# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_yg_98
_database_code_depnum_ccdc_archive 'CCDC 1483553'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;
_audit_creation_date             2016-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        YG-98
_chemical_formula_moiety         'C21 H17 Br N2 O3'
_chemical_formula_sum            'C21 H17 Br N2 O3'
_chemical_formula_weight         425.27
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5895(10)
_cell_length_b                   12.3063(10)
_cell_length_c                   9.7721(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.940(13)
_cell_angle_gamma                90
_cell_volume                     958.16(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    503
_cell_measurement_temperature    295.05(10)
_cell_measurement_theta_max      19.2390
_cell_measurement_theta_min      4.1740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.1273
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4032
_diffrn_reflns_point_group_measured_fraction_full 0.775
_diffrn_reflns_point_group_measured_fraction_max 0.658
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.860
_diffrn_reflns_theta_min         3.986
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   95.00   2.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       21.0541  178.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   44.00   90.00   2.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       21.0541   77.0000 -150.0000 23

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   24.00   2.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.8354  -99.0000 -120.0000 22

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   98.00   2.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       21.0541 -178.0000   90.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0724366000
_diffrn_orient_matrix_UB_12      0.0235609000
_diffrn_orient_matrix_UB_13      0.0061145000
_diffrn_orient_matrix_UB_21      -0.0514152000
_diffrn_orient_matrix_UB_22      -0.0288698000
_diffrn_orient_matrix_UB_23      -0.0636935000
_diffrn_orient_matrix_UB_31      -0.0052361000
_diffrn_orient_matrix_UB_32      -0.0439974000
_diffrn_orient_matrix_UB_33      0.0450186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.429
_reflns_Friedel_fraction_full    0.530
_reflns_Friedel_fraction_max     0.414
_reflns_number_gt                1665
_reflns_number_total             3317
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.010
_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)+(0.0538P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1798
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_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 0.26371(17) -0.39834(18) -1.00134(15) 0.0820(6) Uani 1 1 d . . . . .
O1 O -0.6858(10) -0.0943(8) -1.6420(8) 0.067(3) Uani 1 1 d . . . . .
O2 O -0.8846(10) -0.0093(7) -1.5896(7) 0.053(2) Uani 1 1 d . . . . .
O3 O -1.3675(11) 0.0681(10) -1.6061(10) 0.090(4) Uani 1 1 d . . . . .
N1 N -0.3814(10) -0.1778(8) -1.0323(8) 0.043(2) Uani 1 1 d . . . . .
N2 N -0.4014(12) -0.1607(8) -0.8997(8) 0.049(3) Uani 1 1 d . . . . .
C1 C -0.2337(15) -0.3280(9) -1.1034(10) 0.048(3) Uani 1 1 d . . . . .
H1 H -0.3368 -0.3583 -1.1606 0.057 Uiso 1 1 calc R . . . .
C2 C -0.0918(13) -0.3772(10) -1.0990(10) 0.051(3) Uani 1 1 d . . . . .
H2 H -0.0970 -0.4407 -1.1521 0.061 Uiso 1 1 calc R . . . .
C3 C 0.0601(14) -0.3327(9) -1.0154(11) 0.048(3) Uani 1 1 d . . . . .
C4 C 0.0686(13) -0.2391(9) -0.9356(12) 0.048(3) Uani 1 1 d . . . . .
H4 H 0.1717 -0.2087 -0.8787 0.058 Uiso 1 1 calc R . . . .
C5 C -0.0774(13) -0.1920(9) -0.9418(10) 0.043(3) Uani 1 1 d . . . . .
H5 H -0.0722 -0.1293 -0.8872 0.051 Uiso 1 1 calc R . . . .
C6 C -0.2305(13) -0.2333(9) -1.0251(10) 0.043(3) Uani 1 1 d . . . . .
C7 C -0.5387(15) -0.1035(10) -0.9360(12) 0.054(3) Uani 1 1 d . . . . .
H7 H -0.5829 -0.0779 -0.8685 0.064 Uiso 1 1 calc R . . . .
C8 C -0.6131(14) -0.0848(10) -1.0908(10) 0.040(3) Uani 1 1 d . . . . .
C9 C -0.5069(11) -0.1313(8) -1.1470(9) 0.030(2) Uani 1 1 d . . . . .
C10 C -0.5275(12) -0.1243(8) -1.3014(9) 0.038(2) Uani 1 1 d . . . . .
C11 C -0.6801(12) -0.0886(9) -1.3901(10) 0.036(2) Uani 1 1 d . . . . .
C12 C -0.8220(13) -0.0599(10) -1.3403(10) 0.044(3) Uani 1 1 d . . . . .
C13 C -0.7602(13) -0.0175(10) -1.1818(9) 0.051(3) Uani 1 1 d . . . . .
H13A H -0.7275 0.0581 -1.1790 0.061 Uiso 1 1 calc R . . . .
H13B H -0.8489 -0.0229 -1.1433 0.061 Uiso 1 1 calc R . . . .
C14 C -0.3843(13) -0.1422(11) -1.3505(11) 0.051(3) Uani 1 1 d . . . . .
H14A H -0.2825 -0.1160 -1.2762 0.076 Uiso 1 1 calc GR . . . .
H14B H -0.4049 -0.1037 -1.4410 0.076 Uiso 1 1 calc GR . . . .
H14C H -0.3736 -0.2184 -1.3659 0.076 Uiso 1 1 calc GR . . . .
C15 C -0.7419(15) -0.0656(11) -1.5496(11) 0.052(3) Uani 1 1 d . . . . .
C16 C -0.9094(13) 0.0298(9) -1.4552(10) 0.045(3) Uani 1 1 d . . . . .
H16 H -0.8471 0.0978 -1.4231 0.054 Uiso 1 1 calc R . . . .
C17 C -1.0902(14) 0.0521(9) -1.4924(11) 0.046(3) Uani 1 1 d . . . . .
C18 C -1.2261(16) 0.0274(12) -1.6102(12) 0.068(4) Uani 1 1 d . . . . .
H18 H -1.2223 -0.0144 -1.6882 0.081 Uiso 1 1 calc R . . . .
C19 C -1.3175(17) 0.1227(15) -1.4770(17) 0.084(5) Uani 1 1 d . . . . .
H19 H -1.3909 0.1590 -1.4428 0.100 Uiso 1 1 calc R . . . .
C20 C -1.1537(16) 0.1192(13) -1.4044(12) 0.063(4) Uani 1 1 d . . . . .
H20 H -1.0923 0.1529 -1.3153 0.076 Uiso 1 1 calc R . . . .
C21 C -0.9362(14) -0.1588(10) -1.3596(12) 0.054(3) Uani 1 1 d . . . . .
H21A H -1.0250 -0.1413 -1.3262 0.082 Uiso 1 1 calc GR . . . .
H21B H -0.8719 -0.2184 -1.3029 0.082 Uiso 1 1 calc GR . . . .
H21C H -0.9832 -0.1788 -1.4620 0.082 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 C3 1.884(11) . ?
O1 C15 1.223(13) . ?
O2 C15 1.333(13) . ?
O2 C16 1.487(12) . ?
O3 C18 1.328(14) . ?
O3 C19 1.350(17) . ?
N1 N2 1.385(11) . ?
N1 C6 1.443(13) . ?
N1 C9 1.358(12) . ?
N2 C7 1.304(14) . ?
C1 H1 0.9300 . ?
C1 C2 1.347(14) . ?
C1 C6 1.389(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(14) . ?
C3 C4 1.378(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.360(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.424(14) . ?
C8 C9 1.355(13) . ?
C8 C13 1.494(15) . ?
C9 C10 1.454(11) . ?
C10 C11 1.346(12) . ?
C10 C14 1.494(13) . ?
C11 C12 1.514(14) . ?
C11 C15 1.475(13) . ?
C12 C13 1.530(13) . ?
C12 C16 1.553(15) . ?
C12 C21 1.530(15) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.483(14) . ?
C17 C18 1.332(15) . ?
C17 C20 1.439(15) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.319(16) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C15 O2 C16 109.2(8) . . ?
C18 O3 C19 104.0(10) . . ?
N2 N1 C6 116.7(8) . . ?
C9 N1 N2 111.8(9) . . ?
C9 N1 C6 131.4(8) . . ?
C7 N2 N1 104.1(8) . . ?
C2 C1 H1 119.1 . . ?
C2 C1 C6 121.8(10) . . ?
C6 C1 H1 119.1 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.3(10) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 Br1 121.6(9) . . ?
C2 C3 C4 120.6(10) . . ?
C4 C3 Br1 117.8(9) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.5(10) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.4(10) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 N1 122.5(9) . . ?
C5 C6 N1 120.2(10) . . ?
C5 C6 C1 117.3(11) . . ?
N2 C7 H7 123.9 . . ?
N2 C7 C8 112.2(10) . . ?
C8 C7 H7 123.9 . . ?
C7 C8 C13 131.8(10) . . ?
C9 C8 C7 105.0(10) . . ?
C9 C8 C13 122.7(8) . . ?
N1 C9 C10 129.3(9) . . ?
C8 C9 N1 106.9(8) . . ?
C8 C9 C10 123.8(9) . . ?
C9 C10 C14 121.9(8) . . ?
C11 C10 C9 113.5(8) . . ?
C11 C10 C14 124.1(8) . . ?
C10 C11 C12 125.2(8) . . ?
C10 C11 C15 128.5(9) . . ?
C15 C11 C12 106.2(9) . . ?
C11 C12 C13 112.8(9) . . ?
C11 C12 C16 99.4(8) . . ?
C11 C12 C21 109.3(9) . . ?
C13 C12 C16 112.4(10) . . ?
C21 C12 C13 111.1(9) . . ?
C21 C12 C16 111.2(9) . . ?
C8 C13 C12 108.1(9) . . ?
C8 C13 H13A 110.1 . . ?
C8 C13 H13B 110.1 . . ?
C12 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
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 . . ?
O1 C15 O2 120.4(10) . . ?
O1 C15 C11 129.7(12) . . ?
O2 C15 C11 109.7(10) . . ?
O2 C16 C12 102.6(8) . . ?
O2 C16 H16 108.5 . . ?
C12 C16 H16 108.5 . . ?
C17 C16 O2 109.0(8) . . ?
C17 C16 C12 119.2(9) . . ?
C17 C16 H16 108.5 . . ?
C18 C17 C16 132.0(11) . . ?
C18 C17 C20 104.0(10) . . ?
C20 C17 C16 123.7(10) . . ?
O3 C18 C17 113.8(11) . . ?
O3 C18 H18 123.1 . . ?
C17 C18 H18 123.1 . . ?
O3 C19 H19 123.6 . . ?
C20 C19 O3 112.9(13) . . ?
C20 C19 H19 123.6 . . ?
C17 C20 H20 127.4 . . ?
C19 C20 C17 105.3(12) . . ?
C19 C20 H20 127.4 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 C3 C4 C5 -178.5(8) . . . . ?
O2 C16 C17 C18 12.3(18) . . . . ?
O2 C16 C17 C20 -161.2(10) . . . . ?
O3 C19 C20 C17 -2.2(18) . . . . ?
N1 N2 C7 C8 1.7(13) . . . . ?
N1 C9 C10 C11 169.5(10) . . . . ?
N1 C9 C10 C14 -17.6(17) . . . . ?
N2 N1 C6 C1 123.7(11) . . . . ?
N2 N1 C6 C5 -57.8(13) . . . . ?
N2 N1 C9 C8 -1.2(12) . . . . ?
N2 N1 C9 C10 175.7(9) . . . . ?
N2 C7 C8 C9 -2.4(14) . . . . ?
N2 C7 C8 C13 -174.3(12) . . . . ?
C1 C2 C3 Br1 178.9(8) . . . . ?
C1 C2 C3 C4 0.5(16) . . . . ?
C2 C1 C6 N1 178.1(10) . . . . ?
C2 C1 C6 C5 -0.5(15) . . . . ?
C2 C3 C4 C5 0.0(15) . . . . ?
C3 C4 C5 C6 -0.8(16) . . . . ?
C4 C5 C6 N1 -177.6(10) . . . . ?
C4 C5 C6 C1 1.0(15) . . . . ?
C6 N1 N2 C7 175.6(9) . . . . ?
C6 N1 C9 C8 -176.4(10) . . . . ?
C6 N1 C9 C10 0.6(18) . . . . ?
C6 C1 C2 C3 -0.2(16) . . . . ?
C7 C8 C9 N1 2.1(12) . . . . ?
C7 C8 C9 C10 -175.1(9) . . . . ?
C7 C8 C13 C12 -159.1(13) . . . . ?
C8 C9 C10 C11 -14.0(14) . . . . ?
C8 C9 C10 C14 158.9(11) . . . . ?
C9 N1 N2 C7 -0.3(12) . . . . ?
C9 N1 C6 C1 -61.4(16) . . . . ?
C9 N1 C6 C5 117.2(12) . . . . ?
C9 C8 C13 C12 30.3(15) . . . . ?
C9 C10 C11 C12 -1.3(15) . . . . ?
C9 C10 C11 C15 176.2(11) . . . . ?
C10 C11 C12 C13 30.2(16) . . . . ?
C10 C11 C12 C16 149.4(10) . . . . ?
C10 C11 C12 C21 -94.0(12) . . . . ?
C10 C11 C15 O1 17(2) . . . . ?
C10 C11 C15 O2 -166.1(10) . . . . ?
C11 C12 C13 C8 -40.9(13) . . . . ?
C11 C12 C16 O2 34.5(10) . . . . ?
C11 C12 C16 C17 155.0(10) . . . . ?
C12 C11 C15 O1 -164.7(13) . . . . ?
C12 C11 C15 O2 11.8(13) . . . . ?
C12 C16 C17 C18 -104.9(14) . . . . ?
C12 C16 C17 C20 81.6(15) . . . . ?
C13 C8 C9 N1 174.9(10) . . . . ?
C13 C8 C9 C10 -2.3(17) . . . . ?
C13 C12 C16 O2 154.1(8) . . . . ?
C13 C12 C16 C17 -85.4(12) . . . . ?
C14 C10 C11 C12 -174.0(12) . . . . ?
C14 C10 C11 C15 3.5(18) . . . . ?
C15 O2 C16 C12 -30.2(11) . . . . ?
C15 O2 C16 C17 -157.5(9) . . . . ?
C15 C11 C12 C13 -147.8(10) . . . . ?
C15 C11 C12 C16 -28.5(11) . . . . ?
C15 C11 C12 C21 88.0(11) . . . . ?
C16 O2 C15 O1 -171.1(11) . . . . ?
C16 O2 C15 C11 12.0(12) . . . . ?
C16 C12 C13 C8 -152.3(10) . . . . ?
C16 C17 C18 O3 -176.1(12) . . . . ?
C16 C17 C20 C19 177.3(12) . . . . ?
C18 O3 C19 C20 1.3(19) . . . . ?
C18 C17 C20 C19 2.2(15) . . . . ?
C19 O3 C18 C17 0.3(17) . . . . ?
C20 C17 C18 O3 -1.6(14) . . . . ?
C21 C12 C13 C8 82.3(11) . . . . ?
C21 C12 C16 O2 -80.6(10) . . . . ?
C21 C12 C16 C17 39.9(13) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-16
_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_yg90
_database_code_depnum_ccdc_archive 'CCDC 1483558'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;
_audit_creation_date             2016-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        YG-90
_chemical_formula_moiety         'C21 H16 F2 N2 O3'
_chemical_formula_sum            'C21 H16 F2 N2 O3'
_chemical_formula_weight         382.36
_chemical_absolute_configuration unk
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.9128(5)
_cell_length_b                   13.2459(9)
_cell_length_c                   8.7406(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.323(7)
_cell_angle_gamma                90
_cell_volume                     904.02(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    782
_cell_measurement_temperature    289.97(10)
_cell_measurement_theta_max      21.4530
_cell_measurement_theta_min      3.8690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3576
_diffrn_reflns_point_group_measured_fraction_full 0.671
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.572
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   17.50   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   90.0000 19

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   19.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -90.0000 18

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   29.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   86.50   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000   60.0000 57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0401025000
_diffrn_orient_matrix_UB_12      0.0387486000
_diffrn_orient_matrix_UB_13      0.0371302000
_diffrn_orient_matrix_UB_21      0.0262343000
_diffrn_orient_matrix_UB_22      0.0361150000
_diffrn_orient_matrix_UB_23      -0.0513235000
_diffrn_orient_matrix_UB_31      -0.0771717000
_diffrn_orient_matrix_UB_32      -0.0078784000
_diffrn_orient_matrix_UB_33      -0.0524348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.288
_reflns_Friedel_fraction_full    0.315
_reflns_Friedel_fraction_max     0.314
_reflns_number_gt                1611
_reflns_number_total             2393
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       0.027(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      0.962
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1765
_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. Restrained distances
 O3-C19
 1.36 with sigma of 0.01
3. Rigid bond restraints
 C19, O3
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4.a Ternary CH refined with riding coordinates:
 C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C7(H7), C18(H18), C19(H19), C20(H20)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F1 F -0.4322(6) -0.5282(4) -1.1059(5) 0.0939(15) Uani 1 1 d . . . . .
F2 F -0.5735(7) -0.8097(4) -0.8335(9) 0.131(2) Uani 1 1 d . . . . .
O1 O -0.4713(5) -0.1529(4) -0.5630(5) 0.0735(14) Uani 1 1 d . . . . .
O2 O -0.7201(5) -0.0758(3) -0.5618(5) 0.0642(13) Uani 1 1 d . . . . .
O3 O -1.2067(7) 0.1060(5) -0.7055(6) 0.0968(19) Uani 1 1 d D U . . .
N1 N -0.8518(5) -0.4981(4) -0.7745(5) 0.0478(12) Uani 1 1 d . . . . .
N2 N -1.0144(6) -0.5363(4) -0.7923(6) 0.0565(14) Uani 1 1 d . . . . .
C1 C -0.6372(7) -0.5112(5) -0.9405(7) 0.0533(15) Uani 1 1 d . . . . .
H1 H -0.6535 -0.4436 -0.9677 0.064 Uiso 1 1 calc R . . . .
C2 C -0.5218(9) -0.5706(6) -1.0043(8) 0.0663(18) Uani 1 1 d . . . . .
C3 C -0.4989(9) -0.6699(7) -0.9695(10) 0.077(2) Uani 1 1 d . . . . .
H3 H -0.4219 -0.7089 -1.0138 0.092 Uiso 1 1 calc R . . . .
C4 C -0.5926(9) -0.7103(6) -0.8674(10) 0.074(2) Uani 1 1 d . . . . .
C5 C -0.7070(8) -0.6568(6) -0.7980(8) 0.0603(17) Uani 1 1 d . . . . .
H5 H -0.7690 -0.6869 -0.7285 0.072 Uiso 1 1 calc R . . . .
C6 C -0.7261(6) -0.5552(5) -0.8367(6) 0.0457(14) Uani 1 1 d . . . . .
C7 C -1.1080(7) -0.4597(6) -0.7561(8) 0.0582(17) Uani 1 1 d . . . . .
H7 H -1.2255 -0.4637 -0.7570 0.070 Uiso 1 1 calc R . . . .
C8 C -1.0123(7) -0.3723(5) -0.7164(6) 0.0465(14) Uani 1 1 d . . . . .
C9 C -0.8469(6) -0.3993(4) -0.7274(6) 0.0432(13) Uani 1 1 d . . . . .
C10 C -0.6995(6) -0.3347(5) -0.6735(6) 0.0455(15) Uani 1 1 d . . . . .
C11 C -0.7401(6) -0.2382(5) -0.6555(6) 0.0412(13) Uani 1 1 d . . . . .
C12 C -0.9199(6) -0.1938(5) -0.6962(6) 0.0454(14) Uani 1 1 d . . . . .
C13 C -1.0527(7) -0.2700(5) -0.6582(7) 0.0504(15) Uani 1 1 d . . . . .
H13A H -1.0506 -0.2725 -0.5470 0.060 Uiso 1 1 calc R . . . .
H13B H -1.1664 -0.2494 -0.7069 0.060 Uiso 1 1 calc R . . . .
C14 C -0.5226(7) -0.3785(6) -0.6228(8) 0.0623(18) Uani 1 1 d . . . . .
H14A H -0.4542 -0.3314 -0.5559 0.093 Uiso 1 1 calc GR . . . .
H14B H -0.4697 -0.3912 -0.7123 0.093 Uiso 1 1 calc GR . . . .
H14C H -0.5317 -0.4406 -0.5682 0.093 Uiso 1 1 calc GR . . . .
C15 C -0.6246(7) -0.1570(5) -0.5891(6) 0.0528(15) Uani 1 1 d . . . . .
C16 C -0.9024(7) -0.1001(5) -0.5891(6) 0.0504(15) Uani 1 1 d . . . . .
H16 H -0.9370 -0.1188 -0.4902 0.060 Uiso 1 1 calc R . . . .
C17 C -0.9976(8) -0.0082(5) -0.6489(7) 0.0542(16) Uani 1 1 d . . . . .
C18 C -1.1649(9) 0.0125(6) -0.6406(8) 0.0670(19) Uani 1 1 d . . . . .
H18 H -1.2389 -0.0297 -0.5979 0.080 Uiso 1 1 calc R . . . .
C19 C -1.0640(10) 0.1412(6) -0.7566(9) 0.077(2) Uani 1 1 d D U . . .
H19 H -1.0557 0.2025 -0.8066 0.093 Uiso 1 1 calc R . . . .
C20 C -0.9401(12) 0.0749(6) -0.7242(11) 0.085(2) Uani 1 1 d . . . . .
H20 H -0.8303 0.0822 -0.7478 0.102 Uiso 1 1 calc R . . . .
C21 C -0.9542(7) -0.1655(6) -0.8687(6) 0.0569(16) Uani 1 1 d . . . . .
H21A H -0.9508 -0.2253 -0.9302 0.085 Uiso 1 1 calc GR . . . .
H21B H -0.8681 -0.1190 -0.8904 0.085 Uiso 1 1 calc GR . . . .
H21C H -1.0650 -0.1347 -0.8932 0.085 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
F1 C2 1.345(8) . ?
F2 C4 1.354(8) . ?
O1 C15 1.199(7) . ?
O2 C15 1.359(8) . ?
O2 C16 1.460(7) . ?
O3 C18 1.380(9) . ?
O3 C19 1.362(8) . ?
N1 N2 1.368(6) . ?
N1 C6 1.425(7) . ?
N1 C9 1.370(7) . ?
N2 C7 1.324(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(9) . ?
C1 C6 1.365(8) . ?
C2 C3 1.356(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(11) . ?
C4 C5 1.366(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(9) . ?
C8 C9 1.375(7) . ?
C8 C13 1.500(9) . ?
C9 C10 1.462(8) . ?
C10 C11 1.334(8) . ?
C10 C14 1.513(7) . ?
C11 C12 1.527(7) . ?
C11 C15 1.468(8) . ?
C12 C13 1.532(8) . ?
C12 C16 1.547(9) . ?
C12 C21 1.534(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.481(9) . ?
C17 C18 1.365(9) . ?
C17 C20 1.396(10) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.313(11) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C15 O2 C16 111.1(5) . . ?
C19 O3 C18 106.6(6) . . ?
N2 N1 C6 117.5(5) . . ?
N2 N1 C9 111.5(5) . . ?
C9 N1 C6 129.3(5) . . ?
C7 N2 N1 104.0(5) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C6 C1 C2 118.0(6) . . ?
F1 C2 C1 118.7(7) . . ?
F1 C2 C3 119.1(7) . . ?
C3 C2 C1 122.1(7) . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.5(7) . . ?
C4 C3 H3 121.2 . . ?
F2 C4 C3 118.3(7) . . ?
F2 C4 C5 117.8(8) . . ?
C3 C4 C5 124.0(7) . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.6(7) . . ?
C6 C5 H5 121.7 . . ?
C1 C6 N1 119.6(5) . . ?
C1 C6 C5 121.8(6) . . ?
C5 C6 N1 118.4(6) . . ?
N2 C7 H7 123.5 . . ?
N2 C7 C8 113.1(5) . . ?
C8 C7 H7 123.5 . . ?
C7 C8 C13 134.1(5) . . ?
C9 C8 C7 104.6(6) . . ?
C9 C8 C13 121.1(5) . . ?
N1 C9 C8 106.8(5) . . ?
N1 C9 C10 129.6(5) . . ?
C8 C9 C10 123.0(5) . . ?
C9 C10 C14 121.5(5) . . ?
C11 C10 C9 113.8(5) . . ?
C11 C10 C14 124.2(5) . . ?
C10 C11 C12 125.1(5) . . ?
C10 C11 C15 127.0(5) . . ?
C15 C11 C12 107.9(5) . . ?
C11 C12 C13 110.0(5) . . ?
C11 C12 C16 100.3(4) . . ?
C11 C12 C21 109.4(4) . . ?
C13 C12 C16 113.2(4) . . ?
C13 C12 C21 110.8(5) . . ?
C21 C12 C16 112.5(5) . . ?
C8 C13 C12 109.3(4) . . ?
C8 C13 H13A 109.8 . . ?
C8 C13 H13B 109.8 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
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 . . ?
O1 C15 O2 120.4(6) . . ?
O1 C15 C11 130.9(7) . . ?
O2 C15 C11 108.7(4) . . ?
O2 C16 C12 105.4(5) . . ?
O2 C16 H16 108.7 . . ?
O2 C16 C17 108.0(5) . . ?
C12 C16 H16 108.7 . . ?
C17 C16 C12 117.1(4) . . ?
C17 C16 H16 108.7 . . ?
C18 C17 C16 126.1(6) . . ?
C18 C17 C20 105.0(7) . . ?
C20 C17 C16 128.9(6) . . ?
O3 C18 H18 125.4 . . ?
C17 C18 O3 109.2(7) . . ?
C17 C18 H18 125.4 . . ?
O3 C19 H19 125.4 . . ?
C20 C19 O3 109.3(7) . . ?
C20 C19 H19 125.4 . . ?
C17 C20 H20 125.1 . . ?
C19 C20 C17 109.9(7) . . ?
C19 C20 H20 125.1 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
F1 C2 C3 C4 -179.4(7) . . . . ?
F2 C4 C5 C6 -179.0(6) . . . . ?
O2 C16 C17 C18 -156.7(6) . . . . ?
O2 C16 C17 C20 23.2(9) . . . . ?
O3 C19 C20 C17 0.0(10) . . . . ?
N1 N2 C7 C8 0.5(7) . . . . ?
N1 C9 C10 C11 171.8(5) . . . . ?
N1 C9 C10 C14 -16.2(9) . . . . ?
N2 N1 C6 C1 123.9(6) . . . . ?
N2 N1 C6 C5 -51.3(7) . . . . ?
N2 N1 C9 C8 -0.9(6) . . . . ?
N2 N1 C9 C10 170.1(5) . . . . ?
N2 C7 C8 C9 -1.0(7) . . . . ?
N2 C7 C8 C13 -175.4(6) . . . . ?
C1 C2 C3 C4 -0.6(11) . . . . ?
C2 C1 C6 N1 -176.9(5) . . . . ?
C2 C1 C6 C5 -1.8(9) . . . . ?
C2 C3 C4 F2 178.8(7) . . . . ?
C2 C3 C4 C5 -0.3(12) . . . . ?
C3 C4 C5 C6 0.1(11) . . . . ?
C4 C5 C6 N1 176.2(5) . . . . ?
C4 C5 C6 C1 1.0(9) . . . . ?
C6 N1 N2 C7 -166.8(5) . . . . ?
C6 N1 C9 C8 164.2(5) . . . . ?
C6 N1 C9 C10 -24.8(9) . . . . ?
C6 C1 C2 F1 -179.5(5) . . . . ?
C6 C1 C2 C3 1.7(10) . . . . ?
C7 C8 C9 N1 1.1(6) . . . . ?
C7 C8 C9 C10 -170.7(5) . . . . ?
C7 C8 C13 C12 -157.6(6) . . . . ?
C8 C9 C10 C11 -18.5(8) . . . . ?
C8 C9 C10 C14 153.6(6) . . . . ?
C9 N1 N2 C7 0.2(6) . . . . ?
C9 N1 C6 C1 -40.4(8) . . . . ?
C9 N1 C6 C5 144.4(5) . . . . ?
C9 C8 C13 C12 28.8(7) . . . . ?
C9 C10 C11 C12 -4.1(8) . . . . ?
C9 C10 C11 C15 173.5(5) . . . . ?
C10 C11 C12 C13 36.9(7) . . . . ?
C10 C11 C12 C16 156.4(5) . . . . ?
C10 C11 C12 C21 -85.1(7) . . . . ?
C10 C11 C15 O1 14.8(10) . . . . ?
C10 C11 C15 O2 -167.6(5) . . . . ?
C11 C12 C13 C8 -45.4(6) . . . . ?
C11 C12 C16 O2 25.1(5) . . . . ?
C11 C12 C16 C17 145.1(5) . . . . ?
C12 C11 C15 O1 -167.2(6) . . . . ?
C12 C11 C15 O2 10.4(6) . . . . ?
C12 C16 C17 C18 84.7(8) . . . . ?
C12 C16 C17 C20 -95.4(8) . . . . ?
C13 C8 C9 N1 176.3(5) . . . . ?
C13 C8 C9 C10 4.6(8) . . . . ?
C13 C12 C16 O2 142.2(5) . . . . ?
C13 C12 C16 C17 -97.8(6) . . . . ?
C14 C10 C11 C12 -175.9(5) . . . . ?
C14 C10 C11 C15 1.8(9) . . . . ?
C15 O2 C16 C12 -21.1(6) . . . . ?
C15 O2 C16 C17 -146.9(5) . . . . ?
C15 C11 C12 C13 -141.2(5) . . . . ?
C15 C11 C12 C16 -21.6(5) . . . . ?
C15 C11 C12 C21 96.9(6) . . . . ?
C16 O2 C15 O1 -175.2(5) . . . . ?
C16 O2 C15 C11 6.9(6) . . . . ?
C16 C12 C13 C8 -156.7(5) . . . . ?
C16 C17 C18 O3 178.6(5) . . . . ?
C16 C17 C20 C19 -179.1(6) . . . . ?
C18 O3 C19 C20 -0.8(9) . . . . ?
C18 C17 C20 C19 0.8(9) . . . . ?
C19 O3 C18 C17 1.3(8) . . . . ?
C20 C17 C18 O3 -1.3(7) . . . . ?
C21 C12 C13 C8 75.7(6) . . . . ?
C21 C12 C16 O2 -91.2(5) . . . . ?
C21 C12 C16 C17 28.9(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-13
_olex2_submission_special_instructions 'No special instructions were received'
