# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1565650'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 Cl N O8'
_chemical_formula_weight         443.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8909(4)
_cell_length_b                   11.4787(6)
_cell_length_c                   13.1419(7)
_cell_angle_alpha                76.205(4)
_cell_angle_beta                 89.221(4)
_cell_angle_gamma                85.231(4)
_cell_volume                     1006.01(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1025
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      22.32

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6163
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13968
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         25.055
_diffrn_reflns_theta_full        25.055
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3562
_reflns_number_gt                2267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0951P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3562
_refine_ls_number_parameters     295
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1443
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3779(6) -0.5607(3) 0.7985(3) 0.0239(9) Uani 1 1 d . . . . .
H1A H 0.519715 -0.583898 0.800483 0.029 Uiso 1 1 calc R U . . .
H1B H 0.307957 -0.634793 0.812840 0.029 Uiso 1 1 calc R U . . .
C2 C 0.3061(5) -0.3736(3) 0.8184(3) 0.0190(8) Uani 1 1 d . . . . .
C3 C 0.2844(5) -0.2716(3) 0.8557(3) 0.0194(8) Uani 1 1 d . . . . .
H3 H 0.285456 -0.275432 0.928694 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2607(5) -0.1612(3) 0.7813(3) 0.0194(8) Uani 1 1 d . . . . .
C5 C 0.2531(5) -0.0440(3) 0.8154(3) 0.0210(9) Uani 1 1 d . . . . .
H5A H 0.201560 -0.056620 0.887559 0.025 Uiso 1 1 calc R U . . .
H5B H 0.386619 -0.018299 0.816130 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1260(5) 0.0539(3) 0.7431(3) 0.0207(9) Uani 1 1 d . . . . .
H6A H -0.012008 0.036044 0.752984 0.025 Uiso 1 1 calc R U . . .
H6B H 0.140030 0.131817 0.761014 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1646(5) 0.1728(3) 0.5670(3) 0.0179(8) Uani 1 1 d . . . . .
H7 H 0.130178 0.240833 0.594754 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1973(5) 0.1893(3) 0.4593(3) 0.0160(8) Uani 1 1 d . . . . .
C9 C 0.1761(5) 0.3051(3) 0.3898(3) 0.0186(8) Uani 1 1 d . . . . .
C10 C 0.1999(5) 0.3155(3) 0.2834(3) 0.0180(8) Uani 1 1 d . . . . .
C11 C 0.2515(5) 0.2119(3) 0.2450(3) 0.0177(8) Uani 1 1 d . . . . .
H11 H 0.267228 0.219903 0.171788 0.021 Uiso 1 1 calc R U . . .
C12 C 0.2790(5) 0.1001(3) 0.3121(3) 0.0185(8) Uani 1 1 d . . . . .
H12 H 0.317722 0.032092 0.285089 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2507(5) 0.0852(3) 0.4202(3) 0.0170(8) Uani 1 1 d . . . . .
C14 C 0.2708(5) -0.0270(3) 0.4924(3) 0.0156(8) Uani 1 1 d . . . . .
H14 H 0.310032 -0.096562 0.467581 0.019 Uiso 1 1 calc R U . . .
C15 C 0.2361(5) -0.0402(3) 0.5967(3) 0.0179(8) Uani 1 1 d . . . . .
C16 C 0.2549(5) -0.1571(3) 0.6745(3) 0.0174(8) Uani 1 1 d . . . . .
C17 C 0.2768(5) -0.2637(3) 0.6386(3) 0.0193(8) Uani 1 1 d . . . . .
H17 H 0.273468 -0.261888 0.565975 0.023 Uiso 1 1 calc R U . . .
C18 C 0.3031(5) -0.3696(3) 0.7125(3) 0.0186(8) Uani 1 1 d . . . . .
C19 C 0.2739(5) 0.4549(3) 0.4696(3) 0.0252(9) Uani 1 1 d . . . . .
H19A H 0.221011 0.524954 0.494606 0.038 Uiso 1 1 calc R U . . .
H19B H 0.336038 0.394535 0.528099 0.038 Uiso 1 1 calc R U . . .
H19C H 0.370323 0.479940 0.414971 0.038 Uiso 1 1 calc R U . . .
C20 C 0.1822(6) 0.4423(4) 0.1090(3) 0.0243(9) Uani 1 1 d . . . . .
H20A H 0.158405 0.527632 0.073620 0.036 Uiso 1 1 calc R U . . .
H20B H 0.312122 0.412127 0.090809 0.036 Uiso 1 1 calc R U . . .
H20C H 0.083973 0.396528 0.086481 0.036 Uiso 1 1 calc R U . . .
Cl1 Cl 0.40322(15) 0.77482(9) 0.33064(8) 0.0288(3) Uani 1 1 d . . . . .
N1 N 0.1809(4) 0.0632(3) 0.6314(2) 0.0167(7) Uani 1 1 d . . . . .
O1 O 0.3269(4) -0.4911(2) 0.87526(18) 0.0213(6) Uani 1 1 d . . . . .
O2 O 0.3213(4) -0.4845(2) 0.69792(19) 0.0223(6) Uani 1 1 d . . . . .
O3 O 0.1169(3) 0.4036(2) 0.42685(18) 0.0191(6) Uani 1 1 d . . . . .
O4 O 0.1706(4) 0.4285(2) 0.22133(18) 0.0212(6) Uani 1 1 d . . . . .
O5 O 0.0277(4) 0.6562(2) 0.2850(2) 0.0279(7) Uani 1 1 d D . . . .
O6 O 0.0302(4) 0.7546(3) 0.0706(2) 0.0356(7) Uani 1 1 d D . . . .
O7 O 0.3377(4) 0.8817(3) 0.0964(2) 0.0385(8) Uani 1 1 d D . . . .
O8 O -0.3172(4) 0.8679(3) -0.0163(2) 0.0376(8) Uani 1 1 d D . . . .
H8B H -0.307(6) 0.9407(14) -0.046(3) 0.045 Uiso 1 1 d D U . . .
H6C H 0.017(5) 0.719(4) 0.1341(13) 0.045 Uiso 1 1 d D U . . .
H8A H -0.421(4) 0.863(3) 0.018(3) 0.045 Uiso 1 1 d D U . . .
H6D H -0.082(3) 0.785(4) 0.049(3) 0.045 Uiso 1 1 d D U . . .
H5C H 0.036(5) 0.5813(10) 0.306(3) 0.045 Uiso 1 1 d D U . . .
H5D H 0.136(3) 0.680(3) 0.295(3) 0.045 Uiso 1 1 d D U . . .
H7A H 0.371(6) 0.863(4) 0.1598(12) 0.045 Uiso 1 1 d D U . . .
H7B H 0.240(4) 0.845(4) 0.091(3) 0.045 Uiso 1 1 d D U . . .


_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
C1 O2 1.438(4) . ?
C1 O1 1.453(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.370(5) . ?
C2 O1 1.373(4) . ?
C2 C18 1.382(5) . ?
C3 C4 1.402(5) . ?
C3 H3 0.9500 . ?
C4 C16 1.394(5) . ?
C4 C5 1.513(5) . ?
C5 C6 1.511(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.493(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.335(4) . ?
C7 C8 1.400(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(5) . ?
C8 C13 1.429(5) . ?
C9 O3 1.364(4) . ?
C9 C10 1.383(5) . ?
C10 O4 1.358(4) . ?
C10 C11 1.417(5) . ?
C11 C12 1.373(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(5) . ?
C14 C15 1.363(5) . ?
C14 H14 0.9500 . ?
C15 N1 1.392(5) . ?
C15 C16 1.477(5) . ?
C16 C17 1.410(5) . ?
C17 C18 1.364(5) . ?
C17 H17 0.9500 . ?
C18 O2 1.373(4) . ?
C19 O3 1.454(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O4 1.449(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O5 H5C 0.836(10) . ?
O5 H5D 0.840(10) . ?
O6 H6C 0.844(10) . ?
O6 H6D 0.843(10) . ?
O7 H7A 0.840(10) . ?
O7 H7B 0.834(10) . ?
O8 H8B 0.844(10) . ?
O8 H8A 0.840(10) . ?

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
O2 C1 O1 106.4(3) . . ?
O2 C1 H1A 110.5 . . ?
O1 C1 H1A 110.5 . . ?
O2 C1 H1B 110.5 . . ?
O1 C1 H1B 110.5 . . ?
H1A C1 H1B 108.6 . . ?
C3 C2 O1 127.8(3) . . ?
C3 C2 C18 122.1(3) . . ?
O1 C2 C18 110.0(3) . . ?
C2 C3 C4 117.1(3) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C16 C4 C3 120.9(3) . . ?
C16 C4 C5 118.6(3) . . ?
C3 C4 C5 120.4(3) . . ?
C6 C5 C4 111.6(3) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C5 111.0(3) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C8 121.3(3) . . ?
N1 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 121.7(3) . . ?
C7 C8 C13 117.9(3) . . ?
C9 C8 C13 120.3(3) . . ?
O3 C9 C10 120.4(3) . . ?
O3 C9 C8 120.1(3) . . ?
C10 C9 C8 119.3(3) . . ?
O4 C10 C9 116.1(3) . . ?
O4 C10 C11 123.8(3) . . ?
C9 C10 C11 120.1(3) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 123.4(3) . . ?
C12 C13 C8 118.5(3) . . ?
C14 C13 C8 118.0(3) . . ?
C15 C14 C13 122.6(3) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C14 C15 N1 117.6(3) . . ?
C14 C15 C16 123.8(3) . . ?
N1 C15 C16 118.5(3) . . ?
C4 C16 C17 120.7(3) . . ?
C4 C16 C15 120.4(3) . . ?
C17 C16 C15 118.8(3) . . ?
C18 C17 C16 117.1(3) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
C17 C18 O2 128.2(3) . . ?
C17 C18 C2 122.0(3) . . ?
O2 C18 C2 109.7(3) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N1 C15 122.5(3) . . ?
C7 N1 C6 117.2(3) . . ?
C15 N1 C6 120.2(3) . . ?
C2 O1 C1 104.8(3) . . ?
C18 O2 C1 105.4(3) . . ?
C9 O3 C19 113.9(3) . . ?
C10 O4 C20 117.8(3) . . ?
H5C O5 H5D 108(2) . . ?
H6C O6 H6D 106(2) . . ?
H7A O7 H7B 107(2) . . ?
H8B O8 H8A 109(2) . . ?

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1811915'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Cl N O6'
_chemical_formula_weight         407.83

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'
'-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                   27.449(7)
_cell_length_b                   7.0744(17)
_cell_length_c                   21.677(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.695(7)
_cell_angle_gamma                90
_cell_volume                     3727.1(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2553
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      24.02

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13186
_diffrn_reflns_av_unetI/netI     0.1479
_diffrn_reflns_av_R_equivalents  0.1303
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3291
_reflns_number_gt                1742
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3291
_refine_ls_number_parameters     265
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.47334(16) 0.1658(6) 0.3224(2) 0.0364(12) Uani 1 1 d . . . . .
H1A H 0.443659 0.085390 0.287914 0.044 Uiso 1 1 calc R U . . .
H1B H 0.462534 0.299883 0.311168 0.044 Uiso 1 1 calc R U . . .
C2 C 0.53823(15) 0.1024(5) 0.4317(2) 0.0213(10) Uani 1 1 d . . . . .
C3 C 0.56817(15) 0.0801(5) 0.5024(2) 0.0211(10) Uani 1 1 d . . . . .
H3 H 0.550942 0.077261 0.531599 0.025 Uiso 1 1 calc R U . . .
C4 C 0.62506(15) 0.0617(5) 0.52964(19) 0.0172(9) Uani 1 1 d . . . . .
C5 C 0.66038(14) 0.0308(5) 0.60630(17) 0.0193(10) Uani 1 1 d . . . . .
H5A H 0.664859 -0.106437 0.616292 0.023 Uiso 1 1 calc R U . . .
H5B H 0.642342 0.086762 0.632331 0.023 Uiso 1 1 calc R U . . .
C6 C 0.71600(14) 0.1205(5) 0.62978(18) 0.0199(10) Uani 1 1 d . . . . .
H6A H 0.711903 0.259662 0.625896 0.024 Uiso 1 1 calc R U . . .
H6B H 0.740113 0.088826 0.679295 0.024 Uiso 1 1 calc R U . . .
C7 C 0.79537(15) 0.0202(5) 0.61771(19) 0.0171(9) Uani 1 1 d . . . . .
H7 H 0.815308 0.026275 0.667082 0.021 Uiso 1 1 calc R U . . .
C8 C 0.82358(15) -0.0239(5) 0.57998(18) 0.0148(9) Uani 1 1 d . . . . .
C9 C 0.88076(15) -0.0528(5) 0.61357(18) 0.0156(9) Uani 1 1 d . . . . .
C10 C 0.90764(16) -0.0846(5) 0.5742(2) 0.0217(10) Uani 1 1 d . . . . .
C11 C 0.87700(16) -0.0926(5) 0.50101(19) 0.0195(10) Uani 1 1 d . . . . .
H11 H 0.895748 -0.114537 0.474262 0.023 Uiso 1 1 calc R U . . .
C12 C 0.82161(15) -0.0700(5) 0.46757(19) 0.0186(10) Uani 1 1 d . . . . .
H12 H 0.802143 -0.079187 0.418229 0.022 Uiso 1 1 calc R U . . .
C13 C 0.79278(15) -0.0328(5) 0.50573(18) 0.0139(9) Uani 1 1 d . . . . .
C14 C 0.73592(16) -0.0032(5) 0.47594(19) 0.0203(10) Uani 1 1 d . . . . .
H14 H 0.714693 -0.013344 0.426792 0.024 Uiso 1 1 calc R U . . .
C15 C 0.70935(14) 0.0399(5) 0.51467(18) 0.0146(9) Uani 1 1 d . . . . .
C16 C 0.64985(15) 0.0697(5) 0.48598(19) 0.0166(9) Uani 1 1 d . . . . .
C17 C 0.61781(15) 0.0951(5) 0.41321(19) 0.0207(10) Uani 1 1 d . . . . .
H17 H 0.634122 0.101650 0.383044 0.025 Uiso 1 1 calc R U . . .
C18 C 0.56300(16) 0.1094(5) 0.38892(19) 0.0229(10) Uani 1 1 d . . . . .
C19 C 0.92471(16) -0.2059(6) 0.72201(19) 0.0378(12) Uani 1 1 d . . . . .
H19A H 0.944666 -0.179718 0.772102 0.057 Uiso 1 1 calc R U . . .
H19B H 0.891703 -0.280263 0.711822 0.057 Uiso 1 1 calc R U . . .
H19C H 0.948480 -0.277186 0.707861 0.057 Uiso 1 1 calc R U . . .
C20 C 0.99353(15) -0.1000(6) 0.5705(2) 0.0284(11) Uani 1 1 d . . . . .
H20A H 1.032975 -0.113216 0.602043 0.043 Uiso 1 1 calc R U . . .
H20B H 0.981147 -0.205348 0.537342 0.043 Uiso 1 1 calc R U . . .
H20C H 0.986785 0.019634 0.545051 0.043 Uiso 1 1 calc R U . . .
Cl1 Cl 0.83893(4) 1.03955(14) 0.80869(5) 0.0272(3) Uani 1 1 d . . . . .
N1 N 0.74189(12) 0.0536(4) 0.58697(15) 0.0167(8) Uani 1 1 d . . . . .
O1 O 0.48220(10) 0.1218(4) 0.39297(14) 0.0323(8) Uani 1 1 d . . . . .
O2 O 0.52374(10) 0.1302(4) 0.32052(13) 0.0323(8) Uani 1 1 d . . . . .
O3 O 0.90906(9) -0.0315(4) 0.68444(12) 0.0225(7) Uani 1 1 d . . . . .
O4 O 0.96367(10) -0.1017(4) 0.61031(13) 0.0280(7) Uani 1 1 d . . . . .
O5 O 0.83597(13) 0.3921(4) 0.70828(15) 0.0369(8) Uani 1 1 d D . . . .
H19 H 0.8160(13) 0.481(4) 0.7102(18) 0.044 Uiso 1 1 d D U . . .
H20 H 0.8413(15) 0.314(4) 0.7397(15) 0.044 Uiso 1 1 d D U . . .
O6 O 0.77442(11) 0.7025(4) 0.70711(14) 0.0301(8) Uani 1 1 d D . . . .
H21 H 0.7893(12) 0.783(4) 0.7385(14) 0.036 Uiso 1 1 d D U . . .
H22 H 0.7458(9) 0.662(5) 0.7066(18) 0.036 Uiso 1 1 d D U . . .


_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
C1 O2 1.426(4) . ?
C1 O1 1.466(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.370(5) . ?
C2 O1 1.374(4) . ?
C2 C18 1.383(5) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9500 . ?
C4 C16 1.400(5) . ?
C4 C5 1.500(5) . ?
C5 C6 1.507(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.484(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.321(4) . ?
C7 C8 1.398(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(5) . ?
C8 C13 1.430(5) . ?
C9 O3 1.370(4) . ?
C9 C10 1.382(5) . ?
C10 O4 1.369(4) . ?
C10 C11 1.409(5) . ?
C11 C12 1.356(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.410(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(5) . ?
C14 C15 1.378(5) . ?
C14 H14 0.9500 . ?
C15 N1 1.401(4) . ?
C15 C16 1.468(5) . ?
C16 C17 1.416(5) . ?
C17 C18 1.347(5) . ?
C17 H17 0.9500 . ?
C18 O2 1.377(4) . ?
C19 O3 1.430(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O4 1.440(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O5 H19 0.844(10) . ?
O5 H20 0.839(10) . ?
O6 H21 0.833(10) . ?
O6 H22 0.832(10) . ?

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
O2 C1 O1 107.4(3) . . ?
O2 C1 H1A 110.2 . . ?
O1 C1 H1A 110.2 . . ?
O2 C1 H1B 110.2 . . ?
O1 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C3 C2 O1 127.9(4) . . ?
C3 C2 C18 121.9(4) . . ?
O1 C2 C18 110.2(4) . . ?
C2 C3 C4 117.1(4) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C3 C4 C16 120.7(3) . . ?
C3 C4 C5 120.2(3) . . ?
C16 C4 C5 119.2(3) . . ?
C4 C5 C6 110.2(3) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C5 111.0(3) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C8 122.2(3) . . ?
N1 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 C13 118.0(3) . . ?
C9 C8 C13 120.7(3) . . ?
O3 C9 C10 121.6(3) . . ?
O3 C9 C8 118.7(3) . . ?
C10 C9 C8 119.5(3) . . ?
O4 C10 C9 116.2(3) . . ?
O4 C10 C11 124.4(4) . . ?
C9 C10 C11 119.4(4) . . ?
C12 C11 C10 122.1(4) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 124.5(3) . . ?
C14 C13 C8 117.5(3) . . ?
C12 C13 C8 118.0(3) . . ?
C15 C14 C13 123.0(3) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 C15 N1 117.0(3) . . ?
C14 C15 C16 125.0(3) . . ?
N1 C15 C16 118.0(3) . . ?
C4 C16 C17 120.8(4) . . ?
C4 C16 C15 120.2(3) . . ?
C17 C16 C15 118.9(3) . . ?
C18 C17 C16 116.6(4) . . ?
C18 C17 H17 121.7 . . ?
C16 C17 H17 121.7 . . ?
C17 C18 O2 127.0(4) . . ?
C17 C18 C2 122.9(4) . . ?
O2 C18 C2 110.1(4) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N1 C15 122.2(3) . . ?
C7 N1 C6 119.0(3) . . ?
C15 N1 C6 118.7(3) . . ?
C2 O1 C1 104.8(3) . . ?
C18 O2 C1 105.8(3) . . ?
C9 O3 C19 114.0(3) . . ?
C10 O4 C20 117.2(3) . . ?
H19 O5 H20 109(2) . . ?
H21 O6 H22 110(2) . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.078


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetontrile'
