# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_o095_w
_database_code_depnum_ccdc_archive 'CCDC 1481743'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-06-14 downloaded from the CCDC.
;
_audit_creation_date             2015-12-03
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H15 N O)'
_chemical_formula_sum            'C40 H30 N2 O2'
_chemical_formula_weight         570.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H24 N O'
_chemical_oxdiff_usercomment     Koenig_Das
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2874(3)
_cell_length_b                   14.4206(5)
_cell_length_c                   15.0229(6)
_cell_angle_alpha                64.011(4)
_cell_angle_beta                 79.684(3)
_cell_angle_gamma                83.373(3)
_cell_volume                     1394.94(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11039
_cell_measurement_temperature    123.0(3)
_cell_measurement_theta_max      73.8360
_cell_measurement_theta_min      3.2880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.37b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 8 0.0216
0 1 -8 0.0181
5 -1 0 0.1178
-5 1 0 0.1178
0 9 5 0.0246
0 -9 -5 0.0066
2 9 6 0.0545

_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.031
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -0.9991 8.0005 0.0479 -0.1280 0.9694
-0.0000 0.9991 -8.0005 -0.0479 0.1280 -0.9694
5.0000 -1.0006 -0.0003 -0.5542 0.9321 0.0716
-5.0000 1.0006 0.0003 0.5542 -0.9321 -0.0716
0.0000 9.0001 4.9998 -0.7075 -0.6700 -0.0414
-0.0000 -9.0001 -4.9998 0.7075 0.6700 0.0414
2.0000 9.0000 5.9998 -0.9634 -0.3453 0.0732

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19204
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.897
_diffrn_reflns_theta_min         3.307
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1818
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  29.00   0.50    6.00    --  -43.14  37.00-180.00  156
  2  ω   -122.00  -4.00   0.50    6.00    --  -43.14 -15.00  -3.00  236
  3  ω     34.00 130.00   0.50    6.00    --   43.14-178.00  60.00  192
  4  ω     31.00  91.00   0.50   21.00    --  104.50 -30.00 120.00  120
  5  ω     26.00 144.00   0.50   21.00    --  104.50 -15.00 -60.00  236
  6  ω     30.00 136.00   0.50   21.00    --  104.50 -77.00 120.00  212
  7  ω     31.00  91.00   0.50   21.00    --  104.50 -30.00-180.00  120
  8  ω     31.00  91.00   0.50   21.00    --  104.50 -30.00-120.00  120
  9  ω     30.00 136.00   0.50   21.00    --  104.50 -77.00 -30.00  212
 10  ω     31.00 121.00   0.50   21.00    --  104.50-125.00 -30.00  180
 11  ω     31.00  91.00   0.50   21.00    --  104.50 -30.00  60.00  120
 12  ω   -117.00 -12.00   0.50    6.00    --  -43.14 -77.00-150.00  210
 13  ω   -113.00 -18.00   0.50    6.00    --  -43.14 -57.00 -60.00  190
 14  ω     18.00 113.00   0.50    6.00    --   43.14  57.00 120.00  190
 15  ω     73.00 178.00   0.50   21.00    --  104.50  77.00-180.00  210
 16  ω     78.00 178.00   0.50   21.00    --  104.50  30.00 120.00  200
 17  ω     78.00 174.00   0.50   21.00    --  104.50  61.00 -90.00  192
 18  ω     80.00 175.00   0.50   21.00    --  104.50  45.00 150.00  190
 19  ω     73.00 178.00   0.50   21.00    --  104.50  77.00  30.00  210
 20  ω     78.00 178.00   0.50   21.00    --  104.50  30.00   0.00  200
 21  ω   -124.00 -79.00   0.50    6.00    --  -43.14 -99.00 -90.00   90
 22  ω     12.00 117.00   0.50    6.00    --   43.14  77.00-180.00  210
 23  ω     12.00 117.00   0.50    6.00    --   43.14  77.00   0.00  210
 24  ω     80.00 105.00   0.50   21.00    --  104.50  45.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1261715000
_diffrn_orient_matrix_UB_12      -0.0766146000
_diffrn_orient_matrix_UB_13      -0.0035859000
_diffrn_orient_matrix_UB_21      0.1741591000
_diffrn_orient_matrix_UB_22      -0.0613010000
_diffrn_orient_matrix_UB_23      -0.0236544000
_diffrn_orient_matrix_UB_31      0.0008773000
_diffrn_orient_matrix_UB_32      -0.0672464000
_diffrn_orient_matrix_UB_33      0.1127738000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'gradient vaccum rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4836
_reflns_number_total             5457
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.029
_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)+(0.1145P)²+0.3763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1658
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C28(H28), C5(H5), C4(H4), C20(H20), C14(H14), C10(H10), C9(H9),
 C25(H25), C24(H24), C29(H29), C34(H34), C33(H33), C19(H19), C40(H40), C32(H32),
  C11(H11), C39(H39), C16(H16), C36(H36), C18(H18), C37(H37), C17(H17), C38(H38)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.90983(17) 0.91015(8) 0.62220(8) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.36243(18) 0.59061(9) 0.40133(9) 0.0323(3) Uani 1 1 d . . . . .
N1 N 0.91653(17) 0.86872(9) 0.30456(9) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.44650(17) 0.63238(9) 0.70835(9) 0.0183(3) Uani 1 1 d . . . . .
C30 C 0.42942(19) 0.77693(11) 0.75372(11) 0.0186(3) Uani 1 1 d . . . . .
C31 C 0.4566(2) 0.66836(11) 0.78018(11) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.90734(19) 0.84073(11) 0.47739(11) 0.0185(3) Uani 1 1 d . . . . .
H8 H 0.9188 0.9110 0.4570 0.022 Uiso 1 1 calc R . . . .
C13 C 0.88158(19) 0.72588(11) 0.26343(11) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.90021(19) 0.77328(11) 0.57739(11) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.87415(19) 0.69754(11) 0.43695(11) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.91027(19) 0.83354(11) 0.23164(11) 0.0181(3) Uani 1 1 d . . . . .
C26 C 0.39621(19) 0.80565(11) 0.58467(11) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.89734(19) 0.80353(11) 0.40703(11) 0.0175(3) Uani 1 1 d . . . . .
C27 C 0.41438(19) 0.69828(11) 0.61114(11) 0.0179(3) Uani 1 1 d . . . . .
C23 C 0.3789(2) 0.72792(12) 0.44475(12) 0.0200(3) Uani 1 1 d . . . . .
C28 C 0.4031(2) 0.66036(11) 0.54143(11) 0.0198(3) Uani 1 1 d . . . . .
H28 H 0.4118 0.5896 0.5601 0.024 Uiso 1 1 calc R . . . .
C35 C 0.4291(2) 0.81499(11) 0.83101(11) 0.0191(3) Uani 1 1 d . . . . .
C5 C 0.8647(2) 0.63102(11) 0.53891(11) 0.0208(3) Uani 1 1 d . . . . .
H5 H 0.8477 0.5611 0.5603 0.025 Uiso 1 1 calc R . . . .
C4 C 0.8800(2) 0.66733(11) 0.60837(11) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.8771 0.6217 0.6755 0.024 Uiso 1 1 calc R . . . .
C2 C 0.9173(2) 0.81689(12) 0.64926(11) 0.0200(3) Uani 1 1 d . . . . .
C20 C 0.7919(2) 0.73972(12) 0.10317(12) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.7225 0.8003 0.0960 0.025 Uiso 1 1 calc R . . . .
C14 C 0.8640(2) 0.66121(11) 0.36250(11) 0.0196(3) Uani 1 1 d . . . . .
H14 H 0.8449 0.5917 0.3829 0.023 Uiso 1 1 calc R . . . .
C10 C 0.9819(2) 1.00067(11) 0.15683(12) 0.0224(3) Uani 1 1 d . . . . .
H10 H 1.0116 1.0663 0.1077 0.027 Uiso 1 1 calc R . . . .
C9 C 0.9612(2) 0.97092(11) 0.25749(11) 0.0209(3) Uani 1 1 d . . . . .
H9 H 0.9748 1.0124 0.2888 0.025 Uiso 1 1 calc R . . . .
C25 C 0.3699(2) 0.87237(11) 0.48612(12) 0.0209(3) Uani 1 1 d . . . . .
H25 H 0.3567 0.9432 0.4672 0.025 Uiso 1 1 calc R . . . .
C24 C 0.3633(2) 0.83487(11) 0.41689(11) 0.0208(3) Uani 1 1 d . . . . .
H24 H 0.3484 0.8804 0.3515 0.025 Uiso 1 1 calc R . . . .
C29 C 0.4033(2) 0.84252(11) 0.65875(11) 0.0193(3) Uani 1 1 d . . . . .
H29 H 0.3896 0.9131 0.6411 0.023 Uiso 1 1 calc R . . . .
C15 C 0.8856(2) 0.68732(11) 0.18581(11) 0.0190(3) Uani 1 1 d . . . . .
C34 C 0.4863(2) 0.52750(11) 0.74847(11) 0.0209(3) Uani 1 1 d . . . . .
H34 H 0.4894 0.4850 0.7162 0.025 Uiso 1 1 calc R . . . .
C33 C 0.5204(2) 0.49700(11) 0.84400(11) 0.0223(3) Uani 1 1 d . . . . .
H33 H 0.5504 0.4298 0.8881 0.027 Uiso 1 1 calc R . . . .
C19 C 0.8009(2) 0.70248(12) 0.03136(12) 0.0227(3) Uani 1 1 d . . . . .
H19 H 0.7371 0.7380 -0.0233 0.027 Uiso 1 1 calc R . . . .
C40 C 0.3239(2) 0.76746(11) 0.92549(12) 0.0212(3) Uani 1 1 d . . . . .
H40 H 0.2587 0.7092 0.9413 0.025 Uiso 1 1 calc R . . . .
C32 C 0.5026(2) 0.58419(11) 0.86474(11) 0.0207(3) Uani 1 1 d . . . . .
H32 H 0.5189 0.5849 0.9244 0.025 Uiso 1 1 calc R . . . .
C1 C 0.9444(2) 0.74408(12) 0.75475(11) 0.0234(3) Uani 1 1 d . . . . .
H1A H 0.9688 0.7827 0.7893 0.035 Uiso 1 1 calc GR . . . .
H1B H 1.0482 0.6969 0.7537 0.035 Uiso 1 1 calc GR . . . .
H1C H 0.8336 0.7061 0.7886 0.035 Uiso 1 1 calc GR . . . .
C22 C 0.3718(2) 0.68352(12) 0.37211(12) 0.0229(3) Uani 1 1 d . . . . .
C11 C 0.9507(2) 0.91571(11) 0.13961(11) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.9563 0.9151 0.0775 0.025 Uiso 1 1 calc R . . . .
C39 C 0.3156(2) 0.80620(12) 0.99593(12) 0.0235(3) Uani 1 1 d . . . . .
H39 H 0.2445 0.7741 1.0584 0.028 Uiso 1 1 calc R . . . .
C16 C 0.9907(2) 0.59684(12) 0.19445(12) 0.0234(3) Uani 1 1 d . . . . .
H16 H 1.0548 0.5611 0.2489 0.028 Uiso 1 1 calc R . . . .
C36 C 0.5288(2) 0.90111(11) 0.80971(12) 0.0217(3) Uani 1 1 d . . . . .
H36 H 0.6012 0.9331 0.7476 0.026 Uiso 1 1 calc R . . . .
C18 C 0.9046(2) 0.61255(12) 0.04085(12) 0.0250(3) Uani 1 1 d . . . . .
H18 H 0.9101 0.5876 -0.0072 0.030 Uiso 1 1 calc R . . . .
C37 C 0.5208(2) 0.93934(12) 0.88068(13) 0.0260(3) Uani 1 1 d . . . . .
H37 H 0.5882 0.9966 0.8659 0.031 Uiso 1 1 calc R . . . .
C17 C 1.0000(2) 0.56000(12) 0.12215(13) 0.0265(4) Uani 1 1 d . . . . .
H17 H 1.0704 0.5000 0.1284 0.032 Uiso 1 1 calc R . . . .
C38 C 0.4129(2) 0.89273(12) 0.97342(12) 0.0250(3) Uani 1 1 d . . . . .
H38 H 0.4058 0.9193 1.0203 0.030 Uiso 1 1 calc R . . . .
C21 C 0.3784(2) 0.75541(13) 0.26329(12) 0.0271(4) Uani 1 1 d . . . . .
H21A H 0.3878 0.7160 0.2250 0.041 Uiso 1 1 calc GR . . . .
H21B H 0.4849 0.7974 0.2417 0.041 Uiso 1 1 calc GR . . . .
H21C H 0.2666 0.7988 0.2534 0.041 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2202(18) . ?
O2 C22 1.220(2) . ?
N1 C12 1.4035(17) . ?
N1 C7 1.3993(19) . ?
N1 C9 1.3759(18) . ?
N2 C31 1.4027(17) . ?
N2 C27 1.395(2) . ?
N2 C34 1.3774(18) . ?
C30 C31 1.435(2) . ?
C30 C35 1.4852(19) . ?
C30 C29 1.356(2) . ?
C31 C32 1.381(2) . ?
C8 H8 0.9300 . ?
C8 C3 1.382(2) . ?
C8 C7 1.3943(19) . ?
C13 C12 1.439(2) . ?
C13 C14 1.358(2) . ?
C13 C15 1.4907(18) . ?
C3 C4 1.406(2) . ?
C3 C2 1.4958(19) . ?
C6 C7 1.413(2) . ?
C6 C5 1.400(2) . ?
C6 C14 1.4433(19) . ?
C12 C11 1.379(2) . ?
C26 C27 1.416(2) . ?
C26 C25 1.402(2) . ?
C26 C29 1.4385(19) . ?
C27 C28 1.3949(19) . ?
C23 C28 1.379(2) . ?
C23 C24 1.406(2) . ?
C23 C22 1.4979(19) . ?
C28 H28 0.9300 . ?
C35 C40 1.397(2) . ?
C35 C36 1.396(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C2 C1 1.503(2) . ?
C20 H20 0.9300 . ?
C20 C15 1.393(2) . ?
C20 C19 1.390(2) . ?
C14 H14 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.363(2) . ?
C10 C11 1.408(2) . ?
C9 H9 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.376(2) . ?
C24 H24 0.9300 . ?
C29 H29 0.9300 . ?
C15 C16 1.401(2) . ?
C34 H34 0.9300 . ?
C34 C33 1.365(2) . ?
C33 H33 0.9300 . ?
C33 C32 1.409(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.387(2) . ?
C40 H40 0.9300 . ?
C40 C39 1.387(2) . ?
C32 H32 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C22 C21 1.499(2) . ?
C11 H11 0.9300 . ?
C39 H39 0.9300 . ?
C39 C38 1.387(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.392(2) . ?
C36 H36 0.9300 . ?
C36 C37 1.389(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.386(2) . ?
C37 H37 0.9300 . ?
C37 C38 1.386(2) . ?
C17 H17 0.9300 . ?
C38 H38 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
C7 N1 C12 122.88(12) . . ?
C9 N1 C12 108.82(12) . . ?
C9 N1 C7 128.02(12) . . ?
C27 N2 C31 122.57(12) . . ?
C34 N2 C31 108.80(12) . . ?
C34 N2 C27 128.47(12) . . ?
C31 C30 C35 119.36(13) . . ?
C29 C30 C31 119.22(13) . . ?
C29 C30 C35 121.42(13) . . ?
N2 C31 C30 119.02(13) . . ?
C32 C31 N2 107.18(12) . . ?
C32 C31 C30 133.71(13) . . ?
C3 C8 H8 120.0 . . ?
C3 C8 C7 120.01(13) . . ?
C7 C8 H8 120.0 . . ?
C12 C13 C15 118.73(13) . . ?
C14 C13 C12 119.31(13) . . ?
C14 C13 C15 121.81(13) . . ?
C8 C3 C4 119.97(13) . . ?
C8 C3 C2 117.79(13) . . ?
C4 C3 C2 122.24(13) . . ?
C7 C6 C14 119.60(14) . . ?
C5 C6 C7 118.05(13) . . ?
C5 C6 C14 122.34(13) . . ?
N1 C12 C13 118.71(13) . . ?
C11 C12 N1 107.09(12) . . ?
C11 C12 C13 133.96(13) . . ?
C27 C26 C29 119.64(14) . . ?
C25 C26 C27 117.98(13) . . ?
C25 C26 C29 122.38(13) . . ?
N1 C7 C6 117.77(13) . . ?
C8 C7 N1 121.39(13) . . ?
C8 C7 C6 120.80(14) . . ?
N2 C27 C26 117.82(12) . . ?
N2 C27 C28 121.42(13) . . ?
C28 C27 C26 120.76(14) . . ?
C28 C23 C24 119.99(13) . . ?
C28 C23 C22 117.91(13) . . ?
C24 C23 C22 122.10(14) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 C27 119.94(13) . . ?
C23 C28 H28 120.0 . . ?
C40 C35 C30 120.67(13) . . ?
C36 C35 C30 120.73(13) . . ?
C36 C35 C40 118.56(13) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.20(13) . . ?
C4 C5 H5 119.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.93(14) . . ?
C5 C4 H4 120.0 . . ?
O1 C2 C3 120.27(14) . . ?
O1 C2 C1 120.78(13) . . ?
C3 C2 C1 118.95(13) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C15 120.72(14) . . ?
C13 C14 C6 121.68(13) . . ?
C13 C14 H14 119.2 . . ?
C6 C14 H14 119.2 . . ?
C9 C10 H10 125.6 . . ?
C9 C10 C11 108.74(14) . . ?
C11 C10 H10 125.6 . . ?
N1 C9 H9 126.1 . . ?
C10 C9 N1 107.87(12) . . ?
C10 C9 H9 126.1 . . ?
C26 C25 H25 119.4 . . ?
C24 C25 C26 121.10(13) . . ?
C24 C25 H25 119.4 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.20(14) . . ?
C25 C24 H24 119.9 . . ?
C30 C29 C26 121.63(13) . . ?
C30 C29 H29 119.2 . . ?
C26 C29 H29 119.2 . . ?
C20 C15 C13 122.19(13) . . ?
C20 C15 C16 118.59(13) . . ?
C16 C15 C13 119.20(13) . . ?
N2 C34 H34 126.0 . . ?
C33 C34 N2 107.91(12) . . ?
C33 C34 H34 126.0 . . ?
C34 C33 H33 125.7 . . ?
C34 C33 C32 108.67(14) . . ?
C32 C33 H33 125.7 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.24(14) . . ?
C18 C19 H19 119.9 . . ?
C35 C40 H40 119.6 . . ?
C39 C40 C35 120.74(13) . . ?
C39 C40 H40 119.6 . . ?
C31 C32 C33 107.45(13) . . ?
C31 C32 H32 126.3 . . ?
C33 C32 H32 126.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C22 C23 120.32(14) . . ?
O2 C22 C21 121.02(13) . . ?
C23 C22 C21 118.65(13) . . ?
C12 C11 C10 107.48(13) . . ?
C12 C11 H11 126.3 . . ?
C10 C11 H11 126.3 . . ?
C40 C39 H39 119.9 . . ?
C40 C39 C38 120.20(14) . . ?
C38 C39 H39 119.9 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.51(14) . . ?
C17 C16 H16 119.7 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.48(14) . . ?
C37 C36 H36 119.8 . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.75(14) . . ?
C17 C18 H18 120.1 . . ?
C36 C37 H37 119.8 . . ?
C38 C37 C36 120.38(14) . . ?
C38 C37 H37 119.8 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.19(14) . . ?
C18 C17 H17 119.9 . . ?
C39 C38 H38 120.2 . . ?
C37 C38 C39 119.62(13) . . ?
C37 C38 H38 120.2 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C22 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
N1 C12 C11 C10 0.14(16) . . . . ?
N2 C31 C32 C33 0.01(16) . . . . ?
N2 C27 C28 C23 -177.31(13) . . . . ?
N2 C34 C33 C32 -0.24(17) . . . . ?
C30 C31 C32 C33 -176.48(15) . . . . ?
C30 C35 C40 C39 -176.57(13) . . . . ?
C30 C35 C36 C37 176.89(14) . . . . ?
C31 N2 C27 C26 1.6(2) . . . . ?
C31 N2 C27 C28 -179.35(12) . . . . ?
C31 N2 C34 C33 0.25(16) . . . . ?
C31 C30 C35 C40 -47.68(19) . . . . ?
C31 C30 C35 C36 134.48(15) . . . . ?
C31 C30 C29 C26 2.0(2) . . . . ?
C8 C3 C4 C5 -0.9(2) . . . . ?
C8 C3 C2 O1 10.6(2) . . . . ?
C8 C3 C2 C1 -169.20(13) . . . . ?
C13 C12 C11 C10 -173.88(16) . . . . ?
C13 C15 C16 C17 -178.79(13) . . . . ?
C3 C8 C7 N1 -175.73(13) . . . . ?
C3 C8 C7 C6 1.9(2) . . . . ?
C6 C5 C4 C3 1.9(2) . . . . ?
C12 N1 C7 C8 178.92(12) . . . . ?
C12 N1 C7 C6 1.2(2) . . . . ?
C12 N1 C9 C10 0.37(16) . . . . ?
C12 C13 C14 C6 -0.3(2) . . . . ?
C12 C13 C15 C20 -45.56(19) . . . . ?
C12 C13 C15 C16 132.77(15) . . . . ?
C26 C27 C28 C23 1.7(2) . . . . ?
C26 C25 C24 C23 1.4(2) . . . . ?
C7 N1 C12 C13 0.4(2) . . . . ?
C7 N1 C12 C11 -174.65(13) . . . . ?
C7 N1 C9 C10 174.33(14) . . . . ?
C7 C8 C3 C4 -0.9(2) . . . . ?
C7 C8 C3 C2 178.20(12) . . . . ?
C7 C6 C5 C4 -0.9(2) . . . . ?
C7 C6 C14 C13 2.0(2) . . . . ?
C27 N2 C31 C30 1.3(2) . . . . ?
C27 N2 C31 C32 -175.84(13) . . . . ?
C27 N2 C34 C33 175.60(14) . . . . ?
C27 C26 C25 C24 -0.5(2) . . . . ?
C27 C26 C29 C30 0.8(2) . . . . ?
C28 C23 C24 C25 -0.7(2) . . . . ?
C28 C23 C22 O2 9.7(2) . . . . ?
C28 C23 C22 C21 -169.76(13) . . . . ?
C35 C30 C31 N2 176.50(12) . . . . ?
C35 C30 C31 C32 -7.3(2) . . . . ?
C35 C30 C29 C26 -177.52(12) . . . . ?
C35 C40 C39 C38 -0.3(2) . . . . ?
C35 C36 C37 C38 -0.3(2) . . . . ?
C5 C6 C7 N1 176.72(13) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C5 C6 C14 C13 -177.06(14) . . . . ?
C4 C3 C2 O1 -170.32(14) . . . . ?
C4 C3 C2 C1 9.9(2) . . . . ?
C2 C3 C4 C5 179.94(13) . . . . ?
C20 C15 C16 C17 -0.4(2) . . . . ?
C20 C19 C18 C17 -0.2(2) . . . . ?
C14 C13 C12 N1 -0.9(2) . . . . ?
C14 C13 C12 C11 172.58(16) . . . . ?
C14 C13 C15 C20 138.84(16) . . . . ?
C14 C13 C15 C16 -42.8(2) . . . . ?
C14 C6 C7 N1 -2.3(2) . . . . ?
C14 C6 C7 C8 179.91(12) . . . . ?
C14 C6 C5 C4 178.15(13) . . . . ?
C9 N1 C12 C13 174.78(13) . . . . ?
C9 N1 C12 C11 -0.31(16) . . . . ?
C9 N1 C7 C8 5.7(2) . . . . ?
C9 N1 C7 C6 -172.01(14) . . . . ?
C9 C10 C11 C12 0.09(18) . . . . ?
C25 C26 C27 N2 177.99(12) . . . . ?
C25 C26 C27 C28 -1.1(2) . . . . ?
C25 C26 C29 C30 -179.80(14) . . . . ?
C24 C23 C28 C27 -0.8(2) . . . . ?
C24 C23 C22 O2 -170.84(15) . . . . ?
C24 C23 C22 C21 9.7(2) . . . . ?
C29 C30 C31 N2 -3.1(2) . . . . ?
C29 C30 C31 C32 173.10(16) . . . . ?
C29 C30 C35 C40 131.87(16) . . . . ?
C29 C30 C35 C36 -46.0(2) . . . . ?
C29 C26 C27 N2 -2.6(2) . . . . ?
C29 C26 C27 C28 178.30(12) . . . . ?
C29 C26 C25 C24 -179.84(13) . . . . ?
C15 C13 C12 N1 -176.60(11) . . . . ?
C15 C13 C12 C11 -3.1(2) . . . . ?
C15 C13 C14 C6 175.28(12) . . . . ?
C15 C20 C19 C18 -0.4(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C34 N2 C31 C30 176.94(13) . . . . ?
C34 N2 C31 C32 -0.16(16) . . . . ?
C34 N2 C27 C26 -173.21(13) . . . . ?
C34 N2 C27 C28 5.9(2) . . . . ?
C34 C33 C32 C31 0.14(18) . . . . ?
C19 C20 C15 C13 178.99(13) . . . . ?
C19 C20 C15 C16 0.7(2) . . . . ?
C19 C18 C17 C16 0.5(2) . . . . ?
C40 C35 C36 C37 -1.0(2) . . . . ?
C40 C39 C38 C37 -1.0(2) . . . . ?
C22 C23 C28 C27 178.68(12) . . . . ?
C22 C23 C24 C25 179.79(13) . . . . ?
C11 C10 C9 N1 -0.28(17) . . . . ?
C36 C35 C40 C39 1.3(2) . . . . ?
C36 C37 C38 C39 1.3(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.842
_oxdiff_exptl_absorpt_empirical_full_min 0.508
####################################################################### 
# 
# 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_p005
_database_code_depnum_ccdc_archive 'CCDC 1481744'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-06-14 downloaded from the CCDC.
;
_audit_creation_date             2016-01-25
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Cl N O'
_chemical_formula_sum            'C20 H14 Cl N O'
_chemical_formula_weight         319.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H14 Cl N O'
_chemical_oxdiff_usercomment     'Das_Koenig_AD P125'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.4245(3)
_cell_length_b                   7.25848(14)
_cell_length_c                   13.1153(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.390(2)
_cell_angle_gamma                90
_cell_volume                     1483.72(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3482
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.2070
_cell_measurement_theta_min      5.6670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41h (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -3 4 0.0624
1 4 5 0.0719
0 -3 -5 0.0620
-1 4 -5 0.0716
1 -4 5 0.0716
5 -4 -4 0.0546
7 3 -2 0.0348
-1 3 7 0.0676
9 0 3 0.0100
-9 1 -1 0.0229

_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.051
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.0002 -3.0005 4.0040 -0.2146 -0.8787 0.3096
1.0045 3.9994 4.9995 0.1455 0.7205 0.7819
-0.0040 -2.9994 -4.9999 -0.1159 -0.4946 -0.7281
-1.0019 4.0011 -4.9966 -0.6462 0.8163 -0.2617
1.0019 -4.0011 4.9966 0.6462 -0.8163 0.2617
4.9974 -3.9998 -4.0048 0.4683 -0.5337 -0.7425
7.0014 3.0002 -2.0044 0.3361 0.8460 -0.0964
-0.9950 2.9991 7.0004 0.1452 0.4280 0.9525
9.0038 -0.0009 2.9917 1.0118 0.2556 0.2190
-9.0023 1.0006 -0.9918 -0.9530 -0.0962 0.0592

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6017
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.307
_diffrn_reflns_theta_min         5.677
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  35.00   1.00    3.00    --  -40.71  37.00-150.00  102
  2  ω      2.00  98.00   1.00    3.00    --   40.71-125.00   0.00   96
  3  ω     32.00  77.00   1.00   11.00    --  106.98 -45.00 -90.00   45
  4  ω     23.00 109.00   1.00   11.00    --  106.98 -94.00 -60.00   86
  5  ω     77.00 158.00   1.00   11.00    --  106.98  61.00   0.00   81
  6  ω     32.00 121.00   1.00   11.00    --  106.98-125.00-120.00   89
  7  ω     18.00 158.00   1.00   11.00    --  106.98   0.00   0.00  140
  8  ω     11.00  36.00   1.00    3.00    --   40.71  57.00  90.00   25
  9  ω     11.00 115.00   1.00    3.00    --   40.71  57.00-150.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0922111000
_diffrn_orient_matrix_UB_12      -0.0626352000
_diffrn_orient_matrix_UB_13      0.0606807000
_diffrn_orient_matrix_UB_21      0.0338413000
_diffrn_orient_matrix_UB_22      0.1920885000
_diffrn_orient_matrix_UB_23      -0.0163446000
_diffrn_orient_matrix_UB_31      -0.0110977000
_diffrn_orient_matrix_UB_32      0.0649938000
_diffrn_orient_matrix_UB_33      0.1066358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2544
_reflns_number_total             2870
_reflns_odcompleteness_completeness 99.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.41h (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41h (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41h (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.056
_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)+(0.0454P)²+0.3342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0893
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C7(H7), C4(H4), C10(H10), C19(H19), C11(H11), C14(H14), C18(H18),
 C17(H17), C13(H13), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.03385(2) 0.68932(6) 0.91452(3) 0.02748(12) Uani 1 1 d . . . . .
O1 O 0.40485(7) 0.59942(18) 0.01726(8) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.69413(7) 0.54491(17) 0.30497(9) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.82024(9) 0.6087(2) 0.60097(11) 0.0195(3) Uani 1 1 d . . . . .
C16 C 0.83576(9) 0.4950(2) 0.37517(12) 0.0203(3) Uani 1 1 d . . . . .
H16 H 0.8911 0.4842 0.4227 0.024 Uiso 1 1 calc R . . . .
C15 C 0.76385(9) 0.5479(2) 0.40106(11) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.59425(9) 0.6143(2) 0.40021(11) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.66519(9) 0.6226(2) 0.49809(11) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.6546 0.6493 0.5621 0.024 Uiso 1 1 calc R . . . .
C4 C 0.54196(9) 0.5781(2) 0.20533(11) 0.0187(3) Uani 1 1 d . . . . .
H4 H 0.5528 0.5606 0.1406 0.022 Uiso 1 1 calc R . . . .
C3 C 0.45822(9) 0.6022(2) 0.20637(12) 0.0188(3) Uani 1 1 d . . . . .
C8 C 0.74750(9) 0.5926(2) 0.49974(11) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.60967(9) 0.5804(2) 0.30189(11) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.81211(9) 0.5420(2) 0.69706(12) 0.0209(3) Uani 1 1 d . . . . .
H10 H 0.7622 0.4808 0.6962 0.025 Uiso 1 1 calc R . . . .
C19 C 0.50927(9) 0.6424(2) 0.39856(12) 0.0203(3) Uani 1 1 d . . . . .
H19 H 0.4981 0.6683 0.4623 0.024 Uiso 1 1 calc R . . . .
C12 C 0.95156(9) 0.6552(2) 0.79364(11) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.38797(9) 0.5932(2) 0.10075(12) 0.0204(3) Uani 1 1 d . . . . .
C11 C 0.87726(9) 0.5655(2) 0.79400(12) 0.0214(3) Uani 1 1 d . . . . .
H11 H 0.8711 0.5218 0.8578 0.026 Uiso 1 1 calc R . . . .
C14 C 0.89657(10) 0.6962(2) 0.60362(12) 0.0220(3) Uani 1 1 d . . . . .
H14 H 0.9033 0.7397 0.5401 0.026 Uiso 1 1 calc R . . . .
C18 C 0.72350(9) 0.4916(2) 0.22207(11) 0.0205(3) Uani 1 1 d . . . . .
H18 H 0.6904 0.4789 0.1504 0.025 Uiso 1 1 calc R . . . .
C17 C 0.81016(9) 0.4606(2) 0.26383(12) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.8459 0.4231 0.2251 0.026 Uiso 1 1 calc R . . . .
C13 C 0.96246(9) 0.7194(2) 0.69958(13) 0.0230(3) Uani 1 1 d . . . . .
H13 H 1.0132 0.7773 0.7006 0.028 Uiso 1 1 calc R . . . .
C20 C 0.44212(9) 0.6323(2) 0.30384(12) 0.0200(3) Uani 1 1 d . . . . .
H20 H 0.3860 0.6454 0.3046 0.024 Uiso 1 1 calc R . . . .
C1 C 0.29664(9) 0.5729(2) 0.10084(12) 0.0242(3) Uani 1 1 d . . . . .
H1A H 0.2591 0.5637 0.0282 0.036 Uiso 1 1 calc GR . . . .
H1B H 0.2810 0.6785 0.1347 0.036 Uiso 1 1 calc GR . . . .
H1C H 0.2916 0.4637 0.1397 0.036 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
Cl1 C12 1.7463(14) . ?
O1 C2 1.2122(19) . ?
N1 C15 1.4104(18) . ?
N1 C5 1.3989(18) . ?
N1 C18 1.3768(18) . ?
C9 C8 1.4842(19) . ?
C9 C10 1.395(2) . ?
C9 C14 1.396(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.382(2) . ?
C16 C17 1.409(2) . ?
C15 C8 1.439(2) . ?
C6 C7 1.437(2) . ?
C6 C5 1.412(2) . ?
C6 C19 1.404(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.3908(19) . ?
C4 C5 1.397(2) . ?
C3 C2 1.499(2) . ?
C3 C20 1.402(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(2) . ?
C12 C11 1.384(2) . ?
C12 C13 1.382(2) . ?
C2 C1 1.5076(19) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.387(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.373(2) . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
C20 H20 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C5 N1 C15 122.75(12) . . ?
C18 N1 C15 108.79(12) . . ?
C18 N1 C5 128.33(12) . . ?
C10 C9 C8 120.10(13) . . ?
C10 C9 C14 118.45(13) . . ?
C14 C9 C8 121.40(13) . . ?
C15 C16 H16 126.1 . . ?
C15 C16 C17 107.77(13) . . ?
C17 C16 H16 126.1 . . ?
N1 C15 C8 118.55(12) . . ?
C16 C15 N1 106.97(12) . . ?
C16 C15 C8 134.40(13) . . ?
C5 C6 C7 119.65(13) . . ?
C19 C6 C7 121.97(13) . . ?
C19 C6 C5 118.37(13) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.87(13) . . ?
C8 C7 H7 119.1 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.77(13) . . ?
C5 C4 H4 120.1 . . ?
C4 C3 C2 117.44(13) . . ?
C4 C3 C20 120.01(13) . . ?
C20 C3 C2 122.55(13) . . ?
C15 C8 C9 119.75(13) . . ?
C7 C8 C9 121.08(13) . . ?
C7 C8 C15 119.16(13) . . ?
N1 C5 C6 117.88(12) . . ?
C4 C5 N1 121.50(13) . . ?
C4 C5 C6 120.60(13) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.23(14) . . ?
C11 C10 H10 119.4 . . ?
C6 C19 H19 119.5 . . ?
C20 C19 C6 120.99(13) . . ?
C20 C19 H19 119.5 . . ?
C11 C12 Cl1 119.62(12) . . ?
C13 C12 Cl1 118.77(11) . . ?
C13 C12 C11 121.61(13) . . ?
O1 C2 C3 120.31(13) . . ?
O1 C2 C1 121.03(13) . . ?
C3 C2 C1 118.65(13) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.65(14) . . ?
C12 C11 H11 120.7 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.00(14) . . ?
C13 C14 H14 119.5 . . ?
N1 C18 H18 126.0 . . ?
C17 C18 N1 107.97(12) . . ?
C17 C18 H18 126.0 . . ?
C16 C17 H17 125.8 . . ?
C18 C17 C16 108.50(13) . . ?
C18 C17 H17 125.8 . . ?
C12 C13 C14 119.03(14) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C3 C20 H20 119.9 . . ?
C19 C20 C3 120.17(13) . . ?
C19 C20 H20 119.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
Cl1 C12 C11 C10 179.13(12) . . . . ?
Cl1 C12 C13 C14 -178.61(12) . . . . ?
N1 C15 C8 C9 -176.09(13) . . . . ?
N1 C15 C8 C7 2.8(2) . . . . ?
N1 C18 C17 C16 0.00(18) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C9 C14 C13 C12 -0.4(2) . . . . ?
C16 C15 C8 C9 7.7(3) . . . . ?
C16 C15 C8 C7 -173.44(17) . . . . ?
C15 N1 C5 C6 -2.2(2) . . . . ?
C15 N1 C5 C4 179.39(13) . . . . ?
C15 N1 C18 C17 0.13(17) . . . . ?
C15 C16 C17 C18 -0.14(18) . . . . ?
C6 C7 C8 C9 177.71(13) . . . . ?
C6 C7 C8 C15 -1.2(2) . . . . ?
C6 C19 C20 C3 -3.1(2) . . . . ?
C7 C6 C5 N1 3.8(2) . . . . ?
C7 C6 C5 C4 -177.75(14) . . . . ?
C7 C6 C19 C20 -179.45(14) . . . . ?
C4 C3 C2 O1 -13.4(2) . . . . ?
C4 C3 C2 C1 165.50(14) . . . . ?
C4 C3 C20 C19 1.6(2) . . . . ?
C3 C4 C5 N1 175.83(13) . . . . ?
C3 C4 C5 C6 -2.6(2) . . . . ?
C8 C9 C10 C11 -175.98(14) . . . . ?
C8 C9 C14 C13 176.48(14) . . . . ?
C5 N1 C15 C16 176.07(13) . . . . ?
C5 N1 C15 C8 -1.1(2) . . . . ?
C5 N1 C18 C17 -175.88(14) . . . . ?
C5 C6 C7 C8 -2.2(2) . . . . ?
C5 C6 C19 C20 1.8(2) . . . . ?
C5 C4 C3 C2 -178.32(13) . . . . ?
C5 C4 C3 C20 1.2(2) . . . . ?
C10 C9 C8 C15 -140.97(15) . . . . ?
C10 C9 C8 C7 40.1(2) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C19 C6 C7 C8 179.02(14) . . . . ?
C19 C6 C5 N1 -177.37(13) . . . . ?
C19 C6 C5 C4 1.1(2) . . . . ?
C2 C3 C20 C19 -178.89(14) . . . . ?
C11 C12 C13 C14 1.2(2) . . . . ?
C14 C9 C8 C15 41.6(2) . . . . ?
C14 C9 C8 C7 -137.29(16) . . . . ?
C14 C9 C10 C11 1.5(2) . . . . ?
C18 N1 C15 C16 -0.22(17) . . . . ?
C18 N1 C15 C8 -177.42(13) . . . . ?
C18 N1 C5 C6 173.34(14) . . . . ?
C18 N1 C5 C4 -5.1(2) . . . . ?
C17 C16 C15 N1 0.22(17) . . . . ?
C17 C16 C15 C8 176.78(17) . . . . ?
C13 C12 C11 C10 -0.7(2) . . . . ?
C20 C3 C2 O1 167.05(15) . . . . ?
C20 C3 C2 C1 -14.0(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-21
_olex2_date_sample_submission    2016-01-14
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_submission_original_sample_id 'AD P 125'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.725
