1 d . . . . .
H9 H -0.1755 0.3831 0.8998 0.034 Uiso 1 1 calc R . . . .
C10 C -0.0685(3) 0.5706(2) 0.92220(13) 0.0258(5) Uani 1 1 d . . . . .
H10 H -0.1564 0.6064 0.9486 0.031 Uiso 1 1 calc R . . . .
C11 C 0.0673(3) 0.6530(2) 0.91383(12) 0.0220(5) Uani 1 1 d . . . . .
H11 H 0.0739 0.7446 0.9338 0.026 Uiso 1 1 calc R . . . .
C12 C 0.1944(3) 0.5972(2) 0.87498(12) 0.0182(5) Uani 1 1 d . . . . .
C13 C 0.4014(3) 0.7923(2) 0.86639(13) 0.0242(5) Uani 1 1 d . . . . .
C14 C 0.3328(3) 0.8736(2) 0.92732(13) 0.0209(5) Uani 1 1 d . . . . .
C15 C 0.2447(3) 0.9957(2) 0.91236(14) 0.0294(6) Uani 1 1 d . . . . .
H15 H 0.2234 1.0235 0.8636 0.035 Uiso 1 1 calc R . . . .
C16 C 0.1883(3) 1.0764(3) 0.96868(15) 0.0326(6) Uani 1 1 d . . . . .
H16 H 0.1262 1.1582 0.9584 0.039 Uiso 1 1 calc R . . . .
C17 C 0.2219(3) 1.0381(3) 1.03931(14) 0.0306(6) Uani 1 1 d . . . . .
H17 H 0.1834 1.0945 1.0775 0.037 Uiso 1 1 calc R . . . .
C18 C 0.3105(3) 0.9195(2) 1.05555(13) 0.0247(5) Uani 1 1 d . . . . .
H18 H 0.3343 0.8944 1.1045 0.030 Uiso 1 1 calc R . . . .
C19 C 0.3647(3) 0.8367(2) 0.99919(13) 0.0206(5) Uani 1 1 d . . . . .


_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 C19 1.890(2) . ?
O1 C13 1.214(3) . ?
N1 C1 1.426(3) . ?
N1 C12 1.428(3) . ?
N1 C13 1.387(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(3) . ?
C6 C7 1.448(3) . ?
C7 C8 1.392(3) . ?
C7 C12 1.404(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(3) . ?
C13 C14 1.494(3) . ?
C14 C15 1.396(3) . ?
C14 C19 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 107.82(17) . . ?
C13 N1 C1 123.58(19) . . ?
C13 N1 C12 128.56(19) . . ?
C2 C1 N1 129.6(2) . . ?
C2 C1 C6 121.9(2) . . ?
C6 C1 N1 108.37(19) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(3) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 C7 108.03(19) . . ?
C5 C6 C7 132.1(2) . . ?
C8 C7 C6 132.3(2) . . ?
C8 C7 C12 120.0(2) . . ?
C12 C7 C6 107.66(19) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.6(2) . . ?
C12 C11 H11 121.2 . . ?
C7 C12 N1 108.05(18) . . ?
C11 C12 N1 130.9(2) . . ?
C11 C12 C7 120.9(2) . . ?
O1 C13 N1 121.3(2) . . ?
O1 C13 C14 120.3(2) . . ?
N1 C13 C14 118.36(19) . . ?
C15 C14 C13 119.5(2) . . ?
C19 C14 C13 121.5(2) . . ?
C19 C14 C15 118.8(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.1(2) . . ?
C19 C18 H18 120.5 . . ?
C14 C19 Br1 120.36(17) . . ?
C14 C19 C18 120.9(2) . . ?
C18 C19 Br1 118.69(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
O1 C13 C14 C15 65.3(3) . . . . ?
O1 C13 C14 C19 -109.8(3) . . . . ?
N1 C1 C2 C3 174.5(2) . . . . ?
N1 C1 C6 C5 -175.4(2) . . . . ?
N1 C1 C6 C7 2.2(3) . . . . ?
N1 C13 C14 C15 -115.5(2) . . . . ?
N1 C13 C14 C19 69.5(3) . . . . ?
C1 N1 C12 C7 -0.8(2) . . . . ?
C1 N1 C12 C11 -176.9(2) . . . . ?
C1 N1 C13 O1 16.7(4) . . . . ?
C1 N1 C13 C14 -162.5(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C6 C7 C8 175.0(2) . . . . ?
C1 C6 C7 C12 -2.7(3) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C2 C1 C6 C7 178.5(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 -177.5(3) . . . . ?
C5 C6 C7 C8 -7.8(4) . . . . ?
C5 C6 C7 C12 174.5(2) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C6 C7 C8 C9 -178.1(2) . . . . ?
C6 C7 C12 N1 2.2(2) . . . . ?
C6 C7 C12 C11 178.8(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C7 C12 N1 -175.9(2) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 N1 175.4(2) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C12 N1 C1 C2 -176.8(2) . . . . ?
C12 N1 C1 C6 -0.9(3) . . . . ?
C12 N1 C13 O1 -160.4(2) . . . . ?
C12 N1 C13 C14 20.3(4) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
C13 N1 C1 C2 5.5(4) . . . . ?
C13 N1 C1 C6 -178.6(2) . . . . ?
C13 N1 C12 C7 176.7(2) . . . . ?
C13 N1 C12 C11 0.6(4) . . . . ?
C13 C14 C15 C16 -176.3(2) . . . . ?
C13 C14 C19 Br1 -3.8(3) . . . . ?
C13 C14 C19 C18 175.0(2) . . . . ?
C14 C15 C16 C17 1.4(4) . . . . ?
C15 C14 C19 Br1 -178.90(17) . . . . ?
C15 C14 C19 C18 -0.1(3) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 Br1 179.86(18) . . . . ?
C17 C18 C19 C14 1.1(3) . . . . ?
C19 C14 C15 C16 -1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  dichloromethane/ethanol'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1534317'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 Br N O'
_chemical_formula_weight         350.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   21.5976(18)
_cell_length_b                   7.7186(4)
_cell_length_c                   18.3872(16)
_cell_angle_alpha                90
_cell_angle_beta                 110.435(10)
_cell_angle_gamma                90
_cell_volume                     2872.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2402
_cell_measurement_theta_min      3.2670
_cell_measurement_theta_max      28.4430

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.863
_shelx_estimated_absorpt_T_min   0.763
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_reflns_number            7923
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.892
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3146
_reflns_number_gt                2185
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+4.1263P] 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         3146
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.057
_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 0.80985(2) -0.24911(5) 0.60614(3) 0.0325(2) Uani 1 1 d . . . . .
C1 C 0.6338(2) 0.2726(5) 0.8396(2) 0.0173(8) Uani 1 1 d . . . . .
C2 C 0.6722(2) 0.2480(5) 0.9176(3) 0.0219(9) Uani 1 1 d . . . . .
H2A H 0.7113 0.1800 0.9326 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6507(2) 0.3272(6) 0.9723(3) 0.0272(10) Uani 1 1 d . . . . .
H3A H 0.6758 0.3135 1.0259 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5933(2) 0.4261(6) 0.9503(3) 0.0266(10) Uani 1 1 d . . . . .
H4A H 0.5802 0.4793 0.9892 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5553(2) 0.4485(5) 0.8736(3) 0.0229(9) Uani 1 1 d . . . . .
H5A H 0.5161 0.5158 0.8593 0.027 Uiso 1 1 calc R U . . .
C6 C 0.57540(19) 0.3707(5) 0.8171(2) 0.0186(8) Uani 1 1 d . . . . .
C7 C 0.54765(19) 0.3671(5) 0.7334(2) 0.0202(9) Uani 1 1 d . . . . .
C8 C 0.59055(19) 0.2684(5) 0.7068(2) 0.0162(8) Uani 1 1 d . . . . .
C9 C 0.5798(2) 0.2510(5) 0.6282(2) 0.0203(9) Uani 1 1 d . . . . .
H9A H 0.6099 0.1887 0.6107 0.024 Uiso 1 1 calc R U . . .
C10 C 0.5233(2) 0.3285(5) 0.5756(3) 0.0255(10) Uani 1 1 d . . . . .
H10A H 0.5149 0.3184 0.5215 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4790(2) 0.4200(5) 0.6011(3) 0.0263(10) Uani 1 1 d . . . . .
H11A H 0.4401 0.4677 0.5642 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4913(2) 0.4422(5) 0.6797(3) 0.0244(9) Uani 1 1 d . . . . .
H12A H 0.4618 0.5077 0.6969 0.029 Uiso 1 1 calc R U . . .
C13 C 0.6993(2) 0.1101(5) 0.7734(2) 0.0192(9) Uani 1 1 d . . . . .
C14 C 0.6896(2) -0.0268(5) 0.7129(2) 0.0197(9) Uani 1 1 d . . . . .
C15 C 0.6327(2) -0.1257(5) 0.6864(3) 0.0234(9) Uani 1 1 d . . . . .
H15A H 0.5975 -0.1006 0.7044 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6258(3) -0.2593(5) 0.6348(3) 0.0263(9) Uani 1 1 d . U . . .
H16A H 0.5863 -0.3260 0.6169 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6795(2) -0.2951(6) 0.6089(3) 0.0278(10) Uani 1 1 d . U . . .
H17A H 0.6762 -0.3865 0.5731 0.033 Uiso 1 1 calc R U . . .
C18 C 0.7361(2) -0.1963(5) 0.6361(3) 0.0226(9) Uani 1 1 d . . . . .
C19 C 0.7426(2) -0.0636(5) 0.6888(2) 0.0223(9) Uani 1 1 d . . . . .
H19A H 0.7825 0.0011 0.7083 0.027 Uiso 1 1 calc R U . . .
N1 N 0.64283(16) 0.2050(4) 0.7722(2) 0.0182(7) Uani 1 1 d . . . . .
O1 O 0.75223(14) 0.1368(4) 0.82447(17) 0.0242(7) Uani 1 1 d . . . . .


_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 C18 1.903(4) . ?
C1 C2 1.396(6) . ?
C1 C6 1.404(5) . ?
C1 N1 1.419(5) . ?
C2 C3 1.387(6) . ?
C3 C4 1.391(6) . ?
C4 C5 1.372(6) . ?
C5 C6 1.394(5) . ?
C6 C7 1.443(6) . ?
C7 C12 1.397(6) . ?
C7 C8 1.412(5) . ?
C8 C9 1.388(6) . ?
C8 N1 1.419(5) . ?
C9 C10 1.400(6) . ?
C10 C11 1.395(6) . ?
C11 C12 1.387(6) . ?
C13 O1 1.217(5) . ?
C13 N1 1.417(5) . ?
C13 C14 1.494(6) . ?
C14 C15 1.383(6) . ?
C14 C19 1.393(5) . ?
C15 C16 1.374(6) . ?
C16 C17 1.426(7) . ?
C17 C18 1.379(6) . ?
C18 C19 1.383(6) . ?

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 C1 C6 121.7(4) . . ?
C2 C1 N1 129.3(4) . . ?
C6 C1 N1 108.9(4) . . ?
C3 C2 C1 117.1(4) . . ?
C2 C3 C4 121.4(4) . . ?
C5 C4 C3 121.4(4) . . ?
C4 C5 C6 118.8(4) . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 C7 133.0(4) . . ?
C1 C6 C7 107.5(3) . . ?
C12 C7 C8 119.6(4) . . ?
C12 C7 C6 132.9(4) . . ?
C8 C7 C6 107.5(4) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 N1 130.0(4) . . ?
C7 C8 N1 108.5(3) . . ?
C8 C9 C10 117.8(4) . . ?
C11 C10 C9 121.3(4) . . ?
C12 C11 C10 120.5(4) . . ?
C11 C12 C7 119.2(4) . . ?
O1 C13 N1 119.7(4) . . ?
O1 C13 C14 123.0(3) . . ?
N1 C13 C14 117.3(4) . . ?
C15 C14 C19 120.2(4) . . ?
C15 C14 C13 121.9(3) . . ?
C19 C14 C13 117.6(4) . . ?
C16 C15 C14 121.8(4) . . ?
C15 C16 C17 118.1(4) . . ?
C18 C17 C16 119.6(4) . . ?
C17 C18 C19 121.7(4) . . ?
C17 C18 Br1 120.2(3) . . ?
C19 C18 Br1 118.1(3) . . ?
C18 C19 C14 118.6(4) . . ?
C13 N1 C8 128.1(3) . . ?
C13 N1 C1 123.8(3) . . ?
C8 N1 C1 107.6(3) . . ?

_refine_diff_density_max         1.758
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.108

