# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_hnu_m405_1
_database_code_depnum_ccdc_archive 'CCDC 1056410'
_audit_update_record             
;
2015-03-27 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_audit_creation_date             2014-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H14 Cl2 N2 O'
_chemical_formula_sum            'C23 H14 Cl2 N2 O'
_chemical_formula_weight         405.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.9936(3)
_cell_length_b                   20.9137(5)
_cell_length_c                   10.6975(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.585(4)
_cell_angle_gamma                90.00
_cell_volume                     1857.79(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7377
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.1290
_cell_measurement_theta_min      5.3150
_exptl_absorpt_coefficient_mu    3.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16358
_diffrn_reflns_theta_full        70.08
_diffrn_reflns_theta_max         70.08
_diffrn_reflns_theta_min         4.23
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.6525
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1801817000
_diffrn_orient_matrix_UB_12      0.0172607000
_diffrn_orient_matrix_UB_13      0.0509047000
_diffrn_orient_matrix_UB_21      -0.0018264000
_diffrn_orient_matrix_UB_22      -0.0125444000
_diffrn_orient_matrix_UB_23      -0.1425004000
_diffrn_orient_matrix_UB_31      -0.0445519000
_diffrn_orient_matrix_UB_32      0.0704534000
_diffrn_orient_matrix_UB_33      -0.0379287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3092
_reflns_number_total             3521
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0434P)²+2.0432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1029
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C12(H12), C14(H14), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.24031(7) 0.26286(3) 0.96111(6) 0.03402(16) Uani 1 d . . .
Cl2 Cl 1.14724(8) 0.72117(3) 0.37707(6) 0.03522(16) Uani 1 d . . .
O1 O 1.15368(17) 0.50987(7) 0.78516(15) 0.0256(3) Uani 1 d . . .
C2 C 0.4108(3) 0.55285(10) 0.6507(2) 0.0247(4) Uani 1 d . . .
H2 H 0.3035 0.5543 0.6408 0.030 Uiso 1 calc . . R
N3 N 0.8968(2) 0.54941(8) 0.69179(18) 0.0227(4) Uani 1 d . . .
C4 C 1.0134(2) 0.50798(10) 0.7758(2) 0.0210(4) Uani 1 d . . .
N5 N 0.7769(2) 0.40484(9) 0.89601(18) 0.0249(4) Uani 1 d . . .
C6 C 0.6746(3) 0.50293(10) 0.7431(2) 0.0231(4) Uani 1 d . . .
C7 C 0.9533(2) 0.46117(10) 0.8453(2) 0.0211(4) Uani 1 d . . .
C8 C 1.0674(3) 0.67230(10) 0.4686(2) 0.0238(4) Uani 1 d . . .
C9 C 1.0563(3) 0.64171(10) 0.6791(2) 0.0233(4) Uani 1 d . . .
H9 H 1.0863 0.6477 0.7717 0.028 Uiso 1 calc . . R
C10 C 0.4719(3) 0.59824(11) 0.5877(2) 0.0266(5) Uani 1 d . . .
H10 H 0.4040 0.6300 0.5352 0.032 Uiso 1 calc . . R
C11 C 0.7341(2) 0.54967(10) 0.6787(2) 0.0228(4) Uani 1 d . . .
C12 C 1.1171(3) 0.68153(10) 0.6068(2) 0.0228(4) Uani 1 d . . .
H12 H 1.1898 0.7138 0.6502 0.027 Uiso 1 calc . . R
C13 C 0.6345(3) 0.37576(10) 0.9036(2) 0.0250(4) Uani 1 d . . .
C14 C 0.4730(3) 0.35342(10) 1.0327(2) 0.0251(4) Uani 1 d . . .
H14 H 0.4467 0.3609 1.1074 0.030 Uiso 1 calc . . R
C15 C 0.3907(3) 0.30771(10) 0.9376(2) 0.0245(4) Uani 1 d . . .
C16 C 0.9033(3) 0.58414(11) 0.4758(2) 0.0269(5) Uani 1 d . . .
H16 H 0.8331 0.5511 0.4328 0.032 Uiso 1 calc . . R
C17 C 1.0392(3) 0.41142(10) 0.9319(2) 0.0247(4) Uani 1 d . . .
H17 H 1.1492 0.4035 0.9627 0.030 Uiso 1 calc . . R
C18 C 0.9263(3) 0.37712(10) 0.9613(2) 0.0263(5) Uani 1 d . . .
H18 H 0.9471 0.3411 1.0163 0.032 Uiso 1 calc . . R
C19 C 0.9511(3) 0.59315(10) 0.6139(2) 0.0223(4) Uani 1 d . . .
C20 C 0.5120(3) 0.50568(10) 0.7282(2) 0.0242(4) Uani 1 d . . .
H20 H 0.4724 0.4754 0.7711 0.029 Uiso 1 calc . . R
C21 C 0.9606(3) 0.62458(11) 0.4020(2) 0.0271(5) Uani 1 d . . .
H21 H 0.9274 0.6196 0.3088 0.033 Uiso 1 calc . . R
C22 C 0.7920(3) 0.45690(10) 0.8240(2) 0.0218(4) Uani 1 d . . .
C23 C 0.5957(3) 0.38805(10) 1.0150(2) 0.0254(4) Uani 1 d . . .
H23 H 0.6513 0.4192 1.0775 0.030 Uiso 1 calc . . R
C24 C 0.6304(3) 0.59717(11) 0.6014(2) 0.0273(5) Uani 1 d . . .
H24 H 0.6686 0.6282 0.5590 0.033 Uiso 1 calc . . R
C25 C 0.5481(3) 0.33110(11) 0.8069(2) 0.0309(5) Uani 1 d . . .
H25 H 0.5725 0.3242 0.7310 0.037 Uiso 1 calc . . R
C26 C 0.4250(3) 0.29672(11) 0.8238(2) 0.0307(5) Uani 1 d . . .
H26 H 0.3663 0.2667 0.7596 0.037 Uiso 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 C15 1.742(2) . ?
Cl2 C8 1.749(2) . ?
O1 C4 1.227(2) . ?
C2 H2 0.9300 . ?
C2 C10 1.393(3) . ?
C2 C20 1.382(3) . ?
N3 C4 1.391(3) . ?
N3 C11 1.415(3) . ?
N3 C19 1.443(3) . ?
C4 C7 1.453(3) . ?
N5 C13 1.447(3) . ?
N5 C18 1.382(3) . ?
N5 C22 1.370(3) . ?
C6 C11 1.414(3) . ?
C6 C20 1.410(3) . ?
C6 C22 1.445(3) . ?
C7 C17 1.410(3) . ?
C7 C22 1.382(3) . ?
C8 C12 1.384(3) . ?
C8 C21 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C12 1.384(3) . ?
C9 C19 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C24 1.377(3) . ?
C11 C24 1.396(3) . ?
C12 H12 0.9300 . ?
C13 C23 1.389(3) . ?
C13 C25 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C14 C23 1.392(3) . ?
C15 C26 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C19 1.384(3) . ?
C16 C21 1.384(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(3) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.389(3) . ?
C26 H26 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
C10 C2 H2 120.5 . . ?
C20 C2 H2 120.5 . . ?
C20 C2 C10 119.0(2) . . ?
C4 N3 C11 124.12(17) . . ?
C4 N3 C19 115.43(17) . . ?
C11 N3 C19 120.45(18) . . ?
O1 C4 N3 121.94(19) . . ?
O1 C4 C7 123.56(19) . . ?
N3 C4 C7 114.44(17) . . ?
C18 N5 C13 120.31(18) . . ?
C22 N5 C13 130.27(19) . . ?
C22 N5 C18 109.28(18) . . ?
C11 C6 C22 115.20(19) . . ?
C20 C6 C11 119.13(19) . . ?
C20 C6 C22 125.63(19) . . ?
C17 C7 C4 128.01(19) . . ?
C22 C7 C4 122.16(19) . . ?
C22 C7 C17 109.62(18) . . ?
C12 C8 Cl2 118.88(17) . . ?
C21 C8 Cl2 119.20(17) . . ?
C21 C8 C12 121.89(19) . . ?
C12 C9 H9 119.9 . . ?
C19 C9 H9 119.9 . . ?
C19 C9 C12 120.12(19) . . ?
C2 C10 H10 119.3 . . ?
C24 C10 C2 121.5(2) . . ?
C24 C10 H10 119.3 . . ?
C6 C11 N3 121.28(19) . . ?
C24 C11 N3 119.45(19) . . ?
C24 C11 C6 119.27(19) . . ?
C8 C12 C9 118.5(2) . . ?
C8 C12 H12 120.7 . . ?
C9 C12 H12 120.7 . . ?
C23 C13 N5 119.31(19) . . ?
C25 C13 N5 119.70(19) . . ?
C25 C13 C23 120.7(2) . . ?
C15 C14 H14 120.4 . . ?
C15 C14 C23 119.18(19) . . ?
C23 C14 H14 120.4 . . ?
C14 C15 Cl1 119.44(17) . . ?
C26 C15 Cl1 118.99(17) . . ?
C26 C15 C14 121.6(2) . . ?
C19 C16 H16 120.2 . . ?
C19 C16 C21 119.6(2) . . ?
C21 C16 H16 120.2 . . ?
C7 C17 H17 127.2 . . ?
C18 C17 C7 105.63(19) . . ?
C18 C17 H17 127.2 . . ?
N5 C18 H18 125.5 . . ?
C17 C18 N5 109.00(19) . . ?
C17 C18 H18 125.5 . . ?
C9 C19 N3 119.56(19) . . ?
C9 C19 C16 120.73(19) . . ?
C16 C19 N3 119.64(19) . . ?
C2 C20 C6 120.8(2) . . ?
C2 C20 H20 119.6 . . ?
C6 C20 H20 119.6 . . ?
C8 C21 C16 119.0(2) . . ?
C8 C21 H21 120.5 . . ?
C16 C21 H21 120.5 . . ?
N5 C22 C6 131.15(19) . . ?
N5 C22 C7 106.46(18) . . ?
C7 C22 C6 122.35(19) . . ?
C13 C23 C14 119.6(2) . . ?
C13 C23 H23 120.2 . . ?
C14 C23 H23 120.2 . . ?
C10 C24 C11 120.2(2) . . ?
C10 C24 H24 119.9 . . ?
C11 C24 H24 119.9 . . ?
C13 C25 H25 120.1 . . ?
C13 C25 C26 119.8(2) . . ?
C26 C25 H25 120.1 . . ?
C15 C26 C25 119.1(2) . . ?
C15 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?

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 C15 C26 C25 -178.11(18) . . . . ?
Cl2 C8 C12 C9 -178.52(16) . . . . ?
Cl2 C8 C21 C16 177.08(17) . . . . ?
O1 C4 C7 C17 -0.2(3) . . . . ?
O1 C4 C7 C22 -174.51(19) . . . . ?
C2 C10 C24 C11 0.6(3) . . . . ?
N3 C4 C7 C17 177.07(19) . . . . ?
N3 C4 C7 C22 2.7(3) . . . . ?
N3 C11 C24 C10 -179.9(2) . . . . ?
C4 N3 C11 C6 -5.6(3) . . . . ?
C4 N3 C11 C24 173.95(19) . . . . ?
C4 N3 C19 C9 -69.1(2) . . . . ?
C4 N3 C19 C16 107.9(2) . . . . ?
C4 C7 C17 C18 -174.5(2) . . . . ?
C4 C7 C22 N5 174.99(18) . . . . ?
C4 C7 C22 C6 -7.0(3) . . . . ?
N5 C13 C23 C14 -170.9(2) . . . . ?
N5 C13 C25 C26 171.2(2) . . . . ?
C6 C11 C24 C10 -0.3(3) . . . . ?
C7 C17 C18 N5 -0.3(2) . . . . ?
C10 C2 C20 C6 -0.4(3) . . . . ?
C11 N3 C4 O1 -179.22(19) . . . . ?
C11 N3 C4 C7 3.5(3) . . . . ?
C11 N3 C19 C9 111.8(2) . . . . ?
C11 N3 C19 C16 -71.2(3) . . . . ?
C11 C6 C20 C2 0.7(3) . . . . ?
C11 C6 C22 N5 -177.8(2) . . . . ?
C11 C6 C22 C7 4.8(3) . . . . ?
C12 C8 C21 C16 -1.0(3) . . . . ?
C12 C9 C19 N3 175.98(19) . . . . ?
C12 C9 C19 C16 -0.9(3) . . . . ?
C13 N5 C18 C17 176.35(18) . . . . ?
C13 N5 C22 C6 6.6(4) . . . . ?
C13 N5 C22 C7 -175.6(2) . . . . ?
C13 C25 C26 C15 -0.1(4) . . . . ?
C14 C15 C26 C25 1.9(4) . . . . ?
C15 C14 C23 C13 -0.7(3) . . . . ?
C17 C7 C22 N5 -0.3(2) . . . . ?
C17 C7 C22 C6 177.71(18) . . . . ?
C18 N5 C13 C23 83.4(3) . . . . ?
C18 N5 C13 C25 -90.1(3) . . . . ?
C18 N5 C22 C6 -177.7(2) . . . . ?
C18 N5 C22 C7 0.1(2) . . . . ?
C19 N3 C4 O1 1.8(3) . . . . ?
C19 N3 C4 C7 -175.52(17) . . . . ?
C19 N3 C11 C6 173.35(18) . . . . ?
C19 N3 C11 C24 -7.1(3) . . . . ?
C19 C9 C12 C8 1.4(3) . . . . ?
C19 C16 C21 C8 1.5(3) . . . . ?
C20 C2 C10 C24 -0.2(3) . . . . ?
C20 C6 C11 N3 179.26(18) . . . . ?
C20 C6 C11 C24 -0.3(3) . . . . ?
C20 C6 C22 N5 4.4(4) . . . . ?
C20 C6 C22 C7 -173.0(2) . . . . ?
C21 C8 C12 C9 -0.4(3) . . . . ?
C21 C16 C19 N3 -177.44(19) . . . . ?
C21 C16 C19 C9 -0.5(3) . . . . ?
C22 N5 C13 C23 -101.4(3) . . . . ?
C22 N5 C13 C25 85.1(3) . . . . ?
C22 N5 C18 C17 0.2(2) . . . . ?
C22 C6 C11 N3 1.3(3) . . . . ?
C22 C6 C11 C24 -178.26(19) . . . . ?
C22 C6 C20 C2 178.4(2) . . . . ?
C22 C7 C17 C18 0.4(2) . . . . ?
C23 C13 C25 C26 -2.2(4) . . . . ?
C23 C14 C15 Cl1 178.49(17) . . . . ?
C23 C14 C15 C26 -1.6(3) . . . . ?
C25 C13 C23 C14 2.6(3) . . . . ?

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

data_20150105a
_database_code_depnum_ccdc_archive 'CCDC 1056498'
_audit_update_record             
;
2015-03-27 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_audit_creation_date             2015-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H14 Cl2 N2 O2'
_chemical_formula_sum            'C24 H14 Cl2 N2 O2'
_chemical_formula_weight         433.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Cl2
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.3775(5)
_cell_length_b                   12.1686(10)
_cell_length_c                   13.4121(8)
_cell_angle_alpha                80.819(6)
_cell_angle_beta                 88.955(5)
_cell_angle_gamma                75.537(7)
_cell_volume                     994.69(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2552
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1740
_cell_measurement_theta_min      3.7960
_exptl_absorpt_coefficient_mu    3.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7140
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -69.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -67.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -67.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega   14.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   24.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   33.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega    7.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega  -13.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 10 omega    8.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 12 omega  125.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega   45.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 14 omega   59.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
 15 omega   42.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega   75.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega   82.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
 18 omega   89.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
 19 omega   77.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   65.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   44.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
 22 omega   39.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 23 omega   45.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 24 omega  101.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
 25 omega   58.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
 26 omega  103.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 27 omega  106.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega   71.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega  122.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 30 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 31 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 32 omega   35.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
 33 omega   26.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   60.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0673917000
_diffrn_orient_matrix_UB_12      0.1232802000
_diffrn_orient_matrix_UB_13      0.0245083000
_diffrn_orient_matrix_UB_21      0.2372413000
_diffrn_orient_matrix_UB_22      0.0078279000
_diffrn_orient_matrix_UB_23      -0.0084315000
_diffrn_orient_matrix_UB_31      -0.0379732000
_diffrn_orient_matrix_UB_32      0.0477990000
_diffrn_orient_matrix_UB_33      -0.1134609000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2754
_reflns_number_total             3554
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.1760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.59660(17) 0.58361(8) -0.43729(6) 0.0854(3) Uani 1 d . . .
Cl2 Cl 0.8312(2) 0.87537(10) 0.60420(6) 0.1015(4) Uani 1 d . . .
O1 O 1.0621(3) 0.81377(16) -0.15785(11) 0.0479(4) Uani 1 d . . .
O2 O 1.4529(3) 1.00946(17) 0.13582(15) 0.0600(5) Uani 1 d . . .
N1 N 0.8432(3) 0.72042(16) -0.06035(13) 0.0382(4) Uani 1 d . . .
N2 N 1.0515(3) 0.84506(17) 0.17778(14) 0.0399(4) Uani 1 d . . .
C1 C 0.7114(4) 0.6947(2) 0.21279(18) 0.0459(5) Uani 1 d . . .
H1 H 0.7456 0.7193 0.2712 0.055 Uiso 1 calc . . R
C2 C 0.5680(4) 0.6258(2) 0.2173(2) 0.0521(6) Uani 1 d . . .
H2 H 0.5082 0.6034 0.2786 0.062 Uiso 1 calc . . R
C3 C 0.5136(4) 0.5904(2) 0.1310(2) 0.0527(6) Uani 1 d . . .
H3 H 0.4154 0.5449 0.1342 0.063 Uiso 1 calc . . R
C4 C 0.6033(4) 0.6215(2) 0.0401(2) 0.0478(6) Uani 1 d . . .
H4 H 0.5659 0.5964 -0.0175 0.057 Uiso 1 calc . . R
C5 C 0.7504(3) 0.69074(18) 0.03324(17) 0.0381(5) Uani 1 d . . .
C6 C 0.8065(3) 0.72821(18) 0.12153(17) 0.0376(5) Uani 1 d . . .
C7 C 0.9627(3) 0.79674(18) 0.10902(16) 0.0361(5) Uani 1 d . . .
C8 C 1.0552(3) 0.82206(18) 0.01661(16) 0.0349(5) Uani 1 d . . .
C9 C 0.9933(3) 0.78742(19) -0.07439(16) 0.0372(5) Uani 1 d . . .
C10 C 1.2041(3) 0.88726(18) 0.02880(16) 0.0368(5) Uani 1 d . . .
H10 H 1.2886 0.9158 -0.0211 0.044 Uiso 1 calc . . R
C11 C 1.2006(4) 0.90045(19) 0.12765(16) 0.0385(5) Uani 1 d . . .
C12 C 1.3268(4) 0.9597(2) 0.17868(18) 0.0465(6) Uani 1 d . . .
H12 H 1.3098 0.9595 0.2477 0.056 Uiso 1 calc . . R
C13 C 0.7783(4) 0.68441(19) -0.15005(17) 0.0395(5) Uani 1 d . . .
C14 C 0.5728(4) 0.7317(2) -0.19148(19) 0.0446(5) Uani 1 d . . .
H14 H 0.4747 0.7856 -0.1607 0.054 Uiso 1 calc . . R
C15 C 0.5126(4) 0.6991(2) -0.2786(2) 0.0516(6) Uani 1 d . . .
H15 H 0.3731 0.7287 -0.3058 0.062 Uiso 1 calc . . R
C16 C 0.6639(5) 0.6215(2) -0.3242(2) 0.0542(7) Uani 1 d . . .
C17 C 0.8678(5) 0.5730(2) -0.2836(2) 0.0577(7) Uani 1 d . . .
H17 H 0.9663 0.5199 -0.3151 0.069 Uiso 1 calc . . R
C18 C 0.9254(4) 0.6043(2) -0.1949(2) 0.0503(6) Uani 1 d . . .
H18 H 1.0626 0.5715 -0.1658 0.060 Uiso 1 calc . . R
C19 C 0.9934(4) 0.8514(2) 0.28135(16) 0.0408(5) Uani 1 d . . .
C20 C 0.8449(4) 0.9460(2) 0.30406(19) 0.0514(6) Uani 1 d . . .
H20 H 0.7800 1.0049 0.2527 0.062 Uiso 1 calc . . R
C21 C 0.7913(5) 0.9538(3) 0.4033(2) 0.0651(8) Uani 1 d . . .
H21 H 0.6898 1.0177 0.4192 0.078 Uiso 1 calc . . R
C22 C 0.8897(5) 0.8663(3) 0.47841(19) 0.0606(8) Uani 1 d . . .
C23 C 1.0345(6) 0.7706(3) 0.4562(2) 0.0789(10) Uani 1 d . . .
H23 H 1.0973 0.7111 0.5076 0.095 Uiso 1 calc . . R
C24 C 1.0871(5) 0.7628(3) 0.3565(2) 0.0716(9) Uani 1 d . . .
H24 H 1.1853 0.6979 0.3405 0.086 Uiso 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 C16 1.744(2) . ?
Cl2 C22 1.736(2) . ?
O1 C9 1.219(3) . ?
O2 C12 1.208(3) . ?
N1 C5 1.411(3) . ?
N1 C9 1.396(3) . ?
N1 C13 1.445(3) . ?
N2 C7 1.369(3) . ?
N2 C11 1.401(3) . ?
N2 C19 1.440(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(3) . ?
C5 C6 1.417(3) . ?
C6 C7 1.442(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.445(3) . ?
C8 C10 1.408(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.360(3) . ?
C11 C12 1.451(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(3) . ?
C13 C18 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(4) . ?
C16 C17 1.369(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(3) . ?
C19 C24 1.375(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(4) . ?
C22 C23 1.365(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(4) . ?
C24 H24 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
C5 N1 C13 120.00(18) . . ?
C9 N1 C5 124.15(18) . . ?
C9 N1 C13 115.81(18) . . ?
C7 N2 C11 108.06(18) . . ?
C7 N2 C19 128.32(19) . . ?
C11 N2 C19 123.34(19) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.1(2) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C6 120.95(19) . . ?
C4 C5 N1 119.9(2) . . ?
C4 C5 C6 119.1(2) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 125.6(2) . . ?
C5 C6 C7 115.88(19) . . ?
N2 C7 C6 130.6(2) . . ?
N2 C7 C8 107.53(19) . . ?
C8 C7 C6 121.8(2) . . ?
C7 C8 C9 122.5(2) . . ?
C7 C8 C10 108.63(19) . . ?
C10 C8 C9 128.8(2) . . ?
O1 C9 N1 121.2(2) . . ?
O1 C9 C8 124.2(2) . . ?
N1 C9 C8 114.57(18) . . ?
C8 C10 H10 126.6 . . ?
C11 C10 C8 106.73(19) . . ?
C11 C10 H10 126.6 . . ?
N2 C11 C12 122.7(2) . . ?
C10 C11 N2 109.06(19) . . ?
C10 C11 C12 128.3(2) . . ?
O2 C12 C11 123.2(2) . . ?
O2 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C14 C13 N1 120.2(2) . . ?
C18 C13 N1 119.2(2) . . ?
C18 C13 C14 120.5(2) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.6(2) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 Cl1 119.6(2) . . ?
C17 C16 Cl1 118.4(2) . . ?
C17 C16 C15 122.0(2) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.1(3) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 119.7(2) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 N2 119.5(2) . . ?
C20 C19 C24 120.5(2) . . ?
C24 C19 N2 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 Cl2 120.4(2) . . ?
C23 C22 Cl2 118.5(2) . . ?
C23 C22 C21 121.1(3) . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C19 C24 C23 119.7(3) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?

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 C16 C17 C18 178.6(2) . . . . ?
Cl2 C22 C23 C24 -178.6(3) . . . . ?
N1 C5 C6 C1 -179.1(2) . . . . ?
N1 C5 C6 C7 -0.3(3) . . . . ?
N1 C13 C14 C15 178.5(2) . . . . ?
N1 C13 C18 C17 -177.1(2) . . . . ?
N2 C7 C8 C9 -177.9(2) . . . . ?
N2 C7 C8 C10 0.0(3) . . . . ?
N2 C11 C12 O2 -178.7(2) . . . . ?
N2 C19 C20 C21 -178.7(2) . . . . ?
N2 C19 C24 C23 178.4(3) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C1 C6 C7 N2 -0.8(4) . . . . ?
C1 C6 C7 C8 177.3(2) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C1 C6 C7 -178.0(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 N1 179.0(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 178.5(2) . . . . ?
C5 N1 C9 O1 -177.3(2) . . . . ?
C5 N1 C9 C8 2.2(3) . . . . ?
C5 N1 C13 C14 69.2(3) . . . . ?
C5 N1 C13 C18 -112.2(3) . . . . ?
C5 C6 C7 N2 -179.5(2) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C6 C7 C8 C9 3.6(3) . . . . ?
C6 C7 C8 C10 -178.5(2) . . . . ?
C7 N2 C11 C10 0.2(3) . . . . ?
C7 N2 C11 C12 -179.2(2) . . . . ?
C7 N2 C19 C20 -92.6(3) . . . . ?
C7 N2 C19 C24 87.4(3) . . . . ?
C7 C8 C9 O1 175.6(2) . . . . ?
C7 C8 C9 N1 -3.8(3) . . . . ?
C7 C8 C10 C11 0.1(3) . . . . ?
C8 C10 C11 N2 -0.2(3) . . . . ?
C8 C10 C11 C12 179.2(2) . . . . ?
C9 N1 C5 C4 -179.1(2) . . . . ?
C9 N1 C5 C6 -0.2(3) . . . . ?
C9 N1 C13 C14 -108.7(2) . . . . ?
C9 N1 C13 C18 69.8(3) . . . . ?
C9 C8 C10 C11 177.9(2) . . . . ?
C10 C8 C9 O1 -1.8(4) . . . . ?
C10 C8 C9 N1 178.7(2) . . . . ?
C10 C11 C12 O2 2.0(4) . . . . ?
C11 N2 C7 C6 178.2(2) . . . . ?
C11 N2 C7 C8 -0.2(2) . . . . ?
C11 N2 C19 C20 80.5(3) . . . . ?
C11 N2 C19 C24 -99.5(3) . . . . ?
C13 N1 C5 C4 3.2(3) . . . . ?
C13 N1 C5 C6 -178.0(2) . . . . ?
C13 N1 C9 O1 0.6(3) . . . . ?
C13 N1 C9 C8 -179.95(19) . . . . ?
C13 C14 C15 C16 -2.0(4) . . . . ?
C14 C13 C18 C17 1.4(4) . . . . ?
C14 C15 C16 Cl1 -177.14(19) . . . . ?
C14 C15 C16 C17 2.6(4) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
C16 C17 C18 C13 -0.9(4) . . . . ?
C18 C13 C14 C15 0.0(4) . . . . ?
C19 N2 C7 C6 -7.9(4) . . . . ?
C19 N2 C7 C8 173.8(2) . . . . ?
C19 N2 C11 C10 -174.1(2) . . . . ?
C19 N2 C11 C12 6.5(3) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C20 C19 C24 C23 -1.6(5) . . . . ?
C20 C21 C22 Cl2 178.3(2) . . . . ?
C20 C21 C22 C23 -1.9(5) . . . . ?
C21 C22 C23 C24 1.6(5) . . . . ?
C22 C23 C24 C19 0.1(6) . . . . ?
C24 C19 C20 C21 1.3(4) . . . . ?

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

data_20150125
_database_code_depnum_ccdc_archive 'CCDC 1056576'
_audit_update_record             
;
2015-03-27 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_audit_creation_date             2015-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H14 Cl2 N2 O2'
_chemical_formula_sum            'C24 H14 Cl2 N2 O2'
_chemical_formula_weight         433.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Cl2
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.2005(5)
_cell_length_b                   13.556(3)
_cell_length_c                   15.6215(13)
_cell_angle_alpha                73.584(12)
_cell_angle_beta                 85.490(8)
_cell_angle_gamma                87.120(12)
_cell_volume                     1052.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1606
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      63.5940
_cell_measurement_theta_min      3.8330
_exptl_absorpt_coefficient_mu    2.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7415
_diffrn_reflns_theta_full        67.12
_diffrn_reflns_theta_max         67.12
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_temperature      291.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   16.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00   26.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00    9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega  -47.00  -14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega  -85.00   27.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   19.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
  7 omega -111.00  -86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000 -148.0000  -74.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   19.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -180.0000 68

#__ type_ start__ end____ width___ exp.time_
 10 omega  105.00  173.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
 11 omega   83.00  115.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega   60.00  128.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 68

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   96.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 14 omega   47.00  100.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   90.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00   98.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
 17 omega   63.00  101.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   98.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 56

#__ type_ start__ end____ width___ exp.time_
 19 omega   57.00   86.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 20 omega   80.00  108.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 21 omega   41.00   97.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
 22 omega   41.00   68.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   48.00   90.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 24 omega   58.00  106.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 25 omega   39.00  167.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  120.0000 128

#__ type_ start__ end____ width___ exp.time_
 26 omega  -26.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 27 omega -111.00  -21.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 28 omega -113.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
 29 omega -113.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 30 omega   35.00  125.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0028011000
_diffrn_orient_matrix_UB_12      0.1084442000
_diffrn_orient_matrix_UB_13      -0.0662925000
_diffrn_orient_matrix_UB_21      0.0003896000
_diffrn_orient_matrix_UB_22      0.0476079000
_diffrn_orient_matrix_UB_23      0.0786176000
_diffrn_orient_matrix_UB_31      0.2972171000
_diffrn_orient_matrix_UB_32      -0.0044780000
_diffrn_orient_matrix_UB_33      -0.0064595000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2071
_reflns_number_total             3744
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0022(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1001P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2294
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.4620(3) 0.66266(16) 0.68029(8) 0.1245(7) Uani 1 d . . .
Cl2 Cl 0.8757(4) 0.91300(15) -0.32879(11) 0.1416(8) Uani 1 d . . .
O1 O 0.1374(6) 0.5856(2) 0.32649(19) 0.0757(9) Uani 1 d . . .
O2 O -0.1582(6) 0.4767(3) 0.1210(2) 0.0879(10) Uani 1 d . . .
N1 N 0.4482(6) 0.7066(3) 0.2922(2) 0.0646(9) Uani 1 d . . .
N2 N 0.4274(7) 0.6975(3) 0.0311(2) 0.0660(9) Uani 1 d . . .
C1 C 0.2867(10) 0.7560(5) 0.4260(3) 0.103(2) Uani 1 d . . .
H1 H 0.1710 0.8024 0.3919 0.124 Uiso 1 calc . . R
C2 C 0.2899(11) 0.7455(6) 0.5163(4) 0.115(2) Uani 1 d . . .
H2 H 0.1769 0.7849 0.5432 0.139 Uiso 1 calc . . R
C3 C 0.4587(10) 0.6775(4) 0.5656(3) 0.0848(15) Uani 1 d . . .
C4 C 0.6283(10) 0.6200(4) 0.5279(3) 0.0876(15) Uani 1 d . . .
H4 H 0.7459 0.5748 0.5622 0.105 Uiso 1 calc . . R
C5 C 0.6232(9) 0.6300(4) 0.4371(3) 0.0760(13) Uani 1 d . . .
H5 H 0.7355 0.5902 0.4104 0.091 Uiso 1 calc . . R
C6 C 0.4528(8) 0.6985(4) 0.3869(3) 0.0675(11) Uani 1 d . . .
C7 C 0.8128(8) 0.8416(4) 0.0810(3) 0.0682(11) Uani 1 d . . .
H7 H 0.8250 0.8447 0.0206 0.082 Uiso 1 calc . . R
C8 C 0.9737(9) 0.9009(4) 0.1118(3) 0.0730(12) Uani 1 d . . .
H8 H 1.0936 0.9427 0.0725 0.088 Uiso 1 calc . . R
C9 C 0.9538(9) 0.8972(4) 0.2012(3) 0.0748(12) Uani 1 d . . .
H9 H 1.0598 0.9374 0.2220 0.090 Uiso 1 calc . . R
C10 C 0.7792(8) 0.8348(4) 0.2598(3) 0.0717(12) Uani 1 d . . .
H10 H 0.7672 0.8339 0.3197 0.086 Uiso 1 calc . . R
C11 C 0.6186(7) 0.7724(3) 0.2306(3) 0.0604(10) Uani 1 d . . .
C12 C 0.6330(8) 0.7775(3) 0.1388(3) 0.0613(10) Uani 1 d . . .
C13 C 0.4607(8) 0.7119(3) 0.1141(3) 0.0614(10) Uani 1 d . . .
C14 C 0.2956(7) 0.6476(3) 0.1755(3) 0.0603(10) Uani 1 d . . .
C15 C 0.2815(8) 0.6418(3) 0.2695(3) 0.0627(11) Uani 1 d . . .
C16 C 0.2480(9) 0.6237(4) 0.0428(3) 0.0729(12) Uani 1 d . . .
H16 H 0.1956 0.5988 -0.0025 0.088 Uiso 1 calc . . R
C17 C 0.1560(8) 0.5913(3) 0.1307(3) 0.0638(11) Uani 1 d . . .
C18 C -0.0456(9) 0.5192(4) 0.1648(3) 0.0758(13) Uani 1 d . . .
H18 H -0.0936 0.5038 0.2257 0.091 Uiso 1 calc . . R
C19 C 0.5400(8) 0.7503(4) -0.0552(3) 0.0660(11) Uani 1 d . . .
C20 C 0.4526(10) 0.8471(4) -0.0976(3) 0.0837(14) Uani 1 d . . .
H20 H 0.3229 0.8792 -0.0697 0.100 Uiso 1 calc . . R
C21 C 0.5567(10) 0.8979(4) -0.1824(3) 0.0900(15) Uani 1 d . . .
H21 H 0.4983 0.9639 -0.2117 0.108 Uiso 1 calc . . R
C22 C 0.7452(11) 0.8493(5) -0.2218(3) 0.0873(15) Uani 1 d . . .
C23 C 0.8316(10) 0.7525(5) -0.1802(3) 0.0932(16) Uani 1 d . . .
H23 H 0.9604 0.7205 -0.2085 0.112 Uiso 1 calc . . R
C24 C 0.7292(9) 0.7020(4) -0.0967(3) 0.0778(13) Uani 1 d . . .
H24 H 0.7870 0.6356 -0.0683 0.093 Uiso 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 C3 1.747(4) . ?
Cl2 C22 1.751(5) . ?
O1 C15 1.227(5) . ?
O2 C18 1.208(5) . ?
N1 C6 1.454(5) . ?
N1 C11 1.403(5) . ?
N1 C15 1.396(5) . ?
N2 C13 1.390(4) . ?
N2 C16 1.368(5) . ?
N2 C19 1.430(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(6) . ?
C1 C6 1.359(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.356(8) . ?
C3 C4 1.357(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(6) . ?
C7 C12 1.397(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.403(6) . ?
C11 C12 1.413(5) . ?
C12 C13 1.439(5) . ?
C13 C14 1.374(6) . ?
C14 C15 1.444(5) . ?
C14 C17 1.428(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(6) . ?
C17 C18 1.435(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(6) . ?
C19 C24 1.375(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.357(7) . ?
C22 C23 1.361(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.369(6) . ?
C24 H24 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
C11 N1 C6 119.3(3) . . ?
C15 N1 C6 116.4(4) . . ?
C15 N1 C11 124.1(3) . . ?
C13 N2 C19 129.6(4) . . ?
C16 N2 C13 108.0(4) . . ?
C16 N2 C19 122.4(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 119.9(5) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 Cl1 120.0(4) . . ?
C2 C3 C4 121.4(4) . . ?
C4 C3 Cl1 118.5(4) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(5) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 N1 120.8(4) . . ?
C1 C6 C5 120.0(4) . . ?
C5 C6 N1 119.2(4) . . ?
C8 C7 H7 119.3 . . ?
C8 C7 C12 121.4(4) . . ?
C12 C7 H7 119.3 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
N1 C11 C12 121.3(3) . . ?
C10 C11 N1 120.0(4) . . ?
C10 C11 C12 118.7(4) . . ?
C7 C12 C11 118.8(4) . . ?
C7 C12 C13 125.8(4) . . ?
C11 C12 C13 115.3(4) . . ?
N2 C13 C12 130.1(4) . . ?
C14 C13 N2 107.3(3) . . ?
C14 C13 C12 122.6(3) . . ?
C13 C14 C15 122.2(4) . . ?
C13 C14 C17 109.0(3) . . ?
C17 C14 C15 128.8(4) . . ?
O1 C15 N1 121.1(3) . . ?
O1 C15 C14 124.4(4) . . ?
N1 C15 C14 114.5(4) . . ?
N2 C16 H16 124.7 . . ?
N2 C16 C17 110.7(4) . . ?
C17 C16 H16 124.7 . . ?
C14 C17 C18 129.9(4) . . ?
C16 C17 C14 105.0(4) . . ?
C16 C17 C18 125.1(4) . . ?
O2 C18 C17 125.4(4) . . ?
O2 C18 H18 117.3 . . ?
C17 C18 H18 117.3 . . ?
C20 C19 N2 119.9(4) . . ?
C20 C19 C24 120.1(4) . . ?
C24 C19 N2 119.9(4) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.7(5) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 Cl2 118.8(5) . . ?
C21 C22 C23 121.4(5) . . ?
C23 C22 Cl2 119.8(4) . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.1(5) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 120.3 . . ?
C23 C24 C19 119.4(5) . . ?
C23 C24 H24 120.3 . . ?

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
Cl1 C3 C4 C5 178.8(4) . . . . ?
Cl2 C22 C23 C24 -179.6(4) . . . . ?
N1 C11 C12 C7 -177.7(4) . . . . ?
N1 C11 C12 C13 0.6(5) . . . . ?
N2 C13 C14 C15 179.3(3) . . . . ?
N2 C13 C14 C17 0.2(5) . . . . ?
N2 C16 C17 C14 -1.8(5) . . . . ?
N2 C16 C17 C18 175.9(4) . . . . ?
N2 C19 C20 C21 -178.4(4) . . . . ?
N2 C19 C24 C23 178.6(4) . . . . ?
C1 C2 C3 Cl1 -179.4(5) . . . . ?
C1 C2 C3 C4 0.9(10) . . . . ?
C2 C1 C6 N1 178.5(5) . . . . ?
C2 C1 C6 C5 0.0(9) . . . . ?
C2 C3 C4 C5 -1.5(9) . . . . ?
C3 C4 C5 C6 1.4(8) . . . . ?
C4 C5 C6 N1 -179.1(4) . . . . ?
C4 C5 C6 C1 -0.6(8) . . . . ?
C6 N1 C11 C10 -4.2(5) . . . . ?
C6 N1 C11 C12 175.7(4) . . . . ?
C6 N1 C15 O1 3.9(6) . . . . ?
C6 N1 C15 C14 -176.1(3) . . . . ?
C6 C1 C2 C3 -0.2(10) . . . . ?
C7 C8 C9 C10 0.7(7) . . . . ?
C7 C12 C13 N2 -1.2(7) . . . . ?
C7 C12 C13 C14 177.3(4) . . . . ?
C8 C7 C12 C11 -0.9(6) . . . . ?
C8 C7 C12 C13 -178.9(4) . . . . ?
C8 C9 C10 C11 0.7(7) . . . . ?
C9 C10 C11 N1 177.7(4) . . . . ?
C9 C10 C11 C12 -2.2(6) . . . . ?
C10 C11 C12 C7 2.3(6) . . . . ?
C10 C11 C12 C13 -179.5(4) . . . . ?
C11 N1 C6 C1 95.3(5) . . . . ?
C11 N1 C6 C5 -86.2(5) . . . . ?
C11 N1 C15 O1 179.7(4) . . . . ?
C11 N1 C15 C14 -0.2(5) . . . . ?
C11 C12 C13 N2 -179.3(4) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C7 C8 C9 -0.6(7) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C12 C13 C14 C17 -178.6(4) . . . . ?
C13 N2 C16 C17 1.9(5) . . . . ?
C13 N2 C19 C20 -75.6(6) . . . . ?
C13 N2 C19 C24 106.9(5) . . . . ?
C13 C14 C15 O1 -179.9(4) . . . . ?
C13 C14 C15 N1 0.0(6) . . . . ?
C13 C14 C17 C16 0.9(5) . . . . ?
C13 C14 C17 C18 -176.6(4) . . . . ?
C14 C17 C18 O2 178.0(5) . . . . ?
C15 N1 C6 C1 -88.6(6) . . . . ?
C15 N1 C6 C5 89.9(5) . . . . ?
C15 N1 C11 C10 180.0(4) . . . . ?
C15 N1 C11 C12 -0.1(6) . . . . ?
C15 C14 C17 C16 -178.1(4) . . . . ?
C15 C14 C17 C18 4.3(7) . . . . ?
C16 N2 C13 C12 177.4(4) . . . . ?
C16 N2 C13 C14 -1.3(5) . . . . ?
C16 N2 C19 C20 100.7(5) . . . . ?
C16 N2 C19 C24 -76.8(5) . . . . ?
C16 C17 C18 O2 0.9(8) . . . . ?
C17 C14 C15 O1 -1.0(7) . . . . ?
C17 C14 C15 N1 179.0(4) . . . . ?
C19 N2 C13 C12 -5.8(7) . . . . ?
C19 N2 C13 C14 175.5(4) . . . . ?
C19 N2 C16 C17 -175.1(4) . . . . ?
C19 C20 C21 C22 0.2(8) . . . . ?
C20 C19 C24 C23 1.1(7) . . . . ?
C20 C21 C22 Cl2 179.7(4) . . . . ?
C20 C21 C22 C23 0.4(8) . . . . ?
C21 C22 C23 C24 -0.3(8) . . . . ?
C22 C23 C24 C19 -0.5(7) . . . . ?
C24 C19 C20 C21 -0.9(7) . . . . ?

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

data_201412274
_database_code_depnum_ccdc_archive 'CCDC 1057211'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_audit_creation_date             2014-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4973)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H17 Cl N2 O2'
_chemical_formula_sum            'C24 H17 Cl N2 O2'
_chemical_formula_weight         400.85
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Cl1
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'

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

_cell_length_a                   8.0462(5)
_cell_length_b                   9.2337(6)
_cell_length_c                   26.6656(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1981.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.0550
_cell_measurement_theta_min      4.7860
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7586
_diffrn_reflns_theta_full        72.47
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         3.31
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -84.00   -8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -19.0000  120.0000 76

#__ type_ start__ end____ width___ exp.time_
  4 omega   15.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
  5 omega   40.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   85.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  7 omega  100.00  175.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
  8 omega   71.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   48.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  -64.00  -30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   63.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 13 omega  -86.00  -46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 14 omega    1.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   52.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066 -111.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -25.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   46.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -37.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 18 omega   88.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -63.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 19 omega   45.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -63.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   84.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066 -111.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 21 omega  106.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066   77.0000   90.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1672514000
_diffrn_orient_matrix_UB_12      0.0810321000
_diffrn_orient_matrix_UB_13      0.0003004000
_diffrn_orient_matrix_UB_21      -0.0930237000
_diffrn_orient_matrix_UB_22      0.1459185000
_diffrn_orient_matrix_UB_23      -0.0012062000
_diffrn_orient_matrix_UB_31      -0.0029491000
_diffrn_orient_matrix_UB_32      0.0025786000
_diffrn_orient_matrix_UB_33      0.0577468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3048
_reflns_number_total             3843
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0082(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0489P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1123
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.37213(18) 0.35295(15) 0.99291(3) 0.1493(5) Uani 1 d . . .
O1 O 0.4342(3) 0.3672(2) 0.60467(6) 0.0857(6) Uani 1 d . . .
O2 O -0.1046(2) 0.1588(2) 0.83099(6) 0.0815(5) Uani 1 d . . .
N1 N 0.4963(2) 0.38340(19) 0.77509(6) 0.0570(4) Uani 1 d . . .
N2 N 0.2232(2) 0.2705(2) 0.65115(6) 0.0566(4) Uani 1 d . . .
C1 C 0.4157(3) 0.4985(3) 0.85364(9) 0.0684(6) Uani 1 d . . .
H1 H 0.3965 0.5842 0.8363 0.082 Uiso 1 calc . . R
C2 C 0.3866(4) 0.4916(4) 0.90455(10) 0.0840(8) Uani 1 d . . .
H2 H 0.3479 0.5724 0.9218 0.101 Uiso 1 calc . . R
C3 C 0.4156(4) 0.3640(4) 0.92928(9) 0.0837(8) Uani 1 d . . .
C4 C 0.4769(4) 0.2435(3) 0.90470(10) 0.0830(8) Uani 1 d . . .
H4 H 0.4973 0.1582 0.9221 0.100 Uiso 1 calc . . R
C5 C 0.5072(3) 0.2519(3) 0.85410(9) 0.0687(6) Uani 1 d . . .
H5 H 0.5505 0.1726 0.8371 0.082 Uiso 1 calc . . R
C6 C 0.4732(3) 0.3782(2) 0.82867(8) 0.0564(5) Uani 1 d . . .
C7 C 0.6390(3) 0.4332(3) 0.75201(10) 0.0686(6) Uani 1 d . . .
H7 H 0.7328 0.4677 0.7685 0.082 Uiso 1 calc . . R
C8 C 0.6209(3) 0.4238(3) 0.70167(9) 0.0660(6) Uani 1 d . . .
H8 H 0.6988 0.4499 0.6775 0.079 Uiso 1 calc . . R
C9 C 0.3770(3) 0.3377(3) 0.64612(8) 0.0605(5) Uani 1 d . . .
C10 C 0.4604(3) 0.3667(2) 0.69293(8) 0.0564(5) Uani 1 d . . .
C11 C 0.3855(3) 0.3412(2) 0.73861(7) 0.0499(4) Uani 1 d . . .
C12 C 0.2215(2) 0.2805(2) 0.74316(7) 0.0479(4) Uani 1 d . . .
C13 C 0.1451(2) 0.2421(2) 0.69731(7) 0.0501(4) Uani 1 d . . .
C14 C -0.0089(3) 0.1722(2) 0.69909(7) 0.0575(5) Uani 1 d . . .
H14 H -0.0589 0.1430 0.6693 0.069 Uiso 1 calc . . R
C15 C -0.0877(3) 0.1456(3) 0.74362(8) 0.0621(5) Uani 1 d . . .
H15 H -0.1902 0.0989 0.7439 0.075 Uiso 1 calc . . R
C16 C -0.0147(3) 0.1882(2) 0.78817(8) 0.0580(5) Uani 1 d . . .
C17 C 0.1376(3) 0.2544(2) 0.78813(7) 0.0534(5) Uani 1 d . . .
H17 H 0.1856 0.2824 0.8183 0.064 Uiso 1 calc . . R
C18 C -0.0497(4) 0.2236(5) 0.87593(9) 0.0995(11) Uani 1 d . . .
H18A H -0.0438 0.3266 0.8716 0.149 Uiso 1 calc . . GR
H18B H 0.0583 0.1869 0.8844 0.149 Uiso 1 calc . . GR
H18C H -0.1264 0.2013 0.9024 0.149 Uiso 1 calc . . GR
C19 C 0.1345(3) 0.2375(3) 0.60545(7) 0.0664(6) Uani 1 d . . .
C20 C 0.0178(6) 0.3321(4) 0.58865(14) 0.1200(13) Uani 1 d . . .
H20 H -0.0037 0.4170 0.6063 0.144 Uiso 1 calc . . R
C21 C -0.0687(7) 0.3011(6) 0.54507(17) 0.161(2) Uani 1 d . . .
H21 H -0.1493 0.3649 0.5334 0.194 Uiso 1 calc . . R
C22 C -0.0356(7) 0.1762(7) 0.51919(11) 0.148(2) Uani 1 d . . .
H22 H -0.0915 0.1565 0.4894 0.177 Uiso 1 calc . . R
C23 C 0.0772(6) 0.0827(6) 0.53675(13) 0.1306(19) Uani 1 d . . .
H23 H 0.0966 -0.0032 0.5195 0.157 Uiso 1 calc . . R
C24 C 0.1663(4) 0.1118(4) 0.58054(10) 0.0921(10) Uani 1 d . . .
H24 H 0.2454 0.0468 0.5924 0.111 Uiso 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 C3 1.735(3) . ?
O1 C9 1.228(3) . ?
O2 C16 1.379(3) . ?
O2 C18 1.410(3) . ?
N1 C6 1.441(3) . ?
N1 C7 1.382(3) . ?
N1 C11 1.376(3) . ?
N2 C9 1.391(3) . ?
N2 C13 1.407(3) . ?
N2 C19 1.444(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(3) . ?
C1 C6 1.376(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(5) . ?
C3 C4 1.383(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.353(3) . ?
C8 H8 0.9300 . ?
C8 C10 1.415(3) . ?
C9 C10 1.442(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.439(3) . ?
C12 C13 1.414(3) . ?
C12 C17 1.397(3) . ?
C13 C14 1.398(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C16 C17 1.369(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.358(5) . ?
C19 C24 1.362(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.338(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.396(4) . ?
C24 H24 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
C16 O2 C18 117.1(2) . . ?
C7 N1 C6 124.03(19) . . ?
C11 N1 C6 127.5(2) . . ?
C11 N1 C7 108.52(19) . . ?
C9 N2 C13 124.39(18) . . ?
C9 N2 C19 116.89(18) . . ?
C13 N2 C19 118.58(19) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.8(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 Cl1 119.2(2) . . ?
C2 C3 C4 121.6(2) . . ?
C4 C3 Cl1 119.2(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 N1 119.7(2) . . ?
C5 C6 N1 119.4(2) . . ?
C5 C6 C1 120.8(2) . . ?
N1 C7 H7 125.3 . . ?
C8 C7 N1 109.4(2) . . ?
C8 C7 H7 125.3 . . ?
C7 C8 H8 126.7 . . ?
C7 C8 C10 106.6(2) . . ?
C10 C8 H8 126.7 . . ?
O1 C9 N2 121.3(2) . . ?
O1 C9 C10 124.3(2) . . ?
N2 C9 C10 114.43(18) . . ?
C8 C10 C9 129.5(2) . . ?
C11 C10 C8 108.5(2) . . ?
C11 C10 C9 121.95(19) . . ?
N1 C11 C10 107.04(19) . . ?
N1 C11 C12 130.15(19) . . ?
C10 C11 C12 122.81(18) . . ?
C13 C12 C11 115.05(18) . . ?
C17 C12 C11 125.65(19) . . ?
C17 C12 C13 119.28(18) . . ?
N2 C13 C12 121.07(18) . . ?
C14 C13 N2 120.77(18) . . ?
C14 C13 C12 118.15(18) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
O2 C16 C15 115.6(2) . . ?
C17 C16 O2 123.9(2) . . ?
C17 C16 C15 120.5(2) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.66(18) . . ?
C16 C17 H17 119.7 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 N2 118.9(3) . . ?
C20 C19 C24 121.2(3) . . ?
C24 C19 N2 119.9(3) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.4(4) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(5) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 119.9(4) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.1(4) . . ?
C24 C23 H23 119.4 . . ?
C19 C24 C23 118.4(4) . . ?
C19 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?

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 C3 C4 C5 178.4(2) . . . . ?
O1 C9 C10 C8 -4.1(4) . . . . ?
O1 C9 C10 C11 175.1(2) . . . . ?
O2 C16 C17 C12 179.9(2) . . . . ?
N1 C7 C8 C10 0.3(3) . . . . ?
N1 C11 C12 C13 -176.70(19) . . . . ?
N1 C11 C12 C17 1.6(3) . . . . ?
N2 C9 C10 C8 175.3(2) . . . . ?
N2 C9 C10 C11 -5.6(3) . . . . ?
N2 C13 C14 C15 -179.0(2) . . . . ?
N2 C19 C20 C21 -179.5(4) . . . . ?
N2 C19 C24 C23 179.4(3) . . . . ?
C1 C2 C3 Cl1 -177.7(2) . . . . ?
C1 C2 C3 C4 1.6(5) . . . . ?
C2 C1 C6 N1 177.1(2) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C4 C5 C6 N1 -176.4(2) . . . . ?
C4 C5 C6 C1 2.7(4) . . . . ?
C6 N1 C7 C8 180.0(2) . . . . ?
C6 N1 C11 C10 179.6(2) . . . . ?
C6 N1 C11 C12 -0.7(4) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C7 N1 C6 C1 85.9(3) . . . . ?
C7 N1 C6 C5 -94.9(3) . . . . ?
C7 N1 C11 C10 -0.6(2) . . . . ?
C7 N1 C11 C12 179.1(2) . . . . ?
C7 C8 C10 C9 178.6(2) . . . . ?
C7 C8 C10 C11 -0.7(3) . . . . ?
C8 C10 C11 N1 0.7(2) . . . . ?
C8 C10 C11 C12 -178.92(19) . . . . ?
C9 N2 C13 C12 -0.5(3) . . . . ?
C9 N2 C13 C14 -179.1(2) . . . . ?
C9 N2 C19 C20 -95.7(3) . . . . ?
C9 N2 C19 C24 85.6(3) . . . . ?
C9 C10 C11 N1 -178.6(2) . . . . ?
C9 C10 C11 C12 1.8(3) . . . . ?
C10 C11 C12 C13 2.9(3) . . . . ?
C10 C11 C12 C17 -178.8(2) . . . . ?
C11 N1 C6 C1 -94.3(3) . . . . ?
C11 N1 C6 C5 84.9(3) . . . . ?
C11 N1 C7 C8 0.2(3) . . . . ?
C11 C12 C13 N2 -3.5(3) . . . . ?
C11 C12 C13 C14 175.09(18) . . . . ?
C11 C12 C17 C16 -176.1(2) . . . . ?
C12 C13 C14 C15 2.3(3) . . . . ?
C13 N2 C9 O1 -175.6(2) . . . . ?
C13 N2 C9 C10 5.0(3) . . . . ?
C13 N2 C19 C20 80.1(3) . . . . ?
C13 N2 C19 C24 -98.6(3) . . . . ?
C13 C12 C17 C16 2.1(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 O2 179.0(2) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C17 C12 C13 N2 178.07(19) . . . . ?
C17 C12 C13 C14 -3.3(3) . . . . ?
C18 O2 C16 C15 -168.7(3) . . . . ?
C18 O2 C16 C17 11.6(4) . . . . ?
C19 N2 C9 O1 -0.1(4) . . . . ?
C19 N2 C9 C10 -179.4(2) . . . . ?
C19 N2 C13 C12 -176.0(2) . . . . ?
C19 N2 C13 C14 5.4(3) . . . . ?
C19 C20 C21 C22 -0.4(7) . . . . ?
C20 C19 C24 C23 0.7(5) . . . . ?
C20 C21 C22 C23 1.7(8) . . . . ?
C21 C22 C23 C24 -1.9(7) . . . . ?
C22 C23 C24 C19 0.7(5) . . . . ?
C24 C19 C20 C21 -0.9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
