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

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

data_exp_582
_database_code_depnum_ccdc_archive 'CCDC 1548393'
_audit_update_record             
;
2017-05-07 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;
_audit_creation_date             2017-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        3b
_chemical_formula_moiety         'C16 H11 Cl N2 O2'
_chemical_formula_sum            'C16 H11 Cl N2 O2'
_chemical_formula_weight         298.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         2(C16H11ClN2O2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.2425(2)
_cell_length_b                   11.2220(3)
_cell_length_c                   13.7847(3)
_cell_angle_alpha                112.293(2)
_cell_angle_beta                 92.6647(18)
_cell_angle_gamma                104.094(2)
_cell_volume                     1404.75(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21206
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      76.2550
_cell_measurement_theta_min      3.5020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.63
_diffrn_reflns_theta_min         3.51
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  32.00   1.00    2.12    --  -41.49  57.00  90.00  102
  2  ω    -66.00  33.00   1.00    2.12    --  -41.49  38.00   0.00   99
  3  ω    -74.00  35.00   1.00    2.12    --  -41.49  77.00-150.00  109
  4  ω     13.00 115.00   1.00    2.12    --   41.49  57.00-180.00  102
  5  ω     23.00  98.00   1.00    2.12    --   41.49-125.00   0.00   75
  6  ω     57.00 151.00   1.00    8.50    --  112.00 178.00-120.00   94
  7  ω     29.00 109.00   1.00    8.50    --  112.00 -94.00 -90.00   80
  8  ω    100.00 178.00   1.00    8.50    --  112.00 111.00 150.00   78
  9  ω     83.00 178.00   1.00    8.50    --  112.00  61.00 -30.00   95
 10  ω     36.00 116.00   1.00    8.50    --  112.00-111.00  90.00   80
 11  ω    100.00 178.00   1.00    8.50    --  112.00 111.00  30.00   78
 12  ω     29.00 109.00   1.00    8.50    --  112.00 -94.00 -30.00   80
 13  ω     36.00 116.00   1.00    8.50    --  112.00-111.00 150.00   80
 14  ω     83.00 178.00   1.00    8.50    --  112.00  61.00-150.00   95
 15  ω     36.00 116.00   1.00    8.50    --  112.00-111.00 -90.00   80
 16  ω     29.00 109.00   1.00    8.50    --  112.00 -94.00-180.00   80
 17  ω     39.00 138.00   1.00    8.50    --  112.00 -45.00-120.00   99
 18  ω     36.00 116.00   1.00    8.50    --  112.00-111.00  60.00   80
 19  ω     29.00 109.00   1.00    8.50    --  112.00 -94.00-150.00   80
 20  ω     86.00 178.00   1.00    8.50    --  112.00  45.00 120.00   92
 21  ω     36.00 116.00   1.00    8.50    --  112.00-111.00 120.00   80
 22  ω     57.00 151.00   1.00    8.50    --  112.00 178.00 120.00   94
 23  ω     36.00 116.00   1.00    8.50    --  112.00-111.00 -30.00   80
 24  ω     57.00 151.00   1.00    8.50    --  112.00 178.00 -90.00   94
 25  ω     83.00 178.00   1.00    8.50    --  112.00  61.00  90.00   95
 26  ω      9.00 118.00   1.00    2.12    --   41.49  77.00 -30.00  109
 27  ω      9.00 118.00   1.00    2.12    --   41.49  77.00  90.00  109
 28  ω      9.00 118.00   1.00    2.12    --   41.49  77.00 -60.00  109
 29  ω     17.00 116.00   1.00    2.12    --   41.49  38.00 -30.00   99
 30  ω      9.00 118.00   1.00    2.12    --   41.49  77.00-150.00  109
 31  ω     13.00 115.00   1.00    2.12    --   41.49  57.00  60.00  102
 32  ω     86.00 178.00   1.00    8.50    --  112.00  45.00 -90.00   92
 33  ω     83.00 161.00   1.00    8.50    --  112.00  61.00  60.00   78
 34  ω     83.00 178.00   1.00    8.50    --  112.00  61.00   0.00   95
 35  ω     83.00 178.00   1.00    8.50    --  112.00  61.00 -60.00   95
 36  ω     79.00 178.00   1.00    8.50    --  112.00  77.00 150.00   99
 37  ω     83.00 178.00   1.00    8.50    --  112.00  61.00  30.00   95
 38  ω      9.00 118.00   1.00    2.12    --   41.49  77.00-180.00  109
 39  ω     17.00 116.00   1.00    2.12    --   41.49  38.00 150.00   99
 40  ω      9.00 118.00   1.00    2.12    --   41.49  77.00-120.00  109
 41  ω     23.00  98.00   1.00    2.12    --   41.49-125.00-180.00   75
 42  ω     13.00 115.00   1.00    2.12    --   41.49  57.00 -90.00  102
 43  ω      9.00 118.00   1.00    2.12    --   41.49  77.00  60.00  109
 44  ω     13.00 115.00   1.00    2.12    --   41.49  57.00 120.00  102
 45  ω    -47.00 130.00   1.00    2.12    --   41.49   0.00-180.00  177
 46  ω    -47.00 130.00   1.00    2.12    --   41.49   0.00-150.00  177
 47  ω     16.00 115.00   1.00    2.12    --   41.49  41.00  52.00   99
 48  ω     83.00 123.00   1.00    8.50    --  112.00  61.00 -90.00   40
 49  ω     79.00 178.00   1.00    8.50    --  112.00  77.00-180.00   99
 50  ω     83.00 178.00   1.00    8.50    --  112.00  61.00-120.00   95
 51  ω     79.00 178.00   1.00    8.50    --  112.00  77.00 120.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0222092000
_diffrn_orient_matrix_UB_12      -0.0952743000
_diffrn_orient_matrix_UB_13      0.0577690000
_diffrn_orient_matrix_UB_21      -0.1553698000
_diffrn_orient_matrix_UB_22      -0.0287269000
_diffrn_orient_matrix_UB_23      -0.0257748000
_diffrn_orient_matrix_UB_31      -0.0023699000
_diffrn_orient_matrix_UB_32      -0.1184111000
_diffrn_orient_matrix_UB_33      -0.1046221000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5200
_reflns_number_total             5881
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.44a (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         0.272
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.068
_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)+(0.0575P)²+0.2605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C9(H9), C10(H10), C16(H16), C17(H17), C19(H19),
 C20(H20)
2.b X=CH2 refined with riding coordinates:
 N11(H11A,H11B)
;
_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 0.54638(7) 0.70274(7) 0.05419(4) 0.0932(2) Uani 1 1 d . . . . .
O12 O 0.49642(10) 0.80251(10) 0.55657(8) 0.0490(2) Uani 1 1 d . . . . .
O15 O 0.63978(14) 0.67511(13) 0.52743(9) 0.0715(3) Uani 1 1 d . . . . .
N7 N 0.29678(11) 0.65353(12) 0.62624(9) 0.0451(2) Uani 1 1 d . . . . .
N11 N 0.09174(13) 0.49476(15) 0.59217(11) 0.0627(3) Uani 1 1 d . . . . .
H11A H 0.0914 0.4744 0.5254 0.075 Uiso 1 1 calc R . . . .
H11B H 0.0253 0.4532 0.6138 0.075 Uiso 1 1 calc R . . . .
C1 C 0.63477(19) 0.94288(18) 0.84034(14) 0.0690(4) Uani 1 1 d . . . . .
H1 H 0.7120 1.0051 0.8865 0.083 Uiso 1 1 calc R . . . .
C2 C 0.62219(17) 0.91637(16) 0.73176(13) 0.0587(4) Uani 1 1 d . . . . .
H2 H 0.6899 0.9630 0.7062 0.070 Uiso 1 1 calc R . . . .
C3 C 0.51096(14) 0.82244(15) 0.66393(11) 0.0477(3) Uani 1 1 d . . . . .
C4 C 0.40466(14) 0.74893(13) 0.69817(11) 0.0442(3) Uani 1 1 d . . . . .
C5 C 0.41673(16) 0.78094(15) 0.80881(11) 0.0521(3) Uani 1 1 d . . . . .
C6 C 0.53321(19) 0.87691(17) 0.87793(13) 0.0644(4) Uani 1 1 d . . . . .
H6 H 0.5411 0.8956 0.9501 0.077 Uiso 1 1 calc R . . . .
C8 C 0.19646(14) 0.59199(15) 0.66305(12) 0.0484(3) Uani 1 1 d . . . . .
C9 C 0.19637(16) 0.62335(17) 0.77383(13) 0.0581(4) Uani 1 1 d . . . . .
H9 H 0.1221 0.5814 0.7971 0.070 Uiso 1 1 calc R . . . .
C10 C 0.30461(18) 0.71397(17) 0.84381(12) 0.0599(4) Uani 1 1 d . . . . .
H10 H 0.3063 0.7331 0.9158 0.072 Uiso 1 1 calc R . . . .
C13 C 0.57200(14) 0.72999(14) 0.49569(11) 0.0467(3) Uani 1 1 d . . . . .
C14 C 0.56305(13) 0.72711(14) 0.38736(11) 0.0443(3) Uani 1 1 d . . . . .
C16 C 0.48596(13) 0.79429(14) 0.35399(11) 0.0447(3) Uani 1 1 d . . . . .
H16 H 0.4374 0.8441 0.4005 0.054 Uiso 1 1 calc R . . . .
C17 C 0.48146(15) 0.78698(15) 0.25127(12) 0.0517(3) Uani 1 1 d . . . . .
H17 H 0.4296 0.8314 0.2283 0.062 Uiso 1 1 calc R . . . .
C18 C 0.55430(17) 0.71347(17) 0.18372(12) 0.0573(4) Uani 1 1 d . . . . .
C19 C 0.63232(19) 0.6469(2) 0.21549(14) 0.0702(5) Uani 1 1 d . . . . .
H19 H 0.6815 0.5980 0.1689 0.084 Uiso 1 1 calc R . . . .
C20 C 0.63629(18) 0.65411(19) 0.31756(13) 0.0640(4) Uani 1 1 d . . . . .
H20 H 0.6886 0.6096 0.3400 0.077 Uiso 1 1 calc R . . . .
Cl21 Cl 0.03392(9) 0.90690(8) 0.87853(5) 0.1144(3) Uani 1 1 d . . . . .
O12A O 0.02560(10) 0.79920(11) 0.36979(9) 0.0575(3) Uani 1 1 d . . . . .
O15A O 0.23838(11) 0.93758(11) 0.43198(10) 0.0616(3) Uani 1 1 d . . . . .
N7A N 0.16604(10) 0.61523(11) 0.32588(8) 0.0422(2) Uani 1 1 d . . . . .
N11A N 0.27352(14) 0.49525(14) 0.38634(11) 0.0592(3) Uani 1 1 d . . . . .
H11C H 0.2961 0.5676 0.4436 0.071 Uiso 1 1 d GR . . . .
H11D H 0.3427 0.4641 0.3734 0.071 Uiso 1 1 d GR . . . .
C1A C 0.0536(2) 0.7336(2) 0.08992(16) 0.0818(6) Uani 1 1 d . . . . .
H1A H 0.0290 0.7624 0.0386 0.098 Uiso 1 1 calc R . . . .
C2A C 0.02209(19) 0.78949(18) 0.19226(17) 0.0721(5) Uani 1 1 d . . . . .
H2A H -0.0247 0.8543 0.2087 0.086 Uiso 1 1 calc R . . . .
C3A C 0.06018(14) 0.74851(15) 0.26793(12) 0.0521(3) Uani 1 1 d . . . . .
C4A C 0.12974(12) 0.64958(13) 0.24575(10) 0.0434(3) Uani 1 1 d . . . . .
C5A C 0.15858(15) 0.59202(15) 0.14175(11) 0.0519(3) Uani 1 1 d . . . . .
C6A C 0.12011(19) 0.63744(19) 0.06543(13) 0.0699(5) Uani 1 1 d . . . . .
H6A H 0.1406 0.6009 -0.0028 0.084 Uiso 1 1 calc R . . . .
C8A C 0.23308(13) 0.52362(14) 0.30461(11) 0.0460(3) Uani 1 1 d . . . . .
C9A C 0.26052(17) 0.45486(16) 0.20046(13) 0.0597(4) Uani 1 1 d . . . . .
H9A H 0.3030 0.3870 0.1871 0.072 Uiso 1 1 calc R . . . .
C10A C 0.22423(17) 0.48926(18) 0.12175(13) 0.0621(4) Uani 1 1 d . . . . .
H10A H 0.2424 0.4453 0.0538 0.075 Uiso 1 1 calc R . . . .
C13A C 0.13249(14) 0.88057(14) 0.44891(13) 0.0505(3) Uani 1 1 d . . . . .
C14A C 0.10207(15) 0.88762(14) 0.55429(13) 0.0526(3) Uani 1 1 d . . . . .
C16A C -0.02692(17) 0.83359(17) 0.57203(15) 0.0666(4) Uani 1 1 d . . . . .
H16A H -0.0997 0.7939 0.5166 0.080 Uiso 1 1 calc R . . . .
C17A C -0.0478(2) 0.83843(19) 0.67122(18) 0.0777(6) Uani 1 1 d . . . . .
H17A H -0.1343 0.8023 0.6831 0.093 Uiso 1 1 calc R . . . .
C18A C 0.0608(2) 0.89726(18) 0.75270(16) 0.0727(5) Uani 1 1 d . . . . .
C19A C 0.1900(2) 0.9518(2) 0.73742(16) 0.0719(5) Uani 1 1 d . . . . .
H19A H 0.2625 0.9911 0.7931 0.086 Uiso 1 1 calc R . . . .
C20A C 0.20942(17) 0.94671(17) 0.63772(14) 0.0620(4) Uani 1 1 d . . . . .
H20A H 0.2960 0.9835 0.6263 0.074 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 C18 1.7401(15) . ?
O12 C3 1.4052(16) . ?
O12 C13 1.3472(17) . ?
O15 C13 1.1988(16) . ?
N7 C4 1.3663(18) . ?
N7 C8 1.3262(17) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N11 C8 1.349(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.404(2) . ?
C1 C6 1.366(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.361(2) . ?
C3 C4 1.4123(19) . ?
C4 C5 1.4197(19) . ?
C5 C6 1.408(2) . ?
C5 C10 1.422(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.431(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.342(2) . ?
C10 H10 0.9300 . ?
C13 C14 1.4794(18) . ?
C14 C16 1.3866(18) . ?
C14 C20 1.389(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.3848(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(2) . ?
C18 C19 1.376(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(2) . ?
C20 H20 0.9300 . ?
Cl21 C18A 1.736(2) . ?
O12A C3A 1.400(2) . ?
O12A C13A 1.3670(18) . ?
O15A C13A 1.1995(17) . ?
N7A C4A 1.3644(16) . ?
N7A C8A 1.3221(18) . ?
N11A H11C 0.8606 . ?
N11A H11D 0.8611 . ?
N11A C8A 1.3547(18) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.399(3) . ?
C1A C6A 1.359(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.366(2) . ?
C3A C4A 1.408(2) . ?
C4A C5A 1.411(2) . ?
C5A C6A 1.410(2) . ?
C5A C10A 1.418(2) . ?
C6A H6A 0.9300 . ?
C8A C9A 1.428(2) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.347(2) . ?
C10A H10A 0.9300 . ?
C13A C14A 1.477(2) . ?
C14A C16A 1.388(2) . ?
C14A C20A 1.386(2) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.376(3) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.377(3) . ?
C18A C19A 1.378(3) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.380(3) . ?
C20A H20A 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
C13 O12 C3 116.36(10) . . ?
C8 N7 C4 117.72(12) . . ?
H11A N11 H11B 120.0 . . ?
C8 N11 H11A 120.0 . . ?
C8 N11 H11B 120.0 . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.74(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.01(14) . . ?
C3 C2 H2 120.0 . . ?
O12 C3 C4 118.13(12) . . ?
C2 C3 O12 119.20(12) . . ?
C2 C3 C4 122.56(13) . . ?
N7 C4 C3 120.11(12) . . ?
N7 C4 C5 123.33(12) . . ?
C3 C4 C5 116.55(13) . . ?
C4 C5 C10 116.30(14) . . ?
C6 C5 C4 120.29(14) . . ?
C6 C5 C10 123.39(14) . . ?
C1 C6 C5 120.78(15) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N7 C8 N11 117.98(13) . . ?
N7 C8 C9 122.72(14) . . ?
N11 C8 C9 119.30(13) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.25(13) . . ?
C10 C9 H9 120.4 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.52(13) . . ?
C9 C10 H10 119.7 . . ?
O12 C13 C14 112.89(11) . . ?
O15 C13 O12 122.83(13) . . ?
O15 C13 C14 124.28(13) . . ?
C16 C14 C13 122.77(12) . . ?
C16 C14 C20 119.55(13) . . ?
C20 C14 C13 117.68(12) . . ?
C14 C16 H16 120.1 . . ?
C17 C16 C14 119.87(13) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.36(13) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 Cl1 119.15(12) . . ?
C17 C18 C19 121.71(14) . . ?
C19 C18 Cl1 119.14(13) . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.79(15) . . ?
C20 C19 H19 120.6 . . ?
C14 C20 H20 119.6 . . ?
C19 C20 C14 120.72(14) . . ?
C19 C20 H20 119.6 . . ?
C13A O12A C3A 115.20(11) . . ?
C8A N7A C4A 117.86(12) . . ?
H11C N11A H11D 109.4 . . ?
C8A N11A H11C 109.2 . . ?
C8A N11A H11D 109.4 . . ?
C2A C1A H1A 119.9 . . ?
C6A C1A H1A 119.9 . . ?
C6A C1A C2A 120.11(15) . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A C1A 119.80(18) . . ?
C3A C2A H2A 120.1 . . ?
O12A C3A C4A 117.24(12) . . ?
C2A C3A O12A 120.94(16) . . ?
C2A C3A C4A 121.75(17) . . ?
N7A C4A C3A 118.34(13) . . ?
N7A C4A C5A 123.71(13) . . ?
C3A C4A C5A 117.96(13) . . ?
C4A C5A C10A 116.13(13) . . ?
C6A C5A C4A 119.25(16) . . ?
C6A C5A C10A 124.61(16) . . ?
C1A C6A C5A 121.11(17) . . ?
C1A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
N7A C8A N11A 116.96(13) . . ?
N7A C8A C9A 122.37(13) . . ?
N11A C8A C9A 120.67(14) . . ?
C8A C9A H9A 120.4 . . ?
C10A C9A C8A 119.30(15) . . ?
C10A C9A H9A 120.4 . . ?
C5A C10A H10A 119.8 . . ?
C9A C10A C5A 120.47(15) . . ?
C9A C10A H10A 119.8 . . ?
O12A C13A C14A 112.41(12) . . ?
O15A C13A O12A 122.40(14) . . ?
O15A C13A C14A 125.19(14) . . ?
C16A C14A C13A 123.07(15) . . ?
C20A C14A C13A 117.73(13) . . ?
C20A C14A C16A 119.16(16) . . ?
C14A C16A H16A 119.8 . . ?
C17A C16A C14A 120.36(18) . . ?
C17A C16A H16A 119.8 . . ?
C16A C17A H17A 120.3 . . ?
C16A C17A C18A 119.34(17) . . ?
C18A C17A H17A 120.3 . . ?
C17A C18A Cl21 119.39(15) . . ?
C17A C18A C19A 121.58(18) . . ?
C19A C18A Cl21 119.01(18) . . ?
C18A C19A H19A 120.7 . . ?
C18A C19A C20A 118.51(19) . . ?
C20A C19A H19A 120.7 . . ?
C14A C20A H20A 119.5 . . ?
C19A C20A C14A 121.06(16) . . ?
C19A C20A H20A 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C19 C20 -178.95(15) . . . . ?
O12 C3 C4 N7 5.30(19) . . . . ?
O12 C3 C4 C5 -174.13(12) . . . . ?
O12 C13 C14 C16 0.88(19) . . . . ?
O12 C13 C14 C20 -179.49(14) . . . . ?
O15 C13 C14 C16 -178.51(15) . . . . ?
O15 C13 C14 C20 1.1(2) . . . . ?
N7 C4 C5 C6 177.62(14) . . . . ?
N7 C4 C5 C10 -4.0(2) . . . . ?
N7 C8 C9 C10 -3.3(2) . . . . ?
N11 C8 C9 C10 175.76(15) . . . . ?
C1 C2 C3 O12 176.50(15) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C3 C4 N7 -178.48(13) . . . . ?
C2 C3 C4 C5 2.1(2) . . . . ?
C3 O12 C13 O15 6.1(2) . . . . ?
C3 O12 C13 C14 -173.28(11) . . . . ?
C3 C4 C5 C6 -3.0(2) . . . . ?
C3 C4 C5 C10 175.37(13) . . . . ?
C4 N7 C8 N11 -177.95(12) . . . . ?
C4 N7 C8 C9 1.1(2) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C10 C9 1.7(2) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
C6 C5 C10 C9 180.00(16) . . . . ?
C8 N7 C4 C3 -176.76(12) . . . . ?
C8 N7 C4 C5 2.63(19) . . . . ?
C8 C9 C10 C5 1.7(2) . . . . ?
C10 C5 C6 C1 -176.71(17) . . . . ?
C13 O12 C3 C2 77.98(17) . . . . ?
C13 O12 C3 C4 -105.67(14) . . . . ?
C13 C14 C16 C17 -179.71(13) . . . . ?
C13 C14 C20 C19 179.86(17) . . . . ?
C14 C16 C17 C18 -0.3(2) . . . . ?
C16 C14 C20 C19 -0.5(3) . . . . ?
C16 C17 C18 Cl1 179.12(11) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C14 0.0(3) . . . . ?
C20 C14 C16 C17 0.7(2) . . . . ?
Cl21 C18A C19A C20A -178.30(14) . . . . ?
O12A C3A C4A N7A -3.82(18) . . . . ?
O12A C3A C4A C5A 176.51(11) . . . . ?
O12A C13A C14A C16A -8.9(2) . . . . ?
O12A C13A C14A C20A 168.59(13) . . . . ?
O15A C13A C14A C16A 171.79(15) . . . . ?
O15A C13A C14A C20A -10.8(2) . . . . ?
N7A C4A C5A C6A -178.14(13) . . . . ?
N7A C4A C5A C10A 2.62(19) . . . . ?
N7A C8A C9A C10A 4.0(2) . . . . ?
N11A C8A C9A C10A -177.18(14) . . . . ?
C1A C2A C3A O12A -177.66(15) . . . . ?
C1A C2A C3A C4A -0.7(2) . . . . ?
C2A C1A C6A C5A 0.0(3) . . . . ?
C2A C3A C4A N7A 179.13(13) . . . . ?
C2A C3A C4A C5A -0.5(2) . . . . ?
C3A O12A C13A O15A 21.77(19) . . . . ?
C3A O12A C13A C14A -157.59(12) . . . . ?
C3A C4A C5A C6A 1.51(19) . . . . ?
C3A C4A C5A C10A -177.73(13) . . . . ?
C4A N7A C8A N11A 177.14(11) . . . . ?
C4A N7A C8A C9A -3.96(19) . . . . ?
C4A C5A C6A C1A -1.3(2) . . . . ?
C4A C5A C10A C9A -2.6(2) . . . . ?
C6A C1A C2A C3A 1.0(3) . . . . ?
C6A C5A C10A C9A 178.22(15) . . . . ?
C8A N7A C4A C3A -179.03(12) . . . . ?
C8A N7A C4A C5A 0.62(18) . . . . ?
C8A C9A C10A C5A -0.4(2) . . . . ?
C10A C5A C6A C1A 177.91(16) . . . . ?
C13A O12A C3A C2A -111.38(16) . . . . ?
C13A O12A C3A C4A 71.54(16) . . . . ?
C13A C14A C16A C17A 177.28(15) . . . . ?
C13A C14A C20A C19A -177.19(15) . . . . ?
C14A C16A C17A C18A -0.1(3) . . . . ?
C16A C14A C20A C19A 0.4(2) . . . . ?
C16A C17A C18A Cl21 178.52(14) . . . . ?
C16A C17A C18A C19A 0.1(3) . . . . ?
C17A C18A C19A C20A 0.1(3) . . . . ?
C18A C19A C20A C14A -0.3(3) . . . . ?
C20A C14A C16A C17A -0.1(2) . . . . ?

_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 0.206 0.186 0.025 10.8 0.3 ?
2 0.794 0.814 0.975 10.8 0.3 ?

_shelx_SHELXL_version_number     2014/7

_olex2_date_sample_data_collection 2016-12-01
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.767
####################################################################### 
# 
# 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_exp_559
_database_code_depnum_ccdc_archive 'CCDC 1548392'
_audit_update_record             
;
2017-05-07 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;
_audit_creation_date             2017-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            3f
_chemical_name_systematic        SG-HQ1
_chemical_formula_moiety         'C37 H30 N2 O5'
_chemical_formula_sum            'C37 H30 N2 O5'
_chemical_formula_weight         582.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         C37H30N2O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   17.841(4)
_cell_length_b                   8.9458(16)
_cell_length_c                   18.773(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.309(15)
_cell_angle_gamma                90
_cell_volume                     2987.7(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6479
_cell_measurement_temperature    297.0(3)
_cell_measurement_theta_max      68.6580
_cell_measurement_theta_min      4.6830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58871
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 1 0 0.0196
-11 -1 0 0.0153
-3 2 11 0.1143
7 0 -10 0.0653
7 -1 -10 0.0552
1 -6 4 0.0798
-6 5 5 0.0161

_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.035
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
11.0022 1.0182 0.0198 -0.1796 -0.8205 0.4904
-11.0022 -1.0182 -0.0198 0.1796 0.8205 -0.4904
-2.9957 1.9488 11.0050 -0.1349 -0.3632 -0.9032
6.9955 0.0431 -9.9880 -0.1851 -0.0173 0.9679
6.9965 -0.9495 -9.9942 -0.0187 0.0028 0.9984
1.0087 -5.9640 3.9630 1.0679 -0.1490 -0.0240
-6.0033 4.9357 5.0216 -0.7365 0.0900 -0.7550

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            49427
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.39
_diffrn_reflns_theta_min         2.36
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9234
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -13.00   1.00    5.90    --  -41.49 -57.00  90.00  102
  2  ω   -116.00 -17.00   1.00    5.90    --  -41.49 -38.00 120.00   99
  3  ω    -96.00  -2.00   1.00    5.90    --  -41.49 125.00-180.00   94
  4  ω    -35.00  74.00   1.00    5.90    --   41.49 -77.00 -60.00  109
  5  ω     36.00 116.00   1.00   28.00    --  112.00-111.00 150.00   80
  6  ω     57.00 151.00   1.00   28.00    --  112.00 178.00   0.00   94
  7  ω     40.00 141.00   1.00   28.00    --  112.00 -61.00  90.00  101
  8  ω     86.00 178.00   1.00   28.00    --  112.00  45.00-150.00   92
  9  ω     86.00 178.00   1.00   28.00    --  112.00  45.00-180.00   92
 10  ω    100.00 178.00   1.00   28.00    --  112.00 111.00  60.00   78
 11  ω     36.00 116.00   1.00   28.00    --  112.00-111.00-180.00   80
 12  ω     29.00 109.00   1.00   28.00    --  112.00 -94.00-150.00   80
 13  ω     84.00 178.00   1.00   28.00    --  112.00  30.00 150.00   94
 14  ω     86.00 178.00   1.00   28.00    --  112.00  45.00-120.00   92
 15  ω     36.00 116.00   1.00   28.00    --  112.00-111.00 -30.00   80
 16  ω   -115.00 -34.00   1.00    5.90    --  -41.49 -57.00 -30.00   81
 17  ω     98.00 132.00   1.00   28.00    --  112.00 -77.00 120.00   34
 18  ω   -116.00 -17.00   1.00    9.00    --  -41.49 -38.00-150.00   99
 19  ω   -118.00  -9.00   1.00    9.00    --  -41.49 -77.00  26.00  109
 20  ω      1.00  82.00   1.00    9.00    --   41.49 -99.00  90.00   81
 21  ω      9.00  99.00   1.00    9.00    --   41.49  77.00 -90.00   90
 22  ω    153.00 178.00   1.00   28.00    --  112.00 111.00-150.00   25
 23  ω   -115.00 -13.00   1.00   10.00    --  -41.49 -57.00  30.00  102
 24  ω      9.00 118.00   1.00   10.00    --   41.49  77.00-180.00  109
 25  ω      9.00 118.00   1.00   10.00    --   41.49  77.00 120.00  109
 26  ω      1.00  82.00   1.00   10.00    --   41.49 -99.00   0.00   81
 27  ω      9.00 118.00   1.00   10.00    --   41.49  77.00  60.00  109
 28  ω      9.00 118.00   1.00   10.00    --   41.49  77.00 -60.00  109
 29  ω      9.00 118.00   1.00   10.00    --   41.49  77.00   0.00  109
 30  ω     17.00  58.00   1.00   10.00    --   41.49  38.00   0.00   41
 31  ω    -33.00  66.00   1.00   10.00    --   41.49 -38.00  90.00   99
 32  ω    149.00 175.00   1.00   28.00    --  112.00 111.00 -60.00   26
 33  ω    153.00 178.00   1.00   28.00    --  112.00  30.00 -90.00   25
 34  ω     17.00  42.00   1.00    8.64    --   50.00  79.00 130.39   25
 35  ω     20.00  45.00   1.00    8.64    --   54.00  81.00  17.27   25
 36  ω     21.00  46.00   1.00    8.64    --   54.00  79.00-177.41   25
 37  ω     20.00  45.00   1.00    8.64    --   54.00  81.00 -73.43   25
 38  ω     20.00  45.00   1.00    8.64    --   54.00  81.00-119.04   25
 39  ω     33.00  66.00   1.00    8.64    --   66.00  77.00 -46.53   33
 40  ω     34.00  59.00   1.00    8.64    --   66.00  76.00-121.99   25
 41  ω     34.00  60.00   1.00    8.64    --   66.00  76.00  13.20   26
 42  ω     34.00  64.00   1.00    8.64    --   66.00  76.00  95.10   30
 43  ω     34.00  60.00   1.00    8.64    --   66.00  75.00  54.99   26
 44  ω     33.00  59.00   1.00    8.64    --   66.00  77.00 -85.13   26
 45  ω     34.00  63.00   1.00    8.64    --   66.00  76.00 143.19   29
 46  ω     41.00  80.00   1.00    8.64    --   74.00  77.00 179.34   39
 47  ω    134.00 178.00   1.00   28.00    --  112.00  77.00   0.00   44
 48  ω     79.00 104.00   1.00   28.00    --  112.00  77.00  60.00   25
 49  ω     79.00 104.00   1.00   28.00    --  112.00  77.00   0.00   25
 50  ω    140.00 166.00   1.00   28.00    --  112.00  77.00 -90.00   26
 51  ω     79.00 104.00   1.00   28.00    --  112.00  77.00  30.00   25
 52  ω     54.00  85.00   1.00   28.00    --  112.00 -94.00  30.00   31
 53  ω     79.00 106.00   1.00   28.00    --  112.00  77.00 -90.00   27
 54  ω     79.00 111.00   1.00   28.00    --  112.00  77.00 120.00   32
 55  ω    144.00 171.00   1.00   28.00    --  112.00  77.00 -60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '/w scans with narrow frames'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0008284000
_diffrn_orient_matrix_UB_12      -0.1677588000
_diffrn_orient_matrix_UB_13      0.0172262000
_diffrn_orient_matrix_UB_21      -0.0726332000
_diffrn_orient_matrix_UB_22      -0.0200196000
_diffrn_orient_matrix_UB_23      -0.0492274000
_diffrn_orient_matrix_UB_31      0.0474948000
_diffrn_orient_matrix_UB_32      -0.0303170000
_diffrn_orient_matrix_UB_33      -0.0637713000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   
;
Advanced Light Source, station 11.3.1
;
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2556
_reflns_number_total             6241
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1821
_refine_ls_R_factor_gt           0.1176
_refine_ls_restrained_S_all      1.069
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3203
_refine_ls_wR_factor_ref         0.3937
_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,H) groups
2.a Rotating group:
 N15(H15a,H15b)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b), C36(H36a,H36b), C44(H44a,H44b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35), C39(H39), C40(H40), C41(H41), C42(H42), 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
O8 O 0.3201(2) 0.1980(4) 0.5661(2) 0.1078(12) Uani 1 1 d . . . . .
O20 O 0.39587(19) 0.3320(4) 0.64320(15) 0.0855(9) Uani 1 1 d . . . . .
O21 O 0.1190(2) 0.6014(4) 0.49432(16) 0.1000(11) Uani 1 1 d . . . . .
O29 O 0.1341(2) 0.8016(4) 0.59929(19) 0.1047(12) Uani 1 1 d . . . . .
O37 O 0.2438(2) 0.7821(4) 0.70300(17) 0.1001(11) Uani 1 1 d . . . . .
N11 N 0.4963(2) 0.2950(4) 0.53779(19) 0.0823(11) Uani 1 1 d . . . . .
N15 N 0.5434(3) 0.3742(5) 0.4330(2) 0.1049(14) Uani 1 1 d . . . . .
H15A H 0.4991 0.3806 0.4107 0.126 Uiso 1 1 d GR . . . .
H15B H 0.5752 0.3486 0.4024 0.126 Uiso 1 1 d GR . . . .
C1 C 0.1761(3) 0.5771(6) 0.5453(2) 0.0911(14) Uani 1 1 d . . . . .
C2 C 0.1840(3) 0.6845(6) 0.5985(2) 0.0877(14) Uani 1 1 d . . . . .
C3 C 0.2426(3) 0.6708(6) 0.6525(2) 0.0896(14) Uani 1 1 d . . . . .
C4 C 0.2909(3) 0.5494(5) 0.6538(2) 0.0865(13) Uani 1 1 d . . . . .
H4 H 0.3292 0.5398 0.6899 0.104 Uiso 1 1 calc R . . . .
C5 C 0.2813(3) 0.4424(5) 0.6005(2) 0.0846(13) Uani 1 1 d . . . . .
C6 C 0.2237(3) 0.4530(6) 0.5475(2) 0.0900(14) Uani 1 1 d . . . . .
H6 H 0.2166 0.3779 0.5134 0.108 Uiso 1 1 calc R . . . .
C7 C 0.3315(3) 0.3098(6) 0.6001(2) 0.0865(13) Uani 1 1 d . . . . .
C9 C 0.4978(3) 0.1953(5) 0.5924(2) 0.0779(12) Uani 1 1 d . . . . .
C10 C 0.5460(3) 0.0678(5) 0.5988(3) 0.0898(14) Uani 1 1 d . . . . .
C12 C 0.5418(3) 0.2699(6) 0.4866(2) 0.0899(14) Uani 1 1 d . . . . .
C13 C 0.5889(3) 0.1409(6) 0.4846(3) 0.0948(15) Uani 1 1 d . . . . .
H13 H 0.6169 0.1234 0.4456 0.114 Uiso 1 1 calc R . . . .
C14 C 0.5921(3) 0.0441(6) 0.5407(3) 0.0964(15) Uani 1 1 d . . . . .
H14 H 0.6243 -0.0377 0.5412 0.116 Uiso 1 1 calc R . . . .
C16 C 0.5472(4) -0.0230(6) 0.6593(3) 0.1027(17) Uani 1 1 d . . . . .
H16 H 0.5801 -0.1036 0.6634 0.123 Uiso 1 1 calc R . . . .
C17 C 0.5007(4) 0.0043(7) 0.7129(3) 0.1090(18) Uani 1 1 d . . . . .
H17 H 0.5029 -0.0564 0.7532 0.131 Uiso 1 1 calc R . . . .
C18 C 0.4500(3) 0.1238(6) 0.7066(3) 0.0953(15) Uani 1 1 d . . . . .
H18 H 0.4182 0.1424 0.7427 0.114 Uiso 1 1 calc R . . . .
C19 C 0.4474(3) 0.2131(5) 0.6473(2) 0.0854(13) Uani 1 1 d . . . . .
C22 C 0.0627(4) 0.5873(6) 0.3770(3) 0.0988(16) Uani 1 1 d . . . . .
C23 C -0.0122(5) 0.5992(9) 0.3879(3) 0.137(3) Uani 1 1 d . . . . .
H23 H -0.0297 0.5569 0.4287 0.164 Uiso 1 1 calc R . . . .
C24 C -0.0613(5) 0.6702(11) 0.3413(4) 0.149(3) Uani 1 1 d . . . . .
H24 H -0.1117 0.6746 0.3505 0.179 Uiso 1 1 calc R . . . .
C25 C -0.0389(6) 0.7344(9) 0.2821(4) 0.135(2) Uani 1 1 d . . . . .
H25 H -0.0731 0.7859 0.2513 0.162 Uiso 1 1 calc R . . . .
C26 C 0.0340(6) 0.7234(9) 0.2676(3) 0.139(3) Uani 1 1 d . . . . .
H26 H 0.0498 0.7652 0.2259 0.167 Uiso 1 1 calc R . . . .
C27 C 0.0858(5) 0.6498(9) 0.3149(3) 0.129(2) Uani 1 1 d . . . . .
H27 H 0.1358 0.6427 0.3046 0.155 Uiso 1 1 calc R . . . .
C28 C 0.1169(4) 0.5124(7) 0.4304(3) 0.1108(18) Uani 1 1 d . . . . .
H28A H 0.1002 0.4117 0.4400 0.133 Uiso 1 1 calc R . . . .
H28B H 0.1664 0.5072 0.4125 0.133 Uiso 1 1 calc R . . . .
C30 C 0.1497(4) 0.9817(7) 0.5057(4) 0.116(2) Uani 1 1 d . . . . .
C31 C 0.2014(6) 0.9250(9) 0.4597(5) 0.144(3) Uani 1 1 d . . . . .
H31 H 0.2444 0.8767 0.4790 0.173 Uiso 1 1 calc R . . . .
C32 C 0.1897(8) 0.9397(12) 0.3845(6) 0.186(5) Uani 1 1 d . . . . .
H32 H 0.2217 0.8983 0.3530 0.224 Uiso 1 1 calc R . . . .
C33 C 0.1243(9) 1.0239(15) 0.3617(7) 0.200(6) Uani 1 1 d . . . . .
H33 H 0.1145 1.0384 0.3128 0.240 Uiso 1 1 calc R . . . .
C34 C 0.0768(8) 1.0827(13) 0.4040(6) 0.175(5) Uani 1 1 d . . . . .
H34 H 0.0356 1.1378 0.3855 0.210 Uiso 1 1 calc R . . . .
C35 C 0.0897(5) 1.0605(9) 0.4763(5) 0.156(3) Uani 1 1 d . . . . .
H35 H 0.0561 1.1011 0.5065 0.187 Uiso 1 1 calc R . . . .
C36 C 0.1623(4) 0.9471(7) 0.5821(3) 0.126(2) Uani 1 1 d . . . . .
H36A H 0.2157 0.9513 0.5959 0.151 Uiso 1 1 calc R . . . .
H36B H 0.1376 1.0222 0.6094 0.151 Uiso 1 1 calc R . . . .
C38 C 0.3040(3) 0.9394(6) 0.7915(2) 0.0898(14) Uani 1 1 d . . . . .
C39 C 0.3411(3) 0.9480(7) 0.8572(3) 0.1015(16) Uani 1 1 d . . . . .
H39 H 0.3695 0.8669 0.8745 0.122 Uiso 1 1 calc R . . . .
C40 C 0.3375(4) 1.0751(7) 0.8991(3) 0.1106(18) Uani 1 1 d . . . . .
H40 H 0.3643 1.0794 0.9435 0.133 Uiso 1 1 calc R . . . .
C41 C 0.2950(4) 1.1926(7) 0.8755(3) 0.1100(18) Uani 1 1 d . . . . .
H41 H 0.2908 1.2762 0.9043 0.132 Uiso 1 1 calc R . . . .
C42 C 0.2577(4) 1.1881(6) 0.8080(3) 0.1119(19) Uani 1 1 d . . . . .
H42 H 0.2300 1.2703 0.7908 0.134 Uiso 1 1 calc R . . . .
C43 C 0.2617(4) 1.0619(7) 0.7666(3) 0.1085(18) Uani 1 1 d . . . . .
H43 H 0.2359 1.0584 0.7216 0.130 Uiso 1 1 calc R . . . .
C44 C 0.3110(3) 0.8008(6) 0.7469(3) 0.1019(17) Uani 1 1 d . . . . .
H44A H 0.3532 0.8106 0.7176 0.122 Uiso 1 1 calc R . . . .
H44B H 0.3195 0.7144 0.7776 0.122 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
O8 C7 1.196(5) . ?
O20 C7 1.368(6) . ?
O20 C19 1.404(6) . ?
O21 C1 1.362(6) . ?
O21 C28 1.438(6) . ?
O29 C2 1.376(6) . ?
O29 C36 1.440(8) . ?
O37 C3 1.374(5) . ?
O37 C44 1.412(6) . ?
N11 C9 1.358(5) . ?
N11 C12 1.323(6) . ?
N15 H15A 0.8678 . ?
N15 H15B 0.8675 . ?
N15 C12 1.375(6) . ?
C1 C2 1.385(6) . ?
C1 C6 1.397(7) . ?
C2 C3 1.405(7) . ?
C3 C4 1.386(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(6) . ?
C5 C6 1.378(7) . ?
C5 C7 1.487(7) . ?
C6 H6 0.9300 . ?
C9 C10 1.428(7) . ?
C9 C19 1.427(7) . ?
C10 C14 1.430(8) . ?
C10 C16 1.395(7) . ?
C12 C13 1.429(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.361(7) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.373(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.399(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(6) . ?
C22 C23 1.370(9) . ?
C22 C27 1.383(8) . ?
C22 C28 1.498(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.349(9) . ?
C24 H24 0.9300 . ?
C24 C25 1.338(10) . ?
C25 H25 0.9300 . ?
C25 C26 1.353(10) . ?
C26 H26 0.9300 . ?
C26 C27 1.397(10) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C30 C31 1.405(11) . ?
C30 C35 1.362(10) . ?
C30 C36 1.469(9) . ?
C31 H31 0.9300 . ?
C31 C32 1.417(12) . ?
C32 H32 0.9300 . ?
C32 C33 1.428(16) . ?
C33 H33 0.9300 . ?
C33 C34 1.314(16) . ?
C34 H34 0.9300 . ?
C34 C35 1.374(12) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C38 C39 1.357(7) . ?
C38 C43 1.392(7) . ?
C38 C44 1.506(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.386(8) . ?
C40 H40 0.9300 . ?
C40 C41 1.351(8) . ?
C41 H41 0.9300 . ?
C41 C42 1.386(8) . ?
C42 H42 0.9300 . ?
C42 C43 1.376(7) . ?
C43 H43 0.9300 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O20 C19 116.1(4) . . ?
C1 O21 C28 118.0(4) . . ?
C2 O29 C36 116.6(5) . . ?
C3 O37 C44 117.2(4) . . ?
C12 N11 C9 117.3(4) . . ?
H15A N15 H15B 108.5 . . ?
C12 N15 H15A 109.2 . . ?
C12 N15 H15B 110.8 . . ?
O21 C1 C2 115.3(4) . . ?
O21 C1 C6 124.6(4) . . ?
C2 C1 C6 120.1(5) . . ?
O29 C2 C1 120.3(4) . . ?
O29 C2 C3 120.4(4) . . ?
C1 C2 C3 119.3(5) . . ?
O37 C3 C2 114.0(5) . . ?
O37 C3 C4 125.3(4) . . ?
C4 C3 C2 120.6(4) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(5) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C7 120.8(4) . . ?
C6 C5 C4 121.3(5) . . ?
C6 C5 C7 117.9(4) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
O8 C7 O20 122.5(5) . . ?
O8 C7 C5 126.3(5) . . ?
O20 C7 C5 111.2(4) . . ?
N11 C9 C10 124.4(5) . . ?
N11 C9 C19 119.7(4) . . ?
C19 C9 C10 115.9(4) . . ?
C9 C10 C14 115.6(5) . . ?
C16 C10 C9 120.3(5) . . ?
C16 C10 C14 124.1(5) . . ?
N11 C12 N15 117.7(5) . . ?
N11 C12 C13 123.4(5) . . ?
N15 C12 C13 119.0(5) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 H13 120.5 . . ?
C10 C14 H14 119.9 . . ?
C13 C14 C10 120.1(5) . . ?
C13 C14 H14 119.9 . . ?
C10 C16 H16 119.3 . . ?
C17 C16 C10 121.4(5) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.7(5) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 H18 120.1 . . ?
O20 C19 C9 119.3(4) . . ?
C18 C19 O20 118.1(5) . . ?
C18 C19 C9 122.5(5) . . ?
C23 C22 C27 116.7(6) . . ?
C23 C22 C28 121.5(6) . . ?
C27 C22 C28 121.8(6) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 C22 122.2(7) . . ?
C24 C23 H23 118.9 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.4(8) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 120.4 . . ?
C24 C25 C26 119.2(7) . . ?
C26 C25 H25 120.4 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.3(7) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 120.2(7) . . ?
C22 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
O21 C28 C22 106.6(4) . . ?
O21 C28 H28A 110.4 . . ?
O21 C28 H28B 110.4 . . ?
C22 C28 H28A 110.4 . . ?
C22 C28 H28B 110.4 . . ?
H28A C28 H28B 108.6 . . ?
C31 C30 C36 117.7(7) . . ?
C35 C30 C31 118.0(8) . . ?
C35 C30 C36 124.2(9) . . ?
C30 C31 H31 119.2 . . ?
C30 C31 C32 121.6(10) . . ?
C32 C31 H31 119.2 . . ?
C31 C32 H32 123.1 . . ?
C31 C32 C33 113.8(11) . . ?
C33 C32 H32 123.1 . . ?
C32 C33 H33 117.3 . . ?
C34 C33 C32 125.4(13) . . ?
C34 C33 H33 117.3 . . ?
C33 C34 H34 120.9 . . ?
C33 C34 C35 118.1(13) . . ?
C35 C34 H34 120.9 . . ?
C30 C35 C34 122.9(11) . . ?
C30 C35 H35 118.5 . . ?
C34 C35 H35 118.5 . . ?
O29 C36 C30 112.3(5) . . ?
O29 C36 H36A 109.2 . . ?
O29 C36 H36B 109.2 . . ?
C30 C36 H36A 109.2 . . ?
C30 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
C39 C38 C43 118.4(5) . . ?
C39 C38 C44 119.8(5) . . ?
C43 C38 C44 121.7(4) . . ?
C38 C39 H39 119.3 . . ?
C38 C39 C40 121.5(6) . . ?
C40 C39 H39 119.3 . . ?
C39 C40 H40 120.0 . . ?
C41 C40 C39 120.0(5) . . ?
C41 C40 H40 120.0 . . ?
C40 C41 H41 120.1 . . ?
C40 C41 C42 119.7(5) . . ?
C42 C41 H41 120.1 . . ?
C41 C42 H42 120.0 . . ?
C43 C42 C41 119.9(6) . . ?
C43 C42 H42 120.0 . . ?
C38 C43 H43 119.8 . . ?
C42 C43 C38 120.3(5) . . ?
C42 C43 H43 119.8 . . ?
O37 C44 C38 108.7(4) . . ?
O37 C44 H44A 109.9 . . ?
O37 C44 H44B 109.9 . . ?
C38 C44 H44A 109.9 . . ?
C38 C44 H44B 109.9 . . ?
H44A C44 H44B 108.3 . . ?

_shelx_SHELXL_version_number     2014/7

_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 5.190
_oxdiff_exptl_absorpt_empirical_full_min 0.328
####################################################################### 
# 
# 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_exp_588
_database_code_depnum_ccdc_archive 'CCDC 1548394'
_audit_update_record             
;
2017-05-07 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;
_audit_creation_date             2016-12-07
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        4b
_chemical_formula_moiety         'C16 H11 Cl N2 O2'
_chemical_formula_sum            'C16 H11 Cl N2 O2'
_chemical_formula_weight         298.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H11ClN2O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   23.1622(3)
_cell_length_b                   3.82800(10)
_cell_length_c                   31.4881(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.6800(10)
_cell_angle_gamma                90
_cell_volume                     2752.14(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14387
_cell_measurement_temperature    293.3(3)
_cell_measurement_theta_max      76.3830
_cell_measurement_theta_min      2.8410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 -20 0.0343
-4 0 20 0.0532
-2 2 0 0.0665
15 0 -7 0.0456
0 -2 1 0.0800
-15 0 7 0.0691

_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.092
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
3.5966 0.0791 -20.3757 0.0254 0.9986 0.0462
-3.6713 0.0582 20.3723 -0.0254 -0.9996 0.0093
-1.5553 2.4702 -0.3184 -0.0172 -0.0067 0.9998
14.8046 0.0649 -6.8521 0.9224 0.3829 -0.0517
0.0787 -2.4817 1.0039 -0.0750 -0.0316 -0.9967
-14.7858 0.1741 6.7433 -0.9135 -0.3791 0.1476

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            25095
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.61
_diffrn_reflns_theta_min         2.20
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.3(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -30.00   1.00    1.10    --  -41.49 -38.00 -60.00   76
  2  ω   -112.00 -17.00   1.00    1.10    --  -41.49 -38.00-150.00   95
  3  ω     18.00  44.00   1.00    1.10    --   41.49  38.00 -90.00   26
  4  ω     68.00  95.00   1.00    1.10    --   41.49-129.00-114.00   27
  5  ω     41.00  94.00   1.00    5.00    --  112.00 -94.00   0.00   53
  6  ω     86.00 166.00   1.00    5.00    --  112.00  45.00 -30.00   80
  7  ω     76.00 114.00   1.00    5.00    --  112.00 -30.00 120.00   38
  8  ω     48.00 145.00   1.00    5.00    --  112.00 -77.00  60.00   97
  9  ω    147.00 173.00   1.00    5.00    --  112.00  30.00-120.00   26
 10  ω    103.00 130.00   1.00    5.00    --  112.00 111.00-120.00   27
 11  ω     86.00 178.00   1.00    5.00    --  112.00  45.00-150.00   92
 12  ω     93.00 178.00   1.00    5.00    --  112.00  30.00 -60.00   85
 13  ω     37.00  91.00   1.00    5.00    --  112.00 -77.00  30.00   54
 14  ω    -87.00 -50.00   1.00    1.10    --  -41.49 -57.00   0.00   37
 15  ω    -38.00 -13.00   1.00    1.10    --  -41.49 -57.00   0.00   25
 16  ω      1.00  62.00   1.00    1.10    --   41.49 -99.00-180.00   61
 17  ω      7.00  34.00   1.00    1.10    --   41.49  87.00 173.01   27
 18  ω    -31.00  66.00   1.00    1.10    --   41.49 -38.00-150.00   97
 19  ω     42.00  74.00   1.00    1.10    --   41.49-140.00  72.00   32
 20  ω     38.00  64.00   1.00    1.10    --   41.49-125.00 120.00   26
 21  ω     13.00  40.00   1.00    1.10    --   46.00  83.00   5.01   27
 22  ω     17.00  49.00   1.00    1.10    --   50.00  78.00  56.45   32
 23  ω     18.00  46.00   1.00    1.10    --   50.00  80.00 -48.20   28
 24  ω     76.00 125.00   1.00    1.10    --   54.00  77.00 121.44   49
 25  ω     21.00  63.00   1.00    1.10    --   54.00  77.00-101.08   42
 26  ω     21.00  58.00   1.00    1.10    --   54.00  77.00 121.44   37
 27  ω    105.00 130.00   1.00    1.10    --   54.00  77.00-101.08   25
 28  ω     27.00  59.00   1.00    1.10    --   58.00  76.00 162.68   32
 29  ω     31.00  61.00   1.00    1.10    --   58.00  76.00-154.04   30
 30  ω    102.00 127.00   1.00    1.10    --   58.00  76.00-154.04   25
 31  ω    100.00 125.00   1.00    1.10    --   58.00  76.00 162.68   25
 32  ω     37.00  63.00   1.00    1.10    --   62.00  34.00  60.77   26
 33  ω     38.00  77.00   1.00    1.10    --   66.00  57.00  67.81   39
 34  ω     57.00 101.00   1.00    5.00    --  112.00-111.00 -90.00   44
 35  ω     80.00 107.00   1.00    5.00    --  112.00  77.00  30.00   27
 36  ω     79.00 105.00   1.00    5.00    --  112.00  77.00 120.00   26
 37  ω    141.00 172.00   1.00    5.00    --  112.00  77.00 -30.00   31
 38  ω     83.00 109.00   1.00    5.00    --  112.00  61.00-150.00   26
 39  ω     79.00 132.00   1.00    5.00    --  112.00  77.00 -30.00   53
 40  ω    111.00 138.00   1.00    5.00    --  112.00 -61.00  90.00   27
 41  ω    119.00 177.00   1.00    5.00    --  112.00  77.00  30.00   58
 42  ω     80.00 105.00   1.00    5.00    --  112.00  77.00-150.00   25
 43  ω    151.00 176.00   1.00    5.00    --  112.00  77.00-150.00   25
 44  ω     79.00 105.00   1.00    5.00    --  112.00  77.00 -90.00   26
 45  ω    143.00 176.00   1.00    5.00    --  112.00  61.00-180.00   33
 46  ω     83.00 113.00   1.00    5.00    --  112.00  61.00-180.00   30
 47  ω    133.00 174.00   1.00    5.00    --  112.00  77.00  90.00   41
 48  ω     79.00 106.00   1.00    5.00    --  112.00  77.00  90.00   27
 49  ω     84.00 109.00   1.00    5.00    --  112.00  61.00 -30.00   25
 50  ω     79.00 147.00   1.00    5.00    --  112.00  77.00   0.00   68
 51  ω    152.00 178.00   1.00    5.00    --  112.00  61.00-120.00   26
 52  ω     54.00 140.00   1.00    5.00    --  112.00 -61.00-120.00   86
 53  ω     84.00 109.00   1.00    5.00    --  112.00  61.00 -60.00   25
 54  ω     83.00 125.00   1.00    5.00    --  112.00  61.00-120.00   42
 55  ω     83.00 178.00   1.00    5.00    --  112.00  61.00 150.00   95
 56  ω     80.00 105.00   1.00    5.00    --  112.00  77.00-180.00   25
 57  ω     86.00 151.00   1.00    5.00    --  112.00  61.00  90.00   65
 58  ω     83.00 122.00   1.00    5.00    --  112.00  61.00 120.00   39
 59  ω    129.00 178.00   1.00    5.00    --  112.00  61.00 120.00   49
 60  ω    115.00 175.00   1.00    5.00    --  112.00  77.00  60.00   60
 61  ω     79.00 105.00   1.00    5.00    --  112.00  77.00 150.00   26
 62  ω     84.00 110.00   1.00    5.00    --  112.00  61.00 -90.00   26
 63  ω    148.00 177.00   1.00    5.00    --  112.00  61.00 -90.00   29
 64  ω     80.00 105.00   1.00    5.00    --  112.00  77.00  60.00   25
 65  ω     79.00 105.00   1.00    5.00    --  112.00  77.00 -60.00   26
 66  ω    149.00 175.00   1.00    5.00    --  112.00  77.00 -60.00   26
 67  ω     45.00  71.00   1.00    5.00    --  112.00 -61.00  90.00   26
 68  ω     79.00 108.00   1.00    5.00    --  112.00  77.00-120.00   29
 69  ω     43.00  69.00   1.00    5.00    --  112.00-111.00-180.00   26
 70  ω     89.00 115.00   1.00    5.00    --  112.00-111.00-180.00   26
 71  ω     83.00 126.00   1.00    5.00    --  112.00  61.00  60.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0671134000
_diffrn_orient_matrix_UB_12      0.0366808000
_diffrn_orient_matrix_UB_13      0.0107427000
_diffrn_orient_matrix_UB_21      0.0034786000
_diffrn_orient_matrix_UB_22      -0.0067493000
_diffrn_orient_matrix_UB_23      -0.0484222000
_diffrn_orient_matrix_UB_31      -0.0060777000
_diffrn_orient_matrix_UB_32      0.4006932000
_diffrn_orient_matrix_UB_33      -0.0017826000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2753
_reflns_number_total             2882
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00166(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+1.9139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C9(H9), C10(H10), C13(H13), C15(H15), C16(H16)
2.b Idealised tetrahedral OH refined as rotating group:
 O12(H12)
;
_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
Cl19 Cl 0.38880(3) 0.77202(18) 0.77104(2) 0.0901(3) Uani 1 1 d . . . . .
O12 O 0.23017(4) 0.1779(4) 0.43970(4) 0.0534(3) Uani 1 1 d . . . . .
H12 H 0.2359 0.2439 0.4648 0.080 Uiso 1 1 calc GR . . . .
O21 O 0.46522(6) 0.9051(5) 0.57804(5) 0.0827(5) Uani 1 1 d . . . . .
N7 N 0.33011(5) 0.4631(3) 0.48889(4) 0.0397(3) Uani 1 1 d . . . . .
N11 N 0.37751(5) 0.6458(4) 0.55492(4) 0.0463(3) Uani 1 1 d . . . . .
H11 H 0.3470(10) 0.569(6) 0.5634(7) 0.073(6) Uiso 1 1 d . . . . .
C1 C 0.32502(8) 0.2409(5) 0.35855(6) 0.0541(4) Uani 1 1 d . . . . .
H1 H 0.3234 0.1848 0.3296 0.065 Uiso 1 1 calc R . . . .
C2 C 0.27681(7) 0.1693(4) 0.37901(5) 0.0496(4) Uani 1 1 d . . . . .
H2 H 0.2434 0.0670 0.3634 0.060 Uiso 1 1 calc R . . . .
C3 C 0.27854(6) 0.2482(4) 0.42147(5) 0.0428(3) Uani 1 1 d . . . . .
C4 C 0.32935(6) 0.3995(4) 0.44611(5) 0.0390(3) Uani 1 1 d . . . . .
C5 C 0.37725(6) 0.4741(4) 0.42475(5) 0.0437(3) Uani 1 1 d . . . . .
C6 C 0.37396(7) 0.3915(5) 0.38087(6) 0.0529(4) Uani 1 1 d . . . . .
H6 H 0.4055 0.4405 0.3671 0.063 Uiso 1 1 calc R . . . .
C8 C 0.37832(6) 0.6018(4) 0.51095(5) 0.0400(3) Uani 1 1 d . . . . .
C9 C 0.42778(6) 0.6950(4) 0.49225(6) 0.0476(4) Uani 1 1 d . . . . .
H9 H 0.4604 0.7980 0.5088 0.057 Uiso 1 1 calc R . . . .
C10 C 0.42652(6) 0.6308(5) 0.44983(6) 0.0500(4) Uani 1 1 d . . . . .
H10 H 0.4586 0.6909 0.4371 0.060 Uiso 1 1 calc R . . . .
C13 C 0.35211(8) 0.6355(5) 0.68663(6) 0.0569(4) Uani 1 1 d . . . . .
H13 H 0.3181 0.5479 0.6948 0.068 Uiso 1 1 calc R . . . .
C14 C 0.39647(9) 0.7678(5) 0.71721(6) 0.0585(5) Uani 1 1 d . . . . .
C15 C 0.44710(9) 0.8966(5) 0.70564(6) 0.0619(5) Uani 1 1 d . . . . .
H15 H 0.4769 0.9836 0.7265 0.074 Uiso 1 1 calc R . . . .
C16 C 0.45324(7) 0.8956(5) 0.66299(6) 0.0554(4) Uani 1 1 d . . . . .
H16 H 0.4874 0.9829 0.6551 0.066 Uiso 1 1 calc R . . . .
C17 C 0.40905(6) 0.7658(4) 0.63128(5) 0.0445(4) Uani 1 1 d . . . . .
C18 C 0.35869(7) 0.6346(5) 0.64391(5) 0.0500(4) Uani 1 1 d . . . . .
H18 H 0.3280(9) 0.533(6) 0.6238(7) 0.066(6) Uiso 1 1 d . . . . .
C20 C 0.42011(6) 0.7791(4) 0.58583(5) 0.0473(4) 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
Cl19 C14 1.7337(19) . ?
O12 H12 0.8200 . ?
O12 C3 1.3686(19) . ?
O21 C20 1.213(2) . ?
N7 C4 1.3660(18) . ?
N7 C8 1.3231(18) . ?
N11 H11 0.85(2) . ?
N11 C8 1.398(2) . ?
N11 C20 1.363(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.407(2) . ?
C1 C6 1.358(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(2) . ?
C3 C4 1.420(2) . ?
C4 C5 1.4196(19) . ?
C5 C6 1.407(2) . ?
C5 C10 1.408(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.419(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.354(2) . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.381(3) . ?
C13 C18 1.379(2) . ?
C14 C15 1.377(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.396(2) . ?
C17 C18 1.388(2) . ?
C17 C20 1.497(2) . ?
C18 H18 0.95(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
C3 O12 H12 109.5 . . ?
C8 N7 C4 117.33(12) . . ?
C8 N11 H11 114.9(15) . . ?
C20 N11 H11 116.4(15) . . ?
C20 N11 C8 128.59(13) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.24(16) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.72(15) . . ?
C3 C2 H2 119.6 . . ?
O12 C3 C4 120.86(14) . . ?
C2 C3 O12 118.43(14) . . ?
C2 C3 C4 120.71(14) . . ?
N7 C4 C3 118.92(12) . . ?
N7 C4 C5 123.35(13) . . ?
C5 C4 C3 117.73(14) . . ?
C6 C5 C4 120.16(14) . . ?
C6 C5 C10 123.46(14) . . ?
C10 C5 C4 116.38(14) . . ?
C1 C6 C5 120.42(15) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N7 C8 N11 114.71(12) . . ?
N7 C8 C9 123.50(14) . . ?
N11 C8 C9 121.79(13) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.62(14) . . ?
C10 C9 H9 120.7 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.76(13) . . ?
C9 C10 H10 119.6 . . ?
C14 C13 H13 120.3 . . ?
C18 C13 H13 120.3 . . ?
C18 C13 C14 119.34(17) . . ?
C13 C14 Cl19 119.91(16) . . ?
C15 C14 Cl19 119.17(15) . . ?
C15 C14 C13 120.91(17) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.38(16) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.09(17) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C20 116.70(15) . . ?
C18 C17 C16 118.31(16) . . ?
C18 C17 C20 125.00(14) . . ?
C13 C18 C17 120.97(15) . . ?
C13 C18 H18 117.3(13) . . ?
C17 C18 H18 121.7(13) . . ?
O21 C20 N11 123.33(16) . . ?
O21 C20 C17 119.91(15) . . ?
N11 C20 C17 116.77(13) . . ?

_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 0.250 -0.239 0.750 39.9 3.8 ?
2 0.250 -0.646 0.250 39.9 3.8 ?
3 0.750 -0.739 0.250 39.9 3.8 ?
4 0.750 -0.146 0.750 39.9 3.8 ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-06
_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 1.197
_oxdiff_exptl_absorpt_empirical_full_min 0.863
