# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_R3
_database_code_depnum_ccdc_archive 'CCDC 1033504'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 N O3'
_chemical_formula_sum            'C20 H15 N O3'
_chemical_formula_weight         317.33

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   16.698(3)
_cell_length_b                   5.9368(10)
_cell_length_c                   15.650(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.783(6)
_cell_angle_gamma                90.00
_cell_volume                     1537.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1868
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      21.48

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22347
_diffrn_reflns_av_R_equivalents  0.1825
_diffrn_reflns_av_sigmaI/netI    0.1113
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3152
_reflns_number_gt                1481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0479P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3152
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1720
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL R3 in P2(1)/c
CELL 0.71073 16.6978 5.9368 15.6497 90.000 97.783 90.000
ZERR 4.00 0.0033 0.0010 0.0029 0.000 0.006 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N O
UNIT 80 60 4 12
TEMP 25
ACTA
L.S. 12
SIZE 0.41 0.18 0.15
FMAP 2
PLAN 5
HTAB
BOND $H
CONF
WGHT    0.047900
FVAR       0.18229
N1    3    0.427118    0.246590    0.552199    11.00000    0.03779    0.03497 =
         0.05173   -0.01169    0.00254    0.00307
AFIX  43
H1    2    0.432991    0.119004    0.527775    11.00000   -1.20000
AFIX   0
O1    4    0.599707    0.141326    0.576222    11.00000    0.04437    0.03971 =
         0.06287   -0.01031    0.00924    0.00730
O2    4    0.739821    0.265876    0.655586    11.00000    0.04419    0.05726 =
         0.07661   -0.00709    0.00465    0.01240
O3    4    0.747398    0.584855    0.733558    11.00000    0.03372    0.06495 =
         0.06043   -0.00787    0.00553   -0.00735
 
C1    1    0.354788    0.356560    0.553828    11.00000    0.03623    0.03890 =
         0.04056    0.00006    0.00514    0.00252
C2    1    0.369861    0.557963    0.600015    11.00000    0.03510    0.04186 =
         0.03502   -0.00021    0.01003    0.00543
C3    1    0.306037    0.702920    0.609122    11.00000    0.04692    0.05709 =
         0.04564   -0.00987    0.00629    0.00673
AFIX  43
H3    2    0.315010    0.837345    0.639418    11.00000   -1.20000
AFIX   0
C4    1    0.229351    0.643300    0.572375    11.00000    0.04335    0.07573 =
         0.06045   -0.01629    0.00381    0.01610
AFIX  43
H4    2    0.186285    0.739318    0.577640    11.00000   -1.20000
AFIX   0
C5    1    0.215271    0.441978    0.527553    11.00000    0.03816    0.08914 =
         0.05420   -0.01018    0.00044    0.00297
AFIX  43
H5    2    0.162762    0.405011    0.504045    11.00000   -1.20000
AFIX   0
C6    1    0.277211    0.296192    0.517167    11.00000    0.04053    0.05823 =
         0.05012   -0.01046   -0.00173   -0.00030
AFIX  43
H6    2    0.267583    0.162160    0.486750    11.00000   -1.20000
AFIX   0
C7    1    0.488932    0.373908    0.596112    11.00000    0.03744    0.03209 =
         0.03295   -0.00031    0.00633   -0.00106
C8    1    0.455499    0.568523    0.627846    11.00000    0.04019    0.03381 =
         0.02970   -0.00097    0.00832    0.00222
C9    1    0.505684    0.723021    0.676806    11.00000    0.04311    0.03529 =
         0.04364   -0.00539    0.01057    0.00489
AFIX  43
H9    2    0.484356    0.853559    0.697617    11.00000   -1.20000
AFIX   0
C10   1    0.586732    0.678684    0.693544    11.00000    0.04482    0.03735 =
         0.04252   -0.00234    0.00851   -0.00461
AFIX  43
H10   2    0.620261    0.779503    0.726890    11.00000   -1.20000
AFIX   0
C11   1    0.620588    0.483863    0.661444    11.00000    0.03310    0.03433 =
         0.03750    0.00183    0.00559   -0.00020
C12   1    0.571234    0.330822    0.611054    11.00000    0.03685    0.03028 =
         0.03986    0.00230    0.01108    0.00624
C13   1    0.706798    0.432306    0.681334    11.00000    0.04004    0.04609 =
         0.04339    0.00620    0.00718   -0.00287
C14   1    0.832195    0.541364    0.762322    11.00000    0.03526    0.08480 =
         0.05409    0.00741   -0.00123   -0.00606
AFIX  23
H14A  2    0.840393    0.380271    0.769166    11.00000   -1.20000
H14B  2    0.847272    0.611210    0.818219    11.00000   -1.20000
AFIX   0
C15   1    0.885948    0.629433    0.700587    11.00000    0.03204    0.04308 =
         0.04051    0.00010   -0.00362   -0.00080
C16   1    0.873960    0.841428    0.664685    11.00000    0.05050    0.04561 =
         0.05165   -0.00760   -0.00345    0.00526
AFIX  43
H16   2    0.831366    0.930262    0.677721    11.00000   -1.20000
AFIX   0
C17   1    0.925400    0.921518    0.609292    11.00000    0.07437    0.05301 =
         0.05854    0.01297   -0.00209   -0.01098
AFIX  43
H17   2    0.916802    1.063405    0.584563    11.00000   -1.20000
AFIX   0
C18   1    0.988635    0.793266    0.590821    11.00000    0.05714    0.09184 =
         0.05430    0.01235    0.00868   -0.01441
AFIX  43
H18   2    1.023312    0.848794    0.554071    11.00000   -1.20000
AFIX   0
C19   1    1.001254    0.583525    0.626084    11.00000    0.04486    0.08730 =
         0.06255   -0.00099    0.01149    0.00886
AFIX  43
H19   2    1.044240    0.496077    0.613167    11.00000   -1.20000
AFIX   0
C20   1    0.950070    0.502280    0.680797    11.00000    0.04361    0.04212 =
         0.05769    0.00111   -0.00313    0.00496
AFIX  43
H20   2    0.958852    0.359591    0.704764    11.00000   -1.20000
AFIX   0
H2A   2    0.658306    0.150519    0.599072    11.00000    0.12237
HKLF   4
 
REM  R3 in P2(1)/c
REM R1 =  0.0586 for   1481 Fo > 4sig(Fo)  and  0.1720 for all   3152 data
REM    221 parameters refined using      0 restraints
 
END  
     
WGHT      0.0477      0.0000 
REM Highest difference peak  0.167,  deepest hole -0.215,  1-sigma level  0.040
Q1    1   0.4240  0.1774  0.5368  11.00000  0.05    0.17
Q2    1   0.3568  0.6220  0.6215  11.00000  0.05    0.15
Q3    1   0.3372  0.2459  0.5615  11.00000  0.05    0.15
Q4    1   0.4197  0.6338  0.5977  11.00000  0.05    0.14
Q5    1   1.0803  0.6153  0.5767  11.00000  0.05    0.13
;

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
N1 N 0.42712(12) 0.2466(3) 0.55220(13) 0.0418(6) Uani 1 1 d . . .
H1 H 0.4330 0.1190 0.5278 0.050 Uiso 1 1 calc R . .
O1 O 0.59971(12) 0.1413(3) 0.57622(11) 0.0488(5) Uani 1 1 d . . .
O2 O 0.73982(11) 0.2659(3) 0.65559(13) 0.0597(6) Uani 1 1 d . . .
O3 O 0.74740(10) 0.5849(3) 0.73356(12) 0.0531(5) Uani 1 1 d . . .
C1 C 0.35479(16) 0.3566(4) 0.55383(16) 0.0386(6) Uani 1 1 d . . .
C2 C 0.36986(15) 0.5580(4) 0.60002(15) 0.0368(6) Uani 1 1 d . . .
C3 C 0.30604(17) 0.7029(5) 0.60912(17) 0.0499(8) Uani 1 1 d . . .
H3 H 0.3150 0.8373 0.6394 0.060 Uiso 1 1 calc R . .
C4 C 0.22935(18) 0.6433(6) 0.57238(18) 0.0601(9) Uani 1 1 d . . .
H4 H 0.1863 0.7393 0.5776 0.072 Uiso 1 1 calc R . .
C5 C 0.21527(18) 0.4420(6) 0.52755(18) 0.0610(9) Uani 1 1 d . . .
H5 H 0.1628 0.4050 0.5040 0.073 Uiso 1 1 calc R . .
C6 C 0.27721(16) 0.2962(5) 0.51717(17) 0.0503(8) Uani 1 1 d . . .
H6 H 0.2676 0.1622 0.4867 0.060 Uiso 1 1 calc R . .
C7 C 0.48893(15) 0.3739(4) 0.59611(15) 0.0340(6) Uani 1 1 d . . .
C8 C 0.45550(15) 0.5685(4) 0.62785(15) 0.0342(6) Uani 1 1 d . . .
C9 C 0.50568(16) 0.7230(4) 0.67681(16) 0.0402(7) Uani 1 1 d . . .
H9 H 0.4844 0.8536 0.6976 0.048 Uiso 1 1 calc R . .
C10 C 0.58673(16) 0.6787(4) 0.69354(16) 0.0413(7) Uani 1 1 d . . .
H10 H 0.6203 0.7795 0.7269 0.050 Uiso 1 1 calc R . .
C11 C 0.62059(15) 0.4839(4) 0.66144(16) 0.0349(6) Uani 1 1 d . . .
C12 C 0.57123(15) 0.3308(4) 0.61105(15) 0.0351(6) Uani 1 1 d . . .
C13 C 0.70680(16) 0.4323(5) 0.68133(17) 0.0430(7) Uani 1 1 d . . .
C14 C 0.83219(15) 0.5414(5) 0.76232(18) 0.0587(9) Uani 1 1 d . . .
H14A H 0.8404 0.3803 0.7692 0.070 Uiso 1 1 calc R . .
H14B H 0.8473 0.6112 0.8182 0.070 Uiso 1 1 calc R . .
C15 C 0.88595(15) 0.6294(4) 0.70059(15) 0.0393(7) Uani 1 1 d . . .
C16 C 0.87396(17) 0.8414(5) 0.66469(18) 0.0502(8) Uani 1 1 d . . .
H16 H 0.8314 0.9303 0.6777 0.060 Uiso 1 1 calc R . .
C17 C 0.9254(2) 0.9215(5) 0.60929(19) 0.0630(9) Uani 1 1 d . . .
H17 H 0.9168 1.0634 0.5846 0.076 Uiso 1 1 calc R . .
C18 C 0.9886(2) 0.7933(6) 0.59082(19) 0.0677(10) Uani 1 1 d . . .
H18 H 1.0233 0.8488 0.5541 0.081 Uiso 1 1 calc R . .
C19 C 1.00125(18) 0.5835(6) 0.6261(2) 0.0645(9) Uani 1 1 d . . .
H19 H 1.0442 0.4961 0.6132 0.077 Uiso 1 1 calc R . .
C20 C 0.95007(17) 0.5023(5) 0.68080(17) 0.0487(8) Uani 1 1 d . . .
H20 H 0.9589 0.3596 0.7048 0.058 Uiso 1 1 calc R . .
H2A H 0.658(2) 0.151(6) 0.599(2) 0.122(14) Uiso 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
N1 C1 1.376(3) . ?
N1 C7 1.384(3) . ?
N1 H1 0.8600 . ?
O1 C12 1.363(3) . ?
O1 H2A 1.00(4) . ?
O2 C13 1.226(3) . ?
O3 C13 1.341(3) . ?
O3 C14 1.450(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.392(3) . ?
C2 C8 1.439(3) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.386(3) . ?
C7 C8 1.403(3) . ?
C8 C9 1.399(3) . ?
C9 C10 1.369(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.409(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(3) . ?
C11 C13 1.463(3) . ?
C14 C15 1.499(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.379(3) . ?
C15 C16 1.382(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 109.2(2) . . ?
C1 N1 H1 125.4 . . ?
C7 N1 H1 125.4 . . ?
C12 O1 H2A 101(2) . . ?
C13 O3 C14 117.4(2) . . ?
N1 C1 C6 129.9(2) . . ?
N1 C1 C2 108.5(2) . . ?
C6 C1 C2 121.6(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 C8 133.3(2) . . ?
C1 C2 C8 107.2(2) . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 117.5(3) . . ?
C5 C6 H6 121.2 . . ?
C1 C6 H6 121.2 . . ?
N1 C7 C12 129.7(2) . . ?
N1 C7 C8 108.6(2) . . ?
C12 C7 C8 121.7(2) . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 C2 133.8(2) . . ?
C7 C8 C2 106.5(2) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 C13 118.2(2) . . ?
C10 C11 C13 121.8(2) . . ?
O1 C12 C7 118.4(2) . . ?
O1 C12 C11 123.5(2) . . ?
C7 C12 C11 118.1(2) . . ?
O2 C13 O3 122.1(3) . . ?
O2 C13 C11 124.9(3) . . ?
O3 C13 C11 113.0(2) . . ?
O3 C14 C15 112.5(2) . . ?
O3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
O3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C20 C15 C16 118.8(3) . . ?
C20 C15 C14 120.3(3) . . ?
C16 C15 C14 120.9(3) . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?

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
C7 N1 C1 C6 178.6(3) . . . . ?
C7 N1 C1 C2 -0.4(3) . . . . ?
N1 C1 C2 C3 178.5(2) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
N1 C1 C2 C8 -0.3(3) . . . . ?
C6 C1 C2 C8 -179.4(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C8 C2 C3 C4 178.7(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
N1 C1 C6 C5 -178.7(3) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C1 N1 C7 C12 180.0(2) . . . . ?
C1 N1 C7 C8 0.9(3) . . . . ?
N1 C7 C8 C9 178.4(2) . . . . ?
C12 C7 C8 C9 -0.8(3) . . . . ?
N1 C7 C8 C2 -1.1(3) . . . . ?
C12 C7 C8 C2 179.7(2) . . . . ?
C3 C2 C8 C9 2.9(5) . . . . ?
C1 C2 C8 C9 -178.5(3) . . . . ?
C3 C2 C8 C7 -177.8(3) . . . . ?
C1 C2 C8 C7 0.9(3) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C2 C8 C9 C10 178.5(3) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C9 C10 C11 C13 -178.1(2) . . . . ?
N1 C7 C12 O1 2.8(4) . . . . ?
C8 C7 C12 O1 -178.2(2) . . . . ?
N1 C7 C12 C11 -176.9(2) . . . . ?
C8 C7 C12 C11 2.0(4) . . . . ?
C10 C11 C12 O1 178.6(2) . . . . ?
C13 C11 C12 O1 -3.1(4) . . . . ?
C10 C11 C12 C7 -1.7(4) . . . . ?
C13 C11 C12 C7 176.6(2) . . . . ?
C14 O3 C13 O2 -2.7(4) . . . . ?
C14 O3 C13 C11 175.7(2) . . . . ?
C12 C11 C13 O2 1.6(4) . . . . ?
C10 C11 C13 O2 179.9(2) . . . . ?
C12 C11 C13 O3 -176.8(2) . . . . ?
C10 C11 C13 O3 1.5(3) . . . . ?
C13 O3 C14 C15 87.5(3) . . . . ?
O3 C14 C15 C20 -137.7(2) . . . . ?
O3 C14 C15 C16 44.4(4) . . . . ?
C20 C15 C16 C17 0.6(4) . . . . ?
C14 C15 C16 C17 178.6(2) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C16 C15 C20 C19 -0.3(4) . . . . ?
C14 C15 C20 C19 -178.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_R4
_database_code_depnum_ccdc_archive 'CCDC 1033505'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Cl N O3'
_chemical_formula_sum            'C20 H14 Cl N O3'
_chemical_formula_weight         351.77

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9770(5)
_cell_length_b                   8.8337(6)
_cell_length_c                   14.5708(11)
_cell_angle_alpha                93.367(3)
_cell_angle_beta                 102.682(3)
_cell_angle_gamma                108.417(2)
_cell_volume                     823.26(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9106
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15764
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2901
_reflns_number_gt                2331
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0757P)²+0.5395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2901
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL    R4 in P-1
CELL 0.71073 6.9770 8.8337 14.5708 93.367 102.682 108.417
ZERR 2.00 0.0005 0.0006 0.0011 0.003 0.003 0.002
LATT  1
SFAC    C   H   N   O   CL
UNIT    40  28   2   6   2
MERG    2
L.S.    12
omit -1 50
ACTA
BOND $H
CONF
HTAB
TEMP 25
SIZE 0.38 0.21 0.15
FMAP    2
PLAN    5
WGHT    0.075700    0.539500
FVAR       0.22262
CL1   5    0.638030    0.547635    0.179381    11.00000    0.11560    0.09772 =
         0.08706    0.02269    0.05961    0.01901
N1    3    0.471657    0.233157    0.456793    11.00000    0.05295    0.06470 =
         0.07174    0.01762    0.02168    0.02958
AFIX  43
H1    2    0.569724    0.192266    0.468259    11.00000   -1.20000
AFIX   0
O1    4    0.425696    0.050381    0.611602    11.00000    0.07814    0.07695 =
         0.07748    0.02511    0.01294    0.04392
O2    4    0.210745   -0.036387    0.733393    11.00000    0.11648    0.07921 =
         0.06805    0.02968    0.01069    0.03358
O3    4   -0.064549    0.043586    0.731118    11.00000    0.13852    0.07353 =
         0.07601    0.02780    0.05908    0.03242
C1    1    0.442456    0.329442    0.387637    11.00000    0.05216    0.04771 =
         0.05861    0.00339    0.01585    0.01389
C2    1    0.269745    0.375915    0.392851    11.00000    0.05238    0.03839 =
         0.05444    0.00346    0.01552    0.01277
C3    1    0.212398    0.476195    0.329893    11.00000    0.06729    0.04898 =
         0.06256    0.01191    0.02030    0.02208
AFIX  43
H3    2    0.097686    0.507432    0.331619    11.00000   -1.20000
AFIX   0
C4    1    0.327280    0.528466    0.265179    11.00000    0.08551    0.05223 =
         0.06110    0.01408    0.02313    0.01980
AFIX  43
H4    2    0.291772    0.596657    0.223462    11.00000   -1.20000
AFIX   0
C5    1    0.495704    0.479280    0.262370    11.00000    0.07560    0.05555 =
         0.06011    0.00352    0.02848    0.00556
C6    1    0.557045    0.379266    0.321647    11.00000    0.05990    0.06334 =
         0.07148    0.00535    0.02665    0.01712
AFIX  43
H6    2    0.669636    0.346500    0.317833    11.00000   -1.20000
AFIX   0
C7    1    0.317844    0.213596    0.504228    11.00000    0.04793    0.04447 =
         0.05445    0.00404    0.01083    0.01588
C8    1    0.188333    0.300311    0.467800    11.00000    0.04910    0.03769 =
         0.04986    0.00391    0.01115    0.01452
C9    1    0.021796    0.297322    0.506990    11.00000    0.05263    0.04374 =
         0.06472    0.01058    0.01864    0.01976
AFIX  43
H9    2   -0.066652    0.353458    0.483432    11.00000   -1.20000
AFIX   0
C10   1   -0.009623    0.210781    0.580473    11.00000    0.06049    0.04728 =
         0.06191    0.00736    0.02422    0.01761
AFIX  43
H10   2   -0.121252    0.207922    0.606218    11.00000   -1.20000
AFIX   0
C11   1    0.123000    0.126023    0.617994    11.00000    0.06212    0.03984 =
         0.04887    0.00458    0.01056    0.01265
C12   1    0.289151    0.127419    0.579761    11.00000    0.05646    0.04499 =
         0.05561    0.00601    0.00588    0.01960
C13   1    0.096492    0.036740    0.698917    11.00000    0.09210    0.04839 =
         0.04855    0.00203    0.01319    0.01263
C14   1   -0.102428   -0.036322    0.813798    11.00000    0.24225    0.07366 =
         0.08573    0.02770    0.09269    0.03089
AFIX  23
H14A  2    0.010178   -0.076338    0.838971    11.00000   -1.20000
H14B  2   -0.231863   -0.127057    0.795458    11.00000   -1.20000
AFIX   0
C15   1   -0.115213    0.080543    0.886868    11.00000    0.07345    0.06308 =
         0.04978    0.01942    0.01591    0.01359
C16   1    0.058690    0.187937    0.944742    11.00000    0.10066    0.08763 =
         0.07664    0.02644    0.00700    0.00351
AFIX  43
H16   2    0.187770    0.188548    0.937059    11.00000   -1.20000
AFIX   0
C17   1    0.053324    0.295084    1.013670    11.00000    0.26789    0.07953 =
         0.06646    0.00706   -0.00157   -0.00930
AFIX  43
H17   2    0.173433    0.369072    1.053770    11.00000   -1.20000
AFIX   0
C18   1   -0.135709    0.286100    1.019364    11.00000    0.36357    0.16682 =
         0.19725    0.10435    0.20242    0.18188
AFIX  43
H18   2   -0.138409    0.362882    1.065095    11.00000   -1.20000
AFIX   0
C19   1   -0.318107    0.189917    0.972915    11.00000    0.20168    0.33149 =
         0.25344    0.19367    0.15594    0.19930
AFIX  43
H19   2   -0.443105    0.190230    0.985407    11.00000   -1.20000
AFIX   0
C20   1   -0.301486    0.080346    0.897949    11.00000    0.08383    0.22698 =
         0.10912    0.07542    0.02892    0.06017
AFIX  43
H20   2   -0.422660    0.008988    0.857074    11.00000   -1.20000
AFIX   0
H2A   2    0.381002    0.009092    0.655816    11.00000    0.11138
HKLF   4
 
REM     R4 in P-1
REM R1 =  0.0592 for   2331 Fo > 4sig(Fo)  and  0.0720 for all   2901 data
REM    230 parameters refined using      0 restraints
 
END  
     
WGHT      0.0757      0.5396 
REM Highest difference peak  0.421,  deepest hole -0.355,  1-sigma level  0.047
Q1    1   0.5233  0.4773  0.1265  11.00000  0.05    0.42
Q2    1  -0.2808  0.2146  0.9904  11.00000  0.05    0.34
Q3    1  -0.4666  0.0834  0.9208  11.00000  0.05    0.32
Q4    1  -0.0922  0.3195  1.0396  11.00000  0.05    0.27
Q5    1   0.0144  0.0151  0.8482  11.00000  0.05    0.25
;

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
Cl1 Cl 0.63803(17) 0.54764(12) 0.17938(7) 0.0982(4) Uani 1 1 d . . .
N1 N 0.4717(3) 0.2332(3) 0.45679(16) 0.0594(6) Uani 1 1 d . . .
H1 H 0.5697 0.1923 0.4683 0.071 Uiso 1 1 calc R . .
O1 O 0.4257(4) 0.0504(3) 0.61160(17) 0.0737(6) Uani 1 1 d . . .
O2 O 0.2107(4) -0.0364(3) 0.73339(16) 0.0890(7) Uani 1 1 d . . .
O3 O -0.0645(5) 0.0436(3) 0.73112(17) 0.0908(8) Uani 1 1 d . . .
C1 C 0.4425(4) 0.3294(3) 0.38764(19) 0.0534(6) Uani 1 1 d . . .
C2 C 0.2697(4) 0.3759(3) 0.39285(18) 0.0488(6) Uani 1 1 d . . .
C3 C 0.2124(4) 0.4762(3) 0.32989(19) 0.0582(7) Uani 1 1 d . . .
H3 H 0.0977 0.5074 0.3316 0.070 Uiso 1 1 calc R . .
C4 C 0.3273(5) 0.5285(3) 0.2652(2) 0.0661(8) Uani 1 1 d . . .
H4 H 0.2918 0.5967 0.2235 0.079 Uiso 1 1 calc R . .
C5 C 0.4957(5) 0.4793(3) 0.2624(2) 0.0661(8) Uani 1 1 d . . .
C6 C 0.5570(4) 0.3793(3) 0.3216(2) 0.0643(8) Uani 1 1 d . . .
H6 H 0.6696 0.3465 0.3178 0.077 Uiso 1 1 calc R . .
C7 C 0.3178(4) 0.2136(3) 0.50423(18) 0.0493(6) Uani 1 1 d . . .
C8 C 0.1883(4) 0.3003(3) 0.46780(17) 0.0459(6) Uani 1 1 d . . .
C9 C 0.0218(4) 0.2973(3) 0.50699(19) 0.0521(6) Uani 1 1 d . . .
H9 H -0.0667 0.3535 0.4834 0.062 Uiso 1 1 calc R . .
C10 C -0.0096(4) 0.2108(3) 0.58047(19) 0.0553(6) Uani 1 1 d . . .
H10 H -0.1213 0.2079 0.6062 0.066 Uiso 1 1 calc R . .
C11 C 0.1230(4) 0.1260(3) 0.61799(18) 0.0520(6) Uani 1 1 d . . .
C12 C 0.2892(4) 0.1274(3) 0.57976(19) 0.0531(6) Uani 1 1 d . . .
C13 C 0.0965(6) 0.0367(3) 0.6989(2) 0.0667(8) Uani 1 1 d . . .
C14 C -0.1024(10) -0.0363(5) 0.8138(3) 0.130(2) Uani 1 1 d . . .
H14A H 0.0102 -0.0763 0.8390 0.156 Uiso 1 1 calc R . .
H14B H -0.2319 -0.1271 0.7955 0.156 Uiso 1 1 calc R . .
C15 C -0.1152(5) 0.0805(3) 0.88687(19) 0.0638(7) Uani 1 1 d . . .
C16 C 0.0587(7) 0.1879(5) 0.9447(3) 0.0971(12) Uani 1 1 d . . .
H16 H 0.1878 0.1885 0.9371 0.116 Uiso 1 1 calc R . .
C17 C 0.0533(15) 0.2951(6) 1.0137(3) 0.162(3) Uani 1 1 d . . .
H17 H 0.1734 0.3691 1.0538 0.194 Uiso 1 1 calc R . .
C18 C -0.136(2) 0.2861(11) 1.0194(7) 0.195(5) Uani 1 1 d . . .
H18 H -0.1384 0.3629 1.0651 0.234 Uiso 1 1 calc R . .
C19 C -0.3181(14) 0.1899(15) 0.9729(8) 0.213(6) Uani 1 1 d . . .
H19 H -0.4431 0.1902 0.9854 0.255 Uiso 1 1 calc R . .
C20 C -0.3015(7) 0.0803(8) 0.8979(4) 0.135(2) Uani 1 1 d . . .
H20 H -0.4227 0.0090 0.8571 0.162 Uiso 1 1 calc R . .
H2A H 0.381(7) 0.009(5) 0.656(3) 0.111(16) Uiso 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
Cl1 C5 1.746(3) . ?
N1 C7 1.372(3) . ?
N1 C1 1.379(3) . ?
N1 H1 0.8600 . ?
O1 C12 1.356(3) . ?
O1 H2A 0.83(4) . ?
O2 C13 1.222(4) . ?
O3 C13 1.326(4) . ?
O3 C14 1.463(4) . ?
C1 C6 1.386(4) . ?
C1 C2 1.406(4) . ?
C2 C3 1.394(4) . ?
C2 C8 1.442(3) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(4) . ?
C6 H6 0.9300 . ?
C7 C12 1.389(4) . ?
C7 C8 1.400(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.368(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.407(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(4) . ?
C11 C13 1.469(4) . ?
C14 C15 1.476(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.344(6) . ?
C15 C16 1.346(5) . ?
C16 C17 1.354(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.317(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.292(15) . ?
C18 H18 0.9300 . ?
C19 C20 1.465(12) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 108.5(2) . . ?
C7 N1 H1 125.8 . . ?
C1 N1 H1 125.8 . . ?
C12 O1 H2A 102(3) . . ?
C13 O3 C14 118.1(3) . . ?
N1 C1 C6 129.0(2) . . ?
N1 C1 C2 108.8(2) . . ?
C6 C1 C2 122.2(3) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 C8 134.2(2) . . ?
C1 C2 C8 106.9(2) . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 123.3(3) . . ?
C6 C5 Cl1 118.1(2) . . ?
C4 C5 Cl1 118.7(2) . . ?
C5 C6 C1 116.5(3) . . ?
C5 C6 H6 121.8 . . ?
C1 C6 H6 121.8 . . ?
N1 C7 C12 127.9(2) . . ?
N1 C7 C8 110.0(2) . . ?
C12 C7 C8 122.1(2) . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 C2 135.0(2) . . ?
C7 C8 C2 105.8(2) . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 C13 117.4(3) . . ?
C10 C11 C13 122.5(3) . . ?
O1 C12 C11 124.2(3) . . ?
O1 C12 C7 117.8(3) . . ?
C11 C12 C7 118.0(2) . . ?
O2 C13 O3 123.2(3) . . ?
O2 C13 C11 123.7(3) . . ?
O3 C13 C11 113.1(3) . . ?
O3 C14 C15 108.9(3) . . ?
O3 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
O3 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C20 C15 C16 118.5(4) . . ?
C20 C15 C14 120.5(4) . . ?
C16 C15 C14 121.0(4) . . ?
C15 C16 C17 122.7(5) . . ?
C15 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C18 C17 C16 114.6(6) . . ?
C18 C17 H17 122.7 . . ?
C16 C17 H17 122.7 . . ?
C19 C18 C17 131.7(9) . . ?
C19 C18 H18 114.2 . . ?
C17 C18 H18 114.2 . . ?
C18 C19 C20 110.9(7) . . ?
C18 C19 H19 124.6 . . ?
C20 C19 H19 124.6 . . ?
C15 C20 C19 121.5(6) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C6 -178.8(3) . . . . ?
C7 N1 C1 C2 1.7(3) . . . . ?
N1 C1 C2 C3 179.2(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
N1 C1 C2 C8 -1.3(3) . . . . ?
C6 C1 C2 C8 179.1(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C8 C2 C3 C4 180.0(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C3 C4 C5 Cl1 180.0(2) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
Cl1 C5 C6 C1 179.0(2) . . . . ?
N1 C1 C6 C5 -178.3(3) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
C1 N1 C7 C12 -179.2(2) . . . . ?
C1 N1 C7 C8 -1.3(3) . . . . ?
N1 C7 C8 C9 -179.6(2) . . . . ?
C12 C7 C8 C9 -1.5(4) . . . . ?
N1 C7 C8 C2 0.5(3) . . . . ?
C12 C7 C8 C2 178.5(2) . . . . ?
C3 C2 C8 C9 -0.1(5) . . . . ?
C1 C2 C8 C9 -179.4(3) . . . . ?
C3 C2 C8 C7 179.9(3) . . . . ?
C1 C2 C8 C7 0.5(3) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C2 C8 C9 C10 -179.5(3) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C9 C10 C11 C13 177.9(2) . . . . ?
C10 C11 C12 O1 179.5(2) . . . . ?
C13 C11 C12 O1 0.8(4) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
C13 C11 C12 C7 -179.0(2) . . . . ?
N1 C7 C12 O1 -0.8(4) . . . . ?
C8 C7 C12 O1 -178.4(2) . . . . ?
N1 C7 C12 C11 179.0(2) . . . . ?
C8 C7 C12 C11 1.4(4) . . . . ?
C14 O3 C13 O2 2.0(5) . . . . ?
C14 O3 C13 C11 -177.9(3) . . . . ?
C12 C11 C13 O2 -0.6(4) . . . . ?
C10 C11 C13 O2 -179.2(3) . . . . ?
C12 C11 C13 O3 179.4(2) . . . . ?
C10 C11 C13 O3 0.7(4) . . . . ?
C13 O3 C14 C15 126.5(4) . . . . ?
O3 C14 C15 C20 100.3(5) . . . . ?
O3 C14 C15 C16 -80.7(5) . . . . ?
C20 C15 C16 C17 0.2(6) . . . . ?
C14 C15 C16 C17 -178.8(4) . . . . ?
C15 C16 C17 C18 -0.2(7) . . . . ?
C16 C17 C18 C19 2.5(13) . . . . ?
C17 C18 C19 C20 -4.0(15) . . . . ?
C16 C15 C20 C19 -2.0(7) . . . . ?
C14 C15 C20 C19 177.0(5) . . . . ?
C18 C19 C20 C15 3.6(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_KBr6
_database_code_depnum_ccdc_archive 'CCDC 1033506'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl N O2'
_chemical_formula_sum            'C19 H12 Cl N O2'
_chemical_formula_weight         321.75

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   16.024(5)
_cell_length_b                   15.055(4)
_cell_length_c                   6.3189(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.110(9)
_cell_angle_gamma                90.00
_cell_volume                     1495.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1374
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      18.74

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9250
_diffrn_reflns_av_R_equivalents  0.2334
_diffrn_reflns_av_sigmaI/netI    0.2129
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2628
_reflns_number_gt                1007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0221P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2628
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2330
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL KBR6 in P21/c
CELL  0.71073  16.0235  15.0553   6.3189   90.000  101.110   90.000
ZERR 4.00 0.0047 0.0038 0.0018 0.000 0.009 0.000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C H N O CL
UNIT 76 48 4 8 4
L.S. 12
OMIT -1 50
ACTA
HTAB
BOND $H
CONF
SIZE 0.28 0.13 0.05
BOND
FMAP 2
PLAN 5
WGHT    0.022100
FVAR       0.34300
CL1   5   -0.114623    0.633131    0.081042    11.00000    0.04440    0.13449 =
         0.14147   -0.01153   -0.00530   -0.00503
N1    3    0.540757    0.575995    0.754726    11.00000    0.04969    0.04076 =
         0.03733    0.00740   -0.00138    0.00669
AFIX  43
H1    2    0.553110    0.550375    0.878457    11.00000   -1.20000
AFIX   0
O1    4    0.385096    0.551995    0.911739    11.00000    0.05839    0.06784 =
         0.03534    0.01666    0.01558    0.00780
AFIX 147
H1A   2    0.337419    0.553973    0.940827    11.00000   -1.50000
AFIX   0
O2    4    0.226707    0.588675    0.846062    11.00000    0.06822    0.10357 =
         0.04245    0.01200    0.01958    0.00587
C1    1    0.466067    0.640836    0.453973    11.00000    0.04365    0.03262 =
         0.03113   -0.00284    0.00930   -0.00092
C2    1    0.459631    0.600075    0.649984    11.00000    0.04615    0.03317 =
         0.02715   -0.00443    0.00573    0.00255
C3    1    0.383621    0.590569    0.717540    11.00000    0.05383    0.03036 =
         0.02997   -0.00049    0.01265    0.00077
C4    1    0.308620    0.621241    0.583797    11.00000    0.04641    0.04388 =
         0.03344   -0.00238    0.00432    0.00023
C5    1    0.316127    0.664064    0.387241    11.00000    0.04632    0.04249 =
         0.03524    0.00267   -0.00592    0.00038
AFIX  43
H5    2    0.267055    0.685644    0.299171    11.00000   -1.20000
AFIX   0
C6    1    0.391489    0.674874    0.322354    11.00000    0.05533    0.03718 =
         0.03342    0.00341    0.00441   -0.00518
AFIX  43
H6    2    0.394003    0.704058    0.194017    11.00000   -1.20000
AFIX   0
C7    1    0.553780    0.639450    0.438833    11.00000    0.04615    0.02984 =
         0.03868    0.00573    0.01078    0.00129
C8    1    0.598175    0.599742    0.628608    11.00000    0.04230    0.03945 =
         0.03986   -0.00110    0.00593   -0.00095
C9    1    0.685653    0.589754    0.669400    11.00000    0.04873    0.05281 =
         0.06201   -0.00113    0.00702    0.00643
AFIX  43
H9    2    0.714073    0.562895    0.795382    11.00000   -1.20000
AFIX   0
C10   1    0.728591    0.620648    0.518537    11.00000    0.05313    0.05941 =
         0.08605    0.00367    0.01475    0.00222
AFIX  43
H10   2    0.787443    0.614796    0.542587    11.00000   -1.20000
AFIX   0
C11   1    0.686250    0.661264    0.326881    11.00000    0.06169    0.05432 =
         0.07938    0.00221    0.03301   -0.00744
AFIX  43
H11   2    0.717053    0.681543    0.225950    11.00000   -1.20000
AFIX   0
C12   1    0.598418    0.670980    0.288871    11.00000    0.06049    0.04251 =
         0.05501    0.00332    0.01382    0.00211
AFIX  43
H12   2    0.570098    0.698453    0.163629    11.00000   -1.20000
AFIX   0
C13   1    0.228373    0.608549    0.655462    11.00000    0.05473    0.04535 =
         0.04692   -0.00157    0.00962    0.00217
C14   1    0.145356    0.618241    0.504392    11.00000    0.03959    0.04881 =
         0.04180   -0.00400    0.01378    0.00491
C15   1    0.077841    0.653817    0.581442    11.00000    0.06599    0.07582 =
         0.06056   -0.01057    0.02269    0.00418
AFIX  43
H15   2    0.086480    0.675032    0.722208    11.00000   -1.20000
AFIX   0
C16   1   -0.003039    0.658696    0.453125    11.00000    0.05113    0.08501 =
         0.10356   -0.01510    0.03305    0.00446
AFIX  43
H16   2   -0.048353    0.682443    0.506786    11.00000   -1.20000
AFIX   0
C17   1   -0.014264    0.627475    0.244738    11.00000    0.03757    0.07012 =
         0.08647   -0.00249    0.01225   -0.00700
C18   1    0.051590    0.592321    0.164082    11.00000    0.05027    0.06473 =
         0.05852   -0.00641    0.01234   -0.00994
AFIX  43
H18   2    0.042828    0.571030    0.023372    11.00000   -1.20000
AFIX   0
C19   1    0.131323    0.588718    0.293632    11.00000    0.04002    0.06310 =
         0.05525   -0.00362    0.01075   -0.00603
AFIX  43
H19   2    0.176543    0.565944    0.237904    11.00000   -1.20000
HKLF   4
 
REM  KBR6 in P21/c
REM R1 =  0.0675 for   1007 Fo > 4sig(Fo)  and  0.2330 for all   2628 data
REM    209 parameters refined using      0 restraints
 
END  
     
WGHT      0.0221      0.0000 
REM Highest difference peak  0.208,  deepest hole -0.229,  1-sigma level  0.054
Q1    1   0.2370  0.7382  0.5255  11.00000  0.05    0.21
Q2    1   0.0628  0.5602  0.2894  11.00000  0.05    0.18
Q3    1   0.0175  0.4985  0.2152  11.00000  0.05    0.18
Q4    1   0.4891  0.7424  0.4616  11.00000  0.05    0.18
Q5    1   0.3437  0.5827  0.5017  11.00000  0.05    0.17
;

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
Cl1 Cl -0.11462(7) 0.63313(11) 0.0810(2) 0.1099(7) Uani 1 1 d . . .
N1 N 0.5408(2) 0.5760(2) 0.7547(5) 0.0439(10) Uani 1 1 d . . .
H1 H 0.5531 0.5504 0.8785 0.053 Uiso 1 1 calc R . .
O1 O 0.38510(16) 0.5520(2) 0.9117(4) 0.0530(9) Uani 1 1 d . . .
H1A H 0.3374 0.5540 0.9408 0.079 Uiso 1 1 calc R . .
O2 O 0.22671(17) 0.5887(2) 0.8461(5) 0.0702(10) Uani 1 1 d . . .
C1 C 0.4661(2) 0.6408(2) 0.4540(6) 0.0355(11) Uani 1 1 d . . .
C2 C 0.4596(3) 0.6001(3) 0.6500(6) 0.0357(11) Uani 1 1 d . . .
C3 C 0.3836(3) 0.5906(3) 0.7175(6) 0.0374(11) Uani 1 1 d . . .
C4 C 0.3086(3) 0.6212(3) 0.5838(6) 0.0417(11) Uani 1 1 d . . .
C5 C 0.3161(3) 0.6641(3) 0.3872(7) 0.0432(12) Uani 1 1 d . . .
H5 H 0.2671 0.6856 0.2992 0.052 Uiso 1 1 calc R . .
C6 C 0.3915(3) 0.6749(3) 0.3224(6) 0.0425(12) Uani 1 1 d . . .
H6 H 0.3940 0.7041 0.1940 0.051 Uiso 1 1 calc R . .
C7 C 0.5538(2) 0.6395(3) 0.4388(6) 0.0379(11) Uani 1 1 d . . .
C8 C 0.5982(3) 0.5997(3) 0.6286(6) 0.0408(11) Uani 1 1 d . . .
C9 C 0.6857(3) 0.5898(3) 0.6694(7) 0.0550(13) Uani 1 1 d . . .
H9 H 0.7141 0.5629 0.7954 0.066 Uiso 1 1 calc R . .
C10 C 0.7286(3) 0.6206(3) 0.5185(9) 0.0660(15) Uani 1 1 d . . .
H10 H 0.7874 0.6148 0.5426 0.079 Uiso 1 1 calc R . .
C11 C 0.6863(3) 0.6613(3) 0.3269(8) 0.0625(14) Uani 1 1 d . . .
H11 H 0.7171 0.6815 0.2259 0.075 Uiso 1 1 calc R . .
C12 C 0.5984(3) 0.6710(3) 0.2889(7) 0.0523(13) Uani 1 1 d . . .
H12 H 0.5701 0.6985 0.1636 0.063 Uiso 1 1 calc R . .
C13 C 0.2284(3) 0.6085(3) 0.6555(7) 0.0490(13) Uani 1 1 d . . .
C14 C 0.1454(3) 0.6182(3) 0.5044(7) 0.0426(11) Uani 1 1 d . . .
C15 C 0.0778(3) 0.6538(3) 0.5814(7) 0.0661(15) Uani 1 1 d . . .
H15 H 0.0865 0.6750 0.7222 0.079 Uiso 1 1 calc R . .
C16 C -0.0030(3) 0.6587(3) 0.4531(9) 0.0775(17) Uani 1 1 d . . .
H16 H -0.0484 0.6824 0.5068 0.093 Uiso 1 1 calc R . .
C17 C -0.0143(3) 0.6275(3) 0.2447(9) 0.0647(15) Uani 1 1 d . . .
C18 C 0.0516(3) 0.5923(3) 0.1641(7) 0.0576(13) Uani 1 1 d . . .
H18 H 0.0428 0.5710 0.0234 0.069 Uiso 1 1 calc R . .
C19 C 0.1313(3) 0.5887(3) 0.2936(7) 0.0526(13) Uani 1 1 d . . .
H19 H 0.1765 0.5659 0.2379 0.063 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
Cl1 C17 1.738(4) . ?
N1 C8 1.375(4) . ?
N1 C2 1.388(4) . ?
N1 H1 0.8600 . ?
O1 C3 1.354(4) . ?
O1 H1A 0.8200 . ?
O2 C13 1.246(4) . ?
C1 C2 1.404(5) . ?
C1 C6 1.414(5) . ?
C1 C7 1.427(5) . ?
C2 C3 1.373(5) . ?
C3 C4 1.407(5) . ?
C4 C5 1.425(5) . ?
C4 C13 1.456(5) . ?
C5 C6 1.358(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.377(5) . ?
C7 C8 1.405(5) . ?
C8 C9 1.384(5) . ?
C9 C10 1.361(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.409(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.488(5) . ?
C14 C15 1.377(5) . ?
C14 C19 1.381(5) . ?
C15 C16 1.392(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(6) . ?
C18 C19 1.379(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C2 109.0(3) . . ?
C8 N1 H1 125.5 . . ?
C2 N1 H1 125.5 . . ?
C3 O1 H1A 109.5 . . ?
C2 C1 C6 118.7(4) . . ?
C2 C1 C7 107.1(3) . . ?
C6 C1 C7 134.2(4) . . ?
C3 C2 N1 129.0(4) . . ?
C3 C2 C1 122.7(4) . . ?
N1 C2 C1 108.3(4) . . ?
O1 C3 C2 117.7(3) . . ?
O1 C3 C4 123.3(4) . . ?
C2 C3 C4 119.0(4) . . ?
C3 C4 C5 117.8(4) . . ?
C3 C4 C13 118.3(4) . . ?
C5 C4 C13 124.0(4) . . ?
C6 C5 C4 123.1(4) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C12 C7 C8 119.3(4) . . ?
C12 C7 C1 133.6(4) . . ?
C8 C7 C1 107.0(4) . . ?
N1 C8 C9 129.1(4) . . ?
N1 C8 C7 108.7(3) . . ?
C9 C8 C7 122.2(4) . . ?
C10 C9 C8 117.6(4) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 121.7(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C7 C12 C11 119.2(4) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
O2 C13 C4 121.1(4) . . ?
O2 C13 C14 117.4(4) . . ?
C4 C13 C14 121.4(4) . . ?
C15 C14 C19 118.2(4) . . ?
C15 C14 C13 118.5(4) . . ?
C19 C14 C13 123.1(4) . . ?
C14 C15 C16 121.4(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 118.3(5) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C18 C17 C16 121.5(4) . . ?
C18 C17 Cl1 119.4(4) . . ?
C16 C17 Cl1 119.2(4) . . ?
C17 C18 C19 119.2(4) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C14 121.3(4) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?

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
C8 N1 C2 C3 -178.8(4) . . . . ?
C8 N1 C2 C1 -0.6(4) . . . . ?
C6 C1 C2 C3 1.1(6) . . . . ?
C7 C1 C2 C3 179.5(3) . . . . ?
C6 C1 C2 N1 -177.2(3) . . . . ?
C7 C1 C2 N1 1.2(4) . . . . ?
N1 C2 C3 O1 -0.6(6) . . . . ?
C1 C2 C3 O1 -178.5(4) . . . . ?
N1 C2 C3 C4 179.2(4) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
O1 C3 C4 C5 177.4(4) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
O1 C3 C4 C13 -1.8(6) . . . . ?
C2 C3 C4 C13 178.4(4) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C13 C4 C5 C6 -179.6(4) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C2 C1 C6 C5 -2.2(6) . . . . ?
C7 C1 C6 C5 179.9(4) . . . . ?
C2 C1 C7 C12 -178.2(4) . . . . ?
C6 C1 C7 C12 -0.1(8) . . . . ?
C2 C1 C7 C8 -1.4(4) . . . . ?
C6 C1 C7 C8 176.7(4) . . . . ?
C2 N1 C8 C9 179.1(4) . . . . ?
C2 N1 C8 C7 -0.3(4) . . . . ?
C12 C7 C8 N1 178.3(4) . . . . ?
C1 C7 C8 N1 1.0(4) . . . . ?
C12 C7 C8 C9 -1.1(6) . . . . ?
C1 C7 C8 C9 -178.4(4) . . . . ?
N1 C8 C9 C10 -178.8(4) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C9 C10 C11 C12 0.3(7) . . . . ?
C8 C7 C12 C11 1.2(6) . . . . ?
C1 C7 C12 C11 177.7(4) . . . . ?
C10 C11 C12 C7 -0.9(6) . . . . ?
C3 C4 C13 O2 14.8(6) . . . . ?
C5 C4 C13 O2 -164.3(4) . . . . ?
C3 C4 C13 C14 -164.8(4) . . . . ?
C5 C4 C13 C14 16.1(6) . . . . ?
O2 C13 C14 C15 35.8(6) . . . . ?
C4 C13 C14 C15 -144.6(4) . . . . ?
O2 C13 C14 C19 -140.5(5) . . . . ?
C4 C13 C14 C19 39.2(6) . . . . ?
C19 C14 C15 C16 1.2(7) . . . . ?
C13 C14 C15 C16 -175.2(4) . . . . ?
C14 C15 C16 C17 -0.5(8) . . . . ?
C15 C16 C17 C18 0.1(8) . . . . ?
C15 C16 C17 Cl1 -179.8(4) . . . . ?
C16 C17 C18 C19 -0.6(8) . . . . ?
Cl1 C17 C18 C19 179.4(3) . . . . ?
C17 C18 C19 C14 1.4(7) . . . . ?
C15 C14 C19 C18 -1.7(7) . . . . ?
C13 C14 C19 C18 174.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.054
