# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_orgp353sf1
_database_code_depnum_ccdc_archive 'CCDC 1864391'
loop_
_audit_author_name
_audit_author_address
'George Whitehead'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2018-08-28 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;
_audit_creation_date             2018-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl3 Dy N2 O3'
_chemical_formula_sum            'C22 H24 Cl3 Dy N2 O3'
_chemical_formula_weight         633.28
_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'
Dy Dy -0.1892 4.4098 '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                   7.1829(6)
_cell_length_b                   9.3204(10)
_cell_length_c                   10.2330(13)
_cell_angle_alpha                110.136(10)
_cell_angle_beta                 106.175(9)
_cell_angle_gamma                92.705(8)
_cell_volume                     609.91(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      25.4160
_cell_measurement_theta_min      3.7000
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.663
_exptl_absorpt_coefficient_mu    3.417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             311
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.1178
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4347
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         3.503
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  76.00   1.00   22.43    --   11.22  77.00-180.00   87
  2  ω    -35.00  60.00   1.00   22.43    --  -11.85  57.00  60.00   95
  3  ω    -78.00  13.00   1.00   22.43    --  -11.85 -57.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0155165000
_diffrn_orient_matrix_UB_12      -0.0760986000
_diffrn_orient_matrix_UB_13      -0.0364578000
_diffrn_orient_matrix_UB_21      0.0078088000
_diffrn_orient_matrix_UB_22      -0.0165631000
_diffrn_orient_matrix_UB_23      0.0638060000
_diffrn_orient_matrix_UB_31      -0.1026789000
_diffrn_orient_matrix_UB_32      -0.0259733000
_diffrn_orient_matrix_UB_33      -0.0254526000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1774
_reflns_number_total             2475
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      0.992
_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)+(0.0266P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: Cl2(0.5) O2(0.5) H2A(0.5) H2B(0.5)
3.a Riding coordinates:
 O2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C9(H9), C10(H10), C11(H11)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C6(H6A,H6B,H6C)
;
_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
Dy1 Dy 0.500000 0.000000 0.000000 0.0460(2) Uani 1 2 d S T P . .
Cl1 Cl 0.4958(3) -0.0776(2) 0.22844(19) 0.0494(5) Uani 1 1 d . . . . .
Cl2 Cl 0.8568(11) -0.1352(7) 0.0191(9) 0.058(2) Uani 0.5 1 d . . . A -1
O1 O 0.6471(6) 0.2235(5) 0.1606(4) 0.0371(12) Uani 1 1 d . . . . .
N1 N 0.6580(7) 0.2736(7) 0.4382(5) 0.0346(14) Uani 1 1 d . . . . .
H1 H 0.623060 0.181400 0.367600 0.041 Uiso 1 1 calc R . . . .
C1 C 0.7040(8) 0.3681(8) 0.2586(6) 0.0266(15) Uani 1 1 d . . . . .
C7 C 0.7098(8) 0.3949(8) 0.4039(6) 0.0270(15) Uani 1 1 d . . . . .
C2 C 0.7595(9) 0.4914(8) 0.2285(7) 0.0308(16) Uani 1 1 d . . . . .
C4 C 0.8136(9) 0.6399(8) 0.3385(7) 0.0360(17) Uani 1 1 d . . . . .
H4 H 0.847833 0.723863 0.312703 0.043 Uiso 1 1 calc R . . . .
C3 C 0.7626(10) 0.4673(8) 0.0760(7) 0.0458(19) Uani 1 1 d . . . . .
H3A H 0.876786 0.419236 0.059771 0.069 Uiso 1 1 calc GR . . . .
H3B H 0.770798 0.567351 0.064580 0.069 Uiso 1 1 calc GR . . . .
H3C H 0.642214 0.399573 0.004311 0.069 Uiso 1 1 calc GR . . . .
C8 C 0.7667(8) 0.5424(8) 0.5162(7) 0.0300(16) Uani 1 1 d . . . . .
C5 C 0.8203(9) 0.6715(8) 0.4820(7) 0.0363(18) Uani 1 1 d . . . . .
C9 C 0.7657(9) 0.5553(9) 0.6560(7) 0.0408(19) Uani 1 1 d . . . . .
H9 H 0.805478 0.653670 0.733921 0.049 Uiso 1 1 calc R . . . .
C10 C 0.7090(10) 0.4299(10) 0.6829(8) 0.051(2) Uani 1 1 d . . . . .
H10 H 0.705140 0.441362 0.777990 0.062 Uiso 1 1 calc R . . . .
C11 C 0.6563(10) 0.2839(9) 0.5699(7) 0.0436(19) Uani 1 1 d . . . . .
H11 H 0.620144 0.194492 0.587421 0.052 Uiso 1 1 calc R . . . .
C6 C 0.8813(10) 0.8344(8) 0.5947(8) 0.053(2) Uani 1 1 d . . . . .
H6A H 1.000557 0.839223 0.672462 0.079 Uiso 1 1 calc GR . . . .
H6B H 0.775783 0.864355 0.637086 0.079 Uiso 1 1 calc GR . . . .
H6C H 0.907322 0.905441 0.547829 0.079 Uiso 1 1 calc GR . . . .
O2 O 0.194(2) 0.0694(15) -0.0017(17) 0.042(4) Uani 0.5 1 d . . . A -1
H2A H 0.148038 0.085647 -0.082574 0.063 Uiso 0.5 1 d R . . A -1
H2B H 0.094238 0.015457 0.001376 0.063 Uiso 0.5 1 d R . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 Cl1 2.6816(18) . ?
Dy1 Cl1 2.6816(18) 2_655 ?
Dy1 Cl2 2.897(6) . ?
Dy1 O1 2.150(4) 2_655 ?
Dy1 O1 2.150(4) . ?
Dy1 O2 2.318(14) 2_655 ?
Dy1 O2 2.318(14) . ?
Cl2 H2A 0.67(2) 2_655 ?
Cl2 H2B 1.257(19) 2_655 ?
O1 C1 1.333(7) . ?
N1 H1 0.8800 . ?
N1 C7 1.359(8) . ?
N1 C11 1.321(8) . ?
C1 C7 1.408(8) . ?
C1 C2 1.359(9) . ?
C7 C8 1.406(8) . ?
C2 C4 1.402(8) . ?
C2 C3 1.505(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(9) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C8 C5 1.428(9) . ?
C8 C9 1.396(9) . ?
C5 C6 1.510(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.359(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(10) . ?
C11 H11 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O2 H2A 0.8693 . ?
O2 H2B 0.8689 . ?

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
Cl1 Dy1 Cl1 180.00(7) 2_655 . ?
Cl1 Dy1 Cl2 84.29(17) . . ?
Cl1 Dy1 Cl2 95.71(17) 2_655 . ?
O1 Dy1 Cl1 86.03(12) 2_655 2_655 ?
O1 Dy1 Cl1 86.03(12) . . ?
O1 Dy1 Cl1 93.97(12) 2_655 . ?
O1 Dy1 Cl1 93.97(12) . 2_655 ?
O1 Dy1 Cl2 85.92(18) 2_655 . ?
O1 Dy1 Cl2 94.08(18) . . ?
O1 Dy1 O1 180.0(2) 2_655 . ?
O1 Dy1 O2 91.9(4) 2_655 2_655 ?
O1 Dy1 O2 91.9(4) . . ?
O1 Dy1 O2 88.1(4) . 2_655 ?
O1 Dy1 O2 88.1(4) 2_655 . ?
O2 Dy1 Cl1 86.4(4) 2_655 2_655 ?
O2 Dy1 Cl1 86.4(4) . . ?
O2 Dy1 Cl1 93.6(4) . 2_655 ?
O2 Dy1 Cl1 93.6(4) 2_655 . ?
O2 Dy1 Cl2 11.4(5) 2_655 . ?
O2 Dy1 Cl2 168.6(5) . . ?
O2 Dy1 O2 180.0 2_655 . ?
Dy1 Cl2 H2A 65.1(15) . 2_655 ?
Dy1 Cl2 H2B 79.0(7) . 2_655 ?
H2A Cl2 H2B 84.5 2_655 2_655 ?
C1 O1 Dy1 169.1(4) . . ?
C7 N1 H1 117.6 . . ?
C11 N1 H1 117.6 . . ?
C11 N1 C7 124.8(6) . . ?
O1 C1 C7 118.0(6) . . ?
O1 C1 C2 124.5(5) . . ?
C2 C1 C7 117.5(6) . . ?
N1 C7 C1 119.0(6) . . ?
N1 C7 C8 118.0(6) . . ?
C8 C7 C1 123.0(6) . . ?
C1 C2 C4 120.3(6) . . ?
C1 C2 C3 119.4(6) . . ?
C4 C2 C3 120.3(6) . . ?
C2 C4 H4 118.0 . . ?
C5 C4 C2 124.0(7) . . ?
C5 C4 H4 118.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C7 C8 C5 118.8(6) . . ?
C9 C8 C7 117.9(7) . . ?
C9 C8 C5 123.3(6) . . ?
C4 C5 C8 116.4(6) . . ?
C4 C5 C6 121.0(7) . . ?
C8 C5 C6 122.7(6) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(7) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.7(7) . . ?
C11 C10 H10 120.2 . . ?
N1 C11 C10 118.3(7) . . ?
N1 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Dy1 O2 H2A 105.5 . . ?
Dy1 O2 H2B 127.4 . . ?
H2A O2 H2B 103.5 . . ?

_olex2_date_sample_data_collection 2016-12-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.918
