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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_LON-IMID_1-1_solvate
_database_code_depnum_ccdc_archive 'CCDC 1531955'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-04-15
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Cl2 N2 O2, C3 H5 N2, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C20 H18 Cl2 N4 O3'
_chemical_formula_weight         433.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C120 H108 N24 O18 Cl12'
_chemical_oxdiff_usercomment     'L3-85-C1 recollect'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.1394(5)
_cell_length_b                   29.9418(9)
_cell_length_c                   26.9456(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.628(2)
_cell_angle_gamma                90
_cell_volume                     12106.4(6)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    19472
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8970
_cell_measurement_theta_min      2.7020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             5376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
19 18 -14 0.1096
-17 -23 11 0.0756
-19 2 20 0.1054
17 -15 -21 0.1115
0 -40 -11 0.1490
5 -6 35 0.0585
-3 4 -37 0.0703
-3 39 14 0.1829
13 34 -4 0.1521

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.145
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
18.9782 18.1053 -13.8869 0.7979 -0.2907 -0.5631
-16.9653 -23.0916 10.8976 -0.8439 0.2996 0.4046
-19.0258 1.8847 19.8912 -0.4331 0.1411 0.8703
17.0525 -14.8914 -20.9051 0.1398 -0.0465 -0.9711
0.0929 -39.9815 -11.0082 -0.7375 0.2769 -0.6021
4.9203 -6.0232 35.0524 -0.3137 -0.9262 0.2024
-2.9149 4.0354 -37.0410 0.3216 0.9104 -0.3136
-3.0944 38.9636 13.9909 0.6432 -0.2501 0.7222
12.9356 34.0625 -3.9184 0.9487 -0.3405 -0.0637

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            86240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.451
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  91.00   0.50   60.00    --   15.17  57.00 -30.00  208
  2  ω    -62.00  38.00   0.50   60.00    --   15.17 -38.00-180.00  200
  3  ω    -28.00   7.00   0.50   60.00    --   15.17 -38.00-120.00   70
  4  ω     10.00  64.00   0.50   60.00    --   15.17  77.00 150.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0167002000
_diffrn_orient_matrix_UB_12      0.0206181000
_diffrn_orient_matrix_UB_13      -0.0077512000
_diffrn_orient_matrix_UB_21      -0.0307673000
_diffrn_orient_matrix_UB_22      -0.0008711000
_diffrn_orient_matrix_UB_23      -0.0222531000
_diffrn_orient_matrix_UB_31      -0.0318018000
_diffrn_orient_matrix_UB_32      0.0116157000
_diffrn_orient_matrix_UB_33      0.0122354000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                20228
_reflns_number_total             27727
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         2.087
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.093
_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     1638
_refine_ls_number_reflns         27727
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+11.8820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1737
_refine_special_details          
;
Disorder is present in two of the six dichlorine-substituted aromatic rings of lonidamine, in approximate ratios 75:25 (resi 4) and 80:20 (resi 5), and in one ethyl acetate moeity (resi 15) in an approximate ratio 55:45
Residual density occurs due to further disorder in other dichlorine-substituted rings of lonidamine moeities, due to greater angles of rotation around the C9-C10 bond.  The minor disordered component was seen to be at a very low level when modelling attempted (~94:6 ratio) and the inclusion of such modelling does not add to or improve the model dramatically.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11_5) = Uanis(C11A_5)
Uanis(C12_5) = Uanis(C12A_5)
Uanis(C14_5) = Uanis(C14A_5)
Uanis(C15_5) = Uanis(C15A_5)
Uanis(C15_4) = Uanis(C15A_4)
Uanis(C14_4) = Uanis(C14A_4)
Uanis(C12_4) = Uanis(C12A_4)
Uanis(C11_4) = Uanis(C11A_4)
Uanis(Cl1_5) = Uanis(Cl1A_5)
Uanis(O32A_15) = Uanis(O32_15)
3. Rigid body (RIGU) restrains
 C10_5, C11A_5, C12A_5, C13_5, C14A_5, C15A_5, C11_5, C12_5, C14_5, C15_5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O31)=Sof(O32)=Sof(C33)=Sof(H33C)=Sof(H33D)=Sof(C31)=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=Sof(C34)=Sof(H34D)=Sof(H34E)=Sof(H34F)=Sof(C32)=1-FVAR(1)
 Sof(O31A)=Sof(O32A)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(C31A)=Sof(H31A)=
 Sof(H31B)=Sof(H31C)=Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C32A)=FVAR(1)
 Sof(Cl1)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=1-
 FVAR(2)
 Sof(Cl1A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=FVAR(2)
 Sof(Cl1A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=1-FVAR(3)
 Sof(Cl1)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9(H9A,H9B), C9(H9A,H9B), C9(H9A,H9B), C9(H9A,H9B), C9(H9A,H9B),
 C31(H31A,H31B), C33(H33A,H33B), C33A(H33A,H33B), C33(H33C,H33D)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C4(H4), C5(H5),
 C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C4(H4), C5(H5), C6(H6), C7(H7),
 C12(H12), C14(H14), C15(H15), C4(H4), C5(H5), C6(H6), C7(H7), C12A(H12A),
 C14A(H14A), C15A(H15A), C12(H12), C14(H14), C15(H15), C4(H4), C5(H5), C6(H6),
 C7(H7), C12A(H12A), C14A(H14A), C15A(H15A), C12(H12), C14(H14), C15(H15),
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), N21(H21),
 N22(H22), C21(H21A), C22(H22A), C23(H23), N21(H21), N22(H22), C21(H21A),
 C22(H22A), C23(H23), N21(H21), N22(H22), C21(H21A), C22(H22A), C23(H23),
 N21(H21), N22(H22), C21(H21A), C22(H22A), C23(H23), N21(H21), N22(H22),
 C21(H21A), C22(H22A), C23(H23), N21(H21), N22(H22), C21(H21A), C22(H22A),
 C23(H23)
5.c Fitted hexagon refined as free rotating group:
 C10(C11A,C12A,C13,C14A,C15A), C10(C11A,C12A,C13,C14A,C15A)
5.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C31(H31A,H31B,H31C), C34(H34A,H34B,
 H34C), C31A(H31A,H31B,H31C), C34A(H34A,H34B,H34C), C31(H31D,H31E,H31F),
 C34(H34D,H34E,H34F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1_1 Cl 0.52592(5) 0.22298(2) 0.31558(2) 0.02781(16) Uani 1 1 d . . . . .
Cl2_1 Cl 0.60511(5) 0.10003(3) 0.18458(2) 0.03124(17) Uani 1 1 d . . . . .
O1_1 O 0.44495(11) 0.28852(6) 0.46008(6) 0.0160(4) Uani 1 1 d . . . . .
O2_1 O 0.33386(11) 0.24508(6) 0.47956(6) 0.0163(4) Uani 1 1 d . . . . .
N1_1 N 0.55864(13) 0.17191(7) 0.42187(7) 0.0133(4) Uani 1 1 d . . . . .
N2_1 N 0.53383(12) 0.21394(7) 0.43302(7) 0.0125(4) Uani 1 1 d . . . . .
C1_1 C 0.40899(15) 0.25083(8) 0.46484(8) 0.0117(4) Uani 1 1 d . . . . .
C2_1 C 0.45717(15) 0.20990(8) 0.45168(8) 0.0110(4) Uani 1 1 d . . . . .
C3_1 C 0.43020(15) 0.16407(8) 0.45283(8) 0.0116(4) Uani 1 1 d . . . . .
C4_1 C 0.35789(15) 0.14062(8) 0.46792(9) 0.0149(5) Uani 1 1 d . . . . .
H4_1 H 0.3118 0.1559 0.4817 0.018 Uiso 1 1 calc R . . . .
C5_1 C 0.35558(17) 0.09471(9) 0.46227(10) 0.0204(5) Uani 1 1 d . . . . .
H5_1 H 0.3071 0.0783 0.4721 0.025 Uiso 1 1 calc R . . . .
C6_1 C 0.42441(18) 0.07167(9) 0.44201(10) 0.0236(6) Uani 1 1 d . . . . .
H6_1 H 0.4211 0.0401 0.4387 0.028 Uiso 1 1 calc R . . . .
C7_1 C 0.49621(17) 0.09396(8) 0.42691(10) 0.0195(5) Uani 1 1 d . . . . .
H7_1 H 0.5421 0.0785 0.4132 0.023 Uiso 1 1 calc R . . . .
C8_1 C 0.49799(15) 0.14057(8) 0.43288(8) 0.0131(5) Uani 1 1 d . . . . .
C9_1 C 0.64002(15) 0.16501(9) 0.39936(9) 0.0155(5) Uani 1 1 d . . . . .
H9A_1 H 0.6775 0.1429 0.4197 0.019 Uiso 1 1 calc R . . . .
H9B_1 H 0.6736 0.1935 0.4008 0.019 Uiso 1 1 calc R . . . .
C10_1 C 0.62534(15) 0.14898(8) 0.34531(9) 0.0139(5) Uani 1 1 d . . . . .
C11_1 C 0.57829(17) 0.17265(9) 0.30540(9) 0.0192(5) Uani 1 1 d . . . . .
C12_1 C 0.57164(17) 0.15745(9) 0.25618(10) 0.0230(6) Uani 1 1 d . . . . .
H12_1 H 0.5401 0.1743 0.2296 0.028 Uiso 1 1 calc R . . . .
C13_1 C 0.61180(17) 0.11746(10) 0.24675(9) 0.0227(6) Uani 1 1 d . . . . .
C14_1 C 0.65716(17) 0.09216(9) 0.28482(10) 0.0226(6) Uani 1 1 d . . . . .
H14_1 H 0.6831 0.0644 0.2779 0.027 Uiso 1 1 calc R . . . .
C15_1 C 0.66390(17) 0.10845(9) 0.33369(9) 0.0203(5) Uani 1 1 d . . . . .
H15_1 H 0.6957 0.0915 0.3600 0.024 Uiso 1 1 calc R . . . .
Cl1_2 Cl 0.41824(4) 0.52505(2) 0.83107(2) 0.02405(15) Uani 1 1 d . . . . .
Cl2_2 Cl 0.21549(5) 0.55043(3) 0.65360(3) 0.0413(2) Uani 1 1 d . . . . .
O1_2 O 0.57806(11) 0.38105(6) 0.56581(6) 0.0149(3) Uani 1 1 d . . . . .
O2_2 O 0.68965(11) 0.42531(6) 0.54861(7) 0.0185(4) Uani 1 1 d . . . . .
N1_2 N 0.44760(12) 0.49908(7) 0.58410(7) 0.0125(4) Uani 1 1 d . . . . .
N2_2 N 0.47910(12) 0.45665(7) 0.58206(7) 0.0126(4) Uani 1 1 d . . . . .
C1_2 C 0.61159(15) 0.41880(8) 0.55912(8) 0.0117(4) Uani 1 1 d . . . . .
C2_2 C 0.55722(14) 0.45973(8) 0.56475(8) 0.0105(4) Uani 1 1 d . . . . .
C3_2 C 0.57885(15) 0.50528(8) 0.55552(8) 0.0106(4) Uani 1 1 d . . . . .
C4_2 C 0.64925(15) 0.52808(8) 0.53737(8) 0.0139(5) Uani 1 1 d . . . . .
H4_2 H 0.6982 0.5122 0.5272 0.017 Uiso 1 1 calc R . . . .
C5_2 C 0.64522(17) 0.57421(8) 0.53469(9) 0.0173(5) Uani 1 1 d . . . . .
H5_2 H 0.6923 0.5901 0.5227 0.021 Uiso 1 1 calc R . . . .
C6_2 C 0.57235(17) 0.59822(8) 0.54947(9) 0.0184(5) Uani 1 1 d . . . . .
H6_2 H 0.5719 0.6299 0.5474 0.022 Uiso 1 1 calc R . . . .
C7_2 C 0.50196(16) 0.57663(8) 0.56686(8) 0.0156(5) Uani 1 1 d . . . . .
H7_2 H 0.4531 0.5927 0.5768 0.019 Uiso 1 1 calc R . . . .
C8_2 C 0.50595(15) 0.52978(8) 0.56912(8) 0.0116(4) Uani 1 1 d . . . . .
C9_2 C 0.36543(15) 0.50757(9) 0.60503(8) 0.0152(5) Uani 1 1 d . . . . .
H9A_2 H 0.3236 0.4826 0.5961 0.018 Uiso 1 1 calc R . . . .
H9B_2 H 0.3375 0.5351 0.5899 0.018 Uiso 1 1 calc R . . . .
C10_2 C 0.38047(15) 0.51278(8) 0.66169(8) 0.0141(5) Uani 1 1 d . . . . .
C11_2 C 0.31571(16) 0.53169(10) 0.68729(9) 0.0213(6) Uani 1 1 d . . . . .
C12_2 C 0.32568(18) 0.53526(10) 0.73894(10) 0.0265(6) Uani 1 1 d . . . . .
H12_2 H 0.2799 0.5478 0.7555 0.032 Uiso 1 1 calc R . . . .
C13_2 C 0.40435(16) 0.52001(9) 0.76594(9) 0.0179(5) Uani 1 1 d . . . . .
C14_2 C 0.47049(17) 0.50111(10) 0.74233(9) 0.0244(6) Uani 1 1 d . . . . .
H14_2 H 0.5239 0.4906 0.7612 0.029 Uiso 1 1 calc R . . . .
C15_2 C 0.45764(16) 0.49769(10) 0.69030(9) 0.0227(6) Uani 1 1 d . . . . .
H15_2 H 0.5031 0.4846 0.6739 0.027 Uiso 1 1 calc R . . . .
Cl1_3 Cl 1.02727(5) 0.44087(2) 0.30751(2) 0.02726(15) Uani 1 1 d . . . . .
Cl2_3 Cl 1.09792(5) 0.56514(3) 0.17519(2) 0.03118(17) Uani 1 1 d . . . . .
O1_3 O 0.94337(11) 0.37827(6) 0.45641(6) 0.0157(3) Uani 1 1 d . . . . .
O2_3 O 0.83191(11) 0.42237(6) 0.47397(6) 0.0170(4) Uani 1 1 d . . . . .
N1_3 N 1.05478(12) 0.49386(7) 0.41226(7) 0.0130(4) Uani 1 1 d . . . . .
N2_3 N 1.03090(13) 0.45202(7) 0.42525(7) 0.0129(4) Uani 1 1 d . . . . .
C13_3 C 1.10668(17) 0.54737(10) 0.23747(9) 0.0224(6) Uani 1 1 d . . . . .
C1_3 C 0.90720(15) 0.41588(8) 0.45933(8) 0.0118(5) Uani 1 1 d . . . . .
C2_3 C 0.95393(15) 0.45647(8) 0.44388(8) 0.0111(4) Uani 1 1 d . . . . .
C3_3 C 0.92654(14) 0.50214(8) 0.44319(8) 0.0109(4) Uani 1 1 d . . . . .
C4_3 C 0.85359(15) 0.52586(8) 0.45767(9) 0.0152(5) Uani 1 1 d . . . . .
H4_3 H 0.8080 0.5109 0.4722 0.018 Uiso 1 1 calc R . . . .
C5_3 C 0.85035(17) 0.57142(9) 0.45008(10) 0.0222(6) Uani 1 1 d . . . . .
H5_3 H 0.8016 0.5879 0.4594 0.027 Uiso 1 1 calc R . . . .
C6_3 C 0.91841(18) 0.59420(9) 0.42863(11) 0.0249(6) Uani 1 1 d . . . . .
H6_3 H 0.9141 0.6256 0.4239 0.030 Uiso 1 1 calc R . . . .
C7_3 C 0.99087(17) 0.57163(8) 0.41448(10) 0.0195(5) Uani 1 1 d . . . . .
H7_3 H 1.0366 0.5868 0.4003 0.023 Uiso 1 1 calc R . . . .
C8_3 C 0.99360(15) 0.52525(8) 0.42214(8) 0.0129(5) Uani 1 1 d . . . . .
C9_3 C 1.13651(15) 0.50027(9) 0.38992(8) 0.0150(5) Uani 1 1 d . . . . .
H9A_3 H 1.1696 0.4717 0.3916 0.018 Uiso 1 1 calc R . . . .
H9B_3 H 1.1742 0.5224 0.4102 0.018 Uiso 1 1 calc R . . . .
C10_3 C 1.12197(15) 0.51602(9) 0.33587(9) 0.0152(5) Uani 1 1 d . . . . .
C11_3 C 1.07674(16) 0.49184(9) 0.29645(9) 0.0192(5) Uani 1 1 d . . . . .
C12_3 C 1.06845(17) 0.50684(9) 0.24706(10) 0.0228(6) Uani 1 1 d . . . . .
H12_3 H 1.0373 0.4897 0.2207 0.027 Uiso 1 1 calc R . . . .
C14_3 C 1.15081(17) 0.57346(9) 0.27509(10) 0.0219(5) Uani 1 1 d . . . . .
H14_3 H 1.1753 0.6016 0.2679 0.026 Uiso 1 1 calc R . . . .
C15_3 C 1.15843(17) 0.55737(9) 0.32398(9) 0.0198(5) Uani 1 1 d . . . . .
H15_3 H 1.1892 0.5748 0.3502 0.024 Uiso 1 1 calc R . . . .
Cl1_4 Cl -0.24943(17) 0.10679(7) 0.66825(4) 0.0417(6) Uani 0.753(7) 1 d . . P A
1
Cl1A_4 Cl -0.1921(7) 0.0848(3) 0.67217(13) 0.064(4) Uani 0.247(7) 1 d . . P A 2
Cl2_4 Cl -0.06722(5) 0.16630(3) 0.84121(2) 0.03381(18) Uani 1 1 d . . . . .
O1_4 O 0.07623(10) 0.29051(5) 0.56658(6) 0.0135(3) Uani 1 1 d . . . . .
O2_4 O 0.18853(11) 0.24702(6) 0.54900(6) 0.0173(4) Uani 1 1 d . . . . .
N1_4 N -0.04970(13) 0.17387(7) 0.59203(7) 0.0131(4) Uani 1 1 d . . . . .
N2_4 N -0.01862(12) 0.21593(7) 0.58654(7) 0.0126(4) Uani 1 1 d . . . . .
C1_4 C 0.11155(15) 0.25285(8) 0.56093(8) 0.0113(4) Uani 1 1 d . . . . .
C2_4 C 0.05938(14) 0.21176(8) 0.56935(8) 0.0102(4) Uani 1 1 d . . . . .
C3_4 C 0.08101(15) 0.16568(8) 0.56367(8) 0.0114(4) Uani 1 1 d . . . . .
C4_4 C 0.15226(16) 0.14194(9) 0.54728(9) 0.0159(5) Uani 1 1 d . . . . .
H4_4 H 0.2007 0.1572 0.5357 0.019 Uiso 1 1 calc R . . . .
C5_4 C 0.14936(17) 0.09566(9) 0.54858(9) 0.0204(5) Uani 1 1 d . . . . .
H5_4 H 0.1969 0.0790 0.5379 0.025 Uiso 1 1 calc R . . . .
C6_4 C 0.07704(18) 0.07252(9) 0.56543(10) 0.0216(5) Uani 1 1 d . . . . .
H6_4 H 0.0775 0.0408 0.5661 0.026 Uiso 1 1 calc R . . . .
C7_4 C 0.00583(17) 0.09517(8) 0.58092(9) 0.0177(5) Uani 1 1 d . . . . .
H7_4 H -0.0428 0.0798 0.5921 0.021 Uiso 1 1 calc R . . . .
C8_4 C 0.00888(15) 0.14221(8) 0.57935(8) 0.0125(5) Uani 1 1 d . . . . .
C9_4 C -0.13055(16) 0.16728(9) 0.61449(9) 0.0165(5) Uani 1 1 d . . . . .
H9A_4 H -0.1583 0.1386 0.6025 0.020 Uiso 1 1 calc R . . . .
H9B_4 H -0.1731 0.1915 0.6034 0.020 Uiso 1 1 calc R . . . .
C10_4 C -0.11367(15) 0.16672(8) 0.67181(6) 0.0155(5) Uani 1 1 d . . . . .
C11A_4 C -0.1449(7) 0.1317(2) 0.69859(9) 0.0249(10) Uani 0.247(7) 1 d G . P A 2
C12A_4 C -0.1305(7) 0.1320(2) 0.75062(9) 0.0282(10) Uani 0.247(7) 1 d G . P A 2
H12A_4 H -0.1518 0.1081 0.7689 0.034 Uiso 0.247(7) 1 calc R . P A 2
C13_4 C -0.08490(17) 0.16735(9) 0.77587(6) 0.0211(5) Uani 1 1 d G . . A .
C14A_4 C -0.0537(7) 0.2023(2) 0.74909(9) 0.0174(8) Uani 0.247(7) 1 d G . P A 2
H14A_4 H -0.0225 0.2265 0.7663 0.021 Uiso 0.247(7) 1 calc R . P A 2
C15A_4 C -0.0681(7) 0.20202(19) 0.69706(9) 0.0150(8) Uani 0.247(7) 1 d G . P A
2
H15A_4 H -0.0467 0.2259 0.6788 0.018 Uiso 0.247(7) 1 calc R . P A 2
C11_4 C -0.1655(3) 0.14100(14) 0.69940(13) 0.0249(10) Uani 0.753(7) 1 d . . P A
1
C12_4 C -0.1522(3) 0.14063(15) 0.75138(13) 0.0282(10) Uani 0.753(7) 1 d . . P A
1
H12_4 H -0.1882 0.1226 0.7697 0.034 Uiso 0.753(7) 1 calc R . P A 1
C14_4 C -0.0355(2) 0.19578(13) 0.74987(12) 0.0174(8) Uani 0.753(7) 1 d . . P A
1
H14_4 H 0.0073 0.2154 0.7672 0.021 Uiso 0.753(7) 1 calc R . P A 1
C15_4 C -0.0499(2) 0.19490(12) 0.69803(12) 0.0150(8) Uani 0.753(7) 1 d . . P A
1
H15_4 H -0.0157 0.2139 0.6798 0.018 Uiso 0.753(7) 1 calc R . P A 1
Cl1_5 Cl 0.74001(10) 0.72990(4) 0.82810(3) 0.0412(4) Uani 0.799(2) 1 d . . P B
1
Cl1A_5 Cl 0.6882(4) 0.74765(18) 0.82390(14) 0.0412(4) Uani 0.201(2) 1 d . . P B
2
Cl2_5 Cl 0.56172(5) 0.66354(3) 0.65788(2) 0.03497(19) Uani 1 1 d . . . . .
O1_5 O 0.43160(11) 0.54323(6) 0.94348(6) 0.0146(3) Uani 1 1 d . . . . .
O2_5 O 0.31751(11) 0.58726(6) 0.95765(6) 0.0177(4) Uani 1 1 d . . . . .
N1_5 N 0.55108(13) 0.65903(7) 0.90755(7) 0.0127(4) Uani 1 1 d . . . . .
N2_5 N 0.52270(12) 0.61708(7) 0.91650(7) 0.0121(4) Uani 1 1 d . . . . .
C1_5 C 0.39460(15) 0.58094(8) 0.94599(8) 0.0113(4) Uani 1 1 d . . . . .
C2_5 C 0.44458(14) 0.62157(8) 0.93341(8) 0.0104(4) Uani 1 1 d . . . . .
C3_5 C 0.41956(15) 0.66766(8) 0.93492(8) 0.0115(4) Uani 1 1 d . . . . .
C4_5 C 0.34715(15) 0.69183(8) 0.94903(8) 0.0147(5) Uani 1 1 d . . . . .
H4_5 H 0.2996 0.6770 0.9619 0.018 Uiso 1 1 calc R . . . .
C5_5 C 0.34726(17) 0.73787(9) 0.94357(9) 0.0198(5) Uani 1 1 d . . . . .
H5_5 H 0.2988 0.7547 0.9528 0.024 Uiso 1 1 calc R . . . .
C6_5 C 0.41816(17) 0.76040(8) 0.92456(9) 0.0196(5) Uani 1 1 d . . . . .
H6_5 H 0.4156 0.7919 0.9209 0.024 Uiso 1 1 calc R . . . .
C7_5 C 0.49071(16) 0.73755(8) 0.91123(9) 0.0167(5) Uani 1 1 d . . . . .
H7_5 H 0.5384 0.7526 0.8988 0.020 Uiso 1 1 calc R . . . .
C8_5 C 0.49049(15) 0.69081(8) 0.91704(8) 0.0119(5) Uani 1 1 d . . . . .
C9_5 C 0.63162(15) 0.66506(9) 0.88436(9) 0.0155(5) Uani 1 1 d . . . . .
H9A_5 H 0.6739 0.6407 0.8953 0.019 Uiso 1 1 calc R . . . .
H9B_5 H 0.6601 0.6936 0.8959 0.019 Uiso 1 1 calc R . . . .
C10_5 C 0.61334(15) 0.66527(8) 0.82715(6) 0.0150(5) Uani 1 1 d . U . . .
C11A_5 C 0.6440(12) 0.6998(4) 0.79946(9) 0.0256(10) Uani 0.201(2) 1 d G U P B 2
C12A_5 C 0.6279(12) 0.6989(4) 0.74747(9) 0.0297(11) Uani 0.201(2) 1 d G U P B 2
H12A_5 H 0.6488 0.7225 0.7285 0.036 Uiso 0.201(2) 1 calc R . P B 2
C13_5 C 0.58110(17) 0.66345(9) 0.72317(6) 0.0217(5) Uani 1 1 d G U . B .
C14A_5 C 0.5505(12) 0.6289(4) 0.75086(9) 0.0199(9) Uani 0.201(2) 1 d G U P B 2
H14A_5 H 0.5185 0.6047 0.7343 0.024 Uiso 0.201(2) 1 calc R . P B 2
C15A_5 C 0.5666(12) 0.6298(4) 0.80285(9) 0.0184(9) Uani 0.201(2) 1 d G U P B 2
H15A_5 H 0.5456 0.6062 0.8218 0.022 Uiso 0.201(2) 1 calc R . P B 2
C11_5 C 0.6585(3) 0.69314(13) 0.79853(12) 0.0256(10) Uani 0.799(2) 1 d . U P B
1
C12_5 C 0.6435(3) 0.69312(14) 0.74649(13) 0.0297(11) Uani 0.799(2) 1 d . U P B
1
H12_5 H 0.6750 0.7128 0.7275 0.036 Uiso 0.799(2) 1 calc R . P B 1
C14_5 C 0.5360(3) 0.63388(13) 0.74998(12) 0.0199(9) Uani 0.799(2) 1 d . U P B 1
H14_5 H 0.4948 0.6132 0.7333 0.024 Uiso 0.799(2) 1 calc R . P B 1
C15_5 C 0.5522(3) 0.63501(12) 0.80191(12) 0.0184(9) Uani 0.799(2) 1 d . U P B 1
H15_5 H 0.5212 0.6149 0.8208 0.022 Uiso 0.799(2) 1 calc R . P B 1
Cl1_6 Cl 0.29002(4) 0.28303(3) 0.85385(2) 0.02915(17) Uani 1 1 d . . . . .
Cl2_6 Cl 0.08536(4) 0.30718(2) 0.67730(2) 0.02389(15) Uani 1 1 d . . . . .
O1_6 O -0.06821(11) 0.45230(6) 0.94761(6) 0.0165(4) Uani 1 1 d . . . . .
O2_6 O -0.18176(11) 0.40848(6) 0.96223(7) 0.0208(4) Uani 1 1 d . . . . .
N1_6 N 0.05785(13) 0.33375(7) 0.92447(7) 0.0122(4) Uani 1 1 d . . . . .
N2_6 N 0.02836(12) 0.37624(7) 0.92843(7) 0.0124(4) Uani 1 1 d . . . . .
C1_6 C -0.10313(15) 0.41449(8) 0.95209(8) 0.0128(5) Uani 1 1 d . . . . .
C2_6 C -0.05086(15) 0.37342(8) 0.94504(8) 0.0108(4) Uani 1 1 d . . . . .
C3_6 C -0.07428(14) 0.32779(8) 0.95184(8) 0.0102(4) Uani 1 1 d . . . . .
C4_6 C -0.14649(15) 0.30497(8) 0.96858(8) 0.0133(5) Uani 1 1 d . . . . .
H4_6 H -0.1947 0.3209 0.9795 0.016 Uiso 1 1 calc R . . . .
C5_6 C -0.14488(17) 0.25883(9) 0.96866(9) 0.0177(5) Uani 1 1 d . . . . .
H5_6 H -0.1928 0.2429 0.9798 0.021 Uiso 1 1 calc R . . . .
C6_6 C -0.07332(17) 0.23469(9) 0.95242(9) 0.0186(5) Uani 1 1 d . . . . .
H6_6 H -0.0750 0.2030 0.9525 0.022 Uiso 1 1 calc R . . . .
C7_6 C -0.00139(16) 0.25604(8) 0.93652(8) 0.0154(5) Uani 1 1 d . . . . .
H7_6 H 0.0465 0.2399 0.9257 0.018 Uiso 1 1 calc R . . . .
C8_6 C -0.00279(15) 0.30308(8) 0.93726(8) 0.0114(4) Uani 1 1 d . . . . .
C9_6 C 0.13970(15) 0.32509(9) 0.90337(8) 0.0148(5) Uani 1 1 d . . . . .
H9A_6 H 0.1676 0.2975 0.9185 0.018 Uiso 1 1 calc R . . . .
H9B_6 H 0.1817 0.3501 0.9121 0.018 Uiso 1 1 calc R . . . .
C10_6 C 0.12434(15) 0.31977(8) 0.84680(8) 0.0131(5) Uani 1 1 d . . . . .
C11_6 C 0.18950(15) 0.30133(9) 0.82103(9) 0.0162(5) Uani 1 1 d . . . . .
C12_6 C 0.17899(16) 0.29776(9) 0.76924(9) 0.0197(5) Uani 1 1 d . . . . .
H12_6 H 0.2252 0.2858 0.7525 0.024 Uiso 1 1 calc R . . . .
C13_6 C 0.09931(16) 0.31209(9) 0.74236(9) 0.0171(5) Uani 1 1 d . . . . .
C14_6 C 0.03254(17) 0.33051(10) 0.76618(9) 0.0229(6) Uani 1 1 d . . . . .
H14_6 H -0.0215 0.3405 0.7475 0.028 Uiso 1 1 calc R . . . .
C15_6 C 0.04602(16) 0.33414(9) 0.81825(9) 0.0204(5) Uani 1 1 d . . . . .
H15_6 H 0.0003 0.3468 0.8348 0.025 Uiso 1 1 calc R . . . .
N21_7 N 0.71919(13) 0.35669(7) 0.44879(7) 0.0165(4) Uani 1 1 d . . . . .
H21_7 H 0.7563 0.3776 0.4616 0.020 Uiso 1 1 calc R . . . .
N22_7 N 0.60878(13) 0.30978(7) 0.43906(7) 0.0157(4) Uani 1 1 d . . . . .
H22_7 H 0.5610 0.2947 0.4443 0.019 Uiso 1 1 calc R . . . .
C21_7 C 0.64925(15) 0.34116(8) 0.46896(9) 0.0144(5) Uani 1 1 d . . . . .
H21A_7 H 0.6313 0.3509 0.4996 0.017 Uiso 1 1 calc R . . . .
C22_7 C 0.65453(18) 0.30502(10) 0.39850(10) 0.0235(6) Uani 1 1 d . . . . .
H22A_7 H 0.6406 0.2849 0.3713 0.028 Uiso 1 1 calc R . . . .
C23_7 C 0.72313(17) 0.33437(10) 0.40450(10) 0.0230(6) Uani 1 1 d . . . . .
H23_7 H 0.7661 0.3388 0.3822 0.028 Uiso 1 1 calc R . . . .
N21_8 N -0.40107(13) 0.52209(7) 0.92660(7) 0.0141(4) Uani 1 1 d . . . . .
H21_8 H -0.4500 0.5365 0.9311 0.017 Uiso 1 1 calc R . . . .
N22_8 N -0.28776(13) 0.47722(7) 0.93853(7) 0.0151(4) Uani 1 1 d . . . . .
H22_8 H -0.2496 0.4571 0.9521 0.018 Uiso 1 1 calc R . . . .
C21_8 C -0.35973(15) 0.49161(8) 0.95749(8) 0.0137(5) Uani 1 1 d . . . . .
H21A_8 H -0.3784 0.4818 0.9880 0.016 Uiso 1 1 calc R . . . .
C22_8 C -0.35420(16) 0.52721(9) 0.88648(9) 0.0181(5) Uani 1 1 d . . . . .
H22A_8 H -0.3688 0.5467 0.8588 0.022 Uiso 1 1 calc R . . . .
C23_8 C -0.28338(17) 0.49928(9) 0.89400(9) 0.0192(5) Uani 1 1 d . . . . .
H23_8 H -0.2389 0.4956 0.8726 0.023 Uiso 1 1 calc R . . . .
N21_9 N 0.21993(13) 0.31023(7) 0.45043(7) 0.0149(4) Uani 1 1 d . . . . .
H21_9 H 0.2570 0.2899 0.4646 0.018 Uiso 1 1 calc R . . . .
N22_9 N 0.10917(13) 0.35656(7) 0.43738(7) 0.0152(4) Uani 1 1 d . . . . .
H22_9 H 0.0610 0.3718 0.4415 0.018 Uiso 1 1 calc R . . . .
C21_9 C 0.15574(17) 0.35980(9) 0.39674(9) 0.0200(5) Uani 1 1 d . . . . .
H21A_9 H 0.1420 0.3788 0.3685 0.024 Uiso 1 1 calc R . . . .
C22_9 C 0.14937(15) 0.32661(8) 0.46915(9) 0.0135(5) Uani 1 1 d . . . . .
H22A_9 H 0.1308 0.3182 0.5002 0.016 Uiso 1 1 calc R . . . .
C23_9 C 0.22464(17) 0.33072(9) 0.40486(10) 0.0217(5) Uani 1 1 d . . . . .
H23_9 H 0.2682 0.3254 0.3832 0.026 Uiso 1 1 calc R . . . .
N21_10 N 0.30055(13) 0.31460(7) 0.57669(8) 0.0166(4) Uani 1 1 d . . . . .
H21_10 H 0.2628 0.2937 0.5648 0.020 Uiso 1 1 calc R . . . .
N22_10 N 0.41372(13) 0.35940(7) 0.58510(7) 0.0162(4) Uani 1 1 d . . . . .
H22_10 H 0.4631 0.3730 0.5796 0.019 Uiso 1 1 calc R . . . .
C21_10 C 0.37267(15) 0.32713(8) 0.55710(9) 0.0149(5) Uani 1 1 d . . . . .
H21A_10 H 0.3918 0.3150 0.5278 0.018 Uiso 1 1 calc R . . . .
C22_10 C 0.29509(19) 0.34011(10) 0.61887(10) 0.0268(6) Uani 1 1 d . . . . .
H22A_10 H 0.2500 0.3384 0.6402 0.032 Uiso 1 1 calc R . . . .
C23_10 C 0.36595(19) 0.36803(10) 0.62412(10) 0.0285(6) Uani 1 1 d . . . . .
H23_10 H 0.3801 0.3895 0.6499 0.034 Uiso 1 1 calc R . . . .
N21_11 N 0.90837(13) 0.31113(7) 0.58424(7) 0.0136(4) Uani 1 1 d . . . . .
H21_11 H 0.9572 0.2967 0.5795 0.016 Uiso 1 1 calc R . . . .
N22_11 N 0.79656(13) 0.35699(7) 0.57341(7) 0.0144(4) Uani 1 1 d . . . . .
H22_11 H 0.7595 0.3779 0.5605 0.017 Uiso 1 1 calc R . . . .
C21_11 C 0.86879(15) 0.34279(8) 0.55446(8) 0.0128(5) Uani 1 1 d . . . . .
H21A_11 H 0.8887 0.3535 0.5247 0.015 Uiso 1 1 calc R . . . .
C22_11 C 0.86013(16) 0.30466(9) 0.62369(9) 0.0179(5) Uani 1 1 d . . . . .
H22A_11 H 0.8734 0.2841 0.6505 0.021 Uiso 1 1 calc R . . . .
C23_11 C 0.79024(16) 0.33327(9) 0.61666(9) 0.0174(5) Uani 1 1 d . . . . .
H23_11 H 0.7450 0.3364 0.6377 0.021 Uiso 1 1 calc R . . . .
N21_12 N 0.09464(14) 0.47409(7) 0.92752(8) 0.0184(4) Uani 1 1 d . . . . .
H21_12 H 0.0460 0.4604 0.9339 0.022 Uiso 1 1 calc R . . . .
N22_12 N 0.20744(14) 0.51919(7) 0.93382(8) 0.0191(4) Uani 1 1 d . . . . .
H22_12 H 0.2455 0.5403 0.9450 0.023 Uiso 1 1 calc R . . . .
C21_12 C 0.13680(16) 0.50651(8) 0.95484(9) 0.0175(5) Uani 1 1 d . . . . .
H21A_12 H 0.1193 0.5187 0.9846 0.021 Uiso 1 1 calc R . . . .
C22_12 C 0.1401(2) 0.46559(11) 0.88754(10) 0.0304(7) Uani 1 1 d . . . . .
H22A_12 H 0.1247 0.4441 0.8620 0.037 Uiso 1 1 calc R . . . .
C23_12 C 0.2106(2) 0.49358(11) 0.89149(10) 0.0310(7) Uani 1 1 d . . . . .
H23_12 H 0.2542 0.4953 0.8693 0.037 Uiso 1 1 calc R . . . .
O32_13 O 0.73421(13) 0.25134(7) 0.76540(7) 0.0268(4) Uani 1 1 d . . . . .
O31_13 O 0.80552(14) 0.31141(8) 0.74015(8) 0.0347(5) Uani 1 1 d . . . . .
C32_13 C 0.78753(17) 0.28676(10) 0.77313(10) 0.0251(6) Uani 1 1 d . . . . .
C33_13 C 0.82421(19) 0.29122(12) 0.82759(11) 0.0329(7) Uani 1 1 d . . . . .
H33A_13 H 0.7842 0.2763 0.8481 0.049 Uiso 1 1 calc GR . . . .
H33B_13 H 0.8290 0.3229 0.8366 0.049 Uiso 1 1 calc GR . . . .
H33C_13 H 0.8833 0.2774 0.8336 0.049 Uiso 1 1 calc GR . . . .
C31_13 C 0.6982(2) 0.24224(11) 0.71328(11) 0.0321(7) Uani 1 1 d . . . . .
H31A_13 H 0.7467 0.2339 0.6938 0.038 Uiso 1 1 calc R . . . .
H31B_13 H 0.6677 0.2690 0.6978 0.038 Uiso 1 1 calc R . . . .
C34_13 C 0.6335(3) 0.20448(14) 0.71368(13) 0.0505(10) Uani 1 1 d . . . . .
H34A_13 H 0.6115 0.1958 0.6792 0.076 Uiso 1 1 calc GR . . . .
H34B_13 H 0.5833 0.2139 0.7307 0.076 Uiso 1 1 calc GR . . . .
H34C_13 H 0.6634 0.1789 0.7314 0.076 Uiso 1 1 calc GR . . . .
O32_14 O -0.23491(12) 0.58188(7) 0.74190(7) 0.0261(4) Uani 1 1 d . . . . .
O31_14 O -0.30489(14) 0.52139(8) 0.76650(8) 0.0382(5) Uani 1 1 d . . . . .
C32_14 C -0.28766(17) 0.54596(10) 0.73346(10) 0.0250(6) Uani 1 1 d . . . . .
C33_14 C -0.1998(2) 0.59064(11) 0.79371(10) 0.0317(7) Uani 1 1 d . . . . .
H33A_14 H -0.1684 0.5640 0.8089 0.038 Uiso 1 1 calc R . . . .
H33B_14 H -0.2487 0.5983 0.8132 0.038 Uiso 1 1 calc R . . . .
C31_14 C -0.3232(2) 0.54143(11) 0.67904(11) 0.0333(7) Uani 1 1 d . . . . .
H31A_14 H -0.3829 0.5546 0.6728 0.050 Uiso 1 1 calc GR . . . .
H31B_14 H -0.3264 0.5097 0.6699 0.050 Uiso 1 1 calc GR . . . .
H31C_14 H -0.2836 0.5570 0.6588 0.050 Uiso 1 1 calc GR . . . .
C34_14 C -0.1362(2) 0.62914(14) 0.79367(13) 0.0495(10) Uani 1 1 d . . . . .
H34A_14 H -0.1665 0.6544 0.7755 0.074 Uiso 1 1 calc GR . . . .
H34B_14 H -0.0850 0.6201 0.7772 0.074 Uiso 1 1 calc GR . . . .
H34C_14 H -0.1154 0.6381 0.8282 0.074 Uiso 1 1 calc GR . . . .
O31A_15 O 0.3397(4) 0.3746(2) 0.73295(17) 0.0681(17) Uani 0.554(4) 1 d . . P C
1
O32A_15 O 0.2530(6) 0.4208(3) 0.7652(2) 0.0460(13) Uani 0.554(4) 1 d . . P C 1
C33A_15 C 0.2008(5) 0.4264(2) 0.7154(2) 0.0438(16) Uani 0.554(4) 1 d . . P C 1
H33A_15 H 0.2370 0.4420 0.6927 0.053 Uiso 0.554(4) 1 calc R . P C 1
H33B_15 H 0.1833 0.3968 0.7008 0.053 Uiso 0.554(4) 1 calc R . P C 1
C31A_15 C 0.3711(5) 0.3957(3) 0.8192(3) 0.053(2) Uani 0.554(4) 1 d . . P C 1
H31A_15 H 0.4033 0.3674 0.8251 0.079 Uiso 0.554(4) 1 calc GR . P C 1
H31B_15 H 0.3295 0.3992 0.8439 0.079 Uiso 0.554(4) 1 calc GR . P C 1
H31C_15 H 0.4138 0.4205 0.8224 0.079 Uiso 0.554(4) 1 calc GR . P C 1
C34A_15 C 0.1212(5) 0.4528(3) 0.7213(3) 0.071(3) Uani 0.554(4) 1 d . . P C 1
H34A_15 H 0.0840 0.4557 0.6888 0.106 Uiso 0.554(4) 1 calc GR . P C 1
H34B_15 H 0.1391 0.4825 0.7341 0.106 Uiso 0.554(4) 1 calc GR . P C 1
H34C_15 H 0.0871 0.4377 0.7449 0.106 Uiso 0.554(4) 1 calc GR . P C 1
C32A_15 C 0.3211(5) 0.3957(2) 0.7684(2) 0.0416(16) Uani 0.554(4) 1 d . . P C 1
O31_15 O 0.1584(4) 0.4595(2) 0.7782(2) 0.060(2) Uani 0.446(4) 1 d . . P C 2
O32_15 O 0.2454(7) 0.4124(4) 0.7465(3) 0.0460(13) Uani 0.446(4) 1 d . . P C 2
C33_15 C 0.3003(5) 0.4083(3) 0.7963(3) 0.0385(18) Uani 0.446(4) 1 d . . P C 2
H33C_15 H 0.2664 0.3924 0.8198 0.046 Uiso 0.446(4) 1 calc R . P C 2
H33D_15 H 0.3158 0.4384 0.8101 0.046 Uiso 0.446(4) 1 calc R . P C 2
C31_15 C 0.1277(6) 0.4375(4) 0.6922(3) 0.055(3) Uani 0.446(4) 1 d . . P C 2
H31D_15 H 0.1696 0.4299 0.6688 0.083 Uiso 0.446(4) 1 calc GR . P C 2
H31E_15 H 0.1032 0.4674 0.6845 0.083 Uiso 0.446(4) 1 calc GR . P C 2
H31F_15 H 0.0792 0.4157 0.6892 0.083 Uiso 0.446(4) 1 calc GR . P C 2
C34_15 C 0.3834(6) 0.3829(3) 0.7900(4) 0.053(2) Uani 0.446(4) 1 d . . P C 2
H34D_15 H 0.3673 0.3544 0.7735 0.079 Uiso 0.446(4) 1 calc GR . P C 2
H34E_15 H 0.4175 0.3774 0.8230 0.079 Uiso 0.446(4) 1 calc GR . P C 2
H34F_15 H 0.4196 0.4004 0.7695 0.079 Uiso 0.446(4) 1 calc GR . P C 2
C32_15 C 0.1744(5) 0.4369(3) 0.7436(3) 0.042(2) Uani 0.446(4) 1 d . . P C 2


_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_1 C11_1 1.742(3) . ?
Cl2_1 C13_1 1.744(3) . ?
O1_1 C1_1 1.267(3) . ?
O2_1 C1_1 1.265(3) . ?
N1_1 N2_1 1.358(3) . ?
N1_1 C8_1 1.373(3) . ?
N1_1 C9_1 1.458(3) . ?
N2_1 C2_1 1.330(3) . ?
C1_1 C2_1 1.493(3) . ?
C2_1 C3_1 1.433(3) . ?
C3_1 C4_1 1.405(3) . ?
C3_1 C8_1 1.408(3) . ?
C4_1 C5_1 1.383(4) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.418(4) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.382(4) . ?
C6_1 H6_1 0.9500 . ?
C7_1 C8_1 1.405(3) . ?
C7_1 H7_1 0.9500 . ?
C9_1 C10_1 1.521(3) . ?
C9_1 H9A_1 0.9900 . ?
C9_1 H9B_1 0.9900 . ?
C10_1 C15_1 1.400(3) . ?
C10_1 C11_1 1.401(3) . ?
C11_1 C12_1 1.393(4) . ?
C12_1 C13_1 1.382(4) . ?
C12_1 H12_1 0.9500 . ?
C13_1 C14_1 1.382(4) . ?
C14_1 C15_1 1.395(3) . ?
C14_1 H14_1 0.9500 . ?
C15_1 H15_1 0.9500 . ?
Cl1_2 C13_2 1.746(2) . ?
Cl2_2 C11_2 1.754(2) . ?
O1_2 C1_2 1.262(3) . ?
O2_2 C1_2 1.266(3) . ?
N1_2 N2_2 1.361(3) . ?
N1_2 C8_2 1.372(3) . ?
N1_2 C9_2 1.455(3) . ?
N2_2 C2_2 1.331(3) . ?
C1_2 C2_2 1.495(3) . ?
C2_2 C3_2 1.432(3) . ?
C3_2 C4_2 1.407(3) . ?
C3_2 C8_2 1.413(3) . ?
C4_2 C5_2 1.384(3) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.417(4) . ?
C5_2 H5_2 0.9500 . ?
C6_2 C7_2 1.380(4) . ?
C6_2 H6_2 0.9500 . ?
C7_2 C8_2 1.405(3) . ?
C7_2 H7_2 0.9500 . ?
C9_2 C10_2 1.521(3) . ?
C9_2 H9A_2 0.9900 . ?
C9_2 H9B_2 0.9900 . ?
C10_2 C15_2 1.387(3) . ?
C10_2 C11_2 1.392(3) . ?
C11_2 C12_2 1.384(3) . ?
C12_2 C13_2 1.388(4) . ?
C12_2 H12_2 0.9500 . ?
C13_2 C14_2 1.377(4) . ?
C14_2 C15_2 1.393(3) . ?
C14_2 H14_2 0.9500 . ?
C15_2 H15_2 0.9500 . ?
Cl1_3 C11_3 1.743(3) . ?
Cl2_3 C13_3 1.749(3) . ?
O1_3 C1_3 1.259(3) . ?
O2_3 C1_3 1.270(3) . ?
N1_3 N2_3 1.362(3) . ?
N1_3 C8_3 1.370(3) . ?
N1_3 C9_3 1.459(3) . ?
N2_3 C2_3 1.335(3) . ?
C13_3 C14_3 1.380(4) . ?
C13_3 C12_3 1.384(4) . ?
C1_3 C2_3 1.493(3) . ?
C2_3 C3_3 1.428(3) . ?
C3_3 C8_3 1.409(3) . ?
C3_3 C4_3 1.411(3) . ?
C4_3 C5_3 1.379(4) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.421(4) . ?
C5_3 H5_3 0.9500 . ?
C6_3 C7_3 1.384(4) . ?
C6_3 H6_3 0.9500 . ?
C7_3 C8_3 1.404(3) . ?
C7_3 H7_3 0.9500 . ?
C9_3 C10_3 1.519(3) . ?
C9_3 H9A_3 0.9900 . ?
C9_3 H9B_3 0.9900 . ?
C10_3 C11_3 1.389(3) . ?
C10_3 C15_3 1.410(3) . ?
C11_3 C12_3 1.394(3) . ?
C12_3 H12_3 0.9500 . ?
C14_3 C15_3 1.393(3) . ?
C14_3 H14_3 0.9500 . ?
C15_3 H15_3 0.9500 . ?
Cl1_4 C11_4 1.757(4) . ?
Cl1A_4 C11A_4 1.690(4) . ?
Cl2_4 C13_4 1.7457(18) . ?
O1_4 C1_4 1.266(3) . ?
O2_4 C1_4 1.262(3) . ?
N1_4 N2_4 1.359(3) . ?
N1_4 C8_4 1.372(3) . ?
N1_4 C9_4 1.449(3) . ?
N2_4 C2_4 1.330(3) . ?
C1_4 C2_4 1.496(3) . ?
C2_4 C3_4 1.431(3) . ?
C3_4 C8_4 1.410(3) . ?
C3_4 C4_4 1.411(3) . ?
C4_4 C5_4 1.387(4) . ?
C4_4 H4_4 0.9500 . ?
C5_4 C6_4 1.420(4) . ?
C5_4 H5_4 0.9500 . ?
C6_4 C7_4 1.384(4) . ?
C6_4 H6_4 0.9500 . ?
C7_4 C8_4 1.410(3) . ?
C7_4 H7_4 0.9500 . ?
C9_4 C10_4 1.532(3) . ?
C9_4 H9A_4 0.9900 . ?
C9_4 H9B_4 0.9900 . ?
C10_4 C11_4 1.384(4) . ?
C10_4 C11A_4 1.3900 . ?
C10_4 C15A_4 1.3900 . ?
C10_4 C15_4 1.401(4) . ?
C11A_4 C12A_4 1.3900 . ?
C12A_4 C13_4 1.3900 . ?
C12A_4 H12A_4 0.9500 . ?
C13_4 C14_4 1.383(5) . ?
C13_4 C14A_4 1.3900 . ?
C13_4 C12_4 1.391(5) . ?
C14A_4 C15A_4 1.3900 . ?
C14A_4 H14A_4 0.9500 . ?
C15A_4 H15A_4 0.9500 . ?
C11_4 C12_4 1.388(5) . ?
C12_4 H12_4 0.9500 . ?
C14_4 C15_4 1.385(4) . ?
C14_4 H14_4 0.9500 . ?
C15_4 H15_4 0.9500 . ?
Cl1_5 C11_5 1.763(4) . ?
Cl1A_5 C11A_5 1.679(5) . ?
Cl2_5 C13_5 1.7448(18) . ?
O1_5 C1_5 1.266(3) . ?
O2_5 C1_5 1.262(3) . ?
N1_5 N2_5 1.359(3) . ?
N1_5 C8_5 1.369(3) . ?
N1_5 C9_5 1.453(3) . ?
N2_5 C2_5 1.329(3) . ?
C1_5 C2_5 1.495(3) . ?
C2_5 C3_5 1.433(3) . ?
C3_5 C4_5 1.407(3) . ?
C3_5 C8_5 1.415(3) . ?
C4_5 C5_5 1.386(4) . ?
C4_5 H4_5 0.9500 . ?
C5_5 C6_5 1.420(4) . ?
C5_5 H5_5 0.9500 . ?
C6_5 C7_5 1.381(4) . ?
C6_5 H6_5 0.9500 . ?
C7_5 C8_5 1.408(3) . ?
C7_5 H7_5 0.9500 . ?
C9_5 C10_5 1.530(3) . ?
C9_5 H9A_5 0.9900 . ?
C9_5 H9B_5 0.9900 . ?
C10_5 C11_5 1.378(4) . ?
C10_5 C11A_5 1.3900 . ?
C10_5 C15A_5 1.3900 . ?
C10_5 C15_5 1.405(4) . ?
C11A_5 C12A_5 1.3900 . ?
C12A_5 C13_5 1.3900 . ?
C12A_5 H12A_5 0.9500 . ?
C13_5 C14_5 1.379(5) . ?
C13_5 C12_5 1.385(5) . ?
C13_5 C14A_5 1.3900 . ?
C14A_5 C15A_5 1.3900 . ?
C14A_5 H14A_5 0.9500 . ?
C15A_5 H15A_5 0.9500 . ?
C11_5 C12_5 1.390(5) . ?
C12_5 H12_5 0.9500 . ?
C14_5 C15_5 1.388(4) . ?
C14_5 H14_5 0.9500 . ?
C15_5 H15_5 0.9500 . ?
Cl1_6 C11_6 1.744(2) . ?
Cl2_6 C13_6 1.744(2) . ?
O1_6 C1_6 1.262(3) . ?
O2_6 C1_6 1.269(3) . ?
N1_6 N2_6 1.357(3) . ?
N1_6 C8_6 1.374(3) . ?
N1_6 C9_6 1.454(3) . ?
N2_6 C2_6 1.337(3) . ?
C1_6 C2_6 1.488(3) . ?
C2_6 C3_6 1.429(3) . ?
C3_6 C8_6 1.409(3) . ?
C3_6 C4_6 1.413(3) . ?
C4_6 C5_6 1.382(3) . ?
C4_6 H4_6 0.9500 . ?
C5_6 C6_6 1.419(4) . ?
C5_6 H5_6 0.9500 . ?
C6_6 C7_6 1.379(4) . ?
C6_6 H6_6 0.9500 . ?
C7_6 C8_6 1.409(3) . ?
C7_6 H7_6 0.9500 . ?
C9_6 C10_6 1.520(3) . ?
C9_6 H9A_6 0.9900 . ?
C9_6 H9B_6 0.9900 . ?
C10_6 C15_6 1.393(3) . ?
C10_6 C11_6 1.394(3) . ?
C11_6 C12_6 1.387(3) . ?
C12_6 C13_6 1.390(3) . ?
C12_6 H12_6 0.9500 . ?
C13_6 C14_6 1.382(3) . ?
C14_6 C15_6 1.395(3) . ?
C14_6 H14_6 0.9500 . ?
C15_6 H15_6 0.9500 . ?
N21_7 C21_7 1.336(3) . ?
N21_7 C23_7 1.376(3) . ?
N21_7 H21_7 0.8800 . ?
N22_7 C21_7 1.333(3) . ?
N22_7 C22_7 1.377(3) . ?
N22_7 H22_7 0.8800 . ?
C21_7 H21A_7 0.9500 . ?
C22_7 C23_7 1.354(4) . ?
C22_7 H22A_7 0.9500 . ?
C23_7 H23_7 0.9500 . ?
N21_8 C21_8 1.334(3) . ?
N21_8 C22_8 1.378(3) . ?
N21_8 H21_8 0.8800 . ?
N22_8 C21_8 1.335(3) . ?
N22_8 C23_8 1.379(3) . ?
N22_8 H22_8 0.8800 . ?
C21_8 H21A_8 0.9500 . ?
C22_8 C23_8 1.354(4) . ?
C22_8 H22A_8 0.9500 . ?
C23_8 H23_8 0.9500 . ?
N21_9 C22_9 1.334(3) . ?
N21_9 C23_9 1.383(3) . ?
N21_9 H21_9 0.8800 . ?
N22_9 C22_9 1.330(3) . ?
N22_9 C21_9 1.382(3) . ?
N22_9 H22_9 0.8800 . ?
C21_9 C23_9 1.354(4) . ?
C21_9 H21A_9 0.9500 . ?
C22_9 H22A_9 0.9500 . ?
C23_9 H23_9 0.9500 . ?
N21_10 C21_10 1.328(3) . ?
N21_10 C22_10 1.381(3) . ?
N21_10 H21_10 0.8800 . ?
N22_10 C21_10 1.328(3) . ?
N22_10 C23_10 1.377(3) . ?
N22_10 H22_10 0.8800 . ?
C21_10 H21A_10 0.9500 . ?
C22_10 C23_10 1.353(4) . ?
C22_10 H22A_10 0.9500 . ?
C23_10 H23_10 0.9500 . ?
N21_11 C21_11 1.332(3) . ?
N21_11 C22_11 1.381(3) . ?
N21_11 H21_11 0.8800 . ?
N22_11 C21_11 1.336(3) . ?
N22_11 C23_11 1.379(3) . ?
N22_11 H22_11 0.8800 . ?
C21_11 H21A_11 0.9500 . ?
C22_11 C23_11 1.355(4) . ?
C22_11 H22A_11 0.9500 . ?
C23_11 H23_11 0.9500 . ?
N21_12 C21_12 1.329(3) . ?
N21_12 C22_12 1.376(3) . ?
N21_12 H21_12 0.8800 . ?
N22_12 C21_12 1.330(3) . ?
N22_12 C23_12 1.380(4) . ?
N22_12 H22_12 0.8800 . ?
C21_12 H21A_12 0.9500 . ?
C22_12 C23_12 1.350(4) . ?
C22_12 H22A_12 0.9500 . ?
C23_12 H23_12 0.9500 . ?
O32_13 C32_13 1.332(3) . ?
O32_13 C31_13 1.463(3) . ?
O31_13 C32_13 1.214(3) . ?
C32_13 C33_13 1.504(4) . ?
C33_13 H33A_13 0.9800 . ?
C33_13 H33B_13 0.9800 . ?
C33_13 H33C_13 0.9800 . ?
C31_13 C34_13 1.496(5) . ?
C31_13 H31A_13 0.9900 . ?
C31_13 H31B_13 0.9900 . ?
C34_13 H34A_13 0.9800 . ?
C34_13 H34B_13 0.9800 . ?
C34_13 H34C_13 0.9800 . ?
O32_14 C32_14 1.341(3) . ?
O32_14 C33_14 1.450(3) . ?
O31_14 C32_14 1.210(3) . ?
C32_14 C31_14 1.500(4) . ?
C33_14 C34_14 1.502(5) . ?
C33_14 H33A_14 0.9900 . ?
C33_14 H33B_14 0.9900 . ?
C31_14 H31A_14 0.9800 . ?
C31_14 H31B_14 0.9800 . ?
C31_14 H31C_14 0.9800 . ?
C34_14 H34A_14 0.9800 . ?
C34_14 H34B_14 0.9800 . ?
C34_14 H34C_14 0.9800 . ?
O31A_15 C32A_15 1.209(9) . ?
O32A_15 C32A_15 1.270(12) . ?
O32A_15 C33A_15 1.475(7) . ?
C33A_15 C34A_15 1.468(10) . ?
C33A_15 H33A_15 0.9900 . ?
C33A_15 H33B_15 0.9900 . ?
C31A_15 C32A_15 1.475(9) . ?
C31A_15 H31A_15 0.9800 . ?
C31A_15 H31B_15 0.9800 . ?
C31A_15 H31C_15 0.9800 . ?
C34A_15 H34A_15 0.9800 . ?
C34A_15 H34B_15 0.9800 . ?
C34A_15 H34C_15 0.9800 . ?
O31_15 C32_15 1.202(9) . ?
O32_15 C32_15 1.296(14) . ?
O32_15 C33_15 1.487(10) . ?
C33_15 C34_15 1.498(12) . ?
C33_15 H33C_15 0.9900 . ?
C33_15 H33D_15 0.9900 . ?
C31_15 C32_15 1.468(11) . ?
C31_15 H31D_15 0.9800 . ?
C31_15 H31E_15 0.9800 . ?
C31_15 H31F_15 0.9800 . ?
C34_15 H34D_15 0.9800 . ?
C34_15 H34E_15 0.9800 . ?
C34_15 H34F_15 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2_1 N1_1 C8_1 111.90(18) . . ?
N2_1 N1_1 C9_1 119.79(19) . . ?
C8_1 N1_1 C9_1 128.3(2) . . ?
C2_1 N2_1 N1_1 106.27(19) . . ?
O2_1 C1_1 O1_1 124.7(2) . . ?
O2_1 C1_1 C2_1 116.8(2) . . ?
O1_1 C1_1 C2_1 118.5(2) . . ?
N2_1 C2_1 C3_1 111.1(2) . . ?
N2_1 C2_1 C1_1 119.6(2) . . ?
C3_1 C2_1 C1_1 129.1(2) . . ?
C4_1 C3_1 C8_1 119.7(2) . . ?
C4_1 C3_1 C2_1 136.0(2) . . ?
C8_1 C3_1 C2_1 104.2(2) . . ?
C5_1 C4_1 C3_1 118.3(2) . . ?
C5_1 C4_1 H4_1 120.9 . . ?
C3_1 C4_1 H4_1 120.9 . . ?
C4_1 C5_1 C6_1 121.1(2) . . ?
C4_1 C5_1 H5_1 119.4 . . ?
C6_1 C5_1 H5_1 119.4 . . ?
C7_1 C6_1 C5_1 121.7(2) . . ?
C7_1 C6_1 H6_1 119.2 . . ?
C5_1 C6_1 H6_1 119.2 . . ?
C6_1 C7_1 C8_1 116.7(2) . . ?
C6_1 C7_1 H7_1 121.6 . . ?
C8_1 C7_1 H7_1 121.6 . . ?
N1_1 C8_1 C7_1 131.1(2) . . ?
N1_1 C8_1 C3_1 106.5(2) . . ?
C7_1 C8_1 C3_1 122.4(2) . . ?
N1_1 C9_1 C10_1 114.74(19) . . ?
N1_1 C9_1 H9A_1 108.6 . . ?
C10_1 C9_1 H9A_1 108.6 . . ?
N1_1 C9_1 H9B_1 108.6 . . ?
C10_1 C9_1 H9B_1 108.6 . . ?
H9A_1 C9_1 H9B_1 107.6 . . ?
C15_1 C10_1 C11_1 116.8(2) . . ?
C15_1 C10_1 C9_1 118.4(2) . . ?
C11_1 C10_1 C9_1 124.8(2) . . ?
C12_1 C11_1 C10_1 122.1(2) . . ?
C12_1 C11_1 Cl1_1 117.1(2) . . ?
C10_1 C11_1 Cl1_1 120.83(19) . . ?
C13_1 C12_1 C11_1 118.7(2) . . ?
C13_1 C12_1 H12_1 120.7 . . ?
C11_1 C12_1 H12_1 120.7 . . ?
C12_1 C13_1 C14_1 121.7(2) . . ?
C12_1 C13_1 Cl2_1 117.7(2) . . ?
C14_1 C13_1 Cl2_1 120.6(2) . . ?
C13_1 C14_1 C15_1 118.4(2) . . ?
C13_1 C14_1 H14_1 120.8 . . ?
C15_1 C14_1 H14_1 120.8 . . ?
C14_1 C15_1 C10_1 122.3(2) . . ?
C14_1 C15_1 H15_1 118.9 . . ?
C10_1 C15_1 H15_1 118.9 . . ?
N2_2 N1_2 C8_2 111.77(18) . . ?
N2_2 N1_2 C9_2 120.07(19) . . ?
C8_2 N1_2 C9_2 127.9(2) . . ?
C2_2 N2_2 N1_2 106.37(19) . . ?
O1_2 C1_2 O2_2 125.1(2) . . ?
O1_2 C1_2 C2_2 118.8(2) . . ?
O2_2 C1_2 C2_2 116.0(2) . . ?
N2_2 C2_2 C3_2 111.2(2) . . ?
N2_2 C2_2 C1_2 120.4(2) . . ?
C3_2 C2_2 C1_2 128.4(2) . . ?
C4_2 C3_2 C8_2 119.5(2) . . ?
C4_2 C3_2 C2_2 136.4(2) . . ?
C8_2 C3_2 C2_2 104.2(2) . . ?
C5_2 C4_2 C3_2 118.2(2) . . ?
C5_2 C4_2 H4_2 120.9 . . ?
C3_2 C4_2 H4_2 120.9 . . ?
C4_2 C5_2 C6_2 121.5(2) . . ?
C4_2 C5_2 H5_2 119.3 . . ?
C6_2 C5_2 H5_2 119.3 . . ?
C7_2 C6_2 C5_2 121.5(2) . . ?
C7_2 C6_2 H6_2 119.2 . . ?
C5_2 C6_2 H6_2 119.2 . . ?
C6_2 C7_2 C8_2 116.8(2) . . ?
C6_2 C7_2 H7_2 121.6 . . ?
C8_2 C7_2 H7_2 121.6 . . ?
N1_2 C8_2 C7_2 131.0(2) . . ?
N1_2 C8_2 C3_2 106.5(2) . . ?
C7_2 C8_2 C3_2 122.5(2) . . ?
N1_2 C9_2 C10_2 112.65(18) . . ?
N1_2 C9_2 H9A_2 109.1 . . ?
C10_2 C9_2 H9A_2 109.1 . . ?
N1_2 C9_2 H9B_2 109.1 . . ?
C10_2 C9_2 H9B_2 109.1 . . ?
H9A_2 C9_2 H9B_2 107.8 . . ?
C15_2 C10_2 C11_2 117.0(2) . . ?
C15_2 C10_2 C9_2 121.8(2) . . ?
C11_2 C10_2 C9_2 121.2(2) . . ?
C12_2 C11_2 C10_2 122.7(2) . . ?
C12_2 C11_2 Cl2_2 117.86(19) . . ?
C10_2 C11_2 Cl2_2 119.45(18) . . ?
C11_2 C12_2 C13_2 118.3(2) . . ?
C11_2 C12_2 H12_2 120.9 . . ?
C13_2 C12_2 H12_2 120.9 . . ?
C14_2 C13_2 C12_2 121.3(2) . . ?
C14_2 C13_2 Cl1_2 120.13(19) . . ?
C12_2 C13_2 Cl1_2 118.62(19) . . ?
C13_2 C14_2 C15_2 118.8(2) . . ?
C13_2 C14_2 H14_2 120.6 . . ?
C15_2 C14_2 H14_2 120.6 . . ?
C10_2 C15_2 C14_2 122.0(2) . . ?
C10_2 C15_2 H15_2 119.0 . . ?
C14_2 C15_2 H15_2 119.0 . . ?
N2_3 N1_3 C8_3 111.81(18) . . ?
N2_3 N1_3 C9_3 119.71(19) . . ?
C8_3 N1_3 C9_3 128.5(2) . . ?
C2_3 N2_3 N1_3 106.23(19) . . ?
C14_3 C13_3 C12_3 122.2(2) . . ?
C14_3 C13_3 Cl2_3 120.0(2) . . ?
C12_3 C13_3 Cl2_3 117.8(2) . . ?
O1_3 C1_3 O2_3 124.9(2) . . ?
O1_3 C1_3 C2_3 119.0(2) . . ?
O2_3 C1_3 C2_3 116.1(2) . . ?
N2_3 C2_3 C3_3 110.9(2) . . ?
N2_3 C2_3 C1_3 119.5(2) . . ?
C3_3 C2_3 C1_3 129.4(2) . . ?
C8_3 C3_3 C4_3 119.8(2) . . ?
C8_3 C3_3 C2_3 104.6(2) . . ?
C4_3 C3_3 C2_3 135.6(2) . . ?
C5_3 C4_3 C3_3 118.1(2) . . ?
C5_3 C4_3 H4_3 121.0 . . ?
C3_3 C4_3 H4_3 121.0 . . ?
C4_3 C5_3 C6_3 121.4(2) . . ?
C4_3 C5_3 H5_3 119.3 . . ?
C6_3 C5_3 H5_3 119.3 . . ?
C7_3 C6_3 C5_3 121.4(2) . . ?
C7_3 C6_3 H6_3 119.3 . . ?
C5_3 C6_3 H6_3 119.3 . . ?
C6_3 C7_3 C8_3 116.8(2) . . ?
C6_3 C7_3 H7_3 121.6 . . ?
C8_3 C7_3 H7_3 121.6 . . ?
N1_3 C8_3 C7_3 131.1(2) . . ?
N1_3 C8_3 C3_3 106.4(2) . . ?
C7_3 C8_3 C3_3 122.5(2) . . ?
N1_3 C9_3 C10_3 114.43(18) . . ?
N1_3 C9_3 H9A_3 108.7 . . ?
C10_3 C9_3 H9A_3 108.7 . . ?
N1_3 C9_3 H9B_3 108.7 . . ?
C10_3 C9_3 H9B_3 108.7 . . ?
H9A_3 C9_3 H9B_3 107.6 . . ?
C11_3 C10_3 C15_3 116.9(2) . . ?
C11_3 C10_3 C9_3 124.4(2) . . ?
C15_3 C10_3 C9_3 118.7(2) . . ?
C10_3 C11_3 C12_3 122.3(2) . . ?
C10_3 C11_3 Cl1_3 120.35(19) . . ?
C12_3 C11_3 Cl1_3 117.3(2) . . ?
C13_3 C12_3 C11_3 118.3(2) . . ?
C13_3 C12_3 H12_3 120.9 . . ?
C11_3 C12_3 H12_3 120.9 . . ?
C13_3 C14_3 C15_3 118.0(2) . . ?
C13_3 C14_3 H14_3 121.0 . . ?
C15_3 C14_3 H14_3 121.0 . . ?
C14_3 C15_3 C10_3 122.2(2) . . ?
C14_3 C15_3 H15_3 118.9 . . ?
C10_3 C15_3 H15_3 118.9 . . ?
N2_4 N1_4 C8_4 111.62(18) . . ?
N2_4 N1_4 C9_4 119.69(19) . . ?
C8_4 N1_4 C9_4 128.3(2) . . ?
C2_4 N2_4 N1_4 106.68(19) . . ?
O2_4 C1_4 O1_4 125.0(2) . . ?
O2_4 C1_4 C2_4 116.7(2) . . ?
O1_4 C1_4 C2_4 118.3(2) . . ?
N2_4 C2_4 C3_4 110.7(2) . . ?
N2_4 C2_4 C1_4 119.1(2) . . ?
C3_4 C2_4 C1_4 130.1(2) . . ?
C8_4 C3_4 C4_4 119.8(2) . . ?
C8_4 C3_4 C2_4 104.5(2) . . ?
C4_4 C3_4 C2_4 135.6(2) . . ?
C5_4 C4_4 C3_4 117.9(2) . . ?
C5_4 C4_4 H4_4 121.1 . . ?
C3_4 C4_4 H4_4 121.1 . . ?
C4_4 C5_4 C6_4 121.6(2) . . ?
C4_4 C5_4 H5_4 119.2 . . ?
C6_4 C5_4 H5_4 119.2 . . ?
C7_4 C6_4 C5_4 121.5(2) . . ?
C7_4 C6_4 H6_4 119.3 . . ?
C5_4 C6_4 H6_4 119.3 . . ?
C6_4 C7_4 C8_4 116.8(2) . . ?
C6_4 C7_4 H7_4 121.6 . . ?
C8_4 C7_4 H7_4 121.6 . . ?
N1_4 C8_4 C3_4 106.4(2) . . ?
N1_4 C8_4 C7_4 131.1(2) . . ?
C3_4 C8_4 C7_4 122.5(2) . . ?
N1_4 C9_4 C10_4 112.68(19) . . ?
N1_4 C9_4 H9A_4 109.1 . . ?
C10_4 C9_4 H9A_4 109.1 . . ?
N1_4 C9_4 H9B_4 109.1 . . ?
C10_4 C9_4 H9B_4 109.1 . . ?
H9A_4 C9_4 H9B_4 107.8 . . ?
C11A_4 C10_4 C15A_4 120.0 . . ?
C11_4 C10_4 C15_4 117.8(2) . . ?
C11_4 C10_4 C9_4 121.1(2) . . ?
C11A_4 C10_4 C9_4 120.60(18) . . ?
C15A_4 C10_4 C9_4 119.39(18) . . ?
C15_4 C10_4 C9_4 120.9(2) . . ?
C10_4 C11A_4 C12A_4 120.0 . . ?
C10_4 C11A_4 Cl1A_4 124.2(2) . . ?
C12A_4 C11A_4 Cl1A_4 115.6(2) . . ?
C13_4 C12A_4 C11A_4 120.0 . . ?
C13_4 C12A_4 H12A_4 120.0 . . ?
C11A_4 C12A_4 H12A_4 120.0 . . ?
C12A_4 C13_4 C14A_4 120.0 . . ?
C14_4 C13_4 C12_4 121.7(3) . . ?
C14_4 C13_4 Cl2_4 120.1(2) . . ?
C12A_4 C13_4 Cl2_4 118.66(16) . . ?
C14A_4 C13_4 Cl2_4 121.33(16) . . ?
C12_4 C13_4 Cl2_4 118.2(2) . . ?
C15A_4 C14A_4 C13_4 120.0 . . ?
C15A_4 C14A_4 H14A_4 120.0 . . ?
C13_4 C14A_4 H14A_4 120.0 . . ?
C14A_4 C15A_4 C10_4 120.0 . . ?
C14A_4 C15A_4 H15A_4 120.0 . . ?
C10_4 C15A_4 H15A_4 120.0 . . ?
C10_4 C11_4 C12_4 122.0(3) . . ?
C10_4 C11_4 Cl1_4 119.6(2) . . ?
C12_4 C11_4 Cl1_4 118.4(3) . . ?
C11_4 C12_4 C13_4 118.2(3) . . ?
C11_4 C12_4 H12_4 120.9 . . ?
C13_4 C12_4 H12_4 120.9 . . ?
C13_4 C14_4 C15_4 118.4(3) . . ?
C13_4 C14_4 H14_4 120.8 . . ?
C15_4 C14_4 H14_4 120.8 . . ?
C14_4 C15_4 C10_4 121.7(3) . . ?
C14_4 C15_4 H15_4 119.1 . . ?
C10_4 C15_4 H15_4 119.1 . . ?
N2_5 N1_5 C8_5 111.94(18) . . ?
N2_5 N1_5 C9_5 119.61(19) . . ?
C8_5 N1_5 C9_5 128.0(2) . . ?
C2_5 N2_5 N1_5 106.49(19) . . ?
O2_5 C1_5 O1_5 125.2(2) . . ?
O2_5 C1_5 C2_5 116.5(2) . . ?
O1_5 C1_5 C2_5 118.2(2) . . ?
N2_5 C2_5 C3_5 111.0(2) . . ?
N2_5 C2_5 C1_5 119.7(2) . . ?
C3_5 C2_5 C1_5 129.3(2) . . ?
C4_5 C3_5 C8_5 119.6(2) . . ?
C4_5 C3_5 C2_5 136.1(2) . . ?
C8_5 C3_5 C2_5 104.3(2) . . ?
C5_5 C4_5 C3_5 118.1(2) . . ?
C5_5 C4_5 H4_5 121.0 . . ?
C3_5 C4_5 H4_5 121.0 . . ?
C4_5 C5_5 C6_5 121.5(2) . . ?
C4_5 C5_5 H5_5 119.3 . . ?
C6_5 C5_5 H5_5 119.3 . . ?
C7_5 C6_5 C5_5 121.6(2) . . ?
C7_5 C6_5 H6_5 119.2 . . ?
C5_5 C6_5 H6_5 119.2 . . ?
C6_5 C7_5 C8_5 116.7(2) . . ?
C6_5 C7_5 H7_5 121.6 . . ?
C8_5 C7_5 H7_5 121.6 . . ?
N1_5 C8_5 C7_5 131.2(2) . . ?
N1_5 C8_5 C3_5 106.3(2) . . ?
C7_5 C8_5 C3_5 122.5(2) . . ?
N1_5 C9_5 C10_5 112.58(19) . . ?
N1_5 C9_5 H9A_5 109.1 . . ?
C10_5 C9_5 H9A_5 109.1 . . ?
N1_5 C9_5 H9B_5 109.1 . . ?
C10_5 C9_5 H9B_5 109.1 . . ?
H9A_5 C9_5 H9B_5 107.8 . . ?
C11A_5 C10_5 C15A_5 120.0 . . ?
C11_5 C10_5 C15_5 117.6(2) . . ?
C11_5 C10_5 C9_5 122.0(2) . . ?
C11A_5 C10_5 C9_5 121.03(18) . . ?
C15A_5 C10_5 C9_5 118.97(18) . . ?
C15_5 C10_5 C9_5 120.3(2) . . ?
C12A_5 C11A_5 C10_5 120.0 . . ?
C12A_5 C11A_5 Cl1A_5 114.8(2) . . ?
C10_5 C11A_5 Cl1A_5 124.6(3) . . ?
C11A_5 C12A_5 C13_5 120.0 . . ?
C11A_5 C12A_5 H12A_5 120.0 . . ?
C13_5 C12A_5 H12A_5 120.0 . . ?
C14_5 C13_5 C12_5 121.9(2) . . ?
C12A_5 C13_5 C14A_5 120.0 . . ?
C14_5 C13_5 Cl2_5 120.0(2) . . ?
C12_5 C13_5 Cl2_5 118.0(2) . . ?
C12A_5 C13_5 Cl2_5 118.73(16) . . ?
C14A_5 C13_5 Cl2_5 121.27(16) . . ?
C15A_5 C14A_5 C13_5 120.0 . . ?
C15A_5 C14A_5 H14A_5 120.0 . . ?
C13_5 C14A_5 H14A_5 120.0 . . ?
C14A_5 C15A_5 C10_5 120.0 . . ?
C14A_5 C15A_5 H15A_5 120.0 . . ?
C10_5 C15A_5 H15A_5 120.0 . . ?
C10_5 C11_5 C12_5 122.5(3) . . ?
C10_5 C11_5 Cl1_5 119.6(2) . . ?
C12_5 C11_5 Cl1_5 117.9(3) . . ?
C13_5 C12_5 C11_5 117.9(3) . . ?
C13_5 C12_5 H12_5 121.0 . . ?
C11_5 C12_5 H12_5 121.0 . . ?
C13_5 C14_5 C15_5 118.6(3) . . ?
C13_5 C14_5 H14_5 120.7 . . ?
C15_5 C14_5 H14_5 120.7 . . ?
C14_5 C15_5 C10_5 121.4(3) . . ?
C14_5 C15_5 H15_5 119.3 . . ?
C10_5 C15_5 H15_5 119.3 . . ?
N2_6 N1_6 C8_6 111.65(18) . . ?
N2_6 N1_6 C9_6 120.29(19) . . ?
C8_6 N1_6 C9_6 127.7(2) . . ?
C2_6 N2_6 N1_6 106.63(19) . . ?
O1_6 C1_6 O2_6 124.4(2) . . ?
O1_6 C1_6 C2_6 119.5(2) . . ?
O2_6 C1_6 C2_6 116.1(2) . . ?
N2_6 C2_6 C3_6 110.6(2) . . ?
N2_6 C2_6 C1_6 120.4(2) . . ?
C3_6 C2_6 C1_6 128.9(2) . . ?
C8_6 C3_6 C4_6 119.4(2) . . ?
C8_6 C3_6 C2_6 104.7(2) . . ?
C4_6 C3_6 C2_6 135.9(2) . . ?
C5_6 C4_6 C3_6 118.0(2) . . ?
C5_6 C4_6 H4_6 121.0 . . ?
C3_6 C4_6 H4_6 121.0 . . ?
C4_6 C5_6 C6_6 121.5(2) . . ?
C4_6 C5_6 H5_6 119.2 . . ?
C6_6 C5_6 H5_6 119.2 . . ?
C7_6 C6_6 C5_6 121.8(2) . . ?
C7_6 C6_6 H6_6 119.1 . . ?
C5_6 C6_6 H6_6 119.1 . . ?
C6_6 C7_6 C8_6 116.4(2) . . ?
C6_6 C7_6 H7_6 121.8 . . ?
C8_6 C7_6 H7_6 121.8 . . ?
N1_6 C8_6 C7_6 130.7(2) . . ?
N1_6 C8_6 C3_6 106.4(2) . . ?
C7_6 C8_6 C3_6 122.9(2) . . ?
N1_6 C9_6 C10_6 112.72(18) . . ?
N1_6 C9_6 H9A_6 109.0 . . ?
C10_6 C9_6 H9A_6 109.0 . . ?
N1_6 C9_6 H9B_6 109.0 . . ?
C10_6 C9_6 H9B_6 109.0 . . ?
H9A_6 C9_6 H9B_6 107.8 . . ?
C15_6 C10_6 C11_6 117.0(2) . . ?
C15_6 C10_6 C9_6 121.8(2) . . ?
C11_6 C10_6 C9_6 121.2(2) . . ?
C12_6 C11_6 C10_6 122.5(2) . . ?
C12_6 C11_6 Cl1_6 117.50(18) . . ?
C10_6 C11_6 Cl1_6 119.97(18) . . ?
C11_6 C12_6 C13_6 118.4(2) . . ?
C11_6 C12_6 H12_6 120.8 . . ?
C13_6 C12_6 H12_6 120.8 . . ?
C14_6 C13_6 C12_6 121.3(2) . . ?
C14_6 C13_6 Cl2_6 120.13(18) . . ?
C12_6 C13_6 Cl2_6 118.60(19) . . ?
C13_6 C14_6 C15_6 118.7(2) . . ?
C13_6 C14_6 H14_6 120.7 . . ?
C15_6 C14_6 H14_6 120.7 . . ?
C10_6 C15_6 C14_6 122.1(2) . . ?
C10_6 C15_6 H15_6 118.9 . . ?
C14_6 C15_6 H15_6 118.9 . . ?
C21_7 N21_7 C23_7 108.2(2) . . ?
C21_7 N21_7 H21_7 125.9 . . ?
C23_7 N21_7 H21_7 125.9 . . ?
C21_7 N22_7 C22_7 108.3(2) . . ?
C21_7 N22_7 H22_7 125.9 . . ?
C22_7 N22_7 H22_7 125.9 . . ?
N22_7 C21_7 N21_7 109.0(2) . . ?
N22_7 C21_7 H21A_7 125.5 . . ?
N21_7 C21_7 H21A_7 125.5 . . ?
C23_7 C22_7 N22_7 107.3(2) . . ?
C23_7 C22_7 H22A_7 126.4 . . ?
N22_7 C22_7 H22A_7 126.4 . . ?
C22_7 C23_7 N21_7 107.3(2) . . ?
C22_7 C23_7 H23_7 126.3 . . ?
N21_7 C23_7 H23_7 126.3 . . ?
C21_8 N21_8 C22_8 108.5(2) . . ?
C21_8 N21_8 H21_8 125.7 . . ?
C22_8 N21_8 H21_8 125.7 . . ?
C21_8 N22_8 C23_8 108.3(2) . . ?
C21_8 N22_8 H22_8 125.8 . . ?
C23_8 N22_8 H22_8 125.8 . . ?
N21_8 C21_8 N22_8 108.7(2) . . ?
N21_8 C21_8 H21A_8 125.6 . . ?
N22_8 C21_8 H21A_8 125.6 . . ?
C23_8 C22_8 N21_8 107.1(2) . . ?
C23_8 C22_8 H22A_8 126.4 . . ?
N21_8 C22_8 H22A_8 126.4 . . ?
C22_8 C23_8 N22_8 107.3(2) . . ?
C22_8 C23_8 H23_8 126.3 . . ?
N22_8 C23_8 H23_8 126.3 . . ?
C22_9 N21_9 C23_9 108.1(2) . . ?
C22_9 N21_9 H21_9 125.9 . . ?
C23_9 N21_9 H21_9 125.9 . . ?
C22_9 N22_9 C21_9 108.6(2) . . ?
C22_9 N22_9 H22_9 125.7 . . ?
C21_9 N22_9 H22_9 125.7 . . ?
C23_9 C21_9 N22_9 106.9(2) . . ?
C23_9 C21_9 H21A_9 126.6 . . ?
N22_9 C21_9 H21A_9 126.6 . . ?
N22_9 C22_9 N21_9 109.0(2) . . ?
N22_9 C22_9 H22A_9 125.5 . . ?
N21_9 C22_9 H22A_9 125.5 . . ?
C21_9 C23_9 N21_9 107.4(2) . . ?
C21_9 C23_9 H23_9 126.3 . . ?
N21_9 C23_9 H23_9 126.3 . . ?
C21_10 N21_10 C22_10 108.2(2) . . ?
C21_10 N21_10 H21_10 125.9 . . ?
C22_10 N21_10 H21_10 125.9 . . ?
C21_10 N22_10 C23_10 108.5(2) . . ?
C21_10 N22_10 H22_10 125.8 . . ?
C23_10 N22_10 H22_10 125.8 . . ?
N21_10 C21_10 N22_10 109.1(2) . . ?
N21_10 C21_10 H21A_10 125.5 . . ?
N22_10 C21_10 H21A_10 125.5 . . ?
C23_10 C22_10 N21_10 107.1(2) . . ?
C23_10 C22_10 H22A_10 126.4 . . ?
N21_10 C22_10 H22A_10 126.4 . . ?
C22_10 C23_10 N22_10 107.1(2) . . ?
C22_10 C23_10 H23_10 126.5 . . ?
N22_10 C23_10 H23_10 126.5 . . ?
C21_11 N21_11 C22_11 108.8(2) . . ?
C21_11 N21_11 H21_11 125.6 . . ?
C22_11 N21_11 H21_11 125.6 . . ?
C21_11 N22_11 C23_11 108.1(2) . . ?
C21_11 N22_11 H22_11 125.9 . . ?
C23_11 N22_11 H22_11 125.9 . . ?
N21_11 C21_11 N22_11 108.8(2) . . ?
N21_11 C21_11 H21A_11 125.6 . . ?
N22_11 C21_11 H21A_11 125.6 . . ?
C23_11 C22_11 N21_11 106.7(2) . . ?
C23_11 C22_11 H22A_11 126.7 . . ?
N21_11 C22_11 H22A_11 126.7 . . ?
C22_11 C23_11 N22_11 107.7(2) . . ?
C22_11 C23_11 H23_11 126.2 . . ?
N22_11 C23_11 H23_11 126.2 . . ?
C21_12 N21_12 C22_12 108.4(2) . . ?
C21_12 N21_12 H21_12 125.8 . . ?
C22_12 N21_12 H21_12 125.8 . . ?
C21_12 N22_12 C23_12 108.1(2) . . ?
C21_12 N22_12 H22_12 125.9 . . ?
C23_12 N22_12 H22_12 125.9 . . ?
N21_12 C21_12 N22_12 109.1(2) . . ?
N21_12 C21_12 H21A_12 125.5 . . ?
N22_12 C21_12 H21A_12 125.5 . . ?
C23_12 C22_12 N21_12 107.2(2) . . ?
C23_12 C22_12 H22A_12 126.4 . . ?
N21_12 C22_12 H22A_12 126.4 . . ?
C22_12 C23_12 N22_12 107.2(2) . . ?
C22_12 C23_12 H23_12 126.4 . . ?
N22_12 C23_12 H23_12 126.4 . . ?
C32_13 O32_13 C31_13 116.1(2) . . ?
O31_13 C32_13 O32_13 124.0(3) . . ?
O31_13 C32_13 C33_13 124.8(3) . . ?
O32_13 C32_13 C33_13 111.1(2) . . ?
C32_13 C33_13 H33A_13 109.5 . . ?
C32_13 C33_13 H33B_13 109.5 . . ?
H33A_13 C33_13 H33B_13 109.5 . . ?
C32_13 C33_13 H33C_13 109.5 . . ?
H33A_13 C33_13 H33C_13 109.5 . . ?
H33B_13 C33_13 H33C_13 109.5 . . ?
O32_13 C31_13 C34_13 107.1(2) . . ?
O32_13 C31_13 H31A_13 110.3 . . ?
C34_13 C31_13 H31A_13 110.3 . . ?
O32_13 C31_13 H31B_13 110.3 . . ?
C34_13 C31_13 H31B_13 110.3 . . ?
H31A_13 C31_13 H31B_13 108.5 . . ?
C31_13 C34_13 H34A_13 109.5 . . ?
C31_13 C34_13 H34B_13 109.5 . . ?
H34A_13 C34_13 H34B_13 109.5 . . ?
C31_13 C34_13 H34C_13 109.5 . . ?
H34A_13 C34_13 H34C_13 109.5 . . ?
H34B_13 C34_13 H34C_13 109.5 . . ?
C32_14 O32_14 C33_14 116.3(2) . . ?
O31_14 C32_14 O32_14 123.0(3) . . ?
O31_14 C32_14 C31_14 125.4(3) . . ?
O32_14 C32_14 C31_14 111.5(2) . . ?
O32_14 C33_14 C34_14 106.9(2) . . ?
O32_14 C33_14 H33A_14 110.3 . . ?
C34_14 C33_14 H33A_14 110.3 . . ?
O32_14 C33_14 H33B_14 110.3 . . ?
C34_14 C33_14 H33B_14 110.3 . . ?
H33A_14 C33_14 H33B_14 108.6 . . ?
C32_14 C31_14 H31A_14 109.5 . . ?
C32_14 C31_14 H31B_14 109.5 . . ?
H31A_14 C31_14 H31B_14 109.5 . . ?
C32_14 C31_14 H31C_14 109.5 . . ?
H31A_14 C31_14 H31C_14 109.5 . . ?
H31B_14 C31_14 H31C_14 109.5 . . ?
C33_14 C34_14 H34A_14 109.5 . . ?
C33_14 C34_14 H34B_14 109.5 . . ?
H34A_14 C34_14 H34B_14 109.5 . . ?
C33_14 C34_14 H34C_14 109.5 . . ?
H34A_14 C34_14 H34C_14 109.5 . . ?
H34B_14 C34_14 H34C_14 109.5 . . ?
C32A_15 O32A_15 C33A_15 117.3(7) . . ?
C34A_15 C33A_15 O32A_15 108.1(7) . . ?
C34A_15 C33A_15 H33A_15 110.1 . . ?
O32A_15 C33A_15 H33A_15 110.1 . . ?
C34A_15 C33A_15 H33B_15 110.1 . . ?
O32A_15 C33A_15 H33B_15 110.1 . . ?
H33A_15 C33A_15 H33B_15 108.4 . . ?
C32A_15 C31A_15 H31A_15 109.5 . . ?
C32A_15 C31A_15 H31B_15 109.5 . . ?
H31A_15 C31A_15 H31B_15 109.5 . . ?
C32A_15 C31A_15 H31C_15 109.5 . . ?
H31A_15 C31A_15 H31C_15 109.5 . . ?
H31B_15 C31A_15 H31C_15 109.5 . . ?
C33A_15 C34A_15 H34A_15 109.5 . . ?
C33A_15 C34A_15 H34B_15 109.5 . . ?
H34A_15 C34A_15 H34B_15 109.5 . . ?
C33A_15 C34A_15 H34C_15 109.5 . . ?
H34A_15 C34A_15 H34C_15 109.5 . . ?
H34B_15 C34A_15 H34C_15 109.5 . . ?
O31A_15 C32A_15 O32A_15 122.0(6) . . ?
O31A_15 C32A_15 C31A_15 126.0(7) . . ?
O32A_15 C32A_15 C31A_15 112.0(7) . . ?
C32_15 O32_15 C33_15 117.4(8) . . ?
O32_15 C33_15 C34_15 108.4(8) . . ?
O32_15 C33_15 H33C_15 110.0 . . ?
C34_15 C33_15 H33C_15 110.0 . . ?
O32_15 C33_15 H33D_15 110.0 . . ?
C34_15 C33_15 H33D_15 110.0 . . ?
H33C_15 C33_15 H33D_15 108.4 . . ?
C32_15 C31_15 H31D_15 109.5 . . ?
C32_15 C31_15 H31E_15 109.5 . . ?
H31D_15 C31_15 H31E_15 109.5 . . ?
C32_15 C31_15 H31F_15 109.5 . . ?
H31D_15 C31_15 H31F_15 109.5 . . ?
H31E_15 C31_15 H31F_15 109.5 . . ?
C33_15 C34_15 H34D_15 109.5 . . ?
C33_15 C34_15 H34E_15 109.5 . . ?
H34D_15 C34_15 H34E_15 109.5 . . ?
C33_15 C34_15 H34F_15 109.5 . . ?
H34D_15 C34_15 H34F_15 109.5 . . ?
H34E_15 C34_15 H34F_15 109.5 . . ?
O31_15 C32_15 O32_15 121.6(8) . . ?
O31_15 C32_15 C31_15 127.0(8) . . ?
O32_15 C32_15 C31_15 110.9(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14_1 H14_1 O31_14 0.95 2.59 3.494(4) 158.1 4_665
C12_2 H12_2 Cl1_4 0.95 2.79 3.597(3) 142.8 2_556
C12_2 H12_2 Cl1A_4 0.95 2.74 3.649(5) 161.5 2_556
C14_3 H14_3 O31_13 0.95 2.63 3.544(4) 160.6 3_766
C9_4 H9A_4 Cl1A_4 0.99 2.58 3.125(5) 114.9 .
C12A_4 H12A_4 Cl2_2 0.95 2.97 3.895(2) 165.6 2_546
C9_5 H9B_5 Cl1_5 0.99 2.56 3.069(2) 111.6 .
C9_5 H9B_5 Cl1A_5 0.99 2.60 3.142(5) 114.2 .
C12_6 H12_6 Cl1_5 0.95 2.85 3.656(3) 143.6 2_646
C12_6 H12_6 Cl1A_5 0.95 2.83 3.733(5) 159.9 2_646
N21_7 H21_7 O2_3 0.88 1.77 2.633(3) 167.9 .
N22_7 H22_7 O1_1 0.88 1.87 2.693(3) 154.7 .
N22_7 H22_7 N2_1 0.88 2.46 3.082(3) 127.7 .
C21_7 H21A_7 O1_2 0.95 2.24 3.185(3) 172.2 .
C22_7 H22A_7 Cl1_1 0.95 2.83 3.696(3) 152.0 .
C23_7 H23_7 Cl2_4 0.95 2.89 3.797(3) 159.9 4_665
N21_8 H21_8 O1_5 0.88 1.88 2.708(3) 156.8 1_455
N21_8 H21_8 N2_5 0.88 2.47 3.068(3) 125.7 1_455
N22_8 H22_8 O2_6 0.88 1.78 2.636(3) 163.0 .
C21_8 H21A_8 O1_5 0.95 2.24 3.188(3) 175.8 3_567
C21_8 H21A_8 O2_5 0.95 2.63 3.290(3) 127.1 3_567
N21_9 H21_9 O2_1 0.88 1.79 2.653(3) 167.4 .
N22_9 H22_9 O1_3 0.88 1.89 2.707(3) 154.5 1_455
N22_9 H22_9 N2_3 0.88 2.47 3.095(3) 128.1 1_455
C21_9 H21A_9 Cl1_3 0.95 2.90 3.770(3) 152.6 1_455
C22_9 H22A_9 O1_4 0.95 2.23 3.171(3) 171.5 .
C22_9 H22A_9 O2_4 0.95 2.60 3.212(3) 122.9 .
C23_9 H23_9 Cl2_5 0.95 2.95 3.847(3) 157.2 3_666
N21_10 H21_10 O1_4 0.88 2.83 3.447(3) 128.3 .
N22_10 H22_10 O1_2 0.88 1.84 2.688(3) 160.0 .
N22_10 H22_10 N2_2 0.88 2.52 3.080(3) 122.4 .
C21_10 H21A_10 O1_1 0.95 2.23 3.182(3) 176.4 .
C21_10 H21A_10 O2_1 0.95 2.56 3.228(3) 127.9 .
C22_10 H22A_10 Cl2_6 0.95 2.96 3.855(3) 158.0 .
C23_10 H23_10 O31A_15 0.95 2.44 3.017(5) 119.1 .
N21_11 H21_11 N2_4 0.88 2.45 3.055(3) 126.4 1_655
N22_11 H22_11 O2_2 0.88 1.77 2.639(3) 166.7 .
C21_11 H21A_11 O1_3 0.95 2.24 3.190(3) 176.8 .
C21_11 H21A_11 O2_3 0.95 2.56 3.221(3) 127.0 .
N21_12 H21_12 O1_6 0.88 1.83 2.674(3) 159.8 .
N21_12 H21_12 N2_6 0.88 2.54 3.098(3) 122.4 .
N22_12 H22_12 O2_5 0.88 1.78 2.657(3) 170.4 .
C21_12 H21A_12 O1_6 0.95 2.25 3.199(3) 176.1 3_567
C22_12 H22A_12 O31_15 0.95 2.43 3.003(6) 119.0 .
C23_12 H23_12 Cl1_2 0.95 2.95 3.845(3) 157.6 .

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder using paratone oil'
_olex2_submission_original_sample_id L3-85-C1
_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 1.814
_oxdiff_exptl_absorpt_empirical_full_min 0.567
_vrf_DIFMX01_2015lms046b         
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: Results from residual positive denisty arising from rotational disorder of dichlorine-substituted rings for which modelling does not give significant improvements.
;
_vrf_PLAT097_2015lms046b         
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.09 eA-3  
RESPONSE: Arises from remaining rotational disorder in dichlorine-substituted rings on lonidamine, from additional chlorine position after ~180 rotation.  Modelling of this disorder does not significantly improve the structural model or add anything further chemically as the minor disorder component is in the order of 6-7%.
_vrf_PLAT910_2015lms046b
;
####################################################################### 
# 
# 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_LON-PIPE
_database_code_depnum_ccdc_archive 'CCDC 1531956'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H9 Cl2 N2 O2), 2(C2 H6 N)'
_chemical_formula_sum            'C34 H30 Cl4 N6 O4'
_chemical_formula_weight         728.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c34 h30 c14 n6 o4'
_chemical_oxdiff_usercomment     L3-31-C2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.6186(5)
_cell_length_b                   12.3390(8)
_cell_length_c                   12.5559(7)
_cell_angle_alpha                68.926(6)
_cell_angle_beta                 85.447(4)
_cell_angle_gamma                88.975(4)
_cell_volume                     1674.24(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10444
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.1520
_cell_measurement_theta_min      3.3160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.784
_exptl_crystal_size_mid          0.1089
_exptl_crystal_size_min          0.0687
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         2.480
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   57.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  -95.0000  -58.0000 164

#__ type_ start__ end____ width___ exp.time_
  2 omega  -57.00    3.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.7923   95.0000   52.0000 120

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   25.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.7923  -95.0000  -58.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00  106.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  178.0000 -120.0000 142

#__ type_ start__ end____ width___ exp.time_
  5 omega  -62.00   44.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  -38.0000  -90.0000 212

#__ type_ start__ end____ width___ exp.time_
  6 omega  -62.00   44.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  -38.0000 -180.0000 212

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00  106.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  178.0000 -180.0000 142

#__ type_ start__ end____ width___ exp.time_
  8 omega   -7.00   18.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.7923  -99.0000  150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.0216434000
_diffrn_orient_matrix_UB_12      -0.0573262000
_diffrn_orient_matrix_UB_13      0.0291479000
_diffrn_orient_matrix_UB_21      0.0178819000
_diffrn_orient_matrix_UB_22      0.0015628000
_diffrn_orient_matrix_UB_23      0.0521500000
_diffrn_orient_matrix_UB_31      -0.0544321000
_diffrn_orient_matrix_UB_32      0.0225138000
_diffrn_orient_matrix_UB_33      0.0108848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray'
_diffrn_source_current           0.8
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10825
_reflns_number_total             13510
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         13510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.047
_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)+(0.1037P)²+0.3698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1581
_refine_special_details          
'Non-merohedral twin in approximate ratio 52:48, Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4751(10) 0.5249(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C29(H29A,H29B), C61(H61C,H61D), C62(H62A,H62B), C51(H51C,H51D),
 C52(H52A,H52B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C24(H24),
 C25(H25), C26(H26), C27(H27), C32(H32), C34(H34), C35(H35)
;
_atom_sites_solution_hydrogens   mixed
_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 0.24859(7) 0.69663(7) 0.58067(8) 0.0374(2) Uani 1 1 d . . . . .
Cl2 Cl 0.49454(10) 0.30983(7) 0.65593(8) 0.0571(3) Uani 1 1 d . . . . .
O1 O 0.76759(15) 0.90631(18) 0.86719(16) 0.0227(4) Uani 1 1 d . . . . .
O2 O 0.90449(15) 0.95214(18) 0.72209(17) 0.0222(4) Uani 1 1 d . . . . .
N1 N 0.56096(18) 0.8556(2) 0.64060(19) 0.0184(5) Uani 1 1 d . . . . .
N2 N 0.61585(18) 0.8612(2) 0.73032(19) 0.0175(5) Uani 1 1 d . . . . .
C1 C 0.8025(2) 0.9248(2) 0.7645(2) 0.0166(5) Uani 1 1 d . . . . .
C2 C 0.7178(2) 0.9113(2) 0.6862(2) 0.0160(5) Uani 1 1 d . . . . .
C3 C 0.7307(2) 0.9395(2) 0.5654(2) 0.0158(5) Uani 1 1 d . . . . .
C4 C 0.8164(2) 0.9932(2) 0.4760(2) 0.0174(5) Uani 1 1 d . . . . .
H4 H 0.8864 1.0216 0.4911 0.021 Uiso 1 1 calc R . . . .
C5 C 0.7955(2) 1.0031(2) 0.3668(2) 0.0208(6) Uani 1 1 d . . . . .
H5 H 0.8518 1.0394 0.3056 0.025 Uiso 1 1 calc R . . . .
C6 C 0.6924(2) 0.9607(3) 0.3435(2) 0.0232(6) Uani 1 1 d . . . . .
H6 H 0.6817 0.9674 0.2671 0.028 Uiso 1 1 calc R . . . .
C7 C 0.6066(2) 0.9095(2) 0.4285(2) 0.0213(6) Uani 1 1 d . . . . .
H7 H 0.5366 0.8819 0.4126 0.026 Uiso 1 1 calc R . . . .
C8 C 0.6280(2) 0.9003(2) 0.5400(2) 0.0176(5) Uani 1 1 d . . . . .
C9 C 0.4510(2) 0.7955(2) 0.6605(2) 0.0206(6) Uani 1 1 d . . . . .
H9A H 0.3998 0.8408 0.6012 0.025 Uiso 1 1 calc R . . . .
H9B H 0.4144 0.7910 0.7359 0.025 Uiso 1 1 calc R . . . .
C10 C 0.4622(2) 0.6741(2) 0.6582(2) 0.0189(5) Uani 1 1 d . . . . .
C11 C 0.3751(2) 0.6220(2) 0.6243(2) 0.0216(6) Uani 1 1 d . . . . .
C12 C 0.3835(3) 0.5105(3) 0.6235(3) 0.0288(7) Uani 1 1 d . . . . .
H12 H 0.3225 0.4765 0.5996 0.035 Uiso 1 1 calc R . . . .
C13 C 0.4830(3) 0.4500(3) 0.6584(3) 0.0308(7) Uani 1 1 d . . . . .
C14 C 0.5709(3) 0.4969(3) 0.6933(3) 0.0364(8) Uani 1 1 d . . . . .
H14 H 0.6386 0.4534 0.7171 0.044 Uiso 1 1 calc R . . . .
C15 C 0.5610(3) 0.6090(3) 0.6939(3) 0.0305(7) Uani 1 1 d . . . . .
H15 H 0.6221 0.6418 0.7188 0.037 Uiso 1 1 calc R . . . .
Cl21 Cl -0.14715(6) 0.41086(6) 0.80497(6) 0.02453(17) Uani 1 1 d . . . . .
Cl22 Cl -0.11040(6) 0.65753(6) 0.35421(6) 0.02701(18) Uani 1 1 d . . . . .
O21 O 0.23219(15) 0.89524(16) 0.93467(16) 0.0192(4) Uani 1 1 d . . . . .
O22 O 0.38334(16) 0.77664(17) 0.95183(18) 0.0230(4) Uani 1 1 d . . . . .
N21 N 0.06510(17) 0.64105(18) 0.86234(18) 0.0150(4) Uani 1 1 d . . . . .
N22 N 0.10279(18) 0.73608(19) 0.87974(18) 0.0155(4) Uani 1 1 d . . . . .
C21 C 0.2802(2) 0.8029(2) 0.9340(2) 0.0160(5) Uani 1 1 d . . . . .
C22 C 0.2108(2) 0.7151(2) 0.9082(2) 0.0144(5) Uani 1 1 d . . . . .
C23 C 0.2454(2) 0.6020(2) 0.9121(2) 0.0159(5) Uani 1 1 d . . . . .
C24 C 0.3443(2) 0.5322(2) 0.9424(2) 0.0203(6) Uani 1 1 d . . . . .
H24 H 0.4107 0.5609 0.9637 0.024 Uiso 1 1 calc R . . . .
C25 C 0.3412(2) 0.4219(3) 0.9400(3) 0.0242(6) Uani 1 1 d . . . . .
H25 H 0.4064 0.3734 0.9607 0.029 Uiso 1 1 calc R . . . .
C26 C 0.2435(2) 0.3793(2) 0.9075(2) 0.0223(6) Uani 1 1 d . . . . .
H26 H 0.2447 0.3027 0.9064 0.027 Uiso 1 1 calc R . . . .
C27 C 0.1461(2) 0.4453(2) 0.8772(2) 0.0185(5) Uani 1 1 d . . . . .
H27 H 0.0806 0.4164 0.8547 0.022 Uiso 1 1 calc R . . . .
C28 C 0.1488(2) 0.5571(2) 0.8814(2) 0.0152(5) Uani 1 1 d . . . . .
C29 C -0.0540(2) 0.6331(2) 0.8366(2) 0.0159(5) Uani 1 1 d . . . . .
H29A H -0.0979 0.6988 0.8463 0.019 Uiso 1 1 calc R . . . .
H29B H -0.0894 0.5603 0.8922 0.019 Uiso 1 1 calc R . . . .
C30 C -0.0647(2) 0.6348(2) 0.7164(2) 0.0158(5) Uani 1 1 d . . . . .
C31 C -0.1066(2) 0.5413(2) 0.6936(2) 0.0174(5) Uani 1 1 d . . . . .
C32 C -0.1202(2) 0.5466(2) 0.5823(2) 0.0199(5) Uani 1 1 d . . . . .
H32 H -0.1498 0.4819 0.5686 0.024 Uiso 1 1 calc R . . . .
C33 C -0.0894(2) 0.6485(2) 0.4929(2) 0.0189(5) Uani 1 1 d . . . . .
C34 C -0.0452(2) 0.7436(2) 0.5111(2) 0.0191(5) Uani 1 1 d . . . . .
H34 H -0.0232 0.8127 0.4485 0.023 Uiso 1 1 calc R . . . .
C35 C -0.0340(2) 0.7352(2) 0.6230(2) 0.0180(5) Uani 1 1 d . . . . .
H35 H -0.0044 0.8001 0.6363 0.022 Uiso 1 1 calc R . . . .
N61 N 0.0086(2) 0.95175(19) 0.91181(19) 0.0154(4) Uani 1 1 d . . . . .
H61A H 0.089(3) 0.936(3) 0.913(3) 0.019 Uiso 1 1 d R . . . .
H61B H -0.025(3) 0.939(3) 0.862(3) 0.019 Uiso 1 1 d R . . . .
C61 C -0.0070(2) 1.0784(2) 0.8837(2) 0.0175(5) Uani 1 1 d . . . . .
H61C H -0.0904 1.0966 0.8822 0.021 Uiso 1 1 calc R . . . .
H61D H 0.0310 1.1215 0.8069 0.021 Uiso 1 1 calc R . . . .
C62 C -0.0446(2) 0.8839(2) 1.0281(2) 0.0172(5) Uani 1 1 d . . . . .
H62A H -0.0309 0.8001 1.0456 0.021 Uiso 1 1 calc R . . . .
H62B H -0.1290 0.8963 1.0308 0.021 Uiso 1 1 calc R . . . .
N51 N 0.5532(2) 0.92448(19) 0.94631(18) 0.0149(4) Uani 1 1 d . . . . .
H51A H 0.492(3) 0.887(3) 0.941(3) 0.018 Uiso 1 1 d R . . . .
H51B H 0.613(3) 0.907(3) 0.918(3) 0.018 Uiso 1 1 d R . . . .
C51 C 0.5323(2) 1.0486(2) 0.8793(2) 0.0180(5) Uani 1 1 d . . . . .
H51C H 0.5185 1.0576 0.7998 0.022 Uiso 1 1 calc R . . . .
H51D H 0.6016 1.0954 0.8767 0.022 Uiso 1 1 calc R . . . .
C52 C 0.5712(2) 0.9075(2) 1.0672(2) 0.0162(5) Uani 1 1 d . . . . .
H52A H 0.6416 0.9501 1.0699 0.019 Uiso 1 1 calc R . . . .
H52B H 0.5821 0.8239 1.1110 0.019 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.739(3) . ?
Cl2 C13 1.743(3) . ?
O1 C1 1.260(3) . ?
O2 C1 1.260(3) . ?
N1 N2 1.361(3) . ?
N1 C8 1.366(3) . ?
N1 C9 1.447(3) . ?
N2 C2 1.329(3) . ?
C1 C2 1.496(3) . ?
C2 C3 1.425(4) . ?
C3 C4 1.415(4) . ?
C3 C8 1.397(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.405(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(4) . ?
C10 C11 1.382(4) . ?
C10 C15 1.398(4) . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(5) . ?
C13 C14 1.358(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(5) . ?
C15 H15 0.9500 . ?
Cl21 C31 1.753(3) . ?
Cl22 C33 1.742(3) . ?
O21 C21 1.263(3) . ?
O22 C21 1.251(3) . ?
N21 N22 1.354(3) . ?
N21 C28 1.378(3) . ?
N21 C29 1.459(3) . ?
N22 C22 1.328(3) . ?
C21 C22 1.502(3) . ?
C22 C23 1.430(3) . ?
C23 C24 1.415(4) . ?
C23 C28 1.401(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.373(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.408(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.400(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.516(3) . ?
C30 C31 1.390(3) . ?
C30 C35 1.394(4) . ?
C31 C32 1.397(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.381(4) . ?
C33 C34 1.388(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.388(4) . ?
C35 H35 0.9500 . ?
N61 H61A 0.95(3) . ?
N61 H61B 0.82(3) . ?
N61 C61 1.485(3) . ?
N61 C62 1.487(3) . ?
C61 H61C 0.9900 . ?
C61 H61D 0.9900 . ?
C61 C62 1.512(3) 2_577 ?
C62 C61 1.512(3) 2_577 ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
N51 H51A 0.88(3) . ?
N51 H51B 0.81(3) . ?
N51 C51 1.485(3) . ?
N51 C52 1.487(3) . ?
C51 H51C 0.9900 . ?
C51 H51D 0.9900 . ?
C51 C52 1.518(3) 2_677 ?
C52 C51 1.518(3) 2_677 ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 111.5(2) . . ?
N2 N1 C9 120.2(2) . . ?
C8 N1 C9 127.9(2) . . ?
C2 N2 N1 106.0(2) . . ?
O1 C1 C2 118.2(2) . . ?
O2 C1 O1 125.1(2) . . ?
O2 C1 C2 116.7(2) . . ?
N2 C2 C1 119.3(2) . . ?
N2 C2 C3 111.3(2) . . ?
C3 C2 C1 129.4(2) . . ?
C4 C3 C2 136.2(2) . . ?
C8 C3 C2 104.3(2) . . ?
C8 C3 C4 119.5(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(2) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 121.7 . . ?
C6 C7 C8 116.6(2) . . ?
C8 C7 H7 121.7 . . ?
N1 C8 C3 106.9(2) . . ?
N1 C8 C7 130.5(2) . . ?
C3 C8 C7 122.6(2) . . ?
N1 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
N1 C9 C10 112.8(2) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 C15 117.4(3) . . ?
C15 C10 C9 120.7(2) . . ?
C10 C11 Cl1 120.2(2) . . ?
C12 C11 Cl1 117.3(2) . . ?
C12 C11 C10 122.5(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 Cl2 118.1(3) . . ?
C14 C13 Cl2 120.0(3) . . ?
C14 C13 C12 121.9(3) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
N22 N21 C28 111.4(2) . . ?
N22 N21 C29 120.46(19) . . ?
C28 N21 C29 127.9(2) . . ?
C22 N22 N21 106.6(2) . . ?
O21 C21 C22 118.8(2) . . ?
O22 C21 O21 125.9(2) . . ?
O22 C21 C22 115.2(2) . . ?
N22 C22 C21 121.2(2) . . ?
N22 C22 C23 111.1(2) . . ?
C23 C22 C21 127.7(2) . . ?
C24 C23 C22 136.1(2) . . ?
C28 C23 C22 104.3(2) . . ?
C28 C23 C24 119.6(2) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 C23 118.0(2) . . ?
C25 C24 H24 121.0 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.3(3) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.0 . . ?
C27 C26 C25 122.1(3) . . ?
C27 C26 H26 119.0 . . ?
C26 C27 H27 121.7 . . ?
C26 C27 C28 116.5(2) . . ?
C28 C27 H27 121.7 . . ?
N21 C28 C23 106.7(2) . . ?
N21 C28 C27 130.8(2) . . ?
C27 C28 C23 122.5(2) . . ?
N21 C29 H29A 108.9 . . ?
N21 C29 H29B 108.9 . . ?
N21 C29 C30 113.38(19) . . ?
H29A C29 H29B 107.7 . . ?
C30 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C31 C30 C29 123.3(2) . . ?
C31 C30 C35 117.3(2) . . ?
C35 C30 C29 119.4(2) . . ?
C30 C31 Cl21 120.9(2) . . ?
C30 C31 C32 122.2(2) . . ?
C32 C31 Cl21 116.8(2) . . ?
C31 C32 H32 121.0 . . ?
C33 C32 C31 118.1(2) . . ?
C33 C32 H32 121.0 . . ?
C32 C33 Cl22 118.4(2) . . ?
C32 C33 C34 121.9(2) . . ?
C34 C33 Cl22 119.7(2) . . ?
C33 C34 H34 120.9 . . ?
C33 C34 C35 118.2(2) . . ?
C35 C34 H34 120.9 . . ?
C30 C35 H35 118.9 . . ?
C34 C35 C30 122.2(2) . . ?
C34 C35 H35 118.9 . . ?
H61A N61 H61B 116(3) . . ?
C61 N61 H61A 108.7(19) . . ?
C61 N61 H61B 103(2) . . ?
C61 N61 C62 111.30(19) . . ?
C62 N61 H61A 106.4(18) . . ?
C62 N61 H61B 111(2) . . ?
N61 C61 H61C 109.6 . . ?
N61 C61 H61D 109.6 . . ?
N61 C61 C62 110.1(2) . 2_577 ?
H61C C61 H61D 108.1 . . ?
C62 C61 H61C 109.6 2_577 . ?
C62 C61 H61D 109.6 2_577 . ?
N61 C62 C61 110.0(2) . 2_577 ?
N61 C62 H62A 109.7 . . ?
N61 C62 H62B 109.7 . . ?
C61 C62 H62A 109.7 2_577 . ?
C61 C62 H62B 109.7 2_577 . ?
H62A C62 H62B 108.2 . . ?
H51A N51 H51B 114(3) . . ?
C51 N51 H51A 106(2) . . ?
C51 N51 H51B 107(2) . . ?
C51 N51 C52 110.87(19) . . ?
C52 N51 H51A 112(2) . . ?
C52 N51 H51B 107(2) . . ?
N51 C51 H51C 109.5 . . ?
N51 C51 H51D 109.5 . . ?
N51 C51 C52 110.7(2) . 2_677 ?
H51C C51 H51D 108.1 . . ?
C52 C51 H51C 109.5 2_677 . ?
C52 C51 H51D 109.5 2_677 . ?
N51 C52 C51 110.0(2) . 2_677 ?
N51 C52 H52A 109.7 . . ?
N51 C52 H52B 109.7 . . ?
C51 C52 H52A 109.7 2_677 . ?
C51 C52 H52B 109.7 2_677 . ?
H52A C52 H52B 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 Cl2 0.95 2.83 3.494(3) 127.7 2_666
C14 H14 Cl21 0.95 2.77 3.655(4) 155.7 1_655
C27 H27 Cl21 0.95 2.77 3.665(3) 156.5 .
C29 H29B Cl21 0.99 2.58 3.131(3) 115.0 .
N61 H61A O21 0.95(3) 1.74(3) 2.688(3) 173(3) .
N61 H61B O1 0.82(3) 2.44(3) 3.000(3) 126(3) 1_455
N61 H61B O2 0.82(3) 1.95(3) 2.755(3) 164(3) 1_455
C62 H62B O1 0.99 2.43 3.033(3) 119.1 1_455
N51 H51A O22 0.88(3) 1.83(3) 2.692(3) 166(3) .
N51 H51B O1 0.81(3) 1.86(3) 2.643(3) 161(3) .
N51 H51B N2 0.81(3) 2.62(3) 3.111(3) 121(3) .
C52 H52A O21 0.99 2.41 3.361(3) 161.1 2_677

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 C11 C12 C13 -179.7(2) . . . . ?
Cl2 C13 C14 C15 179.4(3) . . . . ?
O1 C1 C2 N2 -11.8(4) . . . . ?
O1 C1 C2 C3 171.9(3) . . . . ?
O2 C1 C2 N2 167.1(2) . . . . ?
O2 C1 C2 C3 -9.2(4) . . . . ?
N1 N2 C2 C1 -176.8(2) . . . . ?
N1 N2 C2 C3 0.1(3) . . . . ?
N1 C9 C10 C11 -150.4(2) . . . . ?
N1 C9 C10 C15 31.4(4) . . . . ?
N2 N1 C8 C3 -1.5(3) . . . . ?
N2 N1 C8 C7 178.6(3) . . . . ?
N2 N1 C9 C10 -99.4(3) . . . . ?
N2 C2 C3 C4 178.9(3) . . . . ?
N2 C2 C3 C8 -1.0(3) . . . . ?
C1 C2 C3 C4 -4.6(5) . . . . ?
C1 C2 C3 C8 175.6(2) . . . . ?
C2 C3 C4 C5 179.2(3) . . . . ?
C2 C3 C8 N1 1.4(3) . . . . ?
C2 C3 C8 C7 -178.7(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C3 C8 N1 -178.5(2) . . . . ?
C4 C3 C8 C7 1.5(4) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C6 C7 C8 N1 179.4(3) . . . . ?
C6 C7 C8 C3 -0.5(4) . . . . ?
C8 N1 N2 C2 0.8(3) . . . . ?
C8 N1 C9 C10 72.8(3) . . . . ?
C8 C3 C4 C5 -1.0(4) . . . . ?
C9 N1 N2 C2 174.2(2) . . . . ?
C9 N1 C8 C3 -174.2(2) . . . . ?
C9 N1 C8 C7 5.9(5) . . . . ?
C9 C10 C11 Cl1 0.9(4) . . . . ?
C9 C10 C11 C12 -179.0(3) . . . . ?
C9 C10 C15 C14 179.2(3) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C10 C15 C14 0.9(4) . . . . ?
C11 C12 C13 Cl2 -179.3(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C10 -0.5(5) . . . . ?
C15 C10 C11 Cl1 179.1(2) . . . . ?
C15 C10 C11 C12 -0.7(4) . . . . ?
Cl21 C31 C32 C33 179.7(2) . . . . ?
Cl22 C33 C34 C35 177.38(19) . . . . ?
O21 C21 C22 N22 4.0(4) . . . . ?
O21 C21 C22 C23 -174.6(2) . . . . ?
O22 C21 C22 N22 -175.1(2) . . . . ?
O22 C21 C22 C23 6.3(4) . . . . ?
N21 N22 C22 C21 -179.9(2) . . . . ?
N21 N22 C22 C23 -1.2(3) . . . . ?
N21 C29 C30 C31 115.0(3) . . . . ?
N21 C29 C30 C35 -66.6(3) . . . . ?
N22 N21 C28 C23 -0.3(3) . . . . ?
N22 N21 C28 C27 177.6(2) . . . . ?
N22 N21 C29 C30 113.1(2) . . . . ?
N22 C22 C23 C24 -175.7(3) . . . . ?
N22 C22 C23 C28 1.0(3) . . . . ?
C21 C22 C23 C24 2.9(5) . . . . ?
C21 C22 C23 C28 179.6(2) . . . . ?
C22 C23 C24 C25 176.5(3) . . . . ?
C22 C23 C28 N21 -0.4(3) . . . . ?
C22 C23 C28 C27 -178.5(2) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C23 C28 N21 177.0(2) . . . . ?
C24 C23 C28 C27 -1.2(4) . . . . ?
C24 C25 C26 C27 -0.4(4) . . . . ?
C25 C26 C27 C28 -0.6(4) . . . . ?
C26 C27 C28 N21 -176.3(3) . . . . ?
C26 C27 C28 C23 1.3(4) . . . . ?
C28 N21 N22 C22 0.9(3) . . . . ?
C28 N21 C29 C30 -72.5(3) . . . . ?
C28 C23 C24 C25 0.2(4) . . . . ?
C29 N21 N22 C22 176.1(2) . . . . ?
C29 N21 C28 C23 -175.1(2) . . . . ?
C29 N21 C28 C27 2.9(4) . . . . ?
C29 C30 C31 Cl21 -1.7(3) . . . . ?
C29 C30 C31 C32 177.2(2) . . . . ?
C29 C30 C35 C34 -177.9(2) . . . . ?
C30 C31 C32 C33 0.7(4) . . . . ?
C31 C30 C35 C34 0.6(4) . . . . ?
C31 C32 C33 Cl22 -178.0(2) . . . . ?
C31 C32 C33 C34 0.5(4) . . . . ?
C32 C33 C34 C35 -1.0(4) . . . . ?
C33 C34 C35 C30 0.5(4) . . . . ?
C35 C30 C31 Cl21 179.81(19) . . . . ?
C35 C30 C31 C32 -1.2(4) . . . . ?
C61 N61 C62 C61 -57.6(3) . . . 2_577 ?
C62 N61 C61 C62 57.7(3) . . . 2_577 ?
C51 N51 C52 C51 57.3(3) . . . 2_677 ?
C52 N51 C51 C52 -57.6(3) . . . 2_677 ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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 9 -11 0.0363 -0.0527 8.8824 -11.1127 -0.8320 -0.5666 0.0819
0 -9 11 0.0324 0.0527 -8.8824 11.1127 0.8320 0.5666 -0.0819
0 -15 -13 0.0544 -0.1560 -15.1727 -12.9048 0.4970 -0.6995 -0.4736
0 15 13 0.0544 0.1560 15.1727 12.9048 -0.4970 0.6995 0.4736
-16 1 -1 0.3036 -16.0625 1.0292 -0.8250 0.2646 -0.3286 0.8885
16 -1 2 0.4682 16.0703 -1.0175 1.8279 -0.2362 0.3811 -0.8777

_olex2_date_sample_data_collection 2015-09-28
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_original_sample_id L3-31-C2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4751(10)
2 0.5249(10)

####################################################################### 
# 
# 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_LON-2APYN_acn
_database_code_depnum_ccdc_archive 'CCDC 1531947'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Cl2 N2 O2, C5 H7 N2'
_chemical_formula_sum            'C20 H16 Cl2 N4 O2'
_chemical_formula_weight         415.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16 N4 O2 Cl2'
_chemical_oxdiff_usercomment     L3-79-A2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.1266(5)
_cell_length_b                   22.3945(10)
_cell_length_c                   8.5821(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.718(6)
_cell_angle_gamma                90
_cell_volume                     2048.06(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4167
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5580
_cell_measurement_theta_min      3.2140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
15 4 0 0.0475
-15 -4 0 0.0418
-5 -8 12 0.3596
5 8 -12 0.3809
0 32 0 0.0078
0 -32 0 0.0078

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.772
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.016
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
15.0102 3.9938 -0.0132 0.9506 -0.3298 -0.0011
-15.0102 -3.9938 0.0132 -0.9506 0.3298 0.0011
-4.9771 -7.9357 12.0041 -0.0593 0.0278 1.0227
4.9771 7.9357 -12.0041 0.0593 -0.0278 -1.0227
0.0150 31.9994 -0.0222 0.4395 0.8784 -0.2493
-0.0150 -31.9994 0.0222 -0.4395 -0.8784 0.2493

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14679
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.639
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  91.00   0.50   60.00    --   15.17  57.00 150.00  214
  2  ω    -14.00  93.00   0.50   60.00    --   15.17  38.00  60.00  214
  3  ω    -10.00  68.00   0.50   60.00    --   15.17  57.00-120.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0597020000
_diffrn_orient_matrix_UB_12      0.0137272000
_diffrn_orient_matrix_UB_13      0.0288892000
_diffrn_orient_matrix_UB_21      -0.0292725000
_diffrn_orient_matrix_UB_22      0.0274690000
_diffrn_orient_matrix_UB_23      0.0083398000
_diffrn_orient_matrix_UB_31      0.0020548000
_diffrn_orient_matrix_UB_32      -0.0077346000
_diffrn_orient_matrix_UB_33      0.0809322000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3543
_reflns_number_total             4674
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.324
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+1.4362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          
'SMTBX solvent masking applied as implemented in Olex2. Electron count indicates acetonitrile solvent is likely., SQUEEZE'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C22(H22A),
 C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.61250(6) 0.37460(3) 0.85466(12) 0.0640(3) Uani 1 1 d . . . . .
Cl2 Cl 0.85165(5) 0.17892(3) 0.74677(8) 0.04218(17) Uani 1 1 d . . . . .
O1 O 0.17226(14) 0.30580(6) 0.30296(17) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.12535(17) 0.40289(7) 0.29438(18) 0.0434(4) Uani 1 1 d . . . . .
N1 N 0.33726(15) 0.33211(8) 0.7872(2) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.29276(15) 0.31429(7) 0.63059(19) 0.0240(4) Uani 1 1 d . . . . .
C1 C 0.17249(19) 0.35604(9) 0.3681(2) 0.0269(4) Uani 1 1 d . . . . .
C2 C 0.23275(18) 0.36118(9) 0.5473(2) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.23755(19) 0.41131(9) 0.6525(2) 0.0263(4) Uani 1 1 d . . . . .
C4 C 0.1900(2) 0.46989(10) 0.6355(3) 0.0351(5) Uani 1 1 d . . . . .
H4 H 0.1417 0.4846 0.5327 0.042 Uiso 1 1 calc R . . . .
C5 C 0.2157(3) 0.50527(11) 0.7723(3) 0.0449(6) Uani 1 1 d . . . . .
H5 H 0.1849 0.5451 0.7635 0.054 Uiso 1 1 calc R . . . .
C6 C 0.2868(2) 0.48348(11) 0.9253(3) 0.0463(7) Uani 1 1 d . . . . .
H6 H 0.3033 0.5093 1.0168 0.056 Uiso 1 1 calc R . . . .
C7 C 0.3329(2) 0.42659(11) 0.9467(3) 0.0384(6) Uani 1 1 d . . . . .
H7 H 0.3803 0.4122 1.0504 0.046 Uiso 1 1 calc R . . . .
C8 C 0.30642(19) 0.39025(9) 0.8065(3) 0.0278(5) Uani 1 1 d . . . . .
C9 C 0.40900(19) 0.29088(10) 0.9105(2) 0.0285(5) Uani 1 1 d . . . . .
H9A H 0.3527 0.2587 0.9263 0.034 Uiso 1 1 calc R . . . .
H9B H 0.4404 0.3125 1.0150 0.034 Uiso 1 1 calc R . . . .
C10 C 0.51890(18) 0.26320(10) 0.8669(2) 0.0257(4) Uani 1 1 d . . . . .
C11 C 0.6153(2) 0.29728(10) 0.8390(3) 0.0341(5) Uani 1 1 d . . . . .
C12 C 0.7165(2) 0.27169(11) 0.8010(3) 0.0378(6) Uani 1 1 d . . . . .
H12 H 0.7808 0.2959 0.7814 0.045 Uiso 1 1 calc R . . . .
C13 C 0.72214(19) 0.21045(10) 0.7922(3) 0.0319(5) Uani 1 1 d . . . . .
C14 C 0.6297(2) 0.17468(10) 0.8204(3) 0.0328(5) Uani 1 1 d . . . . .
H14 H 0.6350 0.1324 0.8150 0.039 Uiso 1 1 calc R . . . .
C15 C 0.52864(19) 0.20163(10) 0.8567(3) 0.0302(5) Uani 1 1 d . . . . .
H15 H 0.4642 0.1772 0.8751 0.036 Uiso 1 1 calc R . . . .
N21 N 0.11330(18) 0.20426(8) 0.4647(3) 0.0299(4) Uani 1 1 d . . . . .
H21A H 0.128(2) 0.2337(12) 0.405(3) 0.040(7) Uiso 1 1 d . . . . .
H21B H 0.139(2) 0.2046(11) 0.570(3) 0.044(7) Uiso 1 1 d . . . . .
N22 N 0.01440(16) 0.11512(8) 0.4809(2) 0.0259(4) Uani 1 1 d . . . . .
H22 H 0.049(3) 0.1132(12) 0.595(3) 0.057(8) Uiso 1 1 d . . . . .
C21 C 0.03996(18) 0.16013(9) 0.3900(2) 0.0246(4) Uani 1 1 d . . . . .
C22 C -0.0618(2) 0.06863(9) 0.4147(3) 0.0317(5) Uani 1 1 d . . . . .
H22A H -0.0783 0.0387 0.4844 0.038 Uiso 1 1 calc R . . . .
C23 C -0.1147(2) 0.06389(10) 0.2520(3) 0.0352(5) Uani 1 1 d . . . . .
H23 H -0.1675 0.0312 0.2064 0.042 Uiso 1 1 calc R . . . .
C24 C -0.0885(2) 0.10932(10) 0.1530(3) 0.0340(5) Uani 1 1 d . . . . .
H24 H -0.1233 0.1069 0.0382 0.041 Uiso 1 1 calc R . . . .
C25 C -0.01414(19) 0.15680(10) 0.2188(3) 0.0293(5) Uani 1 1 d . . . . .
H25 H 0.0013 0.1874 0.1504 0.035 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.738(2) . ?
Cl2 C13 1.747(2) . ?
O1 C1 1.256(2) . ?
O2 C1 1.259(2) . ?
N1 N2 1.352(2) . ?
N1 C8 1.368(3) . ?
N1 C9 1.457(3) . ?
N2 C2 1.336(3) . ?
C1 C2 1.494(3) . ?
C2 C3 1.432(3) . ?
C3 C4 1.406(3) . ?
C3 C8 1.405(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.411(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.366(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.412(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.388(3) . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(3) . ?
C13 C14 1.379(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
N21 H21A 0.88(3) . ?
N21 H21B 0.87(3) . ?
N21 C21 1.324(3) . ?
N22 H22 0.95(3) . ?
N22 C21 1.354(3) . ?
N22 C22 1.359(3) . ?
C21 C25 1.420(3) . ?
C22 H22A 0.9500 . ?
C22 C23 1.355(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.409(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.366(3) . ?
C25 H25 0.9500 . ?

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
N2 N1 C8 111.58(16) . . ?
N2 N1 C9 120.15(16) . . ?
C8 N1 C9 128.26(17) . . ?
C2 N2 N1 106.50(16) . . ?
O1 C1 O2 125.12(19) . . ?
O1 C1 C2 118.04(18) . . ?
O2 C1 C2 116.84(19) . . ?
N2 C2 C1 119.82(17) . . ?
N2 C2 C3 110.87(18) . . ?
C3 C2 C1 129.31(18) . . ?
C4 C3 C2 136.2(2) . . ?
C8 C3 C2 103.97(18) . . ?
C8 C3 C4 119.85(19) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.4(2) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 H7 121.8 . . ?
C6 C7 C8 116.4(2) . . ?
C8 C7 H7 121.8 . . ?
N1 C8 C3 107.08(17) . . ?
N1 C8 C7 130.8(2) . . ?
C3 C8 C7 122.1(2) . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
N1 C9 C10 113.16(16) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C11 C10 C9 122.4(2) . . ?
C15 C10 C9 120.44(18) . . ?
C15 C10 C11 117.13(19) . . ?
C10 C11 Cl1 120.10(17) . . ?
C12 C11 Cl1 117.68(17) . . ?
C12 C11 C10 122.2(2) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.6(2) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 Cl2 117.95(16) . . ?
C12 C13 C14 121.4(2) . . ?
C14 C13 Cl2 120.62(18) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.7(2) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 C14 121.9(2) . . ?
C10 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
H21A N21 H21B 123(2) . . ?
C21 N21 H21A 117.7(16) . . ?
C21 N21 H21B 119.1(17) . . ?
C21 N22 H22 122.6(17) . . ?
C21 N22 C22 122.59(19) . . ?
C22 N22 H22 114.8(17) . . ?
N21 C21 N22 118.59(19) . . ?
N21 C21 C25 124.0(2) . . ?
N22 C21 C25 117.41(19) . . ?
N22 C22 H22A 119.2 . . ?
C23 C22 N22 121.6(2) . . ?
C23 C22 H22A 119.2 . . ?
C22 C23 H23 121.3 . . ?
C22 C23 C24 117.5(2) . . ?
C24 C23 H23 121.3 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.2(2) . . ?
C25 C24 H24 119.4 . . ?
C21 C25 H25 120.2 . . ?
C24 C25 C21 119.6(2) . . ?
C24 C25 H25 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9A O1 0.99 2.45 3.329(3) 147.3 4_566
C9 H9A N2 0.99 2.62 3.492(3) 147.0 4_566
N21 H21A O1 0.88(3) 1.97(3) 2.838(2) 171(2) .
N21 H21B O1 0.87(3) 1.94(3) 2.795(2) 169(2) 4_566

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 0.000 112.0 21.2 ?
2 0.500 0.500 0.500 112.0 21.2 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id L3-79-A2
_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 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.761
####################################################################### 
# 
# 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_LON-NICO
_database_code_depnum_ccdc_archive 'CCDC 1531962'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2017-02-09
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl2 N2 O2, C6 H6 N2 O'
_chemical_formula_sum            'C21 H16 Cl2 N4 O3'
_chemical_formula_weight         443.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H16 N4 O3 Cl2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_cell_length_a                   20.6918(6)
_cell_length_b                   4.61421(12)
_cell_length_c                   20.1099(5)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.673(2)
_cell_angle_gamma                90.0
_cell_volume                     1919.89(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.7920
_cell_measurement_theta_min      2.1360
_cell_oxdiff_angle_alpha         89.993(2)
_cell_oxdiff_angle_beta          90.704(2)
_cell_oxdiff_angle_gamma         90.099(2)
_cell_oxdiff_length_a            20.6811(5)
_cell_oxdiff_length_b            4.61310(11)
_cell_oxdiff_length_c            20.1253(5)
_cell_oxdiff_measurement_reflns_used 17782
_cell_oxdiff_volume              1919.89(8)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.584
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  73.00   0.50   50.00    --  -17.00  72.00-120.00  180
  2  ω    -68.00  22.00   0.50   50.00    --  -17.00 -72.00 120.00  180
  3  ω    -64.00  22.00   0.50   50.00    --  -17.00 -72.00 -60.00  172
  4  ω    -86.00 -13.00   0.50   50.00    --  -17.00   0.00 -60.00  146
  5  ω    -92.00 -77.00   0.50   50.00    --  -17.00 -18.00  30.00   30
  6  ω    -27.00  73.00   0.50   50.00    --  -17.00  72.00 -60.00  200
  7  ω    -68.50  22.00   0.50   50.00    --  -17.00 -72.00-180.00  181
  8  ω    -68.00  22.00   0.50   50.00    --  -17.00 -72.00   0.00  180
  9  ω    -85.50  -7.00   0.50   50.00    --  -17.00   0.00   0.00  157
 10  ω    -60.00  73.00   0.50   50.00    --  -17.00   0.00 120.00  266
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC10 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228822000
_diffrn_orient_matrix_UB_12      0.0540999000
_diffrn_orient_matrix_UB_13      -0.0228762000
_diffrn_orient_matrix_UB_21      -0.0255515000
_diffrn_orient_matrix_UB_22      0.0487619000
_diffrn_orient_matrix_UB_23      -0.0209853000
_diffrn_orient_matrix_UB_31      0.0001272000
_diffrn_orient_matrix_UB_32      0.1354143000
_diffrn_orient_matrix_UB_33      0.0166923000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4061
_reflns_number_total             4368
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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       
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_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         0.468
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0703P)²+4.7433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1569
_refine_special_details          'Twin law -1 0 0 0 -1 0 0 0 1 at 3.5%'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9651(7)
 0.0349(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C23(H23),
 C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.92048(3) -0.41205(16) 0.47543(4) 0.02531(18) Uani 1 1 d . . . . .
Cl2 Cl 0.98360(4) 0.3008(2) 0.67605(4) 0.0340(2) Uani 1 1 d . . . . .
O1 O 0.57854(10) 0.4759(5) 0.45384(10) 0.0272(5) Uani 1 1 d . . . . .
O2 O 0.61310(11) 0.6444(5) 0.35595(11) 0.0272(5) Uani 1 1 d . . . . .
H2 H 0.583(3) 0.777(14) 0.356(3) 0.077(18) Uiso 1 1 d . . . . .
N1 N 0.75105(11) 0.0243(5) 0.44707(12) 0.0210(5) Uani 1 1 d . . . . .
N2 N 0.69148(11) 0.1302(6) 0.45897(12) 0.0213(5) Uani 1 1 d . . . . .
C1 C 0.61814(14) 0.4853(7) 0.40976(14) 0.0229(6) Uani 1 1 d . . . . .
C2 C 0.67948(13) 0.3211(6) 0.41102(14) 0.0213(6) Uani 1 1 d . . . . .
C3 C 0.73241(14) 0.3446(6) 0.36659(14) 0.0210(6) Uani 1 1 d . . . . .
C4 C 0.74743(15) 0.5130(7) 0.31024(14) 0.0246(6) Uani 1 1 d . . . . .
H4 H 0.7174 0.6480 0.2921 0.030 Uiso 1 1 calc R . . . .
C5 C 0.80736(16) 0.4741(7) 0.28249(15) 0.0277(6) Uani 1 1 d . . . . .
H5 H 0.8186 0.5847 0.2445 0.033 Uiso 1 1 calc R . . . .
C6 C 0.85223(15) 0.2755(7) 0.30888(15) 0.0277(6) Uani 1 1 d . . . . .
H6 H 0.8930 0.2560 0.2882 0.033 Uiso 1 1 calc R . . . .
C7 C 0.83912(15) 0.1078(7) 0.36383(15) 0.0252(6) Uani 1 1 d . . . . .
H7 H 0.8695 -0.0274 0.3814 0.030 Uiso 1 1 calc R . . . .
C8 C 0.77814(14) 0.1491(6) 0.39220(14) 0.0214(6) Uani 1 1 d . . . . .
C9 C 0.78029(13) -0.1923(6) 0.49059(14) 0.0216(6) Uani 1 1 d . . . . .
H9A H 0.7992 -0.3481 0.4632 0.026 Uiso 1 1 calc R . . . .
H9B H 0.7463 -0.2798 0.5185 0.026 Uiso 1 1 calc R . . . .
C10 C 0.83244(13) -0.0654(6) 0.53525(14) 0.0204(5) Uani 1 1 d . . . . .
C11 C 0.89645(14) -0.1554(6) 0.53356(14) 0.0212(5) Uani 1 1 d . . . . .
C12 C 0.94334(14) -0.0477(7) 0.57657(15) 0.0233(6) Uani 1 1 d . . . . .
H12 H 0.9867 -0.1150 0.5750 0.028 Uiso 1 1 calc R . . . .
C13 C 0.92499(15) 0.1613(7) 0.62203(14) 0.0251(6) Uani 1 1 d . . . . .
C14 C 0.86233(15) 0.2612(7) 0.62481(15) 0.0257(6) Uani 1 1 d . . . . .
H14 H 0.8507 0.4062 0.6560 0.031 Uiso 1 1 calc R . . . .
C15 C 0.81657(14) 0.1470(7) 0.58149(14) 0.0229(6) Uani 1 1 d . . . . .
H15 H 0.7733 0.2151 0.5833 0.027 Uiso 1 1 calc R . . . .
O21 O 0.51924(10) 0.9937(5) 0.34503(11) 0.0268(5) Uani 1 1 d . . . . .
N21 N 0.46406(14) 0.8530(6) 0.43490(13) 0.0252(5) Uani 1 1 d . . . . .
H21A H 0.432(2) 0.846(9) 0.458(2) 0.030(10) Uiso 1 1 d . . . . .
H21B H 0.495(2) 0.746(10) 0.446(2) 0.037(11) Uiso 1 1 d . . . . .
N22 N 0.31364(13) 1.4245(7) 0.37837(14) 0.0315(6) Uani 1 1 d . . . . .
C21 C 0.47054(14) 1.0104(6) 0.38045(14) 0.0217(6) Uani 1 1 d . . . . .
C22 C 0.41785(14) 1.2125(6) 0.36009(14) 0.0204(5) Uani 1 1 d . . . . .
C23 C 0.36164(15) 1.2480(7) 0.39658(16) 0.0273(6) Uani 1 1 d . . . . .
H23 H 0.3573 1.1406 0.4366 0.033 Uiso 1 1 calc R . . . .
C24 C 0.32123(16) 1.5737(7) 0.32195(16) 0.0286(6) Uani 1 1 d . . . . .
H24 H 0.2874 1.7007 0.3084 0.034 Uiso 1 1 calc R . . . .
C25 C 0.37498(15) 1.5550(7) 0.28219(15) 0.0254(6) Uani 1 1 d . . . . .
H25 H 0.3780 1.6655 0.2425 0.030 Uiso 1 1 calc R . . . .
C26 C 0.42447(14) 1.3703(7) 0.30191(14) 0.0227(6) Uani 1 1 d . . . . .
H26 H 0.4623 1.3521 0.2760 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.741(3) . ?
Cl2 C13 1.742(3) . ?
O1 C1 1.215(4) . ?
O2 H2 0.87(6) . ?
O2 C1 1.311(4) . ?
N1 N2 1.350(3) . ?
N1 C8 1.371(4) . ?
N1 C9 1.455(4) . ?
N2 C2 1.327(4) . ?
C1 C2 1.478(4) . ?
C2 C3 1.426(4) . ?
C3 C4 1.412(4) . ?
C3 C8 1.401(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.404(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.513(4) . ?
C10 C11 1.389(4) . ?
C10 C15 1.393(4) . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(4) . ?
C13 C14 1.378(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9500 . ?
O21 C21 1.243(4) . ?
N21 H21A 0.82(4) . ?
N21 H21B 0.83(5) . ?
N21 C21 1.322(4) . ?
N22 C23 1.332(4) . ?
N22 C24 1.338(4) . ?
C21 C22 1.489(4) . ?
C22 C23 1.392(4) . ?
C22 C26 1.386(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.380(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(4) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 117(4) . . ?
N2 N1 C8 111.9(2) . . ?
N2 N1 C9 121.1(2) . . ?
C8 N1 C9 127.0(2) . . ?
C2 N2 N1 106.0(2) . . ?
O1 C1 O2 125.1(3) . . ?
O1 C1 C2 123.7(3) . . ?
O2 C1 C2 111.2(2) . . ?
N2 C2 C1 120.4(3) . . ?
N2 C2 C3 111.6(3) . . ?
C3 C2 C1 128.0(3) . . ?
C4 C3 C2 136.3(3) . . ?
C8 C3 C2 104.0(2) . . ?
C8 C3 C4 119.7(3) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.3(3) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 122.1 . . ?
C6 C7 C8 115.8(3) . . ?
C8 C7 H7 122.1 . . ?
N1 C8 C3 106.6(2) . . ?
N1 C8 C7 130.4(3) . . ?
C3 C8 C7 123.0(3) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
N1 C9 C10 112.3(2) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C11 C10 C9 122.9(3) . . ?
C11 C10 C15 117.3(3) . . ?
C15 C10 C9 119.7(3) . . ?
C10 C11 Cl1 120.0(2) . . ?
C12 C11 Cl1 117.4(2) . . ?
C12 C11 C10 122.6(3) . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.8(3) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 Cl2 118.3(2) . . ?
C14 C13 Cl2 120.0(2) . . ?
C14 C13 C12 121.7(3) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
H21A N21 H21B 116(4) . . ?
C21 N21 H21A 126(3) . . ?
C21 N21 H21B 118(3) . . ?
C23 N22 C24 116.9(3) . . ?
O21 C21 N21 122.1(3) . . ?
O21 C21 C22 118.5(3) . . ?
N21 C21 C22 119.4(3) . . ?
C23 C22 C21 122.8(3) . . ?
C26 C22 C21 118.8(3) . . ?
C26 C22 C23 118.3(3) . . ?
N22 C23 C22 123.5(3) . . ?
N22 C23 H23 118.3 . . ?
C22 C23 H23 118.3 . . ?
N22 C24 H24 117.9 . . ?
N22 C24 C25 124.2(3) . . ?
C25 C24 H24 117.9 . . ?
C24 C25 H25 121.0 . . ?
C24 C25 C26 118.0(3) . . ?
C26 C25 H25 121.0 . . ?
C22 C26 C25 119.0(3) . . ?
C22 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O21 0.87(6) 1.67(6) 2.531(3) 169(6) .
N21 H21A O1 0.82(4) 2.32(4) 2.852(3) 123(3) 3_666
N21 H21B O1 0.83(5) 2.14(5) 2.960(4) 169(4) .
C26 H26 O21 0.95 2.55 3.239(4) 129.4 2_655

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.373
_oxdiff_exptl_absorpt_empirical_full_min 0.281
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9651(7)
2 0.0349(7)

####################################################################### 
# 
# 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_LON-2APYM
_database_code_depnum_ccdc_archive 'CCDC 1531960'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.07.25 svn.r3318 for OlexSys, GUI svn.r5204)
;
_chemical_name_common            ?
_chemical_name_systematic        L3-79-B
_chemical_formula_moiety         'C15 H10 Cl2 N2 O2, 2(C4 H5 N3)'
_chemical_formula_sum            'C23 H20 Cl2 N8 O2'
_chemical_formula_weight         511.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H15 N5 O2 Cl2'
_chemical_oxdiff_usercomment     L3-79-B
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   14.1417(6)
_cell_length_b                   21.6532(8)
_cell_length_c                   7.6525(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.654(4)
_cell_angle_gamma                90
_cell_volume                     2286.39(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5390
_cell_measurement_theta_min      2.8800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -4 -10 0.1125
-7 29 0 0.0705
0 7 10 0.1432
7 -28 0 0.0655
19 7 -2 0.0134
-19 -6 1 0.0350
19 7 -3 0.0076

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.066
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
-1.0865 -3.9571 -9.9696 0.0313 -0.2821 0.9277
-6.9804 29.0107 0.0249 -0.0799 0.9761 0.2670
0.0886 6.9586 9.9727 -0.0273 0.3880 -0.8950
6.9810 -28.0108 -0.0245 0.0664 -0.9467 -0.2622
18.9859 6.9743 -2.0248 -0.9570 -0.1646 -0.1254
-18.9936 -5.9703 1.0282 0.9367 0.1758 0.2231
18.9775 6.9784 -3.0217 -0.9638 -0.1828 -0.0325

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27846
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.886
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  92.00   0.50   37.50    --   14.85  38.00 -60.00  212
  2  ω    -20.00  96.00   0.50   37.50    --   14.85  77.00   0.00  232
  3  ω    -20.00  96.00   0.50   37.50    --   14.85  77.00 120.00  232
  4  ω    -67.00  50.00   0.50   37.50    --   14.85 -77.00 150.00  234
  5  ω    -61.00 -11.00   0.50   37.50    --   14.85 -57.00 -30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0446868000
_diffrn_orient_matrix_UB_12      -0.0135124000
_diffrn_orient_matrix_UB_13      0.0070910000
_diffrn_orient_matrix_UB_21      -0.0175002000
_diffrn_orient_matrix_UB_22      0.0294197000
_diffrn_orient_matrix_UB_23      0.0185300000
_diffrn_orient_matrix_UB_31      -0.0183121000
_diffrn_orient_matrix_UB_32      0.0048764000
_diffrn_orient_matrix_UB_33      -0.0929892000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4160
_reflns_number_total             5218
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.349
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.138
_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)+(0.0340P)²+1.7710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C32(H32),
 C33(H33), C34(H34), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.54682(4) 0.31818(3) 1.38614(8) 0.01790(15) Uani 1 1 d . . . . .
Cl2 Cl 0.30480(5) 0.14117(3) 1.06741(9) 0.02206(16) Uani 1 1 d . . . . .
O2 O 0.26754(13) 0.57189(8) 0.5568(2) 0.0191(4) Uani 1 1 d . . . . .
H2 H 0.279(2) 0.5848(15) 0.462(5) 0.044(11) Uiso 1 1 d . . . . .
O1 O 0.39988(13) 0.51387(8) 0.5641(2) 0.0194(4) Uani 1 1 d . . . . .
N1 N 0.35400(15) 0.45171(9) 1.0403(3) 0.0139(4) Uani 1 1 d . . . . .
N2 N 0.38399(15) 0.46714(9) 0.8907(3) 0.0145(4) Uani 1 1 d . . . . .
C1 C 0.33339(18) 0.53107(11) 0.6289(3) 0.0157(5) Uani 1 1 d . . . . .
C2 C 0.31850(17) 0.50630(10) 0.8008(3) 0.0135(5) Uani 1 1 d . . . . .
C3 C 0.24331(17) 0.51711(10) 0.8941(3) 0.0136(5) Uani 1 1 d . . . . .
C4 C 0.15935(18) 0.55359(11) 0.8687(3) 0.0156(5) Uani 1 1 d . . . . .
H4 H 0.1411 0.5786 0.7681 0.019 Uiso 1 1 calc R . . . .
C5 C 0.10520(18) 0.55124(11) 0.9963(3) 0.0187(6) Uani 1 1 d . . . . .
H5 H 0.0491 0.5749 0.9809 0.022 Uiso 1 1 calc R . . . .
C6 C 0.13200(18) 0.51403(11) 1.1505(3) 0.0182(5) Uani 1 1 d . . . . .
H6 H 0.0934 0.5139 1.2345 0.022 Uiso 1 1 calc R . . . .
C7 C 0.21381(18) 0.47806(11) 1.1792(3) 0.0168(5) Uani 1 1 d . . . . .
H7 H 0.2315 0.4533 1.2804 0.020 Uiso 1 1 calc R . . . .
C8 C 0.26925(17) 0.48041(10) 1.0492(3) 0.0140(5) Uani 1 1 d . . . . .
C9 C 0.41279(18) 0.41031(11) 1.1696(3) 0.0165(5) Uani 1 1 d . . . . .
H9A H 0.4087 0.4229 1.2893 0.020 Uiso 1 1 calc R . . . .
H9B H 0.4799 0.4139 1.1607 0.020 Uiso 1 1 calc R . . . .
C10 C 0.38168(18) 0.34318(11) 1.1420(3) 0.0137(5) Uani 1 1 d . . . . .
C11 C 0.44125(17) 0.29742(11) 1.2345(3) 0.0136(5) Uani 1 1 d . . . . .
C12 C 0.41853(18) 0.23524(10) 1.2131(3) 0.0142(5) Uani 1 1 d . . . . .
H12 H 0.4594 0.2053 1.2759 0.017 Uiso 1 1 calc R . . . .
C13 C 0.33353(18) 0.21917(11) 1.0958(3) 0.0153(5) Uani 1 1 d . . . . .
C14 C 0.27118(18) 0.26310(11) 1.0033(3) 0.0167(5) Uani 1 1 d . . . . .
H14 H 0.2134 0.2515 0.9267 0.020 Uiso 1 1 calc R . . . .
C15 C 0.29675(18) 0.32487(11) 1.0273(3) 0.0161(5) Uani 1 1 d . . . . .
H15 H 0.2556 0.3547 0.9645 0.019 Uiso 1 1 calc R . . . .
N31 N 0.04717(16) 0.16888(10) 1.2356(3) 0.0227(5) Uani 1 1 d . . . . .
N32 N 0.03974(16) 0.17184(10) 0.9189(3) 0.0222(5) Uani 1 1 d . . . . .
N33 N 0.01918(18) 0.25972(11) 1.0752(3) 0.0257(5) Uani 1 1 d . . . . .
H33A H 0.0245(19) 0.2822(12) 1.187(4) 0.020(7) Uiso 1 1 d . . . . .
H33B H 0.022(2) 0.2831(14) 0.971(4) 0.036(9) Uiso 1 1 d . . . . .
C31 C 0.03589(19) 0.19844(12) 1.0777(3) 0.0200(6) Uani 1 1 d . . . . .
C32 C 0.06521(19) 0.10832(12) 1.2311(4) 0.0225(6) Uani 1 1 d . . . . .
H32 H 0.0744 0.0863 1.3378 0.027 Uiso 1 1 calc R . . . .
C33 C 0.07096(19) 0.07679(12) 1.0779(4) 0.0226(6) Uani 1 1 d . . . . .
H33 H 0.0833 0.0346 1.0785 0.027 Uiso 1 1 calc R . . . .
C34 C 0.05742(19) 0.11135(12) 0.9237(4) 0.0232(6) Uani 1 1 d . . . . .
H34 H 0.0608 0.0915 0.8175 0.028 Uiso 1 1 calc R . . . .
N21 N 0.38569(16) 0.64670(9) 0.0351(3) 0.0185(5) Uani 1 1 d . . . . .
N22 N 0.30180(15) 0.62695(9) 0.2701(3) 0.0153(4) Uani 1 1 d . . . . .
N23 N 0.44277(17) 0.57611(10) 0.2566(3) 0.0173(5) Uani 1 1 d . . . . .
H23A H 0.488(2) 0.5692(13) 0.212(4) 0.026(9) Uiso 1 1 d . . . . .
H23B H 0.438(2) 0.5579(14) 0.351(4) 0.034(9) Uiso 1 1 d . . . . .
C21 C 0.37546(18) 0.61716(11) 0.1865(3) 0.0155(5) Uani 1 1 d . . . . .
C22 C 0.31772(19) 0.68755(11) -0.0315(4) 0.0208(6) Uani 1 1 d . . . . .
H22 H 0.3227 0.7086 -0.1351 0.025 Uiso 1 1 calc R . . . .
C23 C 0.23934(19) 0.70076(11) 0.0446(4) 0.0207(6) Uani 1 1 d . . . . .
H23 H 0.1926 0.7297 -0.0050 0.025 Uiso 1 1 calc R . . . .
C24 C 0.23494(19) 0.66865(11) 0.1967(3) 0.0193(6) Uani 1 1 d . . . . .
H24 H 0.1834 0.6761 0.2513 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.738(2) . ?
Cl2 C13 1.739(2) . ?
O2 H2 0.83(4) . ?
O2 C1 1.314(3) . ?
O1 C1 1.213(3) . ?
N1 N2 1.347(3) . ?
N1 C8 1.365(3) . ?
N1 C9 1.453(3) . ?
N2 C2 1.331(3) . ?
C1 C2 1.478(3) . ?
C2 C3 1.424(3) . ?
C3 C4 1.404(3) . ?
C3 C8 1.408(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.410(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.372(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.520(3) . ?
C10 C11 1.390(3) . ?
C10 C15 1.382(3) . ?
C11 C12 1.385(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9300 . ?
N31 C31 1.346(3) . ?
N31 C32 1.338(3) . ?
N32 C31 1.357(3) . ?
N32 C34 1.333(3) . ?
N33 H33A 0.97(3) . ?
N33 H33B 0.95(3) . ?
N33 C31 1.347(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.375(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.374(4) . ?
C34 H34 0.9300 . ?
N21 C21 1.359(3) . ?
N21 C22 1.324(3) . ?
N22 C21 1.353(3) . ?
N22 C24 1.339(3) . ?
N23 H23A 0.80(3) . ?
N23 H23B 0.84(3) . ?
N23 C21 1.327(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.369(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
C1 O2 H2 110(2) . . ?
N2 N1 C8 111.88(19) . . ?
N2 N1 C9 119.4(2) . . ?
C8 N1 C9 128.7(2) . . ?
C2 N2 N1 106.5(2) . . ?
O2 C1 C2 113.0(2) . . ?
O1 C1 O2 125.2(2) . . ?
O1 C1 C2 121.8(2) . . ?
N2 C2 C1 118.2(2) . . ?
N2 C2 C3 110.9(2) . . ?
C3 C2 C1 130.9(2) . . ?
C4 C3 C2 136.4(2) . . ?
C4 C3 C8 119.4(2) . . ?
C8 C3 C2 104.2(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.9(2) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.6 . . ?
C6 C7 C8 116.8(2) . . ?
C8 C7 H7 121.6 . . ?
N1 C8 C3 106.5(2) . . ?
N1 C8 C7 130.9(2) . . ?
C7 C8 C3 122.5(2) . . ?
N1 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
N1 C9 C10 113.0(2) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C11 C10 C9 119.1(2) . . ?
C15 C10 C9 123.2(2) . . ?
C15 C10 C11 117.7(2) . . ?
C10 C11 Cl1 119.47(18) . . ?
C12 C11 Cl1 118.26(18) . . ?
C12 C11 C10 122.3(2) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.0(2) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 Cl2 118.23(18) . . ?
C12 C13 C14 121.8(2) . . ?
C14 C13 Cl2 119.94(19) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.5(2) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 C14 121.7(2) . . ?
C10 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C32 N31 C31 115.4(2) . . ?
C34 N32 C31 115.9(2) . . ?
H33A N33 H33B 117(2) . . ?
C31 N33 H33A 120.1(16) . . ?
C31 N33 H33B 119.7(18) . . ?
N31 C31 N32 125.6(2) . . ?
N31 C31 N33 117.8(2) . . ?
N33 C31 N32 116.6(2) . . ?
N31 C32 H32 118.1 . . ?
N31 C32 C33 123.8(2) . . ?
C33 C32 H32 118.1 . . ?
C32 C33 H33 122.0 . . ?
C34 C33 C32 116.0(2) . . ?
C34 C33 H33 122.0 . . ?
N32 C34 C33 123.3(3) . . ?
N32 C34 H34 118.3 . . ?
C33 C34 H34 118.3 . . ?
C22 N21 C21 116.1(2) . . ?
C24 N22 C21 117.0(2) . . ?
H23A N23 H23B 120(3) . . ?
C21 N23 H23A 121(2) . . ?
C21 N23 H23B 119(2) . . ?
N22 C21 N21 124.5(2) . . ?
N23 C21 N21 117.3(2) . . ?
N23 C21 N22 118.2(2) . . ?
N21 C22 H22 118.2 . . ?
N21 C22 C23 123.7(2) . . ?
C23 C22 H22 118.2 . . ?
C22 C23 H23 121.9 . . ?
C24 C23 C22 116.1(2) . . ?
C24 C23 H23 121.9 . . ?
N22 C24 C23 122.7(2) . . ?
N22 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N22 0.83(4) 1.82(4) 2.634(3) 170(3) .
N33 H33A N32 0.97(3) 2.00(3) 2.977(3) 178(2) 4_566
N33 H33B N31 0.95(3) 2.18(3) 3.123(3) 173(3) 4_565
N23 H23A N2 0.80(3) 2.27(3) 3.059(3) 170(3) 3_666
N23 H23B O1 0.84(3) 2.06(3) 2.890(3) 169(3) .

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-13
_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 2.002
_oxdiff_exptl_absorpt_empirical_full_min 0.604
####################################################################### 
# 
# 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_LON-IMID_2-1
_database_code_depnum_ccdc_archive 'CCDC 1531963'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2017-01-13
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H9.5 Cl2 N2 O2), C3 H5 N2'
_chemical_formula_sum            'C33 H24 Cl4 N6 O4'
_chemical_formula_weight         710.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.3787(7)
_cell_length_b                   11.8719(9)
_cell_length_c                   14.0409(8)
_cell_angle_alpha                105.139(6)
_cell_angle_beta                 91.651(5)
_cell_angle_gamma                91.906(6)
_cell_volume                     1667.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8830
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4780
_cell_measurement_theta_min      3.3510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.679
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.224
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12547
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.428
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray'
_diffrn_source_current           0.8
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10487
_reflns_number_total             12547
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 _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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         1.329
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         12547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0717
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1092P)²+1.8855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2024
_refine_ls_wR_factor_ref         0.2092
_refine_special_details          
'Non-merohedral twin at approximately 36%. Voids (110A^3) present which may contain MeOH or acetonitrile solvent or water molecules. Electron count not possible due to twinned structure.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6391(14) 0.3609(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3. Others
 Fixed Sof: H1(0.5) H21(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C29(H29A,H29B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C24(H24),
 C25(H25), C26(H26), C27(H27), C32(H32), C34(H34), C35(H35), C41(H41A),
 C42(H42A), C43(H43)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O21(H21)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.06282(9) 0.28739(8) 0.08240(7) 0.0334(2) Uani 1 1 d . . . . .
Cl2 Cl -0.10042(16) 0.75304(11) 0.18514(9) 0.0642(4) Uani 1 1 d . . . . .
O1 O 0.4456(2) 0.4663(2) 0.41618(19) 0.0307(6) Uani 1 1 d . . . . .
H1 H 0.4873 0.4863 0.4705 0.046 Uiso 0.5 1 calc GR . P . .
O2 O 0.4537(3) 0.2901(3) 0.4430(2) 0.0405(7) Uani 1 1 d . . . . .
N1 N 0.2697(3) 0.2914(3) 0.1517(2) 0.0305(7) Uani 1 1 d . . . . .
N2 N 0.3348(3) 0.3651(3) 0.2298(2) 0.0286(7) Uani 1 1 d . . . . .
C1 C 0.4250(3) 0.3551(3) 0.3911(3) 0.0277(7) Uani 1 1 d . . . . .
C2 C 0.3588(3) 0.3020(3) 0.2929(3) 0.0282(7) Uani 1 1 d . . . . .
C3 C 0.3065(4) 0.1870(4) 0.2575(3) 0.0398(9) Uani 1 1 d . . . . .
C4 C 0.2937(7) 0.0878(4) 0.2940(4) 0.0722(19) Uani 1 1 d . . . . .
H4 H 0.3329 0.0872 0.3558 0.087 Uiso 1 1 calc R . . . .
C5 C 0.2234(9) -0.0083(5) 0.2386(5) 0.096(3) Uani 1 1 d . . . . .
H5 H 0.2125 -0.0750 0.2634 0.115 Uiso 1 1 calc R . . . .
C6 C 0.1671(8) -0.0100(5) 0.1454(5) 0.088(2) Uani 1 1 d . . . . .
H6 H 0.1193 -0.0779 0.1087 0.105 Uiso 1 1 calc R . . . .
C7 C 0.1802(6) 0.0848(4) 0.1069(4) 0.0576(14) Uani 1 1 d . . . . .
H7 H 0.1443 0.0831 0.0436 0.069 Uiso 1 1 calc R . . . .
C8 C 0.2484(4) 0.1837(4) 0.1646(3) 0.0375(9) Uani 1 1 d . . . . .
C9 C 0.2282(4) 0.3351(4) 0.0673(3) 0.0359(9) Uani 1 1 d . . . . .
H9A H 0.1805 0.2714 0.0178 0.043 Uiso 1 1 calc R . . . .
H9B H 0.3053 0.3582 0.0359 0.043 Uiso 1 1 calc R . . . .
C10 C 0.1438(4) 0.4375(4) 0.0968(2) 0.0313(8) Uani 1 1 d . . . . .
C11 C 0.0117(4) 0.4264(3) 0.1066(3) 0.0299(8) Uani 1 1 d . . . . .
C12 C -0.0655(4) 0.5215(4) 0.1339(3) 0.0338(8) Uani 1 1 d . . . . .
H12 H -0.1558 0.5114 0.1400 0.041 Uiso 1 1 calc R . . . .
C13 C -0.0067(5) 0.6314(4) 0.1519(3) 0.0435(11) Uani 1 1 d . . . . .
C14 C 0.1245(5) 0.6471(4) 0.1435(3) 0.0513(13) Uani 1 1 d . . . . .
H14 H 0.1632 0.7235 0.1568 0.062 Uiso 1 1 calc R . . . .
C15 C 0.1987(5) 0.5504(4) 0.1156(3) 0.0416(11) Uani 1 1 d . . . . .
H15 H 0.2888 0.5610 0.1090 0.050 Uiso 1 1 calc R . . . .
Cl21 Cl 1.03017(9) 0.31571(11) 1.33219(8) 0.0426(3) Uani 1 1 d . . . . .
Cl22 Cl 1.18579(13) 0.76680(13) 1.40714(9) 0.0572(3) Uani 1 1 d . . . . .
O21 O 0.5552(3) 0.4751(3) 1.0713(2) 0.0368(6) Uani 1 1 d . . . . .
H21 H 0.5301 0.4888 1.0182 0.055 Uiso 0.5 1 calc GR . P . .
O22 O 0.5358(3) 0.2895(3) 0.9800(2) 0.0416(7) Uani 1 1 d . . . . .
N21 N 0.6650(3) 0.4045(3) 1.2242(2) 0.0306(7) Uani 1 1 d . . . . .
N23 N 0.7120(3) 0.3418(3) 1.2849(2) 0.0338(7) Uani 1 1 d . . . . .
C21 C 0.5675(3) 0.3642(3) 1.0575(3) 0.0319(8) Uani 1 1 d . . . . .
C22 C 0.6235(3) 0.3265(3) 1.1424(3) 0.0301(8) Uani 1 1 d . . . . .
C23 C 0.6420(3) 0.2096(4) 1.1475(3) 0.0313(8) Uani 1 1 d . . . . .
C24 C 0.6192(4) 0.0976(4) 1.0854(4) 0.0422(10) Uani 1 1 d . . . . .
H24 H 0.5807 0.0859 1.0212 0.051 Uiso 1 1 calc R . . . .
C25 C 0.6547(5) 0.0039(5) 1.1209(4) 0.0533(12) Uani 1 1 d . . . . .
H25 H 0.6399 -0.0733 1.0801 0.064 Uiso 1 1 calc R . . . .
C26 C 0.7119(5) 0.0206(5) 1.2156(4) 0.0552(13) Uani 1 1 d . . . . .
H26 H 0.7352 -0.0457 1.2371 0.066 Uiso 1 1 calc R . . . .
C27 C 0.7351(4) 0.1299(5) 1.2781(4) 0.0460(11) Uani 1 1 d . . . . .
H27 H 0.7736 0.1407 1.3423 0.055 Uiso 1 1 calc R . . . .
C28 C 0.6994(3) 0.2248(4) 1.2430(3) 0.0350(9) Uani 1 1 d . . . . .
C29 C 0.7600(4) 0.4022(4) 1.3846(3) 0.0406(10) Uani 1 1 d . . . . .
H29A H 0.7919 0.3439 1.4177 0.049 Uiso 1 1 calc R . . . .
H29B H 0.6876 0.4412 1.4226 0.049 Uiso 1 1 calc R . . . .
C30 C 0.8665(4) 0.4917(4) 1.3867(3) 0.0389(10) Uani 1 1 d . . . . .
C31 C 0.9929(4) 0.4615(4) 1.3656(3) 0.0355(9) Uani 1 1 d . . . . .
C32 C 1.0921(4) 0.5450(4) 1.3706(3) 0.0400(10) Uani 1 1 d . . . . .
H32 H 1.1777 0.5227 1.3552 0.048 Uiso 1 1 calc R . . . .
C33 C 1.0625(4) 0.6597(5) 1.3982(3) 0.0427(10) Uani 1 1 d . . . . .
C34 C 0.9392(5) 0.6953(5) 1.4195(3) 0.0484(11) Uani 1 1 d . . . . .
H34 H 0.9210 0.7759 1.4377 0.058 Uiso 1 1 calc R . . . .
C35 C 0.8421(4) 0.6099(5) 1.4136(3) 0.0456(11) Uani 1 1 d . . . . .
H35 H 0.7566 0.6331 1.4283 0.055 Uiso 1 1 calc R . . . .
N41 N 0.4951(4) 0.2881(4) 0.6322(3) 0.0421(9) Uani 1 1 d . . . . .
N42 N 0.5050(4) 0.2823(4) 0.7828(3) 0.0506(10) Uani 1 1 d . . . . .
H42 H 0.505(5) 0.287(5) 0.849(4) 0.061 Uiso 1 1 d R . . . .
C41 C 0.4994(5) 0.3563(5) 0.7242(4) 0.0515(12) Uani 1 1 d . . . . .
H41A H 0.4988 0.4391 0.7443 0.062 Uiso 1 1 calc R . . . .
C42 C 0.5069(7) 0.1721(5) 0.7252(5) 0.0701(17) Uani 1 1 d . . . . .
H42A H 0.5119 0.1033 0.7474 0.084 Uiso 1 1 calc R . . . .
C43 C 0.5005(6) 0.1771(6) 0.6337(5) 0.0716(17) Uani 1 1 d . . . . .
H43 H 0.4998 0.1120 0.5773 0.086 Uiso 1 1 calc R . . . .
H41 H 0.488(6) 0.303(6) 0.585(5) 0.08(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.745(4) . ?
Cl2 C13 1.737(5) . ?
O1 H1 0.8400 . ?
O1 C1 1.283(5) . ?
O2 C1 1.230(5) . ?
N1 N2 1.357(4) . ?
N1 C8 1.350(5) . ?
N1 C9 1.471(5) . ?
N2 C2 1.324(5) . ?
C1 C2 1.494(5) . ?
C2 C3 1.410(6) . ?
C3 C4 1.405(7) . ?
C3 C8 1.412(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.413(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.374(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.498(6) . ?
C10 C11 1.387(5) . ?
C10 C15 1.395(6) . ?
C11 C12 1.384(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(6) . ?
C13 C14 1.380(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(8) . ?
C15 H15 0.9500 . ?
Cl21 C31 1.731(5) . ?
Cl22 C33 1.752(5) . ?
O21 H21 0.8400 . ?
O21 C21 1.291(5) . ?
O22 C21 1.238(5) . ?
N21 N23 1.360(4) . ?
N21 C22 1.324(5) . ?
N23 C28 1.360(6) . ?
N23 C29 1.461(5) . ?
C21 C22 1.489(5) . ?
C22 C23 1.426(5) . ?
C23 C24 1.395(6) . ?
C23 C28 1.417(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.403(7) . ?
C26 H26 0.9500 . ?
C26 C27 1.374(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.399(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.502(6) . ?
C30 C31 1.391(6) . ?
C30 C35 1.388(7) . ?
C31 C32 1.393(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.363(7) . ?
C33 C34 1.379(6) . ?
C34 H34 0.9500 . ?
C34 C35 1.390(7) . ?
C35 H35 0.9500 . ?
N41 C41 1.331(6) . ?
N41 C43 1.327(8) . ?
N41 H41 0.73(7) . ?
N42 H42 0.92(6) . ?
N42 C41 1.353(7) . ?
N42 C42 1.347(7) . ?
C41 H41A 0.9500 . ?
C42 H42A 0.9500 . ?
C42 C43 1.302(8) . ?
C43 H43 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
N2 N1 C9 119.3(3) . . ?
C8 N1 N2 112.6(3) . . ?
C8 N1 C9 128.0(3) . . ?
C2 N2 N1 105.6(3) . . ?
O1 C1 C2 117.4(3) . . ?
O2 C1 O1 124.5(3) . . ?
O2 C1 C2 118.1(4) . . ?
N2 C2 C1 121.3(3) . . ?
N2 C2 C3 111.4(3) . . ?
C3 C2 C1 127.1(4) . . ?
C2 C3 C8 104.6(4) . . ?
C4 C3 C2 136.4(4) . . ?
C4 C3 C8 118.9(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(5) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(6) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.1(5) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.5(4) . . ?
C8 C7 H7 121.3 . . ?
N1 C8 C3 105.8(3) . . ?
N1 C8 C7 131.8(4) . . ?
C7 C8 C3 122.3(4) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
N1 C9 C10 112.5(3) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C11 C10 C9 123.2(4) . . ?
C11 C10 C15 117.3(4) . . ?
C15 C10 C9 119.4(4) . . ?
C10 C11 Cl1 119.5(3) . . ?
C12 C11 Cl1 117.7(3) . . ?
C12 C11 C10 122.9(4) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 117.6(4) . . ?
C13 C12 H12 121.2 . . ?
C12 C13 Cl2 119.1(4) . . ?
C14 C13 Cl2 119.2(4) . . ?
C14 C13 C12 121.7(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C21 O21 H21 109.5 . . ?
C22 N21 N23 105.6(3) . . ?
N21 N23 C28 112.0(3) . . ?
N21 N23 C29 119.7(4) . . ?
C28 N23 C29 128.2(3) . . ?
O21 C21 C22 116.1(3) . . ?
O22 C21 O21 124.6(3) . . ?
O22 C21 C22 119.2(4) . . ?
N21 C22 C21 120.7(3) . . ?
N21 C22 C23 112.3(3) . . ?
C23 C22 C21 127.0(4) . . ?
C24 C23 C22 136.8(4) . . ?
C24 C23 C28 120.0(4) . . ?
C28 C23 C22 103.2(4) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 C23 117.7(4) . . ?
C25 C24 H24 121.2 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.5(5) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.0 . . ?
C27 C26 C25 122.0(4) . . ?
C27 C26 H26 119.0 . . ?
C26 C27 H27 121.6 . . ?
C26 C27 C28 116.8(4) . . ?
C28 C27 H27 121.6 . . ?
N23 C28 C23 106.9(3) . . ?
N23 C28 C27 131.1(4) . . ?
C27 C28 C23 122.0(4) . . ?
N23 C29 H29A 108.9 . . ?
N23 C29 H29B 108.9 . . ?
N23 C29 C30 113.4(3) . . ?
H29A C29 H29B 107.7 . . ?
C30 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C31 C30 C29 122.4(4) . . ?
C35 C30 C29 120.3(4) . . ?
C35 C30 C31 117.3(4) . . ?
C30 C31 Cl21 119.7(3) . . ?
C30 C31 C32 122.2(4) . . ?
C32 C31 Cl21 118.1(3) . . ?
C31 C32 H32 121.1 . . ?
C33 C32 C31 117.9(4) . . ?
C33 C32 H32 121.1 . . ?
C32 C33 Cl22 118.9(3) . . ?
C32 C33 C34 122.7(4) . . ?
C34 C33 Cl22 118.4(4) . . ?
C33 C34 H34 121.0 . . ?
C33 C34 C35 118.1(5) . . ?
C35 C34 H34 121.0 . . ?
C30 C35 C34 121.9(4) . . ?
C30 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
C41 N41 H41 130(5) . . ?
C43 N41 C41 109.8(5) . . ?
C43 N41 H41 120(5) . . ?
C41 N42 H42 138(4) . . ?
C42 N42 H42 114(4) . . ?
C42 N42 C41 108.7(4) . . ?
N41 C41 N42 105.2(5) . . ?
N41 C41 H41A 127.4 . . ?
N42 C41 H41A 127.4 . . ?
N42 C42 H42A 126.2 . . ?
C43 C42 N42 107.6(5) . . ?
C43 C42 H42A 126.2 . . ?
N41 C43 H43 125.7 . . ?
C42 C43 N41 108.6(6) . . ?
C42 C43 H43 125.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.84 1.67 2.502(5) 173.2 2_666
O1 H1 O2 0.84 2.66 3.171(4) 120.8 2_666
C9 H9A Cl2 0.99 2.88 3.622(4) 132.1 2_565
C9 H9B O22 0.99 2.63 3.461(5) 141.9 1_554
C12 H12 N21 0.95 2.69 3.497(5) 143.4 1_454
O21 H21 O21 0.84 1.67 2.490(5) 164.9 2_667
C29 H29B O1 0.99 2.54 3.390(5) 143.7 1_556
N42 H42 O22 0.92(6) 1.85(6) 2.757(5) 170(5) .
C41 H41A O21 0.95 2.61 3.121(6) 114.3 2_667
C41 H41A N21 0.95 2.52 3.290(6) 138.1 2_667
N41 H41 O2 0.73(7) 1.99(7) 2.685(5) 161(7) .

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_original_sample_id L3-85-C2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6391(14)
2 0.3609(14)

_vrf_PLAT601_2015lms048b         
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of 110 Ang3  
RESPONSE: May contain MeOH / acetonitrile solvent or water molecules from synthesis. Due to twin electron count is not possible using SQUUEZE or solvent masking algorothms in Olex2 to give better indication of solvent nature. No hydrogen bonnding to main construct and molecules may be disordered.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
# 
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# 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_a-LON
_database_code_depnum_ccdc_archive 'CCDC 1531953'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl2 N2 O2'
_chemical_formula_sum            'C15 H10 Cl2 N2 O2'
_chemical_formula_weight         321.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H25 N3 O3'
_chemical_oxdiff_usercomment     L4-23-A2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   19.3743(10)
_cell_length_b                   4.7313(2)
_cell_length_c                   14.6770(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.886(4)
_cell_angle_gamma                90
_cell_volume                     1344.65(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3810
_cell_measurement_theta_min      3.5250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-27 0 -1 0.0138
27 0 1 0.0138
1 7 5 0.1196
4 -1 -20 0.0060
-4 1 20 0.0060
2 -6 -5 0.1747

_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.012
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
-27.0226 -0.0195 -1.0063 -0.2402 -0.9163 0.2972
27.0226 0.0195 1.0063 0.2402 0.9163 -0.2972
0.9077 6.9961 4.9675 0.0960 0.3616 1.0087
4.0639 -0.9876 -19.9742 -0.8941 0.1939 -0.3606
-4.0639 0.9876 19.9742 0.8941 -0.1939 0.3606
2.0835 -5.9942 -4.9706 -0.0956 -0.2086 -0.9033

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9905
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.777
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  52.00   0.50  250.00    --   15.17 -28.00-149.00  166
  2  ω    -47.00   5.00   0.50  250.00    --  -15.79  28.00  12.00  104
  3  ω    -50.00  37.00   0.50  250.00    --   15.17 -38.00-180.00  174
  4  ω    -16.00  91.00   0.50  250.00    --   15.17  57.00-180.00  214
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  SuperNova
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0071462000
_diffrn_orient_matrix_UB_12      -0.0207495000
_diffrn_orient_matrix_UB_13      0.0472407000
_diffrn_orient_matrix_UB_21      0.0340696000
_diffrn_orient_matrix_UB_22      0.0510297000
_diffrn_orient_matrix_UB_23      -0.0052983000
_diffrn_orient_matrix_UB_31      -0.0114293000
_diffrn_orient_matrix_UB_32      0.1393924000
_diffrn_orient_matrix_UB_33      0.0088346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2352
_reflns_number_total             3074
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.663
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+1.0802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1439
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.86324(4) 0.64255(18) 0.38949(5) 0.0295(2) Uani 1 1 d . . . . .
Cl2 Cl 0.97344(4) 0.01513(17) 0.66265(6) 0.0307(2) Uani 1 1 d . . . . .
O1 O 0.58019(11) 0.1385(5) 0.55337(14) 0.0202(5) Uani 1 1 d . . . . .
H1 H 0.552(2) 0.022(9) 0.556(3) 0.041(12) Uiso 1 1 d . . . . .
O2 O 0.51718(10) 0.2473(4) 0.42657(13) 0.0187(5) Uani 1 1 d . . . . .
N1 N 0.70905(12) 0.7587(5) 0.47873(16) 0.0169(5) Uani 1 1 d . . . . .
N2 N 0.67156(12) 0.5527(5) 0.51744(16) 0.0173(5) Uani 1 1 d . . . . .
C1 C 0.56810(14) 0.2828(6) 0.47878(19) 0.0153(6) Uani 1 1 d . . . . .
C2 C 0.61918(14) 0.5004(6) 0.45868(19) 0.0152(6) Uani 1 1 d . . . . .
C3 C 0.62201(14) 0.6730(6) 0.37951(19) 0.0169(6) Uani 1 1 d . . . . .
C4 C 0.58336(15) 0.7047(6) 0.2973(2) 0.0199(6) Uani 1 1 d . . . . .
H4 H 0.5435 0.5929 0.2846 0.024 Uiso 1 1 calc R . . . .
C5 C 0.60511(15) 0.9021(7) 0.2360(2) 0.0209(6) Uani 1 1 d . . . . .
H5 H 0.5799 0.9247 0.1799 0.025 Uiso 1 1 calc R . . . .
C6 C 0.66352(16) 1.0717(7) 0.2537(2) 0.0225(7) Uani 1 1 d . . . . .
H6 H 0.6763 1.2074 0.2096 0.027 Uiso 1 1 calc R . . . .
C7 C 0.70288(15) 1.0462(6) 0.3337(2) 0.0193(6) Uani 1 1 d . . . . .
H7 H 0.7424 1.1604 0.3460 0.023 Uiso 1 1 calc R . . . .
C8 C 0.68096(14) 0.8419(6) 0.39561(19) 0.0162(6) Uani 1 1 d . . . . .
C9 C 0.76591(14) 0.8877(6) 0.5312(2) 0.0195(6) Uani 1 1 d . . . . .
H9A H 0.7475 0.9846 0.5850 0.023 Uiso 1 1 calc R . . . .
H9B H 0.7883 1.0318 0.4932 0.023 Uiso 1 1 calc R . . . .
C10 C 0.81892(14) 0.6730(6) 0.5626(2) 0.0178(6) Uani 1 1 d . . . . .
C11 C 0.86515(15) 0.5498(6) 0.5043(2) 0.0200(6) Uani 1 1 d . . . . .
C12 C 0.91328(15) 0.3476(7) 0.5338(2) 0.0227(7) Uani 1 1 d . . . . .
H12 H 0.9444 0.2657 0.4926 0.027 Uiso 1 1 calc R . . . .
C13 C 0.91438(15) 0.2704(6) 0.6237(2) 0.0228(7) Uani 1 1 d . . . . .
C14 C 0.86933(15) 0.3858(7) 0.6847(2) 0.0226(7) Uani 1 1 d . . . . .
H14 H 0.8706 0.3283 0.7468 0.027 Uiso 1 1 calc R . . . .
C15 C 0.82229(15) 0.5876(7) 0.6534(2) 0.0203(6) Uani 1 1 d . . . . .
H15 H 0.7916 0.6697 0.6950 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.741(3) . ?
Cl2 C13 1.747(3) . ?
O1 H1 0.78(4) . ?
O1 C1 1.305(3) . ?
O2 C1 1.240(3) . ?
N1 N2 1.352(3) . ?
N1 C8 1.377(4) . ?
N1 C9 1.457(3) . ?
N2 C2 1.333(3) . ?
C1 C2 1.465(4) . ?
C2 C3 1.423(4) . ?
C3 C4 1.407(4) . ?
C3 C8 1.407(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.506(4) . ?
C10 C11 1.387(4) . ?
C10 C15 1.392(4) . ?
C11 C12 1.395(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.370(4) . ?
C13 C14 1.383(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(4) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 108(3) . . ?
N2 N1 C8 112.1(2) . . ?
N2 N1 C9 119.2(2) . . ?
C8 N1 C9 128.2(2) . . ?
C2 N2 N1 105.7(2) . . ?
O1 C1 C2 115.6(2) . . ?
O2 C1 O1 124.4(3) . . ?
O2 C1 C2 120.0(3) . . ?
N2 C2 C1 120.3(3) . . ?
N2 C2 C3 111.9(2) . . ?
C3 C2 C1 127.8(3) . . ?
C4 C3 C2 136.7(3) . . ?
C4 C3 C8 119.3(3) . . ?
C8 C3 C2 104.0(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 122.0 . . ?
C6 C7 C8 116.1(3) . . ?
C8 C7 H7 122.0 . . ?
N1 C8 C3 106.4(2) . . ?
N1 C8 C7 130.7(3) . . ?
C7 C8 C3 123.0(3) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
N1 C9 C10 112.0(2) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C11 C10 C9 122.9(3) . . ?
C11 C10 C15 117.2(3) . . ?
C15 C10 C9 119.9(3) . . ?
C10 C11 Cl1 119.8(2) . . ?
C10 C11 C12 122.4(3) . . ?
C12 C11 Cl1 117.7(2) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.1(3) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 Cl2 119.3(2) . . ?
C12 C13 C14 121.9(3) . . ?
C14 C13 Cl2 118.8(2) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.8(3) . . ?
C14 C15 H15 119.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.78(4) 1.88(4) 2.649(3) 175(4) 3_656

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-23
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_original_sample_id 'L4-23-A2; alpha lon'
_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 1.976
_oxdiff_exptl_absorpt_empirical_full_min 0.259
####################################################################### 
# 
# 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_LON-44BIPY
_database_code_depnum_ccdc_archive 'CCDC 1531949'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H10 Cl2 N2 O2), C10 H8 N2'
_chemical_formula_sum            'C40 H28 Cl4 N6 O4'
_chemical_formula_weight         798.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C80 H61 Cl8 N12 O8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   32.6725(11)
_cell_length_b                   26.2388(13)
_cell_length_c                   8.6827(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.879(3)
_cell_angle_gamma                90
_cell_volume                     7426.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10551
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.4860
_cell_measurement_theta_min      2.4080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3280
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.1148
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            50025
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.552
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  73.00   1.00   55.00    --  -17.00  18.00-180.00  117
  2  ω    -62.00  19.00   1.00   55.00    --  -17.00 -54.00   0.00   81
  3  ω    -36.00  -5.00   1.00   55.00    --  -17.00 -72.00 120.00   31
  4  ω   -107.00 -50.00   1.00   55.00    --  -17.00 -18.00   0.00   57
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC10 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0150127000
_diffrn_orient_matrix_UB_12      -0.0007301000
_diffrn_orient_matrix_UB_13      0.0628750000
_diffrn_orient_matrix_UB_21      -0.0016794000
_diffrn_orient_matrix_UB_22      0.0267872000
_diffrn_orient_matrix_UB_23      0.0086421000
_diffrn_orient_matrix_UB_31      -0.0156667000
_diffrn_orient_matrix_UB_32      -0.0035652000
_diffrn_orient_matrix_UB_33      0.0517003000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8935
_reflns_number_total             17020
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.578
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1073
_refine_ls_number_reflns         17020
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0758
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0815P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1740
_refine_special_details          
'Disorder present in the di-chlorine substituted aromatic ring in all 4 moeities of lonidamine in ratios of 93:7, 88:12, 94:6 and 91:9. All carbon atoms in the minor components are modelled isotropically due to small electron densities. Various restraints and constraints have been used to give best representation of structure. Channels are present which may contain solvent molecules (DMF used in crystallisation) or water and are likely to be disordered due to lack of hydorgen bonding. Electron count indicates 40-44 electrons per void space, indicative of DMF solvent'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H27-H29D = H27-H29C
 -2.1 with sigma of 0.02
 O41-H41
 0.98 with sigma of 0.02
 C70-C69 \\sim C70A-C69A
 with sigma of 0.02
 N61-C69 \\sim N61-C69A
 with sigma of 0.02
 N41-C49 \\sim N41-C49A
 with sigma of 0.02
 C50-C49 \\sim C50A-C49A
 with sigma of 0.02
 N1-C9A \\sim N1-C9
 with sigma of 0.02
 Cl1-C11 \\sim Cl1A-C11A
 with sigma of 0.02
 C10-C9 \\sim C9A-C10A
 with sigma of 0.02
 C9A-N1 \\sim C9A-C10A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C69 \\sim C69A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C49A \\sim C49: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C9 \\sim C9A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C29 \\sim C29A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uiso(C52A) = Uiso(C53A) = Uiso(C54A) = Uiso(C55A) = Uiso(C50A) = Uiso(C51A) =
Uiso(C49A)
Uanis(Cl42) = Uanis(Cl)
Uanis(Cl41) = Uanis(Cl5)
Uanis(Cl61) = Uanis(Cl6)
Uiso(C70A) = Uiso(C71A) = Uiso(C72A) = Uiso(C73A) = Uiso(C74A) = Uiso(C75A)
Uiso(C10A) = Uiso(C11A) = Uiso(C15A) = Uiso(C14A) = Uiso(C13A) = Uiso(C12A)
Uiso(C30A) = Uiso(C35A) = Uiso(C34A) = Uiso(C33A) = Uiso(C31A) = Uiso(C32A)
Uanis(Cl21) = Uanis(Cl3)
Uanis(Cl22) = Uanis(Cl4)
Uiso(C29A) = Uiso(C30A)
4. Rigid body (RIGU) restrains
 C69, C69A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C49A, C49
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C9, C9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C29A, C29
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C9, C10, C15, C14, C13, C12, C11, Cl1, Cl2} sigma for 1-2: 0.02, 1-3: 0.04
as
{C9A, C10A, C15A, C14A, C13A, C12A, C11A, Cl1A, Cl2A}
{C29, C30, C31, C32, C33, C34, C35, Cl21, Cl22} sigma for 1-2: 0.02, 1-3: 0.04
as
{C29A, C30A, C31A, C32A, C33A, C34A, C35A, Cl3, Cl4}
{C49, C50, C51, C52, C53, C54, C55, Cl41, Cl42} sigma for 1-2: 0.02, 1-3: 0.04
as
{C49A, C50A, C51A, C52A, C53A, C54A, C55A, Cl, Cl5}
6. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=
 Sof(H14A)=Sof(C13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=
 Sof(C13)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(Cl1)=Sof(Cl2)=FVAR(1)
 Sof(C29A)=Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(C31A)=Sof(C32A)=Sof(H32A)=
 Sof(C33A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=Sof(H35A)=Sof(Cl3)=Sof(Cl4)=1-FVAR(2)
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=
 Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(Cl21)=Sof(Cl22)=FVAR(2)
 Sof(C49A)=Sof(H49C)=Sof(H49D)=Sof(C50A)=Sof(C51A)=Sof(C52A)=Sof(H52A)=
 Sof(C53A)=Sof(C54A)=Sof(H54A)=Sof(C55A)=Sof(H55A)=Sof(Cl)=Sof(Cl5)=1-FVAR(3)
 Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(C51)=Sof(C52)=Sof(H52)=Sof(C53)=
 Sof(C54)=Sof(H54)=Sof(C55)=Sof(H55)=Sof(Cl41)=Sof(Cl42)=FVAR(3)
 Sof(C70A)=Sof(C71A)=Sof(C72A)=Sof(H72A)=Sof(C73A)=Sof(C74A)=Sof(H74A)=
 Sof(C75A)=Sof(H75A)=Sof(C69A)=Sof(H69C)=Sof(H69D)=Sof(Cl6)=Sof(Cl7)=1-FVAR(4)
 Sof(Cl61)=Sof(Cl62)=Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(C70)=Sof(C71)=Sof(C72)=
 Sof(H72)=Sof(C73)=Sof(C74)=Sof(H74)=Sof(C75)=Sof(H75)=FVAR(4)
7.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C49(H49A,H49B), C29(H29A,H29B), C69(H69A,H69B),
 C29A(H29C,H29D), C49A(H49C,H49D), C69A(H69C,H69D)
7.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C4(H4), C5(H5), C6(H6), C7(H7), C15A(H15A),
 C14A(H14A), C12A(H12A), C52(H52), C54(H54), C55(H55), C44(H44), C45(H45),
 C46(H46), C47(H47), C32(H32), C34(H34), C35(H35), C24(H24), C25(H25), C26(H26),
  C27(H27), C64(H64), C65(H65), C66(H66), C67(H67), C72(H72), C74(H74),
 C75(H75), C91(H91), C92(H92), C94(H94), C95(H95), C97(H97), C98(H98), C99(H99),
  C100(H100), C81(H81), C82(H82), C84(H84), C85(H85), C87(H87), C88(H88),
 C89(H89), C90(H90), C32A(H32A), C34A(H34A), C35A(H35A), C52A(H52A), C54A(H54A),
  C55A(H55A), C72A(H72A), C74A(H74A), C75A(H75A)
7.c Fitted hexagon refined as free rotating group:
 C10A(C15A,C14A,C13A,C12A,C11A), C30A(C31A,C32A,C33A,C34A,C35A), C50A(C51A,
 C52A,C53A,C54A,C55A), C70A(C71A,C72A,C73A,C74A,C75A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.6577(2) 0.2789(3) 0.6216(7) 0.0218(15) Uani 0.874(2) 1 d D U P A 1
H9A H 0.6659 0.2925 0.5219 0.026 Uiso 0.874(2) 1 calc R . P A 1
H9B H 0.6367 0.2523 0.5986 0.026 Uiso 0.874(2) 1 calc R . P A 1
C10 C 0.69502(12) 0.25425(17) 0.7060(4) 0.0194(9) Uani 0.874(2) 1 d D . P A 1
C15 C 0.69532(12) 0.20194(17) 0.7243(5) 0.0264(10) Uani 0.874(2) 1 d D . P A 1
H15 H 0.6717 0.1830 0.6897 0.032 Uiso 0.874(2) 1 calc R . P A 1
C14 C 0.72903(12) 0.17629(17) 0.7917(5) 0.0317(10) Uani 0.874(2) 1 d D . P A 1
H14 H 0.7288 0.1403 0.8024 0.038 Uiso 0.874(2) 1 calc R . P A 1
C13 C 0.76319(12) 0.20454(18) 0.8431(5) 0.0338(11) Uani 0.874(2) 1 d D . P A 1
C12 C 0.76380(12) 0.25633(18) 0.8292(5) 0.0363(11) Uani 0.874(2) 1 d D . P A 1
H12 H 0.7871 0.2753 0.8670 0.044 Uiso 0.874(2) 1 calc R . P A 1
C11 C 0.72988(11) 0.28093(17) 0.7593(5) 0.0286(10) Uani 0.874(2) 1 d D . P A 1
Cl1 Cl 0.73200(3) 0.34738(4) 0.73958(13) 0.0406(3) Uani 0.874(2) 1 d D . P A 1
Cl2 Cl 0.80616(3) 0.17329(6) 0.92704(19) 0.0579(5) Uani 0.874(2) 1 d D . P A 1
O1 O 0.59137(7) 0.32084(10) 1.1226(3) 0.0283(6) Uani 1 1 d . . . . .
H1 H 0.5814(11) 0.3290(15) 1.206(4) 0.042 Uiso 1 1 d R . . . .
O2 O 0.58143(7) 0.40458(10) 1.0858(2) 0.0278(6) Uani 1 1 d . . . . .
N1 N 0.63928(7) 0.32003(11) 0.7062(3) 0.0203(6) Uani 1 1 d D . . . .
N2 N 0.62587(7) 0.31204(11) 0.8487(3) 0.0202(6) Uani 1 1 d . . . . .
C1 C 0.59303(9) 0.36304(14) 1.0433(3) 0.0219(8) Uani 1 1 d . . . . .
C2 C 0.61061(9) 0.35674(14) 0.8913(3) 0.0210(8) Uani 1 1 d . . . . .
C3 C 0.61368(9) 0.39433(14) 0.7752(3) 0.0224(8) Uani 1 1 d . . . . .
C4 C 0.60297(10) 0.44592(14) 0.7567(4) 0.0275(8) Uani 1 1 d . . . . .
H4 H 0.5904 0.4640 0.8358 0.033 Uiso 1 1 calc R . . . .
C5 C 0.61121(11) 0.46955(15) 0.6203(4) 0.0327(9) Uani 1 1 d . . . . .
H5 H 0.6046 0.5046 0.6061 0.039 Uiso 1 1 calc R . . . .
C6 C 0.62921(11) 0.44282(15) 0.5019(4) 0.0321(9) Uani 1 1 d . . . . .
H6 H 0.6338 0.4602 0.4086 0.038 Uiso 1 1 calc R . . . .
C7 C 0.64024(10) 0.39294(15) 0.5163(4) 0.0278(8) Uani 1 1 d . . . . .
H7 H 0.6528 0.3752 0.4365 0.033 Uiso 1 1 calc R . . . .
C8 C 0.63204(9) 0.36893(13) 0.6569(3) 0.0210(8) Uani 1 1 d . . . . .
C9A C 0.6628(15) 0.277(2) 0.643(5) 0.039(16) Uiso 0.126(2) 1 d D U P A 2
H9AA H 0.6731 0.2880 0.5442 0.047 Uiso 0.126(2) 1 calc R . P A 2
H9AB H 0.6435 0.2484 0.6205 0.047 Uiso 0.126(2) 1 calc R . P A 2
C10A C 0.6984(7) 0.2567(9) 0.743(3) 0.045(5) Uiso 0.126(2) 1 d D . P A 2
C15A C 0.7238(7) 0.2925(7) 0.820(3) 0.045(5) Uiso 0.126(2) 1 d DG . P A 2
H15A H 0.7176 0.3277 0.8102 0.054 Uiso 0.126(2) 1 calc R . P A 2
C14A C 0.7581(6) 0.2765(7) 0.910(2) 0.045(5) Uiso 0.126(2) 1 d DG . P A 2
H14A H 0.7754 0.3009 0.9624 0.054 Uiso 0.126(2) 1 calc R . P A 2
C13A C 0.7672(5) 0.2249(8) 0.924(2) 0.045(5) Uiso 0.126(2) 1 d DG . P A 2
C12A C 0.7418(7) 0.1892(6) 0.847(3) 0.045(5) Uiso 0.126(2) 1 d DG . P A 2
H12A H 0.7480 0.1539 0.8564 0.054 Uiso 0.126(2) 1 calc R . P A 2
C11A C 0.7075(8) 0.2051(8) 0.757(3) 0.045(5) Uiso 0.126(2) 1 d DG . P A 2
Cl1A Cl 0.6848(4) 0.1584(5) 0.6377(13) 0.090(4) Uani 0.126(2) 1 d D . P A 2
Cl2A Cl 0.8099(2) 0.2017(3) 1.0330(9) 0.042(2) Uani 0.126(2) 1 d D . P A 2
C49 C 0.84486(12) 0.48044(15) 0.8177(4) 0.0240(10) Uani 0.9397(12) 1 d D U P B
1
H49A H 0.8647 0.5090 0.8182 0.029 Uiso 0.9397(12) 1 calc R . P B 1
H49B H 0.8390 0.4734 0.9260 0.029 Uiso 0.9397(12) 1 calc R . P B 1
C50 C 0.80528(11) 0.49635(15) 0.7273(4) 0.0221(9) Uani 0.9397(12) 1 d D . P B 1
C51 C 0.79158(10) 0.54634(15) 0.7289(4) 0.0247(9) Uani 0.9397(12) 1 d D . P B 1
C52 C 0.75648(10) 0.56243(15) 0.6442(4) 0.0264(9) Uani 0.9397(12) 1 d D . P B 1
H52 H 0.7481 0.5971 0.6464 0.032 Uiso 0.9397(12) 1 calc R . P B 1
C53 C 0.73409(10) 0.52739(16) 0.5573(4) 0.0263(9) Uani 0.9397(12) 1 d D . P B 1
C54 C 0.74569(10) 0.47703(16) 0.5530(4) 0.0303(9) Uani 0.9397(12) 1 d D . P B 1
H54 H 0.7295 0.4530 0.4940 0.036 Uiso 0.9397(12) 1 calc R . P B 1
C55 C 0.78174(10) 0.46186(15) 0.6371(4) 0.0268(9) Uani 0.9397(12) 1 d D . P B 1
H55 H 0.7903 0.4273 0.6325 0.032 Uiso 0.9397(12) 1 calc R . P B 1
Cl41 Cl 0.81808(3) 0.59220(4) 0.84064(11) 0.0385(3) Uani 0.9397(12) 1 d D . P B
1
Cl42 Cl 0.69022(3) 0.54808(4) 0.45037(10) 0.0362(3) Uani 0.9397(12) 1 d D . P B
1
O41 O 0.91134(7) 0.42512(10) 0.3403(3) 0.0341(6) Uani 1 1 d D . . . .
H41 H 0.9234(10) 0.4212(15) 0.239(3) 0.051 Uiso 1 1 d DR . . . .
O42 O 0.92023(7) 0.34189(10) 0.3894(2) 0.0297(6) Uani 1 1 d . . . . .
N41 N 0.86317(8) 0.43552(11) 0.7528(3) 0.0222(6) Uani 1 1 d D . . . .
N42 N 0.87857(8) 0.43988(11) 0.6122(3) 0.0245(7) Uani 1 1 d . . . . .
C41 C 0.90917(10) 0.38457(15) 0.4259(4) 0.0249(8) Uani 1 1 d . . . . .
C42 C 0.89190(9) 0.39375(14) 0.5760(3) 0.0233(8) Uani 1 1 d . . . . .
C43 C 0.88536(9) 0.35783(13) 0.6964(3) 0.0212(8) Uani 1 1 d . . . . .
C44 C 0.89328(10) 0.30581(14) 0.7227(4) 0.0259(8) Uani 1 1 d . . . . .
H44 H 0.9058 0.2857 0.6480 0.031 Uiso 1 1 calc R . . . .
C45 C 0.88250(10) 0.28474(15) 0.8587(4) 0.0291(8) Uani 1 1 d . . . . .
H45 H 0.8874 0.2496 0.8782 0.035 Uiso 1 1 calc R . . . .
C46 C 0.86424(10) 0.31478(15) 0.9700(4) 0.0300(9) Uani 1 1 d . . . . .
H46 H 0.8576 0.2993 1.0640 0.036 Uiso 1 1 calc R . . . .
C47 C 0.85582(10) 0.36529(15) 0.9477(4) 0.0273(8) Uani 1 1 d . . . . .
H47 H 0.8432 0.3850 1.0230 0.033 Uiso 1 1 calc R . . . .
C48 C 0.86679(9) 0.38673(14) 0.8079(3) 0.0215(8) Uani 1 1 d . . . . .
C29 C 0.35008(13) 0.26804(18) 2.7913(5) 0.0275(13) Uani 0.9311(15) 1 d D U P C
1
H29A H 0.3443 0.2743 2.9001 0.033 Uiso 0.9311(15) 1 calc R . P C 1
H29B H 0.3684 0.2380 2.7891 0.033 Uiso 0.9311(15) 1 calc R . P C 1
C30 C 0.30987(11) 0.25606(16) 2.6984(5) 0.0214(10) Uani 0.9311(15) 1 d D . P C
1
C31 C 0.29474(12) 0.20666(17) 2.6837(5) 0.0260(10) Uani 0.9311(15) 1 d D . P C
1
C32 C 0.25921(12) 0.19530(17) 2.5947(5) 0.0290(10) Uani 0.9311(15) 1 d D . P C
1
H32 H 0.2497 0.1611 2.5847 0.035 Uiso 0.9311(15) 1 calc R . P C 1
C33 C 0.23783(11) 0.23445(17) 2.5208(4) 0.0263(11) Uani 0.9311(15) 1 d D . P C
1
C34 C 0.25101(10) 0.28377(16) 2.5366(4) 0.0274(9) Uani 0.9311(15) 1 d D . P C 1
H34 H 0.2355 0.3106 2.4881 0.033 Uiso 0.9311(15) 1 calc R . P C 1
C35 C 0.28718(10) 0.29440(15) 2.6237(4) 0.0237(9) Uani 0.9311(15) 1 d D . P C 1
H35 H 0.2965 0.3286 2.6323 0.028 Uiso 0.9311(15) 1 calc R . P C 1
Cl21 Cl 0.32064(3) 0.15665(4) 2.78039(10) 0.0298(3) Uani 0.9311(15) 1 d D . P C
1
Cl22 Cl 0.19352(3) 0.22059(5) 2.40698(13) 0.0404(3) Uani 0.9311(15) 1 d D . P C
1
O21 O 0.42647(7) 0.32188(9) 2.3342(3) 0.0288(6) Uani 1 1 d . . . . .
H21 H 0.4340(10) 0.3290(14) 2.234(4) 0.043 Uiso 1 1 d R . . . .
O22 O 0.43084(7) 0.40592(10) 2.3785(2) 0.0272(6) Uani 1 1 d . . . . .
N21 N 0.37102(7) 0.31200(11) 2.7329(3) 0.0217(7) Uani 1 1 d . . . . .
N22 N 0.38796(7) 0.30752(11) 2.5953(3) 0.0210(6) Uani 1 1 d . . . . .
C21 C 0.42174(9) 0.36301(15) 2.4167(3) 0.0226(8) Uani 1 1 d . . . . .
C22 C 0.40305(9) 0.35335(13) 2.5641(3) 0.0187(7) Uani 1 1 d . . . . .
C23 C 0.39604(9) 0.38862(14) 2.6845(3) 0.0221(8) Uani 1 1 d . . . . .
C24 C 0.40526(11) 0.43987(14) 2.7156(4) 0.0307(9) Uani 1 1 d . . . . .
H24 H 0.4199 0.4598 2.6464 0.037 Uiso 1 1 calc R . . . .
C25 C 0.39221(12) 0.46052(16) 2.8508(4) 0.0414(10) Uani 1 1 d . . . . .
H25 H 0.3977 0.4953 2.8743 0.050 Uiso 1 1 calc R . . . .
C26 C 0.37099(12) 0.43062(17) 2.9539(4) 0.0406(10) Uani 1 1 d . . . . .
H26 H 0.3624 0.4460 3.0454 0.049 Uiso 1 1 calc R . . . .
C27 C 0.36220(11) 0.38051(16) 2.9276(4) 0.0350(10) Uani 1 1 d . . . . .
H27 H 0.3482 0.3606 2.9986 0.042 Uiso 1 1 calc DR . . . .
C28 C 0.37497(9) 0.36015(14) 2.7903(3) 0.0240(8) Uani 1 1 d . . . . .
Cl61 Cl 1.22403(3) 0.39419(4) -1.24682(11) 0.0343(3) Uani 0.9067(17) 1 d . . P
D 1
Cl62 Cl 1.30306(6) 0.55281(10) -0.9815(3) 0.0854(9) Uani 0.9067(17) 1 d . . P D
1
O61 O 1.07902(8) 0.43121(10) -0.8660(3) 0.0329(6) Uani 1 1 d . . . . .
H61 H 1.0688(12) 0.4249(16) -0.785(4) 0.049 Uiso 1 1 d R . . . .
O62 O 1.06963(7) 0.34711(10) -0.9012(3) 0.0318(6) Uani 1 1 d . . . . .
N61 N 1.13164(8) 0.43081(12) -1.2728(3) 0.0277(7) Uani 1 1 d D . . . .
N62 N 1.11672(8) 0.43924(12) -1.1330(3) 0.0249(7) Uani 1 1 d . . . . .
C61 C 1.08114(10) 0.38870(15) -0.9452(4) 0.0266(8) Uani 1 1 d . . . . .
C62 C 1.09952(10) 0.39508(14) -1.0946(4) 0.0257(8) Uani 1 1 d . . . . .
C63 C 1.10272(10) 0.35760(15) -1.2115(4) 0.0310(9) Uani 1 1 d . . . . .
C64 C 1.09062(12) 0.30679(15) -1.2348(4) 0.0370(9) Uani 1 1 d . . . . .
H64 H 1.0764 0.2889 -1.1597 0.044 Uiso 1 1 calc R . . . .
C65 C 1.09999(13) 0.28373(17) -1.3695(4) 0.0477(11) Uani 1 1 d . . . . .
H65 H 1.0925 0.2491 -1.3868 0.057 Uiso 1 1 calc R . . . .
C66 C 1.12034(14) 0.30993(19) -1.4824(4) 0.0537(13) Uani 1 1 d . . . . .
H66 H 1.1258 0.2925 -1.5746 0.064 Uiso 1 1 calc R . . . .
C67 C 1.13261(11) 0.35941(17) -1.4655(4) 0.0399(10) Uani 1 1 d . . . . .
H67 H 1.1463 0.3770 -1.5428 0.048 Uiso 1 1 calc R . . . .
C68 C 1.12362(10) 0.38265(16) -1.3257(4) 0.0320(9) Uani 1 1 d . . . . .
C69 C 1.1540(2) 0.4706(3) -1.3493(7) 0.0330(15) Uani 0.9067(17) 1 d D U P D 1
H69A H 1.1353 0.4997 -1.3731 0.040 Uiso 0.9067(17) 1 calc R . P D 1
H69B H 1.1629 0.4572 -1.4483 0.040 Uiso 0.9067(17) 1 calc R . P D 1
C70 C 1.19119(12) 0.48935(18) -1.2522(4) 0.0258(10) Uani 0.9067(17) 1 d D . P D
1
C71 C 1.22436(11) 0.45850(17) -1.2020(5) 0.0290(10) Uani 0.9067(17) 1 d . . P D
1
C72 C 1.25855(13) 0.47808(19) -1.1197(5) 0.0390(12) Uani 0.9067(17) 1 d . . P D
1
H72 H 1.2808 0.4564 -1.0874 0.047 Uiso 0.9067(17) 1 calc R . P D 1
C73 C 1.25993(13) 0.5292(2) -1.0854(6) 0.0472(14) Uani 0.9067(17) 1 d . . P D 1
C74 C 1.22745(15) 0.5609(2) -1.1335(7) 0.0464(14) Uani 0.9067(17) 1 d . . P D 1
H74 H 1.2284 0.5962 -1.1096 0.056 Uiso 0.9067(17) 1 calc R . P D 1
C75 C 1.19387(14) 0.54070(19) -1.2160(6) 0.0363(13) Uani 0.9067(17) 1 d . . P D
1
H75 H 1.1719 0.5626 -1.2491 0.044 Uiso 0.9067(17) 1 calc R . P D 1
N91 N 0.94520(8) 0.41539(12) 0.0867(3) 0.0263(7) Uani 1 1 d . . . . .
N92 N 1.04791(8) 0.42243(12) -0.6004(3) 0.0269(7) Uani 1 1 d . . . . .
C91 C 0.94689(9) 0.45850(14) 0.0028(3) 0.0262(8) Uani 1 1 d . . . . .
H91 H 0.9335 0.4883 0.0365 0.031 Uiso 1 1 calc R . . . .
C92 C 0.96748(9) 0.46052(14) -0.1306(3) 0.0249(8) Uani 1 1 d . . . . .
H92 H 0.9686 0.4915 -0.1867 0.030 Uiso 1 1 calc R . . . .
C93 C 0.98648(9) 0.41715(14) -0.1824(3) 0.0232(8) Uani 1 1 d . . . . .
C94 C 0.98369(10) 0.37219(15) -0.0970(4) 0.0284(8) Uani 1 1 d . . . . .
H94 H 0.9955 0.3414 -0.1306 0.034 Uiso 1 1 calc R . . . .
C95 C 0.96329(10) 0.37357(15) 0.0373(4) 0.0280(8) Uani 1 1 d . . . . .
H95 H 0.9621 0.3433 0.0970 0.034 Uiso 1 1 calc R . . . .
C96 C 1.00866(9) 0.41850(14) -0.3265(3) 0.0234(8) Uani 1 1 d . . . . .
C97 C 1.03021(9) 0.46175(13) -0.3670(3) 0.0223(8) Uani 1 1 d . . . . .
H97 H 1.0314 0.4908 -0.3016 0.027 Uiso 1 1 calc R . . . .
C98 C 1.04978(9) 0.46192(14) -0.5029(3) 0.0263(8) Uani 1 1 d . . . . .
H98 H 1.0651 0.4911 -0.5281 0.032 Uiso 1 1 calc R . . . .
C99 C 1.02750(10) 0.38065(14) -0.5618(4) 0.0290(8) Uani 1 1 d . . . . .
H99 H 1.0265 0.3524 -0.6306 0.035 Uiso 1 1 calc R . . . .
C100 C 1.00777(10) 0.37672(14) -0.4261(4) 0.0272(8) Uani 1 1 d . . . . .
H100 H 0.9939 0.3463 -0.4013 0.033 Uiso 1 1 calc R . . . .
N81 N 0.55685(7) 0.32965(11) 1.3779(3) 0.0224(7) Uani 1 1 d . . . . .
N82 N 0.45542(8) 0.33279(12) 2.0676(3) 0.0250(7) Uani 1 1 d . . . . .
C81 C 0.55593(9) 0.28834(14) 1.4689(3) 0.0213(8) Uani 1 1 d . . . . .
H81 H 0.5695 0.2583 1.4391 0.026 Uiso 1 1 calc R . . . .
C82 C 0.53613(9) 0.28783(13) 1.6032(3) 0.0202(8) Uani 1 1 d . . . . .
H82 H 0.5355 0.2577 1.6635 0.024 Uiso 1 1 calc R . . . .
C83 C 0.51706(9) 0.33192(13) 1.6499(3) 0.0200(8) Uani 1 1 d . . . . .
C84 C 0.51913(9) 0.37530(14) 1.5578(3) 0.0217(8) Uani 1 1 d . . . . .
H84 H 0.5071 0.4064 1.5876 0.026 Uiso 1 1 calc R . . . .
C85 C 0.53883(9) 0.37230(14) 1.4234(3) 0.0227(8) Uani 1 1 d . . . . .
H85 H 0.5397 0.4018 1.3602 0.027 Uiso 1 1 calc R . . . .
C86 C 0.49484(8) 0.33272(13) 1.7953(3) 0.0177(7) Uani 1 1 d . . . . .
C87 C 0.47361(9) 0.28997(14) 1.8413(3) 0.0221(8) Uani 1 1 d . . . . .
H87 H 0.4725 0.2600 1.7799 0.027 Uiso 1 1 calc R . . . .
C88 C 0.45437(9) 0.29182(14) 1.9765(3) 0.0220(8) Uani 1 1 d . . . . .
H88 H 0.4396 0.2627 2.0067 0.026 Uiso 1 1 calc R . . . .
C89 C 0.47520(10) 0.37401(14) 2.0241(3) 0.0248(8) Uani 1 1 d . . . . .
H89 H 0.4758 0.4032 2.0888 0.030 Uiso 1 1 calc R . . . .
C90 C 0.49500(9) 0.37607(14) 1.8879(3) 0.0246(8) Uani 1 1 d . . . . .
H90 H 0.5084 0.4063 1.8585 0.030 Uiso 1 1 calc R . . . .
C29A C 0.3485(17) 0.2717(12) 2.826(10) 0.028(8) Uiso 0.0689(15) 1 d D U P C 2
H29C H 0.3654 0.2407 2.8433 0.033 Uiso 0.0689(15) 1 calc DR . P C 2
H29D H 0.3415 0.2855 2.9272 0.033 Uiso 0.0689(15) 1 calc DR . P C 2
C30A C 0.3099(9) 0.2605(11) 2.723(7) 0.028(8) Uiso 0.0689(15) 1 d D . P C 2
C31A C 0.2784(9) 0.2946(8) 2.683(5) 0.028(8) Uiso 0.0689(15) 1 d DG . P C 2
C32A C 0.2426(8) 0.2775(9) 2.604(4) 0.028(8) Uiso 0.0689(15) 1 d DG . P C 2
H32A H 0.2210 0.3008 2.5771 0.033 Uiso 0.0689(15) 1 calc R . P C 2
C33A C 0.2384(8) 0.2264(10) 2.564(5) 0.028(8) Uiso 0.0689(15) 1 d DG . P C 2
C34A C 0.2699(10) 0.1923(9) 2.604(7) 0.028(8) Uiso 0.0689(15) 1 d DG . P C 2
H34A H 0.2670 0.1573 2.5768 0.033 Uiso 0.0689(15) 1 calc R . P C 2
C35A C 0.3057(10) 0.2094(10) 2.683(7) 0.028(8) Uiso 0.0689(15) 1 d DG . P C 2
H35A H 0.3273 0.1861 2.7103 0.033 Uiso 0.0689(15) 1 calc R . P C 2
Cl3 Cl 0.2800(4) 0.3596(5) 2.7331(13) 0.0298(3) Uani 0.0689(15) 1 d D . P C 2
Cl4 Cl 0.1928(4) 0.2022(7) 2.4793(19) 0.0404(3) Uani 0.0689(15) 1 d D . P C 2
C49A C 0.8446(15) 0.471(2) 0.854(4) 0.033(7) Uiso 0.0603(12) 1 d D U P B 2
H49C H 0.8647 0.4972 0.8911 0.039 Uiso 0.0603(12) 1 calc R . P B 2
H49D H 0.8345 0.4531 0.9439 0.039 Uiso 0.0603(12) 1 calc R . P B 2
C50A C 0.8088(8) 0.4959(10) 0.758(6) 0.033(7) Uiso 0.0603(12) 1 d D . P B 2
C51A C 0.7741(9) 0.4682(7) 0.708(5) 0.033(7) Uiso 0.0603(12) 1 d DG . P B 2
C52A C 0.7382(7) 0.4935(9) 0.659(4) 0.033(7) Uiso 0.0603(12) 1 d DG . P B 2
H52A H 0.7144 0.4746 0.6256 0.039 Uiso 0.0603(12) 1 calc R . P B 2
C53A C 0.7370(8) 0.5465(9) 0.660(5) 0.033(7) Uiso 0.0603(12) 1 d DG . P B 2
C54A C 0.7717(9) 0.5742(7) 0.709(5) 0.033(7) Uiso 0.0603(12) 1 d DG . P B 2
H54A H 0.7708 0.6103 0.7098 0.039 Uiso 0.0603(12) 1 calc R . P B 2
C55A C 0.8076(8) 0.5489(10) 0.758(6) 0.033(7) Uiso 0.0603(12) 1 d DG . P B 2
H55A H 0.8313 0.5678 0.7922 0.039 Uiso 0.0603(12) 1 calc R . P B 2
Cl Cl 0.7719(4) 0.4026(6) 0.7327(16) 0.0362(3) Uani 0.0603(12) 1 d D . P B 2
Cl5 Cl 0.6941(4) 0.5815(6) 0.6005(17) 0.0385(3) Uani 0.0603(12) 1 d D . P B 2
C70A C 1.1919(8) 0.4940(15) -1.205(4) 0.021(5) Uiso 0.0933(17) 1 d D . P D 2
C71A C 1.2040(12) 0.5444(13) -1.183(4) 0.021(5) Uiso 0.0933(17) 1 d G . P D 2
C72A C 1.2408(13) 0.5555(10) -1.099(4) 0.021(5) Uiso 0.0933(17) 1 d G . P D 2
H72A H 1.2490 0.5899 -1.0840 0.025 Uiso 0.0933(17) 1 calc R . P D 2
C73A C 1.2654(9) 0.5162(13) -1.038(3) 0.021(5) Uiso 0.0933(17) 1 d G . P D 2
C74A C 1.2533(8) 0.4658(11) -1.061(3) 0.021(5) Uiso 0.0933(17) 1 d G . P D 2
H74A H 1.2701 0.4390 -1.0192 0.025 Uiso 0.0933(17) 1 calc R . P D 2
C75A C 1.2165(9) 0.4547(11) -1.144(3) 0.021(5) Uiso 0.0933(17) 1 d G . P D 2
H75A H 1.2083 0.4203 -1.1598 0.025 Uiso 0.0933(17) 1 calc R . P D 2
C69A C 1.157(2) 0.475(2) -1.315(6) 0.021(14) Uiso 0.0933(17) 1 d D U P D 2
H69C H 1.1378 0.5036 -1.3360 0.026 Uiso 0.0933(17) 1 calc R . P D 2
H69D H 1.1686 0.4660 -1.4136 0.026 Uiso 0.0933(17) 1 calc R . P D 2
Cl6 Cl 1.1821(3) 0.5933(4) -1.2893(11) 0.0343(3) Uani 0.0933(17) 1 d . . P D 2
Cl7 Cl 1.3100(6) 0.5285(11) -0.913(2) 0.090(10) Uani 0.0933(17) 1 d . . P D 2


_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
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(6) . ?
C9 N1 1.458(5) . ?
C10 C15 1.382(5) . ?
C10 C11 1.389(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.386(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.388(6) . ?
C13 C12 1.365(6) . ?
C13 Cl2 1.742(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.386(5) . ?
C11 Cl1 1.754(4) . ?
O1 H1 0.84(4) . ?
O1 C1 1.307(4) . ?
O2 C1 1.219(4) . ?
N1 N2 1.357(3) . ?
N1 C8 1.368(4) . ?
N1 C9A 1.491(16) . ?
N2 C2 1.336(4) . ?
C1 C2 1.484(4) . ?
C2 C3 1.419(4) . ?
C3 C4 1.404(5) . ?
C3 C8 1.394(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.406(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.361(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.415(4) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.499(15) . ?
C10A C15A 1.3900 . ?
C10A C11A 1.3900 . ?
C15A H15A 0.9500 . ?
C15A C14A 1.3900 . ?
C14A H14A 0.9500 . ?
C14A C13A 1.3900 . ?
C13A C12A 1.3900 . ?
C13A Cl2A 1.745(13) . ?
C12A H12A 0.9500 . ?
C12A C11A 1.3900 . ?
C11A Cl1A 1.736(14) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 C50 1.525(4) . ?
C49 N41 1.453(4) . ?
C50 C51 1.386(5) . ?
C50 C55 1.394(5) . ?
C51 C52 1.386(4) . ?
C51 Cl41 1.740(4) . ?
C52 H52 0.9500 . ?
C52 C53 1.369(5) . ?
C53 C54 1.376(5) . ?
C53 Cl42 1.741(3) . ?
C54 H54 0.9500 . ?
C54 C55 1.401(5) . ?
C55 H55 0.9500 . ?
O41 H41 0.996(18) . ?
O41 C41 1.302(4) . ?
O42 C41 1.225(4) . ?
N41 N42 1.357(3) . ?
N41 C48 1.369(4) . ?
N41 C49A 1.44(2) . ?
N42 C42 1.331(4) . ?
C41 C42 1.475(4) . ?
C42 C43 1.434(5) . ?
C43 C44 1.405(5) . ?
C43 C48 1.400(4) . ?
C44 H44 0.9500 . ?
C44 C45 1.372(5) . ?
C45 H45 0.9500 . ?
C45 C46 1.410(5) . ?
C46 H46 0.9500 . ?
C46 C47 1.365(5) . ?
C47 H47 0.9500 . ?
C47 C48 1.406(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.527(5) . ?
C29 N21 1.450(6) . ?
C30 C31 1.390(5) . ?
C30 C35 1.384(5) . ?
C31 C32 1.383(5) . ?
C31 Cl21 1.746(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.376(5) . ?
C33 C34 1.368(5) . ?
C33 Cl22 1.736(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.388(4) . ?
C35 H35 0.9500 . ?
O21 H21 0.94(4) . ?
O21 C21 1.310(4) . ?
O22 C21 1.216(4) . ?
N21 N22 1.356(3) . ?
N21 C28 1.361(4) . ?
N21 C29A 1.55(9) . ?
N22 C22 1.334(4) . ?
C21 C22 1.477(4) . ?
C22 C23 1.426(4) . ?
C23 C24 1.400(5) . ?
C23 C28 1.401(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.407(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.362(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.395(4) . ?
Cl61 C71 1.732(4) . ?
Cl62 C73 1.735(5) . ?
O61 H61 0.82(4) . ?
O61 C61 1.315(4) . ?
O62 C61 1.224(4) . ?
N61 N62 1.357(3) . ?
N61 C68 1.364(5) . ?
N61 C69 1.460(5) . ?
N61 C69A 1.472(19) . ?
N62 C62 1.340(4) . ?
C61 C62 1.475(5) . ?
C62 C63 1.422(5) . ?
C63 C64 1.401(5) . ?
C63 C68 1.405(5) . ?
C64 H64 0.9500 . ?
C64 C65 1.369(5) . ?
C65 H65 0.9500 . ?
C65 C66 1.402(6) . ?
C66 H66 0.9500 . ?
C66 C67 1.364(6) . ?
C67 H67 0.9500 . ?
C67 C68 1.407(5) . ?
C69 H69A 0.9900 . ?
C69 H69B 0.9900 . ?
C69 C70 1.514(6) . ?
C70 C71 1.398(5) . ?
C70 C75 1.385(6) . ?
C71 C72 1.384(5) . ?
C72 H72 0.9500 . ?
C72 C73 1.374(6) . ?
C73 C74 1.390(6) . ?
C74 H74 0.9500 . ?
C74 C75 1.375(6) . ?
C75 H75 0.9500 . ?
N91 C91 1.349(4) . ?
N91 C95 1.331(4) . ?
N92 C98 1.337(4) . ?
N92 C99 1.337(4) . ?
C91 H91 0.9500 . ?
C91 C92 1.379(4) . ?
C92 H92 0.9500 . ?
C92 C93 1.386(5) . ?
C93 C94 1.400(5) . ?
C93 C96 1.488(4) . ?
C94 H94 0.9500 . ?
C94 C95 1.382(4) . ?
C95 H95 0.9500 . ?
C96 C97 1.393(5) . ?
C96 C100 1.395(5) . ?
C97 H97 0.9500 . ?
C97 C98 1.380(4) . ?
C98 H98 0.9500 . ?
C99 H99 0.9500 . ?
C99 C100 1.385(4) . ?
C100 H100 0.9500 . ?
N81 C81 1.343(4) . ?
N81 C85 1.337(4) . ?
N82 C88 1.334(4) . ?
N82 C89 1.328(4) . ?
C81 H81 0.9500 . ?
C81 C82 1.371(4) . ?
C82 H82 0.9500 . ?
C82 C83 1.387(5) . ?
C83 C84 1.396(4) . ?
C83 C86 1.499(4) . ?
C84 H84 0.9500 . ?
C84 C85 1.372(4) . ?
C85 H85 0.9500 . ?
C86 C87 1.392(5) . ?
C86 C90 1.393(4) . ?
C87 H87 0.9500 . ?
C87 C88 1.369(4) . ?
C88 H88 0.9500 . ?
C89 H89 0.9500 . ?
C89 C90 1.387(4) . ?
C90 H90 0.9500 . ?
C29A H29C 0.9900 . ?
C29A H29D 0.9900 . ?
C29A C30A 1.523(17) . ?
C30A C31A 1.3900 . ?
C30A C35A 1.3900 . ?
C31A C32A 1.3900 . ?
C31A Cl3 1.761(16) . ?
C32A H32A 0.9500 . ?
C32A C33A 1.3900 . ?
C33A C34A 1.3900 . ?
C33A Cl4 1.737(15) . ?
C34A H34A 0.9500 . ?
C34A C35A 1.3900 . ?
C35A H35A 0.9500 . ?
C49A H49C 0.9900 . ?
C49A H49D 0.9900 . ?
C49A C50A 1.533(18) . ?
C50A C51A 1.3900 . ?
C50A C55A 1.3900 . ?
C51A C52A 1.3900 . ?
C51A Cl 1.738(16) . ?
C52A H52A 0.9500 . ?
C52A C53A 1.3900 . ?
C53A C54A 1.3900 . ?
C53A Cl5 1.724(15) . ?
C54A H54A 0.9500 . ?
C54A C55A 1.3900 . ?
C55A H55A 0.9500 . ?
C70A C71A 1.3900 . ?
C70A C75A 1.3900 . ?
C70A C69A 1.527(19) . ?
C71A C72A 1.3900 . ?
C71A Cl6 1.71(3) . ?
C72A H72A 0.9500 . ?
C72A C73A 1.3900 . ?
C73A C74A 1.3900 . ?
C73A Cl7 1.79(3) . ?
C74A H74A 0.9500 . ?
C74A C75A 1.3900 . ?
C75A H75A 0.9500 . ?
C69A H69C 0.9900 . ?
C69A H69D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
N1 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
N1 C9 C10 114.6(4) . . ?
C15 C10 C9 118.5(4) . . ?
C15 C10 C11 117.6(3) . . ?
C11 C10 C9 123.9(4) . . ?
C10 C15 H15 119.0 . . ?
C10 C15 C14 122.0(4) . . ?
C14 C15 H15 119.0 . . ?
C15 C14 H14 120.8 . . ?
C15 C14 C13 118.4(4) . . ?
C13 C14 H14 120.8 . . ?
C14 C13 Cl2 119.4(3) . . ?
C12 C13 C14 121.3(4) . . ?
C12 C13 Cl2 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C13 C12 C11 119.1(4) . . ?
C11 C12 H12 120.4 . . ?
C10 C11 Cl1 120.4(3) . . ?
C12 C11 C10 121.6(4) . . ?
C12 C11 Cl1 118.0(3) . . ?
C1 O1 H1 106(3) . . ?
N2 N1 C9 121.0(4) . . ?
N2 N1 C8 111.7(3) . . ?
N2 N1 C9A 115(3) . . ?
C8 N1 C9 127.2(4) . . ?
C8 N1 C9A 133(3) . . ?
C2 N2 N1 105.4(3) . . ?
O1 C1 C2 114.0(3) . . ?
O2 C1 O1 125.0(3) . . ?
O2 C1 C2 121.0(3) . . ?
N2 C2 C1 121.2(3) . . ?
N2 C2 C3 111.6(3) . . ?
C3 C2 C1 127.2(3) . . ?
C4 C3 C2 136.2(3) . . ?
C8 C3 C2 104.2(3) . . ?
C8 C3 C4 119.6(3) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.3(4) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.3(3) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 121.8 . . ?
C6 C7 C8 116.3(3) . . ?
C8 C7 H7 121.8 . . ?
N1 C8 C3 107.0(3) . . ?
N1 C8 C7 130.4(3) . . ?
C3 C8 C7 122.6(3) . . ?
N1 C9A H9AA 108.0 . . ?
N1 C9A H9AB 108.0 . . ?
N1 C9A C10A 117.2(19) . . ?
H9AA C9A H9AB 107.2 . . ?
C10A C9A H9AA 108.0 . . ?
C10A C9A H9AB 108.0 . . ?
C15A C10A C9A 117(2) . . ?
C15A C10A C11A 120.0 . . ?
C11A C10A C9A 123.1(19) . . ?
C10A C15A H15A 120.0 . . ?
C14A C15A C10A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C15A C14A C13A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C14A C13A Cl2A 123.0(11) . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A Cl2A 117.0(11) . . ?
C13A C12A H12A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C10A C11A Cl1A 123.9(12) . . ?
C12A C11A C10A 120.0 . . ?
C12A C11A Cl1A 114.8(12) . . ?
H49A C49 H49B 107.9 . . ?
C50 C49 H49A 109.1 . . ?
C50 C49 H49B 109.1 . . ?
N41 C49 H49A 109.1 . . ?
N41 C49 H49B 109.1 . . ?
N41 C49 C50 112.3(3) . . ?
C51 C50 C49 121.1(3) . . ?
C51 C50 C55 117.0(3) . . ?
C55 C50 C49 121.9(3) . . ?
C50 C51 Cl41 120.7(3) . . ?
C52 C51 C50 122.6(3) . . ?
C52 C51 Cl41 116.6(3) . . ?
C51 C52 H52 120.7 . . ?
C53 C52 C51 118.7(4) . . ?
C53 C52 H52 120.7 . . ?
C52 C53 C54 121.5(3) . . ?
C52 C53 Cl42 118.3(3) . . ?
C54 C53 Cl42 120.2(3) . . ?
C53 C54 H54 120.6 . . ?
C53 C54 C55 118.8(3) . . ?
C55 C54 H54 120.6 . . ?
C50 C55 C54 121.4(4) . . ?
C50 C55 H55 119.3 . . ?
C54 C55 H55 119.3 . . ?
C41 O41 H41 118(2) . . ?
N42 N41 C49 117.9(3) . . ?
N42 N41 C48 111.4(3) . . ?
N42 N41 C49A 134(3) . . ?
C48 N41 C49 130.6(3) . . ?
C48 N41 C49A 115(3) . . ?
C42 N42 N41 106.4(3) . . ?
O41 C41 C42 114.2(3) . . ?
O42 C41 O41 124.8(3) . . ?
O42 C41 C42 121.0(3) . . ?
N42 C42 C41 120.5(3) . . ?
N42 C42 C43 111.0(3) . . ?
C43 C42 C41 128.5(3) . . ?
C44 C43 C42 136.2(3) . . ?
C48 C43 C42 104.0(3) . . ?
C48 C43 C44 119.8(3) . . ?
C43 C44 H44 120.8 . . ?
C45 C44 C43 118.4(3) . . ?
C45 C44 H44 120.8 . . ?
C44 C45 H45 119.7 . . ?
C44 C45 C46 120.7(3) . . ?
C46 C45 H45 119.7 . . ?
C45 C46 H46 118.8 . . ?
C47 C46 C45 122.4(3) . . ?
C47 C46 H46 118.8 . . ?
C46 C47 H47 121.6 . . ?
C46 C47 C48 116.8(3) . . ?
C48 C47 H47 121.6 . . ?
N41 C48 C43 107.2(3) . . ?
N41 C48 C47 130.9(3) . . ?
C43 C48 C47 121.9(3) . . ?
H29A C29 H29B 107.8 . . ?
C30 C29 H29A 109.0 . . ?
C30 C29 H29B 109.0 . . ?
N21 C29 H29A 109.0 . . ?
N21 C29 H29B 109.0 . . ?
N21 C29 C30 112.9(3) . . ?
C31 C30 C29 121.9(4) . . ?
C35 C30 C29 120.8(4) . . ?
C35 C30 C31 117.3(3) . . ?
C30 C31 Cl21 119.9(3) . . ?
C32 C31 C30 122.2(3) . . ?
C32 C31 Cl21 117.9(3) . . ?
C31 C32 H32 120.7 . . ?
C33 C32 C31 118.7(4) . . ?
C33 C32 H32 120.7 . . ?
C32 C33 Cl22 119.1(3) . . ?
C34 C33 C32 120.9(3) . . ?
C34 C33 Cl22 120.0(3) . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.7(4) . . ?
C35 C34 H34 120.2 . . ?
C30 C35 C34 121.2(4) . . ?
C30 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C21 O21 H21 113(2) . . ?
N22 N21 C29 118.0(3) . . ?
N22 N21 C28 111.7(3) . . ?
N22 N21 C29A 130(2) . . ?
C28 N21 C29 130.2(3) . . ?
C28 N21 C29A 119(2) . . ?
C22 N22 N21 106.2(3) . . ?
O21 C21 C22 113.8(3) . . ?
O22 C21 O21 125.0(3) . . ?
O22 C21 C22 121.2(3) . . ?
N22 C22 C21 120.7(3) . . ?
N22 C22 C23 110.9(3) . . ?
C23 C22 C21 128.3(3) . . ?
C24 C23 C22 136.2(3) . . ?
C24 C23 C28 119.6(3) . . ?
C28 C23 C22 104.2(3) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 C23 117.7(3) . . ?
C25 C24 H24 121.2 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 120.9(4) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 118.7 . . ?
C27 C26 C25 122.6(3) . . ?
C27 C26 H26 118.7 . . ?
C26 C27 H27 121.9 . . ?
C26 C27 C28 116.2(4) . . ?
C28 C27 H27 121.9 . . ?
N21 C28 C23 107.1(3) . . ?
N21 C28 C27 129.9(3) . . ?
C27 C28 C23 123.0(4) . . ?
C61 O61 H61 109(3) . . ?
N62 N61 C68 112.3(3) . . ?
N62 N61 C69 120.8(4) . . ?
N62 N61 C69A 110(3) . . ?
C68 N61 C69 126.9(4) . . ?
C68 N61 C69A 137(3) . . ?
C62 N62 N61 105.3(3) . . ?
O61 C61 C62 113.7(3) . . ?
O62 C61 O61 124.4(3) . . ?
O62 C61 C62 121.8(3) . . ?
N62 C62 C61 121.3(3) . . ?
N62 C62 C63 111.6(3) . . ?
C63 C62 C61 127.1(3) . . ?
C64 C63 C62 136.6(4) . . ?
C64 C63 C68 119.3(3) . . ?
C68 C63 C62 104.1(3) . . ?
C63 C64 H64 121.1 . . ?
C65 C64 C63 117.8(4) . . ?
C65 C64 H64 121.1 . . ?
C64 C65 H65 119.2 . . ?
C64 C65 C66 121.6(4) . . ?
C66 C65 H65 119.2 . . ?
C65 C66 H66 118.6 . . ?
C67 C66 C65 122.8(4) . . ?
C67 C66 H66 118.6 . . ?
C66 C67 H67 122.3 . . ?
C66 C67 C68 115.4(4) . . ?
C68 C67 H67 122.3 . . ?
N61 C68 C63 106.7(3) . . ?
N61 C68 C67 130.2(4) . . ?
C63 C68 C67 123.1(4) . . ?
N61 C69 H69A 109.0 . . ?
N61 C69 H69B 109.0 . . ?
N61 C69 C70 112.7(4) . . ?
H69A C69 H69B 107.8 . . ?
C70 C69 H69A 109.0 . . ?
C70 C69 H69B 109.0 . . ?
C71 C70 C69 124.2(5) . . ?
C75 C70 C69 118.6(4) . . ?
C75 C70 C71 117.2(4) . . ?
C70 C71 Cl61 120.1(3) . . ?
C72 C71 Cl61 118.1(3) . . ?
C72 C71 C70 121.8(4) . . ?
C71 C72 H72 120.4 . . ?
C73 C72 C71 119.2(4) . . ?
C73 C72 H72 120.4 . . ?
C72 C73 Cl62 118.4(4) . . ?
C72 C73 C74 120.4(4) . . ?
C74 C73 Cl62 121.3(4) . . ?
C73 C74 H74 120.3 . . ?
C75 C74 C73 119.5(4) . . ?
C75 C74 H74 120.3 . . ?
C70 C75 H75 119.0 . . ?
C74 C75 C70 121.9(4) . . ?
C74 C75 H75 119.0 . . ?
C95 N91 C91 118.8(3) . . ?
C98 N92 C99 118.6(3) . . ?
N91 C91 H91 119.1 . . ?
N91 C91 C92 121.7(3) . . ?
C92 C91 H91 119.1 . . ?
C91 C92 H92 120.1 . . ?
C91 C92 C93 119.7(3) . . ?
C93 C92 H92 120.1 . . ?
C92 C93 C94 118.3(3) . . ?
C92 C93 C96 120.5(3) . . ?
C94 C93 C96 121.2(3) . . ?
C93 C94 H94 120.7 . . ?
C95 C94 C93 118.5(3) . . ?
C95 C94 H94 120.7 . . ?
N91 C95 C94 122.9(3) . . ?
N91 C95 H95 118.5 . . ?
C94 C95 H95 118.5 . . ?
C97 C96 C93 121.0(3) . . ?
C97 C96 C100 118.3(3) . . ?
C100 C96 C93 120.8(3) . . ?
C96 C97 H97 120.3 . . ?
C98 C97 C96 119.3(3) . . ?
C98 C97 H97 120.3 . . ?
N92 C98 C97 122.4(3) . . ?
N92 C98 H98 118.8 . . ?
C97 C98 H98 118.8 . . ?
N92 C99 H99 118.6 . . ?
N92 C99 C100 122.9(3) . . ?
C100 C99 H99 118.6 . . ?
C96 C100 H100 120.7 . . ?
C99 C100 C96 118.5(3) . . ?
C99 C100 H100 120.7 . . ?
C85 N81 C81 118.3(3) . . ?
C89 N82 C88 118.7(3) . . ?
N81 C81 H81 118.7 . . ?
N81 C81 C82 122.6(3) . . ?
C82 C81 H81 118.7 . . ?
C81 C82 H82 120.4 . . ?
C81 C82 C83 119.2(3) . . ?
C83 C82 H82 120.4 . . ?
C82 C83 C84 118.2(3) . . ?
C82 C83 C86 120.7(3) . . ?
C84 C83 C86 121.1(3) . . ?
C83 C84 H84 120.5 . . ?
C85 C84 C83 119.0(3) . . ?
C85 C84 H84 120.5 . . ?
N81 C85 C84 122.7(3) . . ?
N81 C85 H85 118.6 . . ?
C84 C85 H85 118.6 . . ?
C87 C86 C83 120.6(3) . . ?
C87 C86 C90 118.4(3) . . ?
C90 C86 C83 121.0(3) . . ?
C86 C87 H87 120.5 . . ?
C88 C87 C86 118.9(3) . . ?
C88 C87 H87 120.5 . . ?
N82 C88 C87 122.8(3) . . ?
N82 C88 H88 118.6 . . ?
C87 C88 H88 118.6 . . ?
N82 C89 H89 118.7 . . ?
N82 C89 C90 122.6(3) . . ?
C90 C89 H89 118.7 . . ?
C86 C90 H90 120.8 . . ?
C89 C90 C86 118.5(3) . . ?
C89 C90 H90 120.8 . . ?
N21 C29A H29C 111.1 . . ?
N21 C29A H29D 111.1 . . ?
H29C C29A H29D 109.1 . . ?
C30A C29A N21 103(5) . . ?
C30A C29A H29C 111.1 . . ?
C30A C29A H29D 111.1 . . ?
C31A C30A C29A 126.2(16) . . ?
C31A C30A C35A 120.00(6) . . ?
C35A C30A C29A 113.4(16) . . ?
C30A C31A C32A 120.0 . . ?
C30A C31A Cl3 123.6(13) . . ?
C32A C31A Cl3 116.4(13) . . ?
C31A C32A H32A 120.0 . . ?
C33A C32A C31A 120.0 . . ?
C33A C32A H32A 120.0 . . ?
C32A C33A C34A 120.0 . . ?
C32A C33A Cl4 121.8(15) . . ?
C34A C33A Cl4 118.0(15) . . ?
C33A C34A H34A 120.0 . . ?
C33A C34A C35A 120.00(6) . . ?
C35A C34A H34A 120.0 . . ?
C30A C35A H35A 120.0 . . ?
C34A C35A C30A 120.0 . . ?
C34A C35A H35A 120.0 . . ?
N41 C49A H49C 110.5 . . ?
N41 C49A H49D 110.5 . . ?
N41 C49A C50A 106(2) . . ?
H49C C49A H49D 108.6 . . ?
C50A C49A H49C 110.5 . . ?
C50A C49A H49D 110.5 . . ?
C51A C50A C49A 121(2) . . ?
C51A C50A C55A 120.0 . . ?
C55A C50A C49A 116(2) . . ?
C50A C51A C52A 120.0 . . ?
C50A C51A Cl 121.3(14) . . ?
C52A C51A Cl 118.0(15) . . ?
C51A C52A H52A 120.0 . . ?
C51A C52A C53A 120.0 . . ?
C53A C52A H52A 120.0 . . ?
C52A C53A C54A 120.0 . . ?
C52A C53A Cl5 123.6(15) . . ?
C54A C53A Cl5 116.4(15) . . ?
C53A C54A H54A 120.0 . . ?
C55A C54A C53A 120.0 . . ?
C55A C54A H54A 120.0 . . ?
C50A C55A H55A 120.0 . . ?
C54A C55A C50A 120.0 . . ?
C54A C55A H55A 120.0 . . ?
C71A C70A C75A 120.0 . . ?
C71A C70A C69A 127(3) . . ?
C75A C70A C69A 112(4) . . ?
C70A C71A Cl6 122(2) . . ?
C72A C71A C70A 120.0 . . ?
C72A C71A Cl6 116(2) . . ?
C71A C72A H72A 120.0 . . ?
C73A C72A C71A 120.0 . . ?
C73A C72A H72A 120.0 . . ?
C72A C73A C74A 120.0 . . ?
C72A C73A Cl7 122(2) . . ?
C74A C73A Cl7 118(2) . . ?
C73A C74A H74A 120.0 . . ?
C73A C74A C75A 120.0 . . ?
C75A C74A H74A 120.0 . . ?
C70A C75A H75A 120.0 . . ?
C74A C75A C70A 120.0 . . ?
C74A C75A H75A 120.0 . . ?
N61 C69A C70A 121(3) . . ?
N61 C69A H69C 107.1 . . ?
N61 C69A H69D 107.1 . . ?
C70A C69A H69C 107.1 . . ?
C70A C69A H69D 107.1 . . ?
H69C C69A H69D 106.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N81 0.84(4) 1.74(4) 2.564(3) 165(4) .
O41 H41 N91 0.996(18) 1.548(19) 2.543(3) 176(3) .
O21 H21 N82 0.94(4) 1.65(4) 2.575(3) 168(3) .
O61 H61 N92 0.82(4) 1.78(4) 2.593(3) 170(4) .

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.007 0.250 -0.922 102.4 41.2 ?
2 0.007 0.750 -0.739 102.4 41.2 ?
3 0.500 0.000 -0.053 103.9 44.0 ?
4 0.500 0.500 -0.645 103.9 44.0 ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted in oil on a MITIGEN holder'
_olex2_submission_original_sample_id 'L3-78-A rpt'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.494
_oxdiff_exptl_absorpt_empirical_full_min 0.550
####################################################################### 
# 
# 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_LON-HALO
_database_code_depnum_ccdc_archive 'CCDC 1531951'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Cl2 N2 O2, C21 H24 Cl F N O2, 3(H2 O)'
_chemical_formula_sum            'C36 H39 Cl3 F N3 O7'
_chemical_formula_weight         751.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36 H33 N3 O5 Cl3 f'
_chemical_oxdiff_usercomment     l3-97-a
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.8612(5)
_cell_length_b                   10.8847(3)
_cell_length_c                   39.3807(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.781(3)
_cell_angle_gamma                90
_cell_volume                     7075.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13186
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8570
_cell_measurement_theta_min      2.8570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3136
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-23 -1 -2 0.0981
14 -12 -3 0.0544
0 0 -54 0.0157
0 0 54 0.0157
1 15 10 0.0300

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.146
_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
-23.0411 -0.9719 -2.3750 0.1596 -0.0251 -0.9893
13.9967 -11.9969 -2.6935 -0.8890 0.1192 0.3996
-0.2684 0.1094 -53.8430 -0.1466 -0.9476 -0.2571
0.2684 -0.1094 53.8430 0.1466 0.9476 0.2571
1.0618 14.9640 10.3287 0.9469 -0.0286 0.3087

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            25559
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.452
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  93.00   0.50  175.00    --   15.17  38.00-180.00  214
  2  ω    -16.00  91.00   0.50  175.00    --   15.17  57.00-120.00  214
  3  ω    -51.00  43.00   0.50  175.00    --  -15.79  77.00  90.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0098379000
_diffrn_orient_matrix_UB_12      0.0619760000
_diffrn_orient_matrix_UB_13      0.0028982000
_diffrn_orient_matrix_UB_21      -0.0001282000
_diffrn_orient_matrix_UB_22      -0.0140295000
_diffrn_orient_matrix_UB_23      0.0175712000
_diffrn_orient_matrix_UB_31      0.0418505000
_diffrn_orient_matrix_UB_32      0.0144845000
_diffrn_orient_matrix_UB_33      0.0045963000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6509
_reflns_number_total             8099
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.585
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         8099
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+12.8711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          
'Three molecules of water present, two of which are disordered over two positions in approximate ratios 60:40 and 59:41.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Others
 Sof(O43A)=Sof(H43C)=Sof(H43D)=1-FVAR(1)
 Sof(O43)=Sof(H43A)=Sof(H43B)=FVAR(1)
 Sof(O42)=Sof(H42A)=Sof(H42B)=1-FVAR(2)
 Sof(O42A)=Sof(H42C)=Sof(H42D)=FVAR(2)
3.a Free rotating group:
 O42(H42A,H42B), O43(H43A,H43B), O42A(H42C,H42D), O43A(H43C,H43D)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B),
 C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C22(H22A),
 C23(H23), C25(H25), C26(H26), C37(H37), C38(H38), C40(H40), C41(H41)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.50812(3) 1.13721(5) 0.47381(2) 0.02985(13) Uani 1 1 d . . . . .
Cl2 Cl 0.23988(4) 1.41352(5) 0.44905(2) 0.04266(17) Uani 1 1 d . . . . .
O2 O 0.35874(8) 0.69911(13) 0.29577(4) 0.0275(3) Uani 1 1 d . . . . .
O1 O 0.38741(10) 0.88267(15) 0.27475(4) 0.0372(4) Uani 1 1 d . . . . .
N1 N 0.43758(9) 0.98681(14) 0.37684(4) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.43083(9) 0.96934(15) 0.34236(4) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.37875(11) 0.81252(19) 0.29879(5) 0.0239(4) Uani 1 1 d . . . . .
C2 C 0.39283(11) 0.86201(17) 0.33489(5) 0.0194(4) Uani 1 1 d . . . . .
C3 C 0.37331(10) 0.80822(17) 0.36529(5) 0.0175(4) Uani 1 1 d . . . . .
C4 C 0.33217(11) 0.70232(17) 0.37316(5) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.3094 0.6456 0.3555 0.026 Uiso 1 1 calc R . . . .
C5 C 0.32586(12) 0.68328(18) 0.40707(6) 0.0250(4) Uani 1 1 d . . . . .
H5 H 0.2982 0.6126 0.4127 0.030 Uiso 1 1 calc R . . . .
C6 C 0.35969(12) 0.76660(19) 0.43362(5) 0.0248(4) Uani 1 1 d . . . . .
H6 H 0.3553 0.7494 0.4568 0.030 Uiso 1 1 calc R . . . .
C7 C 0.39885(11) 0.87206(18) 0.42681(5) 0.0222(4) Uani 1 1 d . . . . .
H7 H 0.4212 0.9283 0.4446 0.027 Uiso 1 1 calc R . . . .
C8 C 0.40404(11) 0.89195(17) 0.39211(5) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.47808(11) 1.09664(17) 0.39349(5) 0.0214(4) Uani 1 1 d . . . . .
H9A H 0.5010 1.1440 0.3763 0.026 Uiso 1 1 calc R . . . .
H9B H 0.5234 1.0717 0.4124 0.026 Uiso 1 1 calc R . . . .
C10 C 0.42029(11) 1.17745(17) 0.40815(5) 0.0195(4) Uani 1 1 d . . . . .
C11 C 0.42886(12) 1.20193(17) 0.44347(5) 0.0222(4) Uani 1 1 d . . . . .
C12 C 0.37435(13) 1.27522(18) 0.45633(6) 0.0262(4) Uani 1 1 d . . . . .
H12 H 0.3814 1.2912 0.4805 0.031 Uiso 1 1 calc R . . . .
C13 C 0.30969(13) 1.32418(18) 0.43305(6) 0.0281(5) Uani 1 1 d . . . . .
C14 C 0.29876(12) 1.30353(19) 0.39777(6) 0.0293(5) Uani 1 1 d . . . . .
H14 H 0.2541 1.3388 0.3821 0.035 Uiso 1 1 calc R . . . .
C15 C 0.35435(12) 1.23026(18) 0.38565(5) 0.0244(4) Uani 1 1 d . . . . .
H15 H 0.3474 1.2157 0.3614 0.029 Uiso 1 1 calc R . . . .
Cl21 Cl 0.59464(4) 0.43580(5) 0.48915(2) 0.03506(14) Uani 1 1 d . . . . .
F21 F 0.33996(8) 0.42254(14) 0.01048(3) 0.0403(3) Uani 1 1 d . . . . .
O21 O 0.38177(12) 0.34104(14) 0.17115(4) 0.0422(4) Uani 1 1 d . . . . .
O22 O 0.57697(10) 0.33120(14) 0.32004(4) 0.0324(4) Uani 1 1 d . . . . .
H22 H 0.6170(17) 0.360(3) 0.3148(8) 0.049 Uiso 1 1 d R . . . .
N21 N 0.44577(10) 0.53725(15) 0.26528(4) 0.0183(3) Uani 1 1 d . . . . .
H21 H 0.4147(13) 0.590(2) 0.2732(5) 0.018(5) Uiso 1 1 d . . . . .
C21 C 0.34243(12) 0.4242(2) 0.04499(5) 0.0286(5) Uani 1 1 d . . . . .
C22 C 0.38902(12) 0.3374(2) 0.06555(6) 0.0289(5) Uani 1 1 d . . . . .
H22A H 0.4184 0.2774 0.0557 0.035 Uiso 1 1 calc R . . . .
C23 C 0.39177(12) 0.33990(18) 0.10087(6) 0.0255(4) Uani 1 1 d . . . . .
H23 H 0.4223 0.2796 0.1154 0.031 Uiso 1 1 calc R . . . .
C24 C 0.35006(11) 0.43042(17) 0.11551(5) 0.0209(4) Uani 1 1 d . . . . .
C25 C 0.30361(11) 0.51652(18) 0.09377(5) 0.0221(4) Uani 1 1 d . . . . .
H25 H 0.2750 0.5781 0.1034 0.027 Uiso 1 1 calc R . . . .
C26 C 0.29882(12) 0.5131(2) 0.05816(5) 0.0268(4) Uani 1 1 d . . . . .
H26 H 0.2664 0.5705 0.0433 0.032 Uiso 1 1 calc R . . . .
C27 C 0.35556(12) 0.43085(18) 0.15397(5) 0.0239(4) Uani 1 1 d . . . . .
C28 C 0.32697(12) 0.54328(19) 0.17045(5) 0.0241(4) Uani 1 1 d . . . . .
H28A H 0.2685 0.5550 0.1608 0.029 Uiso 1 1 calc R . . . .
H28B H 0.3559 0.6160 0.1640 0.029 Uiso 1 1 calc R . . . .
C29 C 0.34000(12) 0.5370(2) 0.20989(5) 0.0258(4) Uani 1 1 d . . . . .
H29A H 0.3088 0.6034 0.2183 0.031 Uiso 1 1 calc R . . . .
H29B H 0.3197 0.4574 0.2168 0.031 Uiso 1 1 calc R . . . .
C30 C 0.42927(11) 0.55052(18) 0.22654(5) 0.0213(4) Uani 1 1 d . . . . .
H30A H 0.4606 0.4875 0.2168 0.026 Uiso 1 1 calc R . . . .
H30B H 0.4483 0.6322 0.2206 0.026 Uiso 1 1 calc R . . . .
C31 C 0.53293(11) 0.56775(19) 0.28024(5) 0.0225(4) Uani 1 1 d . . . . .
H31A H 0.5440 0.6533 0.2740 0.027 Uiso 1 1 calc R . . . .
H31B H 0.5683 0.5128 0.2699 0.027 Uiso 1 1 calc R . . . .
C32 C 0.55340(12) 0.55390(18) 0.31955(5) 0.0218(4) Uani 1 1 d . . . . .
H32A H 0.5239 0.6176 0.3300 0.026 Uiso 1 1 calc R . . . .
H32B H 0.6121 0.5683 0.3279 0.026 Uiso 1 1 calc R . . . .
C33 C 0.53168(12) 0.42693(18) 0.33200(5) 0.0220(4) Uani 1 1 d . . . . .
C34 C 0.44267(12) 0.40006(19) 0.31575(5) 0.0258(4) Uani 1 1 d . . . . .
H34A H 0.4289 0.3160 0.3222 0.031 Uiso 1 1 calc R . . . .
H34B H 0.4076 0.4584 0.3252 0.031 Uiso 1 1 calc R . . . .
C35 C 0.42604(13) 0.41108(18) 0.27649(5) 0.0250(4) Uani 1 1 d . . . . .
H35A H 0.4590 0.3497 0.2670 0.030 Uiso 1 1 calc R . . . .
H35B H 0.3682 0.3930 0.2670 0.030 Uiso 1 1 calc R . . . .
C36 C 0.54597(11) 0.42515(17) 0.37155(5) 0.0203(4) Uani 1 1 d . . . . .
C37 C 0.60341(11) 0.34810(18) 0.39133(5) 0.0225(4) Uani 1 1 d . . . . .
H37 H 0.6338 0.2941 0.3799 0.027 Uiso 1 1 calc R . . . .
C38 C 0.61730(12) 0.34835(18) 0.42742(5) 0.0238(4) Uani 1 1 d . . . . .
H38 H 0.6563 0.2945 0.4405 0.029 Uiso 1 1 calc R . . . .
C39 C 0.57366(12) 0.42788(18) 0.44394(5) 0.0236(4) Uani 1 1 d . . . . .
C40 C 0.51499(12) 0.50458(18) 0.42512(5) 0.0250(4) Uani 1 1 d . . . . .
H40 H 0.4843 0.5576 0.4367 0.030 Uiso 1 1 calc R . . . .
C41 C 0.50183(12) 0.50272(19) 0.38932(5) 0.0249(4) Uani 1 1 d . . . . .
H41 H 0.4618 0.5554 0.3764 0.030 Uiso 1 1 calc R . . . .
O41 O 0.70507(14) 0.3903(3) 0.29068(6) 0.0651(7) Uani 1 1 d . . . . .
H41A H 0.751(2) 0.365(4) 0.2933(9) 0.083(12) Uiso 1 1 d . . . . .
H41B H 0.683(2) 0.388(3) 0.2706(10) 0.072(11) Uiso 1 1 d . . . . .
O42 O 0.7422(4) 0.7065(6) 0.29935(16) 0.0439(17) Uani 0.591(16) 1 d . . P A 1
H42A H 0.7318 0.6920 0.2777 0.066 Uiso 0.591(16) 1 d G . P A 1
H42B H 0.7009 0.7387 0.3052 0.066 Uiso 0.591(16) 1 d G . P A 1
O43 O 0.6637(2) 0.6349(5) 0.2317(2) 0.0464(19) Uani 0.595(15) 1 d . . P B 1
H43A H 0.6936 0.6753 0.2207 0.070 Uiso 0.595(15) 1 d G . P B 1
H43B H 0.6479 0.5693 0.2208 0.070 Uiso 0.595(15) 1 d G . P B 1
O42A O 0.7150(4) 0.6628(9) 0.2833(3) 0.049(3) Uani 0.409(16) 1 d . . P A 2
H42C H 0.7375 0.6062 0.2967 0.074 Uiso 0.409(16) 1 d G . P A 2
H42D H 0.7144 0.6429 0.2624 0.074 Uiso 0.409(16) 1 d G . P A 2
O43A O 0.6606(3) 0.6588(5) 0.2108(3) 0.048(2) Uani 0.405(15) 1 d . . P B 2
H43C H 0.6250 0.6027 0.2057 0.071 Uiso 0.405(15) 1 d G . P B 2
H43D H 0.6825 0.6710 0.1935 0.071 Uiso 0.405(15) 1 d G . P B 2


_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 C11 1.748(2) . ?
Cl2 C13 1.741(2) . ?
O2 C1 1.279(2) . ?
O1 C1 1.248(3) . ?
N1 N2 1.353(2) . ?
N1 C8 1.373(2) . ?
N1 C9 1.464(2) . ?
N2 C2 1.336(2) . ?
C1 C2 1.493(3) . ?
C2 C3 1.430(3) . ?
C3 C4 1.412(3) . ?
C3 C8 1.411(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.404(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.512(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
Cl21 C39 1.745(2) . ?
F21 C21 1.351(2) . ?
O21 C27 1.219(3) . ?
O22 H22 0.81(3) . ?
O22 C33 1.428(2) . ?
N21 H21 0.88(2) . ?
N21 C30 1.501(2) . ?
N21 C31 1.505(2) . ?
N21 C35 1.501(2) . ?
C21 C22 1.381(3) . ?
C21 C26 1.379(3) . ?
C22 H22A 0.9500 . ?
C22 C23 1.383(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.401(3) . ?
C24 C25 1.397(3) . ?
C24 C27 1.498(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.388(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.510(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.525(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.521(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.523(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.536(3) . ?
C33 C34 1.535(3) . ?
C33 C36 1.527(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.519(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.393(3) . ?
C36 C41 1.403(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.392(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.382(3) . ?
C39 C40 1.388(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.382(3) . ?
C41 H41 0.9500 . ?
O41 H41A 0.81(4) . ?
O41 H41B 0.80(4) . ?
O42 H42A 0.8493 . ?
O42 H42B 0.8517 . ?
O43 H43A 0.8507 . ?
O43 H43B 0.8477 . ?
O42A H42C 0.8496 . ?
O42A H42D 0.8497 . ?
O43A H43C 0.8510 . ?
O43A H43D 0.8490 . ?

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
N2 N1 C8 112.08(15) . . ?
N2 N1 C9 120.03(15) . . ?
C8 N1 C9 127.88(16) . . ?
C2 N2 N1 106.38(15) . . ?
O2 C1 C2 115.12(18) . . ?
O1 C1 O2 126.12(19) . . ?
O1 C1 C2 118.76(18) . . ?
N2 C2 C1 120.05(17) . . ?
N2 C2 C3 110.85(17) . . ?
C3 C2 C1 129.07(17) . . ?
C4 C3 C2 136.49(18) . . ?
C8 C3 C2 104.47(16) . . ?
C8 C3 C4 119.01(17) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.32(18) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.44(18) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.84(19) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 121.8 . . ?
C6 C7 C8 116.47(19) . . ?
C8 C7 H7 121.8 . . ?
N1 C8 C3 106.21(16) . . ?
N1 C8 C7 130.93(18) . . ?
C7 C8 C3 122.86(17) . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
N1 C9 C10 111.60(15) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C11 C10 C9 123.25(17) . . ?
C11 C10 C15 117.47(18) . . ?
C15 C10 C9 119.27(18) . . ?
C10 C11 Cl1 120.90(15) . . ?
C12 C11 Cl1 116.94(16) . . ?
C12 C11 C10 122.14(19) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.14(19) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 Cl2 118.42(17) . . ?
C12 C13 C14 122.01(19) . . ?
C14 C13 Cl2 119.56(17) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 H15 119.2 . . ?
C33 O22 H22 109(2) . . ?
C30 N21 H21 107.4(14) . . ?
C30 N21 C31 109.89(14) . . ?
C31 N21 H21 108.8(14) . . ?
C35 N21 H21 108.1(14) . . ?
C35 N21 C30 112.39(15) . . ?
C35 N21 C31 110.13(15) . . ?
F21 C21 C22 118.53(18) . . ?
F21 C21 C26 118.6(2) . . ?
C26 C21 C22 122.9(2) . . ?
C21 C22 H22A 120.8 . . ?
C21 C22 C23 118.32(19) . . ?
C23 C22 H22A 120.8 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.8(2) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C27 119.05(18) . . ?
C25 C24 C23 119.02(19) . . ?
C25 C24 C27 121.92(17) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.72(18) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 118.2(2) . . ?
C21 C26 H26 120.9 . . ?
C25 C26 H26 120.9 . . ?
O21 C27 C24 119.93(18) . . ?
O21 C27 C28 121.51(19) . . ?
C24 C27 C28 118.55(17) . . ?
C27 C28 H28A 108.7 . . ?
C27 C28 H28B 108.7 . . ?
C27 C28 C29 114.18(17) . . ?
H28A C28 H28B 107.6 . . ?
C29 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C28 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C30 C29 C28 111.03(16) . . ?
C30 C29 H29A 109.4 . . ?
C30 C29 H29B 109.4 . . ?
N21 C30 C29 113.00(15) . . ?
N21 C30 H30A 109.0 . . ?
N21 C30 H30B 109.0 . . ?
C29 C30 H30A 109.0 . . ?
C29 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
N21 C31 H31A 109.2 . . ?
N21 C31 H31B 109.2 . . ?
N21 C31 C32 112.12(15) . . ?
H31A C31 H31B 107.9 . . ?
C32 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
C31 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C31 C32 C33 113.22(16) . . ?
H32A C32 H32B 107.7 . . ?
C33 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
O22 C33 C32 111.90(16) . . ?
O22 C33 C34 105.48(16) . . ?
O22 C33 C36 110.10(15) . . ?
C34 C33 C32 108.37(16) . . ?
C36 C33 C32 109.81(16) . . ?
C36 C33 C34 111.11(16) . . ?
C33 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
C35 C34 C33 111.77(17) . . ?
C35 C34 H34A 109.3 . . ?
C35 C34 H34B 109.3 . . ?
N21 C35 C34 111.46(16) . . ?
N21 C35 H35A 109.3 . . ?
N21 C35 H35B 109.3 . . ?
C34 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
H35A C35 H35B 108.0 . . ?
C37 C36 C33 121.67(17) . . ?
C37 C36 C41 117.54(18) . . ?
C41 C36 C33 120.79(17) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 C36 121.50(18) . . ?
C38 C37 H37 119.3 . . ?
C37 C38 H38 120.4 . . ?
C39 C38 C37 119.15(18) . . ?
C39 C38 H38 120.4 . . ?
C38 C39 Cl21 119.66(16) . . ?
C38 C39 C40 121.02(19) . . ?
C40 C39 Cl21 119.29(16) . . ?
C39 C40 H40 120.5 . . ?
C41 C40 C39 118.99(18) . . ?
C41 C40 H40 120.5 . . ?
C36 C41 H41 119.1 . . ?
C40 C41 C36 121.78(18) . . ?
C40 C41 H41 119.1 . . ?
H41A O41 H41B 111(3) . . ?
H42A O42 H42B 109.5 . . ?
H43A O43 H43B 109.6 . . ?
H42C O42A H42D 109.4 . . ?
H43C O43A H43D 109.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'MiTeGen micromesh'
_olex2_submission_original_sample_id L3-97-A
_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 1.928
_oxdiff_exptl_absorpt_empirical_full_min 0.724
####################################################################### 
# 
# 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_LON-2APYD_ethace
_database_code_depnum_ccdc_archive 'CCDC 1531948'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Cl2 N2 O2, C5 H7 N2, C4 H8 O2'
_chemical_formula_sum            'C24 H24 Cl2 N4 O4'
_chemical_formula_weight         503.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H24 N4 Cl2 O4'
_chemical_oxdiff_usercomment     'L3-77-A repeat'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   10.9724(3)
_cell_length_b                   13.1874(3)
_cell_length_c                   8.8415(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.768(3)
_cell_angle_gamma                90
_cell_volume                     1203.95(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6751
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.0750
_cell_measurement_theta_min      3.0090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             524
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-15 -2 0 0.0759
14 2 0 0.0621
-7 3 12 0.5308
6 -3 -12 0.5132
0 -18 -1 0.0373
0 19 0 0.0452

_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.129
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
-15.0016 -1.9772 -0.0307 0.7542 -0.5943 0.3908
14.0015 1.9793 0.0285 -0.6997 0.5603 -0.3663
-7.0190 3.0483 11.9949 0.3711 -0.3006 -0.8625
6.0189 -3.0462 -11.9971 -0.3166 0.2666 0.8871
-0.0042 -18.0735 -0.9920 -0.5597 -0.7457 0.2869
0.0062 19.0757 -0.0094 0.6000 0.8038 -0.2148

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9927
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  50.00   0.50   30.00    --   21.04 -38.00 -60.00  212
  2  ω    -14.00 103.00   0.50   30.00    --   21.04  77.00  90.00  234
  3  ω    -56.00  50.00   0.50   30.00    --   21.04 -38.00  30.00  212
  4  ω    -51.00 -26.00   0.50   30.00    --  -21.82  38.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0544007000
_diffrn_orient_matrix_UB_12      0.0314672000
_diffrn_orient_matrix_UB_13      -0.0088905000
_diffrn_orient_matrix_UB_21      0.0340944000
_diffrn_orient_matrix_UB_22      0.0421163000
_diffrn_orient_matrix_UB_23      -0.0158097000
_diffrn_orient_matrix_UB_31      -0.0243922000
_diffrn_orient_matrix_UB_32      -0.0112941000
_diffrn_orient_matrix_UB_33      -0.0833122000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.830
_reflns_Friedel_fraction_max     0.808
_reflns_number_gt                4827
_reflns_number_total             4992
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.268
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 2018 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4992
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.051
_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)+(0.0450P)²+0.2245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C22(H22A),
 C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.95781(7) 0.76698(5) 0.58787(10) 0.03489(19) Uani 1 1 d . . . . .
Cl2 Cl 1.19125(6) 1.09743(5) 0.46618(7) 0.02860(16) Uani 1 1 d . . . . .
O1 O 0.51470(19) 0.90293(13) 0.0245(2) 0.0215(4) Uani 1 1 d . . . . .
O2 O 0.4585(2) 0.73878(14) -0.0018(2) 0.0238(4) Uani 1 1 d . . . . .
N1 N 0.6712(2) 0.84530(16) 0.5000(2) 0.0183(4) Uani 1 1 d . . . . .
N2 N 0.6285(2) 0.87903(16) 0.3478(2) 0.0170(4) Uani 1 1 d . . . . .
C1 C 0.5089(2) 0.81548(19) 0.0799(3) 0.0176(5) Uani 1 1 d . . . . .
C2 C 0.5673(2) 0.80207(17) 0.2573(3) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.5695(2) 0.71430(19) 0.3532(3) 0.0173(5) Uani 1 1 d . . . . .
C4 C 0.5217(3) 0.6152(2) 0.3251(3) 0.0229(5) Uani 1 1 d . . . . .
H4 H 0.4737 0.5928 0.2196 0.028 Uiso 1 1 calc R . . . .
C5 C 0.5462(3) 0.5510(2) 0.4553(4) 0.0281(6) Uani 1 1 d . . . . .
H5 H 0.5152 0.4832 0.4391 0.034 Uiso 1 1 calc R . . . .
C6 C 0.6168(3) 0.5846(2) 0.6120(4) 0.0305(6) Uani 1 1 d . . . . .
H6 H 0.6324 0.5384 0.6990 0.037 Uiso 1 1 calc R . . . .
C7 C 0.6633(3) 0.6811(2) 0.6431(3) 0.0263(6) Uani 1 1 d . . . . .
H7 H 0.7103 0.7032 0.7492 0.032 Uiso 1 1 calc R . . . .
C8 C 0.6383(3) 0.74623(19) 0.5103(3) 0.0194(5) Uani 1 1 d . . . . .
C9 C 0.7497(3) 0.9110(2) 0.6289(3) 0.0215(5) Uani 1 1 d . . . . .
H9A H 0.7837 0.8713 0.7295 0.026 Uiso 1 1 calc R . . . .
H9B H 0.6949 0.9661 0.6469 0.026 Uiso 1 1 calc R . . . .
C10 C 0.8609(3) 0.9564(2) 0.5895(3) 0.0205(5) Uani 1 1 d . . . . .
C11 C 0.9588(3) 0.89791(19) 0.5662(3) 0.0230(5) Uani 1 1 d . . . . .
C12 C 1.0596(3) 0.9404(2) 0.5267(3) 0.0252(6) Uani 1 1 d . . . . .
H12 H 1.1243 0.8989 0.5091 0.030 Uiso 1 1 calc R . . . .
C13 C 1.0636(3) 1.0444(2) 0.5135(3) 0.0230(5) Uani 1 1 d . . . . .
C14 C 0.9702(3) 1.1063(2) 0.5391(3) 0.0243(5) Uani 1 1 d . . . . .
H14 H 0.9751 1.1779 0.5317 0.029 Uiso 1 1 calc R . . . .
C15 C 0.8695(3) 1.0613(2) 0.5757(3) 0.0234(5) Uani 1 1 d . . . . .
H15 H 0.8044 1.1030 0.5919 0.028 Uiso 1 1 calc R . . . .
N21 N 0.4656(2) 0.92787(18) 0.6971(3) 0.0222(5) Uani 1 1 d . . . . .
H21A H 0.482(3) 0.978(3) 0.650(4) 0.027 Uiso 1 1 d R . . . .
H21B H 0.493(3) 0.923(2) 0.810(4) 0.027 Uiso 1 1 d R . . . .
N22 N 0.3633(2) 0.77382(16) 0.6830(3) 0.0179(4) Uani 1 1 d . . . . .
H22 H 0.397(3) 0.769(2) 0.792(4) 0.022 Uiso 1 1 d R . . . .
C21 C 0.3924(2) 0.85521(19) 0.6081(3) 0.0182(5) Uani 1 1 d . . . . .
C22 C 0.3425(3) 0.8580(2) 0.4384(3) 0.0204(5) Uani 1 1 d . . . . .
H22A H 0.3607 0.9141 0.3819 0.025 Uiso 1 1 calc R . . . .
C23 C 0.2680(3) 0.7795(2) 0.3562(3) 0.0250(6) Uani 1 1 d . . . . .
H23 H 0.2352 0.7809 0.2421 0.030 Uiso 1 1 calc R . . . .
C24 C 0.2394(3) 0.6968(2) 0.4387(3) 0.0268(6) Uani 1 1 d . . . . .
H24 H 0.1866 0.6426 0.3819 0.032 Uiso 1 1 calc R . . . .
C25 C 0.2887(3) 0.6963(2) 0.6005(3) 0.0237(5) Uani 1 1 d . . . . .
H25 H 0.2710 0.6406 0.6579 0.028 Uiso 1 1 calc R . . . .
O31 O 1.0858(3) 0.5210(2) 0.5793(4) 0.0658(9) Uani 1 1 d . . . . .
O32 O 0.9826(2) 0.37476(15) 0.5514(3) 0.0328(5) Uani 1 1 d . . . . .
C31 C 1.1602(3) 0.3850(3) 0.4589(4) 0.0390(8) Uani 1 1 d . . . . .
H31A H 1.1170 0.3245 0.4009 0.058 Uiso 1 1 calc GR . . . .
H31B H 1.2416 0.3653 0.5419 0.058 Uiso 1 1 calc GR . . . .
H31C H 1.1785 0.4320 0.3834 0.058 Uiso 1 1 calc GR . . . .
C32 C 1.0750(3) 0.4352(2) 0.5351(4) 0.0308(6) Uani 1 1 d . . . . .
C33 C 0.8962(4) 0.4186(3) 0.6260(5) 0.0434(9) Uani 1 1 d . . . . .
H33A H 0.8438 0.4730 0.5568 0.052 Uiso 1 1 calc R . . . .
H33B H 0.9468 0.4486 0.7311 0.052 Uiso 1 1 calc R . . . .
C34 C 0.8100(4) 0.3378(3) 0.6487(5) 0.0414(8) Uani 1 1 d . . . . .
H34A H 0.7611 0.3079 0.5443 0.062 Uiso 1 1 calc GR . . . .
H34B H 0.7497 0.3669 0.6971 0.062 Uiso 1 1 calc GR . . . .
H34C H 0.8623 0.2852 0.7196 0.062 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 C11 1.738(3) . ?
Cl2 C13 1.738(3) . ?
O1 C1 1.263(3) . ?
O2 C1 1.257(3) . ?
N1 N2 1.342(3) . ?
N1 C8 1.367(3) . ?
N1 C9 1.460(3) . ?
N2 C2 1.326(3) . ?
C1 C2 1.491(3) . ?
C2 C3 1.430(3) . ?
C3 C4 1.399(4) . ?
C3 C8 1.403(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.411(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.365(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.405(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.502(4) . ?
C10 C11 1.394(4) . ?
C10 C15 1.394(4) . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 C14 1.387(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(4) . ?
C15 H15 0.9500 . ?
N21 H21A 0.83(4) . ?
N21 H21B 0.94(4) . ?
N21 C21 1.325(3) . ?
N22 H22 0.91(3) . ?
N22 C21 1.355(3) . ?
N22 C25 1.357(3) . ?
C21 C22 1.414(4) . ?
C22 H22A 0.9500 . ?
C22 C23 1.366(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.406(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.347(4) . ?
C25 H25 0.9500 . ?
O31 C32 1.190(4) . ?
O32 C32 1.336(4) . ?
O32 C33 1.446(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C31 C32 1.481(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.482(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 112.0(2) . . ?
N2 N1 C9 120.0(2) . . ?
C8 N1 C9 127.9(2) . . ?
C2 N2 N1 106.6(2) . . ?
O1 C1 C2 117.1(2) . . ?
O2 C1 O1 125.6(2) . . ?
O2 C1 C2 117.3(2) . . ?
N2 C2 C1 119.6(2) . . ?
N2 C2 C3 111.0(2) . . ?
C3 C2 C1 129.4(2) . . ?
C4 C3 C2 136.1(2) . . ?
C4 C3 C8 120.0(2) . . ?
C8 C3 C2 103.9(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.3(3) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 H7 121.7 . . ?
C6 C7 C8 116.6(3) . . ?
C8 C7 H7 121.7 . . ?
N1 C8 C3 106.6(2) . . ?
N1 C8 C7 131.2(2) . . ?
C3 C8 C7 122.1(2) . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
N1 C9 C10 111.5(2) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C11 C10 C9 122.8(2) . . ?
C11 C10 C15 117.3(3) . . ?
C15 C10 C9 120.0(2) . . ?
C10 C11 Cl1 120.0(2) . . ?
C12 C11 Cl1 117.7(2) . . ?
C12 C11 C10 122.3(2) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.3(2) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 Cl2 118.1(2) . . ?
C12 C13 C14 121.6(3) . . ?
C14 C13 Cl2 120.2(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.9(3) . . ?
C14 C15 H15 119.1 . . ?
H21A N21 H21B 122(3) . . ?
C21 N21 H21A 118(2) . . ?
C21 N21 H21B 119(2) . . ?
C21 N22 H22 120(2) . . ?
C21 N22 C25 122.2(2) . . ?
C25 N22 H22 118(2) . . ?
N21 C21 N22 118.6(2) . . ?
N21 C21 C22 123.4(2) . . ?
N22 C21 C22 118.0(2) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 H22A 120.3 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.7(3) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.8 . . ?
C25 C24 C23 118.3(3) . . ?
C25 C24 H24 120.8 . . ?
N22 C25 H25 119.3 . . ?
C24 C25 N22 121.3(3) . . ?
C24 C25 H25 119.3 . . ?
C32 O32 C33 116.7(2) . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
O31 C32 O32 121.8(3) . . ?
O31 C32 C31 124.5(3) . . ?
O32 C32 C31 113.6(3) . . ?
O32 C33 H33A 109.9 . . ?
O32 C33 H33B 109.9 . . ?
O32 C33 C34 108.7(3) . . ?
H33A C33 H33B 108.3 . . ?
C34 C33 H33A 109.9 . . ?
C34 C33 H33B 109.9 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9B O1 0.99 2.57 3.451(3) 147.9 2_575
C14 H14 O32 0.95 2.60 3.544(3) 171.6 1_565
N21 H21A O1 0.83(4) 2.03(4) 2.856(3) 177(3) 2_575
N21 H21B O1 0.94(4) 1.85(4) 2.779(3) 169(3) 1_556
N22 H22 O2 0.91(3) 1.76(3) 2.665(3) 171(3) 1_556
C25 H25 O31 0.95 2.48 3.171(4) 129.7 1_455

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-27
_olex2_exptl_crystal_mounting_method 'MiTeGen Micromesh'
_olex2_submission_original_sample_id L3-77-A_repeat
_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 1.691
_oxdiff_exptl_absorpt_empirical_full_min 0.535
####################################################################### 
# 
# 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_LON-IMID_1-1
_database_code_depnum_ccdc_archive 'CCDC 1531952'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2017-02-09data_
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C15 H9.5 Cl2 N2 O2, C15 H9 Cl2 N2 O2, C3 H5 N2, C3 H4.5 N2'
_chemical_formula_sum            'C36 H28 Cl4 N8 O4'
_chemical_formula_weight         778.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C33 H27 N6 O4 Cl4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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'

_symmetry_space_group_name_H-M_alt 'P -1'
_cell_length_a                   10.0605(5)
_cell_length_b                   11.0252(6)
_cell_length_c                   16.3298(10)
_cell_angle_alpha                88.224(4)
_cell_angle_beta                 76.212(5)
_cell_angle_gamma                84.969(4)
_cell_volume                     1752.21(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8129
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.7870
_cell_measurement_theta_min      2.1310
_cell_oxdiff_angle_alpha         88.224(4)
_cell_oxdiff_angle_beta          76.212(5)
_cell_oxdiff_angle_gamma         84.969(4)
_cell_oxdiff_length_a            10.0605(5)
_cell_oxdiff_length_b            11.0252(6)
_cell_oxdiff_length_c            16.3298(10)
_cell_oxdiff_measurement_reflns_used 8129
_cell_oxdiff_volume              1752.21(17)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chip
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21522
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.180
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  73.00   1.00  100.00    --  -17.00  72.00  30.00  100
  2  ω    -69.00  22.00   1.00  100.00    --  -17.00 -72.00 -90.00   91
  3  ω    -68.00  22.00   1.00  100.00    --  -17.00 -72.00  90.00   90
  4  ω    -54.00  23.00   1.00  100.00    --  -17.00   0.00  60.00   77
  5  ω    -32.00 -16.00   1.00  100.00    --  -17.00  54.00-120.00   16
  6  ω    -31.00  73.00   1.00  100.00    --  -17.00  72.00 120.00  104
  7  ω    -69.00  15.00   1.00  100.00    --  -17.00 -72.00   0.00   84
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC10 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438142000
_diffrn_orient_matrix_UB_12      0.0532728000
_diffrn_orient_matrix_UB_13      -0.0026151000
_diffrn_orient_matrix_UB_21      0.0283301000
_diffrn_orient_matrix_UB_22      0.0291238000
_diffrn_orient_matrix_UB_23      0.0292600000
_diffrn_orient_matrix_UB_31      0.0508344000
_diffrn_orient_matrix_UB_32      0.0220286000
_diffrn_orient_matrix_UB_33      -0.0337273000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5735
_reflns_number_total             8029
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.370
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         8029
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.039
_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)+(0.0789P)²+0.4823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1521
_refine_special_details          
'2 independent molecules of each lonidamine and imidazole present. One imidazole is fully ordered and contains a half occupied proton giving an overall +0.5 charge. This charge balances with the lonidamine moiety which also contains a half occupied proton on the carboxylic acid. The second lonidamine is fully deprotonated to give a 1- charge and the second imidazole is fully protonated to give a 1+ charge. Full molecule disorder present of the second imidazole in an approximate 50:50 ratio.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 N45A, H45A, N46A, H46A, C45A, H45B, C46A, H46B, C47A, H47A, N45, H45, N46,
 H46, C45, H45C, C46, H46C, C47, H47
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(N45A)=Sof(H45A)=Sof(N46A)=Sof(H46A)=Sof(C45A)=Sof(H45B)=Sof(C46A)=
 Sof(H46B)=Sof(C47A)=Sof(H47A)=1-FVAR(1)
 Sof(N45)=Sof(H45)=Sof(N46)=Sof(H46)=Sof(C45)=Sof(H45C)=Sof(C46)=Sof(H46C)=
 Sof(C47)=Sof(H47)=FVAR(1)
 Fixed Sof: H1(0.5) H42(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C29(H29A,H29B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C24(H24),
 C25(H25), C26(H26), C27(H27), C32(H32), C34(H34), C35(H35), N45A(H45A),
 N46A(H46A), C45A(H45B), C46A(H46B), C47A(H47A), N45(H45), C45(H45C), C46(H46C),
  C47(H47), N42(H42), C41(H41A), C42(H42A), C43(H43)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.58701(7) 0.39131(6) 0.67596(5) 0.04254(19) Uani 1 1 d . . . . .
Cl2 Cl 1.05944(8) 0.32425(7) 0.44170(5) 0.0482(2) Uani 1 1 d . . . . .
O1 O 0.9392(2) 0.02005(15) 0.94053(12) 0.0410(5) Uani 1 1 d . . . . .
H1 H 0.983(8) 0.003(7) 0.982(4) 0.05(2) Uiso 0.5 1 d . . P . .
O2 O 0.9511(3) -0.18123(17) 0.92856(14) 0.0585(6) Uani 1 1 d . . . . .
N1 N 0.6974(2) 0.02455(18) 0.77140(13) 0.0302(5) Uani 1 1 d . . . . .
N2 N 0.7755(2) 0.04493(18) 0.82593(12) 0.0297(5) Uani 1 1 d . . . . .
C1 C 0.9111(3) -0.0784(2) 0.90983(16) 0.0362(6) Uani 1 1 d . . . . .
C2 C 0.8259(2) -0.0636(2) 0.84735(15) 0.0283(5) Uani 1 1 d . . . . .
C3 C 0.7814(2) -0.1582(2) 0.80539(15) 0.0301(5) Uani 1 1 d . . . . .
C4 C 0.7997(3) -0.2856(2) 0.80458(16) 0.0343(6) Uani 1 1 d . . . . .
H4 H 0.8559 -0.3284 0.8370 0.041 Uiso 1 1 calc R . . . .
C5 C 0.7342(3) -0.3470(2) 0.75576(18) 0.0409(7) Uani 1 1 d . . . . .
H5 H 0.7450 -0.4335 0.7546 0.049 Uiso 1 1 calc R . . . .
C6 C 0.6518(3) -0.2839(3) 0.7078(2) 0.0476(8) Uani 1 1 d . . . . .
H6 H 0.6073 -0.3292 0.6752 0.057 Uiso 1 1 calc R . . . .
C7 C 0.6328(3) -0.1594(3) 0.70585(18) 0.0424(7) Uani 1 1 d . . . . .
H7 H 0.5780 -0.1173 0.6723 0.051 Uiso 1 1 calc R . . . .
C8 C 0.6995(3) -0.0974(2) 0.75669(16) 0.0320(5) Uani 1 1 d . . . . .
C9 C 0.6384(3) 0.1263(2) 0.73092(16) 0.0343(6) Uani 1 1 d . . . . .
H9A H 0.6032 0.1918 0.7725 0.041 Uiso 1 1 calc R . . . .
H9B H 0.5597 0.1005 0.7111 0.041 Uiso 1 1 calc R . . . .
C10 C 0.7419(2) 0.1758(2) 0.65646(15) 0.0279(5) Uani 1 1 d . . . . .
C11 C 0.7274(2) 0.2948(2) 0.62790(16) 0.0306(5) Uani 1 1 d . . . . .
C12 C 0.8232(3) 0.3424(2) 0.56208(17) 0.0346(6) Uani 1 1 d . . . . .
H12 H 0.8112 0.4245 0.5439 0.042 Uiso 1 1 calc R . . . .
C13 C 0.9356(3) 0.2680(2) 0.52384(16) 0.0350(6) Uani 1 1 d . . . . .
C14 C 0.9537(3) 0.1487(2) 0.54922(16) 0.0352(6) Uani 1 1 d . . . . .
H14 H 1.0319 0.0980 0.5218 0.042 Uiso 1 1 calc R . . . .
C15 C 0.8566(3) 0.1037(2) 0.61510(16) 0.0329(6) Uani 1 1 d . . . . .
H15 H 0.8688 0.0213 0.6325 0.039 Uiso 1 1 calc R . . . .
Cl21 Cl 0.15140(7) 0.94564(6) 0.64950(5) 0.0467(2) Uani 1 1 d . . . . .
Cl22 Cl 0.61056(7) 0.80941(6) 0.41656(4) 0.04354(19) Uani 1 1 d . . . . .
O21 O 0.4978(2) 0.51240(16) 0.88449(12) 0.0411(5) Uani 1 1 d . . . . .
O22 O 0.4457(2) 0.31832(16) 0.89043(12) 0.0451(5) Uani 1 1 d . . . . .
N21 N 0.1950(2) 0.57676(18) 0.75854(13) 0.0307(5) Uani 1 1 d . . . . .
N22 N 0.2993(2) 0.57535(18) 0.79871(13) 0.0315(5) Uani 1 1 d . . . . .
C21 C 0.4286(3) 0.4268(2) 0.87043(16) 0.0360(6) Uani 1 1 d . . . . .
C22 C 0.3188(3) 0.4623(2) 0.82482(15) 0.0311(5) Uani 1 1 d . . . . .
C23 C 0.2271(3) 0.3864(2) 0.80129(15) 0.0306(5) Uani 1 1 d . . . . .
C24 C 0.2009(3) 0.2631(2) 0.81251(17) 0.0399(6) Uani 1 1 d . . . . .
H24 H 0.2520 0.2091 0.8423 0.048 Uiso 1 1 calc R . . . .
C25 C 0.0997(3) 0.2227(2) 0.77946(18) 0.0443(7) Uani 1 1 d . . . . .
H25 H 0.0802 0.1398 0.7868 0.053 Uiso 1 1 calc R . . . .
C26 C 0.0251(3) 0.3015(2) 0.73526(18) 0.0424(7) Uani 1 1 d . . . . .
H26 H -0.0435 0.2700 0.7127 0.051 Uiso 1 1 calc R . . . .
C27 C 0.0466(3) 0.4228(2) 0.72295(17) 0.0377(6) Uani 1 1 d . . . . .
H27 H -0.0048 0.4759 0.6928 0.045 Uiso 1 1 calc R . . . .
C28 C 0.1495(3) 0.4634(2) 0.75793(15) 0.0302(5) Uani 1 1 d . . . . .
C29 C 0.1592(3) 0.6865(2) 0.71602(17) 0.0332(6) Uani 1 1 d . . . . .
H29A H 0.1411 0.7551 0.7560 0.040 Uiso 1 1 calc R . . . .
H29B H 0.0738 0.6773 0.6976 0.040 Uiso 1 1 calc R . . . .
C30 C 0.2713(2) 0.7161(2) 0.64016(15) 0.0285(5) Uani 1 1 d . . . . .
C31 C 0.2763(3) 0.8328(2) 0.60509(17) 0.0321(6) Uani 1 1 d . . . . .
C32 C 0.3783(3) 0.8632(2) 0.53641(16) 0.0345(6) Uani 1 1 d . . . . .
H32 H 0.3787 0.9435 0.5136 0.041 Uiso 1 1 calc R . . . .
C33 C 0.4797(3) 0.7740(2) 0.50180(16) 0.0330(6) Uani 1 1 d . . . . .
C34 C 0.4784(3) 0.6572(2) 0.53442(16) 0.0335(6) Uani 1 1 d . . . . .
H34 H 0.5485 0.5965 0.5103 0.040 Uiso 1 1 calc R . . . .
C35 C 0.3743(3) 0.6291(2) 0.60248(16) 0.0318(6) Uani 1 1 d . . . . .
H35 H 0.3732 0.5481 0.6241 0.038 Uiso 1 1 calc R . . . .
N45A N 0.7297(15) 0.4248(12) 0.9313(11) 0.025(2) Uani 0.495(7) 1 d . U P A 2
H45A H 0.6648 0.4511 0.9057 0.030 Uiso 0.495(7) 1 calc R U P A 2
N46A N 0.8760(7) 0.3053(6) 0.9805(5) 0.0332(18) Uani 0.495(7) 1 d . U P A 2
H46A H 0.9245 0.2400 0.9930 0.040 Uiso 0.495(7) 1 calc R U P A 2
C45A C 0.7817(8) 0.3067(6) 0.9365(4) 0.0324(14) Uani 0.495(7) 1 d . U P A 2
H45B H 0.7547 0.2380 0.9127 0.039 Uiso 0.495(7) 1 calc R U P A 2
C46A C 0.8863(5) 0.4218(6) 1.0037(4) 0.0342(15) Uani 0.495(7) 1 d . U P A 2
H46B H 0.9464 0.4464 1.0358 0.041 Uiso 0.495(7) 1 calc R U P A 2
C47A C 0.7969(10) 0.4937(7) 0.9731(6) 0.0330(18) Uani 0.495(7) 1 d . U P A 2
H47A H 0.7822 0.5796 0.9793 0.040 Uiso 0.495(7) 1 calc R U P A 2
N45 N 0.2908(17) 0.5925(13) 0.0729(12) 0.028(2) Uani 0.505(7) 1 d . U P A 1
H45 H 0.3603 0.5469 0.0846 0.033 Uiso 0.505(7) 1 calc R U P A 1
N46 N 0.1541(5) 0.7457(5) 0.0624(3) 0.0289(14) Uani 0.505(7) 1 d . U P A 1
H46 H 0.113(6) 0.822(6) 0.062(4) 0.045(17) Uiso 0.505(7) 1 d . U P A 1
C45 C 0.2659(6) 0.7048(5) 0.0882(4) 0.0292(13) Uani 0.505(7) 1 d . U P A 1
H45C H 0.3185 0.7525 0.1139 0.035 Uiso 0.505(7) 1 calc R U P A 1
C46 C 0.1085(8) 0.6499(7) 0.0273(6) 0.0288(17) Uani 0.505(7) 1 d . U P A 1
H46C H 0.0320 0.6527 0.0025 0.035 Uiso 0.505(7) 1 calc R U P A 1
C47 C 0.1947(9) 0.5510(7) 0.0354(6) 0.0292(17) Uani 0.505(7) 1 d . U P A 1
H47 H 0.1898 0.4700 0.0187 0.035 Uiso 0.505(7) 1 calc R U P A 1
N41 N 0.5749(2) 0.2399(2) 0.10648(14) 0.0364(5) Uani 1 1 d . . . . .
H41 H 0.565(4) 0.321(3) 0.117(2) 0.080(12) Uiso 1 1 d . . . . .
N42 N 0.5451(2) 0.07398(19) 0.04684(14) 0.0390(5) Uani 1 1 d . . . . .
H42 H 0.5153 0.0230 0.0163 0.047 Uiso 0.5 1 calc R . P . .
C41 C 0.5106(3) 0.1921(2) 0.05435(15) 0.0314(5) Uani 1 1 d . . . . .
H41A H 0.4487 0.2366 0.0265 0.038 Uiso 1 1 calc R . . . .
C42 C 0.6362(4) 0.0467(3) 0.0958(2) 0.0562(9) Uani 1 1 d . . . . .
H42A H 0.6799 -0.0316 0.1027 0.067 Uiso 1 1 calc R . . . .
C43 C 0.6539(4) 0.1500(3) 0.1332(2) 0.0544(8) Uani 1 1 d . . . . .
H43 H 0.7113 0.1575 0.1710 0.065 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.733(3) . ?
Cl2 C13 1.739(3) . ?
O1 H1 0.90(6) . ?
O1 C1 1.290(3) . ?
O2 C1 1.224(3) . ?
N1 N2 1.355(3) . ?
N1 C8 1.371(3) . ?
N1 C9 1.439(3) . ?
N2 C2 1.328(3) . ?
C1 C2 1.478(3) . ?
C2 C3 1.425(3) . ?
C3 C4 1.401(3) . ?
C3 C8 1.394(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.370(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.410(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.522(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.386(3) . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.369(4) . ?
C13 C14 1.377(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(4) . ?
C15 H15 0.9500 . ?
Cl21 C31 1.732(3) . ?
Cl22 C33 1.734(3) . ?
O21 C21 1.278(3) . ?
O22 C21 1.238(3) . ?
N21 N22 1.362(3) . ?
N21 C28 1.369(3) . ?
N21 C29 1.438(3) . ?
N22 C22 1.318(3) . ?
C21 C22 1.493(3) . ?
C22 C23 1.423(3) . ?
C23 C24 1.405(3) . ?
C23 C28 1.393(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.372(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.394(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.375(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.406(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.512(4) . ?
C30 C31 1.392(3) . ?
C30 C35 1.390(3) . ?
C31 C32 1.383(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.382(4) . ?
C33 C34 1.378(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.381(4) . ?
C35 H35 0.9500 . ?
N45A H45A 0.8800 . ?
N45A C45A 1.368(16) . ?
N45A C47A 1.358(12) . ?
N46A H46A 0.8800 . ?
N46A C45A 1.319(10) . ?
N46A C46A 1.370(7) . ?
C45A H45B 0.9500 . ?
C46A H46B 0.9500 . ?
C46A C47A 1.324(10) . ?
C47A H47A 0.9500 . ?
N45 H45 0.8800 . ?
N45 C45 1.263(16) . ?
N45 C47 1.377(11) . ?
N46 H46 0.90(6) . ?
N46 C45 1.331(8) . ?
N46 C46 1.379(8) . ?
C45 H45C 0.9500 . ?
C46 H46C 0.9500 . ?
C46 C47 1.356(12) . ?
C47 H47 0.9500 . ?
N41 H41 0.91(4) . ?
N41 C41 1.331(3) . ?
N41 C43 1.343(4) . ?
N42 H42 0.8800 . ?
N42 C41 1.320(3) . ?
N42 C42 1.362(4) . ?
C41 H41A 0.9500 . ?
C42 H42A 0.9500 . ?
C42 C43 1.353(4) . ?
C43 H43 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 111(5) . . ?
N2 N1 C8 111.18(19) . . ?
N2 N1 C9 119.51(19) . . ?
C8 N1 C9 128.9(2) . . ?
C2 N2 N1 106.51(18) . . ?
O1 C1 C2 116.7(2) . . ?
O2 C1 O1 124.4(2) . . ?
O2 C1 C2 118.9(2) . . ?
N2 C2 C1 122.2(2) . . ?
N2 C2 C3 110.9(2) . . ?
C3 C2 C1 126.9(2) . . ?
C4 C3 C2 135.8(2) . . ?
C8 C3 C2 104.5(2) . . ?
C8 C3 C4 119.7(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 118.7 . . ?
C7 C6 C5 122.7(2) . . ?
C7 C6 H6 118.7 . . ?
C6 C7 H7 122.0 . . ?
C6 C7 C8 115.9(3) . . ?
C8 C7 H7 122.0 . . ?
N1 C8 C3 106.93(19) . . ?
N1 C8 C7 130.5(2) . . ?
C3 C8 C7 122.5(2) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
N1 C9 C10 112.2(2) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 C15 117.1(2) . . ?
C15 C10 C9 121.0(2) . . ?
C10 C11 Cl1 120.1(2) . . ?
C12 C11 Cl1 117.33(19) . . ?
C12 C11 C10 122.5(2) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.2(2) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 Cl2 119.8(2) . . ?
C12 C13 C14 121.4(2) . . ?
C14 C13 Cl2 118.8(2) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.1(2) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 H15 119.2 . . ?
N22 N21 C28 111.43(19) . . ?
N22 N21 C29 118.88(18) . . ?
C28 N21 C29 129.3(2) . . ?
C22 N22 N21 106.23(19) . . ?
O21 C21 C22 116.2(2) . . ?
O22 C21 O21 125.9(2) . . ?
O22 C21 C22 117.9(2) . . ?
N22 C22 C21 120.8(2) . . ?
N22 C22 C23 111.2(2) . . ?
C23 C22 C21 128.0(2) . . ?
C24 C23 C22 135.9(2) . . ?
C28 C23 C22 104.7(2) . . ?
C28 C23 C24 119.4(2) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 C23 118.4(3) . . ?
C25 C24 H24 120.8 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 118.6 . . ?
C27 C26 C25 122.7(2) . . ?
C27 C26 H26 118.6 . . ?
C26 C27 H27 122.1 . . ?
C26 C27 C28 115.7(2) . . ?
C28 C27 H27 122.1 . . ?
N21 C28 C23 106.4(2) . . ?
N21 C28 C27 130.8(2) . . ?
C23 C28 C27 122.8(2) . . ?
N21 C29 H29A 109.1 . . ?
N21 C29 H29B 109.1 . . ?
N21 C29 C30 112.3(2) . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C31 C30 C29 121.2(2) . . ?
C35 C30 C29 122.0(2) . . ?
C35 C30 C31 116.8(2) . . ?
C30 C31 Cl21 119.1(2) . . ?
C32 C31 Cl21 118.25(19) . . ?
C32 C31 C30 122.7(2) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 C31 118.4(2) . . ?
C33 C32 H32 120.8 . . ?
C32 C33 Cl22 119.70(19) . . ?
C34 C33 Cl22 119.5(2) . . ?
C34 C33 C32 120.8(2) . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.5(2) . . ?
C35 C34 H34 120.2 . . ?
C30 C35 H35 119.1 . . ?
C34 C35 C30 121.8(2) . . ?
C34 C35 H35 119.1 . . ?
C45A N45A H45A 126.4 . . ?
C47A N45A H45A 126.4 . . ?
C47A N45A C45A 107.1(10) . . ?
C45A N46A H46A 125.5 . . ?
C45A N46A C46A 109.1(6) . . ?
C46A N46A H46A 125.5 . . ?
N45A C45A H45B 126.1 . . ?
N46A C45A N45A 107.7(7) . . ?
N46A C45A H45B 126.1 . . ?
N46A C46A H46B 126.4 . . ?
C47A C46A N46A 107.2(6) . . ?
C47A C46A H46B 126.4 . . ?
N45A C47A H47A 125.6 . . ?
C46A C47A N45A 108.9(8) . . ?
C46A C47A H47A 125.6 . . ?
C45 N45 H45 124.5 . . ?
C45 N45 C47 110.9(12) . . ?
C47 N45 H45 124.5 . . ?
C45 N46 H46 130(4) . . ?
C45 N46 C46 108.2(6) . . ?
C46 N46 H46 121(4) . . ?
N45 C45 N46 109.0(8) . . ?
N45 C45 H45C 125.5 . . ?
N46 C45 H45C 125.5 . . ?
N46 C46 H46C 126.8 . . ?
C47 C46 N46 106.3(7) . . ?
C47 C46 H46C 126.8 . . ?
N45 C47 H47 127.2 . . ?
C46 C47 N45 105.5(9) . . ?
C46 C47 H47 127.2 . . ?
C41 N41 H41 122(2) . . ?
C41 N41 C43 108.0(2) . . ?
C43 N41 H41 130(2) . . ?
C41 N42 H42 126.8 . . ?
C41 N42 C42 106.4(2) . . ?
C42 N42 H42 126.8 . . ?
N41 C41 H41A 124.9 . . ?
N42 C41 N41 110.3(2) . . ?
N42 C41 H41A 124.9 . . ?
N42 C42 H42A 125.7 . . ?
C43 C42 N42 108.5(3) . . ?
C43 C42 H42A 125.7 . . ?
N41 C43 C42 106.8(3) . . ?
N41 C43 H43 126.6 . . ?
C42 C43 H43 126.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.90(6) 1.64(6) 2.539(4) 177(8) 2_757
C9 H9A O22 0.99 2.55 3.499(3) 161.2 .
N41 H41 O21 0.91(4) 1.89(4) 2.763(3) 160(3) 2_666
N41 H41 N22 0.91(4) 2.51(4) 3.119(3) 124(3) 2_666
N42 H42 N42 0.88 1.75 2.627(4) 177.9 2_655
C41 H41A O22 0.95 2.38 3.158(3) 139.0 1_554

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_original_sample_id L3-85-C2
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.262
_oxdiff_exptl_absorpt_empirical_full_min 0.442
####################################################################### 
# 
# 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_LON-BENZ
_database_code_depnum_ccdc_archive 'CCDC 1531954'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-05-20
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl2 N2 O2, C7 H7 N O'
_chemical_formula_sum            'C22 H17 Cl2 N3 O3'
_chemical_formula_weight         442.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H17 O3 N3 Cl2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   18.3534(8)
_cell_length_b                   10.1000(3)
_cell_length_c                   11.0376(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.146(4)
_cell_angle_gamma                90
_cell_volume                     2020.02(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15447
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.7520
_cell_measurement_theta_min      2.2990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            33938
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.309
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  73.00   1.00   50.00    --  -17.00  72.00 -90.00  100
  2  ω    -69.00  22.00   1.00   50.00    --  -17.00 -72.00 150.00   91
  3  ω    -68.00  22.00   1.00   50.00    --  -17.00 -72.00 -30.00   90
  4  ω    -85.00  -4.00   1.00   50.00    --  -17.00   0.00 -30.00   81
  5  ω    -31.00 -14.00   1.00   50.00    --  -17.00  54.00 120.00   17
  6  ω    -31.00  73.00   1.00   50.00    --  -17.00  72.00  60.00  104
  7  ω    -69.00  22.00   1.00   50.00    --  -17.00 -72.00 -60.00   91
  8  ω    -68.00  22.00   1.00   50.00    --  -17.00 -72.00 120.00   90
  9  ω    -81.00 -12.00   1.00   50.00    --  -17.00   0.00 -60.00   69
 10  ω    -30.00 -14.00   1.00   50.00    --  -17.00  54.00 -90.00   16
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC10 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0020320000
_diffrn_orient_matrix_UB_12      -0.0291791000
_diffrn_orient_matrix_UB_13      -0.0577801000
_diffrn_orient_matrix_UB_21      -0.0389050000
_diffrn_orient_matrix_UB_22      -0.0079325000
_diffrn_orient_matrix_UB_23      -0.0104735000
_diffrn_orient_matrix_UB_31      -0.0040525000
_diffrn_orient_matrix_UB_32      0.0633621000
_diffrn_orient_matrix_UB_33      -0.0280344000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3764
_reflns_number_total             4631
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.506
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+1.0347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.64561(3) 0.97313(5) 0.53690(4) 0.03734(14) Uani 1 1 d . . . . .
Cl2 Cl 0.91136(3) 1.02700(6) 0.40092(6) 0.05510(18) Uani 1 1 d . . . . .
O1 O 0.75549(7) 0.36449(12) 0.62227(11) 0.0281(3) Uani 1 1 d . . . . .
H1 H 0.7811(14) 0.300(3) 0.659(2) 0.052(7) Uiso 1 1 d . . . . .
O2 O 0.66801(7) 0.31658(13) 0.73632(12) 0.0341(3) Uani 1 1 d . . . . .
N1 N 0.62059(8) 0.65441(13) 0.47282(12) 0.0223(3) Uani 1 1 d . . . . .
N2 N 0.67207(8) 0.56069(13) 0.50815(12) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.69211(9) 0.38373(16) 0.65929(15) 0.0237(3) Uani 1 1 d . . . . .
C2 C 0.64911(9) 0.49496(16) 0.59938(14) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.58026(9) 0.54496(15) 0.62364(14) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.53001(10) 0.51320(16) 0.70405(15) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.5394 0.4424 0.7610 0.030 Uiso 1 1 calc R . . . .
C5 C 0.46714(10) 0.58833(17) 0.69677(16) 0.0279(4) Uani 1 1 d . . . . .
H5 H 0.4328 0.5690 0.7503 0.034 Uiso 1 1 calc R . . . .
C6 C 0.45189(10) 0.69327(17) 0.61230(16) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.4077 0.7426 0.6103 0.032 Uiso 1 1 calc R . . . .
C7 C 0.49969(9) 0.72585(17) 0.53254(15) 0.0257(3) Uani 1 1 d . . . . .
H7 H 0.4897 0.7968 0.4758 0.031 Uiso 1 1 calc R . . . .
C8 C 0.56376(9) 0.64898(16) 0.53942(14) 0.0227(3) Uani 1 1 d . . . . .
C9 C 0.62430(10) 0.73310(17) 0.36331(15) 0.0255(3) Uani 1 1 d . . . . .
H9A H 0.5822 0.7956 0.3506 0.031 Uiso 1 1 calc R . . . .
H9B H 0.6196 0.6737 0.2912 0.031 Uiso 1 1 calc R . . . .
C10 C 0.69499(9) 0.80977(16) 0.37187(15) 0.0243(3) Uani 1 1 d . . . . .
C11 C 0.71063(10) 0.91819(17) 0.44880(16) 0.0275(4) Uani 1 1 d . . . . .
C12 C 0.77663(11) 0.98708(18) 0.45903(17) 0.0325(4) Uani 1 1 d . . . . .
H12 H 0.7867 1.0600 0.5135 0.039 Uiso 1 1 calc R . . . .
C13 C 0.82711(11) 0.94541(19) 0.38682(19) 0.0351(4) Uani 1 1 d . . . . .
C14 C 0.81348(11) 0.84092(19) 0.30635(18) 0.0345(4) Uani 1 1 d . . . . .
H14 H 0.8487 0.8156 0.2563 0.041 Uiso 1 1 calc R . . . .
C15 C 0.74747(10) 0.77367(17) 0.30002(16) 0.0287(4) Uani 1 1 d . . . . .
H15 H 0.7377 0.7010 0.2452 0.034 Uiso 1 1 calc R . . . .
O21 O 0.83518(7) 0.17068(12) 0.71207(11) 0.0303(3) Uani 1 1 d . . . . .
N21 N 0.76067(10) 0.10361(17) 0.84328(15) 0.0338(4) Uani 1 1 d . . . . .
H21A H 0.7289(12) 0.163(2) 0.8164(19) 0.034(6) Uiso 1 1 d . . . . .
H21B H 0.7514(13) 0.050(2) 0.901(2) 0.044(6) Uiso 1 1 d . . . . .
C21 C 0.82297(10) 0.09697(17) 0.79773(15) 0.0268(4) Uani 1 1 d . . . . .
C22 C 0.87882(10) -0.00372(17) 0.84884(16) 0.0280(4) Uani 1 1 d . . . . .
C23 C 0.93034(10) -0.04516(18) 0.77687(17) 0.0318(4) Uani 1 1 d . . . . .
H23 H 0.9294 -0.0094 0.6970 0.038 Uiso 1 1 calc R . . . .
C24 C 0.98312(11) -0.1388(2) 0.82191(19) 0.0387(5) Uani 1 1 d . . . . .
H24 H 1.0176 -0.1687 0.7723 0.046 Uiso 1 1 calc R . . . .
C25 C 0.98531(12) -0.1884(2) 0.9395(2) 0.0424(5) Uani 1 1 d . . . . .
H25 H 1.0218 -0.2517 0.9707 0.051 Uiso 1 1 calc R . . . .
C26 C 0.93497(13) -0.1465(2) 1.01133(19) 0.0415(5) Uani 1 1 d . . . . .
H26 H 0.9371 -0.1805 1.0920 0.050 Uiso 1 1 calc R . . . .
C27 C 0.88133(12) -0.05513(19) 0.96676(17) 0.0352(4) Uani 1 1 d . . . . .
H27 H 0.8463 -0.0274 1.0162 0.042 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7455(18) . ?
Cl2 C13 1.7373(19) . ?
O1 H1 0.86(3) . ?
O1 C1 1.307(2) . ?
O2 C1 1.224(2) . ?
N1 N2 1.3504(19) . ?
N1 C8 1.369(2) . ?
N1 C9 1.457(2) . ?
N2 C2 1.329(2) . ?
C1 C2 1.468(2) . ?
C2 C3 1.425(2) . ?
C3 C4 1.415(2) . ?
C3 C8 1.404(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.410(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.401(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.501(2) . ?
C10 C11 1.387(2) . ?
C10 C15 1.390(2) . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 C14 1.376(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9500 . ?
O21 C21 1.251(2) . ?
N21 H21A 0.85(2) . ?
N21 H21B 0.87(2) . ?
N21 C21 1.322(2) . ?
C21 C22 1.490(2) . ?
C22 C23 1.392(3) . ?
C22 C27 1.395(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.377(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 114.4(16) . . ?
N2 N1 C8 112.00(13) . . ?
N2 N1 C9 119.94(13) . . ?
C8 N1 C9 127.38(14) . . ?
C2 N2 N1 106.10(13) . . ?
O1 C1 C2 114.47(14) . . ?
O2 C1 O1 124.93(16) . . ?
O2 C1 C2 120.60(15) . . ?
N2 C2 C1 120.71(15) . . ?
N2 C2 C3 111.27(14) . . ?
C3 C2 C1 127.99(14) . . ?
C4 C3 C2 136.34(16) . . ?
C8 C3 C2 104.19(14) . . ?
C8 C3 C4 119.45(15) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.63(16) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.07(16) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.49(16) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.7 . . ?
C6 C7 C8 116.56(16) . . ?
C8 C7 H7 121.7 . . ?
N1 C8 C3 106.44(14) . . ?
N1 C8 C7 130.77(15) . . ?
C7 C8 C3 122.79(15) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
N1 C9 C10 112.52(14) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C11 C10 C9 122.58(15) . . ?
C11 C10 C15 117.47(16) . . ?
C15 C10 C9 119.94(15) . . ?
C10 C11 Cl1 119.90(14) . . ?
C12 C11 Cl1 117.46(14) . . ?
C12 C11 C10 122.64(17) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.26(17) . . ?
C13 C12 H12 121.4 . . ?
C12 C13 Cl2 118.24(15) . . ?
C14 C13 Cl2 119.30(15) . . ?
C14 C13 C12 122.45(17) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.54(18) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.59(17) . . ?
C14 C15 H15 119.2 . . ?
H21A N21 H21B 119(2) . . ?
C21 N21 H21A 119.2(15) . . ?
C21 N21 H21B 121.9(16) . . ?
O21 C21 N21 121.79(17) . . ?
O21 C21 C22 119.82(15) . . ?
N21 C21 C22 118.38(16) . . ?
C23 C22 C21 118.55(16) . . ?
C23 C22 C27 119.71(17) . . ?
C27 C22 C21 121.73(16) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.93(18) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.77(19) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.41(19) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.39(19) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 H27 120.1 . . ?
C26 C27 C22 119.78(19) . . ?
C26 C27 H27 120.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.477
_oxdiff_exptl_absorpt_empirical_full_min 0.412
####################################################################### 
# 
# 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_LON-ISO
_database_code_depnum_ccdc_archive 'CCDC 1531957'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.07.25 svn.r3318 for OlexSys, GUI svn.r5204)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl2 N2 O2, C6 H6 N2 O'
_chemical_formula_sum            'C21 H16 Cl2 N4 O3'
_chemical_formula_weight         443.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.9910(3)
_cell_length_b                   7.6724(2)
_cell_length_c                   19.8344(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.409(2)
_cell_angle_gamma                90
_cell_volume                     1960.43(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9310
_cell_measurement_theta_min      3.1560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.4588
_exptl_crystal_size_mid          0.3589
_exptl_crystal_size_min          0.1876
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34896
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.090
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1003  178.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00   14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597  -57.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega  -90.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597  -77.0000  120.0000 109

#__ type_ start__ end____ width___ exp.time_
  4 omega  -42.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597   57.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1003  -99.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1003 -178.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1003 -178.0000    0.0000 66

#__ type_ start__ end____ width___ exp.time_
  8 omega -101.00  -55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597  178.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
  9 omega  -88.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597  -38.0000  -30.0000 99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0022889000
_diffrn_orient_matrix_UB_12      -0.0780454000
_diffrn_orient_matrix_UB_13      -0.0189110000
_diffrn_orient_matrix_UB_21      0.0548618000
_diffrn_orient_matrix_UB_22      -0.0005764000
_diffrn_orient_matrix_UB_23      0.0077565000
_diffrn_orient_matrix_UB_31      -0.0042855000
_diffrn_orient_matrix_UB_32      -0.0495023000
_diffrn_orient_matrix_UB_33      0.0297053000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3998
_reflns_number_total             4486
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+1.7336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C23(H23),
 C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_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 0.63242(4) 0.17503(6) 0.43147(2) 0.02668(12) Uani 1 1 d . . . . .
Cl2 Cl 0.64935(4) 0.81509(6) 0.53685(2) 0.02774(12) Uani 1 1 d . . . . .
O1 O 0.51772(10) 0.66088(16) 0.10370(6) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.62912(10) 0.47334(17) 0.06526(6) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.627(2) 0.545(4) 0.0298(14) 0.059(8) Uiso 1 1 d . . . . .
N1 N 0.52120(11) 0.31032(18) 0.26015(7) 0.0166(3) Uani 1 1 d . . . . .
N2 N 0.51482(11) 0.44859(18) 0.21790(7) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.56916(13) 0.5275(2) 0.10969(8) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.56838(12) 0.4055(2) 0.16741(8) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.61082(12) 0.2346(2) 0.17637(8) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.67070(13) 0.1234(2) 0.14034(9) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.6951 0.1608 0.0996 0.024 Uiso 1 1 calc R . . . .
C5 C 0.69270(14) -0.0409(2) 0.16600(9) 0.0246(4) Uani 1 1 d . . . . .
H5 H 0.7330 -0.1177 0.1424 0.030 Uiso 1 1 calc R . . . .
C6 C 0.65697(15) -0.0986(2) 0.22654(9) 0.0241(4) Uani 1 1 d . . . . .
H6 H 0.6729 -0.2137 0.2423 0.029 Uiso 1 1 calc R . . . .
C7 C 0.59959(14) 0.0080(2) 0.26324(9) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.5761 -0.0301 0.3042 0.024 Uiso 1 1 calc R . . . .
C8 C 0.57744(12) 0.1760(2) 0.23718(8) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.46449(13) 0.3146(2) 0.31914(8) 0.0177(3) Uani 1 1 d . . . . .
H9A H 0.4634 0.1960 0.3387 0.021 Uiso 1 1 calc R . . . .
H9B H 0.3918 0.3497 0.3042 0.021 Uiso 1 1 calc R . . . .
C10 C 0.51190(12) 0.4392(2) 0.37356(8) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.58775(13) 0.3883(2) 0.42582(8) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.63038(13) 0.5024(2) 0.47613(8) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.6818 0.4644 0.5115 0.024 Uiso 1 1 calc R . . . .
C13 C 0.59586(13) 0.6727(2) 0.47332(8) 0.0203(4) Uani 1 1 d . . . . .
C14 C 0.52004(15) 0.7301(2) 0.42260(9) 0.0230(4) Uani 1 1 d . . . . .
H14 H 0.4967 0.8475 0.4216 0.028 Uiso 1 1 calc R . . . .
C15 C 0.47910(14) 0.6126(2) 0.37336(8) 0.0211(4) Uani 1 1 d . . . . .
H15 H 0.4272 0.6511 0.3384 0.025 Uiso 1 1 calc R . . . .
O21 O 0.76440(10) 0.51752(16) 0.73398(6) 0.0212(3) Uani 1 1 d . . . . .
N21 N 0.85925(13) 0.7256(2) 0.68988(8) 0.0203(3) Uani 1 1 d . . . . .
H21A H 0.8442(17) 0.796(3) 0.7164(12) 0.026(6) Uiso 1 1 d . . . . .
H21B H 0.9056(17) 0.752(3) 0.6656(11) 0.025(5) Uiso 1 1 d . . . . .
N22 N 0.87015(11) 0.19480(18) 0.53632(7) 0.0173(3) Uani 1 1 d . . . . .
C21 C 0.82071(12) 0.5652(2) 0.69160(8) 0.0158(3) Uani 1 1 d . . . . .
C22 C 0.84317(12) 0.4390(2) 0.63678(8) 0.0141(3) Uani 1 1 d . . . . .
C23 C 0.88611(13) 0.4878(2) 0.57859(8) 0.0173(3) Uani 1 1 d . . . . .
H23 H 0.9070 0.6047 0.5724 0.021 Uiso 1 1 calc R . . . .
C24 C 0.89764(13) 0.3617(2) 0.53004(8) 0.0182(3) Uani 1 1 d . . . . .
H24 H 0.9265 0.3954 0.4904 0.022 Uiso 1 1 calc R . . . .
C25 C 0.83007(13) 0.1488(2) 0.59282(8) 0.0180(3) Uani 1 1 d . . . . .
H25 H 0.8112 0.0305 0.5981 0.022 Uiso 1 1 calc R . . . .
C26 C 0.81494(12) 0.2660(2) 0.64375(8) 0.0165(3) Uani 1 1 d . . . . .
H26 H 0.7857 0.2287 0.6828 0.020 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7350(18) . ?
Cl2 C13 1.7429(18) . ?
O1 C1 1.220(2) . ?
O2 H2 0.89(3) . ?
O2 C1 1.316(2) . ?
N1 N2 1.3478(19) . ?
N1 C8 1.374(2) . ?
N1 C9 1.461(2) . ?
N2 C2 1.333(2) . ?
C1 C2 1.480(2) . ?
C2 C3 1.425(2) . ?
C3 C4 1.410(2) . ?
C3 C8 1.407(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.413(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.404(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.512(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.397(2) . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 C14 1.386(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9500 . ?
O21 C21 1.238(2) . ?
N21 H21A 0.80(2) . ?
N21 H21B 0.84(2) . ?
N21 C21 1.331(2) . ?
N22 C24 1.340(2) . ?
N22 C25 1.342(2) . ?
C21 C22 1.512(2) . ?
C22 C23 1.396(2) . ?
C22 C26 1.388(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.385(2) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 111.8(18) . . ?
N2 N1 C8 112.13(13) . . ?
N2 N1 C9 118.89(13) . . ?
C8 N1 C9 128.81(14) . . ?
C2 N2 N1 106.02(13) . . ?
O1 C1 O2 124.31(15) . . ?
O1 C1 C2 123.21(15) . . ?
O2 C1 C2 112.47(14) . . ?
N2 C2 C1 118.76(14) . . ?
N2 C2 C3 111.45(14) . . ?
C3 C2 C1 129.59(14) . . ?
C4 C3 C2 136.39(15) . . ?
C8 C3 C2 104.13(14) . . ?
C8 C3 C4 119.47(15) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.99(16) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.73(17) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.51(17) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 121.6 . . ?
C6 C7 C8 116.75(16) . . ?
C8 C7 H7 121.6 . . ?
N1 C8 C3 106.27(14) . . ?
N1 C8 C7 131.18(15) . . ?
C7 C8 C3 122.53(15) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
N1 C9 C10 112.63(13) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C11 C10 C9 122.58(15) . . ?
C11 C10 C15 117.14(16) . . ?
C15 C10 C9 120.27(15) . . ?
C10 C11 Cl1 120.80(14) . . ?
C12 C11 Cl1 116.70(13) . . ?
C12 C11 C10 122.50(16) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.08(16) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 Cl2 117.83(14) . . ?
C12 C13 C14 121.78(16) . . ?
C14 C13 Cl2 120.38(14) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.57(17) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 121.93(16) . . ?
C14 C15 H15 119.0 . . ?
H21A N21 H21B 118(2) . . ?
C21 N21 H21A 119.1(16) . . ?
C21 N21 H21B 122.5(15) . . ?
C24 N22 C25 117.75(14) . . ?
O21 C21 N21 123.20(15) . . ?
O21 C21 C22 118.98(15) . . ?
N21 C21 C22 117.75(14) . . ?
C23 C22 C21 123.88(15) . . ?
C26 C22 C21 117.54(14) . . ?
C26 C22 C23 118.51(14) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 C22 118.54(15) . . ?
C24 C23 H23 120.7 . . ?
N22 C24 C23 123.25(15) . . ?
N22 C24 H24 118.4 . . ?
C23 C24 H24 118.4 . . ?
N22 C25 H25 118.5 . . ?
N22 C25 C26 123.02(16) . . ?
C26 C25 H25 118.5 . . ?
C22 C26 H26 120.5 . . ?
C25 C26 C22 118.93(15) . . ?
C25 C26 H26 120.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9B O21 0.99 2.31 3.287(2) 169.2 3_666
C23 H23 O1 0.95 2.34 3.197(2) 150.3 4_676
C25 H25 Cl2 0.95 2.82 3.5537(17) 134.4 1_545
C26 H26 O21 0.95 2.46 3.350(2) 156.1 2_646

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 C11 C12 C13 -179.53(12) . . . . ?
Cl2 C13 C14 C15 -179.59(13) . . . . ?
O1 C1 C2 N2 -4.9(2) . . . . ?
O1 C1 C2 C3 169.42(16) . . . . ?
O2 C1 C2 N2 176.72(14) . . . . ?
O2 C1 C2 C3 -9.0(2) . . . . ?
N1 N2 C2 C1 175.51(14) . . . . ?
N1 N2 C2 C3 0.21(18) . . . . ?
N1 C9 C10 C11 -90.09(18) . . . . ?
N1 C9 C10 C15 90.74(18) . . . . ?
N2 N1 C8 C3 1.08(18) . . . . ?
N2 N1 C8 C7 -177.06(17) . . . . ?
N2 N1 C9 C10 -71.75(18) . . . . ?
N2 C2 C3 C4 178.96(18) . . . . ?
N2 C2 C3 C8 0.43(18) . . . . ?
C1 C2 C3 C4 4.3(3) . . . . ?
C1 C2 C3 C8 -174.22(16) . . . . ?
C2 C3 C4 C5 -177.29(18) . . . . ?
C2 C3 C8 N1 -0.87(17) . . . . ?
C2 C3 C8 C7 177.47(15) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C3 C8 N1 -179.71(14) . . . . ?
C4 C3 C8 C7 -1.4(2) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 N1 178.36(17) . . . . ?
C6 C7 C8 C3 0.5(3) . . . . ?
C8 N1 N2 C2 -0.81(18) . . . . ?
C8 N1 C9 C10 113.29(18) . . . . ?
C8 C3 C4 C5 1.1(2) . . . . ?
C9 N1 N2 C2 -176.58(14) . . . . ?
C9 N1 C8 C3 176.32(15) . . . . ?
C9 N1 C8 C7 -1.8(3) . . . . ?
C9 C10 C11 Cl1 -0.2(2) . . . . ?
C9 C10 C11 C12 -179.30(15) . . . . ?
C9 C10 C15 C14 179.46(15) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C10 C15 C14 0.3(2) . . . . ?
C11 C12 C13 Cl2 179.75(12) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C15 C10 C11 Cl1 179.00(12) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
O21 C21 C22 C23 165.77(15) . . . . ?
O21 C21 C22 C26 -11.3(2) . . . . ?
N21 C21 C22 C23 -11.3(2) . . . . ?
N21 C21 C22 C26 171.61(15) . . . . ?
N22 C25 C26 C22 -0.6(3) . . . . ?
C21 C22 C23 C24 -176.38(15) . . . . ?
C21 C22 C26 C25 177.04(14) . . . . ?
C22 C23 C24 N22 -0.4(3) . . . . ?
C23 C22 C26 C25 -0.2(2) . . . . ?
C24 N22 C25 C26 0.9(2) . . . . ?
C25 N22 C24 C23 -0.4(2) . . . . ?
C26 C22 C23 C24 0.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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
18 1 3 0.0741 17.9798 0.9906 3.0745 -0.0943 1.0097 -0.0348
-17 0 -6 0.0841 -16.9756 0.0090 -6.0744 0.0753 -0.9784 -0.1081
-11 3 -18 0.1103 -10.9620 3.0060 -18.0648 0.0819 -0.7432 -0.6384
-3 -6 24 0.2014 -3.0359 -5.9989 24.0171 0.0071 0.0232 1.0234
4 6 -23 0.2111 4.0335 5.9984 -23.0121 -0.0237 0.0393 -0.9978
6 1 -27 0.1777 6.0324 0.9960 -27.0025 0.4467 0.1209 -0.8773
-6 4 25 0.1429 -6.0248 4.0052 24.9953 -0.7991 -0.1390 0.5700
-2 11 -5 0.2061 -1.9807 11.0036 -5.0245 -0.7683 -0.1540 -0.6855
4 -10 -5 0.1412 3.9935 -10.0048 -4.9780 0.8841 0.1862 0.3303

_olex2_exptl_crystal_mounting_method 'MiTeGen Micromesh'
_olex2_submission_original_sample_id L2-89-A
_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_LON-MEL
_database_code_depnum_ccdc_archive 'CCDC 1531958'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Cl2 N2 O2, C3 H7 N6'
_chemical_formula_sum            'C18 H16 Cl2 N8 O2'
_chemical_formula_weight         447.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H16 N8 O2 Cl2'
_chemical_oxdiff_usercomment     L3-03-B
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.0752(4)
_cell_length_b                   8.1750(4)
_cell_length_c                   16.8057(10)
_cell_angle_alpha                99.416(5)
_cell_angle_beta                 100.168(5)
_cell_angle_gamma                94.778(5)
_cell_volume                     937.57(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8211
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.6960
_cell_measurement_theta_min      3.2140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             460
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.1208
_exptl_crystal_size_min          0.057
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.542
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -32.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548  -90.0000   24.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   17.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.8236  -90.0000   24.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega  -62.00   12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.8236   90.0000  139.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega  -60.00   56.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548  -77.0000  -90.0000 116

#__ type_ start__ end____ width___ exp.time_
  5 omega  -55.00   52.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548  -57.0000  120.0000 107

#__ type_ start__ end____ width___ exp.time_
  6 omega  -13.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548   77.0000    0.0000 109

#__ type_ start__ end____ width___ exp.time_
  7 omega  -10.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548   57.0000 -120.0000 107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.1022975000
_diffrn_orient_matrix_UB_12      -0.0122362000
_diffrn_orient_matrix_UB_13      -0.0058627000
_diffrn_orient_matrix_UB_21      -0.0042312000
_diffrn_orient_matrix_UB_22      -0.0484724000
_diffrn_orient_matrix_UB_23      -0.0394790000
_diffrn_orient_matrix_UB_31      0.0055844000
_diffrn_orient_matrix_UB_32      -0.0730777000
_diffrn_orient_matrix_UB_33      0.0175642000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3862
_reflns_number_total             4299
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.041
_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)+(0.0380P)²+0.7048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0921
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.32270(5) 0.14092(5) 0.16571(3) 0.02026(11) Uani 1 1 d . . . . .
Cl2 Cl 0.70311(7) 0.34403(6) -0.05727(3) 0.02687(12) Uani 1 1 d . . . . .
O1 O 1.28997(16) 0.29447(13) 0.38339(7) 0.0167(2) Uani 1 1 d . . . . .
O2 O 1.46877(15) 0.08435(13) 0.39258(7) 0.0159(2) Uani 1 1 d . . . . .
N1 N 0.85758(18) -0.07155(16) 0.25598(8) 0.0133(3) Uani 1 1 d . . . . .
N2 N 0.97286(18) 0.06523(16) 0.30154(8) 0.0128(3) Uani 1 1 d . . . . .
C1 C 1.3134(2) 0.14193(18) 0.37016(9) 0.0119(3) Uani 1 1 d . . . . .
C2 C 1.1477(2) 0.01894(18) 0.32148(9) 0.0113(3) Uani 1 1 d . . . . .
C3 C 1.1497(2) -0.15295(18) 0.28671(9) 0.0122(3) Uani 1 1 d . . . . .
C4 C 1.2882(2) -0.26672(19) 0.28581(9) 0.0142(3) Uani 1 1 d . . . . .
H4 H 1.4179 -0.2340 0.3140 0.017 Uiso 1 1 calc R . . . .
C5 C 1.2308(2) -0.4267(2) 0.24300(10) 0.0175(3) Uani 1 1 d . . . . .
H5 H 1.3226 -0.5050 0.2418 0.021 Uiso 1 1 calc R . . . .
C6 C 1.0385(3) -0.4770(2) 0.20077(10) 0.0194(3) Uani 1 1 d . . . . .
H6 H 1.0042 -0.5886 0.1720 0.023 Uiso 1 1 calc R . . . .
C7 C 0.8995(2) -0.36909(19) 0.20006(10) 0.0173(3) Uani 1 1 d . . . . .
H7 H 0.7703 -0.4029 0.1714 0.021 Uiso 1 1 calc R . . . .
C8 C 0.9589(2) -0.20593(19) 0.24408(9) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.6653(2) -0.0508(2) 0.21512(10) 0.0145(3) Uani 1 1 d . . . . .
H9A H 0.5974 0.0093 0.2556 0.017 Uiso 1 1 calc R . . . .
H9B H 0.5913 -0.1620 0.1929 0.017 Uiso 1 1 calc R . . . .
C10 C 0.6714(2) 0.04577(19) 0.14554(9) 0.0136(3) Uani 1 1 d . . . . .
C11 C 0.5236(2) 0.1385(2) 0.11947(10) 0.0152(3) Uani 1 1 d . . . . .
C12 C 0.5290(2) 0.2307(2) 0.05732(10) 0.0179(3) Uani 1 1 d . . . . .
H12 H 0.4261 0.2929 0.0407 0.021 Uiso 1 1 calc R . . . .
C13 C 0.6892(2) 0.2292(2) 0.02039(10) 0.0179(3) Uani 1 1 d . . . . .
C14 C 0.8387(2) 0.1382(2) 0.04368(10) 0.0180(3) Uani 1 1 d . . . . .
H14 H 0.9474 0.1382 0.0176 0.022 Uiso 1 1 calc R . . . .
C15 C 0.8283(2) 0.0468(2) 0.10566(10) 0.0160(3) Uani 1 1 d . . . . .
H15 H 0.9306 -0.0167 0.1214 0.019 Uiso 1 1 calc R . . . .
N21 N 1.02453(19) 0.50218(16) 0.39938(8) 0.0120(3) Uani 1 1 d . . . . .
H21 H 1.083(3) 0.423(3) 0.3866(15) 0.038(7) Uiso 1 1 d . . . . .
N22 N 0.73187(18) 0.62120(16) 0.39494(8) 0.0134(3) Uani 1 1 d . . . . .
N23 N 1.03545(18) 0.77765(15) 0.46834(8) 0.0118(3) Uani 1 1 d . . . . .
N24 N 0.7350(2) 0.34795(17) 0.33553(9) 0.0166(3) Uani 1 1 d . . . . .
H24A H 0.798(3) 0.269(3) 0.3307(13) 0.026(6) Uiso 1 1 d . . . . .
H24B H 0.611(3) 0.337(2) 0.3332(12) 0.019(5) Uiso 1 1 d . . . . .
N25 N 0.7550(2) 0.89713(17) 0.45313(9) 0.0146(3) Uani 1 1 d . . . . .
H25A H 0.820(3) 0.987(3) 0.4770(13) 0.023(5) Uiso 1 1 d . . . . .
H25B H 0.637(3) 0.892(2) 0.4321(12) 0.017(5) Uiso 1 1 d . . . . .
N26 N 1.31297(19) 0.64931(18) 0.47106(9) 0.0142(3) Uani 1 1 d . . . . .
H26A H 1.362(3) 0.572(3) 0.4538(13) 0.022(5) Uiso 1 1 d . . . . .
H26B H 1.374(3) 0.729(3) 0.5064(14) 0.023(5) Uiso 1 1 d . . . . .
C21 C 0.8283(2) 0.49282(18) 0.37709(9) 0.0126(3) Uani 1 1 d . . . . .
C22 C 0.8421(2) 0.76218(18) 0.43836(9) 0.0118(3) Uani 1 1 d . . . . .
C23 C 1.1242(2) 0.64565(18) 0.44680(9) 0.0111(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7360(16) . ?
Cl2 C13 1.7391(16) . ?
O1 C1 1.2604(18) . ?
O2 C1 1.2529(18) . ?
N1 N2 1.3599(17) . ?
N1 C8 1.368(2) . ?
N1 C9 1.4487(19) . ?
N2 C2 1.3261(19) . ?
C1 C2 1.500(2) . ?
C2 C3 1.433(2) . ?
C3 C4 1.406(2) . ?
C3 C8 1.408(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.412(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.374(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.406(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.519(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.394(2) . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 C14 1.381(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
N21 H21 0.82(3) . ?
N21 C21 1.365(2) . ?
N21 C23 1.3661(19) . ?
N22 C21 1.321(2) . ?
N22 C22 1.3576(19) . ?
N23 C22 1.3596(19) . ?
N23 C23 1.3250(19) . ?
N24 H24A 0.82(2) . ?
N24 H24B 0.87(2) . ?
N24 C21 1.328(2) . ?
N25 H25A 0.83(2) . ?
N25 H25B 0.84(2) . ?
N25 C22 1.317(2) . ?
N26 H26A 0.78(2) . ?
N26 H26B 0.83(2) . ?
N26 C23 1.322(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 111.54(12) . . ?
N2 N1 C9 118.61(12) . . ?
C8 N1 C9 128.67(13) . . ?
C2 N2 N1 106.87(12) . . ?
O1 C1 C2 118.68(13) . . ?
O2 C1 O1 124.66(14) . . ?
O2 C1 C2 116.61(13) . . ?
N2 C2 C1 121.01(13) . . ?
N2 C2 C3 110.53(13) . . ?
C3 C2 C1 128.38(13) . . ?
C4 C3 C2 136.19(14) . . ?
C4 C3 C8 119.27(14) . . ?
C8 C3 C2 104.54(13) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.21(14) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.51(15) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.88(15) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 121.8 . . ?
C6 C7 C8 116.36(15) . . ?
C8 C7 H7 121.8 . . ?
N1 C8 C3 106.48(13) . . ?
N1 C8 C7 130.75(15) . . ?
C7 C8 C3 122.77(15) . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
N1 C9 C10 111.65(12) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C11 C10 C9 121.97(14) . . ?
C11 C10 C15 117.11(14) . . ?
C15 C10 C9 120.92(14) . . ?
C10 C11 Cl1 119.53(12) . . ?
C12 C11 Cl1 117.74(12) . . ?
C12 C11 C10 122.74(15) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.87(15) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 Cl2 119.49(13) . . ?
C14 C13 Cl2 119.01(13) . . ?
C14 C13 C12 121.50(15) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.17(15) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.61(15) . . ?
C14 C15 H15 119.2 . . ?
C21 N21 H21 121.7(17) . . ?
C21 N21 C23 118.99(13) . . ?
C23 N21 H21 119.2(17) . . ?
C21 N22 C22 115.02(13) . . ?
C23 N23 C22 115.83(13) . . ?
H24A N24 H24B 123(2) . . ?
C21 N24 H24A 117.1(15) . . ?
C21 N24 H24B 115.4(13) . . ?
H25A N25 H25B 122(2) . . ?
C22 N25 H25A 119.6(14) . . ?
C22 N25 H25B 117.6(14) . . ?
H26A N26 H26B 123(2) . . ?
C23 N26 H26A 117.5(16) . . ?
C23 N26 H26B 119.6(15) . . ?
N22 C21 N21 122.47(14) . . ?
N22 C21 N24 120.22(14) . . ?
N24 C21 N21 117.31(14) . . ?
N22 C22 N23 126.00(14) . . ?
N25 C22 N22 117.53(14) . . ?
N25 C22 N23 116.47(14) . . ?
N23 C23 N21 121.36(14) . . ?
N26 C23 N21 118.05(14) . . ?
N26 C23 N23 120.59(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 O1 0.82(3) 1.87(3) 2.6539(17) 159(2) .
N24 H24A N2 0.82(2) 2.20(2) 3.009(2) 172(2) .
N24 H24B O1 0.87(2) 2.58(2) 3.3959(19) 158.2(17) 1_455
N25 H25A N23 0.83(2) 2.09(2) 2.9176(19) 175(2) 2_776
N25 H25B O2 0.84(2) 2.17(2) 2.7890(17) 130.1(17) 1_465
N26 H26A O1 0.78(2) 2.35(2) 3.0083(18) 142(2) .
N26 H26B O2 0.83(2) 2.16(2) 2.9892(19) 174(2) 2_866

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 C11 C12 C13 179.90(12) . . . . ?
Cl2 C13 C14 C15 179.88(12) . . . . ?
O1 C1 C2 N2 -8.5(2) . . . . ?
O1 C1 C2 C3 167.87(15) . . . . ?
O2 C1 C2 N2 173.72(14) . . . . ?
O2 C1 C2 C3 -9.9(2) . . . . ?
N1 N2 C2 C1 178.20(13) . . . . ?
N1 N2 C2 C3 1.21(16) . . . . ?
N1 C9 C10 C11 -153.59(14) . . . . ?
N1 C9 C10 C15 25.5(2) . . . . ?
N2 N1 C8 C3 1.75(17) . . . . ?
N2 N1 C8 C7 -178.59(15) . . . . ?
N2 N1 C9 C10 68.86(17) . . . . ?
N2 C2 C3 C4 179.11(16) . . . . ?
N2 C2 C3 C8 -0.18(17) . . . . ?
C1 C2 C3 C4 2.4(3) . . . . ?
C1 C2 C3 C8 -176.88(14) . . . . ?
C2 C3 C4 C5 -179.32(17) . . . . ?
C2 C3 C8 N1 -0.93(16) . . . . ?
C2 C3 C8 C7 179.38(14) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C3 C8 N1 179.64(13) . . . . ?
C4 C3 C8 C7 -0.1(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 N1 -179.33(15) . . . . ?
C6 C7 C8 C3 0.3(2) . . . . ?
C8 N1 N2 C2 -1.87(16) . . . . ?
C8 N1 C9 C10 -97.67(17) . . . . ?
C8 C3 C4 C5 -0.1(2) . . . . ?
C9 N1 N2 C2 -170.59(13) . . . . ?
C9 N1 C8 C3 169.05(14) . . . . ?
C9 N1 C8 C7 -11.3(3) . . . . ?
C9 C10 C11 Cl1 -1.5(2) . . . . ?
C9 C10 C11 C12 178.41(14) . . . . ?
C9 C10 C15 C14 -178.10(14) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C11 C10 C15 C14 1.1(2) . . . . ?
C11 C12 C13 Cl2 -179.57(12) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C10 -0.6(2) . . . . ?
C15 C10 C11 Cl1 179.31(12) . . . . ?
C15 C10 C11 C12 -0.7(2) . . . . ?
C21 N21 C23 N23 -3.0(2) . . . . ?
C21 N21 C23 N26 176.76(13) . . . . ?
C21 N22 C22 N23 -4.4(2) . . . . ?
C21 N22 C22 N25 175.62(14) . . . . ?
C22 N22 C21 N21 -1.1(2) . . . . ?
C22 N22 C21 N24 179.31(14) . . . . ?
C22 N23 C23 N21 -1.9(2) . . . . ?
C22 N23 C23 N26 178.36(13) . . . . ?
C23 N21 C21 N22 4.7(2) . . . . ?
C23 N21 C21 N24 -175.76(13) . . . . ?
C23 N23 C22 N22 5.9(2) . . . . ?
C23 N23 C22 N25 -174.13(13) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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
3 0 -23 0.0749 3.0089 0.0642 -22.9140 -0.1743 0.8888 -0.3904
-9 -1 -2 0.0361 -8.9335 -1.0976 -2.0816 0.9395 0.1732 -0.0062
9 1 2 0.0209 8.9335 1.0976 2.0816 -0.9395 -0.1732 0.0062
-2 11 -1 0.5232 -2.0894 10.9302 -0.8909 0.0852 -0.4858 -0.8261
2 -11 0 0.5393 2.0906 -10.9289 -0.1064 -0.0795 0.5251 0.8085
-3 0 23 0.0459 -3.0089 -0.0642 22.9140 0.1743 -0.8888 0.3904

_olex2_date_sample_data_collection 2015-07-13
_olex2_exptl_crystal_mounting_method 'MiTeGen micromesh'
_olex2_submission_original_sample_id L3-03-B
_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_LON-4DMAP_2-1
_database_code_depnum_ccdc_archive 'CCDC 1531959'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C15 H10 Cl2 N2 O2, C15 H9 Cl2 N2 O2, C7 H11 N2'
_chemical_formula_sum            'C37 H30 Cl4 N6 O4'
_chemical_formula_weight         764.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H20 O4 N4 Cl2'
_chemical_oxdiff_usercomment     L3-21-C2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5711(2)
_cell_length_b                   12.3681(4)
_cell_length_c                   16.6270(5)
_cell_angle_alpha                79.963(3)
_cell_angle_beta                 81.329(2)
_cell_angle_gamma                84.947(3)
_cell_volume                     1712.33(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8486
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5060
_cell_measurement_theta_min      2.8360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             788
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 14 17 0.0138
1 10 -16 0.0570
1 -14 -16 0.0172
-1 -11 16 0.0304
-12 -4 -5 0.1215
6 11 -10 0.0875
8 -5 16 0.0727

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.053
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
1.0019 14.0365 16.9960 -0.8601 -0.4561 0.2406
0.9955 9.9749 -16.0224 -0.4501 0.8814 -0.0295
0.9995 -14.0321 -15.9952 0.8862 0.4623 -0.0752
-0.9953 -10.9752 16.0235 0.5058 -0.8989 0.0276
-12.0076 -4.0260 -4.9999 0.0605 -0.1499 -0.9918
5.9996 10.9927 -10.0190 -0.4604 0.7652 0.4137
8.0091 -4.9617 16.0175 0.3146 -0.5741 0.7473

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24011
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         2.512
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  97.00   0.50   40.00    --   15.17  77.00 120.00  234
  2  ω    -20.00  97.00   0.50   40.00    --   15.17  77.00-150.00  234
  3  ω    -20.00  97.00   0.50   40.00    --   15.17  77.00   0.00  234
  4  ω    -51.00  66.00   0.50   40.00    --  -15.79  77.00-120.00  234
  5  ω    -61.00  43.00   0.50   40.00    --   15.17 -57.00  90.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  SuperNova
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0159428000
_diffrn_orient_matrix_UB_12      -0.0556658000
_diffrn_orient_matrix_UB_13      -0.0055725000
_diffrn_orient_matrix_UB_21      0.0244085000
_diffrn_orient_matrix_UB_22      0.0174154000
_diffrn_orient_matrix_UB_23      -0.0426548000
_diffrn_orient_matrix_UB_31      0.0786512000
_diffrn_orient_matrix_UB_32      0.0019275000
_diffrn_orient_matrix_UB_33      0.0079266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6467
_reflns_number_total             7913
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.923
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         7913
_refine_ls_number_restraints     1010
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+1.3674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1056
_refine_special_details          
;
4-Dimethylaminopyridine is positioned on the inversion centre therefore has 2 positions, each being half occupied.
2:1 ratio with deprotonation of a single carboxylic acid group for charge balance
One moeity of lonidamine has disorder of Cl atom over two sites in 87:13 ratio
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl24)=Sof(H32)=1-FVAR(1)
 Sof(Cl23)=Sof(H36)=FVAR(1)
 Fixed Sof: N41(0.5) H41(0.5) N42(0.5) C41(0.5) H41A(0.5) C42(0.5) H42(0.5)
 C43(0.5) C44(0.5) H44(0.5) C45(0.5) H45(0.5) C46(0.5) H46A(0.5) H46B(0.5)
 H46C(0.5) C47(0.5) H47A(0.5) H47B(0.5) H47C(0.5) N41A(0.5) H41B(0.5) N42A(0.5)
 C41A(0.5) H41C(0.5) C42A(0.5) H42A(0.5) C43A(0.5) C44A(0.5) H44A(0.5)
 C45A(0.5) H45A(0.5) C46A(0.5) H46D(0.5) H46E(0.5) H46F(0.5) C47A(0.5)
 H47D(0.5) H47E(0.5) H47F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C30(H30A,H30B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C24(H24),
 C25(H25), C26(H26), C27(H27), C32(H32), C33(H33), C35(H35), C36(H36),
 C41(H41A), C42(H42), C44(H44), C45(H45), C41A(H41C), C42A(H42A), C44A(H44A),
 C45A(H45A)
6.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C46A(H46D,H46E,H46F), C47A(H47D,
 H47E,H47F)
;
_atom_sites_solution_hydrogens   mixed
_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 2.50399(6) 0.24368(5) 0.57902(3) 0.03058(14) Uani 1 1 d . U . . .
Cl2 Cl 2.38199(6) 0.05784(5) 0.32838(3) 0.02692(13) Uani 1 1 d . U . . .
O1 O 1.65684(16) 0.22700(11) 0.75959(9) 0.0217(3) Uani 1 1 d . U . . .
H1 H 1.537(5) 0.255(3) 0.773(2) 0.097(13) Uiso 1 1 d . . . . .
O2 O 1.57689(17) 0.06390(12) 0.82679(10) 0.0280(4) Uani 1 1 d . U . . .
N1 N 2.09416(18) 0.07329(13) 0.72961(10) 0.0182(3) Uani 1 1 d . U . . .
N2 N 1.95956(18) 0.13939(13) 0.73124(10) 0.0177(3) Uani 1 1 d . U . . .
C1 C 1.6798(2) 0.12374(16) 0.78914(12) 0.0171(4) Uani 1 1 d . U . . .
C2 C 1.8460(2) 0.07812(15) 0.77413(11) 0.0154(4) Uani 1 1 d . U . . .
C3 C 1.9061(2) -0.03154(15) 0.80099(11) 0.0157(4) Uani 1 1 d . U . . .
C4 C 1.8441(2) -0.12943(16) 0.84576(12) 0.0187(4) Uani 1 1 d . U . . .
H4 H 1.7357 -0.1316 0.8685 0.022 Uiso 1 1 calc R . . . .
C5 C 1.9453(2) -0.22159(17) 0.85554(13) 0.0232(4) Uani 1 1 d . U . . .
H5 H 1.9052 -0.2885 0.8852 0.028 Uiso 1 1 calc R . . . .
C6 C 2.1072(2) -0.22013(17) 0.82285(13) 0.0234(4) Uani 1 1 d . U . . .
H6 H 2.1729 -0.2860 0.8308 0.028 Uiso 1 1 calc R . . . .
C7 C 2.1721(2) -0.12558(17) 0.77978(13) 0.0215(4) Uani 1 1 d . U . . .
H7 H 2.2810 -0.1241 0.7580 0.026 Uiso 1 1 calc R . . . .
C8 C 2.0684(2) -0.03138(16) 0.76988(12) 0.0169(4) Uani 1 1 d . U . . .
C9 C 2.2411(2) 0.11748(17) 0.68624(12) 0.0204(4) Uani 1 1 d . U . . .
H9A H 2.3296 0.0818 0.7152 0.024 Uiso 1 1 calc R . . . .
H9B H 2.2367 0.1972 0.6882 0.024 Uiso 1 1 calc R . . . .
C10 C 2.2743(2) 0.10075(16) 0.59696(12) 0.0180(4) Uani 1 1 d . U . . .
C11 C 2.3929(2) 0.15624(16) 0.54280(12) 0.0197(4) Uani 1 1 d . U . . .
C12 C 2.4279(2) 0.14407(17) 0.46056(12) 0.0203(4) Uani 1 1 d . U . . .
H12 H 2.5086 0.1836 0.4250 0.024 Uiso 1 1 calc R . . . .
C13 C 2.3423(2) 0.07279(17) 0.43158(12) 0.0198(4) Uani 1 1 d . U . . .
C14 C 2.2249(2) 0.01463(16) 0.48301(13) 0.0212(4) Uani 1 1 d . U . . .
H14 H 2.1679 -0.0349 0.4627 0.025 Uiso 1 1 calc R . . . .
C15 C 2.1916(2) 0.02967(16) 0.56478(13) 0.0197(4) Uani 1 1 d . U . . .
H15 H 2.1101 -0.0096 0.5999 0.024 Uiso 1 1 calc R . . . .
Cl23 Cl 0.88008(7) 0.40130(5) 0.98647(4) 0.02555(18) Uani 0.8700(18) 1 d . U P
A 1
Cl24 Cl 0.4991(5) 0.6317(4) 0.7607(3) 0.0379(14) Uani 0.1300(18) 1 d . U P A 2
Cl25 Cl 0.47908(7) 0.74641(5) 1.04343(4) 0.03175(14) Uani 1 1 d . U . . .
O21 O 1.37758(16) 0.29958(11) 0.77968(9) 0.0230(3) Uani 1 1 d . U . . .
O22 O 1.47275(18) 0.45150(13) 0.70135(11) 0.0365(4) Uani 1 1 d . U . . .
N21 N 0.94780(18) 0.47426(14) 0.77299(10) 0.0186(3) Uani 1 1 d . U . . .
N22 N 1.07486(18) 0.40433(13) 0.78824(10) 0.0182(3) Uani 1 1 d . U . . .
C21 C 1.3624(2) 0.39733(16) 0.74065(12) 0.0203(4) Uani 1 1 d . U . . .
C22 C 1.1996(2) 0.45047(16) 0.74229(12) 0.0174(4) Uani 1 1 d . U . . .
C23 C 1.1547(2) 0.55334(16) 0.69458(12) 0.0177(4) Uani 1 1 d . U . . .
C24 C 1.2332(3) 0.63264(17) 0.63503(13) 0.0235(4) Uani 1 1 d . U . . .
H24 H 1.3446 0.6256 0.6199 0.028 Uiso 1 1 calc R . . . .
C25 C 1.1444(3) 0.72045(18) 0.59951(14) 0.0300(5) Uani 1 1 d . U . . .
H25 H 1.1952 0.7750 0.5590 0.036 Uiso 1 1 calc R . . . .
C26 C 0.9798(3) 0.73160(19) 0.62172(15) 0.0341(5) Uani 1 1 d . U . . .
H26 H 0.9221 0.7936 0.5957 0.041 Uiso 1 1 calc R . . . .
C27 C 0.8993(3) 0.65547(18) 0.68004(14) 0.0278(5) Uani 1 1 d . U . . .
H27 H 0.7880 0.6638 0.6950 0.033 Uiso 1 1 calc R . . . .
C28 C 0.9895(2) 0.56526(16) 0.71613(12) 0.0193(4) Uani 1 1 d . U . . .
C30 C 0.7887(2) 0.44274(17) 0.81002(13) 0.0212(4) Uani 1 1 d . U . . .
H30A H 0.7955 0.3659 0.8392 0.025 Uiso 1 1 calc R . . . .
H30B H 0.7226 0.4455 0.7656 0.025 Uiso 1 1 calc R . . . .
C31 C 0.7093(2) 0.51613(16) 0.86993(12) 0.0183(4) Uani 1 1 d . U . . .
C32 C 0.7483(2) 0.50680(16) 0.94935(12) 0.0200(4) Uani 1 1 d . U . . .
H32 H 0.8247 0.4509 0.9671 0.024 Uiso 0.1300(18) 1 calc R . P A 2
C33 C 0.6784(2) 0.57716(17) 1.00364(12) 0.0211(4) Uani 1 1 d . U . . .
H33 H 0.7071 0.5701 1.0574 0.025 Uiso 1 1 calc R . . . .
C34 C 0.5666(2) 0.65726(17) 0.97700(13) 0.0213(4) Uani 1 1 d . U . . .
C35 C 0.5202(2) 0.66780(17) 0.89974(13) 0.0220(4) Uani 1 1 d . U . . .
H35 H 0.4414 0.7225 0.8829 0.026 Uiso 1 1 calc R . . . .
C36 C 0.5921(2) 0.59618(17) 0.84735(12) 0.0205(4) Uani 1 1 d . U . . .
H36 H 0.5603 0.6021 0.7944 0.025 Uiso 0.8700(18) 1 calc R . P A 1
N41 N 1.7462(4) 0.4322(3) 0.6019(2) 0.0216(7) Uani 0.5 1 d . U P B -1
H41 H 1.666(6) 0.421(4) 0.634(3) 0.027(13) Uiso 0.5 1 d . . P C -1
N42 N 2.1516(4) 0.5355(3) 0.4538(2) 0.0226(7) Uani 0.5 1 d . U P B -1
C41 C 1.8857(14) 0.3732(12) 0.6115(10) 0.022(2) Uani 0.5 1 d . U P B -1
H41A H 1.8888 0.3098 0.6529 0.026 Uiso 0.5 1 calc R . P B -1
C42 C 2.0205(5) 0.4048(3) 0.5621(2) 0.0204(8) Uani 0.5 1 d . U P B -1
H42 H 2.1169 0.3620 0.5682 0.025 Uiso 0.5 1 calc R . P B -1
C43 C 2.0193(11) 0.5007(15) 0.5017(12) 0.0173(16) Uani 0.5 1 d . U P B -1
C44 C 1.8699(5) 0.5588(3) 0.4933(3) 0.0222(8) Uani 0.5 1 d . U P B -1
H44 H 1.8617 0.6223 0.4525 0.027 Uiso 0.5 1 calc R . P B -1
C45 C 1.7393(10) 0.5223(10) 0.5443(7) 0.0261(18) Uani 0.5 1 d . U P B -1
H45 H 1.6402 0.5617 0.5390 0.031 Uiso 0.5 1 calc R . P B -1
C46 C 2.3025(9) 0.4755(10) 0.4652(7) 0.0268(19) Uani 0.5 1 d . U P B -1
H46A H 2.3860 0.5093 0.4240 0.040 Uiso 0.5 1 calc GR . P B -1
H46B H 2.2968 0.3988 0.4586 0.040 Uiso 0.5 1 calc GR . P B -1
H46C H 2.3265 0.4779 0.5206 0.040 Uiso 0.5 1 calc GR . P B -1
C47 C 2.1484(13) 0.6357(12) 0.3940(9) 0.023(2) Uani 0.5 1 d . U P B -1
H47A H 2.1237 0.6991 0.4228 0.035 Uiso 0.5 1 calc GR . P B -1
H47B H 2.0674 0.6331 0.3587 0.035 Uiso 0.5 1 calc GR . P B -1
H47C H 2.2520 0.6426 0.3600 0.035 Uiso 0.5 1 calc GR . P B -1
N41A N 0.7391(5) -0.0913(3) 1.0971(2) 0.0258(8) Uani 0.5 1 d . U P D -1
H41B H 0.658(7) -0.116(4) 1.126(3) 0.040(15) Uiso 0.5 1 d . . P E -1
N42A N 1.1291(4) 0.0503(3) 0.9599(2) 0.0216(7) Uani 0.5 1 d . U P D -1
C41A C 0.875(2) -0.1492(12) 1.0955(11) 0.024(2) Uani 0.5 1 d . U P D -1
H41C H 0.8809 -0.2214 1.1263 0.029 Uiso 0.5 1 calc R . P D -1
C42A C 1.0111(5) -0.1055(3) 1.0491(2) 0.0216(8) Uani 0.5 1 d . U P D -1
H42A H 1.1105 -0.1454 1.0523 0.026 Uiso 0.5 1 calc R . P D -1
C43A C 1.002(9) -0.002(6) 0.997(7) 0.017(4) Uani 0.5 1 d . U P D -1
C44A C 0.8514(5) 0.0603(4) 1.0093(2) 0.0218(8) Uani 0.5 1 d . U P D -1
H44A H 0.8407 0.1358 0.9856 0.026 Uiso 0.5 1 calc R . P D -1
C45A C 0.7209(19) 0.0066(14) 1.0567(10) 0.027(2) Uani 0.5 1 d . U P D -1
H45A H 0.6185 0.0431 1.0588 0.032 Uiso 0.5 1 calc R . P D -1
C46A C 1.2818(19) -0.0121(14) 0.9606(10) 0.031(3) Uani 0.5 1 d . U P D -1
H46D H 1.2758 -0.0819 0.9413 0.047 Uiso 0.5 1 calc GR . P D -1
H46E H 1.3087 -0.0269 1.0169 0.047 Uiso 0.5 1 calc GR . P D -1
H46F H 1.3633 0.0306 0.9242 0.047 Uiso 0.5 1 calc GR . P D -1
C47A C 1.116(2) 0.1643(12) 0.9174(11) 0.026(2) Uani 0.5 1 d . U P D -1
H47D H 1.1012 0.2143 0.9580 0.038 Uiso 0.5 1 calc GR . P D -1
H47E H 1.0245 0.1745 0.8870 0.038 Uiso 0.5 1 calc GR . P D -1
H47F H 1.2122 0.1803 0.8788 0.038 Uiso 0.5 1 calc GR . P D -1


_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 C11 1.738(2) . ?
Cl2 C13 1.737(2) . ?
O1 H1 1.06(4) . ?
O1 C1 1.295(2) . ?
O2 C1 1.227(2) . ?
N1 N2 1.354(2) . ?
N1 C8 1.370(2) . ?
N1 C9 1.454(2) . ?
N2 C2 1.328(2) . ?
C1 C2 1.486(3) . ?
C2 C3 1.428(3) . ?
C3 C4 1.408(3) . ?
C3 C8 1.409(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.413(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.403(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.515(3) . ?
C10 C11 1.396(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
Cl23 C32 1.741(2) . ?
Cl24 C36 1.722(5) . ?
Cl25 C34 1.740(2) . ?
O21 C21 1.274(2) . ?
O22 C21 1.242(2) . ?
N21 N22 1.356(2) . ?
N21 C28 1.373(2) . ?
N21 C30 1.466(2) . ?
N22 C22 1.327(2) . ?
C21 C22 1.488(3) . ?
C22 C23 1.432(3) . ?
C23 C24 1.404(3) . ?
C23 C28 1.409(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.369(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.405(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.399(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.510(3) . ?
C31 C32 1.393(3) . ?
C31 C36 1.392(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.396(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.380(3) . ?
C34 C35 1.383(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.391(3) . ?
C36 H36 0.9500 . ?
N41 H41 0.82(5) . ?
N41 C41 1.361(13) . ?
N41 C45 1.339(11) . ?
N42 C43 1.341(12) . ?
N42 C46 1.454(8) . ?
N42 C47 1.449(13) . ?
C41 H41A 0.9500 . ?
C41 C42 1.358(13) . ?
C42 H42 0.9500 . ?
C42 C43 1.415(17) . ?
C43 C44 1.425(12) . ?
C44 H44 0.9500 . ?
C44 C45 1.358(11) . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
N41A H41B 0.83(6) . ?
N41A C41A 1.313(17) . ?
N41A C45A 1.287(16) . ?
N42A C43A 1.33(7) . ?
N42A C46A 1.460(16) . ?
N42A C47A 1.466(15) . ?
C41A H41C 0.9500 . ?
C41A C42A 1.393(18) . ?
C42A H42A 0.9500 . ?
C42A C43A 1.41(7) . ?
C43A C44A 1.45(6) . ?
C44A H44A 0.9500 . ?
C44A C45A 1.413(16) . ?
C45A H45A 0.9500 . ?
C46A H46D 0.9800 . ?
C46A H46E 0.9800 . ?
C46A H46F 0.9800 . ?
C47A H47D 0.9800 . ?
C47A H47E 0.9800 . ?
C47A H47F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 112(2) . . ?
N2 N1 C8 112.12(15) . . ?
N2 N1 C9 119.18(15) . . ?
C8 N1 C9 128.68(16) . . ?
C2 N2 N1 106.14(15) . . ?
O1 C1 C2 115.02(16) . . ?
O2 C1 O1 125.20(18) . . ?
O2 C1 C2 119.78(17) . . ?
N2 C2 C1 121.49(17) . . ?
N2 C2 C3 111.29(16) . . ?
C3 C2 C1 127.22(17) . . ?
C4 C3 C2 136.60(18) . . ?
C4 C3 C8 119.21(18) . . ?
C8 C3 C2 104.18(16) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.90(18) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.04(19) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.58(19) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 121.9 . . ?
C6 C7 C8 116.28(18) . . ?
C8 C7 H7 121.9 . . ?
N1 C8 C3 106.25(16) . . ?
N1 C8 C7 130.75(18) . . ?
C7 C8 C3 122.98(18) . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
N1 C9 C10 113.49(16) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C11 C10 C9 120.45(18) . . ?
C11 C10 C15 116.70(18) . . ?
C15 C10 C9 122.84(17) . . ?
C10 C11 Cl1 119.32(16) . . ?
C12 C11 Cl1 117.90(15) . . ?
C12 C11 C10 122.78(19) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.30(18) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 Cl2 119.10(15) . . ?
C14 C13 Cl2 119.69(16) . . ?
C14 C13 C12 121.21(19) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.03(19) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 121.97(18) . . ?
C14 C15 H15 119.0 . . ?
N22 N21 C28 111.83(15) . . ?
N22 N21 C30 119.76(16) . . ?
C28 N21 C30 128.14(16) . . ?
C22 N22 N21 106.32(15) . . ?
O21 C21 C22 117.28(17) . . ?
O22 C21 O21 125.15(18) . . ?
O22 C21 C22 117.57(18) . . ?
N22 C22 C21 122.66(17) . . ?
N22 C22 C23 111.29(17) . . ?
C23 C22 C21 126.02(17) . . ?
C24 C23 C22 135.68(18) . . ?
C24 C23 C28 120.14(18) . . ?
C28 C23 C22 104.11(17) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 C23 117.96(19) . . ?
C25 C24 H24 121.0 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.4(2) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 118.9 . . ?
C27 C26 C25 122.1(2) . . ?
C27 C26 H26 118.9 . . ?
C26 C27 H27 121.7 . . ?
C26 C27 C28 116.7(2) . . ?
C28 C27 H27 121.7 . . ?
N21 C28 C23 106.44(17) . . ?
N21 C28 C27 131.83(19) . . ?
C27 C28 C23 121.72(19) . . ?
N21 C30 H30A 109.0 . . ?
N21 C30 H30B 109.0 . . ?
N21 C30 C31 112.95(16) . . ?
H30A C30 H30B 107.8 . . ?
C31 C30 H30A 109.0 . . ?
C31 C30 H30B 109.0 . . ?
C32 C31 C30 122.18(18) . . ?
C36 C31 C30 120.53(18) . . ?
C36 C31 C32 117.29(18) . . ?
C31 C32 Cl23 120.65(16) . . ?
C31 C32 H32 119.0 . . ?
C31 C32 C33 122.02(19) . . ?
C33 C32 Cl23 117.25(16) . . ?
C33 C32 H32 119.0 . . ?
C32 C33 H33 120.9 . . ?
C34 C33 C32 118.14(19) . . ?
C34 C33 H33 120.9 . . ?
C33 C34 Cl25 118.88(16) . . ?
C33 C34 C35 122.09(19) . . ?
C35 C34 Cl25 119.02(16) . . ?
C34 C35 H35 120.9 . . ?
C34 C35 C36 118.18(19) . . ?
C36 C35 H35 120.9 . . ?
C31 C36 Cl24 133.6(2) . . ?
C31 C36 H36 118.9 . . ?
C35 C36 Cl24 104.2(2) . . ?
C35 C36 C31 122.21(19) . . ?
C35 C36 H36 118.9 . . ?
C41 N41 H41 123(3) . . ?
C45 N41 H41 116(3) . . ?
C45 N41 C41 120.9(7) . . ?
C43 N42 C46 119.7(8) . . ?
C43 N42 C47 121.1(8) . . ?
C47 N42 C46 119.1(7) . . ?
N41 C41 H41A 120.0 . . ?
C42 C41 N41 120.1(10) . . ?
C42 C41 H41A 120.0 . . ?
C41 C42 H42 119.6 . . ?
C41 C42 C43 120.9(8) . . ?
C43 C42 H42 119.6 . . ?
N42 C43 C42 122.0(9) . . ?
N42 C43 C44 121.2(12) . . ?
C42 C43 C44 116.8(8) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 C43 119.3(8) . . ?
C45 C44 H44 120.3 . . ?
N41 C45 C44 121.9(7) . . ?
N41 C45 H45 119.0 . . ?
C44 C45 H45 119.0 . . ?
N42 C46 H46A 109.5 . . ?
N42 C46 H46B 109.5 . . ?
N42 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N42 C47 H47A 109.5 . . ?
N42 C47 H47B 109.5 . . ?
N42 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C41A N41A H41B 121(4) . . ?
C45A N41A H41B 116(4) . . ?
C45A N41A C41A 123.7(11) . . ?
C43A N42A C46A 117(3) . . ?
C43A N42A C47A 122(3) . . ?
C46A N42A C47A 121.5(9) . . ?
N41A C41A H41C 119.8 . . ?
N41A C41A C42A 120.5(12) . . ?
C42A C41A H41C 119.8 . . ?
C41A C42A H42A 119.8 . . ?
C41A C42A C43A 120(3) . . ?
C43A C42A H42A 119.8 . . ?
N42A C43A C42A 123(6) . . ?
N42A C43A C44A 119(5) . . ?
C42A C43A C44A 115(4) . . ?
C43A C44A H44A 120.7 . . ?
C45A C44A C43A 119(3) . . ?
C45A C44A H44A 120.7 . . ?
N41A C45A C44A 120.8(12) . . ?
N41A C45A H45A 119.6 . . ?
C44A C45A H45A 119.6 . . ?
N42A C46A H46D 109.5 . . ?
N42A C46A H46E 109.5 . . ?
N42A C46A H46F 109.5 . . ?
H46D C46A H46E 109.5 . . ?
H46D C46A H46F 109.5 . . ?
H46E C46A H46F 109.5 . . ?
N42A C47A H47D 109.5 . . ?
N42A C47A H47E 109.5 . . ?
N42A C47A H47F 109.5 . . ?
H47D C47A H47E 109.5 . . ?
H47D C47A H47F 109.5 . . ?
H47E C47A H47F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O21 1.06(4) 1.42(4) 2.4762(19) 173(4) .
C9 H9A Cl2 0.99 2.96 3.730(2) 135.3 2_:56
C9 H9B O21 0.99 2.62 3.330(3) 128.7 1_655
C27 H27 Cl24 0.95 2.59 3.507(5) 163.5 .
C30 H30B Cl24 0.99 2.86 3.349(5) 111.2 .
C30 H30B O22 0.99 2.52 3.459(3) 157.4 1_455
N41 H41 O22 0.82(5) 1.90(5) 2.675(4) 159(5) .
C41 H41A O1 0.95 2.61 3.286(13) 128.4 .
C41 H41A N2 0.95 2.36 3.282(14) 164.2 .
C46 H46A O22 0.98 2.24 3.165(11) 156.1 2_966
C47 H47C O1 0.98 2.41 3.145(12) 131.6 2_966
N41A H41B O2 0.83(6) 2.14(6) 2.830(4) 140(5) 2_757
N41A H41B O21 0.83(6) 2.53(5) 3.135(4) 130(5) 2_757
C41A H41C N22 0.95 2.48 3.429(16) 173.2 2_757
C45A H45A O2 0.95 2.59 3.056(16) 110.3 2_757
C45A H45A Cl25 0.95 2.98 3.634(15) 127.4 2_667
C46A H46F O2 0.98 2.27 3.198(16) 157.7 .
C47A H47F O21 0.98 2.39 3.295(17) 153.1 .

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 C11 C12 C13 178.66(15) . . . . ?
Cl2 C13 C14 C15 -178.27(15) . . . . ?
O1 C1 C2 N2 -2.0(3) . . . . ?
O1 C1 C2 C3 178.48(18) . . . . ?
O2 C1 C2 N2 177.68(19) . . . . ?
O2 C1 C2 C3 -1.9(3) . . . . ?
N1 N2 C2 C1 179.83(17) . . . . ?
N1 N2 C2 C3 -0.6(2) . . . . ?
N1 C9 C10 C11 167.54(17) . . . . ?
N1 C9 C10 C15 -13.2(3) . . . . ?
N2 N1 C8 C3 -1.3(2) . . . . ?
N2 N1 C8 C7 176.9(2) . . . . ?
N2 N1 C9 C10 -91.8(2) . . . . ?
N2 C2 C3 C4 -179.0(2) . . . . ?
N2 C2 C3 C8 -0.2(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 C8 179.38(18) . . . . ?
C2 C3 C4 C5 177.2(2) . . . . ?
C2 C3 C8 N1 0.9(2) . . . . ?
C2 C3 C8 C7 -177.55(18) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C3 C8 N1 179.89(17) . . . . ?
C4 C3 C8 C7 1.5(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 N1 -178.6(2) . . . . ?
C6 C7 C8 C3 -0.6(3) . . . . ?
C8 N1 N2 C2 1.2(2) . . . . ?
C8 N1 C9 C10 86.6(2) . . . . ?
C8 C3 C4 C5 -1.4(3) . . . . ?
C9 N1 N2 C2 179.77(17) . . . . ?
C9 N1 C8 C3 -179.73(18) . . . . ?
C9 N1 C8 C7 -1.5(3) . . . . ?
C9 C10 C11 Cl1 0.7(3) . . . . ?
C9 C10 C11 C12 -179.88(18) . . . . ?
C9 C10 C15 C14 -179.32(18) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C10 C15 C14 -0.1(3) . . . . ?
C11 C12 C13 Cl2 179.02(15) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C10 -0.8(3) . . . . ?
C15 C10 C11 Cl1 -178.53(14) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
Cl23 C32 C33 C34 -176.23(15) . . . . ?
Cl25 C34 C35 C36 179.64(15) . . . . ?
O21 C21 C22 N22 6.3(3) . . . . ?
O21 C21 C22 C23 -171.68(19) . . . . ?
O22 C21 C22 N22 -173.8(2) . . . . ?
O22 C21 C22 C23 8.2(3) . . . . ?
N21 N22 C22 C21 -178.79(18) . . . . ?
N21 N22 C22 C23 -0.5(2) . . . . ?
N21 C30 C31 C32 -76.9(2) . . . . ?
N21 C30 C31 C36 103.6(2) . . . . ?
N22 N21 C28 C23 -0.9(2) . . . . ?
N22 N21 C28 C27 177.4(2) . . . . ?
N22 N21 C30 C31 115.7(2) . . . . ?
N22 C22 C23 C24 -177.0(2) . . . . ?
N22 C22 C23 C28 0.0(2) . . . . ?
C21 C22 C23 C24 1.3(4) . . . . ?
C21 C22 C23 C28 178.18(19) . . . . ?
C22 C23 C24 C25 176.7(2) . . . . ?
C22 C23 C28 N21 0.6(2) . . . . ?
C22 C23 C28 C27 -178.0(2) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C23 C28 N21 178.08(18) . . . . ?
C24 C23 C28 C27 -0.5(3) . . . . ?
C24 C25 C26 C27 0.0(4) . . . . ?
C25 C26 C27 C28 -0.4(4) . . . . ?
C26 C27 C28 N21 -177.5(2) . . . . ?
C26 C27 C28 C23 0.6(3) . . . . ?
C28 N21 N22 C22 0.9(2) . . . . ?
C28 N21 C30 C31 -70.8(3) . . . . ?
C28 C23 C24 C25 0.1(3) . . . . ?
C30 N21 N22 C22 175.39(17) . . . . ?
C30 N21 C28 C23 -174.84(18) . . . . ?
C30 N21 C28 C27 3.5(4) . . . . ?
C30 C31 C32 Cl23 -5.4(3) . . . . ?
C30 C31 C32 C33 177.85(18) . . . . ?
C30 C31 C36 Cl24 4.0(4) . . . . ?
C30 C31 C36 C35 -177.74(18) . . . . ?
C31 C32 C33 C34 0.6(3) . . . . ?
C32 C31 C36 Cl24 -175.6(3) . . . . ?
C32 C31 C36 C35 2.7(3) . . . . ?
C32 C33 C34 Cl25 -179.55(15) . . . . ?
C32 C33 C34 C35 1.4(3) . . . . ?
C33 C34 C35 C36 -1.4(3) . . . . ?
C34 C35 C36 Cl24 177.9(2) . . . . ?
C34 C35 C36 C31 -0.8(3) . . . . ?
C36 C31 C32 Cl23 174.14(15) . . . . ?
C36 C31 C32 C33 -2.6(3) . . . . ?
N41 C41 C42 C43 1.8(18) . . . . ?
N42 C43 C44 C45 -178.5(12) . . . . ?
C41 N41 C45 C44 -0.1(16) . . . . ?
C41 C42 C43 N42 178.0(13) . . . . ?
C41 C42 C43 C44 -3(2) . . . . ?
C42 C43 C44 C45 2(2) . . . . ?
C43 C44 C45 N41 -0.8(18) . . . . ?
C45 N41 C41 C42 -0.4(17) . . . . ?
C46 N42 C43 C42 -2(2) . . . . ?
C46 N42 C43 C44 178.8(11) . . . . ?
C47 N42 C43 C42 -178.2(13) . . . . ?
C47 N42 C43 C44 2(2) . . . . ?
N41A C41A C42A C43A -6(6) . . . . ?
N42A C43A C44A C45A -173(7) . . . . ?
C41A N41A C45A C44A -2(2) . . . . ?
C41A C42A C43A N42A 171(7) . . . . ?
C41A C42A C43A C44A 11(12) . . . . ?
C42A C43A C44A C45A -13(11) . . . . ?
C43A C44A C45A N41A 9(6) . . . . ?
C45A N41A C41A C42A 1(2) . . . . ?
C46A N42A C43A C42A 12(12) . . . . ?
C46A N42A C43A C44A 171(6) . . . . ?
C47A N42A C43A C42A -170(6) . . . . ?
C47A N42A C43A C44A -11(13) . . . . ?

_olex2_submission_original_sample_id L3-21-C2
_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 1.797
_oxdiff_exptl_absorpt_empirical_full_min 0.753
####################################################################### 
# 
# 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_LON-4DMAP_1-1dihydrate
_database_code_depnum_ccdc_archive 'CCDC 1531961'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Cl2 N2 O2, C7 H11 N2, 2(H2 O)'
_chemical_formula_sum            'C22 H24 Cl2 N4 O4'
_chemical_formula_weight         479.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H24 Cl2 N4 O4'
_chemical_oxdiff_usercomment     L3-93-C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.0507(2)
_cell_length_b                   9.0330(2)
_cell_length_c                   19.0712(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.214(2)
_cell_angle_gamma                90
_cell_volume                     2219.24(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11180
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.3920
_cell_measurement_theta_min      3.0370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 27 0.0355
2 10 -18 0.3115
13 8 5 0.2622
1 -12 -7 0.4563
-1 12 7 0.4013
18 0 1 0.0609
-18 0 -1 0.0609
4 0 -27 0.0747

_exptl_crystal_size_max          0.898
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.11
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
-4.0112 0.0001 27.0308 0.9100 -0.3369 0.2670
2.0269 9.9971 -18.0203 -0.8005 0.2972 0.5806
13.0161 7.9891 5.0199 0.2538 0.7426 0.6089
0.9794 -11.9961 -7.0091 -0.0174 -0.0436 -0.9768
-0.9794 11.9961 7.0091 0.0174 0.0436 0.9768
18.0028 -0.0110 1.0189 0.3393 0.9371 -0.0504
-18.0028 0.0110 -1.0189 -0.3393 -0.9371 0.0504
4.0112 -0.0001 -27.0308 -0.9100 0.3369 -0.2670

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.501
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00   5.00   0.50   20.00    --   21.04 -20.00-113.00  134
  2  ω    -12.00  49.00   0.50   20.00    --  -21.98  20.00  53.00  122
  3  ω    -39.00 -13.00   0.50   20.00    --  -21.98 -20.00-113.00   52
  4  ω     -9.00  97.00   0.50   20.00    --   21.04  57.00-180.00  212
  5  ω    -10.00  34.00   0.50   20.00    --   21.04 -38.00-150.00   88
  6  ω    -48.00  54.00   0.50   20.00    --  -21.98  57.00 -90.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0167901000
_diffrn_orient_matrix_UB_12      -0.0183010000
_diffrn_orient_matrix_UB_13      0.0361572000
_diffrn_orient_matrix_UB_21      0.0523276000
_diffrn_orient_matrix_UB_22      0.0106491000
_diffrn_orient_matrix_UB_23      -0.0046969000
_diffrn_orient_matrix_UB_31      -0.0032866000
_diffrn_orient_matrix_UB_32      0.0756739000
_diffrn_orient_matrix_UB_33      0.0093914000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4628
_reflns_number_total             5078
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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         0.426
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5078
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+1.4505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O22(H22A,H22B), O21(H21B,H21C)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C21(H21A),
 C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.89170(3) 0.66725(4) 0.39789(2) 0.01965(9) Uani 1 1 d . . . . .
Cl2 Cl 0.87811(3) 1.11068(4) 0.58350(2) 0.02348(9) Uani 1 1 d . . . . .
O1 O 0.47424(7) 0.58069(12) 0.36947(5) 0.0207(2) Uani 1 1 d . . . . .
O2 O 0.49767(8) 0.44741(13) 0.27412(5) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.76597(8) 0.42264(12) 0.45192(6) 0.0128(2) Uani 1 1 d . . . . .
N2 N 0.67276(8) 0.49211(12) 0.43608(6) 0.0130(2) Uani 1 1 d . . . . .
C1 C 0.52589(10) 0.49439(15) 0.33568(7) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.62979(10) 0.44244(14) 0.37228(7) 0.0132(2) Uani 1 1 d . . . . .
C3 C 0.69623(10) 0.33759(14) 0.34559(7) 0.0127(2) Uani 1 1 d . . . . .
C4 C 0.69107(10) 0.25139(15) 0.28364(7) 0.0158(3) Uani 1 1 d . . . . .
H4 H 0.6321 0.2554 0.2473 0.019 Uiso 1 1 calc R . . . .
C5 C 0.77438(11) 0.16082(16) 0.27723(7) 0.0182(3) Uani 1 1 d . . . . .
H5 H 0.7720 0.1008 0.2361 0.022 Uiso 1 1 calc R . . . .
C6 C 0.86325(11) 0.15532(15) 0.33056(7) 0.0176(3) Uani 1 1 d . . . . .
H6 H 0.9196 0.0929 0.3241 0.021 Uiso 1 1 calc R . . . .
C7 C 0.86987(10) 0.23890(15) 0.39191(7) 0.0156(3) Uani 1 1 d . . . . .
H7 H 0.9295 0.2356 0.4277 0.019 Uiso 1 1 calc R . . . .
C8 C 0.78418(10) 0.32884(14) 0.39875(7) 0.0125(2) Uani 1 1 d . . . . .
C9 C 0.83673(10) 0.45825(15) 0.51689(7) 0.0144(3) Uani 1 1 d . . . . .
H9A H 0.9059 0.4165 0.5136 0.017 Uiso 1 1 calc R . . . .
H9B H 0.8114 0.4101 0.5575 0.017 Uiso 1 1 calc R . . . .
C10 C 0.84795(9) 0.62233(14) 0.53139(7) 0.0127(2) Uani 1 1 d . . . . .
C11 C 0.87083(10) 0.72541(15) 0.48157(7) 0.0140(3) Uani 1 1 d . . . . .
C12 C 0.87948(10) 0.87583(15) 0.49660(7) 0.0159(3) Uani 1 1 d . . . . .
H12 H 0.8934 0.9446 0.4616 0.019 Uiso 1 1 calc R . . . .
C13 C 0.86717(10) 0.92291(15) 0.56403(8) 0.0159(3) Uani 1 1 d . . . . .
C14 C 0.84757(10) 0.82444(15) 0.61609(7) 0.0169(3) Uani 1 1 d . . . . .
H14 H 0.8412 0.8581 0.6624 0.020 Uiso 1 1 calc R . . . .
C15 C 0.83743(10) 0.67512(15) 0.59865(7) 0.0154(3) Uani 1 1 d . . . . .
H15 H 0.8229 0.6068 0.6336 0.019 Uiso 1 1 calc R . . . .
N21 N 0.49506(9) 0.72377(14) 0.49090(7) 0.0185(2) Uani 1 1 d . . . . .
H21 H 0.5030(15) 0.663(2) 0.4551(10) 0.029(5) Uiso 1 1 d . . . . .
N22 N 0.45356(9) 1.02088(14) 0.64886(7) 0.0211(3) Uani 1 1 d . . . . .
C21 C 0.56667(11) 0.73349(16) 0.55012(8) 0.0200(3) Uani 1 1 d . . . . .
H21A H 0.6264 0.6720 0.5546 0.024 Uiso 1 1 calc R . . . .
C22 C 0.55573(11) 0.82899(16) 0.60369(8) 0.0191(3) Uani 1 1 d . . . . .
H22 H 0.6074 0.8331 0.6449 0.023 Uiso 1 1 calc R . . . .
C23 C 0.46685(10) 0.92288(15) 0.59812(7) 0.0164(3) Uani 1 1 d . . . . .
C24 C 0.39223(10) 0.90728(15) 0.53539(7) 0.0167(3) Uani 1 1 d . . . . .
H24 H 0.3308 0.9655 0.5292 0.020 Uiso 1 1 calc R . . . .
C25 C 0.40876(11) 0.80884(16) 0.48413(8) 0.0180(3) Uani 1 1 d . . . . .
H25 H 0.3583 0.7998 0.4425 0.022 Uiso 1 1 calc R . . . .
C26 C 0.52884(14) 1.0336(2) 0.71408(9) 0.0384(4) Uani 1 1 d . . . . .
H26A H 0.5411 0.9357 0.7359 0.058 Uiso 1 1 calc GR . . . .
H26B H 0.5016 1.1004 0.7472 0.058 Uiso 1 1 calc GR . . . .
H26C H 0.5942 1.0732 0.7029 0.058 Uiso 1 1 calc GR . . . .
C27 C 0.36219(12) 1.11666(17) 0.64084(8) 0.0237(3) Uani 1 1 d . . . . .
H27A H 0.3593 1.1762 0.5976 0.036 Uiso 1 1 calc GR . . . .
H27B H 0.3665 1.1823 0.6821 0.036 Uiso 1 1 calc GR . . . .
H27C H 0.2995 1.0557 0.6374 0.036 Uiso 1 1 calc GR . . . .
O22 O 0.29332(9) 0.37141(16) 0.24925(7) 0.0380(3) Uani 1 1 d . . . . .
H22A H 0.2668 0.4445 0.2679 0.057 Uiso 1 1 d G . . . .
H22B H 0.3578 0.3865 0.2503 0.057 Uiso 1 1 d G . . . .
O21 O 0.26524(8) 0.62382(12) 0.33020(6) 0.0240(2) Uani 1 1 d . . . . .
H21B H 0.3309 0.6151 0.3395 0.036 Uiso 1 1 d G . . . .
H21C H 0.2498 0.7005 0.3049 0.036 Uiso 1 1 d G . . . .


_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 C11 1.7424(13) . ?
Cl2 C13 1.7373(14) . ?
O1 C1 1.2714(17) . ?
O2 C1 1.2473(17) . ?
N1 N2 1.3591(15) . ?
N1 C8 1.3711(17) . ?
N1 C9 1.4578(16) . ?
N2 C2 1.3334(17) . ?
C1 C2 1.4975(18) . ?
C2 C3 1.4316(18) . ?
C3 C4 1.4074(18) . ?
C3 C8 1.4067(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3816(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.416(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.3836(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.4052(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5106(18) . ?
C10 C11 1.3963(18) . ?
C10 C15 1.3956(18) . ?
C11 C12 1.3895(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3881(19) . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.3905(19) . ?
C15 H15 0.9500 . ?
N21 H21 0.90(2) . ?
N21 C21 1.3486(19) . ?
N21 C25 1.3524(18) . ?
N22 C23 1.3431(19) . ?
N22 C26 1.461(2) . ?
N22 C27 1.4614(19) . ?
C21 H21A 0.9500 . ?
C21 C22 1.362(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.4271(19) . ?
C23 C24 1.4235(19) . ?
C24 H24 0.9500 . ?
C24 C25 1.364(2) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O22 H22A 0.8498 . ?
O22 H22B 0.8498 . ?
O21 H21B 0.8500 . ?
O21 H21C 0.8500 . ?

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
N2 N1 C8 112.08(10) . . ?
N2 N1 C9 120.64(10) . . ?
C8 N1 C9 127.14(11) . . ?
C2 N2 N1 106.15(10) . . ?
O1 C1 C2 118.03(12) . . ?
O2 C1 O1 125.81(13) . . ?
O2 C1 C2 116.16(12) . . ?
N2 C2 C1 122.47(12) . . ?
N2 C2 C3 110.91(11) . . ?
C3 C2 C1 126.62(12) . . ?
C4 C3 C2 135.57(12) . . ?
C8 C3 C2 104.58(11) . . ?
C8 C3 C4 119.85(12) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.99(12) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.53(13) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.43(12) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.6 . . ?
C6 C7 C8 116.81(12) . . ?
C8 C7 H7 121.6 . . ?
N1 C8 C3 106.28(11) . . ?
N1 C8 C7 131.35(12) . . ?
C7 C8 C3 122.36(12) . . ?
N1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
N1 C9 C10 113.69(11) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 C9 123.69(12) . . ?
C15 C10 C9 118.86(12) . . ?
C15 C10 C11 117.44(12) . . ?
C10 C11 Cl1 120.27(10) . . ?
C12 C11 Cl1 117.66(10) . . ?
C12 C11 C10 122.06(12) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.23(12) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 Cl2 118.64(11) . . ?
C14 C13 Cl2 119.44(11) . . ?
C14 C13 C12 121.92(13) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.18(13) . . ?
C15 C14 H14 120.9 . . ?
C10 C15 H15 118.9 . . ?
C14 C15 C10 122.12(13) . . ?
C14 C15 H15 118.9 . . ?
C21 N21 H21 122.0(12) . . ?
C21 N21 C25 119.86(12) . . ?
C25 N21 H21 118.2(12) . . ?
C23 N22 C26 121.22(13) . . ?
C23 N22 C27 120.81(12) . . ?
C26 N22 C27 117.96(13) . . ?
N21 C21 H21A 119.1 . . ?
N21 C21 C22 121.84(13) . . ?
C22 C21 H21A 119.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.14(13) . . ?
C23 C22 H22 119.9 . . ?
N22 C23 C22 122.36(13) . . ?
N22 C23 C24 121.39(13) . . ?
C24 C23 C22 116.25(13) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.10(13) . . ?
C25 C24 H24 120.0 . . ?
N21 C25 C24 121.79(13) . . ?
N21 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
N22 C26 H26A 109.5 . . ?
N22 C26 H26B 109.5 . . ?
N22 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N22 C27 H27A 109.5 . . ?
N22 C27 H27B 109.5 . . ?
N22 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
H22A O22 H22B 109.5 . . ?
H21B O21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 O1 0.90(2) 1.78(2) 2.6279(16) 157.5(18) .
O22 H22A O21 0.85 2.01 2.8102(17) 156.5 .
O22 H22B O2 0.85 1.89 2.7209(15) 165.2 .
O21 H21B O1 0.85 1.89 2.7383(14) 173.0 .
O21 H21C O22 0.85 1.89 2.7407(16) 176.1 2

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_original_sample_id L3-93-C
_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 1.677
_oxdiff_exptl_absorpt_empirical_full_min 0.556
####################################################################### 
# 
# 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_LON-246TAPYM
_database_code_depnum_ccdc_archive 'CCDC 1531950'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Cl2 N2 O2, C4 H8 N5'
_chemical_formula_sum            'C19 H17 Cl2 N7 O2'
_chemical_formula_weight         446.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H17 N7 O2 Cl2'
_chemical_oxdiff_usercomment     L3-04-B3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.77896(16)
_cell_length_b                   31.5718(7)
_cell_length_c                   7.72521(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.1388(19)
_cell_angle_gamma                90
_cell_volume                     1882.57(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23530
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.5450
_cell_measurement_theta_min      3.2590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -37 4 0.1371
6 -24 6 0.2535
10 21 -1 0.1501
7 33 -3 0.1096
-2 34 -6 0.1756
-10 -22 1 0.1596
-1 5 11 0.0596
4 -22 -9 0.1027
1 -1 -11 0.0791
-2 11 11 0.0547

_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.146
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
-4.4949 -37.0510 4.4985 0.1590 0.7220 0.6701
6.0230 -24.0493 5.9848 -0.0760 -0.2446 0.9576
9.5112 21.0183 -0.5108 -0.2528 -0.9569 0.0063
7.0019 33.0402 -3.0035 -0.2030 -0.8822 -0.4236
-1.5186 34.0594 -6.4903 -0.0608 -0.2032 -0.9712
-9.5114 -22.0190 0.5103 0.2438 0.9705 0.0092
-1.4648 4.9450 10.5215 0.8103 -0.2062 0.4948
3.9699 -21.9648 -9.0327 -0.9721 0.2231 -0.0476
0.9632 -0.9395 -11.0193 -0.7858 0.1994 -0.6055
-2.4649 10.9491 10.5265 0.9078 -0.2161 0.3642

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            29914
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.938
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  53.00   0.50   20.00    --   21.04 -62.00-125.00  216
  2  ω    -11.00  97.00   0.50   20.00    --   21.04  62.00  12.00  216
  3  ω    -54.00  54.00   0.50   20.00    --  -21.98  62.00  12.00  216
  4  ω    -98.00  10.00   0.50   20.00    --  -21.98 -62.00-125.00  216
  5  ω    -10.00  97.00   0.50   20.00    --   21.04  57.00 150.00  214
  6  ω   -104.00  13.00   0.50   20.00    --  -21.98 -77.00 120.00  234
  7  ω    -53.00  -5.00   0.50   20.00    --  -21.98  57.00 120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0429450000
_diffrn_orient_matrix_UB_12      0.0090280000
_diffrn_orient_matrix_UB_13      0.0667904000
_diffrn_orient_matrix_UB_21      -0.0718177000
_diffrn_orient_matrix_UB_22      -0.0135923000
_diffrn_orient_matrix_UB_23      -0.0232101000
_diffrn_orient_matrix_UB_31      0.0380331000
_diffrn_orient_matrix_UB_32      -0.0154646000
_diffrn_orient_matrix_UB_33      0.0595899000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4236
_reflns_number_total             4304
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.533
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.185
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+2.4134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.78303(6) 0.72695(2) 0.72600(7) 0.02438(12) Uani 1 1 d . . . . .
Cl2 Cl 0.25368(6) 0.82447(2) 0.44697(7) 0.02553(12) Uani 1 1 d . . . . .
O2 O 0.36621(18) 0.55716(5) -0.04362(18) 0.0251(3) Uani 1 1 d . . . . .
O1 O 0.17204(17) 0.55652(5) 0.14628(18) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.54785(19) 0.62615(5) 0.45352(19) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.40913(19) 0.60309(5) 0.38090(19) 0.0153(3) Uani 1 1 d . . . . .
C1 C 0.3152(2) 0.56680(6) 0.1000(2) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.4392(2) 0.59315(5) 0.2200(2) 0.0144(3) Uani 1 1 d . . . . .
C3 C 0.5995(2) 0.61132(5) 0.1831(2) 0.0143(3) Uani 1 1 d . . . . .
C4 C 0.6931(2) 0.61270(6) 0.0394(2) 0.0169(3) Uani 1 1 d . . . . .
H4 H 0.6518 0.5986 -0.0662 0.020 Uiso 1 1 calc R . . . .
C5 C 0.8466(2) 0.63507(6) 0.0547(3) 0.0199(4) Uani 1 1 d . . . . .
H5 H 0.9111 0.6364 -0.0418 0.024 Uiso 1 1 calc R . . . .
C6 C 0.9096(2) 0.65605(6) 0.2114(3) 0.0200(4) Uani 1 1 d . . . . .
H6 H 1.0161 0.6711 0.2178 0.024 Uiso 1 1 calc R . . . .
C7 C 0.8212(2) 0.65537(6) 0.3550(2) 0.0180(4) Uani 1 1 d . . . . .
H7 H 0.8636 0.6695 0.4603 0.022 Uiso 1 1 calc R . . . .
C8 C 0.6644(2) 0.63261(5) 0.3372(2) 0.0145(3) Uani 1 1 d . . . . .
C9 C 0.5416(2) 0.64910(6) 0.6163(2) 0.0166(3) Uani 1 1 d . . . . .
H9A H 0.6593 0.6504 0.6817 0.020 Uiso 1 1 calc R . . . .
H9B H 0.4657 0.6338 0.6890 0.020 Uiso 1 1 calc R . . . .
C10 C 0.4732(2) 0.69381(6) 0.5821(2) 0.0162(3) Uani 1 1 d . . . . .
C11 C 0.5712(2) 0.73032(6) 0.6209(2) 0.0178(4) Uani 1 1 d . . . . .
C12 C 0.5061(2) 0.77072(6) 0.5805(2) 0.0189(4) Uani 1 1 d . . . . .
H12 H 0.5756 0.7952 0.6071 0.023 Uiso 1 1 calc R . . . .
C13 C 0.3375(3) 0.77427(6) 0.5007(2) 0.0195(4) Uani 1 1 d . . . . .
C14 C 0.2336(3) 0.73887(6) 0.4623(3) 0.0220(4) Uani 1 1 d . . . . .
H14 H 0.1174 0.7418 0.4091 0.026 Uiso 1 1 calc R . . . .
C15 C 0.3029(2) 0.69917(6) 0.5030(2) 0.0205(4) Uani 1 1 d . . . . .
H15 H 0.2326 0.6749 0.4763 0.025 Uiso 1 1 calc R . . . .
N21 N 0.7109(2) 0.52143(5) 0.4403(2) 0.0181(3) Uani 1 1 d . . . . .
N22 N 0.9792(2) 0.55330(5) 0.4077(2) 0.0154(3) Uani 1 1 d . . . . .
H22 H 1.058(3) 0.5576(8) 0.339(3) 0.025(6) Uiso 1 1 d . . . . .
N23 N 0.5985(2) 0.52702(6) 0.7000(2) 0.0231(4) Uani 1 1 d . . . . .
H23A H 0.505(4) 0.5125(8) 0.650(3) 0.033(7) Uiso 1 1 d . . . . .
H23B H 0.608(3) 0.5344(8) 0.810(4) 0.030(7) Uiso 1 1 d . . . . .
N24 N 0.8258(2) 0.51834(5) 0.1772(2) 0.0186(3) Uani 1 1 d . . . . .
H24A H 0.914(3) 0.5216(7) 0.118(3) 0.018(6) Uiso 1 1 d . . . . .
H24B H 0.757(4) 0.4992(9) 0.139(3) 0.033(7) Uiso 1 1 d . . . . .
N25 N 1.1583(2) 0.58434(5) 0.6336(2) 0.0219(3) Uani 1 1 d . . . . .
H25A H 1.236(4) 0.5855(9) 0.557(4) 0.036(7) Uiso 1 1 d . . . . .
H25B H 1.196(4) 0.5811(10) 0.745(4) 0.047(8) Uiso 1 1 d . . . . .
C21 C 0.8808(2) 0.55606(6) 0.6843(2) 0.0182(4) Uani 1 1 d . . . . .
H21 H 0.8946 0.5642 0.8036 0.022 Uiso 1 1 calc R . . . .
C22 C 0.7309(2) 0.53488(6) 0.6098(2) 0.0182(4) Uani 1 1 d . . . . .
C23 C 0.8356(2) 0.53068(5) 0.3444(2) 0.0160(3) Uani 1 1 d . . . . .
C24 C 1.0071(2) 0.56472(5) 0.5798(2) 0.0172(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7472(19) . ?
Cl2 C13 1.744(2) . ?
O2 C1 1.261(2) . ?
O1 C1 1.254(2) . ?
N1 N2 1.363(2) . ?
N1 C8 1.369(2) . ?
N1 C9 1.458(2) . ?
N2 C2 1.330(2) . ?
C1 C2 1.503(2) . ?
C2 C3 1.433(2) . ?
C3 C4 1.402(2) . ?
C3 C8 1.406(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.413(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.407(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.520(2) . ?
C10 C11 1.394(3) . ?
C10 C15 1.398(3) . ?
C11 C12 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 C14 1.390(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
N21 C22 1.367(2) . ?
N21 C23 1.325(2) . ?
N22 H22 0.87(3) . ?
N22 C23 1.364(2) . ?
N22 C24 1.369(2) . ?
N23 H23A 0.91(3) . ?
N23 H23B 0.88(3) . ?
N23 C22 1.337(2) . ?
N24 H24A 0.88(2) . ?
N24 H24B 0.83(3) . ?
N24 C23 1.342(2) . ?
N25 H25A 0.90(3) . ?
N25 H25B 0.88(3) . ?
N25 C24 1.349(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.404(3) . ?
C21 C24 1.374(3) . ?

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
N2 N1 C8 111.38(14) . . ?
N2 N1 C9 120.72(14) . . ?
C8 N1 C9 126.03(15) . . ?
C2 N2 N1 106.74(14) . . ?
O2 C1 C2 115.37(16) . . ?
O1 C1 O2 125.15(17) . . ?
O1 C1 C2 119.47(16) . . ?
N2 C2 C1 122.19(16) . . ?
N2 C2 C3 110.51(15) . . ?
C3 C2 C1 127.30(16) . . ?
C4 C3 C2 136.11(17) . . ?
C4 C3 C8 119.24(16) . . ?
C8 C3 C2 104.63(15) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.50(17) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.20(17) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.87(17) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 121.8 . . ?
C6 C7 C8 116.31(17) . . ?
C8 C7 H7 121.8 . . ?
N1 C8 C3 106.68(15) . . ?
N1 C8 C7 130.44(16) . . ?
C3 C8 C7 122.88(16) . . ?
N1 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
N1 C9 C10 111.11(14) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C11 C10 C9 124.06(16) . . ?
C11 C10 C15 117.21(17) . . ?
C15 C10 C9 118.72(16) . . ?
C10 C11 Cl1 120.58(15) . . ?
C12 C11 Cl1 117.10(14) . . ?
C12 C11 C10 122.32(17) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.19(17) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 Cl2 119.06(15) . . ?
C12 C13 C14 121.65(18) . . ?
C14 C13 Cl2 119.29(15) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.65(18) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 121.97(18) . . ?
C14 C15 H15 119.0 . . ?
C23 N21 C22 117.61(16) . . ?
C23 N22 H22 118.1(16) . . ?
C23 N22 C24 120.63(16) . . ?
C24 N22 H22 120.8(17) . . ?
H23A N23 H23B 121(2) . . ?
C22 N23 H23A 119.9(17) . . ?
C22 N23 H23B 118.8(17) . . ?
H24A N24 H24B 114(2) . . ?
C23 N24 H24A 120.7(15) . . ?
C23 N24 H24B 120.3(19) . . ?
H25A N25 H25B 119(3) . . ?
C24 N25 H25A 116.7(18) . . ?
C24 N25 H25B 115(2) . . ?
C22 C21 H21 120.9 . . ?
C24 C21 H21 120.9 . . ?
C24 C21 C22 118.17(17) . . ?
N21 C22 C21 122.01(17) . . ?
N23 C22 N21 116.02(17) . . ?
N23 C22 C21 121.97(17) . . ?
N21 C23 N22 122.62(17) . . ?
N21 C23 N24 121.10(17) . . ?
N24 C23 N22 116.28(17) . . ?
N22 C24 C21 118.68(17) . . ?
N25 C24 N22 116.57(17) . . ?
N25 C24 C21 124.74(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9A Cl1 0.99 2.61 3.1451(18) 114.1 .
N22 H22 O1 0.87(3) 1.83(3) 2.663(2) 161(2) 1_655
N23 H23A N21 0.91(3) 2.04(3) 2.942(2) 174(2) 3_666
N23 H23B O2 0.88(3) 2.42(3) 2.997(2) 124(2) 1_556
N24 H24A O1 0.88(2) 2.27(2) 2.987(2) 138(2) 1_655
N24 H24B O2 0.83(3) 2.11(3) 2.932(2) 167(3) 3_665
N25 H25A N2 0.90(3) 2.11(3) 2.986(2) 167(2) 1_655
N25 H25B O2 0.88(3) 2.11(3) 2.927(2) 154(3) 1_656

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'MiTeGen micromesh'
_olex2_submission_original_sample_id L3-04-B3
_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 1.697
_oxdiff_exptl_absorpt_empirical_full_min 0.684
