# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ecv1_93_a
_database_code_depnum_ccdc_archive 'CCDC 2003343'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2016-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   10.7032(5)
_cell_length_b                   6.6627(3)
_cell_length_c                   16.9382(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.303(2)
_cell_angle_gamma                90
_cell_volume                     1206.92(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.030
_cell_measurement_theta_min      2.407
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.7240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1229 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.9722.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            56388
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        30.180
_diffrn_reflns_theta_max         30.180
_diffrn_reflns_theta_min         2.211
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2970
_reflns_number_total             3575
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.5302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{C10A, C10B}
{C11A, C15B}
{C12A, C14B}
{C13A, C13B}
{C14A, C12B}
{C15A, C11B}
3. Restrained distances
 O3A-H3A \\sim O3B-H3B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C15B)
Uanis(C12A) = Uanis(C14B)
Uanis(C13A) = Uanis(C13B)
Uanis(C14A) = Uanis(C12B)
Uanis(C15A) = Uanis(C11B)
5. Others
 Sof(O3B)=Sof(H3B)=Sof(C10B)=Sof(C11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=
 Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=1-FVAR(1)
 Sof(O3A)=Sof(H3A)=Sof(C10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
6.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C12B(H12B),
 C13B(H13B), C14B(H14B), C15B(H15B)
;
_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
O1 O 0.48407(8) 0.79289(12) 0.10722(5) 0.02226(19) Uani 1 1 d . . . . .
O2 O 0.78191(8) 0.37964(14) 0.21693(5) 0.0249(2) Uani 1 1 d . . . . .
N1 N 0.61400(8) 0.56729(13) 0.17245(5) 0.01454(18) Uani 1 1 d . . . . .
C1 C 0.87514(11) 0.77789(18) 0.00799(7) 0.0223(2) Uani 1 1 d . . . . .
H1A H 0.909888 0.755616 -0.044592 0.027 Uiso 1 1 calc R . . . .
H1B H 0.915071 0.896027 0.033923 0.027 Uiso 1 1 calc R . . . .
C2 C 0.73087(11) 0.78915(18) 0.00501(6) 0.0201(2) Uani 1 1 d . . . . .
H2 H 0.692287 0.895257 -0.029885 0.024 Uiso 1 1 calc R . . . .
C3 C 0.71083(10) 0.81171(16) 0.09576(6) 0.0165(2) Uani 1 1 d . . . . .
H3 H 0.724034 0.953767 0.113232 0.020 Uiso 1 1 calc R . . . .
C4 C 0.58845(10) 0.73163(15) 0.12342(6) 0.0156(2) Uani 1 1 d . . . . .
C5 C 0.74062(10) 0.52143(17) 0.17918(6) 0.0163(2) Uani 1 1 d . . . . .
C6 C 0.81179(9) 0.67302(16) 0.13323(6) 0.0160(2) Uani 1 1 d . . . . .
H6 H 0.870854 0.750464 0.168893 0.019 Uiso 1 1 calc R . . . .
C7 C 0.88050(11) 0.58857(18) 0.06046(6) 0.0199(2) Uani 1 1 d . . . . .
H7 H 0.965345 0.529896 0.071725 0.024 Uiso 1 1 calc R . . . .
C8 C 0.78767(12) 0.45632(18) 0.01553(6) 0.0234(2) Uani 1 1 d . . . . .
H8 H 0.791909 0.314366 0.011106 0.028 Uiso 1 1 calc R . . . .
C9 C 0.69900(12) 0.57354(19) -0.01673(6) 0.0234(2) Uani 1 1 d . . . . .
H9 H 0.628277 0.530115 -0.047854 0.028 Uiso 1 1 calc R . . . .
O3A O 0.49847(12) 0.70468(18) 0.31354(7) 0.0226(3) Uani 0.685(3) 1 d D . P A 1
H3A H 0.566(2) 0.751(4) 0.2958(15) 0.037(7) Uiso 0.685(3) 1 d D . P A 1
C10A C 0.52092(9) 0.45400(16) 0.21146(6) 0.0145(2) Uani 0.685(3) 1 d . . P A 1
C11A C 0.46902(10) 0.52968(17) 0.27967(6) 0.0177(2) Uani 0.685(3) 1 d . . P A 1
C12A C 0.38214(10) 0.41338(19) 0.31827(6) 0.0211(2) Uani 0.685(3) 1 d . . P A 1
H12A H 0.345229 0.463785 0.364335 0.025 Uiso 0.685(3) 1 calc R . P A 1
C13A C 0.34923(10) 0.22508(19) 0.29002(7) 0.0223(2) Uani 0.685(3) 1 d . . P A 1
H13A H 0.289960 0.147114 0.316887 0.027 Uiso 0.685(3) 1 calc R . P A 1
C14A C 0.40211(10) 0.14908(18) 0.22271(7) 0.0209(2) Uani 0.685(3) 1 d . . P A 1
H14A H 0.379882 0.019149 0.203802 0.025 Uiso 0.685(3) 1 calc R . P A 1
C15A C 0.48779(10) 0.26467(17) 0.18327(6) 0.0167(2) Uani 0.685(3) 1 d . . P A 1
H15A H 0.523823 0.214179 0.136920 0.020 Uiso 0.685(3) 1 calc R . P A 1
O3B O 0.5348(2) 0.2044(4) 0.11611(14) 0.0188(7) Uani 0.315(3) 1 d D . P A 2
H3B H 0.508(6) 0.086(6) 0.105(4) 0.06(2) Uiso 0.315(3) 1 d D . P A 2
C10B C 0.52092(9) 0.45400(16) 0.21146(6) 0.0145(2) Uani 0.315(3) 1 d . . P A 2
C11B C 0.48779(10) 0.26467(17) 0.18327(6) 0.0167(2) Uani 0.315(3) 1 d . . P A 2
C12B C 0.40211(10) 0.14908(18) 0.22271(7) 0.0209(2) Uani 0.315(3) 1 d . . P A 2
H12B H 0.379882 0.019149 0.203802 0.025 Uiso 0.315(3) 1 calc R . P A 2
C13B C 0.34923(10) 0.22508(19) 0.29002(7) 0.0223(2) Uani 0.315(3) 1 d . . P A 2
H13B H 0.289960 0.147114 0.316887 0.027 Uiso 0.315(3) 1 calc R . P A 2
C14B C 0.38214(10) 0.41338(19) 0.31827(6) 0.0211(2) Uani 0.315(3) 1 d . . P A 2
H14B H 0.345229 0.463785 0.364335 0.025 Uiso 0.315(3) 1 calc R . P A 2
C15B C 0.46902(10) 0.52968(17) 0.27967(6) 0.0177(2) Uani 0.315(3) 1 d . . P A 2
H15B H 0.492528 0.658271 0.299419 0.021 Uiso 0.315(3) 1 calc R . P A 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
O1 C4 1.2105(13) . ?
O2 C5 1.2140(14) . ?
N1 C4 1.3947(14) . ?
N1 C5 1.3894(13) . ?
N1 C10A 1.4323(13) . ?
N1 C10B 1.4323(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5448(16) . ?
C1 C7 1.5428(16) . ?
C2 H2 1.0000 . ?
C2 C3 1.5679(15) . ?
C2 C9 1.5184(17) . ?
C3 H3 1.0000 . ?
C3 C4 1.5063(15) . ?
C3 C6 1.5393(15) . ?
C5 C6 1.5013(15) . ?
C6 H6 1.0000 . ?
C6 C7 1.5652(14) . ?
C7 H7 1.0000 . ?
C7 C8 1.5106(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3295(18) . ?
C9 H9 0.9500 . ?
O3A H3A 0.85(3) . ?
O3A C11A 1.3317(16) . ?
C10A C11A 1.3961(14) . ?
C10A C15A 1.3898(15) . ?
C11A C12A 1.3934(15) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.3833(17) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.3887(16) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.3892(15) . ?
C15A H15A 0.9500 . ?
O3B H3B 0.86(3) . ?
O3B C11B 1.324(3) . ?
C10B C11B 1.3898(15) . ?
C10B C15B 1.3961(14) . ?
C11B C12B 1.3892(15) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.3887(16) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.3833(17) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.3934(15) . ?
C15B H15B 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
C4 N1 C10A 124.40(9) . . ?
C4 N1 C10B 124.40(9) . . ?
C5 N1 C4 112.88(8) . . ?
C5 N1 C10A 122.72(9) . . ?
C5 N1 C10B 122.72(9) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.9 . . ?
C2 C1 H1B 112.9 . . ?
C7 C1 H1A 112.9 . . ?
C7 C1 H1B 112.9 . . ?
C7 C1 C2 94.16(8) . . ?
C1 C2 H2 116.2 . . ?
C1 C2 C3 98.54(9) . . ?
C3 C2 H2 116.2 . . ?
C9 C2 C1 100.17(9) . . ?
C9 C2 H2 116.2 . . ?
C9 C2 C3 106.87(9) . . ?
C2 C3 H3 111.0 . . ?
C4 C3 C2 115.21(9) . . ?
C4 C3 H3 111.0 . . ?
C4 C3 C6 105.30(8) . . ?
C6 C3 C2 103.02(8) . . ?
C6 C3 H3 111.0 . . ?
O1 C4 N1 123.83(10) . . ?
O1 C4 C3 128.04(10) . . ?
N1 C4 C3 108.13(9) . . ?
O2 C5 N1 123.20(10) . . ?
O2 C5 C6 127.95(10) . . ?
N1 C5 C6 108.85(9) . . ?
C3 C6 H6 110.8 . . ?
C3 C6 C7 103.61(8) . . ?
C5 C6 C3 104.78(8) . . ?
C5 C6 H6 110.8 . . ?
C5 C6 C7 115.51(9) . . ?
C7 C6 H6 110.8 . . ?
C1 C7 C6 98.74(9) . . ?
C1 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
C8 C7 C1 100.27(9) . . ?
C8 C7 C6 106.63(9) . . ?
C8 C7 H7 116.2 . . ?
C7 C8 H8 126.0 . . ?
C9 C8 C7 107.98(10) . . ?
C9 C8 H8 126.0 . . ?
C2 C9 H9 126.1 . . ?
C8 C9 C2 107.84(10) . . ?
C8 C9 H9 126.1 . . ?
C11A O3A H3A 110.8(17) . . ?
C11A C10A N1 119.91(9) . . ?
C15A C10A N1 119.50(9) . . ?
C15A C10A C11A 120.51(10) . . ?
O3A C11A C10A 125.28(11) . . ?
O3A C11A C12A 115.82(10) . . ?
C12A C11A C10A 118.86(10) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.50(10) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C12A C13A C14A 120.54(10) . . ?
C14A C13A H13A 119.7 . . ?
C13A C14A H14A 120.3 . . ?
C13A C14A C15A 119.44(11) . . ?
C15A C14A H14A 120.3 . . ?
C10A C15A H15A 119.9 . . ?
C14A C15A C10A 120.15(10) . . ?
C14A C15A H15A 119.9 . . ?
C11B O3B H3B 109(4) . . ?
C11B C10B N1 119.50(9) . . ?
C11B C10B C15B 120.51(10) . . ?
C15B C10B N1 119.91(9) . . ?
O3B C11B C10B 118.02(14) . . ?
O3B C11B C12B 121.72(15) . . ?
C12B C11B C10B 120.15(10) . . ?
C11B C12B H12B 120.3 . . ?
C13B C12B C11B 119.44(11) . . ?
C13B C12B H12B 120.3 . . ?
C12B C13B H13B 119.7 . . ?
C14B C13B C12B 120.54(10) . . ?
C14B C13B H13B 119.7 . . ?
C13B C14B H14B 119.7 . . ?
C13B C14B C15B 120.50(10) . . ?
C15B C14B H14B 119.7 . . ?
C10B C15B H15B 120.6 . . ?
C14B C15B C10B 118.86(10) . . ?
C14B C15B H15B 120.6 . . ?

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
O3A H3A O2 0.85(3) 1.86(3) 2.6923(15) 165(2) 2_655
O3B H3B O1 0.86(3) 1.97(4) 2.798(3) 162(6) 1_545

_shelx_SHELXL_version_number     2016/6
_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_ecv1_129
_database_code_depnum_ccdc_archive 'CCDC 2003347'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N2 O3'
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_chemical_absolute_configuration unk
_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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   25.6129(11)
_cell_length_b                   7.2650(3)
_cell_length_c                   7.5367(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1402.41(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1245 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.9765.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            73700
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        30.080
_diffrn_reflns_theta_max         30.082
_diffrn_reflns_theta_min         2.914
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3949
_reflns_number_total             4118
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.032
_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)+(0.0472P)²+0.2415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0748
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.30497(4) 0.21168(15) 0.68149(13) 0.0180(2) Uani 1 1 d . . . . .
O2 O 0.39083(4) 0.64325(14) 0.35070(15) 0.0185(2) Uani 1 1 d . . . . .
O3 O 0.37283(4) 0.69992(13) 0.77487(14) 0.0160(2) Uani 1 1 d . . . . .
N1 N 0.35674(4) 0.42639(15) 0.54169(14) 0.0112(2) Uani 1 1 d . . . . .
N2 N 0.53251(6) -0.0334(2) 0.7693(2) 0.0304(3) Uani 1 1 d . . . . .
C1 C 0.26295(6) 0.2915(2) 0.09840(18) 0.0166(3) Uani 1 1 d . . . . .
H1A H 0.260567 0.209584 -0.006284 0.020 Uiso 1 1 calc R . . . .
H1B H 0.232383 0.374710 0.103224 0.020 Uiso 1 1 calc R . . . .
C2 C 0.27176(5) 0.18535(18) 0.27325(19) 0.0153(2) Uani 1 1 d . . . . .
H2 H 0.244629 0.091987 0.304972 0.018 Uiso 1 1 calc R . . . .
C3 C 0.27718(5) 0.35385(17) 0.40266(17) 0.0113(2) Uani 1 1 d . . . . .
H3 H 0.242248 0.400722 0.441036 0.014 Uiso 1 1 calc R . . . .
C4 C 0.31226(5) 0.31729(18) 0.55967(17) 0.0116(2) Uani 1 1 d . . . . .
C5 C 0.35620(5) 0.53835(17) 0.38979(18) 0.0118(2) Uani 1 1 d . . . . .
C6 C 0.30663(5) 0.49780(16) 0.28934(18) 0.0107(2) Uani 1 1 d . . . . .
H6 H 0.285270 0.611691 0.272440 0.013 Uiso 1 1 calc R . . . .
C7 C 0.31537(5) 0.39489(19) 0.10929(18) 0.0138(2) Uani 1 1 d . . . . .
H7 H 0.324319 0.474090 0.005116 0.017 Uiso 1 1 calc R . . . .
C8 C 0.35241(6) 0.23637(19) 0.14659(19) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.387617 0.227302 0.107953 0.021 Uiso 1 1 calc R . . . .
C9 C 0.32672(6) 0.11219(19) 0.24320(19) 0.0182(3) Uani 1 1 d . . . . .
H9 H 0.340264 -0.001333 0.285582 0.022 Uiso 1 1 calc R . . . .
C10 C 0.39965(5) 0.41686(18) 0.66138(17) 0.0115(2) Uani 1 1 d . . . . .
C11 C 0.40756(5) 0.56029(17) 0.78290(18) 0.0128(2) Uani 1 1 d . . . . .
C12 C 0.44913(5) 0.5492(2) 0.9024(2) 0.0176(3) Uani 1 1 d . . . . .
H12 H 0.454918 0.645457 0.985339 0.021 Uiso 1 1 calc R . . . .
C13 C 0.48196(5) 0.3972(2) 0.8997(2) 0.0182(3) Uani 1 1 d . . . . .
H13 H 0.510180 0.389641 0.981198 0.022 Uiso 1 1 calc R . . . .
C14 C 0.47370(5) 0.25562(19) 0.77792(19) 0.0152(2) Uani 1 1 d . . . . .
C15 C 0.43220(5) 0.26576(18) 0.65754(18) 0.0140(2) Uani 1 1 d . . . . .
H15 H 0.426529 0.169709 0.574210 0.017 Uiso 1 1 calc R . . . .
C16 C 0.38002(6) 0.8516(2) 0.8951(2) 0.0201(3) Uani 1 1 d . . . . .
H16A H 0.353892 0.946763 0.870445 0.030 Uiso 1 1 calc GR . . . .
H16B H 0.415078 0.903105 0.879388 0.030 Uiso 1 1 calc GR . . . .
H16C H 0.375983 0.808265 1.017510 0.030 Uiso 1 1 calc GR . . . .
C17 C 0.50723(5) 0.0963(2) 0.7749(2) 0.0205(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
O1 C4 1.2110(17) . ?
O2 C5 1.2059(16) . ?
O3 C11 1.3504(15) . ?
O3 C16 1.4387(17) . ?
N1 C4 1.3946(16) . ?
N1 C5 1.4044(17) . ?
N1 C10 1.4236(15) . ?
N2 C17 1.144(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.543(2) . ?
C1 C7 1.5406(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.5713(18) . ?
C2 C9 1.522(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.5093(18) . ?
C3 C6 1.5467(18) . ?
C5 C6 1.5074(17) . ?
C6 H6 1.0000 . ?
C6 C7 1.5654(19) . ?
C7 H7 1.0000 . ?
C7 C8 1.5183(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.333(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4020(17) . ?
C10 C15 1.3788(18) . ?
C11 C12 1.3968(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3877(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(2) . ?
C14 C15 1.3994(19) . ?
C14 C17 1.4415(19) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C11 O3 C16 117.57(11) . . ?
C4 N1 C5 113.60(10) . . ?
C4 N1 C10 122.79(11) . . ?
C5 N1 C10 123.53(10) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.9 . . ?
C2 C1 H1B 112.9 . . ?
C7 C1 H1A 112.9 . . ?
C7 C1 H1B 112.9 . . ?
C7 C1 C2 94.06(10) . . ?
C1 C2 H2 116.2 . . ?
C1 C2 C3 98.84(10) . . ?
C3 C2 H2 116.2 . . ?
C9 C2 C1 100.52(11) . . ?
C9 C2 H2 116.2 . . ?
C9 C2 C3 106.43(10) . . ?
C2 C3 H3 111.5 . . ?
C4 C3 C2 113.71(11) . . ?
C4 C3 H3 111.5 . . ?
C4 C3 C6 105.17(10) . . ?
C6 C3 C2 103.13(10) . . ?
C6 C3 H3 111.5 . . ?
O1 C4 N1 124.04(12) . . ?
O1 C4 C3 127.89(12) . . ?
N1 C4 C3 108.07(11) . . ?
O2 C5 N1 123.91(12) . . ?
O2 C5 C6 128.34(12) . . ?
N1 C5 C6 107.73(10) . . ?
C3 C6 H6 111.3 . . ?
C3 C6 C7 103.03(10) . . ?
C5 C6 C3 105.40(10) . . ?
C5 C6 H6 111.3 . . ?
C5 C6 C7 114.10(10) . . ?
C7 C6 H6 111.3 . . ?
C1 C7 C6 98.89(10) . . ?
C1 C7 H7 116.0 . . ?
C6 C7 H7 116.0 . . ?
C8 C7 C1 100.62(11) . . ?
C8 C7 C6 106.93(11) . . ?
C8 C7 H7 116.0 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.83(12) . . ?
C9 C8 H8 126.1 . . ?
C2 C9 H9 126.2 . . ?
C8 C9 C2 107.54(12) . . ?
C8 C9 H9 126.2 . . ?
C11 C10 N1 119.30(11) . . ?
C15 C10 N1 119.49(12) . . ?
C15 C10 C11 121.21(12) . . ?
O3 C11 C10 115.71(11) . . ?
O3 C11 C12 125.06(12) . . ?
C12 C11 C10 119.22(12) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.92(13) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.28(12) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.20(12) . . ?
C13 C14 C17 120.81(13) . . ?
C15 C14 C17 118.99(13) . . ?
C10 C15 C14 119.18(12) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C14 177.59(18) . . ?

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
O2 C5 C6 C3 -179.72(13) . . . . ?
O2 C5 C6 C7 67.99(18) . . . . ?
O3 C11 C12 C13 179.12(13) . . . . ?
N1 C5 C6 C3 1.82(13) . . . . ?
N1 C5 C6 C7 -110.48(12) . . . . ?
N1 C10 C11 O3 -0.37(17) . . . . ?
N1 C10 C11 C12 178.86(12) . . . . ?
N1 C10 C15 C14 -178.75(12) . . . . ?
C1 C2 C3 C4 -149.88(11) . . . . ?
C1 C2 C3 C6 -36.56(12) . . . . ?
C1 C2 C9 C8 32.86(14) . . . . ?
C1 C7 C8 C9 -32.69(14) . . . . ?
C2 C1 C7 C6 -60.07(11) . . . . ?
C2 C1 C7 C8 49.14(12) . . . . ?
C2 C3 C4 O1 -66.89(17) . . . . ?
C2 C3 C4 N1 112.27(12) . . . . ?
C2 C3 C6 C5 -120.61(10) . . . . ?
C2 C3 C6 C7 -0.72(12) . . . . ?
C3 C2 C9 C8 -69.72(14) . . . . ?
C3 C6 C7 C1 37.84(11) . . . . ?
C3 C6 C7 C8 -66.20(12) . . . . ?
C4 N1 C5 O2 179.61(13) . . . . ?
C4 N1 C5 C6 -1.84(14) . . . . ?
C4 N1 C10 C11 -106.80(14) . . . . ?
C4 N1 C10 C15 72.25(16) . . . . ?
C4 C3 C6 C5 -1.20(13) . . . . ?
C4 C3 C6 C7 118.69(10) . . . . ?
C5 N1 C4 O1 -179.76(12) . . . . ?
C5 N1 C4 C3 1.04(14) . . . . ?
C5 N1 C10 C11 76.74(16) . . . . ?
C5 N1 C10 C15 -104.21(15) . . . . ?
C5 C6 C7 C1 151.55(11) . . . . ?
C5 C6 C7 C8 47.51(14) . . . . ?
C6 C3 C4 O1 -178.98(13) . . . . ?
C6 C3 C4 N1 0.18(13) . . . . ?
C6 C7 C8 C9 70.10(14) . . . . ?
C7 C1 C2 C3 59.46(11) . . . . ?
C7 C1 C2 C9 -49.20(12) . . . . ?
C7 C8 C9 C2 -0.15(16) . . . . ?
C9 C2 C3 C4 -46.08(14) . . . . ?
C9 C2 C3 C6 67.24(12) . . . . ?
C10 N1 C4 O1 3.5(2) . . . . ?
C10 N1 C4 C3 -175.75(11) . . . . ?
C10 N1 C5 O2 -3.6(2) . . . . ?
C10 N1 C5 C6 174.92(11) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C10 C15 C14 0.28(19) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C17 -179.41(14) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C15 C10 C11 O3 -179.40(12) . . . . ?
C15 C10 C11 C12 -0.17(19) . . . . ?
C16 O3 C11 C10 -178.93(12) . . . . ?
C16 O3 C11 C12 1.89(19) . . . . ?
C17 C14 C15 C10 179.22(13) . . . . ?

_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_ecv1_121
_database_code_depnum_ccdc_archive 'CCDC 2003344'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2 O5'
_chemical_formula_sum            'C16 H14 N2 O5'
_chemical_formula_weight         314.29
_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'
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                   7.7842(5)
_cell_length_b                   9.7899(6)
_cell_length_c                   10.0423(6)
_cell_angle_alpha                81.677(2)
_cell_angle_beta                 82.193(2)
_cell_angle_gamma                67.584(2)
_cell_volume                     697.29(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.120
_cell_measurement_theta_min      2.262
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1276 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.9362.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31746
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        30.190
_diffrn_reflns_theta_max         30.192
_diffrn_reflns_theta_min         2.262
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3192
_reflns_number_total             4121
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.3803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1111
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.94016(13) 0.18709(11) 0.49448(9) 0.0196(2) Uani 1 1 d . . . . .
O2 O 0.70453(13) 0.17786(10) 0.10386(9) 0.0193(2) Uani 1 1 d . . . . .
O3 O 0.60473(13) 0.47610(10) 0.21301(10) 0.0212(2) Uani 1 1 d . . . . .
O4 O 0.32587(15) 0.10105(12) 0.68322(11) 0.0290(3) Uani 1 1 d . . . . .
O5 O 0.10454(14) 0.31555(12) 0.70560(10) 0.0246(2) Uani 1 1 d . . . . .
N1 N 0.78183(14) 0.19288(11) 0.31407(10) 0.0139(2) Uani 1 1 d . . . . .
N2 N 0.25154(15) 0.23514(13) 0.64976(11) 0.0184(2) Uani 1 1 d . . . . .
C1 C 1.32198(18) 0.09525(16) 0.10656(13) 0.0195(3) Uani 1 1 d . . . . .
H1A H 1.382834 -0.014311 0.118896 0.023 Uiso 1 1 calc R . . . .
H1B H 1.408442 0.139299 0.053521 0.023 Uiso 1 1 calc R . . . .
C2 C 1.24015(18) 0.16322(16) 0.24021(14) 0.0191(3) Uani 1 1 d . . . . .
H2 H 1.332229 0.156110 0.303813 0.023 Uiso 1 1 calc R . . . .
C3 C 1.10780(17) 0.07542(14) 0.29001(12) 0.0153(2) Uani 1 1 d . . . . .
H3 H 1.178595 -0.026469 0.332202 0.018 Uiso 1 1 calc R . . . .
C4 C 0.94131(17) 0.15586(14) 0.38165(12) 0.0147(2) Uani 1 1 d . . . . .
C5 C 0.82107(17) 0.15044(13) 0.18163(12) 0.0148(2) Uani 1 1 d . . . . .
C6 C 1.02961(17) 0.06862(14) 0.15914(12) 0.0145(2) Uani 1 1 d . . . . .
H6 H 1.059915 -0.036478 0.141822 0.017 Uiso 1 1 calc R . . . .
C7 C 1.13207(18) 0.14800(15) 0.04761(13) 0.0174(3) Uani 1 1 d . . . . .
H7 H 1.134932 0.127634 -0.047579 0.021 Uiso 1 1 calc R . . . .
C8 C 1.05456(19) 0.30981(15) 0.07405(14) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.974914 0.390353 0.019314 0.024 Uiso 1 1 calc R . . . .
C9 C 1.11805(19) 0.31897(15) 0.18774(15) 0.0214(3) Uani 1 1 d . . . . .
H9 H 1.091648 0.407227 0.228705 0.026 Uiso 1 1 calc R . . . .
C10 C 0.60039(16) 0.27731(14) 0.37092(12) 0.0143(2) Uani 1 1 d . . . . .
C11 C 0.51030(17) 0.42561(14) 0.31849(13) 0.0157(2) Uani 1 1 d . . . . .
C12 C 0.33678(18) 0.51076(14) 0.37830(13) 0.0175(3) Uani 1 1 d . . . . .
H12 H 0.275052 0.610841 0.343117 0.021 Uiso 1 1 calc R . . . .
C13 C 0.25469(17) 0.44899(15) 0.48915(13) 0.0172(3) Uani 1 1 d . . . . .
H13 H 0.138329 0.507298 0.532019 0.021 Uiso 1 1 calc R . . . .
C14 C 0.34334(17) 0.30184(14) 0.53699(12) 0.0156(2) Uani 1 1 d . . . . .
C15 C 0.51648(17) 0.21460(14) 0.47925(12) 0.0148(2) Uani 1 1 d . . . . .
H15 H 0.575803 0.113875 0.513676 0.018 Uiso 1 1 calc R . . . .
C16 C 0.5078(2) 0.61784(17) 0.14253(17) 0.0313(4) Uani 1 1 d . . . . .
H16A H 0.478095 0.695818 0.202565 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.392181 0.618271 0.113902 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.587081 0.636252 0.062978 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2136(15) . ?
O2 C5 1.2046(15) . ?
O3 C11 1.3493(16) . ?
O3 C16 1.4345(16) . ?
O4 N2 1.2316(15) . ?
O5 N2 1.2288(14) . ?
N1 C4 1.3956(15) . ?
N1 C5 1.4098(16) . ?
N1 C10 1.4252(15) . ?
N2 C14 1.4634(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5340(19) . ?
C1 C7 1.5394(18) . ?
C2 H2 1.0000 . ?
C2 C3 1.5689(18) . ?
C2 C9 1.518(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.5014(17) . ?
C3 C6 1.5414(17) . ?
C5 C6 1.5129(17) . ?
C6 H6 1.0000 . ?
C6 C7 1.5725(18) . ?
C7 H7 1.0000 . ?
C7 C8 1.5144(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.331(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4068(17) . ?
C10 C15 1.3808(17) . ?
C11 C12 1.3950(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3855(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3834(18) . ?
C14 C15 1.3911(17) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C11 O3 C16 117.79(11) . . ?
C4 N1 C5 113.32(10) . . ?
C4 N1 C10 122.26(10) . . ?
C5 N1 C10 124.18(10) . . ?
O4 N2 C14 118.04(11) . . ?
O5 N2 O4 123.57(11) . . ?
O5 N2 C14 118.38(11) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.8 . . ?
C2 C1 H1B 112.8 . . ?
C2 C1 C7 94.49(10) . . ?
C7 C1 H1A 112.8 . . ?
C7 C1 H1B 112.8 . . ?
C1 C2 H2 116.2 . . ?
C1 C2 C3 98.43(10) . . ?
C3 C2 H2 116.2 . . ?
C9 C2 C1 100.37(11) . . ?
C9 C2 H2 116.2 . . ?
C9 C2 C3 107.03(10) . . ?
C2 C3 H3 111.1 . . ?
C4 C3 C2 114.04(11) . . ?
C4 C3 H3 111.1 . . ?
C4 C3 C6 105.70(10) . . ?
C6 C3 C2 103.24(10) . . ?
C6 C3 H3 111.1 . . ?
O1 C4 N1 124.28(11) . . ?
O1 C4 C3 127.56(11) . . ?
N1 C4 C3 108.16(10) . . ?
O2 C5 N1 124.09(12) . . ?
O2 C5 C6 128.34(12) . . ?
N1 C5 C6 107.57(10) . . ?
C3 C6 H6 111.1 . . ?
C3 C6 C7 103.05(10) . . ?
C5 C6 C3 105.16(10) . . ?
C5 C6 H6 111.1 . . ?
C5 C6 C7 114.74(10) . . ?
C7 C6 H6 111.1 . . ?
C1 C7 C6 99.16(10) . . ?
C1 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
C8 C7 C1 100.39(11) . . ?
C8 C7 C6 105.82(10) . . ?
C8 C7 H7 116.3 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.74(12) . . ?
C9 C8 H8 126.1 . . ?
C2 C9 H9 126.1 . . ?
C8 C9 C2 107.79(12) . . ?
C8 C9 H9 126.1 . . ?
C11 C10 N1 119.61(11) . . ?
C15 C10 N1 119.90(11) . . ?
C15 C10 C11 120.47(11) . . ?
O3 C11 C10 115.68(11) . . ?
O3 C11 C12 124.58(11) . . ?
C12 C11 C10 119.71(11) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.82(12) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.55(12) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 N2 119.28(11) . . ?
C13 C14 C15 121.72(12) . . ?
C15 C14 N2 118.99(11) . . ?
C10 C15 C14 118.68(11) . . ?
C10 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C5 C6 C3 176.72(13) . . . . ?
O2 C5 C6 C7 64.24(17) . . . . ?
O3 C11 C12 C13 -177.95(12) . . . . ?
O4 N2 C14 C13 174.10(12) . . . . ?
O4 N2 C14 C15 -4.87(18) . . . . ?
O5 N2 C14 C13 -5.68(18) . . . . ?
O5 N2 C14 C15 175.36(12) . . . . ?
N1 C5 C6 C3 -2.86(13) . . . . ?
N1 C5 C6 C7 -115.34(11) . . . . ?
N1 C10 C11 O3 1.56(17) . . . . ?
N1 C10 C11 C12 -176.79(11) . . . . ?
N1 C10 C15 C14 176.86(11) . . . . ?
N2 C14 C15 C10 178.56(11) . . . . ?
C1 C2 C3 C4 -152.94(10) . . . . ?
C1 C2 C3 C6 -38.77(12) . . . . ?
C1 C2 C9 C8 32.58(14) . . . . ?
C1 C7 C8 C9 -32.61(13) . . . . ?
C2 C1 C7 C6 -58.93(11) . . . . ?
C2 C1 C7 C8 49.14(12) . . . . ?
C2 C3 C4 O1 -66.26(17) . . . . ?
C2 C3 C4 N1 112.79(12) . . . . ?
C2 C3 C6 C5 -118.38(10) . . . . ?
C2 C3 C6 C7 2.14(12) . . . . ?
C3 C2 C9 C8 -69.66(13) . . . . ?
C3 C6 C7 C1 35.11(11) . . . . ?
C3 C6 C7 C8 -68.51(12) . . . . ?
C4 N1 C5 O2 -176.46(12) . . . . ?
C4 N1 C5 C6 3.14(14) . . . . ?
C4 N1 C10 C11 107.55(14) . . . . ?
C4 N1 C10 C15 -70.64(16) . . . . ?
C4 C3 C6 C5 1.68(13) . . . . ?
C4 C3 C6 C7 122.20(10) . . . . ?
C5 N1 C4 O1 177.05(12) . . . . ?
C5 N1 C4 C3 -2.03(14) . . . . ?
C5 N1 C10 C11 -66.43(16) . . . . ?
C5 N1 C10 C15 115.37(13) . . . . ?
C5 C6 C7 C1 148.83(11) . . . . ?
C5 C6 C7 C8 45.21(14) . . . . ?
C6 C3 C4 O1 -178.97(12) . . . . ?
C6 C3 C4 N1 0.08(13) . . . . ?
C6 C7 C8 C9 70.11(13) . . . . ?
C7 C1 C2 C3 60.14(11) . . . . ?
C7 C1 C2 C9 -49.02(11) . . . . ?
C7 C8 C9 C2 0.09(14) . . . . ?
C9 C2 C3 C4 -49.31(14) . . . . ?
C9 C2 C3 C6 64.86(12) . . . . ?
C10 N1 C4 O1 2.47(19) . . . . ?
C10 N1 C4 C3 -176.61(11) . . . . ?
C10 N1 C5 O2 -2.00(19) . . . . ?
C10 N1 C5 C6 177.60(11) . . . . ?
C10 C11 C12 C13 0.25(19) . . . . ?
C11 C10 C15 C14 -1.33(18) . . . . ?
C11 C12 C13 C14 -1.92(19) . . . . ?
C12 C13 C14 N2 -176.92(11) . . . . ?
C12 C13 C14 C15 2.01(19) . . . . ?
C13 C14 C15 C10 -0.38(19) . . . . ?
C15 C10 C11 O3 179.75(11) . . . . ?
C15 C10 C11 C12 1.40(18) . . . . ?
C16 O3 C11 C10 170.43(12) . . . . ?
C16 O3 C11 C12 -11.31(19) . . . . ?

_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_ecv1_169
_database_code_depnum_ccdc_archive 'CCDC 2003348'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Cl N O3'
_chemical_formula_sum            'C15 H12 Cl N O3'
_chemical_formula_weight         289.71
_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      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                   21.3570(9)
_cell_length_b                   6.8190(3)
_cell_length_c                   20.0691(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.0080(10)
_cell_angle_gamma                90
_cell_volume                     2648.72(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.9558.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            61497
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        30.053
_diffrn_reflns_theta_max         30.053
_diffrn_reflns_theta_min         2.240
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5865
_reflns_number_total             7769
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         7769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.017
_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)+(0.0361P)²+2.2210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1019
_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 Ternary CH refined with riding coordinates:
 C2A(H2A), C3A(H3AA), C6A(H6A), C7A(H7A), C2B(H2B), C3B(H3BA), C6B(H6B),
 C7B(H7B)
2.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1B(H1BA,H1BB)
2.c Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C13A(H13A), C15A(H15A), C8B(H8B), C9B(H9B),
 C12B(H12B), C13B(H13B), C15B(H15B)
;
_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
Cl1A Cl -0.15625(2) 0.39535(7) -0.03546(2) 0.02570(10) Uani 1 1 d . . . . .
O1A O 0.03967(6) 0.60561(17) 0.28361(6) 0.0215(2) Uani 1 1 d . . . . .
O2A O 0.09291(6) 0.12408(15) 0.15938(6) 0.0178(2) Uani 1 1 d . . . . .
O3A O 0.10465(5) 0.73673(17) 0.17648(6) 0.0170(2) Uani 1 1 d . . . . .
H3A H 0.1073(12) 0.860(4) 0.1677(12) 0.042(6) Uiso 1 1 d . . . . .
N1A N 0.06056(6) 0.38804(17) 0.20807(6) 0.0117(2) Uani 1 1 d . . . . .
C1A C 0.22137(8) 0.1929(3) 0.40673(9) 0.0270(4) Uani 1 1 d . . . . .
H1AA H 0.200195 0.097685 0.428332 0.032 Uiso 1 1 calc R . . . .
H1AB H 0.271237 0.207965 0.438884 0.032 Uiso 1 1 calc R . . . .
C2A C 0.18267(8) 0.3903(3) 0.38725(8) 0.0212(3) Uani 1 1 d . . . . .
H2A H 0.184913 0.472008 0.429581 0.025 Uiso 1 1 calc R . . . .
C3A C 0.10926(7) 0.3123(2) 0.33392(8) 0.0158(3) Uani 1 1 d . . . . .
H3AA H 0.083604 0.261495 0.362040 0.019 Uiso 1 1 calc R . . . .
C4A C 0.06609(7) 0.4562(2) 0.27592(8) 0.0142(3) Uani 1 1 d . . . . .
C5A C 0.09236(7) 0.2095(2) 0.21260(8) 0.0133(3) Uani 1 1 d . . . . .
C6A C 0.12571(7) 0.1459(2) 0.29190(8) 0.0155(3) Uani 1 1 d . . . . .
H6A H 0.106867 0.017409 0.299171 0.019 Uiso 1 1 calc R . . . .
C7A C 0.20684(8) 0.1443(3) 0.32641(9) 0.0216(3) Uani 1 1 d . . . . .
H7A H 0.228930 0.022413 0.318617 0.026 Uiso 1 1 calc R . . . .
C8A C 0.22829(8) 0.3343(3) 0.30355(9) 0.0230(3) Uani 1 1 d . . . . .
H8A H 0.248523 0.347756 0.269766 0.028 Uiso 1 1 calc R . . . .
C9A C 0.21392(8) 0.4796(3) 0.33896(9) 0.0221(3) Uani 1 1 d . . . . .
H9A H 0.221798 0.615202 0.334786 0.027 Uiso 1 1 calc R . . . .
C10A C 0.02064(7) 0.4864(2) 0.14046(7) 0.0126(3) Uani 1 1 d . . . . .
C11A C 0.04347(7) 0.6662(2) 0.12643(8) 0.0136(3) Uani 1 1 d . . . . .
C12A C 0.00264(8) 0.7636(2) 0.06117(8) 0.0170(3) Uani 1 1 d . . . . .
H12A H 0.017033 0.887323 0.050867 0.020 Uiso 1 1 calc R . . . .
C13A C -0.05861(8) 0.6816(2) 0.01135(8) 0.0182(3) Uani 1 1 d . . . . .
H13A H -0.085984 0.748096 -0.033118 0.022 Uiso 1 1 calc R . . . .
C14A C -0.07962(7) 0.5020(2) 0.02687(8) 0.0169(3) Uani 1 1 d . . . . .
C15A C -0.04076(7) 0.4028(2) 0.09121(8) 0.0150(3) Uani 1 1 d . . . . .
H15A H -0.055730 0.280012 0.101524 0.018 Uiso 1 1 calc R . . . .
Cl1B Cl 0.77046(2) 0.60461(7) 0.38056(2) 0.03096(11) Uani 1 1 d . . . . .
O1B O 0.46656(6) 0.40827(18) 0.22035(6) 0.0237(3) Uani 1 1 d . . . . .
O2B O 0.56202(6) 0.84935(16) 0.12018(6) 0.0204(2) Uani 1 1 d . . . . .
O3B O 0.54561(6) 0.23881(17) 0.12759(6) 0.0194(2) Uani 1 1 d . . . . .
H3B H 0.5544(12) 0.115(4) 0.1205(13) 0.044(7) Uiso 1 1 d . . . . .
N1B N 0.52635(6) 0.60110(18) 0.17306(6) 0.0135(2) Uani 1 1 d . . . . .
C1B C 0.32658(8) 0.7723(3) 0.02126(9) 0.0266(4) Uani 1 1 d . . . . .
H1BA H 0.311740 0.879097 0.044768 0.032 Uiso 1 1 calc R . . . .
H1BB H 0.289991 0.743716 -0.028277 0.032 Uiso 1 1 calc R . . . .
C2B C 0.35102(8) 0.5889(3) 0.06975(9) 0.0231(3) Uani 1 1 d . . . . .
H2B H 0.314747 0.515262 0.078594 0.028 Uiso 1 1 calc R . . . .
C3B C 0.41003(7) 0.6830(2) 0.13912(8) 0.0175(3) Uani 1 1 d . . . . .
H3BA H 0.390940 0.748123 0.171211 0.021 Uiso 1 1 calc R . . . .
C4B C 0.46762(7) 0.5450(2) 0.18265(8) 0.0159(3) Uani 1 1 d . . . . .
C5B C 0.51649(8) 0.7704(2) 0.13212(8) 0.0157(3) Uani 1 1 d . . . . .
C6B C 0.44230(8) 0.8339(2) 0.10602(8) 0.0180(3) Uani 1 1 d . . . . .
H6B H 0.438971 0.969767 0.122989 0.022 Uiso 1 1 calc R . . . .
C7B C 0.39771(8) 0.8112(3) 0.02091(9) 0.0230(3) Uani 1 1 d . . . . .
H7B H 0.400005 0.921941 -0.010640 0.028 Uiso 1 1 calc R . . . .
C8B C 0.41322(8) 0.6087(3) 0.00067(9) 0.0254(4) Uani 1 1 d . . . . .
H8B H 0.437942 0.580494 -0.027966 0.031 Uiso 1 1 calc R . . . .
C9B C 0.38637(8) 0.4781(3) 0.02978(9) 0.0254(4) Uani 1 1 d . . . . .
H9B H 0.388793 0.339568 0.026275 0.030 Uiso 1 1 calc R . . . .
C10B C 0.59131(7) 0.5036(2) 0.20910(8) 0.0140(3) Uani 1 1 d . . . . .
C11B C 0.59965(7) 0.3172(2) 0.18537(8) 0.0159(3) Uani 1 1 d . . . . .
C12B C 0.66289(8) 0.2226(2) 0.22195(9) 0.0198(3) Uani 1 1 d . . . . .
H12B H 0.669696 0.096580 0.205943 0.024 Uiso 1 1 calc R . . . .
C13B C 0.71599(8) 0.3100(3) 0.28140(9) 0.0220(3) Uani 1 1 d . . . . .
H13B H 0.758990 0.244699 0.306076 0.026 Uiso 1 1 calc R . . . .
C14B C 0.70559(7) 0.4942(2) 0.30446(8) 0.0200(3) Uani 1 1 d . . . . .
C15B C 0.64385(7) 0.5927(2) 0.26862(8) 0.0170(3) Uani 1 1 d . . . . .
H15B H 0.637471 0.719376 0.284466 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
Cl1A C14A 1.7439(15) . ?
O1A C4A 1.2057(18) . ?
O2A C5A 1.2209(18) . ?
O3A H3A 0.86(3) . ?
O3A C11A 1.3555(17) . ?
N1A C4A 1.3958(18) . ?
N1A C5A 1.3784(18) . ?
N1A C10A 1.4283(17) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.541(2) . ?
C1A C7A 1.543(2) . ?
C2A H2A 1.0000 . ?
C2A C3A 1.571(2) . ?
C2A C9A 1.517(2) . ?
C3A H3AA 1.0000 . ?
C3A C4A 1.504(2) . ?
C3A C6A 1.540(2) . ?
C5A C6A 1.507(2) . ?
C6A H6A 1.0000 . ?
C6A C7A 1.571(2) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.509(2) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.328(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.392(2) . ?
C10A C15A 1.3876(19) . ?
C11A C12A 1.397(2) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.385(2) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.385(2) . ?
C14A C15A 1.381(2) . ?
C15A H15A 0.9500 . ?
Cl1B C14B 1.7407(16) . ?
O1B C4B 1.2071(19) . ?
O2B C5B 1.2205(18) . ?
O3B H3B 0.89(3) . ?
O3B C11B 1.3532(18) . ?
N1B C4B 1.4003(18) . ?
N1B C5B 1.3806(19) . ?
N1B C10B 1.4287(18) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.534(2) . ?
C1B C7B 1.545(2) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.567(2) . ?
C2B C9B 1.515(2) . ?
C3B H3BA 1.0000 . ?
C3B C4B 1.501(2) . ?
C3B C6B 1.537(2) . ?
C5B C6B 1.507(2) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.573(2) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.515(2) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.322(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.395(2) . ?
C10B C15B 1.386(2) . ?
C11B C12B 1.393(2) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.386(2) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.388(2) . ?
C14B C15B 1.380(2) . ?
C15B H15B 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
C11A O3A H3A 108.6(15) . . ?
C4A N1A C10A 122.73(12) . . ?
C5A N1A C4A 113.19(12) . . ?
C5A N1A C10A 123.86(12) . . ?
H1AA C1A H1AB 110.3 . . ?
C2A C1A H1AA 112.9 . . ?
C2A C1A H1AB 112.9 . . ?
C2A C1A C7A 94.20(12) . . ?
C7A C1A H1AA 112.9 . . ?
C7A C1A H1AB 112.9 . . ?
C1A C2A H2A 116.3 . . ?
C1A C2A C3A 98.67(13) . . ?
C3A C2A H2A 116.3 . . ?
C9A C2A C1A 100.31(13) . . ?
C9A C2A H2A 116.3 . . ?
C9A C2A C3A 106.41(12) . . ?
C2A C3A H3AA 111.1 . . ?
C4A C3A C2A 114.52(13) . . ?
C4A C3A H3AA 111.1 . . ?
C4A C3A C6A 105.32(11) . . ?
C6A C3A C2A 103.28(12) . . ?
C6A C3A H3AA 111.1 . . ?
O1A C4A N1A 123.72(13) . . ?
O1A C4A C3A 128.27(13) . . ?
N1A C4A C3A 108.01(12) . . ?
O2A C5A N1A 123.39(13) . . ?
O2A C5A C6A 127.71(13) . . ?
N1A C5A C6A 108.88(12) . . ?
C3A C6A H6A 111.5 . . ?
C3A C6A C7A 103.18(12) . . ?
C5A C6A C3A 104.53(12) . . ?
C5A C6A H6A 111.5 . . ?
C5A C6A C7A 114.10(12) . . ?
C7A C6A H6A 111.5 . . ?
C1A C7A C6A 98.99(12) . . ?
C1A C7A H7A 116.2 . . ?
C6A C7A H7A 116.2 . . ?
C8A C7A C1A 100.37(14) . . ?
C8A C7A C6A 106.27(12) . . ?
C8A C7A H7A 116.2 . . ?
C7A C8A H8A 126.0 . . ?
C9A C8A C7A 108.01(14) . . ?
C9A C8A H8A 126.0 . . ?
C2A C9A H9A 126.1 . . ?
C8A C9A C2A 107.82(15) . . ?
C8A C9A H9A 126.1 . . ?
C11A C10A N1A 119.11(12) . . ?
C15A C10A N1A 119.25(13) . . ?
C15A C10A C11A 121.62(13) . . ?
O3A C11A C10A 118.22(13) . . ?
O3A C11A C12A 123.39(14) . . ?
C10A C11A C12A 118.38(13) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.65(14) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 120.3 . . ?
C14A C13A C12A 119.46(14) . . ?
C14A C13A H13A 120.3 . . ?
C13A C14A Cl1A 120.17(11) . . ?
C15A C14A Cl1A 118.53(12) . . ?
C15A C14A C13A 121.30(14) . . ?
C10A C15A H15A 120.7 . . ?
C14A C15A C10A 118.58(14) . . ?
C14A C15A H15A 120.7 . . ?
C11B O3B H3B 110.5(15) . . ?
C4B N1B C10B 122.53(12) . . ?
C5B N1B C4B 112.96(12) . . ?
C5B N1B C10B 124.16(12) . . ?
H1BA C1B H1BB 110.3 . . ?
C2B C1B H1BA 112.9 . . ?
C2B C1B H1BB 112.9 . . ?
C2B C1B C7B 94.09(12) . . ?
C7B C1B H1BA 112.9 . . ?
C7B C1B H1BB 112.9 . . ?
C1B C2B H2B 116.1 . . ?
C1B C2B C3B 99.20(14) . . ?
C3B C2B H2B 116.1 . . ?
C9B C2B C1B 100.53(14) . . ?
C9B C2B H2B 116.1 . . ?
C9B C2B C3B 106.33(12) . . ?
C2B C3B H3BA 111.1 . . ?
C4B C3B C2B 114.44(13) . . ?
C4B C3B H3BA 111.1 . . ?
C4B C3B C6B 105.32(11) . . ?
C6B C3B C2B 103.26(12) . . ?
C6B C3B H3BA 111.1 . . ?
O1B C4B N1B 123.54(14) . . ?
O1B C4B C3B 128.39(13) . . ?
N1B C4B C3B 108.06(12) . . ?
O2B C5B N1B 123.50(13) . . ?
O2B C5B C6B 127.81(14) . . ?
N1B C5B C6B 108.69(12) . . ?
C3B C6B H6B 111.3 . . ?
C3B C6B C7B 103.13(12) . . ?
C5B C6B C3B 104.79(12) . . ?
C5B C6B H6B 111.3 . . ?
C5B C6B C7B 114.47(12) . . ?
C7B C6B H6B 111.3 . . ?
C1B C7B C6B 99.03(12) . . ?
C1B C7B H7B 116.4 . . ?
C6B C7B H7B 116.4 . . ?
C8B C7B C1B 99.88(14) . . ?
C8B C7B C6B 106.28(12) . . ?
C8B C7B H7B 116.4 . . ?
C7B C8B H8B 125.9 . . ?
C9B C8B C7B 108.11(15) . . ?
C9B C8B H8B 125.9 . . ?
C2B C9B H9B 126.1 . . ?
C8B C9B C2B 107.71(16) . . ?
C8B C9B H9B 126.1 . . ?
C11B C10B N1B 119.21(13) . . ?
C15B C10B N1B 119.43(13) . . ?
C15B C10B C11B 121.32(13) . . ?
O3B C11B C10B 117.83(13) . . ?
O3B C11B C12B 123.66(14) . . ?
C12B C11B C10B 118.51(14) . . ?
C11B C12B H12B 119.6 . . ?
C13B C12B C11B 120.84(15) . . ?
C13B C12B H12B 119.6 . . ?
C12B C13B H13B 120.4 . . ?
C12B C13B C14B 119.20(14) . . ?
C14B C13B H13B 120.4 . . ?
C13B C14B Cl1B 120.24(12) . . ?
C15B C14B Cl1B 118.51(13) . . ?
C15B C14B C13B 121.25(14) . . ?
C10B C15B H15B 120.6 . . ?
C14B C15B C10B 118.86(14) . . ?
C14B C15B H15B 120.6 . . ?

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
_geom_hbond_publ_flag
O3A H3A O2A 0.86(3) 1.83(3) 2.6617(16) 163(2) 1_565 yes
O3B H3B O2B 0.89(3) 1.82(3) 2.6911(16) 166(2) 1_545 yes

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
Cl1A C14A C15A C10A 179.26(11) . . . . ?
O2A C5A C6A C3A 178.78(14) . . . . ?
O2A C5A C6A C7A 66.8(2) . . . . ?
O3A C11A C12A C13A 178.42(13) . . . . ?
N1A C5A C6A C3A -0.06(15) . . . . ?
N1A C5A C6A C7A -112.02(14) . . . . ?
N1A C10A C11A O3A 2.87(19) . . . . ?
N1A C10A C11A C12A -177.87(12) . . . . ?
N1A C10A C15A C14A 178.46(12) . . . . ?
C1A C2A C3A C4A -151.66(13) . . . . ?
C1A C2A C3A C6A -37.71(14) . . . . ?
C1A C2A C9A C8A 32.41(16) . . . . ?
C1A C7A C8A C9A -32.97(16) . . . . ?
C2A C1A C7A C6A -59.31(14) . . . . ?
C2A C1A C7A C8A 49.18(13) . . . . ?
C2A C3A C4A O1A -70.0(2) . . . . ?
C2A C3A C4A N1A 110.12(14) . . . . ?
C2A C3A C6A C5A -118.84(12) . . . . ?
C2A C3A C6A C7A 0.76(14) . . . . ?
C3A C2A C9A C8A -69.91(16) . . . . ?
C3A C6A C7A C1A 36.39(15) . . . . ?
C3A C6A C7A C8A -67.26(15) . . . . ?
C4A N1A C5A O2A 179.39(13) . . . . ?
C4A N1A C5A C6A -1.71(16) . . . . ?
C4A N1A C10A C11A 69.99(17) . . . . ?
C4A N1A C10A C15A -108.46(16) . . . . ?
C4A C3A C6A C5A 1.61(14) . . . . ?
C4A C3A C6A C7A 121.21(12) . . . . ?
C5A N1A C4A O1A -177.09(13) . . . . ?
C5A N1A C4A C3A 2.78(16) . . . . ?
C5A N1A C10A C11A -115.78(15) . . . . ?
C5A N1A C10A C15A 65.77(18) . . . . ?
C5A C6A C7A C1A 149.17(13) . . . . ?
C5A C6A C7A C8A 45.51(17) . . . . ?
C6A C3A C4A O1A 177.25(14) . . . . ?
C6A C3A C4A N1A -2.63(15) . . . . ?
C6A C7A C8A C9A 69.67(16) . . . . ?
C7A C1A C2A C3A 59.69(13) . . . . ?
C7A C1A C2A C9A -48.86(14) . . . . ?
C7A C8A C9A C2A 0.38(17) . . . . ?
C9A C2A C3A C4A -48.14(17) . . . . ?
C9A C2A C3A C6A 65.80(15) . . . . ?
C10A N1A C4A O1A -2.3(2) . . . . ?
C10A N1A C4A C3A 177.57(12) . . . . ?
C10A N1A C5A O2A 4.7(2) . . . . ?
C10A N1A C5A C6A -176.43(12) . . . . ?
C10A C11A C12A C13A -0.8(2) . . . . ?
C11A C10A C15A C14A 0.1(2) . . . . ?
C11A C12A C13A C14A 0.5(2) . . . . ?
C12A C13A C14A Cl1A -179.51(11) . . . . ?
C12A C13A C14A C15A 0.1(2) . . . . ?
C13A C14A C15A C10A -0.4(2) . . . . ?
C15A C10A C11A O3A -178.72(13) . . . . ?
C15A C10A C11A C12A 0.5(2) . . . . ?
Cl1B C14B C15B C10B -178.39(11) . . . . ?
O2B C5B C6B C3B -178.69(15) . . . . ?
O2B C5B C6B C7B 69.1(2) . . . . ?
O3B C11B C12B C13B -179.22(14) . . . . ?
N1B C5B C6B C3B 1.78(16) . . . . ?
N1B C5B C6B C7B -110.45(15) . . . . ?
N1B C10B C11B O3B 1.47(19) . . . . ?
N1B C10B C11B C12B -178.84(13) . . . . ?
N1B C10B C15B C14B 177.90(13) . . . . ?
C1B C2B C3B C4B -151.44(13) . . . . ?
C1B C2B C3B C6B -37.53(14) . . . . ?
C1B C2B C9B C8B 32.44(16) . . . . ?
C1B C7B C8B C9B -33.34(16) . . . . ?
C2B C1B C7B C6B -59.01(14) . . . . ?
C2B C1B C7B C8B 49.40(14) . . . . ?
C2B C3B C4B O1B -70.6(2) . . . . ?
C2B C3B C4B N1B 109.73(14) . . . . ?
C2B C3B C6B C5B -119.62(13) . . . . ?
C2B C3B C6B C7B 0.47(15) . . . . ?
C3B C2B C9B C8B -70.51(16) . . . . ?
C3B C6B C7B C1B 36.40(15) . . . . ?
C3B C6B C7B C8B -66.74(15) . . . . ?
C4B N1B C5B O2B 176.53(14) . . . . ?
C4B N1B C5B C6B -3.91(17) . . . . ?
C4B N1B C10B C11B 73.15(18) . . . . ?
C4B N1B C10B C15B -104.42(17) . . . . ?
C4B C3B C6B C5B 0.73(15) . . . . ?
C4B C3B C6B C7B 120.82(13) . . . . ?
C5B N1B C4B O1B -175.36(14) . . . . ?
C5B N1B C4B C3B 4.38(17) . . . . ?
C5B N1B C10B C11B -114.03(16) . . . . ?
C5B N1B C10B C15B 68.40(19) . . . . ?
C5B C6B C7B C1B 149.62(14) . . . . ?
C5B C6B C7B C8B 46.47(18) . . . . ?
C6B C3B C4B O1B 176.76(16) . . . . ?
C6B C3B C4B N1B -2.96(16) . . . . ?
C6B C7B C8B C9B 69.18(16) . . . . ?
C7B C1B C2B C3B 59.44(14) . . . . ?
C7B C1B C2B C9B -49.21(14) . . . . ?
C7B C8B C9B C2B 0.76(17) . . . . ?
C9B C2B C3B C4B -47.53(17) . . . . ?
C9B C2B C3B C6B 66.38(16) . . . . ?
C10B N1B C4B O1B -1.8(2) . . . . ?
C10B N1B C4B C3B 177.93(13) . . . . ?
C10B N1B C5B O2B 3.1(2) . . . . ?
C10B N1B C5B C6B -177.34(13) . . . . ?
C10B C11B C12B C13B 1.1(2) . . . . ?
C11B C10B C15B C14B 0.4(2) . . . . ?
C11B C12B C13B C14B 0.0(2) . . . . ?
C12B C13B C14B Cl1B 178.16(12) . . . . ?
C12B C13B C14B C15B -1.0(2) . . . . ?
C13B C14B C15B C10B 0.8(2) . . . . ?
C15B C10B C11B O3B 178.99(13) . . . . ?
C15B C10B C11B C12B -1.3(2) . . . . ?

_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_ecv1_125_a
_database_code_depnum_ccdc_archive 'CCDC 2003345'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Cl N O3'
_chemical_formula_sum            'C15 H12 Cl N O3'
_chemical_formula_weight         289.71
_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      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                   17.4699(12)
_cell_length_b                   6.8917(5)
_cell_length_c                   22.137(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.5700(16)
_cell_angle_gamma                90
_cell_volume                     2590.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1270 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9437.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            49286
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.723
_diffrn_reflns_theta_max         27.723
_diffrn_reflns_theta_min         2.399
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2832
_reflns_number_total             3036
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.294
_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)+(0.0277P)²+7.6465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1B-C10B \\sim N1-C10
 with sigma of 0.01
 O3A-C11 \\sim O3C-C15 \\sim O3D-C15B \\sim O3C-C11B
 with sigma of 0.01
3. Restrained planarity
 C12B, C13B, C14B, C15B, C10B, C11B
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C6B)
Uanis(C12) = Uanis(C12B)
Uanis(Cl1) = Uanis(Cl1B)
Uanis(N1) = Uanis(N1B)
5. Same fragment restrains
{O1, O2, N1, C1, C2, C3, C4, C5, C6, C7, C8, C9} sigma for 1-2: 0.015, 1-3: 0.04
as
{O1B, O2B, N1B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B}
{Cl1, O3A, O3C, C10, C11, C12, C13, C14, C15} sigma for 1-2: 0.015, 1-3: 0.04
as
{Cl1B, O3B, O3D, C10B, C11B, C12B, C13B, C14B, C15B}
6. Others
 Sof(O1B)=Sof(O2B)=Sof(N1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2B)=
 Sof(C3B)=Sof(H3BA)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=
 Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(Cl1B)=Sof(C10B)=Sof(C11B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=1-FVAR(1)
 Sof(O3B)=Sof(H15B)=0.6*(1-FVAR(2))
 Sof(O3D)=Sof(H11B)=0.4*(1-FVAR(2))
 Sof(O3A)=Sof(O3C)=Sof(H11)=Sof(H15)=0.5*FVAR(2)
 Sof(O1)=Sof(O2)=Sof(N1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2)=Sof(C3)=
 Sof(H3)=Sof(C4)=Sof(C5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=
 Sof(C9)=Sof(H9)=Sof(Cl1)=Sof(C10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=
 Sof(H14)=Sof(C15)=FVAR(1)
7.a Riding coordinates:
 C11(H11), C15(H15), C11B(H11B), C15B(H15B)
7.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C2B(H2B), C3B(H3BA), C6B(H6B), C7B(H7B)
7.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1B(H1BA,H1BB)
7.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C8B(H8B), C9B(H9B), C12(H12), C14(H14), C12B(H12B), C14B(H14B)
;
_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
O1 O 0.02064(10) 0.5542(3) 0.28315(8) 0.0213(4) Uani 0.879(2) 1 d D . P A 1
O2 O 0.18528(10) 0.0848(2) 0.24349(8) 0.0165(4) Uani 0.879(2) 1 d D . P A 1
N1 N 0.10622(12) 0.3435(3) 0.25309(9) 0.0118(4) Uani 0.879(2) 1 d D . P A 1
C1 C 0.14343(15) 0.1513(4) 0.43995(11) 0.0204(5) Uani 0.879(2) 1 d D . P A 1
H1A H 0.102908 0.050674 0.439649 0.024 Uiso 0.879(2) 1 calc R . P A 1
H1B H 0.176506 0.168578 0.482505 0.024 Uiso 0.879(2) 1 calc R . P A 1
C2 C 0.10857(15) 0.3433(4) 0.41008(11) 0.0182(5) Uani 0.879(2) 1 d D . P A 1
H2 H 0.074674 0.416855 0.432802 0.022 Uiso 0.879(2) 1 calc R . P A 1
C3 C 0.0666(2) 0.2640(4) 0.34432(14) 0.0142(5) Uani 0.879(2) 1 d D . P A 1
H3 H 0.014059 0.207173 0.344827 0.017 Uiso 0.879(2) 1 calc R . P A 1
C4 C 0.05963(13) 0.4070(3) 0.29214(10) 0.0140(4) Uani 0.879(2) 1 d D . P A 1
C5 C 0.14401(14) 0.1684(3) 0.27206(11) 0.0119(4) Uani 0.879(2) 1 d D . P A 1
C6 C 0.12312(13) 0.1065(3) 0.33142(10) 0.0138(4) Uani 0.879(2) 1 d D . P A 1
H6 H 0.097192 -0.023777 0.326625 0.017 Uiso 0.879(2) 1 calc R . P A 1
C7 C 0.19243(16) 0.1137(5) 0.39113(13) 0.0179(5) Uani 0.879(2) 1 d D . P A 1
H7 H 0.228165 -0.001642 0.398626 0.021 Uiso 0.879(2) 1 calc R . P A 1
C8 C 0.23183(14) 0.3100(4) 0.39122(11) 0.0189(5) Uani 0.879(2) 1 d D . P A 1
H8 H 0.282731 0.332377 0.384262 0.023 Uiso 0.879(2) 1 calc R . P A 1
C9 C 0.18274(16) 0.4454(5) 0.40272(13) 0.0210(6) Uani 0.879(2) 1 d D . P A 1
H9 H 0.192421 0.581109 0.405753 0.025 Uiso 0.879(2) 1 calc R . P A 1
O1B O 0.1839(8) 0.421(2) 0.2453(6) 0.026(3) Uiso 0.121(2) 1 d D . P A 2
O2B O 0.0203(8) -0.0568(19) 0.2806(7) 0.030(3) Uiso 0.121(2) 1 d D . P A 2
N1B N 0.1066(9) 0.1594(17) 0.2535(6) 0.0118(4) Uani 0.121(2) 1 d D . P A 2
C1B C 0.1406(13) 0.337(3) 0.4375(9) 0.037(5) Uiso 0.121(2) 1 d D . P A 2
H1BA H 0.173665 0.319392 0.480052 0.044 Uiso 0.121(2) 1 calc R . P A 2
H1BB H 0.098760 0.433549 0.437690 0.044 Uiso 0.121(2) 1 calc R . P A 2
C2B C 0.1898(10) 0.386(3) 0.3895(7) 0.017(5) Uiso 0.121(2) 1 d D . P A 2
H2B H 0.224425 0.503316 0.397920 0.020 Uiso 0.121(2) 1 calc R . P A 2
C3B C 0.1195(9) 0.392(2) 0.3313(6) 0.023(4) Uiso 0.121(2) 1 d D . P A 2
H3BA H 0.092892 0.521487 0.327071 0.028 Uiso 0.121(2) 1 calc R . P A 2
C4B C 0.1412(12) 0.335(2) 0.2722(8) 0.021(4) Uiso 0.121(2) 1 d D . P A 2
C5B C 0.0592(10) 0.088(2) 0.2905(7) 0.023(4) Uiso 0.121(2) 1 d D . P A 2
C6B C 0.0635(13) 0.231(3) 0.3427(8) 0.0142(5) Uani 0.121(2) 1 d D . P A 2
H6B H 0.010446 0.282521 0.343974 0.017 Uiso 0.121(2) 1 calc R . P A 2
C7B C 0.1079(11) 0.144(3) 0.4070(9) 0.036(5) Uiso 0.121(2) 1 d D . P A 2
H7B H 0.075664 0.064564 0.429635 0.043 Uiso 0.121(2) 1 calc R . P A 2
C8B C 0.1831(14) 0.051(3) 0.3979(14) 0.037(9) Uiso 0.121(2) 1 d D . P A 2
H8B H 0.194755 -0.083773 0.399565 0.045 Uiso 0.121(2) 1 calc R . P A 2
C9B C 0.2297(10) 0.192(3) 0.3870(8) 0.020(4) Uiso 0.121(2) 1 d D . P A 2
H9B H 0.280318 0.174760 0.378988 0.025 Uiso 0.121(2) 1 calc R . P A 2
Cl1 Cl 0.11323(7) 0.78786(14) 0.02549(4) 0.0311(2) Uani 0.879(2) 1 d D . P A 1
O3A O 0.17370(19) 0.7018(5) 0.26064(14) 0.0128(6) Uani 0.4395(11) 1 d D . P A 1
O3C O 0.0383(2) 0.1976(6) 0.12807(16) 0.0223(8) Uani 0.4395(11) 1 d D . P A 1
C10 C 0.11044(12) 0.4455(3) 0.19766(10) 0.0118(4) Uani 0.879(2) 1 d D . P A 1
C11 C 0.14521(13) 0.6285(3) 0.20282(10) 0.0129(4) Uani 0.879(2) 1 d D . P A 1
H11 H 0.168194 0.681851 0.243043 0.015 Uiso 0.4395(11) 1 d R . P A 1
C12 C 0.14649(18) 0.7335(4) 0.14942(12) 0.0168(6) Uani 0.879(2) 1 d D . P A 1
H12 H 0.169958 0.858543 0.152274 0.020 Uiso 0.879(2) 1 calc R . P A 1
C13 C 0.11305(14) 0.6529(4) 0.09212(11) 0.0173(5) Uani 0.879(2) 1 d D . P A 1
C14 C 0.07844(14) 0.4707(4) 0.08612(11) 0.0176(5) Uani 0.879(2) 1 d D . P A 1
H14 H 0.056261 0.418090 0.046182 0.021 Uiso 0.879(2) 1 calc R . P A 1
C15 C 0.07671(15) 0.3660(3) 0.13956(11) 0.0151(5) Uani 0.879(2) 1 d D . P A 1
H15 H 0.052454 0.240296 0.136475 0.018 Uiso 0.4395(11) 1 d R . P A 1
Cl1B Cl 0.1240(6) -0.2664(12) 0.0303(4) 0.0311(2) Uani 0.121(2) 1 d D . P A 2
O3B O 0.1763(12) -0.194(3) 0.2593(7) 0.018(5) Uiso 0.0726(13) 1 d D . P A 2
O3D O 0.038(2) 0.313(4) 0.1325(14) 0.019(7) Uiso 0.0484(9) 1 d D . P A 2
C10B C 0.1106(8) 0.0580(19) 0.1982(5) 0.021(4) Uiso 0.121(2) 1 d D . P A 2
C11B C 0.1465(9) -0.121(2) 0.2024(6) 0.022(4) Uiso 0.121(2) 1 d D . P A 2
H11B H 0.168783 -0.175735 0.242555 0.027 Uiso 0.0484(9) 1 d R . P A 2
C12B C 0.1506(11) -0.223(3) 0.1497(7) 0.0168(6) Uani 0.121(2) 1 d D . P A 2
H12B H 0.175093 -0.346110 0.151355 0.020 Uiso 0.121(2) 1 calc R . P A 2
C13B C 0.1165(9) -0.133(2) 0.0942(6) 0.029(4) Uiso 0.121(2) 1 d D . P A 2
C14B C 0.0799(9) 0.046(2) 0.0879(7) 0.027(4) Uiso 0.121(2) 1 d D . P A 2
H14B H 0.057550 0.100051 0.048175 0.032 Uiso 0.121(2) 1 calc R . P A 2
C15B C 0.0771(9) 0.144(2) 0.1422(7) 0.027(5) Uiso 0.121(2) 1 d D . P A 2
H15B H 0.052643 0.269482 0.140587 0.033 Uiso 0.0726(13) 1 d R . P A 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
O1 C4 1.212(3) . ?
O2 C5 1.211(3) . ?
N1 C4 1.390(3) . ?
N1 C5 1.392(3) . ?
N1 C10 1.431(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.540(4) . ?
C1 C7 1.550(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.567(4) . ?
C2 C9 1.516(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.502(4) . ?
C3 C6 1.539(4) . ?
C5 C6 1.506(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.570(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.518(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.332(4) . ?
C9 H9 0.9500 . ?
O1B C4B 1.212(12) . ?
O2B C5B 1.198(12) . ?
N1B C4B 1.372(13) . ?
N1B C5B 1.386(12) . ?
N1B C10B 1.424(9) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.552(14) . ?
C1B C7B 1.541(14) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.559(14) . ?
C2B C9B 1.512(14) . ?
C3B H3BA 1.0000 . ?
C3B C4B 1.498(13) . ?
C3B C6B 1.540(14) . ?
C5B C6B 1.505(14) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.571(15) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.515(15) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.327(14) . ?
C9B H9B 0.9500 . ?
Cl1 C13 1.744(2) . ?
O3A C11 1.357(3) . ?
O3A H11 0.4029 . ?
O3C C15 1.335(4) . ?
O3C H15 0.4006 . ?
C10 C11 1.393(3) . ?
C10 C15 1.395(3) . ?
C11 H11 0.9599 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9600 . ?
Cl1B C13B 1.719(12) . ?
O3B C11B 1.343(13) . ?
O3B H11B 0.3849 . ?
O3D C15B 1.338(8) . ?
O3D H15B 0.4050 . ?
C10B C11B 1.378(13) . ?
C10B C15B 1.376(13) . ?
C11B H11B 0.9598 . ?
C11B C12B 1.377(13) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.379(14) . ?
C13B C14B 1.381(13) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.388(13) . ?
C15B H15B 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C5 113.00(19) . . ?
C4 N1 C10 122.30(19) . . ?
C5 N1 C10 124.62(18) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.9 . . ?
C2 C1 H1B 112.9 . . ?
C2 C1 C7 94.1(2) . . ?
C7 C1 H1A 112.9 . . ?
C7 C1 H1B 112.9 . . ?
C1 C2 H2 116.2 . . ?
C1 C2 C3 98.7(2) . . ?
C3 C2 H2 116.2 . . ?
C9 C2 C1 100.5(2) . . ?
C9 C2 H2 116.2 . . ?
C9 C2 C3 106.7(2) . . ?
C2 C3 H3 110.9 . . ?
C4 C3 C2 114.9(2) . . ?
C4 C3 H3 110.9 . . ?
C4 C3 C6 105.1(2) . . ?
C6 C3 C2 103.7(2) . . ?
C6 C3 H3 110.9 . . ?
O1 C4 N1 123.4(2) . . ?
O1 C4 C3 128.1(2) . . ?
N1 C4 C3 108.6(2) . . ?
O2 C5 N1 123.6(2) . . ?
O2 C5 C6 128.1(2) . . ?
N1 C5 C6 108.31(19) . . ?
C3 C6 H6 111.0 . . ?
C3 C6 C7 102.9(2) . . ?
C5 C6 C3 105.0(2) . . ?
C5 C6 H6 111.0 . . ?
C5 C6 C7 115.4(2) . . ?
C7 C6 H6 111.0 . . ?
C1 C7 C6 98.58(19) . . ?
C1 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
C8 C7 C1 100.0(2) . . ?
C8 C7 C6 106.8(2) . . ?
C8 C7 H7 116.3 . . ?
C7 C8 H8 125.9 . . ?
C9 C8 C7 108.2(2) . . ?
C9 C8 H8 125.9 . . ?
C2 C9 H9 126.3 . . ?
C8 C9 C2 107.5(2) . . ?
C8 C9 H9 126.3 . . ?
C4B N1B C5B 114.5(10) . . ?
C4B N1B C10B 125.8(11) . . ?
C5B N1B C10B 119.4(11) . . ?
H1BA C1B H1BB 110.1 . . ?
C2B C1B H1BA 112.6 . . ?
C2B C1B H1BB 112.6 . . ?
C7B C1B H1BA 112.6 . . ?
C7B C1B H1BB 112.6 . . ?
C7B C1B C2B 95.5(11) . . ?
C1B C2B H2B 117.2 . . ?
C1B C2B C3B 96.6(12) . . ?
C3B C2B H2B 117.2 . . ?
C9B C2B C1B 99.6(12) . . ?
C9B C2B H2B 117.2 . . ?
C9B C2B C3B 105.9(13) . . ?
C2B C3B H3BA 111.1 . . ?
C4B C3B C2B 113.8(14) . . ?
C4B C3B H3BA 111.1 . . ?
C4B C3B C6B 104.7(12) . . ?
C6B C3B C2B 104.7(12) . . ?
C6B C3B H3BA 111.1 . . ?
O1B C4B N1B 124.0(13) . . ?
O1B C4B C3B 127.7(13) . . ?
N1B C4B C3B 108.2(10) . . ?
O2B C5B N1B 125.4(14) . . ?
O2B C5B C6B 127.5(14) . . ?
N1B C5B C6B 107.1(11) . . ?
C3B C6B H6B 112.0 . . ?
C3B C6B C7B 103.1(13) . . ?
C5B C6B C3B 105.4(13) . . ?
C5B C6B H6B 112.0 . . ?
C5B C6B C7B 111.8(16) . . ?
C7B C6B H6B 112.0 . . ?
C1B C7B C6B 96.9(13) . . ?
C1B C7B H7B 116.5 . . ?
C6B C7B H7B 116.5 . . ?
C8B C7B C1B 100.3(14) . . ?
C8B C7B C6B 107.4(16) . . ?
C8B C7B H7B 116.5 . . ?
C7B C8B H8B 126.2 . . ?
C9B C8B C7B 107.6(14) . . ?
C9B C8B H8B 126.2 . . ?
C2B C9B H9B 125.2 . . ?
C8B C9B C2B 109.5(14) . . ?
C8B C9B H9B 125.2 . . ?
C11 C10 N1 118.9(2) . . ?
C11 C10 C15 120.9(2) . . ?
C15 C10 N1 120.2(2) . . ?
O3A C11 C10 118.1(2) . . ?
O3A C11 C12 122.2(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 Cl1 118.52(19) . . ?
C12 C13 C14 122.2(2) . . ?
C14 C13 Cl1 119.29(19) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 118.9(2) . . ?
C15 C14 H14 120.5 . . ?
O3C C15 C10 127.0(3) . . ?
O3C C15 C14 113.5(2) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C11B C10B N1B 119.6(12) . . ?
C15B C10B N1B 117.8(12) . . ?
C15B C10B C11B 122.6(11) . . ?
O3B C11B C10B 118.0(15) . . ?
O3B C11B C12B 121.2(15) . . ?
C10B C11B H11B 119.5 . . ?
C12B C11B C10B 120.7(13) . . ?
C12B C11B H11B 119.7 . . ?
C11B C12B H12B 122.3 . . ?
C11B C12B C13B 115.4(15) . . ?
C13B C12B H12B 122.3 . . ?
C12B C13B Cl1B 113.0(11) . . ?
C12B C13B C14B 125.8(13) . . ?
C14B C13B Cl1B 121.2(11) . . ?
C13B C14B H14B 121.4 . . ?
C13B C14B C15B 117.1(13) . . ?
C15B C14B H14B 121.4 . . ?
O3D C15B C10B 127.8(17) . . ?
O3D C15B C14B 113.8(17) . . ?
C10B C15B C14B 118.4(13) . . ?
C10B C15B H15B 120.8 . . ?
C14B C15B H15B 120.8 . . ?

_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_ecv1_130
_database_code_depnum_ccdc_archive 'CCDC 2003346'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2017-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl N O3'
_chemical_formula_sum            'C16 H14 Cl N O3'
_chemical_formula_weight         303.73
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8726(5)
_cell_length_b                   10.9075(5)
_cell_length_c                   12.7229(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1370.07(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1279 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.9598.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0199
_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       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49019
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        30.084
_diffrn_reflns_theta_max         30.084
_diffrn_reflns_theta_min         2.460
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3781
_reflns_number_total             4021
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(13)
_refine_ls_extinction_coef       0.0196(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.029
_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)+(0.0303P)²+0.4545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0655
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_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 0.69350(4) 0.80289(4) 0.80188(3) 0.01829(10) Uani 1 1 d . . . . .
O1 O 0.21116(12) 0.49848(11) 0.52796(10) 0.0193(3) Uani 1 1 d . . . . .
O2 O 0.63149(13) 0.48062(12) 0.37982(11) 0.0220(3) Uani 1 1 d . . . . .
O3 O 0.41046(14) 0.74926(11) 0.46795(10) 0.0172(3) Uani 1 1 d . . . . .
N1 N 0.43246(14) 0.50518(12) 0.47118(11) 0.0136(3) Uani 1 1 d . . . . .
C1 C 0.28625(19) 0.24816(17) 0.24412(14) 0.0216(4) Uani 1 1 d . . . . .
H1A H 0.271536 0.160495 0.227520 0.026 Uiso 1 1 calc R . . . .
H1B H 0.255352 0.300300 0.185113 0.026 Uiso 1 1 calc R . . . .
C2 C 0.22447(18) 0.28632(16) 0.35078(14) 0.0185(3) Uani 1 1 d . . . . .
H2 H 0.124725 0.273254 0.358606 0.022 Uiso 1 1 calc R . . . .
C3 C 0.27342(17) 0.42265(15) 0.35316(13) 0.0160(3) Uani 1 1 d . . . . .
H3 H 0.212216 0.475391 0.309830 0.019 Uiso 1 1 calc R . . . .
C4 C 0.29462(17) 0.47866(14) 0.46059(13) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.51002(18) 0.46891(14) 0.38438(13) 0.0154(3) Uani 1 1 d . . . . .
C6 C 0.41551(17) 0.41606(14) 0.30326(14) 0.0158(3) Uani 1 1 d . . . . .
H6 H 0.418772 0.465423 0.237079 0.019 Uiso 1 1 calc R . . . .
C7 C 0.43299(18) 0.27626(15) 0.27848(13) 0.0169(3) Uani 1 1 d . . . . .
H7 H 0.505622 0.254649 0.226921 0.020 Uiso 1 1 calc R . . . .
C8 C 0.43752(18) 0.20927(15) 0.38315(13) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.514652 0.170673 0.413119 0.021 Uiso 1 1 calc R . . . .
C9 C 0.31412(19) 0.21424(14) 0.42550(13) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.287203 0.179099 0.490551 0.021 Uiso 1 1 calc R . . . .
C10 C 0.48858(17) 0.57467(15) 0.55574(13) 0.0134(3) Uani 1 1 d . . . . .
C11 C 0.47970(15) 0.70286(16) 0.55041(12) 0.0131(3) Uani 1 1 d . . . . .
C12 C 0.54222(16) 0.77338(14) 0.62806(13) 0.0136(3) Uani 1 1 d . . . . .
H12 H 0.538468 0.860372 0.625782 0.016 Uiso 1 1 calc R . . . .
C13 C 0.60987(16) 0.71358(14) 0.70854(13) 0.0135(3) Uani 1 1 d . . . . .
C14 C 0.61661(17) 0.58722(15) 0.71704(13) 0.0157(3) Uani 1 1 d . . . . .
H14 H 0.661377 0.549012 0.774448 0.019 Uiso 1 1 calc R . . . .
C15 C 0.55511(17) 0.51810(14) 0.63802(13) 0.0155(3) Uani 1 1 d . . . . .
H15 H 0.559048 0.431143 0.640847 0.019 Uiso 1 1 calc R . . . .
C16 C 0.39331(19) 0.87990(15) 0.46383(15) 0.0186(3) Uani 1 1 d . . . . .
H16A H 0.344665 0.902087 0.399439 0.028 Uiso 1 1 calc GR . . . .
H16B H 0.482324 0.919667 0.464123 0.028 Uiso 1 1 calc GR . . . .
H16C H 0.341242 0.907110 0.525121 0.028 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 C13 1.7439(16) . ?
O1 C4 1.208(2) . ?
O2 C5 1.207(2) . ?
O3 C11 1.351(2) . ?
O3 C16 1.436(2) . ?
N1 C4 1.398(2) . ?
N1 C5 1.401(2) . ?
N1 C10 1.428(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.545(3) . ?
C1 C7 1.544(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.564(2) . ?
C2 C9 1.518(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.512(2) . ?
C3 C6 1.541(2) . ?
C5 C6 1.506(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.567(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.520(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.333(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(2) . ?
C10 C15 1.381(2) . ?
C11 C12 1.396(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 C14 1.384(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.396(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C11 O3 C16 117.38(14) . . ?
C4 N1 C5 113.44(13) . . ?
C4 N1 C10 124.07(13) . . ?
C5 N1 C10 122.12(14) . . ?
H1A C1 H1B 110.4 . . ?
C2 C1 H1A 112.9 . . ?
C2 C1 H1B 112.9 . . ?
C7 C1 H1A 112.9 . . ?
C7 C1 H1B 112.9 . . ?
C7 C1 C2 93.92(13) . . ?
C1 C2 H2 116.0 . . ?
C1 C2 C3 98.70(14) . . ?
C3 C2 H2 116.0 . . ?
C9 C2 C1 100.39(14) . . ?
C9 C2 H2 116.0 . . ?
C9 C2 C3 107.46(13) . . ?
C2 C3 H3 110.5 . . ?
C4 C3 C2 116.40(14) . . ?
C4 C3 H3 110.5 . . ?
C4 C3 C6 105.38(14) . . ?
C6 C3 C2 103.23(13) . . ?
C6 C3 H3 110.5 . . ?
O1 C4 N1 123.95(15) . . ?
O1 C4 C3 128.26(15) . . ?
N1 C4 C3 107.79(14) . . ?
O2 C5 N1 123.43(16) . . ?
O2 C5 C6 128.53(16) . . ?
N1 C5 C6 108.04(14) . . ?
C3 C6 H6 110.5 . . ?
C3 C6 C7 103.21(13) . . ?
C5 C6 C3 105.29(14) . . ?
C5 C6 H6 110.5 . . ?
C5 C6 C7 116.25(14) . . ?
C7 C6 H6 110.5 . . ?
C1 C7 C6 98.44(14) . . ?
C1 C7 H7 116.1 . . ?
C6 C7 H7 116.1 . . ?
C8 C7 C1 100.38(14) . . ?
C8 C7 C6 107.14(13) . . ?
C8 C7 H7 116.1 . . ?
C7 C8 H8 126.0 . . ?
C9 C8 C7 107.92(15) . . ?
C9 C8 H8 126.0 . . ?
C2 C9 H9 126.3 . . ?
C8 C9 C2 107.50(15) . . ?
C8 C9 H9 126.3 . . ?
C11 C10 N1 117.93(14) . . ?
C15 C10 N1 121.22(14) . . ?
C15 C10 C11 120.78(15) . . ?
O3 C11 C10 116.28(14) . . ?
O3 C11 C12 124.54(15) . . ?
C12 C11 C10 119.17(14) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.47(14) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 Cl1 117.93(12) . . ?
C14 C13 Cl1 118.70(13) . . ?
C14 C13 C12 123.35(15) . . ?
C13 C14 H14 121.3 . . ?
C13 C14 C15 117.43(15) . . ?
C15 C14 H14 121.3 . . ?
C10 C15 C14 120.76(15) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C13 C14 C15 -176.52(12) . . . . ?
O2 C5 C6 C3 178.96(17) . . . . ?
O2 C5 C6 C7 65.4(2) . . . . ?
O3 C11 C12 C13 179.90(15) . . . . ?
N1 C5 C6 C3 -1.22(17) . . . . ?
N1 C5 C6 C7 -114.73(16) . . . . ?
N1 C10 C11 O3 4.1(2) . . . . ?
N1 C10 C11 C12 -175.41(14) . . . . ?
N1 C10 C15 C14 176.14(15) . . . . ?
C1 C2 C3 C4 -151.92(14) . . . . ?
C1 C2 C3 C6 -37.03(15) . . . . ?
C1 C2 C9 C8 33.65(17) . . . . ?
C1 C7 C8 C9 -32.37(17) . . . . ?
C2 C1 C7 C6 -60.06(15) . . . . ?
C2 C1 C7 C8 49.22(14) . . . . ?
C2 C3 C4 O1 -64.6(2) . . . . ?
C2 C3 C4 N1 115.24(15) . . . . ?
C2 C3 C6 C5 -122.78(14) . . . . ?
C2 C3 C6 C7 -0.42(16) . . . . ?
C3 C2 C9 C8 -69.00(17) . . . . ?
C3 C6 C7 C1 37.73(16) . . . . ?
C3 C6 C7 C8 -65.95(17) . . . . ?
C4 N1 C5 O2 -177.79(16) . . . . ?
C4 N1 C5 C6 2.38(18) . . . . ?
C4 N1 C10 C11 -80.4(2) . . . . ?
C4 N1 C10 C15 102.49(19) . . . . ?
C4 C3 C6 C5 -0.20(16) . . . . ?
C4 C3 C6 C7 122.15(14) . . . . ?
C5 N1 C4 O1 177.30(15) . . . . ?
C5 N1 C4 C3 -2.51(18) . . . . ?
C5 N1 C10 C11 92.18(19) . . . . ?
C5 N1 C10 C15 -84.9(2) . . . . ?
C5 C6 C7 C1 152.43(15) . . . . ?
C5 C6 C7 C8 48.75(19) . . . . ?
C6 C3 C4 O1 -178.23(16) . . . . ?
C6 C3 C4 N1 1.56(16) . . . . ?
C6 C7 C8 C9 69.91(17) . . . . ?
C7 C1 C2 C3 59.91(14) . . . . ?
C7 C1 C2 C9 -49.77(15) . . . . ?
C7 C8 C9 C2 -0.79(18) . . . . ?
C9 C2 C3 C4 -48.1(2) . . . . ?
C9 C2 C3 C6 66.83(17) . . . . ?
C10 N1 C4 O1 -9.5(2) . . . . ?
C10 N1 C4 C3 170.67(14) . . . . ?
C10 N1 C5 O2 8.9(3) . . . . ?
C10 N1 C5 C6 -170.95(14) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C10 C15 C14 -0.9(2) . . . . ?
C11 C12 C13 Cl1 177.35(12) . . . . ?
C11 C12 C13 C14 -1.2(2) . . . . ?
C12 C13 C14 C15 2.0(3) . . . . ?
C13 C14 C15 C10 -1.0(2) . . . . ?
C15 C10 C11 O3 -178.83(15) . . . . ?
C15 C10 C11 C12 1.7(2) . . . . ?
C16 O3 C11 C10 176.56(15) . . . . ?
C16 O3 C11 C12 -4.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
