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

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

data_17ma150b_mnb399
_database_code_depnum_ccdc_archive 'CCDC 1582052'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;

_audit_creation_date             2017-10-03T17:58:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H22 I N3 O4'
_chemical_formula_moiety         'C16 H19 N2 O4, C2 H3 N, I'
_chemical_formula_weight         471.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.76540(10)
_cell_length_b                   8.66930(10)
_cell_length_c                   23.9759(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.6120(10)
_cell_angle_gamma                90
_cell_volume                     1988.24(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    12621
_cell_measurement_theta_min      2.129
_cell_measurement_theta_max      27.833

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.099
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             944

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Spherical absorption correction
 using equivalent radius and absorption coefficient.
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.75905
_exptl_absorpt_correction_T_max  0.76671

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      123(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0116943412
_diffrn_orient_matrix_ub_12      -0.0191737857
_diffrn_orient_matrix_ub_13      0.0293386826
_diffrn_orient_matrix_ub_21      -0.0030067407
_diffrn_orient_matrix_ub_22      0.0792884553
_diffrn_orient_matrix_ub_23      0.0069482452
_diffrn_orient_matrix_ub_31      -0.073159381
_diffrn_orient_matrix_ub_32      -0.0063302369
_diffrn_orient_matrix_ub_33      -0.0017507823
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_number            20170
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.734
_diffrn_reflns_theta_max         28.224
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.93
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.93
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.93
_reflns_Friedel_coverage         0
_reflns_number_total             4565
_reflns_number_gt                4166
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²+0.8724P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4565
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_gt          0.0465
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.3
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.79059(17) 0.3226(2) 0.49887(7) 0.0174(3) Uani 1 1 d . . . . .
H1A H 0.841021 0.262726 0.476599 0.021 Uiso 1 1 calc R U . . .
C2 C 0.77773(16) 0.4811(2) 0.49087(7) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.70251(17) 0.5700(2) 0.52291(7) 0.0163(3) Uani 1 1 d . . . . .
H3 H 0.695175 0.678468 0.517395 0.02 Uiso 1 1 calc R U . . .
C4 C 0.63855(16) 0.4990(2) 0.56284(7) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.65146(17) 0.3399(2) 0.57172(7) 0.0174(4) Uani 1 1 d . . . . .
C6 C 0.72884(17) 0.2523(2) 0.53984(7) 0.0171(4) Uani 1 1 d . . . . .
C7 C 0.5598(2) 0.7400(2) 0.59251(9) 0.0256(4) Uani 1 1 d . . . . .
H7A H 0.519041 0.770117 0.553289 0.038 Uiso 1 1 calc R U . . .
H7B H 0.654813 0.78139 0.603208 0.038 Uiso 1 1 calc R U . . .
H7C H 0.50238 0.781132 0.61822 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4810(2) 0.1762(3) 0.59968(9) 0.0322(5) Uani 1 1 d . . . . .
H8A H 0.498507 0.101016 0.571396 0.048 Uiso 1 1 calc R U . . .
H8B H 0.399376 0.239025 0.58329 0.048 Uiso 1 1 calc R U . . .
H8C H 0.46323 0.121703 0.63332 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8355(2) 0.0106(2) 0.52721(9) 0.0265(4) Uani 1 1 d . . . . .
H9A H 0.800454 0.005995 0.485962 0.04 Uiso 1 1 calc R U . . .
H9B H 0.842804 -0.094187 0.54289 0.04 Uiso 1 1 calc R U . . .
H9C H 0.927935 0.059379 0.53509 0.04 Uiso 1 1 calc R U . . .
C10 C 0.84986(17) 0.5673(2) 0.45078(7) 0.0169(4) Uani 1 1 d . . . . .
C11 C 0.97908(17) 0.5294(2) 0.37302(7) 0.0178(4) Uani 1 1 d . . . . .
C12 C 0.99524(17) 0.6829(2) 0.35973(7) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.94657 0.761202 0.37551 0.023 Uiso 1 1 calc R U . . .
C13 C 1.14993(18) 0.6127(2) 0.29989(8) 0.0236(4) Uani 1 1 d . . . . .
H13 H 1.208758 0.643243 0.274763 0.028 Uiso 1 1 calc R U . . .
C14 C 1.13548(18) 0.4599(2) 0.31139(8) 0.0239(4) Uani 1 1 d . . . . .
H14 H 1.183094 0.383857 0.293988 0.029 Uiso 1 1 calc R U . . .
C15 C 1.05082(18) 0.4168(2) 0.34862(8) 0.0213(4) Uani 1 1 d . . . . .
H15 H 1.041551 0.311014 0.357544 0.026 Uiso 1 1 calc R U . . .
C16 C 1.1058(2) 0.8847(2) 0.31301(9) 0.0266(4) Uani 1 1 d . . . . .
H16A H 1.025505 0.945903 0.318905 0.04 Uiso 1 1 calc R U . . .
H16B H 1.117759 0.89716 0.273649 0.04 Uiso 1 1 calc R U . . .
H16C H 1.190287 0.920031 0.339173 0.04 Uiso 1 1 calc R U . . .
C17 C 0.3586(2) 0.4187(2) 0.73619(9) 0.0309(5) Uani 1 1 d . . . . .
C18 C 0.4629(2) 0.5133(3) 0.71663(10) 0.0380(5) Uani 1 1 d . . . . .
H18A H 0.492072 0.46246 0.684416 0.057 Uiso 1 1 calc R U . . .
H18B H 0.544183 0.526628 0.747719 0.057 Uiso 1 1 calc R U . . .
H18C H 0.422701 0.61442 0.704616 0.057 Uiso 1 1 calc R U . . .
I1 I 0.78055(2) 0.10651(2) 0.35035(2) 0.02076(5) Uani 1 1 d . . . . .
N1 N 0.89231(15) 0.48008(19) 0.40967(6) 0.0189(3) Uani 1 1 d . . . . .
H1 H 0.868(2) 0.388(2) 0.4058(9) 0.023 Uiso 1 1 d . U . . .
N2 N 1.08115(14) 0.71992(19) 0.32403(6) 0.0198(3) Uani 1 1 d . . . . .
N3 N 0.2762(2) 0.3478(2) 0.75183(10) 0.0483(5) Uani 1 1 d . . . . .
O1 O 0.56426(13) 0.57527(15) 0.59664(6) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.60121(12) 0.27430(15) 0.61585(5) 0.0219(3) Uani 1 1 d . . . . .
O3 O 0.74076(14) 0.09934(14) 0.55314(6) 0.0226(3) Uani 1 1 d . . . . .
O4 O 0.87187(13) 0.70554(15) 0.45550(5) 0.0220(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.390(3) . ?
C1 C6 1.392(2) . ?
C1 H1A 0.95 . ?
C2 C3 1.397(2) . ?
C2 C10 1.500(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.95 . ?
C4 O1 1.3626(19) . ?
C4 C5 1.397(3) . ?
C5 O2 1.376(2) . ?
C5 C6 1.402(2) . ?
C6 O3 1.364(2) . ?
C7 O1 1.431(2) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 O2 1.438(2) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 O3 1.438(2) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 O4 1.219(2) . ?
C10 N1 1.371(2) . ?
C11 C12 1.384(3) . ?
C11 C15 1.397(2) . ?
C11 N1 1.405(2) . ?
C12 N2 1.352(2) . ?
C12 H12 0.95 . ?
C13 N2 1.344(2) . ?
C13 C14 1.366(3) . ?
C13 H13 0.95 . ?
C14 C15 1.385(2) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N2 1.481(2) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 N3 1.135(3) . ?
C17 C18 1.457(3) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
N1 H1 0.83(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.33(16) . . ?
C2 C1 H1A 120.3 . . ?
C6 C1 H1A 120.3 . . ?
C1 C2 C3 120.86(15) . . ?
C1 C2 C10 122.68(15) . . ?
C3 C2 C10 116.36(16) . . ?
C4 C3 C2 119.60(16) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O1 C4 C3 124.22(16) . . ?
O1 C4 C5 115.52(15) . . ?
C3 C4 C5 120.23(15) . . ?
O2 C5 C4 119.34(15) . . ?
O2 C5 C6 120.69(16) . . ?
C4 C5 C6 119.58(15) . . ?
O3 C6 C1 124.18(16) . . ?
O3 C6 C5 115.43(15) . . ?
C1 C6 C5 120.37(17) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 N1 122.40(16) . . ?
O4 C10 C2 121.80(15) . . ?
N1 C10 C2 115.77(15) . . ?
C12 C11 C15 119.04(16) . . ?
C12 C11 N1 123.20(16) . . ?
C15 C11 N1 117.75(16) . . ?
N2 C12 C11 119.20(16) . . ?
N2 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N2 C13 C14 120.20(16) . . ?
N2 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.40(18) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C11 119.75(18) . . ?
C14 C15 H15 120.1 . . ?
C11 C15 H15 120.1 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 178.5(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 N1 C11 126.14(16) . . ?
C10 N1 H1 119.2(15) . . ?
C11 N1 H1 114.6(15) . . ?
C13 N2 C12 122.39(17) . . ?
C13 N2 C16 118.50(15) . . ?
C12 N2 C16 119.05(16) . . ?
C4 O1 C7 117.10(14) . . ?
C5 O2 C8 115.80(14) . . ?
C6 O3 C9 116.84(14) . . ?

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
C6 C1 C2 C3 -0.7(2) . . . . ?
C6 C1 C2 C10 175.33(16) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C10 C2 C3 C4 -176.96(15) . . . . ?
C2 C3 C4 O1 179.24(15) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
O1 C4 C5 O2 -5.7(2) . . . . ?
C3 C4 C5 O2 172.56(15) . . . . ?
O1 C4 C5 C6 -178.53(15) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C2 C1 C6 O3 -176.60(16) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
O2 C5 C6 O3 4.5(2) . . . . ?
C4 C5 C6 O3 177.26(15) . . . . ?
O2 C5 C6 C1 -173.88(15) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
C1 C2 C10 O4 -158.51(17) . . . . ?
C3 C2 C10 O4 17.7(2) . . . . ?
C1 C2 C10 N1 19.9(2) . . . . ?
C3 C2 C10 N1 -163.91(15) . . . . ?
C15 C11 C12 N2 -0.7(2) . . . . ?
N1 C11 C12 N2 179.96(16) . . . . ?
N2 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C11 1.3(3) . . . . ?
C12 C11 C15 C14 -0.6(3) . . . . ?
N1 C11 C15 C14 178.79(16) . . . . ?
O4 C10 N1 C11 8.4(3) . . . . ?
C2 C10 N1 C11 -169.99(15) . . . . ?
C12 C11 N1 C10 -22.9(3) . . . . ?
C15 C11 N1 C10 157.78(17) . . . . ?
C14 C13 N2 C12 -0.5(3) . . . . ?
C14 C13 N2 C16 176.63(17) . . . . ?
C11 C12 N2 C13 1.3(2) . . . . ?
C11 C12 N2 C16 -175.85(16) . . . . ?
C3 C4 O1 C7 -3.8(2) . . . . ?
C5 C4 O1 C7 174.34(15) . . . . ?
C4 C5 O2 C8 111.34(19) . . . . ?
C6 C5 O2 C8 -75.9(2) . . . . ?
C1 C6 O3 C9 6.9(2) . . . . ?
C5 C6 O3 C9 -171.34(15) . . . . ?

####################################################################### 
# 
# 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_17ma149_mnb401
_database_code_depnum_ccdc_archive 'CCDC 1582054'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;

_audit_creation_date             2017-10-03T11:40:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C26 H32 Cl Ir N2 O4'
_chemical_formula_moiety         'C26 H32 Cl Ir N2 O4'
_chemical_formula_weight         664.18

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_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'
'-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                   15.5088(3)
_cell_length_b                   13.34471(14)
_cell_length_c                   24.9142(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5156.26(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8685
_cell_measurement_theta_min      2.088
_cell_measurement_theta_max      27.558

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             2624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0128
0 0 1 0.0128
1 0 0 0.0224
-1 0 0 0.0214
0 -1 0 0.1526
0 1 0 0.1526


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.316
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.482
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      123(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0246358
_diffrn_orient_matrix_ub_12      -0.0027372
_diffrn_orient_matrix_ub_13      -0.0239424
_diffrn_orient_matrix_ub_21      0.0385219
_diffrn_orient_matrix_ub_22      -0.0031418
_diffrn_orient_matrix_ub_23      -0.0152597
_diffrn_orient_matrix_ub_31      -0.0010146
_diffrn_orient_matrix_ub_32      -0.052979
_diffrn_orient_matrix_ub_33      0.0021474
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.061
_diffrn_reflns_number            28230
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.635
_diffrn_reflns_theta_max         28.107
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.917
_reflns_Friedel_coverage         0
_reflns_number_total             5778
_reflns_number_gt                3977
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²+3.3933P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5778
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0508
_refine_ls_wR_factor_gt          0.0441
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.83
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.127

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Ir Ir -1.4442 7.9887 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Ir1 Ir 0.55775(2) 0.18041(2) 0.37445(2) 0.01924(5) Uani 1 1 d . . . . .
Cl1 Cl 0.47447(6) 0.11669(8) 0.44886(4) 0.0290(3) Uani 1 1 d . . . . .
O4 O 0.64940(17) 0.42326(19) 0.46480(10) 0.0271(7) Uani 1 1 d . . . . .
O2 O 0.30058(16) 0.45659(19) 0.33065(10) 0.0234(7) Uani 1 1 d . . . . .
O3 O 0.36491(17) 0.26771(19) 0.32389(10) 0.0235(7) Uani 1 1 d . . . . .
O1 O 0.38898(16) 0.60691(18) 0.37691(10) 0.0245(6) Uani 1 1 d . . . . .
N1 N 0.6275(2) 0.2641(2) 0.43064(12) 0.0190(8) Uani 1 1 d . . . . .
N2 N 0.7463(2) 0.0914(2) 0.51602(12) 0.0188(8) Uani 1 1 d . . . . .
C1 C 0.4917(2) 0.3135(3) 0.37633(15) 0.0185(8) Uani 1 1 d . . . . .
C5 C 0.3807(3) 0.4363(3) 0.35274(15) 0.0203(9) Uani 1 1 d . . . . .
C2 C 0.5318(2) 0.3912(3) 0.40382(15) 0.0185(9) Uani 1 1 d . . . . .
C4 C 0.4258(2) 0.5133(3) 0.37902(15) 0.0206(9) Uani 1 1 d . . . . .
C10 C 0.6093(2) 0.3635(3) 0.43542(16) 0.0204(9) Uani 1 1 d . . . . .
C12 C 0.6815(3) 0.1360(3) 0.48897(15) 0.0200(9) Uani 1 1 d . . . . .
H12 H 0.625451 0.107331 0.489791 0.024 Uiso 1 1 calc R U . . .
C19 C 0.5672(3) 0.1715(3) 0.28862(15) 0.0247(10) Uani 1 1 d . . . . .
C13 C 0.8273(3) 0.1288(3) 0.51546(15) 0.0215(9) Uani 1 1 d . . . . .
H13 H 0.872377 0.094903 0.533786 0.026 Uiso 1 1 calc R U . . .
C11 C 0.6957(3) 0.2234(3) 0.45991(15) 0.0181(9) Uani 1 1 d . . . . .
C21 C 0.6607(3) 0.0789(3) 0.34253(16) 0.0265(10) Uani 1 1 d . . . . .
C17 C 0.5819(3) 0.0285(3) 0.34033(16) 0.0277(11) Uani 1 1 d . . . . .
C14 C 0.8438(3) 0.2160(3) 0.48822(15) 0.0236(10) Uani 1 1 d . . . . .
H14 H 0.900395 0.243105 0.488024 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3053(3) 0.4809(3) 0.27507(15) 0.0314(11) Uani 1 1 d . . . . .
H8A H 0.331689 0.425053 0.255467 0.047 Uiso 1 1 calc R U . . .
H8B H 0.340415 0.541284 0.27032 0.047 Uiso 1 1 calc R U . . .
H8C H 0.247128 0.492948 0.261178 0.047 Uiso 1 1 calc R U . . .
C18 C 0.5223(3) 0.0854(3) 0.30730(16) 0.0254(10) Uani 1 1 d . . . . .
C15 C 0.7785(3) 0.2642(3) 0.46117(15) 0.0230(10) Uani 1 1 d . . . . .
H15 H 0.78986 0.325658 0.443254 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5015(3) 0.4897(3) 0.40584(15) 0.0211(10) Uani 1 1 d . . . . .
H3 H 0.532114 0.539582 0.425235 0.025 Uiso 1 1 calc R U . . .
C6 C 0.4129(3) 0.3388(3) 0.35148(15) 0.0201(9) Uani 1 1 d . . . . .
C20 C 0.6520(3) 0.1719(3) 0.31230(16) 0.0264(10) Uani 1 1 d . . . . .
C16 C 0.7272(3) 0.0010(3) 0.54793(15) 0.0245(10) Uani 1 1 d . . . . .
H16A H 0.729999 0.017468 0.586231 0.037 Uiso 1 1 calc R U . . .
H16B H 0.769624 -0.051163 0.539689 0.037 Uiso 1 1 calc R U . . .
H16C H 0.66928 -0.023223 0.539089 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3006(3) 0.2220(3) 0.35741(16) 0.0330(11) Uani 1 1 d . . . . .
H9A H 0.267509 0.173373 0.336318 0.049 Uiso 1 1 calc R U . . .
H9B H 0.261756 0.273691 0.371331 0.049 Uiso 1 1 calc R U . . .
H9C H 0.328787 0.187615 0.387433 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4290(3) 0.6828(3) 0.40861(17) 0.0324(11) Uani 1 1 d . . . . .
H7A H 0.488503 0.692607 0.396427 0.049 Uiso 1 1 calc R U . . .
H7B H 0.429117 0.662193 0.446367 0.049 Uiso 1 1 calc R U . . .
H7C H 0.396944 0.745652 0.404815 0.049 Uiso 1 1 calc R U . . .
C26 C 0.7429(3) 0.0435(3) 0.36881(17) 0.0409(12) Uani 1 1 d . . . . .
H26A H 0.778683 0.101497 0.378052 0.061 Uiso 1 1 calc R U . . .
H26B H 0.774434 -0.000018 0.343958 0.061 Uiso 1 1 calc R U . . .
H26C H 0.728868 0.006031 0.401499 0.061 Uiso 1 1 calc R U . . .
C22 C 0.5607(3) -0.0696(3) 0.36710(18) 0.0434(13) Uani 1 1 d . . . . .
H22A H 0.591822 -0.074402 0.401232 0.065 Uiso 1 1 calc R U . . .
H22B H 0.577946 -0.125084 0.343661 0.065 Uiso 1 1 calc R U . . .
H22C H 0.498504 -0.073253 0.373824 0.065 Uiso 1 1 calc R U . . .
C24 C 0.5343(3) 0.2463(3) 0.24831(17) 0.0375(13) Uani 1 1 d . . . . .
H24A H 0.471324 0.249879 0.250506 0.056 Uiso 1 1 calc R U . . .
H24B H 0.551314 0.22528 0.212126 0.056 Uiso 1 1 calc R U . . .
H24C H 0.558954 0.312357 0.256035 0.056 Uiso 1 1 calc R U . . .
C25 C 0.7218(3) 0.2457(3) 0.30122(18) 0.0412(13) Uani 1 1 d . . . . .
H25A H 0.696237 0.311099 0.293082 0.062 Uiso 1 1 calc R U . . .
H25B H 0.755964 0.222894 0.270464 0.062 Uiso 1 1 calc R U . . .
H25C H 0.75909 0.251555 0.332806 0.062 Uiso 1 1 calc R U . . .
C23 C 0.4361(3) 0.0485(3) 0.28871(18) 0.0429(13) Uani 1 1 d . . . . .
H23A H 0.407048 0.013727 0.31826 0.064 Uiso 1 1 calc R U . . .
H23B H 0.443915 0.002195 0.258585 0.064 Uiso 1 1 calc R U . . .
H23C H 0.400883 0.105551 0.277124 0.064 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Ir1 C1 2.050(4) . ?
Ir1 N1 2.093(3) . ?
Ir1 C20 2.132(4) . ?
Ir1 C19 2.147(4) . ?
Ir1 C18 2.170(4) . ?
Ir1 C17 2.230(4) . ?
Ir1 C21 2.240(4) . ?
Ir1 Cl1 2.4141(10) . ?
O4 C10 1.249(4) . ?
O2 C5 1.385(4) . ?
O2 C8 1.424(4) . ?
O3 C6 1.388(4) . ?
O3 C9 1.436(4) . ?
O1 C4 1.374(4) . ?
O1 C7 1.426(4) . ?
N1 C10 1.361(4) . ?
N1 C11 1.394(4) . ?
N2 C12 1.349(4) . ?
N2 C13 1.351(4) . ?
N2 C16 1.474(4) . ?
C1 C2 1.390(5) . ?
C1 C6 1.411(5) . ?
C5 C6 1.395(5) . ?
C5 C4 1.405(5) . ?
C2 C3 1.397(5) . ?
C2 C10 1.483(5) . ?
C4 C3 1.387(5) . ?
C12 C11 1.390(5) . ?
C12 H12 0.95 . ?
C19 C18 1.423(5) . ?
C19 C20 1.440(5) . ?
C19 C24 1.505(5) . ?
C13 C14 1.371(5) . ?
C13 H13 0.95 . ?
C11 C15 1.395(5) . ?
C21 C17 1.396(5) . ?
C21 C20 1.458(5) . ?
C21 C26 1.509(5) . ?
C17 C18 1.451(5) . ?
C17 C22 1.506(5) . ?
C14 C15 1.376(5) . ?
C14 H14 0.95 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C18 C23 1.498(5) . ?
C15 H15 0.95 . ?
C3 H3 0.95 . ?
C20 C25 1.489(5) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?

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
C1 Ir1 N1 77.34(14) . . ?
C1 Ir1 C20 113.89(15) . . ?
N1 Ir1 C20 99.20(14) . . ?
C1 Ir1 C19 96.02(14) . . ?
N1 Ir1 C19 131.34(14) . . ?
C20 Ir1 C19 39.35(14) . . ?
C1 Ir1 C18 113.40(15) . . ?
N1 Ir1 C18 163.49(14) . . ?
C20 Ir1 C18 65.34(15) . . ?
C19 Ir1 C18 38.48(14) . . ?
C1 Ir1 C17 151.63(15) . . ?
N1 Ir1 C17 130.80(14) . . ?
C20 Ir1 C17 63.88(15) . . ?
C19 Ir1 C17 63.81(15) . . ?
C18 Ir1 C17 38.50(14) . . ?
C1 Ir1 C21 152.61(15) . . ?
N1 Ir1 C21 101.05(14) . . ?
C20 Ir1 C21 38.86(14) . . ?
C19 Ir1 C21 64.15(14) . . ?
C18 Ir1 C21 63.48(15) . . ?
C17 Ir1 C21 36.41(14) . . ?
C1 Ir1 Cl1 91.16(10) . . ?
N1 Ir1 Cl1 87.18(9) . . ?
C20 Ir1 Cl1 154.91(11) . . ?
C19 Ir1 Cl1 141.46(11) . . ?
C18 Ir1 Cl1 104.51(12) . . ?
C17 Ir1 Cl1 93.57(11) . . ?
C21 Ir1 Cl1 116.17(11) . . ?
C5 O2 C8 112.6(3) . . ?
C6 O3 C9 112.0(3) . . ?
C4 O1 C7 116.3(3) . . ?
C10 N1 C11 119.4(3) . . ?
C10 N1 Ir1 118.1(3) . . ?
C11 N1 Ir1 122.3(2) . . ?
C12 N2 C13 121.6(3) . . ?
C12 N2 C16 118.7(3) . . ?
C13 N2 C16 119.6(3) . . ?
C2 C1 C6 115.1(3) . . ?
C2 C1 Ir1 115.7(3) . . ?
C6 C1 Ir1 129.0(3) . . ?
O2 C5 C6 119.6(4) . . ?
O2 C5 C4 119.3(3) . . ?
C6 C5 C4 121.0(4) . . ?
C1 C2 C3 124.7(4) . . ?
C1 C2 C10 115.9(3) . . ?
C3 C2 C10 119.2(4) . . ?
O1 C4 C3 125.2(3) . . ?
O1 C4 C5 116.1(3) . . ?
C3 C4 C5 118.7(3) . . ?
O4 C10 N1 124.8(4) . . ?
O4 C10 C2 123.7(4) . . ?
N1 C10 C2 111.4(3) . . ?
N2 C12 C11 120.8(4) . . ?
N2 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C18 C19 C20 108.4(4) . . ?
C18 C19 C24 126.0(4) . . ?
C20 C19 C24 125.5(4) . . ?
C18 C19 Ir1 71.6(2) . . ?
C20 C19 Ir1 69.8(2) . . ?
C24 C19 Ir1 127.2(3) . . ?
N2 C13 C14 119.5(4) . . ?
N2 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C12 C11 N1 118.6(4) . . ?
C12 C11 C15 117.5(4) . . ?
N1 C11 C15 123.9(4) . . ?
C17 C21 C20 108.0(4) . . ?
C17 C21 C26 127.3(4) . . ?
C20 C21 C26 124.7(4) . . ?
C17 C21 Ir1 71.4(2) . . ?
C20 C21 Ir1 66.6(2) . . ?
C26 C21 Ir1 129.6(3) . . ?
C21 C17 C18 109.1(4) . . ?
C21 C17 C22 126.3(4) . . ?
C18 C17 C22 124.5(4) . . ?
C21 C17 Ir1 72.2(2) . . ?
C18 C17 Ir1 68.5(2) . . ?
C22 C17 Ir1 125.8(3) . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C19 C18 C17 107.2(4) . . ?
C19 C18 C23 127.0(4) . . ?
C17 C18 C23 124.9(4) . . ?
C19 C18 Ir1 69.9(2) . . ?
C17 C18 Ir1 73.0(2) . . ?
C23 C18 Ir1 131.0(3) . . ?
C14 C15 C11 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C11 C15 H15 119.8 . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
O3 C6 C5 117.2(4) . . ?
O3 C6 C1 121.2(3) . . ?
C5 C6 C1 121.6(4) . . ?
C19 C20 C21 107.1(4) . . ?
C19 C20 C25 126.1(4) . . ?
C21 C20 C25 126.2(4) . . ?
C19 C20 Ir1 70.9(2) . . ?
C21 C20 Ir1 74.6(2) . . ?
C25 C20 Ir1 126.7(3) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C8 O2 C5 C6 -88.7(4) . . . . ?
C8 O2 C5 C4 95.2(4) . . . . ?
C6 C1 C2 C3 -3.0(6) . . . . ?
Ir1 C1 C2 C3 174.1(3) . . . . ?
C6 C1 C2 C10 173.2(3) . . . . ?
Ir1 C1 C2 C10 -9.6(4) . . . . ?
C7 O1 C4 C3 -5.3(5) . . . . ?
C7 O1 C4 C5 173.0(3) . . . . ?
O2 C5 C4 O1 -5.2(5) . . . . ?
C6 C5 C4 O1 178.8(3) . . . . ?
O2 C5 C4 C3 173.3(3) . . . . ?
C6 C5 C4 C3 -2.8(6) . . . . ?
C11 N1 C10 O4 -0.2(6) . . . . ?
Ir1 N1 C10 O4 -175.3(3) . . . . ?
C11 N1 C10 C2 -176.6(3) . . . . ?
Ir1 N1 C10 C2 8.3(4) . . . . ?
C1 C2 C10 O4 -175.6(4) . . . . ?
C3 C2 C10 O4 0.9(6) . . . . ?
C1 C2 C10 N1 0.9(5) . . . . ?
C3 C2 C10 N1 177.3(3) . . . . ?
C13 N2 C12 C11 -0.8(5) . . . . ?
C16 N2 C12 C11 177.7(3) . . . . ?
C12 N2 C13 C14 2.2(5) . . . . ?
C16 N2 C13 C14 -176.3(3) . . . . ?
N2 C12 C11 N1 177.1(3) . . . . ?
N2 C12 C11 C15 -1.8(5) . . . . ?
C10 N1 C11 C12 131.2(4) . . . . ?
Ir1 N1 C11 C12 -53.9(4) . . . . ?
C10 N1 C11 C15 -50.0(5) . . . . ?
Ir1 N1 C11 C15 124.9(3) . . . . ?
C20 C21 C17 C18 2.2(4) . . . . ?
C26 C21 C17 C18 -175.1(4) . . . . ?
Ir1 C21 C17 C18 58.8(3) . . . . ?
C20 C21 C17 C22 -178.4(4) . . . . ?
C26 C21 C17 C22 4.3(7) . . . . ?
Ir1 C21 C17 C22 -121.8(4) . . . . ?
C20 C21 C17 Ir1 -56.6(3) . . . . ?
C26 C21 C17 Ir1 126.1(4) . . . . ?
N2 C13 C14 C15 -0.8(6) . . . . ?
C20 C19 C18 C17 -3.5(4) . . . . ?
C24 C19 C18 C17 173.0(4) . . . . ?
Ir1 C19 C18 C17 -63.9(3) . . . . ?
C20 C19 C18 C23 -172.8(4) . . . . ?
C24 C19 C18 C23 3.7(6) . . . . ?
Ir1 C19 C18 C23 126.8(4) . . . . ?
C20 C19 C18 Ir1 60.4(3) . . . . ?
C24 C19 C18 Ir1 -123.2(4) . . . . ?
C21 C17 C18 C19 0.8(4) . . . . ?
C22 C17 C18 C19 -178.6(4) . . . . ?
Ir1 C17 C18 C19 61.9(3) . . . . ?
C21 C17 C18 C23 170.4(4) . . . . ?
C22 C17 C18 C23 -9.0(6) . . . . ?
Ir1 C17 C18 C23 -128.6(4) . . . . ?
C21 C17 C18 Ir1 -61.0(3) . . . . ?
C22 C17 C18 Ir1 119.5(4) . . . . ?
C13 C14 C15 C11 -1.9(6) . . . . ?
C12 C11 C15 C14 3.1(5) . . . . ?
N1 C11 C15 C14 -175.7(4) . . . . ?
O1 C4 C3 C2 -179.1(3) . . . . ?
C5 C4 C3 C2 2.6(5) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C10 C2 C3 C4 -175.8(3) . . . . ?
C9 O3 C6 C5 -87.5(4) . . . . ?
C9 O3 C6 C1 93.6(4) . . . . ?
O2 C5 C6 O3 5.0(5) . . . . ?
C4 C5 C6 O3 -179.0(3) . . . . ?
O2 C5 C6 C1 -176.1(3) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C2 C1 C6 O3 -178.3(3) . . . . ?
Ir1 C1 C6 O3 5.0(5) . . . . ?
C2 C1 C6 C5 2.9(5) . . . . ?
Ir1 C1 C6 C5 -173.9(3) . . . . ?
C18 C19 C20 C21 4.8(4) . . . . ?
C24 C19 C20 C21 -171.7(4) . . . . ?
Ir1 C19 C20 C21 66.4(3) . . . . ?
C18 C19 C20 C25 176.4(4) . . . . ?
C24 C19 C20 C25 -0.1(6) . . . . ?
Ir1 C19 C20 C25 -122.0(4) . . . . ?
C18 C19 C20 Ir1 -61.6(3) . . . . ?
C24 C19 C20 Ir1 122.0(4) . . . . ?
C17 C21 C20 C19 -4.3(4) . . . . ?
C26 C21 C20 C19 173.1(3) . . . . ?
Ir1 C21 C20 C19 -63.9(3) . . . . ?
C17 C21 C20 C25 -175.9(4) . . . . ?
C26 C21 C20 C25 1.5(6) . . . . ?
Ir1 C21 C20 C25 124.5(4) . . . . ?
C17 C21 C20 Ir1 59.6(3) . . . . ?
C26 C21 C20 Ir1 -123.0(4) . . . . ?
####################################################################### 
# 
# 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_17ma118
_database_code_depnum_ccdc_archive 'CCDC 1582053'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;
_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C16 H18 N2 O4), 4(H2 O), 2(C H2 Cl2)'
_chemical_formula_sum            'C66 H84 Cl4 N8 O20'
_chemical_formula_weight         1451.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H18N2O4
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/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                   11.6020(2)
_cell_length_b                   13.05540(10)
_cell_length_c                   12.1795(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.969(2)
_cell_angle_gamma                90
_cell_volume                     1754.83(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    11721
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      27.4530
_cell_measurement_theta_min      2.1020
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25283
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.120
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 122.00   1.00    5.58    --   27.42 178.00  30.00   87
  2  ω    -10.00 103.00   1.00    5.58    --   27.42  57.00 -60.00  113
  3  ω     35.00 122.00   1.00    5.58    --   27.42 178.00-150.00   87
  4  ω     35.00 122.00   1.00    5.58    --   27.42 178.00 120.00   87
  5  ω    -57.00 114.00   1.00    5.58    --   27.42  19.00  60.00  171
  6  ω    -49.00  65.00   1.00    5.58    --   27.42 -57.00 150.00  114
  7  ω    -20.00  32.00   1.00    5.58    --  -23.50 -99.00 -30.00   52
  8  ω    -10.00 103.00   1.00    5.58    --   27.42  57.00-120.00  113
  9  ω    -16.00 112.00   1.00    5.58    --   27.42  77.00  60.00  128
 10  ω    -49.00   4.00   1.00    5.58    --   27.42 -57.00   0.00   53
 11  ω    -10.00 103.00   1.00    5.58    --   27.42  57.00 150.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0366823000
_diffrn_orient_matrix_UB_12      -0.0226181000
_diffrn_orient_matrix_UB_13      -0.0519999000
_diffrn_orient_matrix_UB_21      0.0031560000
_diffrn_orient_matrix_UB_22      -0.0477012000
_diffrn_orient_matrix_UB_23      0.0286713000
_diffrn_orient_matrix_UB_31      -0.0526886000
_diffrn_orient_matrix_UB_32      0.0128739000
_diffrn_orient_matrix_UB_33      0.0148626000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2668
_reflns_number_total             3089
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.058
_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)+(0.0441P)²+0.4867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0910
_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. Others
 Fixed Sof: O1WB(0.5) H1WA(0.5) H1WB(0.5) Cl2(0.25) Cl3(0.25) C2(0.25)
 H2A(0.25) H2B(0.25) Cl1(0.25) Cl4(0.25) C8(0.25) H8A(0.25) H8B(0.25) O1WA(0.5)
 H1WC(0.5) H1WD(0.5)
 Fixed Uiso: H1WA(0.064) H1WB(0.064) H2A(0.11) H2B(0.11) H8A(0.067) H8B(0.067)
 H1WC(0.077) H1WD(0.077)
 Fixed X: H1WA(0.63389) H1WB(0.5505) H2A(1.10051) H2B(0.96952) H8A(1.06616)
 H8B(1.131781) H1WC(1.04781) H1WD(1.14809)
 Fixed Y: H1WA(0.20032) H1WB(0.17098) H2A(0.527841) H2B(0.54692) H8A(0.444468)
 H8B(0.482759) H1WC(0.33352) H1WD(0.29891)
 Fixed Z: H1WA(0.30364) H1WB(0.20511) H2A(1.09989) H2B(1.10692) H8A(0.930459)
 H8B(1.05706) H1WC(0.72341) H1WD(0.80335)
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C22(H22), C3(H3), C5(H5), C4(H4)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C15(H15A,H15B,H15C), C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;
_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
O14 O 0.94598(9) 0.04077(7) 0.84295(8) 0.0328(2) Uani 1 1 d . . . . .
O17 O 0.90205(8) -0.11861(7) 0.69461(8) 0.0309(2) Uani 1 1 d . . . . .
O20 O 0.83004(9) -0.08898(7) 0.46654(8) 0.0325(2) Uani 1 1 d . . . . .
O10 O 0.76110(9) 0.29838(7) 0.41518(8) 0.0376(3) Uani 1 1 d . . . . .
N8 N 0.88833(10) 0.35884(8) 0.59027(9) 0.0277(3) Uani 1 1 d . . . . .
N2 N 0.77257(10) 0.60785(8) 0.45640(10) 0.0286(3) Uani 1 1 d . . . . .
O1WB O 0.6240(8) 0.1623(6) 0.2447(6) 0.0428(13) Uani 0.5 1 d . . P A 2
H1WA H 0.6339 0.2003 0.3036 0.064 Uiso 0.5 1 d . . P B 2
H1WB H 0.5505 0.1710 0.2051 0.064 Uiso 0.5 1 d . . P C 2
C19 C 0.84895(11) -0.00290(10) 0.53374(11) 0.0256(3) Uani 1 1 d . . . . .
C16 C 0.88418(11) -0.01981(9) 0.65257(11) 0.0245(3) Uani 1 1 d . . . . .
C13 C 0.90622(11) 0.06425(10) 0.72749(11) 0.0253(3) Uani 1 1 d . . . . .
C12 C 0.88972(11) 0.16314(10) 0.68413(11) 0.0250(3) Uani 1 1 d . . . . .
H12 H 0.9034 0.2187 0.7343 0.030 Uiso 1 1 calc R . . . .
C6 C 0.87239(12) 0.46145(10) 0.56222(11) 0.0268(3) Uani 1 1 d . . . . .
C11 C 0.85260(11) 0.17922(10) 0.56539(11) 0.0249(3) Uani 1 1 d . . . . .
C9 C 0.82954(12) 0.28653(10) 0.51672(11) 0.0264(3) Uani 1 1 d . . . . .
C7 C 0.78030(12) 0.50510(10) 0.47204(12) 0.0273(3) Uani 1 1 d . . . . .
H7 H 0.7233 0.4629 0.4219 0.033 Uiso 1 1 calc R . . . .
C22 C 0.83365(12) 0.09647(10) 0.49034(12) 0.0274(3) Uani 1 1 d . . . . .
H22 H 0.8107 0.1074 0.4111 0.033 Uiso 1 1 calc R . . . .
C21 C 0.80384(14) -0.07446(11) 0.34502(12) 0.0336(3) Uani 1 1 d . . . . .
H21A H 0.7943 -0.1399 0.3073 0.050 Uiso 1 1 calc GR . . . .
H21B H 0.8693 -0.0379 0.3302 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.7303 -0.0358 0.3159 0.050 Uiso 1 1 calc GR . . . .
C15 C 0.97047(15) 0.12539(11) 0.92119(12) 0.0365(4) Uani 1 1 d . . . . .
H15A H 1.0309 0.1686 0.9061 0.055 Uiso 1 1 calc GR . . . .
H15B H 0.9995 0.1004 0.9990 0.055 Uiso 1 1 calc GR . . . .
H15C H 0.8975 0.1640 0.9109 0.055 Uiso 1 1 calc GR . . . .
C3 C 0.85336(14) 0.67261(10) 0.52384(13) 0.0355(4) Uani 1 1 d . . . . .
H3 H 0.8467 0.7427 0.5099 0.043 Uiso 1 1 calc R . . . .
C1 C 0.67331(14) 0.64965(11) 0.35946(13) 0.0384(4) Uani 1 1 d . . . . .
H1A H 0.7017 0.6602 0.2942 0.058 Uiso 1 1 calc GR . . . .
H1B H 0.6468 0.7137 0.3820 0.058 Uiso 1 1 calc GR . . . .
H1C H 0.6069 0.6022 0.3392 0.058 Uiso 1 1 calc GR . . . .
C5 C 0.95515(14) 0.53062(11) 0.63362(13) 0.0377(4) Uani 1 1 d . . . . .
H5 H 1.0175 0.5056 0.6958 0.045 Uiso 1 1 calc R . . . .
C4 C 0.94589(14) 0.63425(11) 0.61348(14) 0.0413(4) Uani 1 1 d . . . . .
H4 H 1.0026 0.6784 0.6609 0.050 Uiso 1 1 calc R . . . .
C18 C 0.80822(15) -0.15459(12) 0.73834(15) 0.0451(4) Uani 1 1 d . . . . .
H18A H 0.7333 -0.1585 0.6764 0.068 Uiso 1 1 calc GR . . . .
H18B H 0.7992 -0.1081 0.7962 0.068 Uiso 1 1 calc GR . . . .
H18C H 0.8292 -0.2213 0.7717 0.068 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.987(2) 0.3955(14) 1.0376(18) 0.100(6) Uani 0.25 1 d . . P D -1
Cl3 Cl 0.985(3) 0.5867(12) 0.9336(14) 0.126(6) Uani 0.25 1 d . . P D -1
C2 C 1.016(2) 0.5164(12) 1.0574(13) 0.093(4) Uani 0.25 1 d . . P D -1
H2A H 1.1005 0.5278 1.0999 0.110 Uiso 0.25 1 d . . P E -1
H2B H 0.9695 0.5469 1.1069 0.110 Uiso 0.25 1 d . . P F -1
Cl1 Cl 0.9763(19) 0.5966(17) 0.9596(17) 0.140(6) Uani 0.25 1 d . . P G -2
Cl4 Cl 0.9604(8) 0.3924(12) 1.0493(8) 0.0651(17) Uani 0.25 1 d . . P G -2
C8 C 1.0541(11) 0.4756(11) 0.9971(16) 0.059(2) Uani 0.25 1 d . . P G -2
H8A H 1.0662 0.4445 0.9305 0.067 Uiso 0.25 1 d . . P H -2
H8B H 1.1318 0.4828 1.0571 0.067 Uiso 0.25 1 d . . P I -2
O1WA O 1.1097(8) 0.3536(7) 0.7775(6) 0.0517(17) Uani 0.5 1 d . . P J 1
H1WC H 1.0478 0.3335 0.7234 0.077 Uiso 0.5 1 d . . P K 1
H1WD H 1.1481 0.2989 0.8034 0.077 Uiso 0.5 1 d . . P L 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
O14 C13 1.3726(15) . ?
O14 C15 1.4291(17) . ?
O17 C16 1.3797(15) . ?
O17 C18 1.4307(18) . ?
O20 C19 1.3675(15) . ?
O20 C21 1.4287(16) . ?
O10 C9 1.2562(16) . ?
N8 C6 1.3807(17) . ?
N8 C9 1.3348(17) . ?
N2 C7 1.3539(17) . ?
N2 C3 1.3391(18) . ?
N2 C1 1.4761(18) . ?
O1WB H1WA 0.851(8) . ?
O1WB H1WB 0.848(9) . ?
C19 C16 1.3948(19) . ?
C19 C22 1.3914(18) . ?
C16 C13 1.3995(19) . ?
C13 C12 1.3856(18) . ?
C12 H12 0.9300 . ?
C12 C11 1.3917(18) . ?
C6 C7 1.3960(18) . ?
C6 C5 1.4065(19) . ?
C11 C9 1.5125(17) . ?
C11 C22 1.3881(18) . ?
C7 H7 0.9300 . ?
C22 H22 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.368(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.373(2) . ?
C4 H4 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
Cl2 C2 1.62(2) . ?
Cl3 C2 1.707(18) . ?
C2 H2A 0.97(2) . ?
C2 H2B 1.00(2) . ?
Cl1 C8 1.81(2) . ?
Cl4 C8 1.787(18) . ?
C8 H8A 0.956(15) . ?
C8 H8B 0.973(16) . ?
O1WA H1WC 0.852(9) . ?
O1WA H1WD 0.849(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O14 C15 116.45(10) . . ?
C16 O17 C18 113.62(10) . . ?
C19 O20 C21 117.03(10) . . ?
C9 N8 C6 121.22(11) . . ?
C7 N2 C1 118.70(11) . . ?
C3 N2 C7 122.39(12) . . ?
C3 N2 C1 118.88(11) . . ?
H1WA O1WB H1WB 104.6(9) . . ?
O20 C19 C16 115.63(11) . . ?
O20 C19 C22 124.11(12) . . ?
C22 C19 C16 120.26(12) . . ?
O17 C16 C19 119.70(11) . . ?
O17 C16 C13 120.99(11) . . ?
C19 C16 C13 119.25(11) . . ?
O14 C13 C16 115.40(11) . . ?
O14 C13 C12 124.19(12) . . ?
C12 C13 C16 120.41(12) . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 119.92(12) . . ?
C11 C12 H12 120.0 . . ?
N8 C6 C7 127.04(12) . . ?
N8 C6 C5 117.14(12) . . ?
C7 C6 C5 115.79(12) . . ?
C12 C11 C9 120.50(11) . . ?
C22 C11 C12 120.14(12) . . ?
C22 C11 C9 119.34(11) . . ?
O10 C9 N8 127.63(12) . . ?
O10 C9 C11 118.78(11) . . ?
N8 C9 C11 113.58(11) . . ?
N2 C7 C6 121.11(12) . . ?
N2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C19 C22 H22 120.0 . . ?
C11 C22 C19 119.99(12) . . ?
C11 C22 H22 120.0 . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C3 H3 120.4 . . ?
N2 C3 C4 119.13(13) . . ?
C4 C3 H3 120.4 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.42(13) . . ?
C4 C5 H5 119.3 . . ?
C3 C4 C5 120.13(14) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Cl2 C2 Cl3 114.6(15) . . ?
Cl2 C2 H2A 111.1(19) . . ?
Cl2 C2 H2B 110.6(16) . . ?
Cl3 C2 H2A 106.6(17) . . ?
Cl3 C2 H2B 108.3(18) . . ?
H2A C2 H2B 105.0(13) . . ?
Cl1 C8 H8A 110.4(17) . . ?
Cl1 C8 H8B 112.3(13) . . ?
Cl4 C8 Cl1 108.0(10) . . ?
Cl4 C8 H8A 108.0(10) . . ?
Cl4 C8 H8B 108.4(14) . . ?
H8A C8 H8B 109.5(11) . . ?
H1WC O1WA H1WD 104.5(9) . . ?

_olex2_date_sample_data_collection 2017-08-24
_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 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.813
