# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ll_1
_database_code_depnum_ccdc_archive 'CCDC 1864355'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 Cl N2 O5'
_chemical_formula_sum            'C18 H15 Cl N2 O5'
_chemical_formula_weight         374.77
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   11.0671(2)
_cell_length_b                   11.0671(2)
_cell_length_c                   11.8214(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1253.91(5)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    7554
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.4300
_cell_measurement_theta_min      3.6980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             582
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8112
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.496
_diffrn_reflns_theta_min         4.614
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  29.00   1.00    1.00    --  -40.98  57.00 -30.00   96
  2  ω    -34.00  -7.00   1.00    1.00    --  -40.98 125.00 -30.00   27
  3  ω    -60.00  26.00   1.00    1.00    --  -40.98  57.00-150.00   86
  4  ω     58.00  89.00   1.00    1.00    --   40.98-125.00   0.00   31
  5  ω     29.00 107.00   1.00    1.00    --  106.95 -94.00 120.00   78
  6  ω     49.00 121.00   1.00    1.00    --  106.95-125.00  60.00   72
  7  ω     33.00 118.00   1.00    1.00    --  106.95 -30.00  60.00   85
  8  ω     63.00 152.00   1.00    1.00    --  106.95  15.00   0.00   89
  9  ω     79.00 177.00   1.00    1.00    --  106.95  30.00-120.00   98
 10  ω    107.00 133.00   1.00    1.00    --  106.95 -45.00-150.00   26
 11  ω     48.00 108.00   1.00    1.00    --  106.95 -94.00-180.00   60
 12  ω     37.00  89.00   1.00    1.00    --  106.95 -45.00-150.00   52
 13  ω     37.00 139.00   1.00    1.00    --  106.95 -77.00-150.00  102
 14  ω     99.00 133.00   1.00    1.00    --  106.95 125.00 150.00   34
 15  ω    109.00 177.00   1.00    1.00    --  106.95 125.00-180.00   68
 16  ω   -111.00 -39.00   1.00    1.00    --  -40.98 -57.00  60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0640565000
_diffrn_orient_matrix_UB_12      0.1424881000
_diffrn_orient_matrix_UB_13      0.0599878000
_diffrn_orient_matrix_UB_21      -0.0288654000
_diffrn_orient_matrix_UB_22      -0.0735747000
_diffrn_orient_matrix_UB_23      0.1155264000
_diffrn_orient_matrix_UB_31      0.1447069000
_diffrn_orient_matrix_UB_32      0.0117197000
_diffrn_orient_matrix_UB_33      -0.0036682000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                3087
_reflns_number_total             3098
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1402 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.033
_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)+(0.0608P)²+0.1076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0785
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C12(H12), C3(H3), C5(H5), C4(H4), C16(H16), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.48205(6) 0.79278(6) 0.74310(5) 0.02566(16) Uani 1 1 d . . . . .
O1 O 0.54994(16) 0.43678(16) 0.52390(13) 0.0154(3) Uani 1 1 d . . . . .
O4 O 0.1261(2) 0.2038(2) 0.46076(17) 0.0303(4) Uani 1 1 d . . . . .
O5 O 0.13319(18) 0.08026(19) 0.31238(15) 0.0240(4) Uani 1 1 d . . . . .
O3 O 0.70545(19) 0.5147(2) 0.25708(14) 0.0277(4) Uani 1 1 d . . . . .
O2 O 0.79099(19) 0.5562(2) 0.42549(16) 0.0308(4) Uani 1 1 d . . . . .
N1 N 0.6941(2) 0.5105(2) 0.35987(16) 0.0176(4) Uani 1 1 d . . . . .
N2 N 0.3340(2) 0.4457(2) 0.3696(2) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.3663(2) 0.0669(2) 0.4688(2) 0.0198(4) Uani 1 1 d . . . . .
H2A H 0.326097 0.008335 0.406861 0.024 Uiso 1 1 calc R . . . .
C12 C 0.4886(2) 0.6707(2) 0.5467(2) 0.0185(4) Uani 1 1 d . . . . .
H12 H 0.429022 0.586510 0.582194 0.022 Uiso 1 1 calc R . . . .
C1 C 0.4298(2) 0.2108(2) 0.45706(19) 0.0161(4) Uani 1 1 d . . . . .
C6 C 0.4909(2) 0.2954(2) 0.55032(19) 0.0153(4) Uani 1 1 d . . . . .
C3 C 0.3643(3) 0.0123(3) 0.5754(2) 0.0217(5) Uani 1 1 d . . . . .
H3 H 0.321463 -0.083778 0.585070 0.026 Uiso 1 1 calc R . . . .
C7 C 0.5447(2) 0.4475(2) 0.40582(18) 0.0151(4) Uani 1 1 d . . . . .
C17 C 0.1793(2) 0.1944(2) 0.3748(2) 0.0198(5) Uani 1 1 d . . . . .
C11 C 0.5323(2) 0.6728(2) 0.4360(2) 0.0187(5) Uani 1 1 d . . . . .
C5 C 0.4915(2) 0.2455(2) 0.65674(19) 0.0169(4) Uani 1 1 d . . . . .
H5 H 0.533340 0.304883 0.717914 0.020 Uiso 1 1 calc R . . . .
C13 C 0.5348(2) 0.7957(3) 0.6033(2) 0.0213(5) Uani 1 1 d . . . . .
C8 C 0.4454(2) 0.3014(2) 0.35731(18) 0.0165(4) Uani 1 1 d . . . . .
H8 H 0.485097 0.280062 0.291383 0.020 Uiso 1 1 calc R . . . .
C10 C 0.4839(2) 0.5410(2) 0.36849(19) 0.0182(4) Uani 1 1 d . . . . .
H10 H 0.511700 0.568175 0.289691 0.022 Uiso 1 1 calc R . . . .
C4 C 0.4258(2) 0.1003(2) 0.6678(2) 0.0192(5) Uani 1 1 d . . . . .
H4 H 0.423050 0.061741 0.738287 0.023 Uiso 1 1 calc R . . . .
C16 C 0.6231(3) 0.8002(3) 0.3853(2) 0.0241(5) Uani 1 1 d . . . . .
H16 H 0.654046 0.802287 0.311839 0.029 Uiso 1 1 calc R . . . .
C9 C 0.3123(2) 0.3129(2) 0.3257(2) 0.0183(4) Uani 1 1 d . . . . .
H9 H 0.303612 0.312331 0.243201 0.022 Uiso 1 1 calc R . . . .
C15 C 0.6676(3) 0.9244(3) 0.4441(3) 0.0311(6) Uani 1 1 d . . . . .
H15 H 0.727953 1.008969 0.409399 0.037 Uiso 1 1 calc R . . . .
C14 C 0.6233(3) 0.9234(3) 0.5530(3) 0.0271(5) Uani 1 1 d . . . . .
H14 H 0.651977 1.006354 0.592053 0.033 Uiso 1 1 calc R . . . .
C18 C 0.0095(3) -0.0427(3) 0.3544(3) 0.0343(6) Uani 1 1 d . . . . .
H18A H -0.030451 -0.110736 0.295068 0.051 Uiso 1 1 calc GR . . . .
H18B H -0.057331 -0.017321 0.379352 0.051 Uiso 1 1 calc GR . . . .
H18C H 0.034640 -0.081474 0.416690 0.051 Uiso 1 1 calc GR . . . .
H2 H 0.301(3) 0.435(3) 0.432(3) 0.018(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.748(3) . ?
O1 C6 1.397(3) . ?
O1 C7 1.405(3) . ?
O4 C17 1.205(3) . ?
O5 C17 1.325(3) . ?
O5 C18 1.453(3) . ?
O3 N1 1.220(3) . ?
O2 N1 1.210(3) . ?
N1 C7 1.537(3) . ?
N2 C10 1.454(3) . ?
N2 C9 1.461(3) . ?
N2 H2 0.80(4) . ?
C2 H2A 0.9300 . ?
C2 C1 1.389(3) . ?
C2 C3 1.393(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.392(3) . ?
C12 C13 1.383(3) . ?
C1 C6 1.384(3) . ?
C1 C8 1.501(3) . ?
C6 C5 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(3) . ?
C7 C8 1.541(3) . ?
C7 C10 1.553(3) . ?
C17 C9 1.514(3) . ?
C11 C10 1.507(3) . ?
C11 C16 1.393(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.400(3) . ?
C13 C14 1.388(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.585(3) . ?
C10 H10 0.9800 . ?
C4 H4 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.392(4) . ?
C9 H9 0.9800 . ?
C15 H15 0.9300 . ?
C15 C14 1.376(4) . ?
C14 H14 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C6 O1 C7 107.53(16) . . ?
C17 O5 C18 115.9(2) . . ?
O3 N1 C7 115.86(18) . . ?
O2 N1 O3 124.7(2) . . ?
O2 N1 C7 119.36(18) . . ?
C10 N2 C9 106.25(19) . . ?
C10 N2 H2 113(2) . . ?
C9 N2 H2 110(2) . . ?
C1 C2 H2A 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 H2A 120.8 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C13 C12 C11 119.1(2) . . ?
C2 C1 C8 131.9(2) . . ?
C6 C1 C2 119.5(2) . . ?
C6 C1 C8 108.62(19) . . ?
C1 C6 O1 112.11(19) . . ?
C5 C6 O1 124.1(2) . . ?
C5 C6 C1 123.8(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
O1 C7 N1 108.00(16) . . ?
O1 C7 C8 108.60(17) . . ?
O1 C7 C10 112.88(18) . . ?
N1 C7 C8 112.66(17) . . ?
N1 C7 C10 108.89(18) . . ?
C8 C7 C10 105.88(18) . . ?
O4 C17 O5 125.5(2) . . ?
O4 C17 C9 123.6(2) . . ?
O5 C17 C9 110.9(2) . . ?
C12 C11 C10 122.0(2) . . ?
C12 C11 C16 119.3(2) . . ?
C16 C11 C10 118.7(2) . . ?
C6 C5 H5 121.9 . . ?
C6 C5 C4 116.2(2) . . ?
C4 C5 H5 121.9 . . ?
C12 C13 Cl1 119.04(19) . . ?
C12 C13 C14 122.1(2) . . ?
C14 C13 Cl1 118.9(2) . . ?
C1 C8 C7 101.09(17) . . ?
C1 C8 H8 112.3 . . ?
C1 C8 C9 115.95(18) . . ?
C7 C8 H8 112.3 . . ?
C7 C8 C9 101.99(17) . . ?
C9 C8 H8 112.3 . . ?
N2 C10 C7 103.40(18) . . ?
N2 C10 C11 114.9(2) . . ?
N2 C10 H10 107.5 . . ?
C7 C10 H10 107.5 . . ?
C11 C10 C7 115.56(18) . . ?
C11 C10 H10 107.5 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
N2 C9 C17 109.6(2) . . ?
N2 C9 C8 107.75(17) . . ?
N2 C9 H9 109.0 . . ?
C17 C9 C8 112.34(19) . . ?
C17 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.7 . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.4(2) . . ?
C15 C14 H14 120.8 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.700
_oxdiff_exptl_absorpt_empirical_full_min 0.650
