# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1908056'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;

#2016ncs0557y

_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C11 H12 N O2 S'
_chemical_formula_sum            'C11 H12 I N O2 S'
_chemical_formula_weight         349.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H12 N1 O2 S1 I1'
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'
S S 0.1246 0.1234 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.2803(3)
_cell_length_b                   10.7176(2)
_cell_length_c                   16.7845(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.662(2)
_cell_angle_gamma                90
_cell_volume                     2433.81(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8227
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8270
_cell_measurement_theta_min      2.3740
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.768
_exptl_absorpt_coefficient_mu    2.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method 'as supplied'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10576
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.424
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00  22.00   1.00    7.00    --  -17.00 -72.00 150.00  129
  2  ω   -104.00   1.00   1.00    7.00    --  -17.00 -18.00   0.00  105
  3  ω   -107.00  22.00   1.00    7.00    --  -17.00 -72.00-180.00  129
  4  ω   -107.00 -79.00   1.00    7.00    --  -17.00 -18.00  30.00   28
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0266384000
_diffrn_orient_matrix_UB_12      0.0062395000
_diffrn_orient_matrix_UB_13      0.0289347000
_diffrn_orient_matrix_UB_21      -0.0451164000
_diffrn_orient_matrix_UB_22      -0.0005935000
_diffrn_orient_matrix_UB_23      -0.0337875000
_diffrn_orient_matrix_UB_31      -0.0021387000
_diffrn_orient_matrix_UB_32      -0.0658922000
_diffrn_orient_matrix_UB_33      0.0029770000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2606
_reflns_number_total             2789
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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         0.538
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0168
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0221P)²+1.7343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0398
_refine_ls_wR_factor_ref         0.0405
_refine_special_details          
'Hydrogen atom positions were calculated geometrically except H2 (bound to O2) which was located from the difference map and refined using the riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
I1 I 0.66479(2) 0.84495(2) 0.61198(2) 0.01384(5) Uani 1 1 d . . . . .
S1 S 1.13619(3) 1.01728(4) 0.51348(3) 0.01291(9) Uani 1 1 d . . . . .
O1 O 0.95484(10) 0.84359(11) 0.64606(10) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.86940(9) 0.66630(12) 0.63765(10) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.8262(18) 0.709(2) 0.6353(15) 0.031 Uiso 1 1 d R . . . .
N1 N 1.13118(9) 0.80855(13) 0.58367(9) 0.0110(3) Uani 1 1 d . . . . .
C1 C 1.13912(11) 0.93081(16) 0.59923(11) 0.0126(3) Uani 1 1 d . . . . .
C2 C 1.12479(11) 0.88363(16) 0.45277(11) 0.0121(3) Uani 1 1 d . . . . .
C3 C 1.11992(12) 0.87407(17) 0.36879(11) 0.0144(3) Uani 1 1 d . . . . .
H3 H 1.118618 0.946433 0.335767 0.017 Uiso 1 1 calc R . . . .
C4 C 1.11703(11) 0.75600(17) 0.33500(11) 0.0151(3) Uani 1 1 d . . . . .
H4 H 1.112647 0.746931 0.277621 0.018 Uiso 1 1 calc R . . . .
C5 C 1.12047(12) 0.64963(15) 0.38420(12) 0.0143(4) Uani 1 1 d . . . . .
H5 H 1.120078 0.569589 0.359780 0.017 Uiso 1 1 calc R . . . .
C6 C 1.12443(12) 0.65801(15) 0.46772(12) 0.0133(3) Uani 1 1 d . . . . .
H6 H 1.126408 0.585472 0.500755 0.016 Uiso 1 1 calc R . . . .
C7 C 1.12538(10) 0.77739(16) 0.50119(11) 0.0113(3) Uani 1 1 d . . . . .
C8 C 1.15108(13) 0.98982(17) 0.68177(11) 0.0173(4) Uani 1 1 d . . . . .
H8A H 1.153501 1.080698 0.676285 0.026 Uiso 1 1 calc GR . . . .
H8B H 1.212619 0.960604 0.723029 0.026 Uiso 1 1 calc GR . . . .
H8C H 1.095043 0.967167 0.700558 0.026 Uiso 1 1 calc GR . . . .
C9 C 1.13001(11) 0.71255(16) 0.64689(11) 0.0134(3) Uani 1 1 d . . . . .
H9A H 1.148374 0.752169 0.703073 0.016 Uiso 1 1 calc R . . . .
H9B H 1.180519 0.648540 0.648364 0.016 Uiso 1 1 calc R . . . .
C10 C 1.03004(12) 0.64883(15) 0.62920(12) 0.0142(4) Uani 1 1 d . . . . .
H10A H 1.009202 0.615894 0.571039 0.017 Uiso 1 1 calc R . . . .
H10B H 1.037855 0.576844 0.667743 0.017 Uiso 1 1 calc R . . . .
C11 C 0.94923(11) 0.73197(16) 0.63901(11) 0.0128(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7011(17) . ?
S1 C2 1.7351(18) . ?
O1 C11 1.202(2) . ?
O2 H2 0.76(2) . ?
O2 C11 1.334(2) . ?
N1 C1 1.334(2) . ?
N1 C7 1.401(2) . ?
N1 C9 1.482(2) . ?
C1 C8 1.482(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.397(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.524(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.508(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
C1 S1 C2 91.11(8) . . ?
C11 O2 H2 111.1(19) . . ?
C1 N1 C7 113.72(14) . . ?
C1 N1 C9 124.17(14) . . ?
C7 N1 C9 122.11(14) . . ?
N1 C1 S1 113.08(13) . . ?
N1 C1 C8 125.40(15) . . ?
C8 C1 S1 121.51(13) . . ?
C3 C2 S1 128.32(14) . . ?
C3 C2 C7 121.18(16) . . ?
C7 C2 S1 110.43(13) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 117.91(17) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.87(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.72(15) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 121.4 . . ?
C5 C6 C7 117.25(15) . . ?
C7 C6 H6 121.4 . . ?
C2 C7 N1 111.60(15) . . ?
C6 C7 N1 127.32(16) . . ?
C6 C7 C2 121.02(16) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
N1 C9 C10 113.34(14) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.58(14) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
O1 C11 O2 123.81(15) . . ?
O1 C11 C10 124.71(15) . . ?
O2 C11 C10 111.48(15) . . ?

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
S1 C2 C3 C4 176.04(12) . . . . ?
S1 C2 C7 N1 2.24(15) . . . . ?
S1 C2 C7 C6 -175.25(12) . . . . ?
N1 C9 C10 C11 -68.0(2) . . . . ?
C1 S1 C2 C3 -178.19(15) . . . . ?
C1 S1 C2 C7 -1.01(12) . . . . ?
C1 N1 C7 C2 -2.71(18) . . . . ?
C1 N1 C7 C6 174.58(15) . . . . ?
C1 N1 C9 C10 110.95(17) . . . . ?
C2 S1 C1 N1 -0.52(12) . . . . ?
C2 S1 C1 C8 178.54(14) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C2 C7 N1 179.65(14) . . . . ?
C3 C2 C7 C6 2.2(2) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 N1 -178.58(14) . . . . ?
C5 C6 C7 C2 -1.5(2) . . . . ?
C7 N1 C1 S1 1.94(16) . . . . ?
C7 N1 C1 C8 -177.07(14) . . . . ?
C7 N1 C9 C10 -70.04(18) . . . . ?
C7 C2 C3 C4 -0.9(2) . . . . ?
C9 N1 C1 S1 -178.97(11) . . . . ?
C9 N1 C1 C8 2.0(2) . . . . ?
C9 N1 C7 C2 178.18(13) . . . . ?
C9 N1 C7 C6 -4.5(2) . . . . ?
C9 C10 C11 O1 12.2(3) . . . . ?
C9 C10 C11 O2 -168.77(15) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_original_sample_id 15CHK-05-E1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.562
_oxdiff_exptl_absorpt_empirical_full_min 0.271
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1908057'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;

#2016ncs0556y

_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O5 S, H2 O'
_chemical_formula_sum            'C17 H17 N O6 S'
_chemical_formula_weight         363.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H15 N O5 S'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4467(7)
_cell_length_b                   9.8579(7)
_cell_length_c                   10.8912(8)
_cell_angle_alpha                114.208(7)
_cell_angle_beta                 113.622(7)
_cell_angle_gamma                91.306(6)
_cell_volume                     826.02(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3270
_cell_measurement_theta_min      2.2890
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method 'as supplied'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10889
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.296
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  23.00   1.00   20.00    --  -16.00 -72.00 150.00  110
  2  ω    -23.00  74.00   1.00   20.00    --  -16.00  54.00 -90.00   97
  3  ω    -61.00  23.00   1.00   20.00    --  -16.00 -72.00 -30.00   84
  4  ω    -57.00  22.00   1.00   20.00    --  -16.00   0.00 120.00   79
  5  ω    -16.00  -1.00   1.00   20.00    --  -16.00  54.00  90.00   15
  6  ω    -30.00  74.00   1.00   20.00    --  -16.00  72.00 150.00  104
  7  ω    -69.00   2.00   1.00   20.00    --  -16.00 -72.00  30.00   71
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442875000
_diffrn_orient_matrix_UB_12      0.0263358000
_diffrn_orient_matrix_UB_13      -0.0284309000
_diffrn_orient_matrix_UB_21      -0.0712821000
_diffrn_orient_matrix_UB_22      -0.0106432000
_diffrn_orient_matrix_UB_23      -0.0630496000
_diffrn_orient_matrix_UB_31      -0.0052912000
_diffrn_orient_matrix_UB_32      0.0757970000
_diffrn_orient_matrix_UB_33      0.0400954000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2693
_reflns_number_total             3776
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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         0.528
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.024
_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)+(0.0648P)²+0.2998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1309
_refine_special_details          
'Hydrogen atom positions were calculated geometrically except H5 (bound to O5) which was located from the difference map and refined using the riding model.  The solvent water molecule was refined with rigid body restraints.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O51(H51A,H51B)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5A), C6(H6), C8(H8)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
S1 S -1.33663(8) -1.65057(7) -1.38696(7) 0.02043(17) Uani 1 1 d . . . . .
O1 O -1.0763(2) -1.39559(18) -1.29666(18) 0.0236(4) Uani 1 1 d . . . . .
O2 O -0.9393(2) -1.23353(18) -1.44512(18) 0.0220(4) Uani 1 1 d . . . . .
O3 O -1.2496(2) -1.45130(19) -1.77425(18) 0.0249(4) Uani 1 1 d . . . . .
O4 O -1.9030(2) -1.9621(2) -2.10641(19) 0.0293(4) Uani 1 1 d . . . . .
O5 O -1.7378(2) -2.1076(2) -2.1602(2) 0.0246(4) Uani 1 1 d . . . . .
H5 H -1.807(4) -2.148(3) -2.252(3) 0.037 Uiso 1 1 d R . . . .
N1 N -1.5891(2) -1.7749(2) -1.6394(2) 0.0183(4) Uani 1 1 d . . . . .
C1 C -1.4460(3) -1.6759(3) -1.5700(3) 0.0188(5) Uani 1 1 d . . . . .
C2 C -1.4889(3) -1.7737(3) -1.4065(3) 0.0189(5) Uani 1 1 d . . . . .
C3 C -1.4923(3) -1.8150(3) -1.3003(3) 0.0235(6) Uani 1 1 d . . . . .
H3 H -1.405235 -1.775855 -1.202786 0.028 Uiso 1 1 calc R . . . .
C4 C -1.6268(3) -1.9152(3) -1.3407(3) 0.0241(6) Uani 1 1 d . . . . .
H4 H -1.632549 -1.944510 -1.269606 0.029 Uiso 1 1 calc R . . . .
C5 C -1.7537(3) -1.9736(3) -1.4843(3) 0.0240(6) Uani 1 1 d . . . . .
H5A H -1.844454 -2.042302 -1.509360 0.029 Uiso 1 1 calc R . . . .
C6 C -1.7504(3) -1.9336(3) -1.5915(3) 0.0209(5) Uani 1 1 d . . . . .
H6 H -1.836864 -1.974049 -1.689435 0.025 Uiso 1 1 calc R . . . .
C7 C -1.6162(3) -1.8322(3) -1.5504(3) 0.0185(5) Uani 1 1 d . . . . .
C8 C -1.3961(3) -1.6077(3) -1.6395(3) 0.0199(5) Uani 1 1 d . . . . .
H8 H -1.463906 -1.638250 -1.742792 0.024 Uiso 1 1 calc R . . . .
C9 C -1.2570(3) -1.4997(3) -1.5730(3) 0.0202(5) Uani 1 1 d . . . . .
C10 C -1.1206(3) -1.4074(3) -1.4231(3) 0.0193(5) Uani 1 1 d . . . . .
C11 C -1.0570(3) -1.3327(3) -1.4927(3) 0.0191(5) Uani 1 1 d . . . . .
C12 C -1.1929(3) -1.4279(3) -1.6337(3) 0.0208(5) Uani 1 1 d . . . . .
C13 C -1.1546(3) -1.3641(3) -1.8069(3) 0.0284(6) Uani 1 1 d . . . . .
H13A H -1.046598 -1.383894 -1.777264 0.034 Uiso 1 1 calc R . . . .
H13B H -1.145783 -1.253389 -1.750501 0.034 Uiso 1 1 calc R . . . .
C14 C -1.2369(5) -1.4145(4) -1.9720(3) 0.0601(11) Uani 1 1 d . . . . .
H14A H -1.343489 -1.394278 -1.999772 0.090 Uiso 1 1 calc GR . . . .
H14B H -1.244709 -1.524161 -2.026410 0.090 Uiso 1 1 calc GR . . . .
H14C H -1.176646 -1.358475 -1.998442 0.090 Uiso 1 1 calc GR . . . .
C15 C -1.7038(3) -1.8211(3) -1.7967(3) 0.0196(5) Uani 1 1 d . . . . .
H15A H -1.707309 -1.731356 -1.816311 0.024 Uiso 1 1 calc R . . . .
H15B H -1.810820 -1.860141 -1.813496 0.024 Uiso 1 1 calc R . . . .
C16 C -1.6579(3) -1.9446(3) -1.9055(3) 0.0220(5) Uani 1 1 d . . . . .
H16A H -1.554832 -1.902343 -1.894191 0.026 Uiso 1 1 calc R . . . .
H16B H -1.644707 -2.030102 -1.879287 0.026 Uiso 1 1 calc R . . . .
C17 C -1.7801(3) -2.0040(3) -2.0665(3) 0.0202(5) Uani 1 1 d . . . . .
O51 O -0.8908(3) -1.2350(3) -0.9749(2) 0.0438(5) Uani 1 1 d . . . . .
H51A H -0.931949 -1.286668 -1.070286 0.066 Uiso 1 1 d G . . . .
H51B H -0.956022 -1.186113 -0.950385 0.066 Uiso 1 1 d G . . . .


_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
S1 C1 1.742(2) . ?
S1 C2 1.746(2) . ?
O1 C10 1.220(3) . ?
O2 C11 1.238(3) . ?
O3 C12 1.316(3) . ?
O3 C13 1.464(3) . ?
O4 C17 1.214(3) . ?
O5 H5 0.85(3) . ?
O5 C17 1.317(3) . ?
N1 C1 1.367(3) . ?
N1 C7 1.403(3) . ?
N1 C15 1.472(3) . ?
C1 C8 1.391(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.397(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(4) . ?
C5 H5A 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(3) . ?
C9 C10 1.482(4) . ?
C9 C12 1.410(3) . ?
C10 C11 1.511(3) . ?
C11 C12 1.439(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.487(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.525(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.502(3) . ?
O51 H51A 0.8505 . ?
O51 H51B 0.8499 . ?

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 S1 C2 91.42(12) . . ?
C12 O3 C13 116.55(19) . . ?
C17 O5 H5 114(2) . . ?
C1 N1 C7 114.7(2) . . ?
C1 N1 C15 122.59(19) . . ?
C7 N1 C15 122.7(2) . . ?
N1 C1 S1 110.88(17) . . ?
N1 C1 C8 123.6(2) . . ?
C8 C1 S1 125.52(19) . . ?
C3 C2 S1 127.9(2) . . ?
C3 C2 C7 121.1(2) . . ?
C7 C2 S1 111.01(17) . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 117.9(2) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.6(2) . . ?
C7 C6 H6 121.2 . . ?
C2 C7 N1 111.9(2) . . ?
C6 C7 N1 127.0(2) . . ?
C6 C7 C2 121.0(2) . . ?
C1 C8 H8 116.7 . . ?
C9 C8 C1 126.5(2) . . ?
C9 C8 H8 116.7 . . ?
C8 C9 C10 139.7(2) . . ?
C8 C9 C12 131.1(2) . . ?
C12 C9 C10 89.2(2) . . ?
O1 C10 C9 136.2(2) . . ?
O1 C10 C11 134.8(2) . . ?
C9 C10 C11 88.96(18) . . ?
O2 C11 C10 135.0(2) . . ?
O2 C11 C12 137.9(2) . . ?
C12 C11 C10 87.03(19) . . ?
O3 C12 C9 128.2(2) . . ?
O3 C12 C11 137.0(2) . . ?
C9 C12 C11 94.8(2) . . ?
O3 C13 H13A 110.3 . . ?
O3 C13 H13B 110.3 . . ?
O3 C13 C14 107.0(2) . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 C16 110.7(2) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 112.0(2) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
O4 C17 O5 123.7(2) . . ?
O4 C17 C16 124.5(2) . . ?
O5 C17 C16 111.8(2) . . ?
H51A O51 H51B 109.4 . . ?

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
S1 C1 C8 C9 -5.2(4) . . . . ?
S1 C2 C3 C4 179.94(19) . . . . ?
S1 C2 C7 N1 -1.0(2) . . . . ?
S1 C2 C7 C6 179.62(18) . . . . ?
O1 C10 C11 O2 -0.7(5) . . . . ?
O1 C10 C11 C12 179.4(3) . . . . ?
O2 C11 C12 O3 0.9(5) . . . . ?
O2 C11 C12 C9 -179.5(3) . . . . ?
N1 C1 C8 C9 175.9(2) . . . . ?
N1 C15 C16 C17 175.03(19) . . . . ?
C1 S1 C2 C3 -179.5(2) . . . . ?
C1 S1 C2 C7 0.99(18) . . . . ?
C1 N1 C7 C2 0.4(3) . . . . ?
C1 N1 C7 C6 179.8(2) . . . . ?
C1 N1 C15 C16 79.9(3) . . . . ?
C1 C8 C9 C10 -5.3(5) . . . . ?
C1 C8 C9 C12 177.5(2) . . . . ?
C2 S1 C1 N1 -0.75(18) . . . . ?
C2 S1 C1 C8 -179.8(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C2 C7 N1 179.5(2) . . . . ?
C3 C2 C7 C6 0.1(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 N1 -178.9(2) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C7 N1 C1 S1 0.3(2) . . . . ?
C7 N1 C1 C8 179.4(2) . . . . ?
C7 N1 C15 C16 -98.4(2) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
C8 C9 C10 O1 2.7(5) . . . . ?
C8 C9 C10 C11 -177.5(3) . . . . ?
C8 C9 C12 O3 -2.5(4) . . . . ?
C8 C9 C12 C11 177.8(3) . . . . ?
C9 C10 C11 O2 179.5(3) . . . . ?
C9 C10 C11 C12 -0.39(18) . . . . ?
C10 C9 C12 O3 179.2(2) . . . . ?
C10 C9 C12 C11 -0.42(19) . . . . ?
C10 C11 C12 O3 -179.2(3) . . . . ?
C10 C11 C12 C9 0.41(19) . . . . ?
C12 O3 C13 C14 177.2(2) . . . . ?
C12 C9 C10 O1 -179.4(3) . . . . ?
C12 C9 C10 C11 0.40(18) . . . . ?
C13 O3 C12 C9 -177.8(2) . . . . ?
C13 O3 C12 C11 1.7(4) . . . . ?
C15 N1 C1 S1 -178.01(17) . . . . ?
C15 N1 C1 C8 1.0(4) . . . . ?
C15 N1 C7 C2 178.8(2) . . . . ?
C15 N1 C7 C6 -1.9(4) . . . . ?
C15 C16 C17 O4 -1.6(3) . . . . ?
C15 C16 C17 O5 178.29(19) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id 15CK-05-E2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.775
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1908058'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;

#2016ncs0555y

_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H37 N O3'
_chemical_formula_sum            'C27 H37 N O3'
_chemical_formula_weight         423.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H40 N O3'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2092(4)
_cell_length_b                   10.9301(4)
_cell_length_c                   12.2653(5)
_cell_angle_alpha                100.390(3)
_cell_angle_beta                 99.578(4)
_cell_angle_gamma                92.170(3)
_cell_volume                     1194.49(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7175
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.1980
_cell_measurement_theta_min      2.5410
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       shard
_exptl_crystal_F_000             460
_exptl_crystal_recrystallization_method 'as supplied'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15143
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.305
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00  25.00   1.00   20.00    --   -9.00 -72.00-150.00  124
  2  ω    -87.00  25.00   1.00   20.00    --   -9.00 -72.00  30.00  112
  3  ω    -15.00  78.00   1.00   20.00    --   -9.00  72.00 120.00   93
  4  ω    -22.00  -7.00   1.00   20.00    --   -9.00  72.00 -60.00   15
  5  ω    -99.00 -37.00   1.00   20.00    --   -9.00   0.00 150.00   62
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0352613000
_diffrn_orient_matrix_UB_12      0.0081466000
_diffrn_orient_matrix_UB_13      0.0570750000
_diffrn_orient_matrix_UB_21      -0.0699130000
_diffrn_orient_matrix_UB_22      -0.0010910000
_diffrn_orient_matrix_UB_23      0.0169953000
_diffrn_orient_matrix_UB_31      0.0000165000
_diffrn_orient_matrix_UB_32      -0.0656257000
_diffrn_orient_matrix_UB_33      -0.0046003000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3949
_reflns_number_total             5441
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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         0.296
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.017
_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)+(0.0535P)²+0.2857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.18001(12) 0.20902(9) 0.42250(8) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.15060(12) -0.01783(9) 0.56760(9) 0.0251(3) Uani 1 1 d . . . . .
O3 O 0.03697(13) 0.18483(10) 0.75712(9) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.15451(13) 0.63950(11) 0.67768(10) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.14652(16) 0.19534(13) 0.52019(12) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.13002(17) 0.09332(13) 0.58003(12) 0.0193(3) Uani 1 1 d . . . . .
C3 C 0.08458(17) 0.19048(13) 0.67141(13) 0.0198(3) Uani 1 1 d . . . . .
C4 C 0.11988(16) 0.28905(13) 0.60665(12) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.19047(19) 0.09330(13) 0.34297(13) 0.0224(3) Uani 1 1 d . . . . .
H5A H 0.093284 0.045573 0.320202 0.027 Uiso 1 1 calc R . . . .
H5B H 0.262620 0.040485 0.377748 0.027 Uiso 1 1 calc R . . . .
C6 C 0.24029(18) 0.13195(14) 0.24287(12) 0.0222(3) Uani 1 1 d . . . . .
H6A H 0.246605 0.057705 0.186078 0.033 Uiso 1 1 calc GR . . . .
H6B H 0.337545 0.177345 0.266485 0.033 Uiso 1 1 calc GR . . . .
H6C H 0.169224 0.186030 0.210752 0.033 Uiso 1 1 calc GR . . . .
C7 C 0.13710(16) 0.41881(13) 0.60875(12) 0.0164(3) Uani 1 1 d . . . . .
H7 H 0.162814 0.439585 0.542135 0.020 Uiso 1 1 calc R . . . .
C8 C 0.12328(16) 0.51965(13) 0.68971(12) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.07388(16) 0.52330(13) 0.80318(12) 0.0163(3) Uani 1 1 d . . . . .
C10 C 0.08927(16) 0.66215(13) 0.85116(12) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.06649(16) 0.72651(14) 0.95385(12) 0.0189(3) Uani 1 1 d . . . . .
H11 H 0.031255 0.683729 1.006214 0.023 Uiso 1 1 calc R . . . .
C12 C 0.09625(17) 0.85582(14) 0.97934(13) 0.0215(3) Uani 1 1 d . . . . .
H12 H 0.080349 0.901675 1.049367 0.026 Uiso 1 1 calc R . . . .
C13 C 0.14891(17) 0.91757(14) 0.90286(13) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.169642 1.005373 0.921925 0.027 Uiso 1 1 calc R . . . .
C14 C 0.17213(17) 0.85380(13) 0.79862(13) 0.0196(3) Uani 1 1 d . . . . .
H14 H 0.208113 0.896075 0.746236 0.023 Uiso 1 1 calc R . . . .
C15 C 0.14024(16) 0.72592(13) 0.77517(12) 0.0163(3) Uani 1 1 d . . . . .
C16 C -0.08700(17) 0.47014(14) 0.78472(13) 0.0206(3) Uani 1 1 d . . . . .
H16A H -0.148793 0.513121 0.732618 0.031 Uiso 1 1 calc GR . . . .
H16B H -0.121904 0.482573 0.856909 0.031 Uiso 1 1 calc GR . . . .
H16C H -0.092953 0.380800 0.752850 0.031 Uiso 1 1 calc GR . . . .
C17 C 0.17834(17) 0.45624(14) 0.88020(12) 0.0198(3) Uani 1 1 d . . . . .
H17A H 0.168882 0.366562 0.849317 0.030 Uiso 1 1 calc GR . . . .
H17B H 0.152500 0.470695 0.955608 0.030 Uiso 1 1 calc GR . . . .
H17C H 0.280319 0.488633 0.884851 0.030 Uiso 1 1 calc GR . . . .
C18 C 0.20943(16) 0.67387(13) 0.58164(12) 0.0164(3) Uani 1 1 d . . . . .
H18A H 0.187231 0.760896 0.577048 0.020 Uiso 1 1 calc R . . . .
H18B H 0.157590 0.619254 0.511548 0.020 Uiso 1 1 calc R . . . .
C19 C 0.37571(16) 0.66226(14) 0.59069(12) 0.0199(3) Uani 1 1 d . . . . .
H19A H 0.428123 0.735839 0.643706 0.024 Uiso 1 1 calc R . . . .
H19B H 0.402087 0.587360 0.622492 0.024 Uiso 1 1 calc R . . . .
C20 C 0.42884(17) 0.65258(15) 0.47830(13) 0.0217(3) Uani 1 1 d . . . . .
H20A H 0.535790 0.640001 0.490644 0.026 Uiso 1 1 calc R . . . .
H20B H 0.377995 0.577549 0.426424 0.026 Uiso 1 1 calc R . . . .
C21 C 0.40407(18) 0.76439(14) 0.42088(13) 0.0225(3) Uani 1 1 d . . . . .
H21A H 0.452244 0.840508 0.472665 0.027 Uiso 1 1 calc R . . . .
H21B H 0.296923 0.775346 0.404418 0.027 Uiso 1 1 calc R . . . .
C22 C 0.46591(17) 0.74865(14) 0.31126(13) 0.0221(3) Uani 1 1 d . . . . .
H22A H 0.572820 0.736821 0.328011 0.027 Uiso 1 1 calc R . . . .
H22B H 0.417340 0.672519 0.259723 0.027 Uiso 1 1 calc R . . . .
C23 C 0.44358(19) 0.85967(15) 0.25202(14) 0.0261(4) Uani 1 1 d . . . . .
H23A H 0.471026 0.937414 0.308594 0.031 Uiso 1 1 calc R . . . .
H23B H 0.337468 0.859742 0.220262 0.031 Uiso 1 1 calc R . . . .
C24 C 0.53293(19) 0.86057(15) 0.15728(14) 0.0260(4) Uani 1 1 d . . . . .
H24A H 0.513960 0.936776 0.125622 0.031 Uiso 1 1 calc R . . . .
H24B H 0.639271 0.865243 0.189874 0.031 Uiso 1 1 calc R . . . .
C25 C 0.49878(18) 0.74770(15) 0.06183(13) 0.0234(3) Uani 1 1 d . . . . .
H25A H 0.392945 0.743498 0.027890 0.028 Uiso 1 1 calc R . . . .
H25B H 0.516783 0.671121 0.093081 0.028 Uiso 1 1 calc R . . . .
C26 C 0.59131(18) 0.75126(15) -0.02982(13) 0.0249(4) Uani 1 1 d . . . . .
H26A H 0.569112 0.825272 -0.064139 0.030 Uiso 1 1 calc R . . . .
H26B H 0.697192 0.760134 0.004710 0.030 Uiso 1 1 calc R . . . .
C27 C 0.56255(19) 0.63478(16) -0.12167(13) 0.0273(4) Uani 1 1 d . . . . .
H27A H 0.629082 0.639068 -0.175671 0.041 Uiso 1 1 calc GR . . . .
H27B H 0.459947 0.629443 -0.160663 0.041 Uiso 1 1 calc GR . . . .
H27C H 0.580117 0.560853 -0.087787 0.041 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
O1 C1 1.3180(17) . ?
O1 C5 1.4683(17) . ?
O2 C2 1.2228(18) . ?
O3 C3 1.2149(18) . ?
N1 C8 1.3697(18) . ?
N1 C15 1.4119(18) . ?
N1 C18 1.4587(17) . ?
C1 C2 1.458(2) . ?
C1 C4 1.396(2) . ?
C2 C3 1.523(2) . ?
C3 C4 1.505(2) . ?
C4 C7 1.4162(19) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.502(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C8 1.369(2) . ?
C8 C9 1.5289(19) . ?
C9 C10 1.5178(19) . ?
C9 C16 1.536(2) . ?
C9 C17 1.535(2) . ?
C10 C11 1.380(2) . ?
C10 C15 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.398(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.529(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.525(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.523(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.530(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.526(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.533(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.523(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.524(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.523(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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 O1 C5 115.92(11) . . ?
C8 N1 C15 111.27(11) . . ?
C8 N1 C18 124.76(11) . . ?
C15 N1 C18 123.71(11) . . ?
O1 C1 C2 137.11(13) . . ?
O1 C1 C4 127.29(13) . . ?
C4 C1 C2 95.55(12) . . ?
O2 C2 C1 137.70(14) . . ?
O2 C2 C3 135.94(14) . . ?
C1 C2 C3 86.25(11) . . ?
O3 C3 C2 133.73(14) . . ?
O3 C3 C4 137.74(14) . . ?
C4 C3 C2 88.51(11) . . ?
C1 C4 C3 89.19(11) . . ?
C1 C4 C7 125.41(13) . . ?
C7 C4 C3 145.32(13) . . ?
O1 C5 H5A 110.5 . . ?
O1 C5 H5B 110.5 . . ?
O1 C5 C6 106.22(12) . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7 114.3 . . ?
C8 C7 C4 131.46(13) . . ?
C8 C7 H7 114.3 . . ?
N1 C8 C9 108.58(12) . . ?
C7 C8 N1 122.19(13) . . ?
C7 C8 C9 129.23(13) . . ?
C8 C9 C16 109.95(12) . . ?
C8 C9 C17 111.49(12) . . ?
C10 C9 C8 101.63(11) . . ?
C10 C9 C16 111.72(12) . . ?
C10 C9 C17 109.27(12) . . ?
C17 C9 C16 112.31(12) . . ?
C11 C10 C9 130.44(13) . . ?
C11 C10 C15 120.05(13) . . ?
C15 C10 C9 109.45(12) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.73(14) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.33(14) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.59(14) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 121.6 . . ?
C15 C14 C13 116.82(13) . . ?
C15 C14 H14 121.6 . . ?
C10 C15 N1 108.94(12) . . ?
C14 C15 N1 128.58(13) . . ?
C14 C15 C10 122.48(13) . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.2 . . ?
N1 C18 H18B 109.2 . . ?
N1 C18 C19 111.94(12) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.53(12) . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 108.4 . . ?
C19 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 C19 115.54(13) . . ?
C21 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C20 C21 C22 111.90(12) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 C21 113.15(13) . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C22 C23 C24 114.35(13) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C23 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 C23 114.59(14) . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
C24 C25 C26 112.97(13) . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C25 C26 H26A 109.1 . . ?
C25 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C27 C26 C25 112.62(13) . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
O1 C1 C2 O2 6.7(3) . . . . ?
O1 C1 C2 C3 -177.04(19) . . . . ?
O1 C1 C4 C3 176.61(15) . . . . ?
O1 C1 C4 C7 -6.0(2) . . . . ?
O2 C2 C3 O3 -10.4(3) . . . . ?
O2 C2 C3 C4 171.26(19) . . . . ?
O3 C3 C4 C1 -172.9(2) . . . . ?
O3 C3 C4 C7 10.9(4) . . . . ?
N1 C8 C9 C10 -2.08(15) . . . . ?
N1 C8 C9 C16 116.38(13) . . . . ?
N1 C8 C9 C17 -118.39(13) . . . . ?
N1 C18 C19 C20 159.94(12) . . . . ?
C1 O1 C5 C6 -175.86(13) . . . . ?
C1 C2 C3 O3 173.19(19) . . . . ?
C1 C2 C3 C4 -5.13(11) . . . . ?
C1 C4 C7 C8 -175.76(15) . . . . ?
C2 C1 C4 C3 -5.61(12) . . . . ?
C2 C1 C4 C7 171.80(14) . . . . ?
C2 C3 C4 C1 5.35(11) . . . . ?
C2 C3 C4 C7 -170.9(2) . . . . ?
C3 C4 C7 C8 -0.3(3) . . . . ?
C4 C1 C2 O2 -170.71(19) . . . . ?
C4 C1 C2 C3 5.56(12) . . . . ?
C4 C7 C8 N1 175.59(15) . . . . ?
C4 C7 C8 C9 -4.5(3) . . . . ?
C5 O1 C1 C2 8.1(2) . . . . ?
C5 O1 C1 C4 -175.16(14) . . . . ?
C7 C8 C9 C10 178.00(15) . . . . ?
C7 C8 C9 C16 -63.54(19) . . . . ?
C7 C8 C9 C17 61.69(19) . . . . ?
C8 N1 C15 C10 -3.76(16) . . . . ?
C8 N1 C15 C14 175.02(15) . . . . ?
C8 N1 C18 C19 -80.62(17) . . . . ?
C8 C9 C10 C11 -177.41(15) . . . . ?
C8 C9 C10 C15 -0.14(15) . . . . ?
C9 C10 C11 C12 176.75(15) . . . . ?
C9 C10 C15 N1 2.26(16) . . . . ?
C9 C10 C15 C14 -176.61(14) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C10 C15 N1 179.85(13) . . . . ?
C11 C10 C15 C14 1.0(2) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 N1 -179.44(14) . . . . ?
C13 C14 C15 C10 -0.8(2) . . . . ?
C15 N1 C8 C7 -176.44(13) . . . . ?
C15 N1 C8 C9 3.63(16) . . . . ?
C15 N1 C18 C19 93.10(15) . . . . ?
C15 C10 C11 C12 -0.3(2) . . . . ?
C16 C9 C10 C11 65.4(2) . . . . ?
C16 C9 C10 C15 -117.33(13) . . . . ?
C17 C9 C10 C11 -59.5(2) . . . . ?
C17 C9 C10 C15 117.78(13) . . . . ?
C18 N1 C8 C7 -2.0(2) . . . . ?
C18 N1 C8 C9 178.03(12) . . . . ?
C18 N1 C15 C10 -178.23(13) . . . . ?
C18 N1 C15 C14 0.5(2) . . . . ?
C18 C19 C20 C21 61.73(18) . . . . ?
C19 C20 C21 C22 177.82(13) . . . . ?
C20 C21 C22 C23 -179.66(14) . . . . ?
C21 C22 C23 C24 167.13(14) . . . . ?
C22 C23 C24 C25 60.1(2) . . . . ?
C23 C24 C25 C26 -179.22(13) . . . . ?
C24 C25 C26 C27 176.86(14) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id 15CK-05-C3
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.717
_oxdiff_exptl_absorpt_empirical_full_min 0.431
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1908059'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;

#2016ncs0553x

_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C14 H18 N O2'
_chemical_formula_sum            'C14 H18 I N O2'
_chemical_formula_weight         359.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H18 I N O2'
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'
I I -0.4742 1.8119 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.3991(2)
_cell_length_b                   13.6384(4)
_cell_length_c                   29.8148(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3008.67(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9439
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5210
_cell_measurement_theta_min      2.7100
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    2.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeCN'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            25790
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.733
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_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   -107.00  73.00   1.00   10.00    --  -17.00   0.00 -90.00  180
  2  ω    -82.00  22.00   1.00   10.00    --  -17.00 -72.00 120.00  104
  3  ω    -44.00 -28.00   1.00   10.00    --  -17.00  72.00 -90.00   16
  4  ω    -56.00  37.00   1.00   10.00    --  -17.00  72.00-120.00   93
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0091441000
_diffrn_orient_matrix_UB_12      -0.0098467000
_diffrn_orient_matrix_UB_13      0.0232501000
_diffrn_orient_matrix_UB_21      0.0931894000
_diffrn_orient_matrix_UB_22      -0.0118176000
_diffrn_orient_matrix_UB_23      0.0012237000
_diffrn_orient_matrix_UB_31      0.0203857000
_diffrn_orient_matrix_UB_32      0.0496939000
_diffrn_orient_matrix_UB_33      0.0049010000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             3452
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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         0.453
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.035
_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)+(0.0223P)²+1.4682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0628
_refine_special_details          
'Hydrogen atom positions were calculated geometrically except H2 (bound to O2) which was located from the difference map and refined using the riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
I1 I 0.39517(3) 0.36116(2) 0.63578(2) 0.01976(7) Uani 1 1 d . . . . .
O1 O 0.5239(4) 0.18464(17) 0.74061(8) 0.0337(6) Uani 1 1 d . . . . .
O2 O 0.3883(4) 0.33017(17) 0.74975(8) 0.0292(6) Uani 1 1 d . . . . .
H2 H 0.390(5) 0.331(3) 0.7211(13) 0.044 Uiso 1 1 d R . . . .
N1 N 0.3450(4) 0.09201(18) 0.86633(8) 0.0167(6) Uani 1 1 d . . . . .
C1 C 0.2000(5) 0.0392(2) 0.86815(10) 0.0171(7) Uani 1 1 d . . . . .
C2 C 0.1421(4) 0.0243(2) 0.91620(10) 0.0154(7) Uani 1 1 d . . . . .
C3 C 0.2906(4) 0.0759(2) 0.94118(10) 0.0129(6) Uani 1 1 d . . . . .
C4 C 0.3217(4) 0.0895(2) 0.98636(10) 0.0170(7) Uani 1 1 d . . . . .
H4 H 0.243866 0.061242 1.008148 0.020 Uiso 1 1 calc R . . . .
C5 C 0.4699(5) 0.1458(2) 0.99924(11) 0.0217(7) Uani 1 1 d . . . . .
H5 H 0.494166 0.155525 1.030215 0.026 Uiso 1 1 calc R . . . .
C6 C 0.5825(4) 0.1878(2) 0.96742(12) 0.0219(8) Uani 1 1 d . . . . .
H6 H 0.681816 0.226669 0.977000 0.026 Uiso 1 1 calc R . . . .
C7 C 0.5533(4) 0.1743(2) 0.92213(11) 0.0191(7) Uani 1 1 d . . . . .
H7 H 0.630427 0.202637 0.900186 0.023 Uiso 1 1 calc R . . . .
C8 C 0.4077(4) 0.11809(19) 0.91047(10) 0.0156(7) Uani 1 1 d . . . . .
C9 C 0.1032(5) 0.0011(2) 0.82870(11) 0.0288(8) Uani 1 1 d . . . . .
H9A H 0.071333 0.055627 0.808799 0.043 Uiso 1 1 calc GR . . . .
H9B H -0.007078 -0.032453 0.838448 0.043 Uiso 1 1 calc GR . . . .
H9C H 0.181011 -0.045167 0.812594 0.043 Uiso 1 1 calc GR . . . .
C10 C -0.0396(5) 0.0774(2) 0.92292(11) 0.0234(8) Uani 1 1 d . . . . .
H10A H -0.071220 0.077242 0.954843 0.035 Uiso 1 1 calc GR . . . .
H10B H -0.134044 0.043624 0.905838 0.035 Uiso 1 1 calc GR . . . .
H10C H -0.029161 0.145248 0.912365 0.035 Uiso 1 1 calc GR . . . .
C11 C 0.1242(4) -0.0856(2) 0.92728(10) 0.0190(7) Uani 1 1 d . . . . .
H11A H 0.236275 -0.119538 0.919109 0.028 Uiso 1 1 calc GR . . . .
H11B H 0.023200 -0.113598 0.910302 0.028 Uiso 1 1 calc GR . . . .
H11C H 0.101865 -0.093692 0.959466 0.028 Uiso 1 1 calc GR . . . .
C12 C 0.4418(5) 0.1201(2) 0.82532(11) 0.0234(8) Uani 1 1 d . . . . .
H12A H 0.406295 0.075708 0.800563 0.028 Uiso 1 1 calc R . . . .
H12B H 0.573491 0.112801 0.830183 0.028 Uiso 1 1 calc R . . . .
C13 C 0.3999(5) 0.2260(2) 0.81214(10) 0.0214(7) Uani 1 1 d . . . . .
H13A H 0.270054 0.239610 0.817189 0.026 Uiso 1 1 calc R . . . .
H13B H 0.470912 0.271322 0.831169 0.026 Uiso 1 1 calc R . . . .
C14 C 0.4453(5) 0.2431(2) 0.76386(11) 0.0234(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.206(4) . ?
O2 H2 0.85(4) . ?
O2 C14 1.328(4) . ?
N1 C1 1.293(4) . ?
N1 C8 1.440(4) . ?
N1 C12 1.468(4) . ?
C1 C2 1.509(4) . ?
C1 C9 1.472(4) . ?
C2 C3 1.503(4) . ?
C2 C10 1.540(4) . ?
C2 C11 1.541(4) . ?
C3 C4 1.379(4) . ?
C3 C8 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.368(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.529(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.496(4) . ?

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
C14 O2 H2 109(3) . . ?
C1 N1 C8 111.5(3) . . ?
C1 N1 C12 125.8(3) . . ?
C8 N1 C12 122.7(3) . . ?
N1 C1 C2 110.5(3) . . ?
N1 C1 C9 124.5(3) . . ?
C9 C1 C2 124.9(3) . . ?
C1 C2 C10 107.9(3) . . ?
C1 C2 C11 111.0(2) . . ?
C3 C2 C1 101.5(2) . . ?
C3 C2 C10 110.7(2) . . ?
C3 C2 C11 114.4(3) . . ?
C10 C2 C11 110.8(3) . . ?
C4 C3 C2 132.0(3) . . ?
C4 C3 C8 119.1(3) . . ?
C8 C3 C2 108.9(3) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.7 . . ?
C8 C7 C6 116.5(3) . . ?
C8 C7 H7 121.7 . . ?
C3 C8 N1 107.5(3) . . ?
C7 C8 N1 128.6(3) . . ?
C7 C8 C3 123.9(3) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.4 . . ?
N1 C12 H12B 109.4 . . ?
N1 C12 C13 111.2(3) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 C12 110.4(3) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
O1 C14 O2 124.2(3) . . ?
O1 C14 C13 123.9(3) . . ?
O2 C14 C13 111.9(3) . . ?

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
N1 C1 C2 C3 -2.6(3) . . . . ?
N1 C1 C2 C10 113.8(3) . . . . ?
N1 C1 C2 C11 -124.6(3) . . . . ?
N1 C12 C13 C14 -160.8(3) . . . . ?
C1 N1 C8 C3 0.8(3) . . . . ?
C1 N1 C8 C7 -178.7(3) . . . . ?
C1 N1 C12 C13 102.0(3) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
C1 C2 C3 C8 3.1(3) . . . . ?
C2 C3 C4 C5 -177.0(3) . . . . ?
C2 C3 C8 N1 -2.5(3) . . . . ?
C2 C3 C8 C7 177.0(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C3 C8 N1 179.6(3) . . . . ?
C4 C3 C8 C7 -0.9(5) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 N1 179.9(3) . . . . ?
C6 C7 C8 C3 0.5(5) . . . . ?
C8 N1 C1 C2 1.3(3) . . . . ?
C8 N1 C1 C9 179.9(3) . . . . ?
C8 N1 C12 C13 -80.6(4) . . . . ?
C8 C3 C4 C5 0.3(4) . . . . ?
C9 C1 C2 C3 178.7(3) . . . . ?
C9 C1 C2 C10 -64.9(4) . . . . ?
C9 C1 C2 C11 56.7(4) . . . . ?
C10 C2 C3 C4 66.1(4) . . . . ?
C10 C2 C3 C8 -111.3(3) . . . . ?
C11 C2 C3 C4 -59.9(4) . . . . ?
C11 C2 C3 C8 122.7(3) . . . . ?
C12 N1 C1 C2 178.9(3) . . . . ?
C12 N1 C1 C9 -2.4(5) . . . . ?
C12 N1 C8 C3 -176.9(3) . . . . ?
C12 N1 C8 C7 3.6(5) . . . . ?
C12 C13 C14 O1 -8.3(5) . . . . ?
C12 C13 C14 O2 171.6(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id 15CK-05-G1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.106
_oxdiff_exptl_absorpt_empirical_full_min 0.325
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1908060'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;

#2017ncs0550ya

_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O5'
_chemical_formula_sum            'C20 H21 N O5'
_chemical_formula_weight         355.38
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H23 N O5'
_chemical_oxdiff_usercomment     15CK-05-62
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   12.5207(3)
_cell_length_b                   10.7016(2)
_cell_length_c                   26.8410(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3596.47(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16643
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.4510
_cell_measurement_theta_min      1.9050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_recrystallization_method 'as supplied'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            39507
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         1.903
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_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   -101.00  78.00   0.50    5.00    --  -11.80  11.00 -27.00  358
  2  ω   -101.00  25.00   0.50    5.00    --  -11.80 -65.00  90.00  252
  3  ω   -101.00  22.00   0.50    5.00    --  -11.80 -57.00   0.00  246
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0029891000
_diffrn_orient_matrix_UB_12      -0.0113817000
_diffrn_orient_matrix_UB_13      -0.0260061000
_diffrn_orient_matrix_UB_21      -0.0080677000
_diffrn_orient_matrix_UB_22      -0.0645411000
_diffrn_orient_matrix_UB_23      0.0047008000
_diffrn_orient_matrix_UB_31      -0.0559685000
_diffrn_orient_matrix_UB_32      0.0098611000
_diffrn_orient_matrix_UB_33      0.0007497000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                7642
_reflns_number_total             8244
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_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         0.457
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 3443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         8244
_refine_ls_number_restraints     1355
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      0.965
_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)+(0.0520P)²+0.5864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          
'First molecule of asymmetric unit exhibits disorder in squaraine and ethoxy moiety (approx. 50:50).  Second molecule exhibits disorder in indole, linker, squaraine, ethoxy and acid moieties (approx 82:18).  RIGU and SIMU restraints applied throughout'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H52B-O1
 2.031 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O5B)=Sof(C18B)=Sof(C19B)=Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(O5A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(C20A)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=FVAR(1)
 Sof(O51B)=Sof(O52B)=Sof(H52B)=Sof(O55B)=Sof(N51B)=Sof(C58B)=Sof(C59B)=
 Sof(H59C)=Sof(H59D)=Sof(C60B)=Sof(H60C)=Sof(H60D)=Sof(C61B)=Sof(C64B)=
 Sof(H64B)=Sof(C65B)=Sof(C68B)=Sof(C69B)=Sof(H69C)=Sof(H69D)=Sof(C70B)=
 Sof(H70D)=Sof(H70E)=Sof(H70F)=1-FVAR(2)
 Sof(O51A)=Sof(O52A)=Sof(H52A)=Sof(O55A)=Sof(N51A)=Sof(C58A)=Sof(C59A)=
 Sof(H59A)=Sof(H59B)=Sof(C60A)=Sof(H60A)=Sof(H60B)=Sof(C61A)=Sof(C64A)=
 Sof(H64A)=Sof(C65A)=Sof(C68A)=Sof(C69A)=Sof(H69A)=Sof(H69B)=Sof(C70A)=
 Sof(H70A)=Sof(H70B)=Sof(H70C)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C19A(H19A,H19B), C19B(H19C,H19D), C59A(H59A,
 H59B), C59B(H59C,H59D), C60A(H60A,H60B), C60B(H60C,H60D), C69A(H69A,H69B),
 C69B(H69C,H69D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C14(H14), C52(H52), C53(H53), C54(H54),
 C55(H55), C64A(H64A), C64B(H64B)
6.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20A(H20A,H20B,H20C), C20B(H20D,
 H20E,H20F), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C70A(H70A,H70B,H70C),
 C70B(H70D,H70E,H70F)
6.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O52A(H52A), O52B(H52B)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.27222(13) 0.66166(17) 0.48125(6) 0.0315(4) Uani 1 1 d D U . . .
O2 O 0.40369(13) 0.63773(19) 0.42707(6) 0.0371(4) Uani 1 1 d . U . . .
H2 H 0.437752 0.623012 0.452494 0.056 Uiso 1 1 calc GR . . . .
O3 O 0.02117(17) 1.26425(15) 0.32619(6) 0.0391(4) Uani 1 1 d . U . . .
O4 O 0.17211(16) 1.43171(15) 0.39845(8) 0.0430(5) Uani 1 1 d . U . . .
O5A O 0.2803(3) 1.1709(3) 0.43591(14) 0.0309(12) Uani 0.504(7) 1 d . U P A 1
O5B O 0.2250(3) 1.1698(3) 0.46444(14) 0.0288(12) Uani 0.496(7) 1 d . U P A 2
N1 N 0.05995(13) 0.78726(15) 0.37316(6) 0.0191(3) Uani 1 1 d . U . . .
C1 C -0.00974(15) 0.71814(18) 0.34228(7) 0.0177(4) Uani 1 1 d . U . . .
C2 C -0.02909(16) 0.59118(19) 0.34268(8) 0.0213(4) Uani 1 1 d . U . . .
H2A H 0.007825 0.537468 0.363780 0.026 Uiso 1 1 calc R . . . .
C3 C -0.10667(17) 0.5477(2) 0.30987(8) 0.0250(4) Uani 1 1 d . U . . .
H3 H -0.123247 0.463021 0.309508 0.030 Uiso 1 1 calc R . . . .
C4 C -0.15947(18) 0.6272(2) 0.27795(9) 0.0305(5) Uani 1 1 d . U . . .
H4 H -0.210928 0.595272 0.256434 0.037 Uiso 1 1 calc R . . . .
C5 C -0.13690(17) 0.7549(2) 0.27739(9) 0.0289(5) Uani 1 1 d . U . . .
H5 H -0.171802 0.808201 0.255379 0.035 Uiso 1 1 calc R . . . .
C6 C -0.06156(16) 0.80034(19) 0.31028(8) 0.0204(4) Uani 1 1 d . U . . .
C7 C -0.02347(15) 0.93228(18) 0.32014(7) 0.0193(4) Uani 1 1 d . U . . .
C8 C 0.05660(15) 0.91188(18) 0.36239(7) 0.0184(4) Uani 1 1 d . U . . .
C9 C 0.12351(16) 0.73035(18) 0.41239(7) 0.0189(4) Uani 1 1 d . U . . .
H9A H 0.090588 0.652209 0.422363 0.023 Uiso 1 1 calc R . . . .
H9B H 0.124326 0.785249 0.441147 0.023 Uiso 1 1 calc R . . . .
C10 C 0.23777(16) 0.70536(18) 0.39587(7) 0.0185(4) Uani 1 1 d . U . . .
H10A H 0.237932 0.640647 0.370569 0.022 Uiso 1 1 calc R . . . .
H10B H 0.267396 0.780652 0.381245 0.022 Uiso 1 1 calc R . . . .
C11 C 0.30605(16) 0.66514(18) 0.43872(8) 0.0195(4) Uani 1 1 d . U . . .
C12 C -0.11725(18) 1.0131(2) 0.33807(9) 0.0291(5) Uani 1 1 d . U . . .
H12A H -0.145623 0.978877 0.368365 0.044 Uiso 1 1 calc GR . . . .
H12B H -0.171990 1.014214 0.313035 0.044 Uiso 1 1 calc GR . . . .
H12C H -0.092743 1.096798 0.344028 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.0304(2) 0.9894(2) 0.27417(8) 0.0286(5) Uani 1 1 d . U . . .
H13A H 0.052153 1.073388 0.281501 0.043 Uiso 1 1 calc GR . . . .
H13B H -0.019145 0.989993 0.246866 0.043 Uiso 1 1 calc GR . . . .
H13C H 0.091812 0.940464 0.265368 0.043 Uiso 1 1 calc GR . . . .
C14 C 0.11771(18) 0.9967(2) 0.38784(9) 0.0256(4) Uani 1 1 d . U . . .
H14 H 0.162691 0.961160 0.411503 0.031 Uiso 1 1 calc R . . . .
C15 C 0.12491(18) 1.1276(2) 0.38476(9) 0.0282(5) Uani 1 1 d . U . . .
C16 C 0.08411(19) 1.2416(2) 0.35855(8) 0.0256(4) Uani 1 1 d . U . . .
C17 C 0.1552(2) 1.3212(2) 0.39200(11) 0.0363(6) Uani 1 1 d . U . . .
C18A C 0.2024(5) 1.2062(5) 0.4054(2) 0.0219(12) Uani 0.504(7) 1 d . U P A 1
C18B C 0.1741(5) 1.2021(5) 0.4231(3) 0.0222(12) Uani 0.496(7) 1 d . U P A 2
C19A C 0.3420(6) 1.2709(7) 0.4589(2) 0.0415(16) Uani 0.504(7) 1 d . U P A 1
H19A H 0.410656 1.238852 0.469741 0.050 Uiso 0.504(7) 1 calc R . P A 1
H19B H 0.354533 1.336819 0.434857 0.050 Uiso 0.504(7) 1 calc R . P A 1
C19B C 0.2746(6) 1.2697(6) 0.4915(3) 0.0344(15) Uani 0.496(7) 1 d . U P A 2
H19C H 0.283168 1.245626 0.526128 0.041 Uiso 0.496(7) 1 calc R . P A 2
H19D H 0.229362 1.343203 0.490333 0.041 Uiso 0.496(7) 1 calc R . P A 2
C20A C 0.2847(6) 1.3201(8) 0.5010(3) 0.0430(16) Uani 0.504(7) 1 d . U P A 1
H20A H 0.220136 1.359396 0.489685 0.065 Uiso 0.504(7) 1 calc GR . P A 1
H20B H 0.328309 1.380375 0.517882 0.065 Uiso 0.504(7) 1 calc GR . P A 1
H20C H 0.267233 1.253251 0.523413 0.065 Uiso 0.504(7) 1 calc GR . P A 1
C20B C 0.3805(6) 1.2993(6) 0.4697(3) 0.0405(15) Uani 0.496(7) 1 d . U P A 2
H20D H 0.371707 1.324969 0.435692 0.061 Uiso 0.496(7) 1 calc GR . P A 2
H20E H 0.425239 1.226536 0.471011 0.061 Uiso 0.496(7) 1 calc GR . P A 2
H20F H 0.413170 1.365704 0.488355 0.061 Uiso 0.496(7) 1 calc GR . P A 2
O51A O 0.5111(2) 0.5697(3) 0.50892(12) 0.0291(7) Uani 0.819(4) 1 d . U P B 1
O51B O 0.5501(8) 0.6117(11) 0.4878(4) 0.035(3) Uani 0.181(4) 1 d . U P B 2
O52A O 0.3779(2) 0.6102(2) 0.56152(8) 0.0296(5) Uani 0.819(4) 1 d . U P B 1
H52A H 0.347436 0.630794 0.535759 0.044 Uiso 0.819(4) 1 calc GR . P B 1
O52B O 0.4303(13) 0.5749(14) 0.5486(6) 0.023(3) Uani 0.181(4) 1 d . U P B 2
H52B H 0.387151 0.589894 0.526366 0.034 Uiso 0.181(4) 1 calc DGR . P B 2
O53 O 0.71760(16) -0.04310(15) 0.67502(7) 0.0374(4) Uani 1 1 d . U . . .
O54 O 0.60093(14) -0.20758(14) 0.58959(7) 0.0340(4) Uani 1 1 d . U . . .
O55A O 0.53774(18) 0.05603(18) 0.53094(8) 0.0301(5) Uani 0.819(4) 1 d . U P B 1
O55B O 0.4742(8) 0.0555(9) 0.5635(4) 0.036(3) Uani 0.181(4) 1 d . U P B 2
N51A N 0.7028(2) 0.4343(2) 0.62520(10) 0.0206(5) Uani 0.819(4) 1 d . U P B 1
N51B N 0.6653(10) 0.4395(10) 0.6439(5) 0.019(2) Uani 0.181(4) 1 d . U P B 2
C51 C 0.77047(19) 0.5022(2) 0.65745(8) 0.0272(5) Uani 1 1 d . U . . .
C52 C 0.7912(2) 0.6293(2) 0.65771(9) 0.0292(5) Uani 1 1 d . U . . .
H52 H 0.754755 0.683949 0.636833 0.035 Uiso 1 1 calc R . . . .
C53 C 0.86870(18) 0.6711(2) 0.69046(8) 0.0261(4) Uani 1 1 d . U . . .
H53 H 0.885092 0.755858 0.691557 0.031 Uiso 1 1 calc R . . . .
C54 C 0.92215(17) 0.5895(2) 0.72154(8) 0.0249(4) Uani 1 1 d . U . . .
H54 H 0.974504 0.619854 0.742936 0.030 Uiso 1 1 calc R . . . .
C55 C 0.89854(16) 0.4619(2) 0.72125(8) 0.0216(4) Uani 1 1 d . U . . .
H55 H 0.934378 0.407069 0.742314 0.026 Uiso 1 1 calc R . . . .
C56 C 0.82099(16) 0.41893(19) 0.68906(7) 0.0200(4) Uani 1 1 d . U . . .
C57 C 0.77937(16) 0.28790(19) 0.68003(8) 0.0211(4) Uani 1 1 d . U . . .
C58A C 0.7046(4) 0.3097(5) 0.63440(14) 0.0218(9) Uani 0.819(4) 1 d . U P B 1
C58B C 0.689(2) 0.309(2) 0.6500(6) 0.020(4) Uani 0.181(4) 1 d . U P B 2
C59A C 0.6478(2) 0.4923(2) 0.58361(10) 0.0196(5) Uani 0.819(4) 1 d . U P B 1
H59A H 0.651937 0.437607 0.554848 0.024 Uiso 0.819(4) 1 calc R . P B 1
H59B H 0.683324 0.570038 0.575174 0.024 Uiso 0.819(4) 1 calc R . P B 1
C59B C 0.5806(10) 0.4987(10) 0.6161(5) 0.021(2) Uani 0.181(4) 1 d . U P B 2
H59C H 0.565254 0.579793 0.630510 0.025 Uiso 0.181(4) 1 calc R . P B 2
H59D H 0.516377 0.448236 0.618372 0.025 Uiso 0.181(4) 1 calc R . P B 2
C60A C 0.5318(2) 0.5185(2) 0.59542(9) 0.0206(6) Uani 0.819(4) 1 d . U P B 1
H60A H 0.497388 0.442008 0.606272 0.025 Uiso 0.819(4) 1 calc R . P B 1
H60B H 0.527506 0.578468 0.622461 0.025 Uiso 0.819(4) 1 calc R . P B 1
C60B C 0.6108(11) 0.5150(12) 0.5614(6) 0.026(3) Uani 0.181(4) 1 d . U P B 2
H60C H 0.675309 0.564979 0.559512 0.031 Uiso 0.181(4) 1 calc R . P B 2
H60D H 0.626871 0.433554 0.547434 0.031 Uiso 0.181(4) 1 calc R . P B 2
C61A C 0.4743(4) 0.5692(4) 0.55088(17) 0.0193(8) Uani 0.819(4) 1 d . U P B 1
C61B C 0.5264(15) 0.5756(14) 0.5303(8) 0.021(3) Uani 0.181(4) 1 d . U P B 2
C62 C 0.72034(19) 0.2394(2) 0.72612(9) 0.0300(5) Uani 1 1 d . U . . .
H62A H 0.768349 0.237835 0.753999 0.045 Uiso 1 1 calc GR . . . .
H62B H 0.694451 0.156465 0.719787 0.045 Uiso 1 1 calc GR . . . .
H62C H 0.661230 0.293483 0.733452 0.045 Uiso 1 1 calc GR . . . .
C63 C 0.87146(18) 0.2017(2) 0.66472(8) 0.0243(4) Uani 1 1 d . U . . .
H63A H 0.901493 0.230457 0.633867 0.036 Uiso 1 1 calc GR . . . .
H63B H 0.845115 0.118123 0.660582 0.036 Uiso 1 1 calc GR . . . .
H63C H 0.925451 0.202622 0.690109 0.036 Uiso 1 1 calc GR . . . .
C64A C 0.6479(3) 0.2272(3) 0.60598(14) 0.0233(7) Uani 0.819(4) 1 d . U P B 1
H64A H 0.606399 0.264918 0.581482 0.028 Uiso 0.819(4) 1 calc R . P B 1
C64B C 0.6185(14) 0.2297(14) 0.6247(6) 0.020(3) Uani 0.181(4) 1 d . U P B 2
H64B H 0.564366 0.269373 0.607100 0.024 Uiso 0.181(4) 1 calc R . P B 2
C65A C 0.6404(4) 0.0969(4) 0.60672(16) 0.0234(9) Uani 0.819(4) 1 d . U P B 1
C65B C 0.6178(16) 0.0919(19) 0.6219(7) 0.017(3) Uani 0.181(4) 1 d . U P B 2
C66 C 0.66863(19) -0.0185(2) 0.63748(9) 0.0274(5) Uani 1 1 d . U . . .
C67 C 0.61272(18) -0.0965(2) 0.59782(10) 0.0303(5) Uani 1 1 d . U . . .
C68A C 0.5882(3) 0.0214(3) 0.57188(12) 0.0234(6) Uani 0.819(4) 1 d . U P B 1
C68B C 0.5540(12) 0.0193(13) 0.5929(6) 0.026(3) Uani 0.181(4) 1 d . U P B 2
C69A C 0.4753(4) -0.0418(4) 0.50630(17) 0.0344(9) Uani 0.819(4) 1 d . U P B 1
H69A H 0.513016 -0.120768 0.508518 0.041 Uiso 0.819(4) 1 calc R . P B 1
H69B H 0.466615 -0.021300 0.471328 0.041 Uiso 0.819(4) 1 calc R . P B 1
C69B C 0.4250(17) -0.0469(16) 0.5344(7) 0.037(4) Uani 0.181(4) 1 d . U P B 2
H69C H 0.413941 -0.118791 0.555764 0.044 Uiso 0.181(4) 1 calc R . P B 2
H69D H 0.355947 -0.020138 0.521949 0.044 Uiso 0.181(4) 1 calc R . P B 2
C70A C 0.3681(4) -0.0539(4) 0.53024(15) 0.0421(9) Uani 0.819(4) 1 d . U P B 1
H70A H 0.327014 -0.116010 0.512924 0.063 Uiso 0.819(4) 1 calc GR . P B 1
H70B H 0.331615 0.024880 0.528774 0.063 Uiso 0.819(4) 1 calc GR . P B 1
H70C H 0.376734 -0.078504 0.564400 0.063 Uiso 0.819(4) 1 calc GR . P B 1
C70B C 0.4935(18) -0.0823(19) 0.4924(8) 0.042(4) Uani 0.181(4) 1 d . U P B 2
H70D H 0.504227 -0.011197 0.471169 0.062 Uiso 0.181(4) 1 calc GR . P B 2
H70E H 0.459919 -0.148050 0.473779 0.062 Uiso 0.181(4) 1 calc GR . P B 2
H70F H 0.561193 -0.110817 0.504748 0.062 Uiso 0.181(4) 1 calc GR . P B 2


_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
O1 C11 1.218(3) . ?
O2 H2 0.8200 . ?
O2 C11 1.296(3) . ?
O3 C16 1.197(3) . ?
O4 C17 1.213(3) . ?
O5A C18A 1.328(7) . ?
O5A C19A 1.457(7) . ?
O5B C18B 1.326(7) . ?
O5B C19B 1.434(7) . ?
N1 C1 1.413(2) . ?
N1 C8 1.365(2) . ?
N1 C9 1.454(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.390(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 C7 1.514(3) . ?
C7 C8 1.529(3) . ?
C7 C12 1.536(3) . ?
C7 C13 1.533(3) . ?
C8 C14 1.369(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.521(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.496(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.406(3) . ?
C15 C16 1.498(3) . ?
C15 C18A 1.399(6) . ?
C15 C18B 1.440(6) . ?
C16 C17 1.525(3) . ?
C17 C18A 1.412(6) . ?
C17 C18B 1.543(6) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A C20A 1.437(10) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C19B C20B 1.484(10) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
O51A C61A 1.217(5) . ?
O51B C61B 1.24(2) . ?
O52A H52A 0.8200 . ?
O52A C61A 1.315(5) . ?
O52B H52B 0.8200 . ?
O52B C61B 1.30(2) . ?
O53 C66 1.208(3) . ?
O54 C67 1.218(3) . ?
O55A C68A 1.321(4) . ?
O55A C69A 1.464(4) . ?
O55B C68B 1.330(17) . ?
O55B C69B 1.48(2) . ?
N51A C51 1.413(3) . ?
N51A C58A 1.356(6) . ?
N51A C59A 1.451(4) . ?
N51B C51 1.523(12) . ?
N51B C58B 1.43(2) . ?
N51B C59B 1.443(18) . ?
C51 C52 1.384(3) . ?
C51 C56 1.383(3) . ?
C52 H52 0.9300 . ?
C52 C53 1.384(3) . ?
C53 H53 0.9300 . ?
C53 C54 1.381(3) . ?
C54 H54 0.9300 . ?
C54 C55 1.398(3) . ?
C55 H55 0.9300 . ?
C55 C56 1.379(3) . ?
C56 C57 1.515(3) . ?
C57 C58A 1.559(4) . ?
C57 C58B 1.41(2) . ?
C57 C62 1.532(3) . ?
C57 C63 1.533(3) . ?
C58A C64A 1.366(6) . ?
C58B C64B 1.40(3) . ?
C59A H59A 0.9700 . ?
C59A H59B 0.9700 . ?
C59A C60A 1.514(4) . ?
C59B H59C 0.9700 . ?
C59B H59D 0.9700 . ?
C59B C60B 1.53(2) . ?
C60A H60A 0.9700 . ?
C60A H60B 0.9700 . ?
C60A C61A 1.497(5) . ?
C60B H60C 0.9700 . ?
C60B H60D 0.9700 . ?
C60B C61B 1.50(2) . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?
C64A H64A 0.9300 . ?
C64A C65A 1.398(6) . ?
C64B H64B 0.9300 . ?
C64B C65B 1.48(2) . ?
C65A C66 1.527(5) . ?
C65A C68A 1.398(6) . ?
C65B C66 1.41(2) . ?
C65B C68B 1.36(2) . ?
C66 C67 1.523(3) . ?
C67 C68A 1.474(4) . ?
C67 C68B 1.448(14) . ?
C69A H69A 0.9700 . ?
C69A H69B 0.9700 . ?
C69A C70A 1.494(6) . ?
C69B H69C 0.9700 . ?
C69B H69D 0.9700 . ?
C69B C70B 1.47(3) . ?
C70A H70A 0.9600 . ?
C70A H70B 0.9600 . ?
C70A H70C 0.9600 . ?
C70B H70D 0.9600 . ?
C70B H70E 0.9600 . ?
C70B H70F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 H2 109.5 . . ?
C18A O5A C19A 116.2(5) . . ?
C18B O5B C19B 116.0(4) . . ?
C1 N1 C9 122.94(16) . . ?
C8 N1 C1 111.61(16) . . ?
C8 N1 C9 125.41(16) . . ?
C2 C1 N1 128.27(18) . . ?
C2 C1 C6 123.08(18) . . ?
C6 C1 N1 108.63(17) . . ?
C1 C2 H2A 121.7 . . ?
C1 C2 C3 116.54(19) . . ?
C3 C2 H2A 121.7 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 109.58(17) . . ?
C5 C6 C1 119.44(19) . . ?
C5 C6 C7 130.96(19) . . ?
C6 C7 C8 101.72(15) . . ?
C6 C7 C12 109.84(17) . . ?
C6 C7 C13 111.69(17) . . ?
C8 C7 C12 110.44(16) . . ?
C8 C7 C13 111.43(17) . . ?
C13 C7 C12 111.34(17) . . ?
N1 C8 C7 108.45(16) . . ?
N1 C8 C14 121.63(18) . . ?
C14 C8 C7 129.91(18) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
N1 C9 C10 112.17(16) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.33(16) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
O1 C11 O2 123.19(19) . . ?
O1 C11 C10 122.04(19) . . ?
O2 C11 C10 114.75(18) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14 114.1 . . ?
C8 C14 C15 131.8(2) . . ?
C15 C14 H14 114.1 . . ?
C14 C15 C16 144.8(2) . . ?
C14 C15 C18B 122.5(3) . . ?
C18A C15 C14 128.4(3) . . ?
C18A C15 C16 86.1(3) . . ?
C18B C15 C16 91.8(3) . . ?
O3 C16 C15 136.9(2) . . ?
O3 C16 C17 134.3(2) . . ?
C15 C16 C17 88.83(18) . . ?
O4 C17 C16 136.9(2) . . ?
O4 C17 C18A 137.7(3) . . ?
O4 C17 C18B 134.6(3) . . ?
C16 C17 C18B 86.9(3) . . ?
C18A C17 C16 84.7(3) . . ?
O5A C18A C15 125.6(5) . . ?
O5A C18A C17 135.5(5) . . ?
C15 C18A C17 97.6(4) . . ?
O5B C18B C15 131.3(4) . . ?
O5B C18B C17 137.9(5) . . ?
C15 C18B C17 90.3(4) . . ?
O5A C19A H19A 109.7 . . ?
O5A C19A H19B 109.7 . . ?
H19A C19A H19B 108.2 . . ?
C20A C19A O5A 109.7(6) . . ?
C20A C19A H19A 109.7 . . ?
C20A C19A H19B 109.7 . . ?
O5B C19B H19C 109.6 . . ?
O5B C19B H19D 109.6 . . ?
O5B C19B C20B 110.3(6) . . ?
H19C C19B H19D 108.1 . . ?
C20B C19B H19C 109.6 . . ?
C20B C19B H19D 109.6 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C61A O52A H52A 109.5 . . ?
C61B O52B H52B 109.5 . . ?
C68A O55A C69A 115.5(2) . . ?
C68B O55B C69B 114.2(11) . . ?
C51 N51A C59A 122.4(2) . . ?
C58A N51A C51 112.6(3) . . ?
C58A N51A C59A 124.6(3) . . ?
C58B N51B C51 102.9(12) . . ?
C58B N51B C59B 129.6(13) . . ?
C59B N51B C51 124.5(9) . . ?
C52 C51 N51A 128.4(2) . . ?
C52 C51 N51B 126.6(4) . . ?
C56 C51 N51A 108.57(19) . . ?
C56 C51 N51B 105.0(4) . . ?
C56 C51 C52 123.0(2) . . ?
C51 C52 H52 121.5 . . ?
C53 C52 C51 116.9(2) . . ?
C53 C52 H52 121.5 . . ?
C52 C53 H53 119.4 . . ?
C54 C53 C52 121.2(2) . . ?
C54 C53 H53 119.4 . . ?
C53 C54 H54 119.6 . . ?
C53 C54 C55 120.82(19) . . ?
C55 C54 H54 119.6 . . ?
C54 C55 H55 120.7 . . ?
C56 C55 C54 118.57(19) . . ?
C56 C55 H55 120.7 . . ?
C51 C56 C57 109.94(18) . . ?
C55 C56 C51 119.4(2) . . ?
C55 C56 C57 130.60(19) . . ?
C56 C57 C58A 101.2(2) . . ?
C56 C57 C62 110.51(17) . . ?
C56 C57 C63 109.94(17) . . ?
C58B C57 C56 102.5(9) . . ?
C58B C57 C62 97.4(8) . . ?
C58B C57 C63 123.4(8) . . ?
C62 C57 C58A 113.3(2) . . ?
C62 C57 C63 112.07(17) . . ?
C63 C57 C58A 109.3(2) . . ?
N51A C58A C57 107.5(4) . . ?
N51A C58A C64A 121.7(3) . . ?
C64A C58A C57 130.9(4) . . ?
C57 C58B N51B 113.0(16) . . ?
C64B C58B N51B 114.0(18) . . ?
C64B C58B C57 133.0(18) . . ?
N51A C59A H59A 109.2 . . ?
N51A C59A H59B 109.2 . . ?
N51A C59A C60A 111.9(2) . . ?
H59A C59A H59B 107.9 . . ?
C60A C59A H59A 109.2 . . ?
C60A C59A H59B 109.2 . . ?
N51B C59B H59C 109.3 . . ?
N51B C59B H59D 109.3 . . ?
N51B C59B C60B 111.4(11) . . ?
H59C C59B H59D 108.0 . . ?
C60B C59B H59C 109.3 . . ?
C60B C59B H59D 109.3 . . ?
C59A C60A H60A 109.4 . . ?
C59A C60A H60B 109.4 . . ?
H60A C60A H60B 108.0 . . ?
C61A C60A C59A 111.2(3) . . ?
C61A C60A H60A 109.4 . . ?
C61A C60A H60B 109.4 . . ?
C59B C60B H60C 108.7 . . ?
C59B C60B H60D 108.7 . . ?
H60C C60B H60D 107.6 . . ?
C61B C60B C59B 114.3(13) . . ?
C61B C60B H60C 108.7 . . ?
C61B C60B H60D 108.7 . . ?
O51A C61A O52A 123.2(4) . . ?
O51A C61A C60A 123.9(5) . . ?
O52A C61A C60A 112.9(4) . . ?
O51B C61B O52B 124.8(15) . . ?
O51B C61B C60B 118.7(17) . . ?
O52B C61B C60B 116.1(17) . . ?
C57 C62 H62A 109.5 . . ?
C57 C62 H62B 109.5 . . ?
C57 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C57 C63 H63A 109.5 . . ?
C57 C63 H63B 109.5 . . ?
C57 C63 H63C 109.5 . . ?
H63A C63 H63B 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C58A C64A H64A 113.9 . . ?
C58A C64A C65A 132.2(4) . . ?
C65A C64A H64A 113.9 . . ?
C58B C64B H64B 115.2 . . ?
C58B C64B C65B 129.6(16) . . ?
C65B C64B H64B 115.2 . . ?
C64A C65A C66 143.1(4) . . ?
C68A C65A C64A 126.7(4) . . ?
C68A C65A C66 90.2(3) . . ?
C66 C65B C64B 145.3(17) . . ?
C68B C65B C64B 127.1(17) . . ?
C68B C65B C66 87.5(13) . . ?
O53 C66 C65A 138.1(3) . . ?
O53 C66 C65B 131.3(9) . . ?
O53 C66 C67 134.1(2) . . ?
C65B C66 C67 92.6(9) . . ?
C67 C66 C65A 87.7(2) . . ?
O54 C67 C66 135.8(2) . . ?
O54 C67 C68A 136.5(2) . . ?
O54 C67 C68B 139.3(6) . . ?
C68A C67 C66 87.50(19) . . ?
C68B C67 C66 80.1(6) . . ?
O55A C68A C65A 128.2(3) . . ?
O55A C68A C67 137.1(3) . . ?
C65A C68A C67 94.7(3) . . ?
O55B C68B C65B 128.0(15) . . ?
O55B C68B C67 133.2(12) . . ?
C65B C68B C67 97.9(12) . . ?
O55A C69A H69A 109.6 . . ?
O55A C69A H69B 109.6 . . ?
O55A C69A C70A 110.3(4) . . ?
H69A C69A H69B 108.1 . . ?
C70A C69A H69A 109.6 . . ?
C70A C69A H69B 109.6 . . ?
O55B C69B H69C 109.5 . . ?
O55B C69B H69D 109.5 . . ?
H69C C69B H69D 108.1 . . ?
C70B C69B O55B 110.7(17) . . ?
C70B C69B H69C 109.5 . . ?
C70B C69B H69D 109.5 . . ?
C69A C70A H70A 109.5 . . ?
C69A C70A H70B 109.5 . . ?
C69A C70A H70C 109.5 . . ?
H70A C70A H70B 109.5 . . ?
H70A C70A H70C 109.5 . . ?
H70B C70A H70C 109.5 . . ?
C69B C70B H70D 109.5 . . ?
C69B C70B H70E 109.5 . . ?
C69B C70B H70F 109.5 . . ?
H70D C70B H70E 109.5 . . ?
H70D C70B H70F 109.5 . . ?
H70E C70B H70F 109.5 . . ?

_olex2_date_sample_data_collection 2017-08-23
_olex2_date_sample_submission    2017-08-18
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id 15CK-05-62
_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 2.216
_oxdiff_exptl_absorpt_empirical_full_min 0.722
