# Electronic Supplementary Material (ESI) for ChemComm.
# 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_p170311f-p
_audit_block_doi                 10.5517/ccdc.csd.cc1pf65h
_database_code_depnum_ccdc_archive 'CCDC 1561816'
_audit_update_record             
;
2017-07-12 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;
_audit_creation_date             2017-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C41 H55 N O3'
_chemical_formula_sum            'C41 H55 N O3'
_chemical_formula_weight         609.86
_chemical_absolute_configuration s
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     MXQ-2-114
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.4864(8)
_cell_length_b                   11.3225(6)
_cell_length_c                   22.7080(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.085(6)
_cell_angle_gamma                90
_cell_volume                     3578.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6261
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      24.9110
_cell_measurement_theta_min      3.2910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.132
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.1122
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24100
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         2.927
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 16.2116
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   92.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396   19.0000    0.0000 114

#__ type_ start__ end____ width___ exp.time_
  2 omega   62.00   88.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   22.00   61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396  -99.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   25.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396   77.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   60.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396  -99.0000   60.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega  -47.00   34.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396  -57.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  7 omega  -71.00  -46.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2521  178.0000    0.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0259580000
_diffrn_orient_matrix_UB_12      0.0238358000
_diffrn_orient_matrix_UB_13      0.0287159000
_diffrn_orient_matrix_UB_21      -0.0149490000
_diffrn_orient_matrix_UB_22      0.0576215000
_diffrn_orient_matrix_UB_23      -0.0107788000
_diffrn_orient_matrix_UB_31      -0.0412027000
_diffrn_orient_matrix_UB_32      -0.0058499000
_diffrn_orient_matrix_UB_33      0.0108384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                7938
_reflns_number_total             11746
_reflns_odcompleteness_completeness 99.78
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     821
_refine_ls_number_reflns         11746
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.027
_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)+(0.0460P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1492
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C15(H15), C16(H16), C70(H70), C25(H25), C65(H65), C66(H66),
 C29(H29), C73(H73), C57(H57), C35(H35), C32(H32), C76(H76), C56(H56), C39(H39),
  C80(H80)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C72(H72A,H72B), C26(H26A,H26B), C27(H27A,
 H27B), C61(H61A,H61B), C23(H23A,H23B), C67(H67A,H67B), C71(H71A,H71B),
 C60(H60A,H60B), C37(H37A,H37B), C68(H68A,H68B), C30(H30A,H30B), C31(H31A,H31B),
  C36(H36A,H36B), C64(H64A,H64B), C77(H77A,H77B), C78(H78A,H78B), C38(H38A,
 H38B), C79(H79A,H79B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2A), N1(H1), C22(H22), C46(H46), C63(H63), C42(H42), C45(H45), C12(H12),
 C1(H1A), C5(H5), C8(H8), C43(H43), C44(H44), C9(H9), C10(H10), C4(H4), C3(H3),
 C11(H11), C2(H2), C53(H53), C49(H49), C52(H52), C50(H50), C51(H51)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C33(H33A,H33B,H33C), C74(H74A,H74B,H74C), C62(H62A,H62B,
 H62C), C34(H34A,H34B,H34C), C75(H75A,H75B,H75C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C), C81(H81A,H81B,H81C), C82(H82A,H82B,H82C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O2 O 0.9388(2) 0.5723(3) 0.18020(15) 0.0345(9) Uani 1 1 d . . . . .
O3 O 0.9433(3) 0.3783(3) 0.15841(16) 0.0377(9) Uani 1 1 d . . . . .
O4 O 0.1433(3) 0.4091(3) 0.80208(16) 0.0402(10) Uani 1 1 d . . . . .
O6 O -0.1160(2) 0.6468(3) 0.77475(16) 0.0356(9) Uani 1 1 d . . . . .
N2 N 0.0722(3) 0.5886(4) 0.78607(18) 0.0308(10) Uani 1 1 d . . . . .
H2A H 0.0727 0.6600 0.7990 0.037 Uiso 1 1 calc R . . . .
N1 N 0.7439(3) 0.6295(4) 0.16390(18) 0.0311(10) Uani 1 1 d . . . . .
H1 H 0.7551 0.7021 0.1746 0.037 Uiso 1 1 calc R . . . .
O1 O 0.6816(3) 0.5055(4) 0.08583(18) 0.0575(12) Uani 1 1 d . . . . .
C24 C 0.6419(3) 0.5333(4) 0.3533(2) 0.0255(11) Uani 1 1 d . . . . .
H24 H 0.6034 0.6016 0.3345 0.031 Uiso 1 1 calc R . . . .
C19 C 0.8883(3) 0.6271(5) 0.3299(2) 0.0277(12) Uani 1 1 d . . . . .
H19A H 0.9078 0.6920 0.3585 0.033 Uiso 1 1 calc R . . . .
H19B H 0.9170 0.5555 0.3505 0.033 Uiso 1 1 calc R . . . .
C59 C 0.0525(3) 0.6773(4) 0.6440(2) 0.0245(12) Uani 1 1 d . . . . .
C58 C 0.0385(3) 0.5580(4) 0.6720(2) 0.0258(12) Uani 1 1 d . . . . .
C15 C 0.8975(3) 0.5481(5) 0.2303(2) 0.0288(12) Uani 1 1 d . . . . .
H15 H 0.9247 0.4744 0.2504 0.035 Uiso 1 1 calc R . . . .
C18 C 0.7768(3) 0.6150(4) 0.3128(2) 0.0248(11) Uani 1 1 d . . . . .
C48 C 0.1365(4) 0.5105(5) 0.8194(2) 0.0300(12) Uani 1 1 d . . . . .
C20 C 0.9272(4) 0.6485(5) 0.2749(2) 0.0305(13) Uani 1 1 d . . . . .
H20A H 0.9020 0.7223 0.2552 0.037 Uiso 1 1 calc R . . . .
H20B H 0.9967 0.6541 0.2884 0.037 Uiso 1 1 calc R . . . .
C17 C 0.7441(3) 0.5273(4) 0.2601(2) 0.0258(12) Uani 1 1 d . . . . .
C16 C 0.7884(4) 0.5358(5) 0.2070(2) 0.0283(12) Uani 1 1 d . . . . .
H16 H 0.7752 0.4609 0.1846 0.034 Uiso 1 1 calc R . . . .
C28 C 0.6383(3) 0.5922(4) 0.4627(2) 0.0254(11) Uani 1 1 d . . . . .
C69 C 0.1802(3) 0.6541(4) 0.4857(2) 0.0252(11) Uani 1 1 d . . . . .
C72 C 0.2196(4) 0.4770(5) 0.4356(2) 0.0310(13) Uani 1 1 d . . . . .
H72A H 0.1856 0.4250 0.4028 0.037 Uiso 1 1 calc R . . . .
H72B H 0.2878 0.4719 0.4393 0.037 Uiso 1 1 calc R . . . .
C22 C 0.6764(3) 0.4476(5) 0.2588(2) 0.0298(12) Uani 1 1 d . . . . .
H22 H 0.6594 0.3974 0.2251 0.036 Uiso 1 1 calc R . . . .
C14 C 0.6859(4) 0.6044(5) 0.1079(2) 0.0313(12) Uani 1 1 d . . . . .
C70 C 0.1409(3) 0.5441(4) 0.5100(2) 0.0268(12) Uani 1 1 d . . . . .
H70 H 0.0757 0.5328 0.4832 0.032 Uiso 1 1 calc R . . . .
C26 C 0.7819(3) 0.6457(5) 0.4260(2) 0.0310(13) Uani 1 1 d . . . . .
H26A H 0.7583 0.7249 0.4145 0.037 Uiso 1 1 calc R . . . .
H26B H 0.8515 0.6493 0.4385 0.037 Uiso 1 1 calc R . . . .
C25 C 0.7502(3) 0.5663(4) 0.3697(2) 0.0253(11) Uani 1 1 d . . . . .
H25 H 0.7857 0.4922 0.3806 0.030 Uiso 1 1 calc R . . . .
C65 C 0.1303(4) 0.5545(4) 0.5748(2) 0.0261(11) Uani 1 1 d . . . . .
H65 H 0.1937 0.5681 0.6036 0.031 Uiso 1 1 calc R . . . .
C27 C 0.7478(3) 0.6066(5) 0.4814(2) 0.0285(12) Uani 1 1 d . . . . .
H27A H 0.7779 0.5323 0.4971 0.034 Uiso 1 1 calc R . . . .
H27B H 0.7666 0.6651 0.5137 0.034 Uiso 1 1 calc R . . . .
C66 C 0.0640(4) 0.6590(5) 0.5783(2) 0.0268(12) Uani 1 1 d . . . . .
H66 H 0.0002 0.6378 0.5521 0.032 Uiso 1 1 calc R . . . .
C7 C 0.9576(4) 0.4797(5) 0.1476(2) 0.0328(13) Uani 1 1 d . . . . .
C46 C 0.2235(4) 0.6733(5) 0.8893(3) 0.0350(13) Uani 1 1 d . . . . .
H46 H 0.2012 0.7276 0.8578 0.042 Uiso 1 1 calc R . . . .
C29 C 0.6147(3) 0.4980(4) 0.4110(2) 0.0268(12) Uani 1 1 d . . . . .
H29 H 0.6534 0.4284 0.4275 0.032 Uiso 1 1 calc R . . . .
C61 C -0.0704(4) 0.7575(5) 0.6986(2) 0.0324(13) Uani 1 1 d . . . . .
H61A H -0.0211 0.7960 0.7306 0.039 Uiso 1 1 calc R . . . .
H61B H -0.1291 0.8033 0.6916 0.039 Uiso 1 1 calc R . . . .
C21 C 0.7301(4) 0.7369(5) 0.2927(2) 0.0307(12) Uani 1 1 d . . . . .
H21A H 0.7605 0.7733 0.2648 0.046 Uiso 1 1 calc GR . . . .
H21B H 0.7379 0.7863 0.3281 0.046 Uiso 1 1 calc GR . . . .
H21C H 0.6629 0.7265 0.2729 0.046 Uiso 1 1 calc GR . . . .
O5 O -0.1874(4) 0.4694(5) 0.7596(2) 0.0798(17) Uani 1 1 d . . . . .
C33 C 0.5861(4) 0.7091(4) 0.4415(2) 0.0298(12) Uani 1 1 d . . . . .
H33A H 0.6000 0.7351 0.4046 0.045 Uiso 1 1 calc GR . . . .
H33B H 0.6075 0.7677 0.4729 0.045 Uiso 1 1 calc GR . . . .
H33C H 0.5181 0.6978 0.4337 0.045 Uiso 1 1 calc GR . . . .
C73 C 0.1836(4) 0.6075(5) 0.4218(2) 0.0288(12) Uani 1 1 d . . . . .
H73 H 0.1170 0.6030 0.3963 0.035 Uiso 1 1 calc R . . . .
C23 C 0.6253(4) 0.4323(5) 0.3072(2) 0.0312(13) Uani 1 1 d . . . . .
H23A H 0.6465 0.3592 0.3290 0.037 Uiso 1 1 calc R . . . .
H23B H 0.5569 0.4254 0.2876 0.037 Uiso 1 1 calc R . . . .
C57 C 0.0018(4) 0.5553(5) 0.7288(2) 0.0304(12) Uani 1 1 d . . . . .
H57 H -0.0185 0.4742 0.7336 0.037 Uiso 1 1 calc R . . . .
C67 C 0.0940(4) 0.7717(5) 0.5502(2) 0.0324(13) Uani 1 1 d . . . . .
H67A H 0.0451 0.8317 0.5474 0.039 Uiso 1 1 calc R . . . .
H67B H 0.1534 0.8012 0.5775 0.039 Uiso 1 1 calc R . . . .
C13 C 0.6237(4) 0.7027(5) 0.0741(2) 0.0308(13) Uani 1 1 d . . . . .
C71 C 0.1997(4) 0.4416(5) 0.4964(2) 0.0322(13) Uani 1 1 d . . . . .
H71A H 0.1637 0.3684 0.4919 0.039 Uiso 1 1 calc R . . . .
H71B H 0.2591 0.4324 0.5287 0.039 Uiso 1 1 calc R . . . .
C60 C -0.0388(4) 0.7524(5) 0.6393(2) 0.0300(12) Uani 1 1 d . . . . .
H60A H -0.0270 0.8322 0.6277 0.036 Uiso 1 1 calc R . . . .
H60B H -0.0912 0.7203 0.6068 0.036 Uiso 1 1 calc R . . . .
C47 C 0.1981(4) 0.5550(5) 0.8797(2) 0.0313(13) Uani 1 1 d . . . . .
C63 C 0.0527(3) 0.4557(5) 0.6481(2) 0.0295(12) Uani 1 1 d . . . . .
H63 H 0.0398 0.3874 0.6672 0.035 Uiso 1 1 calc R . . . .
C35 C 0.5772(4) 0.6070(5) 0.5625(2) 0.0306(12) Uani 1 1 d . . . . .
H35 H 0.5289 0.6669 0.5442 0.037 Uiso 1 1 calc R . . . .
C32 C 0.5948(3) 0.5326(5) 0.5110(2) 0.0277(12) Uani 1 1 d . . . . .
H32 H 0.6388 0.4690 0.5302 0.033 Uiso 1 1 calc R . . . .
C37 C 0.5098(4) 0.5979(6) 0.6562(2) 0.0415(15) Uani 1 1 d . . . . .
H37A H 0.5682 0.6268 0.6849 0.050 Uiso 1 1 calc R . . . .
H37B H 0.4719 0.6661 0.6382 0.050 Uiso 1 1 calc R . . . .
C74 C 0.2820(4) 0.6849(5) 0.5240(2) 0.0354(13) Uani 1 1 d . . . . .
H74A H 0.3244 0.6205 0.5227 0.053 Uiso 1 1 calc GR . . . .
H74B H 0.2818 0.6990 0.5657 0.053 Uiso 1 1 calc GR . . . .
H74C H 0.3036 0.7546 0.5077 0.053 Uiso 1 1 calc GR . . . .
C62 C 0.1405(3) 0.7408(5) 0.6853(2) 0.0302(12) Uani 1 1 d . . . . .
H62A H 0.1979 0.6992 0.6844 0.045 Uiso 1 1 calc GR . . . .
H62B H 0.1355 0.7428 0.7266 0.045 Uiso 1 1 calc GR . . . .
H62C H 0.1432 0.8200 0.6708 0.045 Uiso 1 1 calc GR . . . .
C68 C 0.1085(4) 0.7534(5) 0.4862(2) 0.0322(13) Uani 1 1 d . . . . .
H68A H 0.0472 0.7345 0.4574 0.039 Uiso 1 1 calc R . . . .
H68B H 0.1316 0.8263 0.4729 0.039 Uiso 1 1 calc R . . . .
C76 C 0.2403(4) 0.6741(5) 0.3845(2) 0.0341(13) Uani 1 1 d . . . . .
H76 H 0.3071 0.6788 0.4097 0.041 Uiso 1 1 calc R . . . .
C56 C -0.0873(4) 0.6345(5) 0.7186(2) 0.0324(13) Uani 1 1 d . . . . .
H56 H -0.1402 0.5986 0.6871 0.039 Uiso 1 1 calc R . . . .
C30 C 0.5103(3) 0.4644(5) 0.4050(2) 0.0360(14) Uani 1 1 d . . . . .
H30A H 0.4968 0.3848 0.3891 0.043 Uiso 1 1 calc R . . . .
H30B H 0.4664 0.5187 0.3781 0.043 Uiso 1 1 calc R . . . .
C6 C 0.9991(4) 0.5222(5) 0.0983(2) 0.0357(14) Uani 1 1 d . . . . .
C42 C 0.2318(4) 0.4749(5) 0.9268(2) 0.0373(14) Uani 1 1 d . . . . .
H42 H 0.2163 0.3953 0.9205 0.045 Uiso 1 1 calc R . . . .
C31 C 0.5024(4) 0.4730(5) 0.4709(2) 0.0381(14) Uani 1 1 d . . . . .
H31A H 0.4955 0.3948 0.4866 0.046 Uiso 1 1 calc R . . . .
H31B H 0.4465 0.5195 0.4718 0.046 Uiso 1 1 calc R . . . .
C45 C 0.2818(4) 0.7111(6) 0.9453(3) 0.0423(15) Uani 1 1 d . . . . .
H45 H 0.2990 0.7902 0.9515 0.051 Uiso 1 1 calc R . . . .
C36 C 0.5368(4) 0.5300(5) 0.6058(2) 0.0393(14) Uani 1 1 d . . . . .
H36A H 0.4803 0.4888 0.5815 0.047 Uiso 1 1 calc R . . . .
H36B H 0.5844 0.4709 0.6245 0.047 Uiso 1 1 calc R . . . .
C64 C 0.0880(4) 0.4416(5) 0.5927(2) 0.0335(13) Uani 1 1 d . . . . .
H64A H 0.0350 0.4162 0.5586 0.040 Uiso 1 1 calc R . . . .
H64B H 0.1365 0.3801 0.6004 0.040 Uiso 1 1 calc R . . . .
C12 C 0.5955(4) 0.7953(5) 0.1048(3) 0.0421(15) Uani 1 1 d . . . . .
H12 H 0.6182 0.8006 0.1472 0.051 Uiso 1 1 calc R . . . .
C77 C 0.2404(4) 0.6079(6) 0.3261(2) 0.0425(15) Uani 1 1 d . . . . .
H77A H 0.2610 0.5275 0.3372 0.051 Uiso 1 1 calc R . . . .
H77B H 0.1747 0.6043 0.3003 0.051 Uiso 1 1 calc R . . . .
C78 C 0.3025(4) 0.6576(5) 0.2878(3) 0.0461(16) Uani 1 1 d . . . . .
H78A H 0.3653 0.6774 0.3146 0.055 Uiso 1 1 calc R . . . .
H78B H 0.2735 0.7297 0.2679 0.055 Uiso 1 1 calc R . . . .
C34 C 0.6674(4) 0.6709(5) 0.5999(3) 0.0424(15) Uani 1 1 d . . . . .
H34A H 0.6852 0.7304 0.5749 0.064 Uiso 1 1 calc GR . . . .
H34B H 0.7189 0.6151 0.6131 0.064 Uiso 1 1 calc GR . . . .
H34C H 0.6547 0.7073 0.6350 0.064 Uiso 1 1 calc GR . . . .
C1 C 1.0032(4) 0.4438(6) 0.0523(3) 0.0470(16) Uani 1 1 d . . . . .
H1A H 0.9819 0.3665 0.0533 0.056 Uiso 1 1 calc R . . . .
C5 C 1.0318(4) 0.6361(5) 0.0973(3) 0.0435(15) Uani 1 1 d . . . . .
H5 H 1.0287 0.6888 0.1282 0.052 Uiso 1 1 calc R . . . .
C8 C 0.5892(4) 0.6962(5) 0.0106(3) 0.0413(15) Uani 1 1 d . . . . .
H8 H 0.6073 0.6337 -0.0103 0.050 Uiso 1 1 calc R . . . .
C75 C 0.2042(4) 0.8013(5) 0.3697(3) 0.0438(15) Uani 1 1 d . . . . .
H75A H 0.2130 0.8448 0.4072 0.066 Uiso 1 1 calc GR . . . .
H75B H 0.1372 0.8001 0.3478 0.066 Uiso 1 1 calc GR . . . .
H75C H 0.2399 0.8386 0.3450 0.066 Uiso 1 1 calc GR . . . .
C39 C 0.4254(5) 0.5961(6) 0.7421(3) 0.0533(18) Uani 1 1 d . . . . .
H39 H 0.3930 0.6687 0.7238 0.064 Uiso 1 1 calc R . . . .
C38 C 0.4538(4) 0.5273(6) 0.6915(3) 0.0489(17) Uani 1 1 d . . . . .
H38A H 0.4920 0.4597 0.7099 0.059 Uiso 1 1 calc R . . . .
H38B H 0.3958 0.4976 0.6628 0.059 Uiso 1 1 calc R . . . .
C55 C -0.1637(5) 0.5559(6) 0.7908(3) 0.0489(16) Uani 1 1 d . . . . .
C43 C 0.2884(4) 0.5130(6) 0.9832(3) 0.0440(16) Uani 1 1 d . . . . .
H43 H 0.3091 0.4595 1.0152 0.053 Uiso 1 1 calc R . . . .
C44 C 0.3142(4) 0.6302(6) 0.9919(3) 0.0456(16) Uani 1 1 d . . . . .
H44 H 0.3537 0.6549 1.0295 0.055 Uiso 1 1 calc R . . . .
C9 C 0.5283(4) 0.7822(6) -0.0214(3) 0.0495(17) Uani 1 1 d . . . . .
H9 H 0.5067 0.7779 -0.0639 0.059 Uiso 1 1 calc R . . . .
C10 C 0.4987(4) 0.8744(6) 0.0086(3) 0.0479(16) Uani 1 1 d . . . . .
H10 H 0.4567 0.9313 -0.0132 0.057 Uiso 1 1 calc R . . . .
C4 C 1.0693(4) 0.6724(6) 0.0505(3) 0.0488(17) Uani 1 1 d . . . . .
H4 H 1.0929 0.7488 0.0503 0.059 Uiso 1 1 calc R . . . .
C3 C 1.0716(5) 0.5944(6) 0.0038(3) 0.0544(18) Uani 1 1 d . . . . .
H3 H 1.0953 0.6191 -0.0283 0.065 Uiso 1 1 calc R . . . .
C11 C 0.5328(4) 0.8807(6) 0.0718(3) 0.0507(17) Uani 1 1 d . . . . .
H11 H 0.5136 0.9427 0.0926 0.061 Uiso 1 1 calc R . . . .
C79 C 0.3143(4) 0.5698(6) 0.2390(3) 0.0554(18) Uani 1 1 d . . . . .
H79A H 0.2529 0.5606 0.2085 0.066 Uiso 1 1 calc R . . . .
H79B H 0.3322 0.4935 0.2582 0.066 Uiso 1 1 calc R . . . .
C2 C 1.0388(5) 0.4806(6) 0.0049(3) 0.0549(18) Uani 1 1 d . . . . .
H2 H 1.0406 0.4283 -0.0264 0.066 Uiso 1 1 calc R . . . .
C53 C -0.1606(5) 0.6783(7) 0.8836(3) 0.061(2) Uani 1 1 d . . . . .
H53 H -0.1376 0.7423 0.8662 0.073 Uiso 1 1 calc R . . . .
C40 C 0.3563(5) 0.5274(6) 0.7668(3) 0.0608(19) Uani 1 1 d . . . . .
H40A H 0.3854 0.4542 0.7836 0.091 Uiso 1 1 calc GR . . . .
H40B H 0.2993 0.5115 0.7343 0.091 Uiso 1 1 calc GR . . . .
H40C H 0.3400 0.5723 0.7983 0.091 Uiso 1 1 calc GR . . . .
C54 C -0.1800(4) 0.5729(7) 0.8519(3) 0.0528(18) Uani 1 1 d . . . . .
C49 C -0.2153(5) 0.4784(8) 0.8774(3) 0.075(2) Uani 1 1 d . . . . .
H49 H -0.2296 0.4075 0.8562 0.089 Uiso 1 1 calc R . . . .
C41 C 0.5152(5) 0.6319(8) 0.7932(3) 0.086(3) Uani 1 1 d . . . . .
H41A H 0.5535 0.6852 0.7770 0.130 Uiso 1 1 calc GR . . . .
H41B H 0.5522 0.5627 0.8090 0.130 Uiso 1 1 calc GR . . . .
H41C H 0.4960 0.6701 0.8257 0.130 Uiso 1 1 calc GR . . . .
C52 C -0.1752(5) 0.6891(9) 0.9409(3) 0.077(3) Uani 1 1 d . . . . .
H52 H -0.1624 0.7604 0.9619 0.093 Uiso 1 1 calc R . . . .
C80 C 0.3905(7) 0.6075(8) 0.2065(3) 0.083(3) Uani 1 1 d . . . . .
H80 H 0.4522 0.6109 0.2381 0.099 Uiso 1 1 calc R . . . .
C50 C -0.2296(6) 0.4905(10) 0.9360(4) 0.090(3) Uani 1 1 d . . . . .
H50 H -0.2533 0.4274 0.9536 0.108 Uiso 1 1 calc R . . . .
C51 C -0.2086(6) 0.5947(11) 0.9669(4) 0.087(3) Uani 1 1 d . . . . .
H51 H -0.2170 0.6018 1.0059 0.104 Uiso 1 1 calc R . . . .
C81 C 0.3994(7) 0.5091(8) 0.1612(3) 0.101(3) Uani 1 1 d . . . . .
H81A H 0.3379 0.4957 0.1324 0.152 Uiso 1 1 calc GR . . . .
H81B H 0.4212 0.4376 0.1835 0.152 Uiso 1 1 calc GR . . . .
H81C H 0.4447 0.5328 0.1396 0.152 Uiso 1 1 calc GR . . . .
C82 C 0.3758(7) 0.7225(9) 0.1774(4) 0.113(4) Uani 1 1 d . . . . .
H82A H 0.3912 0.7829 0.2082 0.170 Uiso 1 1 calc GR . . . .
H82B H 0.3098 0.7303 0.1539 0.170 Uiso 1 1 calc GR . . . .
H82C H 0.4165 0.7304 0.1507 0.170 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C15 1.451(5) . ?
O2 C7 1.353(6) . ?
O3 C7 1.204(6) . ?
O4 C48 1.226(6) . ?
O6 C56 1.454(6) . ?
O6 C55 1.345(7) . ?
N2 C48 1.354(6) . ?
N2 C57 1.462(6) . ?
N1 C16 1.466(6) . ?
N1 C14 1.345(6) . ?
O1 C14 1.221(6) . ?
C24 C25 1.554(6) . ?
C24 C29 1.523(6) . ?
C24 C23 1.523(7) . ?
C19 C18 1.559(6) . ?
C19 C20 1.524(6) . ?
C59 C58 1.530(7) . ?
C59 C66 1.560(7) . ?
C59 C60 1.551(6) . ?
C59 C62 1.537(7) . ?
C58 C57 1.525(7) . ?
C58 C63 1.319(7) . ?
C15 C20 1.504(7) . ?
C15 C16 1.528(7) . ?
C18 C17 1.525(6) . ?
C18 C25 1.550(6) . ?
C18 C21 1.549(7) . ?
C48 C47 1.500(7) . ?
C17 C16 1.518(7) . ?
C17 C22 1.326(7) . ?
C28 C27 1.533(6) . ?
C28 C29 1.552(7) . ?
C28 C33 1.535(7) . ?
C28 C32 1.562(6) . ?
C69 C70 1.535(7) . ?
C69 C73 1.556(7) . ?
C69 C74 1.531(7) . ?
C69 C68 1.533(7) . ?
C72 C73 1.569(7) . ?
C72 C71 1.539(7) . ?
C22 C23 1.496(6) . ?
C14 C13 1.503(7) . ?
C70 C65 1.527(6) . ?
C70 C71 1.521(7) . ?
C26 C25 1.525(7) . ?
C26 C27 1.539(6) . ?
C65 C66 1.540(7) . ?
C65 C64 1.520(7) . ?
C66 C67 1.542(7) . ?
C7 C6 1.491(7) . ?
C46 C47 1.390(7) . ?
C46 C45 1.386(8) . ?
C29 C30 1.527(6) . ?
C61 C60 1.539(6) . ?
C61 C56 1.506(7) . ?
O5 C55 1.202(8) . ?
C73 C76 1.532(7) . ?
C57 C56 1.535(7) . ?
C67 C68 1.538(7) . ?
C13 C12 1.381(7) . ?
C13 C8 1.391(7) . ?
C47 C42 1.384(7) . ?
C63 C64 1.492(7) . ?
C35 C32 1.519(7) . ?
C35 C36 1.545(7) . ?
C35 C34 1.528(7) . ?
C32 C31 1.549(7) . ?
C37 C36 1.518(7) . ?
C37 C38 1.517(7) . ?
C76 C77 1.523(7) . ?
C76 C75 1.538(8) . ?
C30 C31 1.536(7) . ?
C6 C1 1.385(7) . ?
C6 C5 1.376(8) . ?
C42 C43 1.384(7) . ?
C45 C44 1.379(8) . ?
C12 C11 1.394(8) . ?
C77 C78 1.521(7) . ?
C78 C79 1.533(8) . ?
C1 C2 1.380(7) . ?
C5 C4 1.384(7) . ?
C8 C9 1.378(8) . ?
C39 C38 1.534(7) . ?
C39 C40 1.494(8) . ?
C39 C41 1.539(9) . ?
C55 C54 1.482(8) . ?
C43 C44 1.377(9) . ?
C9 C10 1.378(8) . ?
C10 C11 1.384(8) . ?
C4 C3 1.387(8) . ?
C3 C2 1.377(9) . ?
C79 C80 1.548(9) . ?
C53 C54 1.382(9) . ?
C53 C52 1.380(9) . ?
C54 C49 1.382(9) . ?
C49 C50 1.408(10) . ?
C52 C51 1.374(12) . ?
C80 C81 1.546(10) . ?
C80 C82 1.448(12) . ?
C50 C51 1.363(12) . ?

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
C7 O2 C15 118.1(4) . . ?
C55 O6 C56 117.3(4) . . ?
C48 N2 C57 122.1(4) . . ?
C14 N1 C16 121.5(4) . . ?
C29 C24 C25 109.9(4) . . ?
C23 C24 C25 107.6(4) . . ?
C23 C24 C29 111.4(4) . . ?
C20 C19 C18 113.7(4) . . ?
C58 C59 C66 110.0(4) . . ?
C58 C59 C60 107.7(4) . . ?
C58 C59 C62 110.0(4) . . ?
C60 C59 C66 108.8(4) . . ?
C62 C59 C66 110.9(4) . . ?
C62 C59 C60 109.4(4) . . ?
C57 C58 C59 119.1(4) . . ?
C63 C58 C59 123.4(4) . . ?
C63 C58 C57 117.5(4) . . ?
O2 C15 C20 106.4(4) . . ?
O2 C15 C16 110.9(4) . . ?
C20 C15 C16 112.2(4) . . ?
C17 C18 C19 109.1(4) . . ?
C17 C18 C25 109.1(4) . . ?
C17 C18 C21 109.5(4) . . ?
C25 C18 C19 107.7(4) . . ?
C21 C18 C19 109.5(4) . . ?
C21 C18 C25 111.9(4) . . ?
O4 C48 N2 122.4(5) . . ?
O4 C48 C47 121.8(5) . . ?
N2 C48 C47 115.7(5) . . ?
C15 C20 C19 109.3(4) . . ?
C16 C17 C18 118.2(4) . . ?
C22 C17 C18 121.9(4) . . ?
C22 C17 C16 119.8(5) . . ?
N1 C16 C15 112.7(4) . . ?
N1 C16 C17 111.9(4) . . ?
C17 C16 C15 110.8(4) . . ?
C27 C28 C29 106.1(4) . . ?
C27 C28 C33 112.1(4) . . ?
C27 C28 C32 116.1(4) . . ?
C29 C28 C32 100.8(4) . . ?
C33 C28 C29 111.6(4) . . ?
C33 C28 C32 109.5(4) . . ?
C70 C69 C73 99.8(4) . . ?
C74 C69 C70 112.0(4) . . ?
C74 C69 C73 109.5(4) . . ?
C74 C69 C68 112.1(4) . . ?
C68 C69 C70 105.8(4) . . ?
C68 C69 C73 116.9(4) . . ?
C71 C72 C73 106.8(4) . . ?
C17 C22 C23 125.1(5) . . ?
N1 C14 C13 117.1(5) . . ?
O1 C14 N1 122.0(5) . . ?
O1 C14 C13 120.9(5) . . ?
C65 C70 C69 115.6(4) . . ?
C71 C70 C69 105.2(4) . . ?
C71 C70 C65 117.8(4) . . ?
C25 C26 C27 115.1(4) . . ?
C18 C25 C24 110.7(4) . . ?
C26 C25 C24 113.2(4) . . ?
C26 C25 C18 113.7(4) . . ?
C70 C65 C66 109.8(4) . . ?
C64 C65 C70 110.4(4) . . ?
C64 C65 C66 109.2(4) . . ?
C28 C27 C26 110.3(4) . . ?
C65 C66 C59 112.5(4) . . ?
C65 C66 C67 111.4(4) . . ?
C67 C66 C59 113.7(4) . . ?
O2 C7 C6 110.2(5) . . ?
O3 C7 O2 123.8(5) . . ?
O3 C7 C6 126.0(5) . . ?
C45 C46 C47 120.5(6) . . ?
C24 C29 C28 114.5(4) . . ?
C24 C29 C30 118.3(4) . . ?
C30 C29 C28 104.2(4) . . ?
C56 C61 C60 110.0(4) . . ?
C69 C73 C72 103.2(4) . . ?
C76 C73 C69 120.6(4) . . ?
C76 C73 C72 112.0(4) . . ?
C22 C23 C24 113.7(4) . . ?
N2 C57 C58 115.3(4) . . ?
N2 C57 C56 109.5(4) . . ?
C58 C57 C56 109.7(4) . . ?
C68 C67 C66 114.0(4) . . ?
C12 C13 C14 121.6(5) . . ?
C12 C13 C8 119.4(5) . . ?
C8 C13 C14 118.8(5) . . ?
C70 C71 C72 103.8(4) . . ?
C61 C60 C59 114.6(4) . . ?
C46 C47 C48 122.1(5) . . ?
C42 C47 C48 118.6(5) . . ?
C42 C47 C46 119.3(5) . . ?
C58 C63 C64 124.7(5) . . ?
C32 C35 C36 110.5(4) . . ?
C32 C35 C34 112.9(4) . . ?
C34 C35 C36 109.3(4) . . ?
C35 C32 C28 119.2(4) . . ?
C35 C32 C31 113.1(4) . . ?
C31 C32 C28 103.1(4) . . ?
C38 C37 C36 114.8(5) . . ?
C69 C68 C67 112.1(4) . . ?
C73 C76 C75 112.3(4) . . ?
C77 C76 C73 111.7(5) . . ?
C77 C76 C75 110.7(5) . . ?
O6 C56 C61 106.6(4) . . ?
O6 C56 C57 110.9(4) . . ?
C61 C56 C57 112.7(4) . . ?
C29 C30 C31 103.6(4) . . ?
C1 C6 C7 118.1(5) . . ?
C5 C6 C7 121.8(5) . . ?
C5 C6 C1 120.2(5) . . ?
C47 C42 C43 120.1(6) . . ?
C30 C31 C32 108.4(4) . . ?
C44 C45 C46 119.4(6) . . ?
C37 C36 C35 114.6(5) . . ?
C63 C64 C65 113.1(4) . . ?
C13 C12 C11 119.8(5) . . ?
C78 C77 C76 117.3(5) . . ?
C77 C78 C79 112.0(5) . . ?
C2 C1 C6 119.9(6) . . ?
C6 C5 C4 120.0(5) . . ?
C9 C8 C13 120.2(6) . . ?
C38 C39 C41 110.7(6) . . ?
C40 C39 C38 111.3(5) . . ?
C40 C39 C41 111.6(6) . . ?
C37 C38 C39 114.9(5) . . ?
O6 C55 C54 112.4(6) . . ?
O5 C55 O6 123.2(5) . . ?
O5 C55 C54 124.4(6) . . ?
C44 C43 C42 120.1(6) . . ?
C43 C44 C45 120.6(6) . . ?
C8 C9 C10 121.0(6) . . ?
C9 C10 C11 118.8(6) . . ?
C5 C4 C3 119.8(6) . . ?
C2 C3 C4 120.0(6) . . ?
C10 C11 C12 120.8(6) . . ?
C78 C79 C80 113.8(6) . . ?
C3 C2 C1 120.2(6) . . ?
C52 C53 C54 120.4(7) . . ?
C53 C54 C55 122.5(6) . . ?
C53 C54 C49 119.7(6) . . ?
C49 C54 C55 117.8(7) . . ?
C54 C49 C50 119.3(8) . . ?
C51 C52 C53 120.1(9) . . ?
C81 C80 C79 108.7(7) . . ?
C82 C80 C79 115.6(7) . . ?
C82 C80 C81 111.9(6) . . ?
C51 C50 C49 120.1(8) . . ?
C50 C51 C52 120.5(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p170209c
_database_code_depnum_ccdc_archive 'CCDC 1561818'
_audit_update_record             
;
2017-07-12 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;
_audit_creation_date             2017-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 Cl3 I2 N O'
_chemical_formula_sum            'C12 H14 Cl3 I2 N O'
_chemical_formula_weight         548.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N I'
_chemical_oxdiff_usercomment     MXQ-1-1-128
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'
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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7496(5)
_cell_length_b                   10.1118(3)
_cell_length_c                   12.9485(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.469(3)
_cell_angle_gamma                90
_cell_volume                     1658.71(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5767
_cell_measurement_temperature    298(10)
_cell_measurement_theta_max      28.4510
_cell_measurement_theta_min      3.6880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10264
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.929
_diffrn_ambient_temperature      298(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  36.00   1.00    2.50    --   18.94 -57.00 -60.00   30
  2  ω      1.00  57.00   1.00    2.50    --   18.94 -99.00 -90.00   56
  3  ω    -46.00 -20.00   1.00    2.50    --   18.94 -77.00  60.00   26
  4  ω    -63.00  31.00   1.00    2.50    --  -19.25  19.00   0.00   94
  5  ω    -10.00  78.00   1.00    2.50    --   18.94  77.00  60.00   88
  6  ω     -9.00  86.00   1.00    2.50    --   18.94  77.00-180.00   95
;
_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      0.0503151000
_diffrn_orient_matrix_UB_12      0.0210403000
_diffrn_orient_matrix_UB_13      -0.0120388000
_diffrn_orient_matrix_UB_21      0.0223303000
_diffrn_orient_matrix_UB_22      -0.0604627000
_diffrn_orient_matrix_UB_23      0.0195808000
_diffrn_orient_matrix_UB_31      -0.0102647000
_diffrn_orient_matrix_UB_32      -0.0286600000
_diffrn_orient_matrix_UB_33      -0.0501007000
_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                2555
_reflns_number_total             2881
_reflns_odcompleteness_completeness 99.81
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+2.0503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0870
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.005
3. Rigid bond restraints
 Cl1, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, Cl2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, Cl3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim Cl1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C1 \\sim Cl3: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Cl2 \\sim C1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
5.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C5(H5A,H5B), C10(H10A,H10B), C12(H12A,H12B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
I2 I 0.77412(3) 0.46091(4) 0.46630(3) 0.04677(14) Uani 1 1 d . . . . .
I1 I 0.83331(3) 0.43070(4) 0.93403(3) 0.04848(15) Uani 1 1 d . . . . .
Cl2 Cl 0.50035(11) 0.35363(17) 0.60676(14) 0.0675(5) Uani 1 1 d . U . . .
Cl3 Cl 0.55008(12) 0.2595(2) 0.81382(14) 0.0779(6) Uani 1 1 d . U . . .
Cl1 Cl 0.56301(15) 0.08563(17) 0.6433(2) 0.1105(9) Uani 1 1 d . U . . .
O1 O 0.7072(2) 0.4191(3) 0.7003(2) 0.0261(7) Uani 1 1 d . . . . .
C3 C 0.8102(3) 0.4804(4) 0.7011(3) 0.0225(9) Uani 1 1 d . . . . .
H3 H 0.8648 0.4128 0.6977 0.027 Uiso 1 1 calc R . . . .
C8 C 0.9162(4) 0.6380(5) 0.6087(4) 0.0371(11) Uani 1 1 d . . . . .
H8A H 0.9164 0.6957 0.5489 0.045 Uiso 1 1 calc R . . . .
H8B H 0.9692 0.5701 0.6044 0.045 Uiso 1 1 calc R . . . .
C5 C 0.7235(4) 0.6810(4) 0.6131(3) 0.0320(10) Uani 1 1 d . . . . .
H5A H 0.6546 0.6400 0.6122 0.038 Uiso 1 1 calc R . . . .
H5B H 0.7223 0.7390 0.5533 0.038 Uiso 1 1 calc R . . . .
C11 C 0.8331(3) 0.5631(4) 0.8012(3) 0.0269(10) Uani 1 1 d . . . . .
C10 C 0.9418(4) 0.6256(5) 0.8026(4) 0.0361(11) Uani 1 1 d . . . . .
H10A H 0.9947 0.5573 0.7991 0.043 Uiso 1 1 calc R . . . .
H10B H 0.9589 0.6748 0.8666 0.043 Uiso 1 1 calc R . . . .
N1 N 0.7777(3) 0.2126(4) 0.6842(4) 0.0450(11) Uani 1 1 d D . . . .
C12 C 0.7491(4) 0.6682(4) 0.8069(3) 0.0325(10) Uani 1 1 d . . . . .
H12A H 0.7634 0.7182 0.8709 0.039 Uiso 1 1 calc R . . . .
H12B H 0.6803 0.6268 0.8064 0.039 Uiso 1 1 calc R . . . .
C4 C 0.8085(3) 0.5749(4) 0.6091(3) 0.0260(9) Uani 1 1 d . . . . .
C6 C 0.7494(4) 0.7604(4) 0.7134(4) 0.0378(11) Uani 1 1 d . . . . .
H6 H 0.6957 0.8291 0.7172 0.045 Uiso 1 1 calc R . . . .
C2 C 0.7006(3) 0.2876(4) 0.6875(4) 0.0289(10) Uani 1 1 d . . . . .
C9 C 0.9415(4) 0.7181(5) 0.7095(4) 0.0380(11) Uani 1 1 d . . . . .
H9 H 1.0110 0.7598 0.7101 0.046 Uiso 1 1 calc R . . . .
C7 C 0.8569(4) 0.8250(5) 0.7140(4) 0.0429(12) Uani 1 1 d . . . . .
H7A H 0.8724 0.8773 0.7767 0.052 Uiso 1 1 calc R . . . .
H7B H 0.8568 0.8835 0.6546 0.052 Uiso 1 1 calc R . . . .
C1 C 0.5838(4) 0.2487(5) 0.6853(5) 0.0424(12) Uani 1 1 d . U . . .
H1 H 0.749(4) 0.136(2) 0.675(4) 0.051 Uiso 1 1 d DR . . . .


_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
I2 C4 2.181(4) . ?
I1 C11 2.180(4) . ?
Cl2 C1 1.746(5) . ?
Cl3 C1 1.769(6) . ?
Cl1 C1 1.747(5) . ?
O1 C3 1.451(5) . ?
O1 C2 1.341(5) . ?
C3 C11 1.541(6) . ?
C3 C4 1.526(6) . ?
C8 C4 1.515(6) . ?
C8 C9 1.539(7) . ?
C5 C4 1.530(6) . ?
C5 C6 1.531(7) . ?
C11 C10 1.521(6) . ?
C11 C12 1.517(6) . ?
C10 C9 1.526(7) . ?
N1 C2 1.246(6) . ?
C12 C6 1.529(7) . ?
C6 C7 1.518(7) . ?
C2 C1 1.537(6) . ?
C9 C7 1.533(7) . ?

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 O1 C3 117.9(3) . . ?
O1 C3 C11 108.9(3) . . ?
O1 C3 C4 109.1(3) . . ?
C4 C3 C11 107.5(3) . . ?
C4 C8 C9 108.9(4) . . ?
C4 C5 C6 108.1(4) . . ?
C3 C11 I1 108.3(3) . . ?
C10 C11 I1 109.0(3) . . ?
C10 C11 C3 108.8(4) . . ?
C12 C11 I1 109.2(3) . . ?
C12 C11 C3 110.7(3) . . ?
C12 C11 C10 110.9(4) . . ?
C11 C10 C9 108.9(4) . . ?
C11 C12 C6 108.9(4) . . ?
C3 C4 I2 108.4(3) . . ?
C3 C4 C5 111.1(3) . . ?
C8 C4 I2 108.4(3) . . ?
C8 C4 C3 109.4(4) . . ?
C8 C4 C5 110.5(4) . . ?
C5 C4 I2 109.0(3) . . ?
C12 C6 C5 109.4(4) . . ?
C7 C6 C5 109.8(4) . . ?
C7 C6 C12 110.0(4) . . ?
O1 C2 C1 107.6(4) . . ?
N1 C2 O1 124.7(4) . . ?
N1 C2 C1 127.5(4) . . ?
C10 C9 C8 109.2(4) . . ?
C10 C9 C7 109.9(4) . . ?
C7 C9 C8 108.8(4) . . ?
C6 C7 C9 109.6(4) . . ?
Cl2 C1 Cl3 108.3(3) . . ?
Cl2 C1 Cl1 109.3(3) . . ?
Cl1 C1 Cl3 107.8(3) . . ?
C2 C1 Cl2 112.4(3) . . ?
C2 C1 Cl3 107.8(4) . . ?
C2 C1 Cl1 111.1(3) . . ?

_olex2_date_sample_data_collection 1486652000.67
_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 2.389
_oxdiff_exptl_absorpt_empirical_full_min 0.601
