# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2b_PkB
_database_code_depnum_ccdc_archive 'CCDC 1470107'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_audit_creation_date             2012-11-05
_audit_creation_method           
;
  Olex2 1.2
  (compiled Oct 26 2012 17:06:22, GUI svn.r4371)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y+1/2, -z'
3 '-x, y+1/2, -z+1/2'
4 '-x+1/2, -y, z+1/2'

_cell_length_a                   7.9650(2)
_cell_length_b                   9.5073(2)
_cell_length_c                   16.0506(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1215.44(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6398
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.14
_cell_measurement_theta_min      5.41
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0396 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.9057.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9006
_diffrn_reflns_theta_full        69.61
_diffrn_reflns_theta_max         69.61
_diffrn_reflns_theta_min         5.41
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                2165
_reflns_number_total             2206
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(19)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0335P)²+0.2706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0661
_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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H13 of C13, H3 of C3, {H15A,H15B} of C15, H11 of C11, {H10A,H10B} of C10,
  H8 of C8, H7 of C7
 At 1.5 times of:
  {H12A,H12B,H12C} of C12, {H1A,H1B,H1C} of C1
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C13(H13)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O1 O 1.11934(11) 0.22294(9) 0.21049(6) 0.0227(2) Uani 1 1 d . . .
O2 O 1.01583(12) -0.23706(10) 0.02340(5) 0.0259(2) Uani 1 1 d . . .
N1 N 0.89084(13) 0.11261(11) 0.15389(6) 0.0172(2) Uani 1 1 d . . .
C1 C 1.24924(16) -0.25363(13) 0.15040(8) 0.0216(3) Uani 1 1 d . . .
H1A H 1.3320 -0.2319 0.1937 0.032 Uiso 1 1 calc R . .
H1B H 1.3059 -0.2612 0.0964 0.032 Uiso 1 1 calc R . .
H1C H 1.1938 -0.3430 0.1635 0.032 Uiso 1 1 calc R . .
C2 C 1.12026(16) -0.13820(13) 0.14667(7) 0.0173(3) Uani 1 1 d . . .
C3 C 1.13906(15) -0.02122(14) 0.19269(8) 0.0184(3) Uani 1 1 d . . .
H3 H 1.2226 -0.0264 0.2348 0.022 Uiso 1 1 calc R . .
C4 C 1.04852(15) 0.11508(13) 0.18741(7) 0.0168(2) Uani 1 1 d . . .
C5 C 0.79140(15) 0.23065(13) 0.13127(7) 0.0173(3) Uani 1 1 d . . .
C6 C 0.84336(16) 0.35689(13) 0.09438(8) 0.0196(3) Uani 1 1 d . . .
C7 C 0.71603(17) 0.45427(14) 0.07741(8) 0.0235(3) Uani 1 1 d . . .
H7 H 0.7454 0.5421 0.0532 0.028 Uiso 1 1 calc R . .
C8 C 0.54762(17) 0.42702(14) 0.09473(9) 0.0252(3) Uani 1 1 d . . .
H8 H 0.4655 0.4974 0.0845 0.030 Uiso 1 1 calc R . .
C9 C 0.98311(16) -0.16566(12) 0.08424(8) 0.0188(3) Uani 1 1 d . . .
C10 C 0.80489(16) -0.11584(14) 0.09785(8) 0.0213(3) Uani 1 1 d . . .
H10A H 0.7643 -0.0719 0.0457 0.026 Uiso 1 1 calc R . .
H10B H 0.7333 -0.1989 0.1089 0.026 Uiso 1 1 calc R . .
C11 C 0.78204(15) -0.01213(13) 0.16818(8) 0.0178(3) Uani 1 1 d . . .
H11 H 0.8124 -0.0576 0.2223 0.021 Uiso 1 1 calc R . .
C12 C 1.02124(17) 0.38836(14) 0.06908(9) 0.0241(3) Uani 1 1 d . . .
H12A H 1.0861 0.4164 0.1182 0.036 Uiso 1 1 calc R . .
H12B H 1.0219 0.4650 0.0282 0.036 Uiso 1 1 calc R . .
H12C H 1.0717 0.3042 0.0443 0.036 Uiso 1 1 calc R . .
C13 C 0.49910(16) 0.29743(14) 0.12685(8) 0.0227(3) Uani 1 1 d . . .
H13 H 0.3841 0.2770 0.1369 0.027 Uiso 1 1 calc R . .
C14 C 0.62212(16) 0.19928(13) 0.14368(8) 0.0185(3) Uani 1 1 d . . .
C15 C 0.60274(16) 0.04946(14) 0.17368(8) 0.0195(3) Uani 1 1 d . . .
H15A H 0.5243 -0.0035 0.1376 0.023 Uiso 1 1 calc R . .
H15B H 0.5607 0.0469 0.2317 0.023 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
O1 C4 1.2276(15) . ?
O2 C9 1.2175(15) . ?
N1 C4 1.3666(16) . ?
N1 C5 1.4207(16) . ?
N1 C11 1.4866(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5044(17) . ?
C2 C3 1.3434(18) . ?
C2 C9 1.5052(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.4854(18) . ?
C5 C6 1.4008(17) . ?
C5 C14 1.3952(17) . ?
C6 C7 1.4000(18) . ?
C6 C12 1.5040(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.394(2) . ?
C8 H8 0.9500 . ?
C8 C13 1.3904(19) . ?
C9 C10 1.5123(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5099(17) . ?
C11 H11 1.0000 . ?
C11 C15 1.5461(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.3798(18) . ?
C14 C15 1.5115(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C4 N1 C5 126.82(11) . . ?
C4 N1 C11 119.25(10) . . ?
C5 N1 C11 110.16(9) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 C9 113.30(10) . . ?
C3 C2 C1 120.39(11) . . ?
C3 C2 C9 126.19(11) . . ?
C2 C3 H3 115.2 . . ?
C2 C3 C4 129.55(11) . . ?
C4 C3 H3 115.2 . . ?
O1 C4 N1 123.75(12) . . ?
O1 C4 C3 119.24(11) . . ?
N1 C4 C3 116.97(11) . . ?
C6 C5 N1 128.32(11) . . ?
C14 C5 N1 109.48(11) . . ?
C14 C5 C6 121.93(11) . . ?
C5 C6 C12 124.25(11) . . ?
C7 C6 C5 115.78(11) . . ?
C7 C6 C12 119.89(12) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.36(12) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 H8 119.8 . . ?
C13 C8 C7 120.40(12) . . ?
C13 C8 H8 119.8 . . ?
O2 C9 C2 118.38(11) . . ?
O2 C9 C10 119.43(11) . . ?
C2 C9 C10 122.06(11) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.19(10) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
N1 C11 C10 109.59(10) . . ?
N1 C11 H11 109.7 . . ?
N1 C11 C15 104.19(9) . . ?
C10 C11 H11 109.7 . . ?
C10 C11 C15 113.66(10) . . ?
C15 C11 H11 109.7 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13 120.8 . . ?
C14 C13 C8 118.32(12) . . ?
C14 C13 H13 120.8 . . ?
C5 C14 C15 110.22(11) . . ?
C13 C14 C5 120.92(12) . . ?
C13 C14 C15 128.84(12) . . ?
C11 C15 H15A 110.9 . . ?
C11 C15 H15B 110.9 . . ?
C14 C15 C11 104.15(10) . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?

####################################################################### 
# 
# 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_2b_PkA
_database_code_depnum_ccdc_archive 'CCDC 1470108'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_audit_creation_date             2012-11-02
_audit_creation_method           
;
  Olex2 1.2
  (compiled Oct 26 2012 17:06:22, GUI svn.r4371)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y+1/2, -z'
3 '-x, y+1/2, -z+1/2'
4 '-x+1/2, -y, z+1/2'

_cell_length_a                   7.9647(2)
_cell_length_b                   9.5076(3)
_cell_length_c                   16.0492(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1215.33(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5538
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.73
_cell_measurement_theta_min      5.41
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0551 before and 0.0351 after correction.
The Ratio of minimum to maximum transmission is 0.9158.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7249
_diffrn_reflns_theta_full        67.72
_diffrn_reflns_theta_max         67.72
_diffrn_reflns_theta_min         5.41
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                2077
_reflns_number_total             2119
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.16(19)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.2026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0684
_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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H8 of C8, {H6A,H6B} of C6, {H4A,H4B} of C4, H5 of C5, H10 of
  C10, H9 of C9
 At 1.5 times of:
  {H14A,H14B,H14C} of C14, {H1A,H1B,H1C} of C1
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O1 O 0.11938(12) -0.72296(9) -0.78950(6) 0.0218(2) Uani 1 1 d . . .
O2 O 0.01590(13) -0.26297(10) -0.97666(5) 0.0252(2) Uani 1 1 d . . .
N1 N -0.10901(14) -0.61267(11) -0.84605(6) 0.0160(2) Uani 1 1 d . . .
C1 C 0.24911(17) -0.24649(13) -0.84969(8) 0.0206(3) Uani 1 1 d . . .
H1A H 0.3055 -0.2387 -0.9038 0.031 Uiso 1 1 calc R . .
H1B H 0.3321 -0.2684 -0.8065 0.031 Uiso 1 1 calc R . .
H1C H 0.1938 -0.1572 -0.8364 0.031 Uiso 1 1 calc R . .
C2 C 0.12029(17) -0.36175(13) -0.85332(7) 0.0169(3) Uani 1 1 d . . .
C3 C -0.01697(17) -0.33458(12) -0.91572(8) 0.0178(3) Uani 1 1 d . . .
C4 C -0.19499(17) -0.38419(13) -0.90217(8) 0.0204(3) Uani 1 1 d . . .
H4A H -0.2356 -0.4282 -0.9543 0.024 Uiso 1 1 calc R . .
H4B H -0.2665 -0.3011 -0.8911 0.024 Uiso 1 1 calc R . .
C5 C -0.21790(16) -0.48789(13) -0.83178(8) 0.0166(3) Uani 1 1 d . . .
H5 H -0.1877 -0.4424 -0.7776 0.020 Uiso 1 1 calc R . .
C6 C -0.39733(17) -0.54935(13) -0.82650(8) 0.0186(3) Uani 1 1 d . . .
H6A H -0.4398 -0.5466 -0.7685 0.022 Uiso 1 1 calc R . .
H6B H -0.4755 -0.4965 -0.8628 0.022 Uiso 1 1 calc R . .
C7 C -0.37757(17) -0.69918(13) -0.85629(8) 0.0175(3) Uani 1 1 d . . .
C8 C -0.50079(17) -0.79724(14) -0.87311(8) 0.0220(3) Uani 1 1 d . . .
H8 H -0.6157 -0.7767 -0.8630 0.026 Uiso 1 1 calc R . .
C9 C -0.45231(19) -0.92709(14) -0.90534(9) 0.0245(3) Uani 1 1 d . . .
H9 H -0.5344 -0.9974 -0.9156 0.029 Uiso 1 1 calc R . .
C10 C 0.13923(16) -0.47875(14) -0.80732(8) 0.0176(3) Uani 1 1 d . . .
H10 H 0.2229 -0.4736 -0.7652 0.021 Uiso 1 1 calc R . .
C11 C 0.04855(16) -0.61504(13) -0.81265(7) 0.0163(3) Uani 1 1 d . . .
C12 C -0.28439(19) -0.95419(13) -0.92252(8) 0.0226(3) Uani 1 1 d . . .
H12 H -0.2551 -1.0421 -0.9467 0.027 Uiso 1 1 calc R . .
C13 C -0.15646(17) -0.85705(13) -0.90561(8) 0.0189(3) Uani 1 1 d . . .
C14 C 0.02087(18) -0.88837(14) -0.93081(9) 0.0236(3) Uani 1 1 d . . .
H14A H 0.0215 -0.9649 -0.9717 0.035 Uiso 1 1 calc R . .
H14B H 0.0856 -0.9166 -0.8817 0.035 Uiso 1 1 calc R . .
H14C H 0.0714 -0.8041 -0.9555 0.035 Uiso 1 1 calc R . .
C15 C -0.20852(16) -0.73056(12) -0.86870(7) 0.0165(3) 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
O1 C11 1.2285(16) . ?
O2 C3 1.2201(15) . ?
N1 C5 1.4873(15) . ?
N1 C11 1.3648(17) . ?
N1 C15 1.4200(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5023(18) . ?
C2 C3 1.5049(18) . ?
C2 C10 1.3436(18) . ?
C3 C4 1.5100(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5105(17) . ?
C5 H5 1.0000 . ?
C5 C6 1.5462(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5109(18) . ?
C7 C8 1.3803(19) . ?
C7 C15 1.3934(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(2) . ?
C9 H9 0.9500 . ?
C9 C12 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.4859(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.4017(19) . ?
C13 C14 1.499(2) . ?
C13 C15 1.4032(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C11 N1 C5 119.26(10) . . ?
C11 N1 C15 126.92(11) . . ?
C15 N1 C5 110.10(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 C3 113.37(10) . . ?
C10 C2 C1 120.39(12) . . ?
C10 C2 C3 126.11(12) . . ?
O2 C3 C2 118.25(12) . . ?
O2 C3 C4 119.42(12) . . ?
C2 C3 C4 122.19(11) . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C3 C4 C5 115.15(11) . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
N1 C5 C4 109.58(10) . . ?
N1 C5 H5 109.8 . . ?
N1 C5 C6 104.24(9) . . ?
C4 C5 H5 109.8 . . ?
C4 C5 C6 113.53(11) . . ?
C6 C5 H5 109.8 . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
C7 C6 C5 104.04(10) . . ?
C7 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
C8 C7 C6 128.66(13) . . ?
C8 C7 C15 120.96(12) . . ?
C15 C7 C6 110.35(11) . . ?
C7 C8 H8 120.9 . . ?
C7 C8 C9 118.30(13) . . ?
C9 C8 H8 120.9 . . ?
C8 C9 H9 119.8 . . ?
C12 C9 C8 120.32(12) . . ?
C12 C9 H9 119.8 . . ?
C2 C10 H10 115.3 . . ?
C2 C10 C11 129.48(12) . . ?
C11 C10 H10 115.3 . . ?
O1 C11 N1 123.69(12) . . ?
O1 C11 C10 119.19(11) . . ?
N1 C11 C10 117.08(11) . . ?
C9 C12 H12 118.7 . . ?
C9 C12 C13 122.61(12) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 C14 120.12(12) . . ?
C12 C13 C15 115.57(12) . . ?
C15 C13 C14 124.23(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 N1 109.49(10) . . ?
C7 C15 C13 121.96(12) . . ?
C13 C15 N1 128.29(12) . . ?

####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1470109'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_audit_creation_date             2014-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H12 Br N O2'
_chemical_formula_sum            'C14 H12 Br N O2'
_chemical_formula_weight         306.16
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.5431(8)
_cell_length_b                   9.8089(8)
_cell_length_c                   14.6636(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1228.79(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4182
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.338
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0634 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.8465.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9446
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.089
_diffrn_reflns_theta_min         2.498
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2542
_reflns_number_total             2719
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.417(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0204
_refine_ls_restrained_S_all      1.040
_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)+(0.0203P)²+0.1990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0436
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.26017(3) 1.22124(3) 0.36424(2) 0.01455(8) Uani 1 1 d . . . . .
O1 O 0.3129(2) 1.2724(2) 0.70680(13) 0.0190(4) Uani 1 1 d . . . . .
O2 O 0.0588(2) 0.99782(19) 0.44981(12) 0.0141(4) Uani 1 1 d . . . . .
N1 N 0.2232(3) 0.9430(2) 0.56801(14) 0.0098(5) Uani 1 1 d . . . . .
C1 C 0.0658(4) 0.5675(3) 0.66468(19) 0.0166(7) Uani 1 1 d . . . . .
H1 H 0.0355 0.4783 0.6828 0.020 Uiso 1 1 calc R . . . .
C2 C 0.2248(4) 0.6014(3) 0.66071(16) 0.0142(6) Uani 1 1 d . . . . .
H2 H 0.3028 0.5378 0.6787 0.017 Uiso 1 1 calc R . . . .
C3 C 0.2653(3) 0.7304(2) 0.62981(15) 0.0113(5) Uani 1 1 d . . . . .
C4 C 0.4250(3) 0.7955(3) 0.62332(18) 0.0106(6) Uani 1 1 d . . . . .
H4A H 0.4890 0.7509 0.5756 0.013 Uiso 1 1 calc R . . . .
H4B H 0.4809 0.7897 0.6823 0.013 Uiso 1 1 calc R . . . .
C5 C 0.3902(3) 0.9451(3) 0.59809(19) 0.0106(6) Uani 1 1 d . . . . .
H5 H 0.4587 0.9739 0.5462 0.013 Uiso 1 1 calc R . . . .
C6 C 0.4040(3) 1.0470(3) 0.67566(19) 0.0141(6) Uani 1 1 d . . . . .
H6A H 0.3437 1.0131 0.7287 0.017 Uiso 1 1 calc R . . . .
H6B H 0.5151 1.0540 0.6942 0.017 Uiso 1 1 calc R . . . .
C7 C 0.3448(3) 1.1870(3) 0.65000(18) 0.0114(6) Uani 1 1 d . . . . .
C8 C 0.3332(3) 1.2264(3) 0.55085(17) 0.0134(6) Uani 1 1 d . . . . .
H8 H 0.3779 1.3111 0.5335 0.016 Uiso 1 1 calc R . . . .
C9 C -0.0477(3) 0.6626(3) 0.64239(19) 0.0151(6) Uani 1 1 d . . . . .
H9 H -0.1548 0.6381 0.6485 0.018 Uiso 1 1 calc R . . . .
C10 C -0.0104(3) 0.7942(3) 0.61104(17) 0.0117(6) Uani 1 1 d . . . . .
C11 C 0.1493(3) 0.8215(3) 0.60037(18) 0.0105(6) Uani 1 1 d . . . . .
C12 C 0.2655(4) 1.1525(2) 0.48539(15) 0.0107(5) Uani 1 1 d . . . . .
C13 C 0.1726(3) 1.0226(3) 0.49733(17) 0.0112(6) Uani 1 1 d . . . . .
C14 C -0.1370(3) 0.8994(3) 0.5978(2) 0.0165(6) Uani 1 1 d . . . . .
H14A H -0.0988 0.9886 0.6180 0.025 Uiso 1 1 calc GR . . . .
H14B H -0.2292 0.8739 0.6336 0.025 Uiso 1 1 calc GR . . . .
H14C H -0.1652 0.9040 0.5330 0.025 Uiso 1 1 calc GR . . . .


_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 C12 1.901(2) . ?
O1 C7 1.212(3) . ?
O2 C13 1.221(3) . ?
N1 C5 1.493(3) . ?
N1 C11 1.429(3) . ?
N1 C13 1.368(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.399(4) . ?
C1 C9 1.385(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(4) . ?
C3 C4 1.509(3) . ?
C3 C11 1.402(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.542(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.519(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.511(4) . ?
C7 C8 1.508(4) . ?
C8 H8 0.9500 . ?
C8 C12 1.334(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.407(4) . ?
C10 C11 1.400(4) . ?
C10 C14 1.507(4) . ?
C12 C13 1.512(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C11 N1 C5 109.6(2) . . ?
C13 N1 C5 121.2(2) . . ?
C13 N1 C11 126.0(2) . . ?
C2 C1 H1 119.7 . . ?
C9 C1 H1 119.7 . . ?
C9 C1 C2 120.6(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 129.2(2) . . ?
C2 C3 C11 120.4(3) . . ?
C11 C3 C4 110.4(2) . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C3 C4 C5 104.1(2) . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
N1 C5 C4 104.0(2) . . ?
N1 C5 H5 109.8 . . ?
N1 C5 C6 107.7(2) . . ?
C4 C5 H5 109.8 . . ?
C6 C5 C4 115.6(2) . . ?
C6 C5 H5 109.8 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.7(2) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
O1 C7 C6 122.2(2) . . ?
O1 C7 C8 118.1(3) . . ?
C8 C7 C6 119.7(2) . . ?
C7 C8 H8 117.2 . . ?
C12 C8 C7 125.7(3) . . ?
C12 C8 H8 117.2 . . ?
C1 C9 H9 118.8 . . ?
C1 C9 C10 122.4(3) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C14 120.5(2) . . ?
C11 C10 C9 115.6(3) . . ?
C11 C10 C14 123.7(3) . . ?
C3 C11 N1 108.8(2) . . ?
C10 C11 N1 128.8(3) . . ?
C10 C11 C3 122.2(3) . . ?
C8 C12 Br1 119.4(2) . . ?
C8 C12 C13 127.0(2) . . ?
C13 C12 Br1 113.25(17) . . ?
O2 C13 N1 124.8(3) . . ?
O2 C13 C12 121.3(2) . . ?
N1 C13 C12 113.8(2) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Br1 C12 C13 O2 -28.9(3) . . . . ?
Br1 C12 C13 N1 154.53(19) . . . . ?
O1 C7 C8 C12 -134.0(3) . . . . ?
N1 C5 C6 C7 -55.5(3) . . . . ?
C1 C2 C3 C4 176.5(2) . . . . ?
C1 C2 C3 C11 -2.3(4) . . . . ?
C1 C9 C10 C11 2.4(4) . . . . ?
C1 C9 C10 C14 -173.1(3) . . . . ?
C2 C1 C9 C10 3.0(4) . . . . ?
C2 C3 C4 C5 -171.7(2) . . . . ?
C2 C3 C11 N1 -177.0(2) . . . . ?
C2 C3 C11 C10 8.0(4) . . . . ?
C3 C4 C5 N1 -14.9(3) . . . . ?
C3 C4 C5 C6 103.0(2) . . . . ?
C4 C3 C11 N1 4.0(3) . . . . ?
C4 C3 C11 C10 -171.0(2) . . . . ?
C4 C5 C6 C7 -171.2(2) . . . . ?
C5 N1 C11 C3 -14.2(3) . . . . ?
C5 N1 C11 C10 160.3(3) . . . . ?
C5 N1 C13 O2 155.0(3) . . . . ?
C5 N1 C13 C12 -28.6(3) . . . . ?
C5 C6 C7 O1 162.9(3) . . . . ?
C5 C6 C7 C8 -20.8(3) . . . . ?
C6 C7 C8 C12 49.6(4) . . . . ?
C7 C8 C12 Br1 179.1(2) . . . . ?
C7 C8 C12 C13 6.7(5) . . . . ?
C8 C12 C13 O2 143.9(3) . . . . ?
C8 C12 C13 N1 -32.7(4) . . . . ?
C9 C1 C2 C3 -3.0(4) . . . . ?
C9 C10 C11 N1 178.3(2) . . . . ?
C9 C10 C11 C3 -7.8(4) . . . . ?
C11 N1 C5 C4 18.1(3) . . . . ?
C11 N1 C5 C6 -105.0(3) . . . . ?
C11 N1 C13 O2 -2.5(4) . . . . ?
C11 N1 C13 C12 173.9(2) . . . . ?
C11 C3 C4 C5 7.2(3) . . . . ?
C13 N1 C5 C4 -142.7(2) . . . . ?
C13 N1 C5 C6 94.1(3) . . . . ?
C13 N1 C11 C3 145.5(2) . . . . ?
C13 N1 C11 C10 -40.0(4) . . . . ?
C14 C10 C11 N1 -6.4(4) . . . . ?
C14 C10 C11 C3 167.5(2) . . . . ?

_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_2f
_database_code_depnum_ccdc_archive 'CCDC 1470110'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_audit_creation_date             2015-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O3'
_chemical_formula_sum            'C15 H15 N O3'
_chemical_formula_weight         257.28
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   16.9222(7)
_cell_length_b                   7.6509(3)
_cell_length_c                   20.5384(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.285(2)
_cell_angle_gamma                90
_cell_volume                     2509.90(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7193
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.548
_cell_measurement_theta_min      5.540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.9033.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.045
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15458
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.763
_diffrn_reflns_theta_min         5.539
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3820
_reflns_number_total             4309
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.1101
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+29.5786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2873
_refine_ls_wR_factor_ref         0.2902
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C25(H25A,H25B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C15(H15), C18(H18), C22(H22), C23(H23), C29(H29)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C30(H30A,H30B,H30C)
;
_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
O1 O 0.7204(2) 0.9272(5) 0.0498(2) 0.0217(9) Uani 1 1 d . . . . .
O2 O 0.7476(3) 0.8783(6) 0.1862(2) 0.0287(11) Uani 1 1 d . . . . .
O3 O 0.4579(2) 0.6844(5) 0.0306(2) 0.0230(10) Uani 1 1 d . . . . .
O4 O 1.1847(2) 0.5746(6) -0.0566(2) 0.0227(10) Uani 1 1 d . . . . .
O5 O 0.9407(2) 0.8072(5) -0.0275(2) 0.0215(10) Uani 1 1 d . . . . .
O6 O 1.0970(3) 0.6394(6) -0.1919(2) 0.0324(11) Uani 1 1 d . . . . .
N1 N 0.5691(3) 0.5417(6) 0.1056(2) 0.0184(11) Uani 1 1 d . . . . .
N2 N 0.9882(3) 0.9578(6) -0.1032(2) 0.0176(10) Uani 1 1 d . . . . .
C1 C 0.6867(4) 0.9997(9) -0.0186(3) 0.0268(14) Uani 1 1 d . . . . .
H1A H 0.6696 0.9066 -0.0516 0.040 Uiso 1 1 calc GR . . . .
H1B H 0.7288 1.0689 -0.0283 0.040 Uiso 1 1 calc GR . . . .
H1C H 0.6393 1.0718 -0.0213 0.040 Uiso 1 1 calc GR . . . .
C2 C 0.6696(4) 0.8185(7) 0.0702(3) 0.0187(12) Uani 1 1 d . . . . .
C3 C 0.7146(4) 0.7650(8) 0.1446(3) 0.0186(12) Uani 1 1 d . . . . .
C4 C 0.7185(4) 0.5744(8) 0.1639(3) 0.0195(13) Uani 1 1 d . . . . .
H4A H 0.7735 0.5290 0.1680 0.023 Uiso 1 1 calc R . . . .
H4B H 0.7110 0.5630 0.2085 0.023 Uiso 1 1 calc R . . . .
C5 C 0.6533(3) 0.4679(7) 0.1120(3) 0.0180(12) Uani 1 1 d . . . . .
H5 H 0.6622 0.4733 0.0672 0.022 Uiso 1 1 calc R . . . .
C6 C 0.6487(4) 0.2751(8) 0.1329(3) 0.0236(13) Uani 1 1 d . . . . .
H6A H 0.6482 0.1970 0.0956 0.028 Uiso 1 1 calc R . . . .
H6B H 0.6959 0.2457 0.1734 0.028 Uiso 1 1 calc R . . . .
C7 C 0.5678(4) 0.2637(8) 0.1481(3) 0.0201(12) Uani 1 1 d . . . . .
C8 C 0.5359(4) 0.1246(8) 0.1749(3) 0.0253(14) Uani 1 1 d . . . . .
H8 H 0.5628 0.0167 0.1829 0.030 Uiso 1 1 calc R . . . .
C9 C 0.4619(4) 0.1525(9) 0.1896(3) 0.0291(15) Uani 1 1 d . . . . .
H9 H 0.4375 0.0600 0.2054 0.035 Uiso 1 1 calc R . . . .
C10 C 0.5253(3) 0.4235(8) 0.1338(3) 0.0194(12) Uani 1 1 d . . . . .
C11 C 0.4247(4) 0.3133(9) 0.1811(3) 0.0263(14) Uani 1 1 d . . . . .
H11 H 0.3770 0.3283 0.1935 0.032 Uiso 1 1 calc R . . . .
C12 C 0.4559(4) 0.4572(8) 0.1542(3) 0.0226(13) Uani 1 1 d . . . . .
C13 C 0.4205(4) 0.6364(8) 0.1558(3) 0.0264(14) Uani 1 1 d . . . . .
H13A H 0.4649 0.7210 0.1668 0.040 Uiso 1 1 calc GR . . . .
H13B H 0.3934 0.6400 0.1901 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.3805 0.6629 0.1114 0.040 Uiso 1 1 calc GR . . . .
C14 C 0.5334(3) 0.6652(7) 0.0553(3) 0.0181(12) Uani 1 1 d . . . . .
C15 C 0.5915(4) 0.7752(8) 0.0326(3) 0.0212(13) Uani 1 1 d . . . . .
H15 H 0.5717 0.8181 -0.0123 0.025 Uiso 1 1 calc R . . . .
C16 C 1.2093(4) 0.4988(9) 0.0108(3) 0.0263(14) Uani 1 1 d . . . . .
H16A H 1.2194 0.5899 0.0447 0.039 Uiso 1 1 calc GR . . . .
H16B H 1.2596 0.4320 0.0184 0.039 Uiso 1 1 calc GR . . . .
H16C H 1.1656 0.4237 0.0145 0.039 Uiso 1 1 calc GR . . . .
C17 C 1.1179(4) 0.6848(8) -0.0738(3) 0.0205(13) Uani 1 1 d . . . . .
C18 C 1.0706(4) 0.7223(8) -0.0347(3) 0.0195(12) Uani 1 1 d . . . . .
H18 H 1.0872 0.6740 0.0093 0.023 Uiso 1 1 calc R . . . .
C19 C 0.9947(4) 0.8322(8) -0.0542(3) 0.0196(12) Uani 1 1 d . . . . .
C20 C 0.9206(4) 1.0764(8) -0.1281(3) 0.0180(12) Uani 1 1 d . . . . .
C21 C 0.8346(4) 1.0421(8) -0.1452(3) 0.0221(13) Uani 1 1 d . . . . .
C22 C 0.7814(4) 1.1852(8) -0.1682(3) 0.0251(14) Uani 1 1 d . . . . .
H22 H 0.7240 1.1680 -0.1796 0.030 Uiso 1 1 calc R . . . .
C23 C 0.8102(4) 1.3515(9) -0.1747(3) 0.0291(15) Uani 1 1 d . . . . .
H23 H 0.7730 1.4447 -0.1875 0.035 Uiso 1 1 calc R . . . .
C24 C 1.0661(3) 1.0393(8) -0.1096(3) 0.0192(13) Uani 1 1 d . . . . .
H24 H 1.1114 1.0326 -0.0652 0.023 Uiso 1 1 calc R . . . .
C25 C 1.0901(4) 0.9383(8) -0.1631(3) 0.0218(13) Uani 1 1 d . . . . .
H25A H 1.0473 0.9549 -0.2077 0.026 Uiso 1 1 calc R . . . .
H25B H 1.1421 0.9850 -0.1660 0.026 Uiso 1 1 calc R . . . .
C26 C 1.1007(4) 0.7461(8) -0.1479(3) 0.0234(13) Uani 1 1 d . . . . .
C27 C 1.0425(4) 1.2321(8) -0.1278(3) 0.0239(13) Uani 1 1 d . . . . .
H27A H 1.0724 1.3082 -0.0899 0.029 Uiso 1 1 calc R . . . .
H27B H 1.0553 1.2666 -0.1687 0.029 Uiso 1 1 calc R . . . .
C28 C 0.9501(4) 1.2396(8) -0.1406(3) 0.0218(13) Uani 1 1 d . . . . .
C29 C 0.8949(4) 1.3780(8) -0.1619(3) 0.0254(14) Uani 1 1 d . . . . .
H29 H 0.9146 1.4884 -0.1677 0.030 Uiso 1 1 calc R . . . .
C30 C 0.7988(4) 0.8615(8) -0.1451(3) 0.0253(14) Uani 1 1 d . . . . .
H30A H 0.8004 0.8324 -0.0992 0.038 Uiso 1 1 calc GR . . . .
H30B H 0.8313 0.7782 -0.1603 0.038 Uiso 1 1 calc GR . . . .
H30C H 0.7419 0.8591 -0.1756 0.038 Uiso 1 1 calc GR . . . .


_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 1.441(7) . ?
O1 C2 1.359(7) . ?
O2 C3 1.215(7) . ?
O3 C14 1.218(7) . ?
O4 C16 1.429(7) . ?
O4 C17 1.360(7) . ?
O5 C19 1.228(7) . ?
O6 C26 1.204(7) . ?
N1 C5 1.498(7) . ?
N1 C10 1.409(8) . ?
N1 C14 1.382(7) . ?
N2 C19 1.368(7) . ?
N2 C20 1.417(7) . ?
N2 C24 1.504(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.522(8) . ?
C2 C15 1.333(8) . ?
C3 C4 1.506(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.498(8) . ?
C5 H5 0.9800 . ?
C5 C6 1.545(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.503(8) . ?
C7 C8 1.388(9) . ?
C7 C10 1.399(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.398(9) . ?
C9 H9 0.9300 . ?
C9 C11 1.367(10) . ?
C10 C12 1.395(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.411(9) . ?
C12 C13 1.501(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.482(8) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.340(8) . ?
C17 C26 1.525(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.475(8) . ?
C20 C21 1.403(8) . ?
C20 C28 1.400(8) . ?
C21 C22 1.398(9) . ?
C21 C30 1.509(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(10) . ?
C23 H23 0.9300 . ?
C23 C29 1.384(9) . ?
C24 H24 0.9800 . ?
C24 C25 1.504(8) . ?
C24 C27 1.541(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.502(9) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.500(8) . ?
C28 C29 1.384(9) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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 O1 C1 116.7(5) . . ?
C17 O4 C16 117.1(5) . . ?
C10 N1 C5 109.6(4) . . ?
C14 N1 C5 119.4(5) . . ?
C14 N1 C10 125.9(5) . . ?
C19 N2 C20 125.1(5) . . ?
C19 N2 C24 119.7(5) . . ?
C20 N2 C24 109.2(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 108.5(5) . . ?
C15 C2 O1 125.4(5) . . ?
C15 C2 C3 126.0(5) . . ?
O2 C3 C2 118.3(5) . . ?
O2 C3 C4 122.4(5) . . ?
C4 C3 C2 119.2(5) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.4(5) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
N1 C5 C4 108.3(5) . . ?
N1 C5 H5 109.8 . . ?
N1 C5 C6 104.5(4) . . ?
C4 C5 H5 109.8 . . ?
C4 C5 C6 114.5(5) . . ?
C6 C5 H5 109.8 . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
C7 C6 C5 104.2(5) . . ?
C7 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
C8 C7 C6 128.9(6) . . ?
C8 C7 C10 120.9(6) . . ?
C10 C7 C6 110.2(5) . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.5(6) . . ?
C9 C8 H8 121.2 . . ?
C8 C9 H9 119.4 . . ?
C11 C9 C8 121.2(6) . . ?
C11 C9 H9 119.4 . . ?
C7 C10 N1 110.1(5) . . ?
C12 C10 N1 127.8(5) . . ?
C12 C10 C7 121.6(6) . . ?
C9 C11 H11 118.8 . . ?
C9 C11 C12 122.4(6) . . ?
C12 C11 H11 118.8 . . ?
C10 C12 C11 115.8(6) . . ?
C10 C12 C13 123.9(6) . . ?
C11 C12 C13 120.0(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 N1 122.1(5) . . ?
O3 C14 C15 121.0(5) . . ?
N1 C14 C15 116.9(5) . . ?
C2 C15 C14 126.2(5) . . ?
C2 C15 H15 116.9 . . ?
C14 C15 H15 116.9 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C26 108.6(5) . . ?
C18 C17 O4 126.0(5) . . ?
C18 C17 C26 125.2(5) . . ?
C17 C18 H18 116.6 . . ?
C17 C18 C19 126.8(5) . . ?
C19 C18 H18 116.6 . . ?
O5 C19 N2 123.1(5) . . ?
O5 C19 C18 120.0(5) . . ?
N2 C19 C18 116.9(5) . . ?
C21 C20 N2 128.1(5) . . ?
C28 C20 N2 110.1(5) . . ?
C28 C20 C21 121.6(6) . . ?
C20 C21 C30 123.7(5) . . ?
C22 C21 C20 115.9(6) . . ?
C22 C21 C30 120.2(5) . . ?
C21 C22 H22 118.5 . . ?
C23 C22 C21 122.9(6) . . ?
C23 C22 H22 118.5 . . ?
C22 C23 H23 120.3 . . ?
C29 C23 C22 119.5(6) . . ?
C29 C23 H23 120.3 . . ?
N2 C24 H24 109.6 . . ?
N2 C24 C27 104.7(5) . . ?
C25 C24 N2 107.9(5) . . ?
C25 C24 H24 109.6 . . ?
C25 C24 C27 115.2(5) . . ?
C27 C24 H24 109.6 . . ?
C24 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 113.2(5) . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
O6 C26 C17 119.0(6) . . ?
O6 C26 C25 122.4(6) . . ?
C25 C26 C17 118.6(5) . . ?
C24 C27 H27A 110.8 . . ?
C24 C27 H27B 110.8 . . ?
H27A C27 H27B 108.9 . . ?
C28 C27 C24 104.5(5) . . ?
C28 C27 H27A 110.8 . . ?
C28 C27 H27B 110.8 . . ?
C20 C28 C27 110.4(5) . . ?
C29 C28 C20 119.8(6) . . ?
C29 C28 C27 129.9(6) . . ?
C23 C29 H29 120.1 . . ?
C28 C29 C23 119.8(6) . . ?
C28 C29 H29 120.1 . . ?
C21 C30 H30A 109.5 . . ?
C21 C30 H30B 109.5 . . ?
C21 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
O1 C2 C3 O2 47.8(7) . . . . ?
O1 C2 C3 C4 -130.8(5) . . . . ?
O1 C2 C15 C14 -176.2(5) . . . . ?
O2 C3 C4 C5 162.3(5) . . . . ?
O3 C14 C15 C2 151.8(6) . . . . ?
O4 C17 C18 C19 -175.7(5) . . . . ?
O4 C17 C26 O6 48.6(7) . . . . ?
O4 C17 C26 C25 -130.5(5) . . . . ?
N1 C5 C6 C7 -9.1(6) . . . . ?
N1 C10 C12 C11 -179.8(5) . . . . ?
N1 C10 C12 C13 -6.5(10) . . . . ?
N1 C14 C15 C2 -28.0(9) . . . . ?
N2 C20 C21 C22 179.4(5) . . . . ?
N2 C20 C21 C30 -5.5(9) . . . . ?
N2 C20 C28 C27 3.6(7) . . . . ?
N2 C20 C28 C29 -176.6(5) . . . . ?
N2 C24 C25 C26 -55.3(6) . . . . ?
N2 C24 C27 C28 -8.2(6) . . . . ?
C1 O1 C2 C3 -176.8(5) . . . . ?
C1 O1 C2 C15 -0.5(8) . . . . ?
C2 C3 C4 C5 -19.2(7) . . . . ?
C3 C2 C15 C14 -0.6(10) . . . . ?
C3 C4 C5 N1 -57.9(6) . . . . ?
C3 C4 C5 C6 -174.1(5) . . . . ?
C4 C5 C6 C7 109.2(5) . . . . ?
C5 N1 C10 C7 -9.9(6) . . . . ?
C5 N1 C10 C12 162.2(6) . . . . ?
C5 N1 C14 O3 153.0(5) . . . . ?
C5 N1 C14 C15 -27.1(7) . . . . ?
C5 C6 C7 C8 -173.7(6) . . . . ?
C5 C6 C7 C10 3.7(6) . . . . ?
C6 C7 C8 C9 174.8(6) . . . . ?
C6 C7 C10 N1 3.7(7) . . . . ?
C6 C7 C10 C12 -169.0(5) . . . . ?
C7 C8 C9 C11 -3.3(9) . . . . ?
C7 C10 C12 C11 -8.5(8) . . . . ?
C7 C10 C12 C13 164.8(6) . . . . ?
C8 C7 C10 N1 -178.6(5) . . . . ?
C8 C7 C10 C12 8.7(9) . . . . ?
C8 C9 C11 C12 3.1(10) . . . . ?
C9 C11 C12 C10 2.8(9) . . . . ?
C9 C11 C12 C13 -170.9(6) . . . . ?
C10 N1 C5 C4 -110.7(5) . . . . ?
C10 N1 C5 C6 11.8(6) . . . . ?
C10 N1 C14 O3 0.9(9) . . . . ?
C10 N1 C14 C15 -179.3(5) . . . . ?
C10 C7 C8 C9 -2.5(9) . . . . ?
C14 N1 C5 C4 93.0(6) . . . . ?
C14 N1 C5 C6 -144.6(5) . . . . ?
C14 N1 C10 C7 144.5(5) . . . . ?
C14 N1 C10 C12 -43.4(9) . . . . ?
C15 C2 C3 O2 -128.4(7) . . . . ?
C15 C2 C3 C4 52.9(8) . . . . ?
C16 O4 C17 C18 -3.5(9) . . . . ?
C16 O4 C17 C26 -178.3(5) . . . . ?
C17 C18 C19 O5 152.9(6) . . . . ?
C17 C18 C19 N2 -26.2(9) . . . . ?
C18 C17 C26 O6 -126.3(7) . . . . ?
C18 C17 C26 C25 54.6(8) . . . . ?
C19 N2 C20 C21 -42.2(9) . . . . ?
C19 N2 C20 C28 143.3(5) . . . . ?
C19 N2 C24 C25 93.3(6) . . . . ?
C19 N2 C24 C27 -143.5(5) . . . . ?
C20 N2 C19 O5 1.5(9) . . . . ?
C20 N2 C19 C18 -179.5(5) . . . . ?
C20 N2 C24 C25 -112.5(5) . . . . ?
C20 N2 C24 C27 10.7(6) . . . . ?
C20 C21 C22 C23 0.6(9) . . . . ?
C20 C28 C29 C23 -3.8(9) . . . . ?
C21 C20 C28 C27 -171.3(5) . . . . ?
C21 C20 C28 C29 8.5(9) . . . . ?
C21 C22 C23 C29 3.8(10) . . . . ?
C22 C23 C29 C28 -2.2(9) . . . . ?
C24 N2 C19 O5 151.3(5) . . . . ?
C24 N2 C19 C18 -29.7(7) . . . . ?
C24 N2 C20 C21 165.3(6) . . . . ?
C24 N2 C20 C28 -9.2(6) . . . . ?
C24 C25 C26 O6 159.3(6) . . . . ?
C24 C25 C26 C17 -21.7(8) . . . . ?
C24 C27 C28 C20 3.2(6) . . . . ?
C24 C27 C28 C29 -176.6(6) . . . . ?
C25 C24 C27 C28 110.2(6) . . . . ?
C26 C17 C18 C19 -1.7(10) . . . . ?
C27 C24 C25 C26 -171.9(5) . . . . ?
C27 C28 C29 C23 175.9(6) . . . . ?
C28 C20 C21 C22 -6.7(8) . . . . ?
C28 C20 C21 C30 168.4(6) . . . . ?
C30 C21 C22 C23 -174.8(6) . . . . ?

_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_2g
_database_code_depnum_ccdc_archive 'CCDC 1470111'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_audit_creation_date             2015-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H12 F3 N O2'
_chemical_formula_sum            'C15 H12 F3 N O2'
_chemical_formula_weight         295.26
_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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6309(3)
_cell_length_b                   7.8723(2)
_cell_length_c                   17.2740(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.9200(12)
_cell_angle_gamma                90
_cell_volume                     1300.13(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6885
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.639
_cell_measurement_theta_min      4.625
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0738 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.8943.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15086
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.634
_diffrn_reflns_theta_min         4.625
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2001
_reflns_number_total             2304
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.068
_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)+(0.0570P)²+0.6450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1169
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C12(H12), C19(H19)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
O O 0.98149(12) 0.15619(15) 0.55989(7) 0.0165(3) Uani 1 1 d . . . . .
F1 F 1.58357(12) 0.14784(19) 0.55746(7) 0.0434(4) Uani 1 1 d . . . . .
N2 N 1.10216(13) -0.07941(17) 0.60869(7) 0.0129(3) Uani 1 1 d . . . . .
F3 F 1.43347(12) 0.31486(17) 0.49516(7) 0.0403(4) Uani 1 1 d . . . . .
F4 F 1.50390(14) 0.36260(17) 0.61566(8) 0.0459(4) Uani 1 1 d . . . . .
O5 O 1.48154(13) 0.05599(18) 0.70732(7) 0.0265(3) Uani 1 1 d . . . . .
C6 C 1.22231(18) 0.1537(2) 0.55287(10) 0.0169(4) Uani 1 1 d . . . . .
H6 H 1.2127 0.2282 0.5108 0.020 Uiso 1 1 calc R . . . .
C7 C 0.98715(16) -0.1744(2) 0.63163(9) 0.0132(4) Uani 1 1 d . . . . .
C8 C 0.77790(18) -0.2398(2) 0.68453(10) 0.0200(4) Uani 1 1 d . . . . .
H8 H 0.7002 -0.2066 0.7080 0.024 Uiso 1 1 calc R . . . .
C9 C 0.87447(17) -0.1154(2) 0.66798(9) 0.0151(4) Uani 1 1 d . . . . .
C10 C 0.85527(18) 0.0647(2) 0.69321(10) 0.0184(4) Uani 1 1 d . . . . .
H10A H 0.9448 0.1133 0.7112 0.028 Uiso 1 1 calc GR . . . .
H10B H 0.7973 0.0664 0.7347 0.028 Uiso 1 1 calc GR . . . .
H10C H 0.8115 0.1295 0.6499 0.028 Uiso 1 1 calc GR . . . .
C11 C 1.21536(17) -0.1968(2) 0.59027(9) 0.0152(4) Uani 1 1 d . . . . .
H11 H 1.2399 -0.1702 0.5382 0.018 Uiso 1 1 calc R . . . .
C12 C 0.91093(19) -0.4659(2) 0.63486(10) 0.0197(4) Uani 1 1 d . . . . .
H12 H 0.9234 -0.5805 0.6246 0.024 Uiso 1 1 calc R . . . .
C13 C 1.09086(17) 0.0758(2) 0.57366(9) 0.0131(3) Uani 1 1 d . . . . .
C14 C 1.35262(18) 0.1293(2) 0.58760(10) 0.0179(4) Uani 1 1 d . . . . .
C15 C 1.39781(17) 0.0078(2) 0.65384(10) 0.0184(4) Uani 1 1 d . . . . .
C16 C 1.00857(17) -0.3466(2) 0.61825(9) 0.0155(4) Uani 1 1 d . . . . .
C17 C 1.34317(17) -0.1720(2) 0.64955(10) 0.0185(4) Uani 1 1 d . . . . .
H17A H 1.3199 -0.2048 0.7006 0.022 Uiso 1 1 calc R . . . .
H17B H 1.4168 -0.2471 0.6365 0.022 Uiso 1 1 calc R . . . .
C18 C 1.14804(18) -0.3746(2) 0.58885(10) 0.0174(4) Uani 1 1 d . . . . .
H18A H 1.1357 -0.4203 0.5363 0.021 Uiso 1 1 calc R . . . .
H18B H 1.2054 -0.4523 0.6225 0.021 Uiso 1 1 calc R . . . .
C19 C 0.79379(19) -0.4103(2) 0.66726(10) 0.0218(4) Uani 1 1 d . . . . .
H19 H 0.7255 -0.4880 0.6775 0.026 Uiso 1 1 calc R . . . .
C1A C 1.46811(19) 0.2388(3) 0.56419(11) 0.0283(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
O C13 1.227(2) . ?
F1 C1A 1.339(2) . ?
N2 C7 1.431(2) . ?
N2 C11 1.492(2) . ?
N2 C13 1.362(2) . ?
F3 C1A 1.340(2) . ?
F4 C1A 1.336(2) . ?
O5 C15 1.212(2) . ?
C6 C13 1.489(2) . ?
C6 C14 1.338(2) . ?
C7 C9 1.397(2) . ?
C7 C16 1.395(2) . ?
C8 C9 1.403(2) . ?
C8 C19 1.388(3) . ?
C9 C10 1.501(2) . ?
C11 C17 1.516(2) . ?
C11 C18 1.542(2) . ?
C12 C16 1.383(2) . ?
C12 C19 1.389(3) . ?
C14 C15 1.514(2) . ?
C14 C1A 1.501(2) . ?
C15 C17 1.509(3) . ?
C16 C18 1.508(2) . ?

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
C7 N2 C11 110.20(13) . . ?
C13 N2 C7 124.65(13) . . ?
C13 N2 C11 118.81(13) . . ?
C14 C6 C13 127.68(16) . . ?
C9 C7 N2 128.28(15) . . ?
C16 C7 N2 109.09(14) . . ?
C16 C7 C9 122.42(15) . . ?
C19 C8 C9 122.57(16) . . ?
C7 C9 C8 115.41(16) . . ?
C7 C9 C10 125.03(15) . . ?
C8 C9 C10 119.48(15) . . ?
N2 C11 C17 109.33(13) . . ?
N2 C11 C18 104.40(12) . . ?
C17 C11 C18 115.66(14) . . ?
C16 C12 C19 118.39(17) . . ?
O C13 N2 124.72(15) . . ?
O C13 C6 118.38(15) . . ?
N2 C13 C6 116.88(14) . . ?
C6 C14 C15 126.74(16) . . ?
C6 C14 C1A 118.83(16) . . ?
C1A C14 C15 114.29(15) . . ?
O5 C15 C14 118.87(17) . . ?
O5 C15 C17 121.81(16) . . ?
C17 C15 C14 119.25(14) . . ?
C7 C16 C18 110.67(14) . . ?
C12 C16 C7 120.50(16) . . ?
C12 C16 C18 128.77(16) . . ?
C15 C17 C11 113.80(14) . . ?
C16 C18 C11 104.61(13) . . ?
C8 C19 C12 120.47(16) . . ?
F1 C1A F3 106.37(15) . . ?
F1 C1A C14 111.49(18) . . ?
F3 C1A C14 112.53(15) . . ?
F4 C1A F1 107.30(16) . . ?
F4 C1A F3 106.43(17) . . ?
F4 C1A C14 112.33(16) . . ?

_olex2_date_sample_submission    2015-03-11
_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_3g
_database_code_depnum_ccdc_archive 'CCDC 1470112'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_audit_creation_date             2015-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H12 F3 N O2'
_chemical_formula_sum            'C15 H12 F3 N O2'
_chemical_formula_weight         295.26
_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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7121(3)
_cell_length_b                   11.7093(3)
_cell_length_c                   14.2353(4)
_cell_angle_alpha                76.9998(11)
_cell_angle_beta                 72.3793(11)
_cell_angle_gamma                69.8941(6)
_cell_volume                     1287.79(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9755
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.594
_cell_measurement_theta_min      3.288
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1002 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.8984.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.075
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_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            16410
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.556
_diffrn_reflns_theta_min         3.287
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4025
_reflns_number_total             4407
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.7803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0893
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C1J(H1J)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C1O(H1OA,H1OB), C1V(H1VA,H1VB)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C15(H15), C1A(H1A), C1L(H1L), C1N(H1N), C1P(H1P), C1R(H1R)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C1T(H1TA,H1TB,H1TC)
;
_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
F F 0.41663(11) 0.41365(8) 0.48235(7) 0.0202(2) Uani 1 1 d . . . . .
F1 F 0.26653(11) 0.45442(9) 0.37662(7) 0.0225(2) Uani 1 1 d . . . . .
F2 F 0.29878(12) 0.60144(8) 0.43015(7) 0.0224(2) Uani 1 1 d . . . . .
O3 O 0.35634(14) 0.64941(10) 0.22626(8) 0.0197(2) Uani 1 1 d . . . . .
O4 O 0.96398(16) 0.42365(14) 0.30144(9) 0.0336(3) Uani 1 1 d . . . . .
N5 N 0.61359(16) 0.54429(11) 0.13749(9) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.60729(19) 0.61350(14) 0.04186(12) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.5511(2) 0.78396(15) -0.08172(13) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.5063 0.8676 -0.1004 0.025 Uiso 1 1 calc R . . . .
C8 C 0.49104(19) 0.56857(13) 0.22209(12) 0.0157(3) Uani 1 1 d . . . . .
C9 C 0.3789(2) 0.49019(14) 0.40101(12) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.73569(19) 0.41933(13) 0.12545(11) 0.0156(3) Uani 1 1 d . . . . .
H10 H 0.6844 0.3573 0.1685 0.019 Uiso 1 1 calc R . . . .
C11 C 0.5490(2) 0.74079(14) 0.01867(12) 0.0181(3) Uani 1 1 d . . . . .
C12 C 0.8561(2) 0.42370(14) 0.26396(12) 0.0195(3) Uani 1 1 d . . . . .
C13 C 0.6176(2) 0.70636(16) -0.15428(12) 0.0220(4) Uani 1 1 d . . . . .
H13 H 0.6135 0.7382 -0.2198 0.026 Uiso 1 1 calc R . . . .
C14 C 0.5024(2) 0.82770(14) 0.09285(13) 0.0225(4) Uani 1 1 d . . . . .
H14A H 0.3923 0.8303 0.1351 0.034 Uiso 1 1 calc GR . . . .
H14B H 0.5019 0.9083 0.0583 0.034 Uiso 1 1 calc GR . . . .
H14C H 0.5832 0.8000 0.1325 0.034 Uiso 1 1 calc GR . . . .
C15 C 0.6850(2) 0.43038(14) 0.33239(12) 0.0176(3) Uani 1 1 d . . . . .
H15 H 0.6852 0.3865 0.3956 0.021 Uiso 1 1 calc R . . . .
C16 C 0.89204(19) 0.41175(14) 0.15548(12) 0.0180(3) Uani 1 1 d . . . . .
H16A H 0.9762 0.3337 0.1422 0.022 Uiso 1 1 calc R . . . .
H16B H 0.9384 0.4765 0.1152 0.022 Uiso 1 1 calc R . . . .
C17 C 0.5324(2) 0.49000(13) 0.31602(11) 0.0160(3) Uani 1 1 d . . . . .
C18 C 0.68515(19) 0.53565(14) -0.03073(12) 0.0167(3) Uani 1 1 d . . . . .
C19 C 0.76199(19) 0.40740(14) 0.01540(12) 0.0172(3) Uani 1 1 d . . . . .
H19A H 0.8810 0.3776 -0.0165 0.021 Uiso 1 1 calc R . . . .
H19B H 0.7056 0.3516 0.0099 0.021 Uiso 1 1 calc R . . . .
C1A C 0.6906(2) 0.58104(15) -0.12969(12) 0.0193(3) Uani 1 1 d . . . . .
H1A H 0.7417 0.5294 -0.1786 0.023 Uiso 1 1 calc R . . . .
F1B F 0.16383(12) 0.98597(9) 0.02681(7) 0.0244(2) Uani 1 1 d . . . . .
F1C F -0.04584(12) 1.14299(8) 0.06990(7) 0.0241(2) Uani 1 1 d . . . . .
F1D F 0.17214(12) 1.09217(9) 0.12958(7) 0.0244(2) Uani 1 1 d . . . . .
O1E O -0.14608(14) 1.14138(9) 0.27473(8) 0.0189(2) Uani 1 1 d . . . . .
N1F N -0.12513(16) 0.95305(11) 0.36942(10) 0.0152(3) Uani 1 1 d . . . . .
C1G C -0.21599(19) 0.99442(14) 0.46321(12) 0.0159(3) Uani 1 1 d . . . . .
O1H O -0.1657(2) 0.72209(13) 0.22312(11) 0.0420(4) Uani 1 1 d . . . . .
C1I C -0.14306(19) 0.91583(14) 0.53757(12) 0.0170(3) Uani 1 1 d . . . . .
C1J C -0.00400(19) 0.82746(13) 0.38476(11) 0.0155(3) Uani 1 1 d . . . . .
H1J H 0.1083 0.8266 0.3423 0.019 Uiso 1 1 calc R . . . .
C1K C -0.36518(19) 1.09069(14) 0.48393(12) 0.0167(3) Uani 1 1 d . . . . .
C1L C -0.2064(2) 0.93829(15) 0.63537(12) 0.0194(3) Uani 1 1 d . . . . .
H1L H -0.1581 0.8862 0.6853 0.023 Uiso 1 1 calc R . . . .
C1M C -0.09848(19) 1.02925(14) 0.28231(12) 0.0162(3) Uani 1 1 d . . . . .
C1N C -0.0017(2) 0.85533(15) 0.17874(12) 0.0208(3) Uani 1 1 d . . . . .
H1N H 0.0615 0.8292 0.1178 0.025 Uiso 1 1 calc R . . . .
C1O C -0.0637(2) 0.73503(14) 0.35690(12) 0.0181(3) Uani 1 1 d . . . . .
H1OA H 0.0175 0.6545 0.3635 0.022 Uiso 1 1 calc R . . . .
H1OB H -0.1703 0.7310 0.4028 0.022 Uiso 1 1 calc R . . . .
C1P C -0.4232(2) 1.11390(15) 0.58293(12) 0.0200(3) Uani 1 1 d . . . . .
H1P H -0.5176 1.1805 0.5997 0.024 Uiso 1 1 calc R . . . .
C1Q C 0.0703(2) 1.04643(14) 0.10437(12) 0.0194(3) Uani 1 1 d . . . . .
C1R C -0.3449(2) 1.04121(15) 0.65703(12) 0.0216(3) Uani 1 1 d . . . . .
H1R H -0.3852 1.0614 0.7214 0.026 Uiso 1 1 calc R . . . .
C1S C -0.0857(2) 0.76724(15) 0.25247(13) 0.0231(4) Uani 1 1 d . . . . .
C1T C -0.4665(2) 1.15779(14) 0.40894(12) 0.0190(3) Uani 1 1 d . . . . .
H1TA H -0.4191 1.2201 0.3670 0.028 Uiso 1 1 calc GR . . . .
H1TB H -0.5809 1.1952 0.4428 0.028 Uiso 1 1 calc GR . . . .
H1TC H -0.4645 1.1010 0.3690 0.028 Uiso 1 1 calc GR . . . .
C1U C -0.00754(19) 0.96617(14) 0.19086(12) 0.0175(3) Uani 1 1 d . . . . .
C1V C -0.0006(2) 0.80996(14) 0.49497(12) 0.0179(3) Uani 1 1 d . . . . .
H1VA H -0.0184 0.7322 0.5291 0.021 Uiso 1 1 calc R . . . .
H1VB H 0.1063 0.8124 0.5006 0.021 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
F C9 1.3466(18) . ?
F1 C9 1.3443(18) . ?
F2 C9 1.3412(18) . ?
O3 C8 1.2231(19) . ?
O4 C12 1.213(2) . ?
N5 C6 1.425(2) . ?
N5 C8 1.356(2) . ?
N5 C10 1.4948(19) . ?
C6 C11 1.396(2) . ?
C6 C18 1.390(2) . ?
C7 C11 1.401(2) . ?
C7 C13 1.388(3) . ?
C8 C17 1.508(2) . ?
C9 C17 1.507(2) . ?
C10 C16 1.516(2) . ?
C10 C19 1.545(2) . ?
C11 C14 1.502(2) . ?
C12 C15 1.501(2) . ?
C12 C16 1.509(2) . ?
C13 C1A 1.394(2) . ?
C15 C17 1.336(2) . ?
C18 C19 1.505(2) . ?
C18 C1A 1.382(2) . ?
F1B C1Q 1.3396(19) . ?
F1C C1Q 1.3444(19) . ?
F1D C1Q 1.3450(19) . ?
O1E C1M 1.2233(19) . ?
N1F C1G 1.425(2) . ?
N1F C1J 1.5006(18) . ?
N1F C1M 1.363(2) . ?
C1G C1I 1.392(2) . ?
C1G C1K 1.399(2) . ?
O1H C1S 1.212(2) . ?
C1I C1L 1.383(2) . ?
C1I C1V 1.506(2) . ?
C1J C1O 1.518(2) . ?
C1J C1V 1.544(2) . ?
C1K C1P 1.401(2) . ?
C1K C1T 1.501(2) . ?
C1L C1R 1.395(2) . ?
C1M C1U 1.508(2) . ?
C1N C1S 1.506(2) . ?
C1N C1U 1.329(2) . ?
C1O C1S 1.503(2) . ?
C1P C1R 1.391(2) . ?
C1Q C1U 1.507(2) . ?

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 N5 C10 109.34(12) . . ?
C8 N5 C6 124.73(13) . . ?
C8 N5 C10 122.25(12) . . ?
C11 C6 N5 127.60(14) . . ?
C18 C6 N5 109.62(13) . . ?
C18 C6 C11 122.52(14) . . ?
C13 C7 C11 122.35(15) . . ?
O3 C8 N5 124.73(14) . . ?
O3 C8 C17 119.98(14) . . ?
N5 C8 C17 115.26(13) . . ?
F C9 C17 112.60(13) . . ?
F1 C9 F 106.40(12) . . ?
F1 C9 C17 111.65(13) . . ?
F2 C9 F 106.14(12) . . ?
F2 C9 F1 107.25(12) . . ?
F2 C9 C17 112.39(13) . . ?
N5 C10 C16 108.46(12) . . ?
N5 C10 C19 103.90(12) . . ?
C16 C10 C19 115.72(13) . . ?
C6 C11 C7 115.37(15) . . ?
C6 C11 C14 123.12(14) . . ?
C7 C11 C14 121.25(14) . . ?
O4 C12 C15 116.43(15) . . ?
O4 C12 C16 122.37(15) . . ?
C15 C12 C16 121.14(13) . . ?
C7 C13 C1A 120.49(15) . . ?
C17 C15 C12 129.59(15) . . ?
C12 C16 C10 112.48(13) . . ?
C9 C17 C8 113.28(13) . . ?
C15 C17 C8 127.66(15) . . ?
C15 C17 C9 118.88(14) . . ?
C6 C18 C19 110.25(14) . . ?
C1A C18 C6 120.45(15) . . ?
C1A C18 C19 129.22(15) . . ?
C18 C19 C10 104.43(12) . . ?
C18 C1A C13 118.20(15) . . ?
C1G N1F C1J 109.78(12) . . ?
C1M N1F C1G 124.04(13) . . ?
C1M N1F C1J 121.16(13) . . ?
C1I C1G N1F 109.52(13) . . ?
C1I C1G C1K 122.49(15) . . ?
C1K C1G N1F 127.73(14) . . ?
C1G C1I C1V 110.53(14) . . ?
C1L C1I C1G 120.54(15) . . ?
C1L C1I C1V 128.89(14) . . ?
N1F C1J C1O 109.04(12) . . ?
N1F C1J C1V 103.99(12) . . ?
C1O C1J C1V 115.37(13) . . ?
C1G C1K C1P 115.29(14) . . ?
C1G C1K C1T 123.14(14) . . ?
C1P C1K C1T 121.33(14) . . ?
C1I C1L C1R 118.16(15) . . ?
O1E C1M N1F 124.60(15) . . ?
O1E C1M C1U 120.06(14) . . ?
N1F C1M C1U 115.32(13) . . ?
C1U C1N C1S 127.44(16) . . ?
C1S C1O C1J 112.42(13) . . ?
C1R C1P C1K 122.49(15) . . ?
F1B C1Q F1C 106.31(12) . . ?
F1B C1Q F1D 106.66(13) . . ?
F1B C1Q C1U 112.64(13) . . ?
F1C C1Q F1D 106.69(12) . . ?
F1C C1Q C1U 112.55(13) . . ?
F1D C1Q C1U 111.57(13) . . ?
C1P C1R C1L 120.42(15) . . ?
O1H C1S C1N 117.42(16) . . ?
O1H C1S C1O 122.50(16) . . ?
C1O C1S C1N 120.04(14) . . ?
C1N C1U C1M 126.94(15) . . ?
C1N C1U C1Q 119.62(15) . . ?
C1Q C1U C1M 113.24(13) . . ?
C1I C1V C1J 104.61(12) . . ?

_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_2c
_database_code_depnum_ccdc_archive 'CCDC 1470113'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_audit_creation_date             2014-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C14 H12 Br N O2)'
_chemical_formula_sum            'C27 H24 Br2 N3 O4'
_chemical_formula_weight         614.31
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   18.1984(5)
_cell_length_b                   7.3629(2)
_cell_length_c                   19.2858(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.4870(10)
_cell_angle_gamma                90
_cell_volume                     2450.81(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.502
_cell_measurement_theta_min      2.910
_shelx_estimated_absorpt_T_max   0.773
_shelx_estimated_absorpt_T_min   0.409
_exptl_absorpt_coefficient_mu    4.534
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0904 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.7792.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34112
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.851
_diffrn_reflns_theta_min         2.910
_diffrn_ambient_temperature      99.96
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3735
_reflns_number_total             4323
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.088
_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)+(0.0315P)²+4.2277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C13(H13), C20(H20), C21(H21), C23(H23), C25(H25)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.71816(2) 0.99120(4) 0.01715(2) 0.02204(10) Uani 1 1 d . . . . .
Br2 Br -0.20526(2) 1.48980(4) 0.02883(2) 0.02310(10) Uani 1 1 d . . . . .
O1 O 0.46307(11) 0.7295(3) 0.02336(11) 0.0234(5) Uani 1 1 d . . . . .
O2 O 0.75925(13) 0.8867(3) 0.17640(12) 0.0294(5) Uani 1 1 d . . . . .
O3 O -0.13379(14) 1.3682(3) 0.18748(12) 0.0338(5) Uani 1 1 d . . . . .
O4 O 0.05082(12) 1.2380(3) 0.02359(11) 0.0238(5) Uani 1 1 d . . . . .
N1 N 0.55912(13) 0.5674(3) 0.10525(12) 0.0163(5) Uani 1 1 d . . . . .
C2 C 0.40436(18) 0.6606(4) 0.13883(18) 0.0263(7) Uani 1 1 d . . . . .
H2A H 0.3700 0.6866 0.0893 0.039 Uiso 1 1 calc GR . . . .
H2B H 0.4453 0.7528 0.1532 0.039 Uiso 1 1 calc GR . . . .
H2C H 0.3744 0.6627 0.1731 0.039 Uiso 1 1 calc GR . . . .
N3 N 0.01344(13) 1.0653(3) 0.10534(13) 0.0171(5) Uani 1 1 d . . . . .
C1 C 0.66386(17) 0.8360(4) 0.06309(16) 0.0193(6) Uani 1 1 d . . . . .
C3 C 0.58948(16) 0.8002(4) 0.02752(16) 0.0194(6) Uani 1 1 d . . . . .
H3 H 0.5702 0.8490 -0.0205 0.023 Uiso 1 1 calc R . . . .
C4 C 0.53187(16) 0.6945(4) 0.05214(15) 0.0180(6) Uani 1 1 d . . . . .
C5 C 0.51140(16) 0.4435(4) 0.12918(15) 0.0182(6) Uani 1 1 d . . . . .
C6 C 0.54975(16) 0.2782(4) 0.14737(15) 0.0180(6) Uani 1 1 d . . . . .
C7 C 0.51346(17) 0.1318(4) 0.16795(16) 0.0217(6) Uani 1 1 d . . . . .
H7 H 0.5389 0.0178 0.1794 0.026 Uiso 1 1 calc R . . . .
C8 C 0.43897(18) 0.1558(4) 0.17143(17) 0.0253(7) Uani 1 1 d . . . . .
H8 H 0.4116 0.0554 0.1821 0.030 Uiso 1 1 calc R . . . .
C9 C 0.63054(16) 0.2894(4) 0.14334(16) 0.0208(6) Uani 1 1 d . . . . .
H9A H 0.6386 0.1983 0.1087 0.025 Uiso 1 1 calc R . . . .
H9B H 0.6692 0.2689 0.1920 0.025 Uiso 1 1 calc R . . . .
C10 C 0.63695(16) 0.4834(4) 0.11620(15) 0.0178(6) Uani 1 1 d . . . . .
H10 H 0.6470 0.4774 0.0682 0.021 Uiso 1 1 calc R . . . .
C11 C 0.69863(16) 0.5995(4) 0.16875(15) 0.0179(6) Uani 1 1 d . . . . .
H11A H 0.6844 0.6176 0.2137 0.022 Uiso 1 1 calc R . . . .
H11B H 0.7483 0.5322 0.1826 0.022 Uiso 1 1 calc R . . . .
C12 C 0.71099(16) 0.7829(4) 0.13955(16) 0.0202(6) Uani 1 1 d . . . . .
C13 C 0.40453(17) 0.3259(4) 0.15938(17) 0.0243(6) Uani 1 1 d . . . . .
H13 H 0.3546 0.3401 0.1644 0.029 Uiso 1 1 calc R . . . .
C14 C 0.44010(16) 0.4771(4) 0.14022(15) 0.0191(6) Uani 1 1 d . . . . .
C15 C -0.12021(16) 1.3313(4) 0.07059(15) 0.0186(6) Uani 1 1 d . . . . .
C16 C -0.11292(16) 1.2700(4) 0.14692(16) 0.0221(6) Uani 1 1 d . . . . .
C17 C -0.08179(16) 1.0824(4) 0.17097(15) 0.0198(6) Uani 1 1 d . . . . .
H17A H -0.1225 1.0122 0.1830 0.024 Uiso 1 1 calc R . . . .
H17B H -0.0374 1.0941 0.2165 0.024 Uiso 1 1 calc R . . . .
C18 C -0.05566(16) 0.9749(4) 0.11638(16) 0.0190(6) Uani 1 1 d . . . . .
H18 H -0.0986 0.9707 0.0687 0.023 Uiso 1 1 calc R . . . .
C19 C -0.02889(17) 0.7807(4) 0.14057(17) 0.0225(6) Uani 1 1 d . . . . .
H19A H -0.0353 0.7530 0.1886 0.027 Uiso 1 1 calc R . . . .
H19B H -0.0588 0.6911 0.1042 0.027 Uiso 1 1 calc R . . . .
C1A C 0.05521(17) 0.7774(4) 0.14568(15) 0.0193(6) Uani 1 1 d . . . . .
C20 C 0.10724(17) 0.6355(4) 0.16598(16) 0.0222(6) Uani 1 1 d . . . . .
H20 H 0.0909 0.5192 0.1767 0.027 Uiso 1 1 calc R . . . .
C21 C 0.18393(18) 0.6661(4) 0.17046(17) 0.0254(7) Uani 1 1 d . . . . .
H21 H 0.2200 0.5687 0.1819 0.030 Uiso 1 1 calc R . . . .
C22 C 0.00306(16) 1.1970(4) 0.05338(15) 0.0179(6) Uani 1 1 d . . . . .
C23 C -0.07193(16) 1.3008(4) 0.03219(16) 0.0204(6) Uani 1 1 d . . . . .
H23 H -0.0872 1.3522 -0.0154 0.025 Uiso 1 1 calc R . . . .
C24 C 0.07894(16) 0.9463(4) 0.12812(15) 0.0179(6) Uani 1 1 d . . . . .
C25 C 0.20770(17) 0.8376(4) 0.15827(16) 0.0234(6) Uani 1 1 d . . . . .
H25 H 0.2608 0.8563 0.1635 0.028 Uiso 1 1 calc R . . . .
C26 C 0.15705(17) 0.9851(4) 0.13854(16) 0.0206(6) Uani 1 1 d . . . . .
C27 C 0.18911(17) 1.1724(4) 0.13602(18) 0.0253(7) Uani 1 1 d . . . . .
H27A H 0.1860 1.2017 0.0856 0.038 Uiso 1 1 calc GR . . . .
H27B H 0.2433 1.1764 0.1673 0.038 Uiso 1 1 calc GR . . . .
H27C H 0.1589 1.2610 0.1535 0.038 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.903(3) . ?
Br2 C15 1.901(3) . ?
O1 C4 1.225(3) . ?
O2 C12 1.210(4) . ?
O3 C16 1.211(4) . ?
O4 C22 1.222(3) . ?
N1 C4 1.360(4) . ?
N1 C5 1.433(4) . ?
N1 C10 1.498(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C14 1.496(4) . ?
N3 C18 1.496(3) . ?
N3 C22 1.364(4) . ?
N3 C24 1.432(4) . ?
C1 C3 1.335(4) . ?
C1 C12 1.504(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.499(4) . ?
C5 C6 1.392(4) . ?
C5 C14 1.402(4) . ?
C6 C7 1.386(4) . ?
C6 C9 1.499(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(4) . ?
C8 H8 0.9500 . ?
C8 C13 1.387(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.538(4) . ?
C10 H10 1.0000 . ?
C10 C11 1.515(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.507(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(4) . ?
C15 C16 1.505(4) . ?
C15 C23 1.335(4) . ?
C16 C17 1.509(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.509(4) . ?
C18 H18 1.0000 . ?
C18 C19 1.535(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C1A 1.502(4) . ?
C1A C20 1.381(4) . ?
C1A C24 1.393(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(4) . ?
C21 H21 0.9500 . ?
C21 C25 1.379(4) . ?
C22 C23 1.503(4) . ?
C23 H23 0.9500 . ?
C24 C26 1.401(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.397(4) . ?
C26 C27 1.504(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C4 N1 C5 124.5(2) . . ?
C4 N1 C10 119.6(2) . . ?
C5 N1 C10 109.5(2) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C14 C2 H2A 109.5 . . ?
C14 C2 H2B 109.5 . . ?
C14 C2 H2C 109.5 . . ?
C22 N3 C18 119.6(2) . . ?
C22 N3 C24 124.6(2) . . ?
C24 N3 C18 109.8(2) . . ?
C3 C1 Br1 118.1(2) . . ?
C3 C1 C12 128.5(3) . . ?
C12 C1 Br1 113.2(2) . . ?
C1 C3 H3 115.2 . . ?
C1 C3 C4 129.5(3) . . ?
C4 C3 H3 115.2 . . ?
O1 C4 N1 124.2(3) . . ?
O1 C4 C3 117.7(3) . . ?
N1 C4 C3 118.1(2) . . ?
C6 C5 N1 109.3(2) . . ?
C6 C5 C14 122.0(3) . . ?
C14 C5 N1 128.4(3) . . ?
C5 C6 C9 111.1(2) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 C9 128.4(3) . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.4(3) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 H8 119.9 . . ?
C13 C8 C7 120.2(3) . . ?
C13 C8 H8 119.9 . . ?
C6 C9 H9A 110.9 . . ?
C6 C9 H9B 110.9 . . ?
C6 C9 C10 104.5(2) . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
N1 C10 C9 105.1(2) . . ?
N1 C10 H10 109.3 . . ?
N1 C10 C11 109.2(2) . . ?
C9 C10 H10 109.3 . . ?
C11 C10 C9 114.6(2) . . ?
C11 C10 H10 109.3 . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 C10 115.0(2) . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
O2 C12 C1 119.6(3) . . ?
O2 C12 C11 120.9(3) . . ?
C1 C12 C11 119.5(2) . . ?
C8 C13 H13 118.6 . . ?
C8 C13 C14 122.8(3) . . ?
C14 C13 H13 118.6 . . ?
C5 C14 C2 125.1(3) . . ?
C13 C14 C2 119.3(3) . . ?
C13 C14 C5 115.4(3) . . ?
C16 C15 Br2 113.9(2) . . ?
C23 C15 Br2 117.3(2) . . ?
C23 C15 C16 128.5(3) . . ?
O3 C16 C15 120.3(3) . . ?
O3 C16 C17 120.8(3) . . ?
C15 C16 C17 118.9(2) . . ?
C16 C17 H17A 108.3 . . ?
C16 C17 H17B 108.3 . . ?
C16 C17 C18 115.9(2) . . ?
H17A C17 H17B 107.4 . . ?
C18 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
N3 C18 C17 109.3(2) . . ?
N3 C18 H18 109.3 . . ?
N3 C18 C19 104.9(2) . . ?
C17 C18 H18 109.3 . . ?
C17 C18 C19 114.6(2) . . ?
C19 C18 H18 109.3 . . ?
C18 C19 H19A 110.8 . . ?
C18 C19 H19B 110.8 . . ?
H19A C19 H19B 108.9 . . ?
C1A C19 C18 104.7(2) . . ?
C1A C19 H19A 110.8 . . ?
C1A C19 H19B 110.8 . . ?
C20 C1A C19 128.6(3) . . ?
C20 C1A C24 120.5(3) . . ?
C24 C1A C19 111.0(3) . . ?
C1A C20 H20 120.7 . . ?
C1A C20 C21 118.7(3) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 120.0 . . ?
C25 C21 C20 120.1(3) . . ?
C25 C21 H21 120.0 . . ?
O4 C22 N3 124.6(3) . . ?
O4 C22 C23 117.8(3) . . ?
N3 C22 C23 117.6(2) . . ?
C15 C23 C22 129.4(3) . . ?
C15 C23 H23 115.3 . . ?
C22 C23 H23 115.3 . . ?
C1A C24 N3 109.2(2) . . ?
C1A C24 C26 121.7(3) . . ?
C26 C24 N3 128.9(3) . . ?
C21 C25 H25 118.6 . . ?
C21 C25 C26 122.9(3) . . ?
C26 C25 H25 118.6 . . ?
C24 C26 C27 124.7(3) . . ?
C25 C26 C24 115.6(3) . . ?
C25 C26 C27 119.5(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
Br1 C1 C3 C4 -175.5(2) . . . . ?
Br1 C1 C12 O2 30.7(4) . . . . ?
Br1 C1 C12 C11 -148.1(2) . . . . ?
Br2 C15 C16 O3 -30.9(4) . . . . ?
Br2 C15 C16 C17 147.1(2) . . . . ?
Br2 C15 C23 C22 174.0(2) . . . . ?
O3 C16 C17 C18 -178.4(3) . . . . ?
O4 C22 C23 C15 -154.0(3) . . . . ?
N1 C5 C6 C7 -176.0(2) . . . . ?
N1 C5 C6 C9 5.7(3) . . . . ?
N1 C5 C14 C2 -9.1(5) . . . . ?
N1 C5 C14 C13 176.1(3) . . . . ?
N1 C10 C11 C12 -68.4(3) . . . . ?
N3 C18 C19 C1A 3.1(3) . . . . ?
N3 C22 C23 C15 25.1(5) . . . . ?
N3 C24 C26 C25 -177.4(3) . . . . ?
N3 C24 C26 C27 7.8(5) . . . . ?
C1 C3 C4 O1 155.1(3) . . . . ?
C1 C3 C4 N1 -24.4(5) . . . . ?
C3 C1 C12 O2 -143.6(3) . . . . ?
C3 C1 C12 C11 37.7(4) . . . . ?
C4 N1 C5 C6 145.2(3) . . . . ?
C4 N1 C5 C14 -40.1(4) . . . . ?
C4 N1 C10 C9 -148.7(2) . . . . ?
C4 N1 C10 C11 87.9(3) . . . . ?
C5 N1 C4 O1 7.2(4) . . . . ?
C5 N1 C4 C3 -173.4(2) . . . . ?
C5 N1 C10 C9 4.5(3) . . . . ?
C5 N1 C10 C11 -118.9(2) . . . . ?
C5 C6 C7 C8 -1.4(4) . . . . ?
C5 C6 C9 C10 -2.7(3) . . . . ?
C6 C5 C14 C2 165.0(3) . . . . ?
C6 C5 C14 C13 -9.9(4) . . . . ?
C6 C7 C8 C13 -4.4(4) . . . . ?
C6 C9 C10 N1 -1.1(3) . . . . ?
C6 C9 C10 C11 118.7(3) . . . . ?
C7 C6 C9 C10 179.2(3) . . . . ?
C7 C8 C13 C14 3.0(5) . . . . ?
C8 C13 C14 C2 -171.2(3) . . . . ?
C8 C13 C14 C5 4.0(4) . . . . ?
C9 C6 C7 C8 176.5(3) . . . . ?
C9 C10 C11 C12 174.0(2) . . . . ?
C10 N1 C4 O1 156.2(3) . . . . ?
C10 N1 C4 C3 -24.4(4) . . . . ?
C10 N1 C5 C6 -6.4(3) . . . . ?
C10 N1 C5 C14 168.3(3) . . . . ?
C10 C11 C12 O2 -179.3(3) . . . . ?
C10 C11 C12 C1 -0.6(4) . . . . ?
C12 C1 C3 C4 -1.4(5) . . . . ?
C14 C5 C6 C7 8.9(4) . . . . ?
C14 C5 C6 C9 -169.4(3) . . . . ?
C15 C16 C17 C18 3.6(4) . . . . ?
C16 C15 C23 C22 0.2(5) . . . . ?
C16 C17 C18 N3 66.1(3) . . . . ?
C16 C17 C18 C19 -176.5(2) . . . . ?
C17 C18 C19 C1A -116.8(3) . . . . ?
C18 N3 C22 O4 -155.5(3) . . . . ?
C18 N3 C22 C23 25.5(4) . . . . ?
C18 N3 C24 C1A 6.5(3) . . . . ?
C18 N3 C24 C26 -168.5(3) . . . . ?
C18 C19 C1A C20 179.2(3) . . . . ?
C18 C19 C1A C24 0.6(3) . . . . ?
C19 C1A C20 C21 -176.7(3) . . . . ?
C19 C1A C24 N3 -4.4(3) . . . . ?
C19 C1A C24 C26 171.0(3) . . . . ?
C1A C20 C21 C25 3.2(5) . . . . ?
C1A C24 C26 C25 8.1(4) . . . . ?
C1A C24 C26 C27 -166.6(3) . . . . ?
C20 C1A C24 N3 176.9(3) . . . . ?
C20 C1A C24 C26 -7.7(4) . . . . ?
C20 C21 C25 C26 -2.4(5) . . . . ?
C21 C25 C26 C24 -3.1(4) . . . . ?
C21 C25 C26 C27 171.9(3) . . . . ?
C22 N3 C18 C17 -88.3(3) . . . . ?
C22 N3 C18 C19 148.3(3) . . . . ?
C22 N3 C24 C1A -146.1(3) . . . . ?
C22 N3 C24 C26 38.9(4) . . . . ?
C23 C15 C16 O3 143.1(3) . . . . ?
C23 C15 C16 C17 -38.9(4) . . . . ?
C24 N3 C18 C17 117.5(3) . . . . ?
C24 N3 C18 C19 -5.8(3) . . . . ?
C24 N3 C22 O4 -5.4(4) . . . . ?
C24 N3 C22 C23 175.6(2) . . . . ?
C24 C1A C20 C21 1.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
