# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mn2001
_database_code_depnum_ccdc_archive 'CCDC 1983169'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_audit_creation_date             2020-02-10
_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         'C22 H16 F6 N2 O2'
_chemical_formula_sum            'C22 H16 F6 N2 O2'
_chemical_formula_weight         454.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H16 F6 N2 O2'
_chemical_oxdiff_usercomment     'Katie Lamb KL CF3 col NMR'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   28.1272(4)
_cell_length_b                   9.04947(13)
_cell_length_c                   14.7304(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3749.43(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3984
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.8870
_cell_measurement_theta_min      5.9310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 1 0.0622
0 0 1 0.1101
0 0 -1 0.0649
-1 0 1 0.0975
1 0 -1 0.0433
2 -1 2 0.0870
-2 1 -2 0.0652
0 -1 2 0.1004
-1 0 0 0.0961
1 0 0 0.0726
2 1 -1 0.1178
-1 -2 2 0.1014
0 -1 1 0.0900
2 0 1 0.0892
-2 0 -1 0.1115
1 -1 0 0.0871
-2 -1 2 0.1070
-2 -2 -1 0.1164
2 -1 1 0.0809
2 -1 0 0.0834

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.141
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9996 1.0000 0.9995 0.1190 0.1812 -0.0701
0.0002 -0.0001 0.9998 0.0340 0.0664 0.0733
-0.0002 0.0001 -0.9998 -0.0340 -0.0664 -0.0733
-0.9998 -0.0000 0.9998 0.0074 0.1073 0.0485
0.9998 0.0000 -0.9998 -0.0074 -0.1073 -0.0485
2.0001 -1.0002 2.0001 -0.0170 0.0179 0.2899
-2.0001 1.0002 -2.0001 0.0170 -0.0179 -0.2899
0.0001 -1.0001 2.0000 -0.0702 0.0999 0.2404
-1.0000 0.0000 -0.0000 -0.0266 0.0410 -0.0248
1.0000 -0.0000 0.0000 0.0266 -0.0410 0.0248
2.0001 1.0000 -1.0002 0.1574 -0.1155 -0.1175
-1.0001 -2.0000 2.0004 -0.2350 0.1080 0.3094
-0.0001 -1.0000 1.0002 -0.1042 0.0335 0.1671
2.0002 -0.0001 0.9999 0.0872 -0.0156 0.1228
-2.0002 0.0001 -0.9999 -0.0872 0.0156 -0.1228
0.9998 -1.0000 0.0004 -0.1116 -0.0738 0.1186
-1.9999 -1.0000 2.0000 -0.1234 0.1818 0.1908
-2.0006 -1.9998 -0.9992 -0.3636 -0.0501 0.0648
1.9999 -1.0001 1.0002 -0.0510 -0.0485 0.2167
1.9998 -1.0000 0.0004 -0.0850 -0.1148 0.1434

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8178
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.052
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_min         5.134
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  23.00   1.00    1.00    --    0.00 -77.00-120.00   42
  2  ω    -16.00  19.00   1.00    1.00    --    0.00 -77.00 150.00   35
  3  ω    -17.00  10.00   1.00    1.00    --    0.00 -77.00 120.00   27
  4  ω     47.00  73.00   1.00    1.50    --   54.00  61.00 -47.00   26
  5  ω     16.00  72.00   1.00    1.50    --   54.00 -57.00 -30.00   56
  6  ω    -16.00  75.00   1.00    1.50    --   54.00 -37.00-180.00   91
  7  ω     45.00  87.00   1.00    3.00    --  108.00 -91.00-120.00   42
  8  ω     45.00 126.00   1.00    3.00    --  108.00 -63.00  60.00   81
  9  ω     61.00 107.00   1.00    3.00    --  108.00 -91.00 -60.00   46
 10  ω    121.00 164.00   1.00    3.00    --  108.00 111.00  60.00   43
 11  ω     55.00 103.00   1.00    3.00    --  108.00 -91.00  30.00   48
 12  ω     37.00  64.00   1.00    3.00    --  108.00 -91.00-150.00   27
 13  ω    148.00 174.00   1.00    3.00    --  108.00  77.00 -90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0266056000
_diffrn_orient_matrix_UB_12      0.1382026000
_diffrn_orient_matrix_UB_13      0.0340186000
_diffrn_orient_matrix_UB_21      -0.0409808000
_diffrn_orient_matrix_UB_22      0.0328900000
_diffrn_orient_matrix_UB_23      0.0663833000
_diffrn_orient_matrix_UB_31      0.0247830000
_diffrn_orient_matrix_UB_32      -0.0938030000
_diffrn_orient_matrix_UB_33      0.0732666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2987
_reflns_number_total             3350
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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         0.420
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.00027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.030
_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)+(0.0510P)²+2.2558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.66893(5) 0.20751(16) 0.29474(10) 0.0128(3) Uani 1 1 d . . . . .
C2 C 0.62584(6) 0.17020(17) 0.25452(10) 0.0146(3) Uani 1 1 d . . . . .
H2 H 0.6251(6) 0.097(2) 0.2115(13) 0.018(5) Uiso 1 1 d . . . . .
C3 C 0.58427(5) 0.23863(17) 0.28122(10) 0.0154(3) Uani 1 1 d . . . . .
H3 H 0.5541(7) 0.209(2) 0.2532(12) 0.018(5) Uiso 1 1 d . . . . .
C4 C 0.58586(5) 0.34854(17) 0.34722(10) 0.0138(3) Uani 1 1 d . . . . .
C5 C 0.62890(5) 0.38842(16) 0.38608(10) 0.0124(3) Uani 1 1 d . . . . .
H5 H 0.6297(6) 0.463(2) 0.4323(13) 0.015(4) Uiso 1 1 d . . . . .
C6 C 0.67088(5) 0.31748(16) 0.36216(10) 0.0114(3) Uani 1 1 d . . . . .
C7 C 0.71575(5) 0.34586(16) 0.41638(10) 0.0117(3) Uani 1 1 d . . . . .
H7 H 0.7133(6) 0.442(2) 0.4443(12) 0.011(4) Uiso 1 1 d . . . . .
C8 C 0.80276(5) 0.31415(16) 0.40018(10) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.84437(6) 0.33537(17) 0.35060(11) 0.0167(3) Uani 1 1 d . . . . .
H9 H 0.8422(6) 0.365(2) 0.2889(13) 0.018(4) Uiso 1 1 d . . . . .
C10 C 0.88854(6) 0.31193(18) 0.38954(12) 0.0202(4) Uani 1 1 d . . . . .
H10 H 0.9160(7) 0.329(2) 0.3553(13) 0.026(5) Uiso 1 1 d . . . . .
C11 C 0.89148(6) 0.26358(18) 0.47925(12) 0.0201(4) Uani 1 1 d . . . . .
H11 H 0.9211(7) 0.245(2) 0.5061(13) 0.023(5) Uiso 1 1 d . . . . .
C12 C 0.85032(6) 0.24046(17) 0.52857(11) 0.0168(3) Uani 1 1 d . . . . .
H12 H 0.8524(7) 0.204(2) 0.5898(14) 0.022(5) Uiso 1 1 d . . . . .
C13 C 0.80575(5) 0.26652(16) 0.49028(10) 0.0134(3) Uani 1 1 d . . . . .
C14 C 0.71907(5) 0.23010(16) 0.49441(10) 0.0121(3) Uani 1 1 d . . . . .
H14 H 0.7176(6) 0.130(2) 0.4678(11) 0.008(4) Uiso 1 1 d . . . . .
C15 C 0.67733(5) 0.25112(16) 0.55815(10) 0.0124(3) Uani 1 1 d . . . . .
C16 C 0.63640(5) 0.16665(16) 0.54747(10) 0.0135(3) Uani 1 1 d . . . . .
H16 H 0.6365(6) 0.088(2) 0.5068(12) 0.015(4) Uiso 1 1 d . . . . .
C17 C 0.59498(5) 0.20113(17) 0.59453(10) 0.0151(3) Uani 1 1 d . . . . .
C18 C 0.59431(6) 0.32005(18) 0.65435(10) 0.0171(3) Uani 1 1 d . . . . .
H18 H 0.5656(7) 0.345(2) 0.6876(13) 0.022(5) Uiso 1 1 d . . . . .
C19 C 0.63522(6) 0.40171(18) 0.66834(10) 0.0165(3) Uani 1 1 d . . . . .
H19 H 0.6352(7) 0.483(2) 0.7105(13) 0.021(5) Uiso 1 1 d . . . . .
C20 C 0.67651(5) 0.36840(16) 0.62085(10) 0.0131(3) Uani 1 1 d . . . . .
C21 C 0.54117(5) 0.42320(18) 0.37784(11) 0.0169(3) Uani 1 1 d . . . . .
C22 C 0.55062(5) 0.11376(18) 0.57782(11) 0.0184(3) Uani 1 1 d . . . . .
F1 F 0.53228(4) 0.54838(12) 0.33180(8) 0.0320(3) Uani 1 1 d . . . . .
F2 F 0.50266(3) 0.33814(12) 0.36746(8) 0.0294(3) Uani 1 1 d . . . . .
F3 F 0.54317(3) 0.46188(13) 0.46502(7) 0.0294(3) Uani 1 1 d . . . . .
F4 F 0.54574(4) 0.07674(14) 0.48989(7) 0.0340(3) Uani 1 1 d . . . . .
F5 F 0.51154(3) 0.18591(13) 0.60035(9) 0.0406(3) Uani 1 1 d . . . . .
F6 F 0.55019(4) -0.01539(13) 0.62209(8) 0.0363(3) Uani 1 1 d . . . . .
N1 N 0.75790(4) 0.33380(14) 0.35732(8) 0.0133(3) Uani 1 1 d . . . . .
H1 H 0.7592(7) 0.409(2) 0.3208(13) 0.021(5) Uiso 1 1 d . . . . .
N2 N 0.76409(4) 0.25098(14) 0.54382(9) 0.0139(3) Uani 1 1 d . . . . .
H2A H 0.7684(7) 0.179(2) 0.5857(14) 0.027(5) Uiso 1 1 d . . . . .
O1 O 0.70853(4) 0.13213(12) 0.26729(7) 0.0159(2) Uani 1 1 d . . . . .
H1A H 0.7318(9) 0.183(3) 0.2861(16) 0.045(7) Uiso 1 1 d . . . . .
O2 O 0.71560(4) 0.45586(12) 0.63592(7) 0.0162(2) Uani 1 1 d . . . . .
H2B H 0.7391(8) 0.405(3) 0.6141(15) 0.035(6) Uiso 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
C1 C2 1.390(2) . ?
C1 C6 1.407(2) . ?
C1 O1 1.3675(18) . ?
C2 H2 0.92(2) . ?
C2 C3 1.380(2) . ?
C3 H3 0.983(19) . ?
C3 C4 1.392(2) . ?
C4 C5 1.387(2) . ?
C4 C21 1.497(2) . ?
C5 H5 0.958(19) . ?
C5 C6 1.389(2) . ?
C6 C7 1.515(2) . ?
C7 H7 0.968(18) . ?
C7 C14 1.558(2) . ?
C7 N1 1.4747(18) . ?
C8 C9 1.393(2) . ?
C8 C13 1.398(2) . ?
C8 N1 1.4221(19) . ?
C9 H9 0.949(19) . ?
C9 C10 1.385(2) . ?
C10 H10 0.93(2) . ?
C10 C11 1.394(3) . ?
C11 H11 0.94(2) . ?
C11 C12 1.383(2) . ?
C12 H12 0.96(2) . ?
C12 C13 1.395(2) . ?
C13 N2 1.4195(19) . ?
C14 H14 0.989(18) . ?
C14 C15 1.515(2) . ?
C14 N2 1.4727(18) . ?
C15 C16 1.391(2) . ?
C15 C20 1.407(2) . ?
C16 H16 0.928(19) . ?
C16 C17 1.391(2) . ?
C17 C18 1.391(2) . ?
C17 C22 1.497(2) . ?
C18 H18 0.97(2) . ?
C18 C19 1.383(2) . ?
C19 H19 0.96(2) . ?
C19 C20 1.389(2) . ?
C20 O2 1.3727(18) . ?
C21 F1 1.3438(19) . ?
C21 F2 1.3375(18) . ?
C21 F3 1.3322(19) . ?
C22 F4 1.345(2) . ?
C22 F5 1.3209(19) . ?
C22 F6 1.338(2) . ?
N1 H1 0.87(2) . ?
N2 H2A 0.91(2) . ?
O1 H1A 0.85(3) . ?
O2 H2B 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.43(14) . . ?
O1 C1 C2 117.57(13) . . ?
O1 C1 C6 121.99(13) . . ?
C1 C2 H2 119.3(11) . . ?
C3 C2 C1 120.52(14) . . ?
C3 C2 H2 120.1(11) . . ?
C2 C3 H3 119.2(11) . . ?
C2 C3 C4 119.50(14) . . ?
C4 C3 H3 121.3(11) . . ?
C3 C4 C21 120.41(14) . . ?
C5 C4 C3 120.16(14) . . ?
C5 C4 C21 119.43(14) . . ?
C4 C5 H5 119.8(11) . . ?
C4 C5 C6 121.12(14) . . ?
C6 C5 H5 119.0(11) . . ?
C1 C6 C7 121.62(13) . . ?
C5 C6 C1 118.21(13) . . ?
C5 C6 C7 119.72(13) . . ?
C6 C7 H7 108.5(10) . . ?
C6 C7 C14 108.96(12) . . ?
C14 C7 H7 107.3(10) . . ?
N1 C7 C6 110.25(11) . . ?
N1 C7 H7 112.0(10) . . ?
N1 C7 C14 109.70(12) . . ?
C9 C8 C13 119.32(14) . . ?
C9 C8 N1 119.71(14) . . ?
C13 C8 N1 120.89(13) . . ?
C8 C9 H9 119.1(11) . . ?
C10 C9 C8 121.04(15) . . ?
C10 C9 H9 119.9(11) . . ?
C9 C10 H10 119.5(12) . . ?
C9 C10 C11 119.59(15) . . ?
C11 C10 H10 120.9(12) . . ?
C10 C11 H11 120.6(12) . . ?
C12 C11 C10 119.71(15) . . ?
C12 C11 H11 119.6(12) . . ?
C11 C12 H12 119.5(11) . . ?
C11 C12 C13 120.97(15) . . ?
C13 C12 H12 119.5(11) . . ?
C8 C13 N2 120.56(13) . . ?
C12 C13 C8 119.35(14) . . ?
C12 C13 N2 120.03(14) . . ?
C7 C14 H14 108.7(10) . . ?
C15 C14 C7 109.04(12) . . ?
C15 C14 H14 109.2(10) . . ?
N2 C14 C7 109.27(12) . . ?
N2 C14 H14 110.4(10) . . ?
N2 C14 C15 110.11(12) . . ?
C16 C15 C14 120.15(13) . . ?
C16 C15 C20 118.38(14) . . ?
C20 C15 C14 120.94(13) . . ?
C15 C16 H16 119.3(11) . . ?
C15 C16 C17 120.90(14) . . ?
C17 C16 H16 119.8(11) . . ?
C16 C17 C22 119.83(14) . . ?
C18 C17 C16 120.04(14) . . ?
C18 C17 C22 120.09(14) . . ?
C17 C18 H18 120.7(12) . . ?
C19 C18 C17 119.77(14) . . ?
C19 C18 H18 119.5(12) . . ?
C18 C19 H19 120.2(11) . . ?
C18 C19 C20 120.31(14) . . ?
C20 C19 H19 119.4(11) . . ?
C19 C20 C15 120.53(14) . . ?
O2 C20 C15 121.86(13) . . ?
O2 C20 C19 117.59(13) . . ?
F1 C21 C4 112.62(13) . . ?
F2 C21 C4 112.70(13) . . ?
F2 C21 F1 106.07(12) . . ?
F3 C21 C4 111.93(13) . . ?
F3 C21 F1 105.84(13) . . ?
F3 C21 F2 107.20(13) . . ?
F4 C22 C17 112.01(13) . . ?
F5 C22 C17 113.02(14) . . ?
F5 C22 F4 106.27(14) . . ?
F5 C22 F6 107.56(13) . . ?
F6 C22 C17 112.87(13) . . ?
F6 C22 F4 104.53(14) . . ?
C7 N1 H1 109.8(13) . . ?
C8 N1 C7 117.44(12) . . ?
C8 N1 H1 109.7(13) . . ?
C13 N2 C14 116.61(12) . . ?
C13 N2 H2A 109.8(13) . . ?
C14 N2 H2A 111.0(13) . . ?
C1 O1 H1A 105.1(17) . . ?
C20 O2 H2B 104.1(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.87(2) 2.35(2) 3.1526(17) 153.8(17) 8_765 yes
N2 H2A O2 0.91(2) 2.19(2) 3.0495(17) 156.8(18) 8_755 yes
O1 H1A N1 0.85(3) 1.87(3) 2.6490(17) 152(2) . yes
O2 H2B N2 0.87(2) 1.87(2) 2.6718(17) 152(2) . yes

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
C1 C2 C3 C4 1.7(2) . . . . ?
C1 C6 C7 C14 -81.22(16) . . . . ?
C1 C6 C7 N1 39.22(18) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C6 C7 171.37(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 C21 -179.41(14) . . . . ?
C3 C4 C5 C6 -1.8(2) . . . . ?
C3 C4 C21 F1 -93.55(17) . . . . ?
C3 C4 C21 F2 26.4(2) . . . . ?
C3 C4 C21 F3 147.34(14) . . . . ?
C4 C5 C6 C1 2.4(2) . . . . ?
C4 C5 C6 C7 -170.06(13) . . . . ?
C5 C4 C21 F1 87.32(17) . . . . ?
C5 C4 C21 F2 -152.72(14) . . . . ?
C5 C4 C21 F3 -31.8(2) . . . . ?
C5 C6 C7 C14 90.95(15) . . . . ?
C5 C6 C7 N1 -148.61(13) . . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
C6 C7 C14 C15 -63.18(15) . . . . ?
C6 C7 C14 N2 176.43(11) . . . . ?
C6 C7 N1 C8 -162.07(12) . . . . ?
C7 C14 C15 C16 95.09(15) . . . . ?
C7 C14 C15 C20 -76.34(17) . . . . ?
C7 C14 N2 C13 -47.08(16) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C8 C13 N2 C14 22.93(19) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
C9 C8 C13 N2 176.87(13) . . . . ?
C9 C8 N1 C7 -165.52(13) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C11 C12 C13 C8 1.2(2) . . . . ?
C11 C12 C13 N2 -176.05(14) . . . . ?
C12 C13 N2 C14 -159.88(13) . . . . ?
C13 C8 C9 C10 -0.9(2) . . . . ?
C13 C8 N1 C7 17.7(2) . . . . ?
C14 C7 N1 C8 -42.07(17) . . . . ?
C14 C15 C16 C17 -168.80(13) . . . . ?
C14 C15 C20 C19 169.33(13) . . . . ?
C14 C15 C20 O2 -9.1(2) . . . . ?
C15 C14 N2 C13 -166.81(12) . . . . ?
C15 C16 C17 C18 -1.0(2) . . . . ?
C15 C16 C17 C22 176.51(14) . . . . ?
C16 C15 C20 C19 -2.2(2) . . . . ?
C16 C15 C20 O2 179.33(13) . . . . ?
C16 C17 C18 C19 -1.4(2) . . . . ?
C16 C17 C22 F4 -37.7(2) . . . . ?
C16 C17 C22 F5 -157.66(14) . . . . ?
C16 C17 C22 F6 80.00(18) . . . . ?
C17 C18 C19 C20 2.0(2) . . . . ?
C18 C17 C22 F4 139.89(15) . . . . ?
C18 C17 C22 F5 19.9(2) . . . . ?
C18 C17 C22 F6 -102.46(17) . . . . ?
C18 C19 C20 C15 -0.2(2) . . . . ?
C18 C19 C20 O2 178.32(13) . . . . ?
C20 C15 C16 C17 2.8(2) . . . . ?
C21 C4 C5 C6 177.33(13) . . . . ?
C22 C17 C18 C19 -178.97(14) . . . . ?
N1 C7 C14 C15 176.04(12) . . . . ?
N1 C7 C14 N2 55.64(15) . . . . ?
N1 C8 C9 C10 -177.67(14) . . . . ?
N1 C8 C13 C12 176.43(13) . . . . ?
N1 C8 C13 N2 -6.4(2) . . . . ?
N2 C14 C15 C16 -145.03(13) . . . . ?
N2 C14 C15 C20 43.54(18) . . . . ?
O1 C1 C2 C3 177.89(13) . . . . ?
O1 C1 C6 C5 -179.89(13) . . . . ?
O1 C1 C6 C7 -7.6(2) . . . . ?

_olex2_date_sample_data_collection 2020-01-08
_olex2_date_sample_submission    2019-12-17
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id 'KL CF3 col NMR'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.110
_oxdiff_exptl_absorpt_empirical_full_min 0.838
####################################################################### 
# 
# 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_mn1904
_database_code_depnum_ccdc_archive 'CCDC 1983171'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-09-11
_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 H18 N2 O2'
_chemical_formula_sum            'C20 H18 N2 O2'
_chemical_formula_weight         318.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H18 N2 O2'
_chemical_oxdiff_usercomment     'Katie Lamb Salophen Cry'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.16584(13)
_cell_length_b                   10.4417(2)
_cell_length_c                   21.8016(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.8756(17)
_cell_angle_gamma                90
_cell_volume                     1619.54(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2555
_cell_measurement_temperature    110.00(14)
_cell_measurement_theta_max      70.6950
_cell_measurement_theta_min      8.1660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0246
0 0 1 0.0229
-1 -1 -1 0.0521
1 1 1 0.0462
1 -1 -1 0.1022
-1 1 1 0.0964
-1 -1 1 0.0484
1 1 -1 0.0448

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.048
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.0002 -0.9990 0.0567 -0.0430 0.0016
0.0000 -0.0002 0.9990 -0.0567 0.0430 -0.0016
-1.0024 -0.9989 -0.9993 0.1286 0.0180 0.2463
1.0024 0.9989 0.9993 -0.1286 -0.0180 -0.2463
0.9995 -1.0005 -1.0017 0.1566 0.1251 -0.1728
-0.9995 1.0005 1.0017 -0.1566 -0.1251 0.1728
-1.0023 -0.9992 0.9987 0.0153 0.1039 0.2431
1.0023 0.9992 -0.9987 -0.0153 -0.1039 -0.2431

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5918
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.045
_diffrn_reflns_theta_max         67.045
_diffrn_reflns_theta_min         4.085
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  62.00   1.00    1.00    --    0.00  57.00  30.00   37
  2  ω    -14.00  13.00   1.00    1.00    --    0.00  57.00  30.00   27
  3  ω    -61.00 -36.00   1.00    1.00    --    0.00 131.00 178.00   25
  4  ω     31.00 112.00   1.00    2.00    --   54.00-131.00 107.00   81
  5  ω     46.00 108.00   1.00    2.00    --   54.00  57.00 -60.00   62
  6  ω      9.00  67.00   1.00    2.00    --   54.00 -37.00  90.00   58
  7  ω     38.00 102.00   1.00    2.00    --   54.00  57.00  90.00   64
  8  ω     83.00 162.00   1.00    4.00    --  108.00  37.00  90.00   79
  9  ω     93.00 175.00   1.00    4.00    --  108.00  63.00 -60.00   82
 10  ω    100.00 169.00   1.00    4.00    --  108.00 111.00 -30.00   69
 11  ω     36.00 146.00   1.00    4.00    --  108.00 -91.00-180.00  110
 12  ω     86.00 113.00   1.00    4.00    --  108.00  50.00 150.00   27
 13  ω     67.00 138.00   1.00    4.00    --  108.00 -77.00 -30.00   71
 14  ω     41.00 130.00   1.00    4.00    --  108.00 -63.00 -60.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0138681000
_diffrn_orient_matrix_UB_12      -0.0858892000
_diffrn_orient_matrix_UB_13      -0.0567414000
_diffrn_orient_matrix_UB_21      0.0534762000
_diffrn_orient_matrix_UB_22      -0.1146865000
_diffrn_orient_matrix_UB_23      0.0429929000
_diffrn_orient_matrix_UB_31      -0.2093764000
_diffrn_orient_matrix_UB_32      -0.0349005000
_diffrn_orient_matrix_UB_33      -0.0015921000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2534
_reflns_number_total             2901
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00111(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.040
_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)+(0.0289P)²+0.5378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.56117(17) 0.09188(13) 0.16999(6) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.57067(18) 0.03517(14) 0.11277(7) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.535(2) -0.0542(18) 0.1079(7) 0.039(5) Uiso 1 1 d . . . . .
C3 C 0.62811(19) 0.10610(15) 0.06483(6) 0.0302(3) Uani 1 1 d . . . . .
H3 H 0.634(2) 0.0648(15) 0.0234(7) 0.029(4) Uiso 1 1 d . . . . .
C4 C 0.67870(19) 0.23345(15) 0.07383(7) 0.0300(3) Uani 1 1 d . . . . .
H4 H 0.721(2) 0.2850(16) 0.0395(7) 0.036(4) Uiso 1 1 d . . . . .
C5 C 0.67136(18) 0.28901(14) 0.13126(6) 0.0256(3) Uani 1 1 d . . . . .
H5 H 0.702(2) 0.3805(16) 0.1379(7) 0.031(4) Uiso 1 1 d . . . . .
C6 C 0.61156(16) 0.22056(12) 0.18022(6) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.59507(17) 0.28736(12) 0.24066(6) 0.0200(3) Uani 1 1 d . . . . .
H7 H 0.6687(19) 0.3663(14) 0.2421(6) 0.018(3) Uiso 1 1 d . . . . .
C8 C 0.38958(17) 0.32680(12) 0.24698(6) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.3161(19) 0.2478(14) 0.2469(6) 0.017(3) Uiso 1 1 d . . . . .
C9 C 0.30839(16) 0.40918(12) 0.19368(6) 0.0203(3) Uani 1 1 d . . . . .
C10 C 0.36332(16) 0.53705(12) 0.18886(6) 0.0218(3) Uani 1 1 d . . . . .
C11 C 0.30166(18) 0.60893(14) 0.13685(6) 0.0265(3) Uani 1 1 d . . . . .
H11 H 0.346(2) 0.6981(17) 0.1357(7) 0.034(4) Uiso 1 1 d . . . . .
C12 C 0.18193(19) 0.55468(15) 0.08939(6) 0.0303(3) Uani 1 1 d . . . . .
H12 H 0.138(2) 0.6049(17) 0.0521(7) 0.036(4) Uiso 1 1 d . . . . .
C13 C 0.12102(19) 0.42954(15) 0.09409(6) 0.0298(3) Uani 1 1 d . . . . .
H13 H 0.037(2) 0.3922(17) 0.0609(8) 0.039(5) Uiso 1 1 d . . . . .
C14 C 0.18464(18) 0.35785(13) 0.14604(6) 0.0252(3) Uani 1 1 d . . . . .
H14 H 0.146(2) 0.2676(16) 0.1503(7) 0.031(4) Uiso 1 1 d . . . . .
C15 C 0.63492(17) 0.25249(13) 0.35208(6) 0.0222(3) Uani 1 1 d . . . . .
C16 C 0.74281(18) 0.20610(13) 0.40489(6) 0.0257(3) Uani 1 1 d . . . . .
H16 H 0.839(2) 0.1390(16) 0.3992(7) 0.031(4) Uiso 1 1 d . . . . .
C17 C 0.71460(19) 0.24977(14) 0.46311(6) 0.0284(3) Uani 1 1 d . . . . .
H17 H 0.793(2) 0.2162(15) 0.4998(7) 0.030(4) Uiso 1 1 d . . . . .
C18 C 0.5755(2) 0.33965(14) 0.46932(6) 0.0286(3) Uani 1 1 d . . . . .
H18 H 0.554(2) 0.3688(16) 0.5110(7) 0.036(4) Uiso 1 1 d . . . . .
C19 C 0.46726(19) 0.38694(13) 0.41702(6) 0.0259(3) Uani 1 1 d . . . . .
H19 H 0.364(2) 0.4533(15) 0.4204(7) 0.029(4) Uiso 1 1 d . . . . .
C20 C 0.49694(17) 0.34508(12) 0.35844(6) 0.0218(3) Uani 1 1 d . . . . .
N1 N 0.65803(15) 0.20304(11) 0.29308(5) 0.0225(2) Uani 1 1 d . . . . .
H1 H 0.777(2) 0.1744(16) 0.2912(7) 0.031(4) Uiso 1 1 d . . . . .
N2 N 0.39266(15) 0.39875(11) 0.30521(5) 0.0219(2) Uani 1 1 d . . . . .
H2A H 0.277(2) 0.4253(16) 0.3116(7) 0.034(4) Uiso 1 1 d . . . . .
O1 O 0.49956(13) 0.01714(9) 0.21551(5) 0.0272(2) Uani 1 1 d . . . . .
H1A H 0.530(2) 0.0581(18) 0.2529(8) 0.043(5) Uiso 1 1 d . . . . .
O2 O 0.48031(12) 0.59603(9) 0.23507(4) 0.0256(2) Uani 1 1 d . . . . .
H2B H 0.478(3) 0.547(2) 0.2709(9) 0.056(6) Uiso 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
C1 C2 1.3899(19) . ?
C1 C6 1.4022(18) . ?
C1 O1 1.3761(16) . ?
C2 H2 0.970(18) . ?
C2 C3 1.383(2) . ?
C3 H3 1.006(15) . ?
C3 C4 1.386(2) . ?
C4 H4 0.999(17) . ?
C4 C5 1.387(2) . ?
C5 H5 0.987(17) . ?
C5 C6 1.3940(18) . ?
C6 C7 1.5079(17) . ?
C7 H7 0.977(15) . ?
C7 C8 1.5510(16) . ?
C7 N1 1.4702(16) . ?
C8 H8 0.979(14) . ?
C8 C9 1.5056(17) . ?
C8 N2 1.4730(16) . ?
C9 C10 1.3995(18) . ?
C9 C14 1.3900(18) . ?
C10 C11 1.3873(19) . ?
C10 O2 1.3766(16) . ?
C11 H11 0.986(17) . ?
C11 C12 1.384(2) . ?
C12 H12 0.986(17) . ?
C12 C13 1.385(2) . ?
C13 H13 0.968(17) . ?
C13 C14 1.388(2) . ?
C14 H14 0.989(17) . ?
C15 C16 1.3946(18) . ?
C15 C20 1.4016(18) . ?
C15 N1 1.4142(16) . ?
C16 H16 0.999(16) . ?
C16 C17 1.3861(19) . ?
C17 H17 0.983(16) . ?
C17 C18 1.387(2) . ?
C18 H18 0.987(16) . ?
C18 C19 1.391(2) . ?
C19 H19 1.023(16) . ?
C19 C20 1.3900(18) . ?
C20 N2 1.4184(16) . ?
N1 H1 0.909(17) . ?
N2 H2A 0.902(17) . ?
O1 H1A 0.923(19) . ?
O2 H2B 0.94(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.77(12) . . ?
O1 C1 C2 117.40(12) . . ?
O1 C1 C6 121.83(12) . . ?
C1 C2 H2 117.9(10) . . ?
C3 C2 C1 120.07(13) . . ?
C3 C2 H2 122.0(10) . . ?
C2 C3 H3 119.7(9) . . ?
C2 C3 C4 120.20(13) . . ?
C4 C3 H3 120.0(9) . . ?
C3 C4 H4 120.6(10) . . ?
C3 C4 C5 119.45(13) . . ?
C5 C4 H4 120.0(10) . . ?
C4 C5 H5 120.3(9) . . ?
C4 C5 C6 121.69(13) . . ?
C6 C5 H5 117.9(9) . . ?
C1 C6 C7 122.45(11) . . ?
C5 C6 C1 117.80(12) . . ?
C5 C6 C7 119.69(12) . . ?
C6 C7 H7 108.6(8) . . ?
C6 C7 C8 112.02(10) . . ?
C8 C7 H7 106.7(8) . . ?
N1 C7 C6 110.70(10) . . ?
N1 C7 H7 111.5(8) . . ?
N1 C7 C8 107.23(10) . . ?
C7 C8 H8 107.0(8) . . ?
C9 C8 C7 111.49(10) . . ?
C9 C8 H8 108.8(8) . . ?
N2 C8 C7 107.19(10) . . ?
N2 C8 H8 112.6(8) . . ?
N2 C8 C9 109.77(10) . . ?
C10 C9 C8 121.12(11) . . ?
C14 C9 C8 120.63(12) . . ?
C14 C9 C10 118.15(12) . . ?
C11 C10 C9 120.84(12) . . ?
O2 C10 C9 121.60(11) . . ?
O2 C10 C11 117.56(12) . . ?
C10 C11 H11 117.4(9) . . ?
C12 C11 C10 119.87(13) . . ?
C12 C11 H11 122.7(9) . . ?
C11 C12 H12 120.4(10) . . ?
C11 C12 C13 120.22(13) . . ?
C13 C12 H12 119.4(10) . . ?
C12 C13 H13 119.9(10) . . ?
C12 C13 C14 119.57(13) . . ?
C14 C13 H13 120.5(10) . . ?
C9 C14 H14 117.3(9) . . ?
C13 C14 C9 121.30(13) . . ?
C13 C14 H14 121.4(9) . . ?
C16 C15 C20 119.07(12) . . ?
C16 C15 N1 120.69(12) . . ?
C20 C15 N1 120.17(11) . . ?
C15 C16 H16 117.6(9) . . ?
C17 C16 C15 120.96(13) . . ?
C17 C16 H16 121.4(9) . . ?
C16 C17 H17 119.7(9) . . ?
C16 C17 C18 119.81(13) . . ?
C18 C17 H17 120.4(9) . . ?
C17 C18 H18 119.4(10) . . ?
C17 C18 C19 119.80(13) . . ?
C19 C18 H18 120.8(10) . . ?
C18 C19 H19 121.3(8) . . ?
C20 C19 C18 120.66(13) . . ?
C20 C19 H19 118.1(8) . . ?
C15 C20 N2 120.03(11) . . ?
C19 C20 C15 119.68(12) . . ?
C19 C20 N2 120.27(12) . . ?
C7 N1 H1 111.3(10) . . ?
C15 N1 C7 115.47(11) . . ?
C15 N1 H1 111.9(10) . . ?
C8 N2 H2A 111.7(10) . . ?
C20 N2 C8 117.12(10) . . ?
C20 N2 H2A 113.6(10) . . ?
C1 O1 H1A 108.2(11) . . ?
C10 O2 H2B 107.2(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.909(17) 2.064(17) 2.9534(14) 165.6(14) 2_645 yes
N2 H2A O1 0.902(17) 2.216(17) 3.0542(14) 154.5(14) 2 yes
O1 H1A N1 0.923(19) 1.926(19) 2.7308(15) 144.5(15) . yes
O2 H2B N2 0.94(2) 1.85(2) 2.6844(14) 146.4(17) . yes

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
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C6 C7 C8 -78.06(15) . . . . ?
C1 C6 C7 N1 41.56(15) . . . . ?
C2 C1 C6 C5 -0.09(18) . . . . ?
C2 C1 C6 C7 177.19(11) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C1 0.98(19) . . . . ?
C4 C5 C6 C7 -176.38(12) . . . . ?
C5 C6 C7 C8 99.17(13) . . . . ?
C5 C6 C7 N1 -141.21(11) . . . . ?
C6 C1 C2 C3 -0.80(19) . . . . ?
C6 C7 C8 C9 -55.87(14) . . . . ?
C6 C7 C8 N2 -176.02(10) . . . . ?
C6 C7 N1 C15 -175.30(10) . . . . ?
C7 C8 C9 C10 -73.87(14) . . . . ?
C7 C8 C9 C14 102.41(13) . . . . ?
C7 C8 N2 C20 -47.03(14) . . . . ?
C8 C7 N1 C15 -52.83(14) . . . . ?
C8 C9 C10 C11 173.90(11) . . . . ?
C8 C9 C10 O2 -5.88(17) . . . . ?
C8 C9 C14 C13 -174.48(12) . . . . ?
C9 C8 N2 C20 -168.27(10) . . . . ?
C9 C10 C11 C12 1.03(19) . . . . ?
C10 C9 C14 C13 1.91(18) . . . . ?
C10 C11 C12 C13 1.1(2) . . . . ?
C11 C12 C13 C14 -1.6(2) . . . . ?
C12 C13 C14 C9 0.1(2) . . . . ?
C14 C9 C10 C11 -2.48(17) . . . . ?
C14 C9 C10 O2 177.75(11) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C15 C20 N2 C8 19.35(17) . . . . ?
C16 C15 C20 C19 -1.36(19) . . . . ?
C16 C15 C20 N2 176.54(11) . . . . ?
C16 C15 N1 C7 -157.74(11) . . . . ?
C16 C17 C18 C19 -1.0(2) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C19 C20 C15 1.22(19) . . . . ?
C18 C19 C20 N2 -176.67(12) . . . . ?
C19 C20 N2 C8 -162.77(11) . . . . ?
C20 C15 C16 C17 0.32(19) . . . . ?
C20 C15 N1 C7 25.09(16) . . . . ?
N1 C7 C8 C9 -177.50(10) . . . . ?
N1 C7 C8 N2 62.34(12) . . . . ?
N1 C15 C16 C17 -176.88(12) . . . . ?
N1 C15 C20 C19 175.85(11) . . . . ?
N1 C15 C20 N2 -6.25(18) . . . . ?
N2 C8 C9 C10 44.76(15) . . . . ?
N2 C8 C9 C14 -138.96(11) . . . . ?
O1 C1 C2 C3 178.77(12) . . . . ?
O1 C1 C6 C5 -179.64(11) . . . . ?
O1 C1 C6 C7 -2.35(18) . . . . ?
O2 C10 C11 C12 -179.19(11) . . . . ?

_olex2_date_sample_data_collection 2019-09-03
_olex2_date_sample_submission    2019-08-21
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id 'KL Salophen Cry'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.869
####################################################################### 
# 
# 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_mn1601
_database_code_depnum_ccdc_archive 'CCDC 1983173'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_audit_creation_date             2016-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.33(C30 H38 N2 O4)'
_chemical_formula_sum            'C10 H12.67 N0.67 O1.33'
_chemical_formula_weight         163.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H34 Cl1 Cr1 N2 O4'
_chemical_oxdiff_usercomment     'Katie KL OMe cat THF sample 1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   17.8343(6)
_cell_length_b                   12.4405(4)
_cell_length_c                   13.0921(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.301(4)
_cell_angle_gamma                90
_cell_volume                     2773.29(17)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    2622
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      71.1550
_cell_measurement_theta_min      7.9390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.648
_exptl_absorpt_correction_T_min  0.518
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2008
_exptl_crystal_size_mid          0.1607
_exptl_crystal_size_min          0.1298
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.486
_diffrn_reflns_theta_min         4.402
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
  2 omega   42.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega   40.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   41.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
  5 omega   27.00   54.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   39.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   60.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   59.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00   96.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 10 omega   52.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 11 omega   43.00  169.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  120.0000 126

#__ type_ start__ end____ width___ exp.time_
 12 omega   81.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
 13 omega   17.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega   -3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 15 omega  -12.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
 16 omega  -59.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356161000
_diffrn_orient_matrix_UB_12      0.1053144000
_diffrn_orient_matrix_UB_13      -0.0266910000
_diffrn_orient_matrix_UB_21      -0.0407470000
_diffrn_orient_matrix_UB_22      -0.0187870000
_diffrn_orient_matrix_UB_23      -0.1199950000
_diffrn_orient_matrix_UB_31      -0.0724565000
_diffrn_orient_matrix_UB_32      0.0624686000
_diffrn_orient_matrix_UB_33      0.0086931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2332
_reflns_number_total             2640
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.230
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.062
_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)+(0.0505P)²+1.3821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.047) H1(0.03) H8(0.025) H10(0.031) H12(0.025) H14(0.036)
 H11A(0.054) H11B(0.054) H11C(0.054) H15(0.043) H3A(0.068) H3B(0.068)
 H3C(0.068) H1A(0.073) H1B(0.073) H1C(0.073) H2A(0.076) H2B(0.076) H2C(0.076)
 Fixed X: H2(0.63) H1(0.5174) H8(0.4209) H10(0.6053) H12(0.4345) H14(0.528)
 H11A(0.3523) H11B(0.3599) H11C(0.3804) H15(0.5133) H3A(0.7497) H3B(0.8151)
 H3C(0.7344) H1A(0.7476) H1B(0.8231) H1C(0.7572) H2A(0.719) H2B(0.802)
 H2C(0.7307)
 Fixed Y: H2(0.333) H1(0.2593) H8(0.5408) H10(0.7225) H12(0.36) H14(0.0678)
 H11A(0.6858) H11B(0.8073) H11C(0.7175) H15(-0.0931) H3A(0.4335) H3B(0.5162)
 H3C(0.5166) H1A(0.6219) H1B(0.58) H1C(0.499) H2A(0.7115) H2B(0.7041)
 H2C(0.7509)
 Fixed Z: H2(0.7031) H1(0.5906) H8(0.6052) H10(0.6018) H12(0.6545) H14(0.5887)
 H11A(0.5146) H11B(0.5479) H11C(0.636) H15(0.6684) H3A(0.6253) H3B(0.6215)
 H3C(0.5313) H1A(0.8312) H1B(0.8059) H1C(0.8119) H2A(0.5663) H2B(0.6513)
 H2C(0.6838)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.46158(5) 0.73712(7) 0.56337(7) 0.0290(2) Uani 1 1 d . . . . .
O2 O 0.65551(5) 0.38852(7) 0.70693(8) 0.0315(2) Uani 1 1 d . . . . .
H2 H 0.6300 0.3330 0.7031 0.047 Uiso 1 1 calc GR . . . .
N1 N 0.52607(6) 0.26357(8) 0.65864(8) 0.0246(2) Uani 1 1 d . . . . .
H1 H 0.5174 0.2593 0.5906 0.030 Uiso 1 1 d R . . . .
C9 C 0.50548(7) 0.64555(9) 0.59910(9) 0.0232(3) Uani 1 1 d . . . . .
C8 C 0.47470(7) 0.54839(9) 0.61723(8) 0.0207(2) Uani 1 1 d . . . . .
H8 H 0.4209 0.5408 0.6052 0.025 Uiso 1 1 calc R . . . .
C13 C 0.50978(7) 0.16557(9) 0.70199(10) 0.0236(3) Uani 1 1 d . . . . .
C7 C 0.52484(6) 0.46171(9) 0.65372(8) 0.0203(2) Uani 1 1 d . . . . .
C10 C 0.58577(7) 0.65627(10) 0.61484(9) 0.0259(3) Uani 1 1 d . . . . .
H10 H 0.6053 0.7225 0.6018 0.031 Uiso 1 1 calc R . . . .
C12 C 0.49145(6) 0.36135(9) 0.68834(8) 0.0206(2) Uani 1 1 d . . . . .
H12 H 0.4345 0.3600 0.6545 0.025 Uiso 1 1 calc R . . . .
C6 C 0.60555(7) 0.47294(9) 0.66894(9) 0.0229(3) Uani 1 1 d . . . . .
C5 C 0.63762(7) 0.57131(10) 0.64935(9) 0.0249(3) Uani 1 1 d . . . . .
C14 C 0.51706(7) 0.06806(10) 0.65387(11) 0.0302(3) Uani 1 1 d . . . . .
H14 H 0.5280 0.0678 0.5887 0.036 Uiso 1 1 calc R . . . .
C11 C 0.38203(8) 0.73690(11) 0.56567(12) 0.0357(3) Uani 1 1 d . . . . .
H11A H 0.3523 0.6858 0.5146 0.054 Uiso 1 1 calc GR . . . .
H11B H 0.3599 0.8073 0.5479 0.054 Uiso 1 1 calc GR . . . .
H11C H 0.3804 0.7175 0.6360 0.054 Uiso 1 1 calc GR . . . .
C15 C 0.50824(8) -0.02846(10) 0.70139(12) 0.0362(3) Uani 1 1 d . . . . .
H15 H 0.5133 -0.0931 0.6684 0.043 Uiso 1 1 calc R . . . .
C4 C 0.72678(7) 0.58590(11) 0.67125(11) 0.0336(3) Uani 1 1 d . . . . .
C3 C 0.75957(9) 0.50551(13) 0.60626(13) 0.0455(4) Uani 1 1 d . . . . .
H3A H 0.7497 0.4335 0.6253 0.068 Uiso 1 1 calc GR . . . .
H3B H 0.8151 0.5162 0.6215 0.068 Uiso 1 1 calc GR . . . .
H3C H 0.7344 0.5166 0.5313 0.068 Uiso 1 1 calc GR . . . .
C1 C 0.76748(8) 0.57022(16) 0.79132(12) 0.0486(4) Uani 1 1 d . . . . .
H1A H 0.7476 0.6219 0.8312 0.073 Uiso 1 1 calc GR . . . .
H1B H 0.8231 0.5800 0.8059 0.073 Uiso 1 1 calc GR . . . .
H1C H 0.7572 0.4990 0.8119 0.073 Uiso 1 1 calc GR . . . .
C2 C 0.74645(9) 0.69859(14) 0.64029(15) 0.0508(4) Uani 1 1 d . . . . .
H2A H 0.7190 0.7115 0.5663 0.076 Uiso 1 1 calc GR . . . .
H2B H 0.8020 0.7041 0.6513 0.076 Uiso 1 1 calc GR . . . .
H2C H 0.7307 0.7509 0.6838 0.076 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 C9 1.3826(14) . ?
O1 C11 1.4280(16) . ?
O2 H2 0.8200 . ?
O2 C6 1.3713(14) . ?
N1 H1 0.8597 . ?
N1 C13 1.4109(15) . ?
N1 C12 1.4680(14) . ?
C9 C8 1.3770(16) . ?
C9 C10 1.3910(17) . ?
C8 H8 0.9300 . ?
C8 C7 1.3916(16) . ?
C13 C13 1.401(2) 2_656 ?
C13 C14 1.3907(16) . ?
C7 C12 1.5098(15) . ?
C7 C6 1.4002(16) . ?
C10 H10 0.9300 . ?
C10 C5 1.3885(18) . ?
C12 C12 1.551(2) 2_656 ?
C12 H12 0.9800 . ?
C6 C5 1.4063(17) . ?
C5 C4 1.5403(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.3828(19) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 C15 1.389(3) 2_656 ?
C15 H15 0.9300 . ?
C4 C3 1.5370(19) . ?
C4 C1 1.535(2) . ?
C4 C2 1.529(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C9 O1 C11 117.23(9) . . ?
C6 O2 H2 109.5 . . ?
C13 N1 H1 111.6 . . ?
C13 N1 C12 117.15(9) . . ?
C12 N1 H1 111.5 . . ?
O1 C9 C10 115.18(10) . . ?
C8 C9 O1 124.53(11) . . ?
C8 C9 C10 120.28(11) . . ?
C9 C8 H8 120.3 . . ?
C9 C8 C7 119.40(10) . . ?
C7 C8 H8 120.3 . . ?
C13 C13 N1 119.80(6) 2_656 . ?
C14 C13 N1 120.88(11) . . ?
C14 C13 C13 119.22(7) . 2_656 ?
C8 C7 C12 118.25(10) . . ?
C8 C7 C6 120.00(10) . . ?
C6 C7 C12 121.35(10) . . ?
C9 C10 H10 118.9 . . ?
C5 C10 C9 122.13(11) . . ?
C5 C10 H10 118.9 . . ?
N1 C12 C7 111.79(9) . . ?
N1 C12 C12 107.92(7) . 2_656 ?
N1 C12 H12 109.1 . . ?
C7 C12 C12 109.84(7) . 2_656 ?
C7 C12 H12 109.1 . . ?
C12 C12 H12 109.1 2_656 . ?
O2 C6 C7 120.32(10) . . ?
O2 C6 C5 118.49(10) . . ?
C7 C6 C5 121.16(11) . . ?
C10 C5 C6 117.01(11) . . ?
C10 C5 C4 121.45(11) . . ?
C6 C5 C4 121.46(11) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.01(12) . . ?
C15 C14 H14 119.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C15 C15 119.72(8) . 2_656 ?
C14 C15 H15 120.1 . . ?
C15 C15 H15 120.1 2_656 . ?
C3 C4 C5 111.22(11) . . ?
C1 C4 C5 108.85(10) . . ?
C1 C4 C3 110.02(13) . . ?
C2 C4 C5 111.36(12) . . ?
C2 C4 C3 107.15(12) . . ?
C2 C4 C1 108.19(13) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.82 1.97 2.6977(13) 147.6 .

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 C9 C8 C7 -179.72(10) . . . . ?
O1 C9 C10 C5 -179.26(10) . . . . ?
O2 C6 C5 C10 -177.61(10) . . . . ?
O2 C6 C5 C4 -0.94(16) . . . . ?
N1 C13 C14 C15 173.97(11) . . . . ?
C9 C8 C7 C12 171.16(9) . . . . ?
C9 C8 C7 C6 -1.70(16) . . . . ?
C9 C10 C5 C6 -0.53(17) . . . . ?
C9 C10 C5 C4 -177.20(11) . . . . ?
C8 C9 C10 C5 -0.30(17) . . . . ?
C8 C7 C12 N1 143.02(10) . . . . ?
C8 C7 C12 C12 -97.20(13) . . . 2_656 ?
C8 C7 C6 O2 178.68(10) . . . . ?
C8 C7 C6 C5 0.87(16) . . . . ?
C13 N1 C12 C7 169.60(9) . . . . ?
C13 N1 C12 C12 48.69(14) . . . 2_656 ?
C13 C13 C14 C15 -2.5(2) 2_656 . . . ?
C13 C14 C15 C15 0.1(2) . . . 2_656 ?
C7 C6 C5 C10 0.24(16) . . . . ?
C7 C6 C5 C4 176.91(10) . . . . ?
C10 C9 C8 C7 1.42(16) . . . . ?
C10 C5 C4 C3 -124.68(13) . . . . ?
C10 C5 C4 C1 113.94(14) . . . . ?
C10 C5 C4 C2 -5.25(17) . . . . ?
C12 N1 C13 C13 -24.78(19) . . . 2_656 ?
C12 N1 C13 C14 158.79(11) . . . . ?
C12 C7 C6 O2 6.04(16) . . . . ?
C12 C7 C6 C5 -171.77(10) . . . . ?
C6 C7 C12 N1 -44.22(14) . . . . ?
C6 C7 C12 C12 75.56(13) . . . 2_656 ?
C6 C5 C4 C3 58.81(16) . . . . ?
C6 C5 C4 C1 -62.57(16) . . . . ?
C6 C5 C4 C2 178.24(12) . . . . ?
C11 O1 C9 C8 12.86(16) . . . . ?
C11 O1 C9 C10 -168.23(10) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5 -2 0 0.0659 5.0067 -1.9941 -0.0023 -0.0316 -0.1663 -0.4874
-5 2 0 0.0729 -5.0067 1.9941 0.0023 0.0316 0.1663 0.4874
1 0 -5 0.0822 0.9953 -0.0065 -4.9990 0.1682 0.5594 -0.1160
0 0 1 0.0817 0.0011 0.0015 0.9996 -0.0265 -0.1200 0.0087
5 -4 -2 0.0898 5.0059 -3.9955 -2.0003 -0.1891 0.1111 -0.6297
-4 -5 -1 0.0540 -4.0014 -5.0009 -0.9933 -0.6427 0.3762 -0.0311
5 3 0 0.0785 5.0028 3.0019 -0.0057 0.4945 -0.2596 -0.1750
-3 5 2 0.0747 -3.0047 4.9964 1.9981 0.3658 -0.2112 0.5472
-5 -1 0 0.0729 -5.0043 -1.0035 0.0044 -0.2840 0.2222 0.2999
-5 -4 2 0.0660 -4.9997 -3.9981 2.0057 -0.6527 0.0382 0.1299
5 4 -2 0.0819 4.9997 3.9981 -2.0057 0.6527 -0.0382 -0.1299
-2 5 0 0.0609 -2.0059 4.9943 -0.0019 0.4546 -0.0119 0.4573
1 -5 0 0.0649 1.0049 -4.9951 0.0026 -0.4903 0.0526 -0.3848
-5 3 1 0.0722 -5.0063 2.9948 1.0013 0.1104 0.0276 0.5585
8 2 3 0.0846 8.0101 2.0097 2.9917 0.4171 -0.7231 -0.4288

_olex2_date_sample_data_collection 2016-02-16
_olex2_date_sample_submission    2016-02-15
_olex2_submission_original_sample_id 'KL OMe cat THF'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.837

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_mn1908
_database_code_depnum_ccdc_archive 'CCDC 1983170'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_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         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H22 N2 O4'
_chemical_oxdiff_usercomment     'Katie Lamb KL 2,6 Cry'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3701(5)
_cell_length_b                   10.2836(7)
_cell_length_c                   12.5573(7)
_cell_angle_alpha                97.383(5)
_cell_angle_beta                 104.649(6)
_cell_angle_gamma                99.610(6)
_cell_volume                     893.21(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.4420
_cell_measurement_theta_min      6.2520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0669
2 1 -2 0.0600
1 0 -1 0.0551
0 1 0 0.0464
-1 2 0 0.0756
2 0 -1 0.0725
-2 1 0 0.0959
0 -2 1 0.0728
1 0 2 0.0948
0 0 1 0.0870
0 0 -1 0.0952
0 -2 -1 0.0684
-1 0 1 0.1190
-1 0 -2 0.1021
0 1 -2 0.1021
-2 1 2 0.1079
1 -2 -1 0.0612
-1 -1 0 0.1121
0 -1 -2 0.0852
1 0 -2 0.0704

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.113
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0014 -1.0013 -0.0005 0.0420 0.0692 0.1317
1.9979 1.0009 -1.9966 0.1261 0.2413 -0.4014
0.9996 -0.0002 -0.9986 0.0841 0.1553 -0.1349
-0.0014 1.0013 0.0005 -0.0420 -0.0692 -0.1317
-1.0017 2.0022 -0.0001 -0.0406 -0.3111 -0.1329
1.9986 0.0003 -0.9975 0.0406 0.3279 -0.2653
-1.9993 1.0003 -0.0017 0.0450 -0.4145 0.1292
0.0021 -2.0020 0.9987 -0.0435 0.1559 0.2678
0.9977 0.0019 2.0003 -0.2986 0.2074 -0.1216
-0.0006 0.0007 0.9996 -0.1276 0.0174 0.0044
0.0006 -0.0007 -0.9996 0.1276 -0.0174 -0.0044
0.0033 -2.0034 -1.0006 0.2116 0.1211 0.2589
-0.9996 0.0002 0.9986 -0.0841 -0.1553 0.1349
-0.9977 -0.0019 -2.0003 0.2986 -0.2074 0.1216
-0.0001 0.9999 -1.9988 0.2131 -0.1040 -0.1405
-2.0006 1.0018 1.9976 -0.2102 -0.3798 0.1381
1.0023 -2.0029 -0.9995 0.1681 0.2938 0.1285
-0.9976 -1.0018 -0.0015 0.0855 -0.1034 0.2621
0.0026 -1.0028 -1.9997 0.2972 0.0345 0.1228
1.0003 -0.0009 -1.9982 0.2116 0.1379 -0.1393

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5380
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.036
_diffrn_reflns_theta_max         67.036
_diffrn_reflns_theta_min         3.698
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00 -32.00   1.00    1.00    --    0.00 -57.00  60.00   29
  2  ω    -20.00  21.00   1.00    1.00    --    0.00 -57.00  60.00   41
  3  ω    -16.00  18.00   1.00    1.00    --    0.00  57.00-150.00   34
  4  ω     30.00  56.00   1.00    1.00    --    0.00  57.00-150.00   26
  5  ω     32.00  95.00   1.00    1.00    --   54.00-125.00-120.00   63
  6  ω     26.00  80.00   1.00    1.00    --   54.00-125.00  90.00   54
  7  ω    -11.00 119.00   1.00    1.00    --   54.00   0.00 -90.00  130
  8  ω     95.00 120.00   1.00    1.00    --   54.00  57.00-120.00   25
  9  ω     -6.00  59.00   1.00    1.00    --   54.00 -37.00  60.00   65
 10  ω    -15.00  69.00   1.00    1.00    --   54.00 -77.00 -60.00   84
 11  ω     28.00  53.00   1.00    1.00    --   54.00-125.00 -60.00   25
 12  ω     94.00 168.00   1.00    1.00    --  108.00  63.00  30.00   74
 13  ω     42.00 123.00   1.00    1.00    --  108.00 -50.00-180.00   81
 14  ω     94.00 145.00   1.00    1.00    --  108.00 -91.00  30.00   51
 15  ω     36.00 146.00   1.00    1.00    --  108.00 -91.00 -30.00  110
 16  ω     89.00 178.00   1.00    1.00    --  108.00  37.00  90.00   89
 17  ω     39.00  72.00   1.00    1.00    --  108.00 -50.00  60.00   33
 18  ω     78.00 104.00   1.00    1.00    --  108.00-111.00-120.00   26
 19  ω     57.00 146.00   1.00    1.00    --  108.00 178.00 -60.00   89
 20  ω     38.00  93.00   1.00    1.00    --  108.00 -50.00 -30.00   55
 21  ω     97.00 175.00   1.00    1.00    --  108.00  63.00 120.00   78
 22  ω     89.00 119.00   1.00    1.00    --  108.00 -50.00  60.00   30
 23  ω     64.00 108.00   1.00    1.00    --  108.00-111.00 -60.00   44
 24  ω     98.00 145.00   1.00    1.00    --  108.00  77.00 150.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0433834000
_diffrn_orient_matrix_UB_12      -0.0419811000
_diffrn_orient_matrix_UB_13      -0.1276089000
_diffrn_orient_matrix_UB_21      0.1728379000
_diffrn_orient_matrix_UB_22      -0.0689298000
_diffrn_orient_matrix_UB_23      0.0175436000
_diffrn_orient_matrix_UB_31      -0.1305042000
_diffrn_orient_matrix_UB_32      -0.1316657000
_diffrn_orient_matrix_UB_33      0.0044490000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2772
_reflns_number_total             3183
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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         0.226
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.032
_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)+(0.0436P)²+0.2669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0875
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.69526(18) 0.47666(14) 0.72646(11) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.6679(2) 0.38288(14) 0.79485(12) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.619(2) 0.2909(17) 0.7611(13) 0.024(4) Uiso 1 1 d . . . . .
C3 C 0.7095(2) 0.42573(15) 0.90845(12) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.690(3) 0.3599(18) 0.9581(15) 0.035(5) Uiso 1 1 d . . . . .
C4 C 0.7815(2) 0.56010(15) 0.95635(12) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.814(2) 0.5896(16) 1.0349(15) 0.028(4) Uiso 1 1 d . . . . .
C5 C 0.81113(18) 0.65313(13) 0.88809(11) 0.0152(3) Uani 1 1 d . . . . .
C6 C 0.76654(18) 0.61350(13) 0.77147(11) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.79189(18) 0.71462(13) 0.69562(11) 0.0134(3) Uani 1 1 d . . . . .
H7 H 0.873(2) 0.8019(15) 0.7410(12) 0.015(4) Uiso 1 1 d . . . . .
C8 C 0.89804(18) 0.73664(13) 0.52781(11) 0.0149(3) Uani 1 1 d . . . . .
C9 C 1.0424(2) 0.72992(13) 0.47512(11) 0.0174(3) Uani 1 1 d . . . . .
H9 H 1.133(2) 0.6733(16) 0.4989(13) 0.022(4) Uiso 1 1 d . . . . .
C10 C 1.0536(2) 0.80005(14) 0.38924(11) 0.0191(3) Uani 1 1 d . . . . .
H10 H 1.155(2) 0.7948(15) 0.3519(13) 0.019(4) Uiso 1 1 d . . . . .
C11 C 0.9201(2) 0.87852(14) 0.35547(12) 0.0197(3) Uani 1 1 d . . . . .
H11 H 0.924(2) 0.9288(16) 0.2950(13) 0.022(4) Uiso 1 1 d . . . . .
C12 C 0.7777(2) 0.88665(14) 0.40872(11) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.688(2) 0.9415(16) 0.3877(13) 0.023(4) Uiso 1 1 d . . . . .
C13 C 0.76541(18) 0.81664(13) 0.49524(11) 0.0146(3) Uani 1 1 d . . . . .
C14 C 0.59599(18) 0.74103(13) 0.63210(11) 0.0136(3) Uani 1 1 d . . . . .
H14 H 0.517(2) 0.6537(15) 0.5901(12) 0.011(3) Uiso 1 1 d . . . . .
C15 C 0.49997(18) 0.80260(13) 0.71363(11) 0.0141(3) Uani 1 1 d . . . . .
C16 C 0.36265(18) 0.72171(13) 0.74961(11) 0.0157(3) Uani 1 1 d . . . . .
C17 C 0.28268(19) 0.77412(15) 0.83047(11) 0.0196(3) Uani 1 1 d . . . . .
H17 H 0.186(2) 0.7169(16) 0.8544(13) 0.023(4) Uiso 1 1 d . . . . .
C18 C 0.3364(2) 0.90950(15) 0.87459(12) 0.0215(3) Uani 1 1 d . . . . .
H18 H 0.280(2) 0.9443(16) 0.9309(14) 0.024(4) Uiso 1 1 d . . . . .
C19 C 0.4686(2) 0.99276(15) 0.83975(12) 0.0212(3) Uani 1 1 d . . . . .
H19 H 0.506(2) 1.0890(17) 0.8692(14) 0.027(4) Uiso 1 1 d . . . . .
C20 C 0.55098(19) 0.93951(13) 0.76058(11) 0.0163(3) Uani 1 1 d . . . . .
C21 C 0.9406(3) 0.82874(17) 1.04748(12) 0.0271(4) Uani 1 1 d . . . . .
H21A H 1.031(3) 0.7773(18) 1.0836(15) 0.034(5) Uiso 1 1 d . . . . .
H21B H 0.828(3) 0.8161(18) 1.0770(15) 0.037(5) Uiso 1 1 d . . . . .
H21C H 0.995(3) 0.926(2) 1.0609(15) 0.039(5) Uiso 1 1 d . . . . .
C22 C 0.2543(2) 0.49442(15) 0.76368(13) 0.0221(3) Uani 1 1 d . . . . .
H22A H 0.255(2) 0.4068(17) 0.7246(14) 0.023(4) Uiso 1 1 d . . . . .
H22B H 0.350(2) 0.5159(17) 0.8372(15) 0.028(4) Uiso 1 1 d . . . . .
H22C H 0.127(3) 0.4955(17) 0.7727(14) 0.028(4) Uiso 1 1 d . . . . .
N1 N 0.88042(16) 0.65894(11) 0.61133(9) 0.0150(3) Uani 1 1 d . . . . .
H1 H 0.993(3) 0.6388(17) 0.6441(14) 0.025(4) Uiso 1 1 d . . . . .
N2 N 0.62706(17) 0.83408(11) 0.55430(9) 0.0159(3) Uani 1 1 d . . . . .
H2A H 0.518(3) 0.8341(17) 0.5060(15) 0.027(4) Uiso 1 1 d . . . . .
O1 O 0.64866(14) 0.43056(10) 0.61408(8) 0.0200(2) Uani 1 1 d . . . . .
H1A H 0.715(3) 0.496(2) 0.5854(17) 0.046(6) Uiso 1 1 d . . . . .
O2 O 0.88551(14) 0.78681(9) 0.92862(7) 0.0189(2) Uani 1 1 d . . . . .
O3 O 0.30735(13) 0.58983(9) 0.69727(8) 0.0197(2) Uani 1 1 d . . . . .
O4 O 0.68401(14) 1.02536(9) 0.73027(9) 0.0212(2) Uani 1 1 d . . . . .
H4A H 0.694(3) 0.980(2) 0.6632(19) 0.053(6) Uiso 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
C1 C2 1.3941(19) . ?
C1 C6 1.4051(19) . ?
C1 O1 1.3648(16) . ?
C2 C3 1.377(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.3904(19) . ?
C5 C6 1.4061(18) . ?
C5 O2 1.3700(16) . ?
C6 C7 1.5176(17) . ?
C7 C14 1.5488(18) . ?
C7 N1 1.4806(16) . ?
C8 C9 1.3938(19) . ?
C8 C13 1.3973(19) . ?
C8 N1 1.4159(16) . ?
C9 C10 1.3838(19) . ?
C10 C11 1.394(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.3913(18) . ?
C13 N2 1.4252(17) . ?
C14 C15 1.5164(18) . ?
C14 N2 1.4841(16) . ?
C15 C16 1.4025(18) . ?
C15 C20 1.4032(19) . ?
C16 C17 1.3917(19) . ?
C16 O3 1.3741(16) . ?
C17 C18 1.382(2) . ?
C18 C19 1.381(2) . ?
C19 C20 1.391(2) . ?
C20 O4 1.3680(16) . ?
C21 O2 1.4311(17) . ?
C22 O3 1.4346(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.25(13) . . ?
O1 C1 C2 117.43(12) . . ?
O1 C1 C6 121.32(12) . . ?
C3 C2 C1 119.22(13) . . ?
C2 C3 C4 121.30(13) . . ?
C3 C4 C5 119.34(13) . . ?
C4 C5 C6 120.96(12) . . ?
O2 C5 C4 123.11(12) . . ?
O2 C5 C6 115.93(11) . . ?
C1 C6 C5 117.92(12) . . ?
C1 C6 C7 120.57(11) . . ?
C5 C6 C7 121.51(11) . . ?
C6 C7 C14 111.05(10) . . ?
N1 C7 C6 108.63(10) . . ?
N1 C7 C14 107.71(10) . . ?
C9 C8 C13 119.89(12) . . ?
C9 C8 N1 120.41(12) . . ?
C13 C8 N1 119.66(12) . . ?
C10 C9 C8 120.55(13) . . ?
C9 C10 C11 119.74(13) . . ?
C12 C11 C10 119.80(13) . . ?
C11 C12 C13 120.86(13) . . ?
C8 C13 N2 120.78(12) . . ?
C12 C13 C8 119.15(12) . . ?
C12 C13 N2 119.94(12) . . ?
C15 C14 C7 110.48(10) . . ?
N2 C14 C7 109.06(10) . . ?
N2 C14 C15 109.42(10) . . ?
C16 C15 C14 120.40(12) . . ?
C16 C15 C20 117.41(12) . . ?
C20 C15 C14 122.09(12) . . ?
C17 C16 C15 121.52(13) . . ?
O3 C16 C15 116.00(12) . . ?
O3 C16 C17 122.43(12) . . ?
C18 C17 C16 119.33(13) . . ?
C19 C18 C17 120.81(13) . . ?
C18 C19 C20 119.67(13) . . ?
C19 C20 C15 121.23(12) . . ?
O4 C20 C15 121.17(12) . . ?
O4 C20 C19 117.60(12) . . ?
C8 N1 C7 115.48(10) . . ?
C13 N2 C14 118.03(10) . . ?
C5 O2 C21 117.04(11) . . ?
C16 O3 C22 116.19(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N1 0.93(2) 1.84(2) 2.6731(15) 148.3(18) . yes
O4 H4A N2 0.94(2) 1.80(2) 2.6583(15) 150.9(19) . yes

_olex2_date_sample_data_collection 2019-09-11
_olex2_date_sample_submission    2019-08-21
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id 'KL 2,6 cry'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.776
####################################################################### 
# 
# 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_mn1909
_database_code_depnum_ccdc_archive 'CCDC 1983172'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-09-23
_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         'C28 H34 N2 O2'
_chemical_formula_sum            'C28 H34 N2 O2'
_chemical_formula_weight         430.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H34 N2 O2'
_chemical_oxdiff_usercomment     'Katie Lamb KL 4-T Cry'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   16.29085(17)
_cell_length_b                   20.8151(2)
_cell_length_c                   23.2057(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.2865(12)
_cell_angle_gamma                90
_cell_volume                     7590.57(15)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    10102
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      69.8280
_cell_measurement_theta_min      4.3720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0279
0 0 -1 0.0165
0 -1 0 0.0653
0 1 0 0.0264
-1 0 0 0.0897
-2 -2 1 0.1022
1 0 2 0.0183

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.044
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.0000 1.0000 -0.0108 0.0677 -0.0051
0.0000 -0.0000 -1.0000 0.0108 -0.0677 0.0051
-0.0000 -1.0000 -0.0000 0.0631 0.0128 0.0365
0.0000 1.0000 0.0000 -0.0631 -0.0128 -0.0365
-1.0000 0.0000 0.0000 -0.0431 -0.0267 0.0839
-2.0000 -1.9999 0.9999 0.0291 0.0399 0.2357
0.9999 -0.0000 2.0000 0.0214 0.1622 -0.0942

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29179
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.524
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -39.00   1.00    6.25    --    0.00 146.00 -55.00   27
  2  ω    -51.00 -22.00   1.00    6.25    --    0.00 125.00 138.00   29
  3  ω      6.00  60.00   1.00    6.25    --    0.00  57.00 -30.00   54
  4  ω      1.00  65.00   1.00   25.00    --   54.00 -99.00  60.00   64
  5  ω     45.00 120.00   1.00   25.00    --   54.00  37.00 -60.00   75
  6  ω     33.00  96.00   1.00   25.00    --   54.00 -99.00-180.00   63
  7  ω     24.00  79.00   1.00   25.00    --   54.00-125.00 150.00   55
  8  ω     17.00  74.00   1.00   25.00    --   54.00 -57.00 -90.00   57
  9  ω     58.00 125.00   1.00   25.00    --  108.00 -37.00-120.00   67
 10  ω     88.00 176.00   1.00   25.00    --  108.00  63.00-150.00   88
 11  ω     78.00 173.00   1.00   25.00    --  108.00  77.00 -90.00   95
 12  ω     38.00 134.00   1.00   25.00    --  108.00 -77.00 150.00   96
 13  ω     80.00 113.00   1.00   25.00    --  108.00-111.00 -90.00   33
 14  ω     78.00 112.00   1.00   25.00    --  108.00  77.00-180.00   34
 15  ω     48.00 136.00   1.00   25.00    --  108.00 -77.00 -30.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0431064000
_diffrn_orient_matrix_UB_12      -0.0630952000
_diffrn_orient_matrix_UB_13      -0.0108294000
_diffrn_orient_matrix_UB_21      0.0266774000
_diffrn_orient_matrix_UB_22      -0.0127634000
_diffrn_orient_matrix_UB_23      0.0677487000
_diffrn_orient_matrix_UB_31      -0.0839181000
_diffrn_orient_matrix_UB_32      -0.0365114000
_diffrn_orient_matrix_UB_33      -0.0051269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10818
_reflns_number_total             13536
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     926
_refine_ls_number_reflns         13536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.047
_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)+(0.0590P)²+4.8015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1379
_refine_special_details          
;
The crystal contained highly disordered solvents of crystallisation 
for which a satisfactory discrete atom model could not be obtained.
Therefore a solvent mask was used which revealed two solvent voids
per unit cell with a predicted electron count of 38 which corresponds
approximately to one dichloromethane.

Acidic hydrogens were located by difference map and allowed to refine
apart from H3b and H4b.  For these two hydrogens, refinement gave
unrealistic O-H bond lengths so hydrogens on O3 and O4 were placed
using a riding model.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.031) H3(0.032) H5(0.03) H7(0.028) H9(0.042) H10(0.054)
 H11(0.062) H12(0.052) H14(0.03) H16(0.03) H18(0.045) H19(0.046) H22A(0.058)
 H22B(0.058) H22C(0.058) H23A(0.051) H23B(0.051) H23C(0.051) H24A(0.06)
 H24B(0.06) H24C(0.06) H26A(0.088) H26B(0.088) H26C(0.088) H27A(0.075)
 H27B(0.075) H27C(0.075) H28A(0.061) H28B(0.061) H28C(0.061) H30(0.038)
 H31(0.04) H33(0.034) H35(0.033) H37(0.047) H38(0.054) H39(0.054) H40(0.047)
 H42(0.034) H44(0.031) H46(0.045) H47(0.049) H50A(0.065) H50B(0.065)
 H50C(0.065) H51A(0.096) H51B(0.096) H51C(0.096) H52A(0.081) H52B(0.081)
 H52C(0.081) H54A(0.064) H54B(0.064) H54C(0.064) H55A(0.063) H55B(0.063)
 H55C(0.063) H56A(0.064) H56B(0.064) H56C(0.064) H3B(0.05) H4A(0.068)
 H58(0.034) H59(0.035) H61(0.029) H63(0.027) H65(0.039) H66(0.045) H67(0.047)
 H68(0.039) H70(0.027) H72(0.027) H74(0.034) H75(0.035) H78A(0.072) H78B(0.072)
 H78C(0.072) H79A(0.064) H79B(0.064) H79C(0.064) H80A(0.071) H80B(0.071)
 H80C(0.071) H82A(0.069) H82B(0.069) H82C(0.069) H83A(0.057) H83B(0.057)
 H83C(0.057) H84A(0.072) H84B(0.072) H84C(0.072)
 Fixed X: H2(0.445905) H3(0.549986) H5(0.461246) H7(0.346619) H9(0.295623)
 H10(0.192143) H11(0.086005) H12(0.080776) H14(0.219931) H16(0.25322)
 H18(0.303971) H19(0.289968) H22A(0.675806) H22B(0.691654) H22C(0.617921)
 H23A(0.602024) H23B(0.682259) H23C(0.666052) H24A(0.511804) H24B(0.588616)
 H24C(0.50969) H26A(0.165982) H26B(0.226804) H26C(0.232759) H27A(0.313761)
 H27B(0.279753) H27C(0.216582) H28A(0.388342) H28B(0.382146) H28C(0.418383)
 H30(1.061158) H31(1.116175) H33(1.100093) H35(1.048133) H37(1.077057)
 H38(1.002881) H39(0.880952) H40(0.835642) H42(0.901521) H44(0.861578)
 H46(0.850586) H47(0.897644) H50A(1.266274) H50B(1.278472) H50C(1.232618)
 H51A(1.117698) H51B(1.209828) H51C(1.194038) H52A(1.121439) H52B(1.08856)
 H52C(1.04253) H54A(0.889762) H54B(0.863173) H54C(0.937546) H55A(0.787819)
 H55B(0.770227) H55C(0.86357) H56A(0.736763) H56B(0.691967) H56C(0.712291)
 H3B(1.009121) H4A(0.935426) H58(0.203193) H59(0.162697) H61(0.298521)
 H63(0.370918) H65(0.325305) H66(0.426063) H67(0.568704) H68(0.609856)
 H70(0.455905) H72(0.464533) H74(0.539217) H75(0.551554) H78A(0.087477)
 H78B(0.121809) H78C(0.16807) H79A(0.178451) H79B(0.124388) H79C(0.09504)
 H80A(0.305261) H80B(0.2534) H80C(0.306781) H82A(0.361691) H82B(0.393475)
 H82C(0.384558) H83A(0.534694) H83B(0.542309) H83C(0.607603) H84A(0.572385)
 H84B(0.505687) H84C(0.478063)
 Fixed Y: H2(0.531408) H3(0.501604) H5(0.32204) H7(0.289706) H9(0.269063)
 H10(0.195759) H11(0.167564) H12(0.214162) H14(0.388588) H16(0.449627)
 H18(0.367083) H19(0.267396) H22A(0.455088) H22B(0.422232) H22C(0.472353)
 H23A(0.295902) H23B(0.31566) H23C(0.346784) H24A(0.391726) H24B(0.344793)
 H24C(0.322702) H26A(0.48525) H26B(0.531449) H26C(0.457005) H27A(0.538455)
 H27B(0.5813) H27C(0.538295) H28A(0.459015) H28B(0.533688) H28C(0.49099)
 H30(0.399473) H31(0.498484) H33(0.555969) H35(0.489783) H37(0.299419)
 H38(0.263948) H39(0.318127) H40(0.407081) H42(0.426152) H44(0.481033)
 H46(0.671758) H47(0.678895) H50A(0.651448) H50B(0.576826) H50C(0.607074)
 H51A(0.607882) H51B(0.580129) H51C(0.654234) H52A(0.698824) H52B(0.653299)
 H52C(0.654386) H54A(0.650873) H54B(0.606265) H54C(0.58576) H55A(0.504113)
 H55B(0.481387) H55C(0.482561) H56A(0.649638) H56B(0.583661) H56C(0.604582)
 H3B(0.355203) H4A(0.555701) H58(0.82769) H59(0.760789) H61(0.866078)
 H63(0.960639) H65(1.134203) H66(1.214876) H67(1.190866) H68(1.086709)
 H70(0.925267) H72(0.812312) H74(0.717582) H75(0.813255) H78A(0.726232)
 H78B(0.684237) H78C(0.682945) H79A(0.841665) H79B(0.781665) H79C(0.824594)
 H80A(0.711822) H80B(0.710404) H80C(0.771365) H82A(0.682182) H82B(0.6452)
 H82C(0.720195) H83A(0.727567) H83B(0.652532) H83C(0.695588) H84A(0.634801)
 H84B(0.593859) H84C(0.630562)
 Fixed Z: H2(0.232916) H3(0.316895) H5(0.299526) H7(0.222908) H9(0.041878)
 H10(-0.004529) H11(0.040521) H12(0.129018) H14(0.202666) H16(0.292388)
 H18(0.453371) H19(0.409715) H22A(0.370632) H22B(0.433399) H22C(0.412714)
 H23A(0.33622) H23B(0.38709) H23C(0.323561) H24A(0.430623) H24B(0.454106)
 H24C(0.403242) H26A(0.419667) H26B(0.464837) H26C(0.47535) H27A(0.340611)
 H27B(0.384878) H27C(0.337891) H28A(0.47931) H28B(0.470428) H28C(0.427187)
 H30(0.098406) H31(0.08321) H33(0.243747) H35(0.30814) H37(0.381622)
 H38(0.447943) H39(0.454559) H40(0.39608) H42(0.234968) H44(0.144758)
 H46(0.134687) H47(0.236845) H50A(0.198344) H50B(0.196689) H50C(0.241713)
 H51A(0.063969) H51B(0.088207) H51C(0.090852) H52A(0.16274) H52B(0.20565)
 H52C(0.137204) H54A(0.044942) H54B(-0.011346) H54C(0.043516) H55A(-0.007041)
 H55B(0.052998) H55C(0.046459) H56A(0.051672) H56B(0.055267) H56C(-0.004392)
 H3B(0.221793) H4A(0.330044) H58(0.225657) H59(0.292206) H61(0.428037)
 H63(0.41372) H65(0.316402) H66(0.329581) H67(0.369203) H68(0.39605)
 H70(0.324346) H72(0.32935) H74(0.484281) H75(0.535293) H78A(0.356378)
 H78B(0.413764) H78C(0.362485) H79A(0.465821) H79B(0.473895) H79C(0.416636)
 H80A(0.438972) H80B(0.487069) H80C(0.480608) H82A(0.352508) H82B(0.303618)
 H82C(0.300514) H83A(0.295575) H83B(0.299662) H83C(0.345171) H84A(0.42757)
 H84B(0.380946) H84C(0.43178)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.39143(11) 0.44411(9) 0.21489(8) 0.0239(4) Uani 1 1 d . . . . .
C2 C 0.44913(12) 0.48901(9) 0.24595(9) 0.0257(4) Uani 1 1 d . . . . .
H2 H 0.445905 0.531408 0.232916 0.031 Uiso 1 1 calc R . . . .
C3 C 0.51177(12) 0.47088(9) 0.29651(9) 0.0267(4) Uani 1 1 d . . . . .
H3 H 0.549986 0.501604 0.316895 0.032 Uiso 1 1 calc R . . . .
C4 C 0.51883(11) 0.40795(10) 0.31745(8) 0.0254(4) Uani 1 1 d . . . . .
C5 C 0.45858(12) 0.36428(9) 0.28609(9) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.461246 0.322040 0.299526 0.030 Uiso 1 1 calc R . . . .
C6 C 0.39473(11) 0.38097(9) 0.23567(8) 0.0233(4) Uani 1 1 d . . . . .
C7 C 0.32756(11) 0.33252(9) 0.20746(8) 0.0236(4) Uani 1 1 d . . . . .
H7 H 0.346619 0.289706 0.222908 0.028 Uiso 1 1 calc R . . . .
C8 C 0.24941(12) 0.28645(9) 0.11290(9) 0.0275(4) Uani 1 1 d . . . . .
C9 C 0.25225(13) 0.25830(11) 0.05935(10) 0.0348(5) Uani 1 1 d . . . . .
H9 H 0.295623 0.269063 0.041878 0.042 Uiso 1 1 calc R . . . .
C10 C 0.19071(15) 0.21417(12) 0.03171(11) 0.0448(6) Uani 1 1 d . . . . .
H10 H 0.192143 0.195759 -0.004529 0.054 Uiso 1 1 calc R . . . .
C11 C 0.12693(16) 0.19766(13) 0.05855(12) 0.0518(7) Uani 1 1 d . . . . .
H11 H 0.086005 0.167564 0.040521 0.062 Uiso 1 1 calc R . . . .
C12 C 0.12394(15) 0.22552(12) 0.11155(11) 0.0434(6) Uani 1 1 d . . . . .
H12 H 0.080776 0.214162 0.129018 0.052 Uiso 1 1 calc R . . . .
C13 C 0.18460(12) 0.27054(10) 0.13954(9) 0.0305(4) Uani 1 1 d . . . . .
C14 C 0.24222(11) 0.34786(9) 0.22167(9) 0.0246(4) Uani 1 1 d . . . . .
H14 H 0.219931 0.388588 0.202666 0.030 Uiso 1 1 calc R . . . .
C15 C 0.25345(11) 0.35291(9) 0.28832(9) 0.0253(4) Uani 1 1 d . . . . .
C16 C 0.26091(11) 0.41295(9) 0.31609(9) 0.0253(4) Uani 1 1 d . . . . .
H16 H 0.253220 0.449627 0.292388 0.030 Uiso 1 1 calc R . . . .
C17 C 0.27937(12) 0.42009(10) 0.37776(9) 0.0297(4) Uani 1 1 d . . . . .
C18 C 0.29067(14) 0.36391(11) 0.41196(10) 0.0373(5) Uani 1 1 d . . . . .
H18 H 0.303971 0.367083 0.453371 0.045 Uiso 1 1 calc R . . . .
C19 C 0.28262(14) 0.30398(11) 0.38590(10) 0.0380(5) Uani 1 1 d . . . . .
H19 H 0.289968 0.267396 0.409715 0.046 Uiso 1 1 calc R . . . .
C20 C 0.26352(13) 0.29801(10) 0.32410(10) 0.0309(4) Uani 1 1 d . . . . .
C21 C 0.58810(12) 0.38463(10) 0.37206(9) 0.0297(4) Uani 1 1 d . . . . .
C22 C 0.64900(14) 0.43856(12) 0.39976(10) 0.0389(5) Uani 1 1 d . . . . .
H22A H 0.675806 0.455088 0.370632 0.058 Uiso 1 1 calc GR . . . .
H22B H 0.691654 0.422232 0.433399 0.058 Uiso 1 1 calc GR . . . .
H22C H 0.617921 0.472353 0.412714 0.058 Uiso 1 1 calc GR . . . .
C23 C 0.63940(13) 0.33070(10) 0.35295(10) 0.0338(5) Uani 1 1 d . . . . .
H23A H 0.602024 0.295902 0.336220 0.051 Uiso 1 1 calc GR . . . .
H23B H 0.682259 0.315660 0.387090 0.051 Uiso 1 1 calc GR . . . .
H23C H 0.666052 0.346784 0.323561 0.051 Uiso 1 1 calc GR . . . .
C24 C 0.54551(14) 0.35848(12) 0.41951(10) 0.0403(5) Uani 1 1 d . . . . .
H24A H 0.511804 0.391726 0.430623 0.060 Uiso 1 1 calc GR . . . .
H24B H 0.588616 0.344793 0.454106 0.060 Uiso 1 1 calc GR . . . .
H24C H 0.509690 0.322702 0.403242 0.060 Uiso 1 1 calc GR . . . .
C25 C 0.28777(14) 0.48558(11) 0.40897(10) 0.0353(5) Uani 1 1 d . . . . .
C26 C 0.22219(17) 0.49026(15) 0.44564(13) 0.0590(8) Uani 1 1 d . . . . .
H26A H 0.165982 0.485250 0.419667 0.088 Uiso 1 1 calc GR . . . .
H26B H 0.226804 0.531449 0.464837 0.088 Uiso 1 1 calc GR . . . .
H26C H 0.232759 0.457005 0.475350 0.088 Uiso 1 1 calc GR . . . .
C27 C 0.27309(18) 0.54111(11) 0.36386(11) 0.0503(6) Uani 1 1 d . . . . .
H27A H 0.313761 0.538455 0.340611 0.075 Uiso 1 1 calc GR . . . .
H27B H 0.279753 0.581300 0.384878 0.075 Uiso 1 1 calc GR . . . .
H27C H 0.216582 0.538295 0.337891 0.075 Uiso 1 1 calc GR . . . .
C28 C 0.37753(14) 0.49301(12) 0.45033(10) 0.0410(5) Uani 1 1 d . . . . .
H28A H 0.388342 0.459015 0.479310 0.061 Uiso 1 1 calc GR . . . .
H28B H 0.382146 0.533688 0.470428 0.061 Uiso 1 1 calc GR . . . .
H28C H 0.418383 0.490990 0.427187 0.061 Uiso 1 1 calc GR . . . .
N1 N 0.31211(10) 0.33234(8) 0.14189(7) 0.0263(4) Uani 1 1 d . . . . .
H1 H 0.3622(15) 0.3245(11) 0.1320(10) 0.035(6) Uiso 1 1 d . . . . .
N2 N 0.18269(11) 0.29545(8) 0.19585(8) 0.0291(4) Uani 1 1 d . . . . .
H2A H 0.1355(15) 0.3075(11) 0.1987(10) 0.029(6) Uiso 1 1 d . . . . .
O1 O 0.33243(8) 0.46311(7) 0.16325(6) 0.0288(3) Uani 1 1 d . . . . .
H1A H 0.3098(17) 0.4303(13) 0.1471(12) 0.049(8) Uiso 1 1 d . . . . .
O2 O 0.25711(11) 0.23811(7) 0.30043(8) 0.0397(4) Uani 1 1 d . . . . .
H2B H 0.2300(19) 0.2415(14) 0.2641(14) 0.060(9) Uiso 1 1 d . . . . .
C29 C 1.04725(11) 0.41842(10) 0.18050(9) 0.0277(4) Uani 1 1 d . . . . .
C30 C 1.06895(12) 0.43087(10) 0.12786(10) 0.0314(5) Uani 1 1 d . . . . .
H30 H 1.061158 0.399473 0.098406 0.038 Uiso 1 1 calc R . . . .
C31 C 1.10249(13) 0.49048(10) 0.11900(10) 0.0331(5) Uani 1 1 d . . . . .
H31 H 1.116175 0.498484 0.083210 0.040 Uiso 1 1 calc R . . . .
C32 C 1.11602(12) 0.53831(10) 0.16227(9) 0.0299(4) Uani 1 1 d . . . . .
C33 C 1.09248(12) 0.52450(10) 0.21436(9) 0.0286(4) Uani 1 1 d . . . . .
H33 H 1.100093 0.555969 0.243747 0.034 Uiso 1 1 calc R . . . .
C34 C 1.05792(11) 0.46547(10) 0.22448(9) 0.0272(4) Uani 1 1 d . . . . .
C35 C 1.02374(12) 0.45691(10) 0.27830(9) 0.0278(4) Uani 1 1 d . . . . .
H35 H 1.048133 0.489783 0.308140 0.033 Uiso 1 1 calc R . . . .
C36 C 1.00032(12) 0.37417(10) 0.34793(9) 0.0312(4) Uani 1 1 d . . . . .
C37 C 1.02814(15) 0.32097(11) 0.38419(10) 0.0394(5) Uani 1 1 d . . . . .
H37 H 1.077057 0.299419 0.381622 0.047 Uiso 1 1 calc R . . . .
C38 C 0.98395(16) 0.29967(12) 0.42407(11) 0.0454(6) Uani 1 1 d . . . . .
H38 H 1.002881 0.263948 0.447943 0.054 Uiso 1 1 calc R . . . .
C39 C 0.91117(15) 0.33214(13) 0.42807(10) 0.0449(6) Uani 1 1 d . . . . .
H39 H 0.880952 0.318127 0.454559 0.054 Uiso 1 1 calc R . . . .
C40 C 0.88388(14) 0.38514(12) 0.39269(10) 0.0395(5) Uani 1 1 d . . . . .
H40 H 0.835642 0.407081 0.396080 0.047 Uiso 1 1 calc R . . . .
C41 C 0.92713(13) 0.40653(11) 0.35190(9) 0.0321(5) Uani 1 1 d . . . . .
C42 C 0.92557(12) 0.46302(10) 0.26002(9) 0.0287(4) Uani 1 1 d . . . . .
H42 H 0.901521 0.426152 0.234968 0.034 Uiso 1 1 calc R . . . .
C43 C 0.89736(12) 0.52342(10) 0.22536(9) 0.0287(4) Uani 1 1 d . . . . .
C44 C 0.86867(11) 0.52108(10) 0.16317(9) 0.0262(4) Uani 1 1 d . . . . .
H44 H 0.861578 0.481033 0.144758 0.031 Uiso 1 1 calc R . . . .
C45 C 0.85021(12) 0.57523(10) 0.12744(9) 0.0306(4) Uani 1 1 d . . . . .
C46 C 0.86211(14) 0.63421(11) 0.15709(10) 0.0376(5) Uani 1 1 d . . . . .
H46 H 0.850586 0.671758 0.134687 0.045 Uiso 1 1 calc R . . . .
C47 C 0.89042(14) 0.63876(11) 0.21859(11) 0.0404(5) Uani 1 1 d . . . . .
H47 H 0.897644 0.678895 0.236845 0.049 Uiso 1 1 calc R . . . .
C48 C 0.90803(13) 0.58357(11) 0.25306(10) 0.0344(5) Uani 1 1 d . . . . .
C49 C 1.15555(13) 0.60457(11) 0.15566(10) 0.0345(5) Uani 1 1 d . . . . .
C50 C 1.24121(14) 0.61054(12) 0.20246(11) 0.0436(6) Uani 1 1 d . . . . .
H50A H 1.266274 0.651448 0.198344 0.065 Uiso 1 1 calc GR . . . .
H50B H 1.278472 0.576826 0.196689 0.065 Uiso 1 1 calc GR . . . .
H50C H 1.232618 0.607074 0.241713 0.065 Uiso 1 1 calc GR . . . .
C51 C 1.1707(2) 0.61243(14) 0.09396(12) 0.0638(8) Uani 1 1 d . . . . .
H51A H 1.117698 0.607882 0.063969 0.096 Uiso 1 1 calc GR . . . .
H51B H 1.209828 0.580129 0.088207 0.096 Uiso 1 1 calc GR . . . .
H51C H 1.194038 0.654234 0.090852 0.096 Uiso 1 1 calc GR . . . .
C52 C 1.09654(16) 0.65771(12) 0.16630(14) 0.0538(7) Uani 1 1 d . . . . .
H52A H 1.121439 0.698824 0.162740 0.081 Uiso 1 1 calc GR . . . .
H52B H 1.088560 0.653299 0.205650 0.081 Uiso 1 1 calc GR . . . .
H52C H 1.042530 0.654386 0.137204 0.081 Uiso 1 1 calc GR . . . .
C53 C 0.81965(13) 0.57273(10) 0.05878(9) 0.0312(4) Uani 1 1 d . . . . .
C54 C 0.88349(15) 0.60711(12) 0.03142(11) 0.0428(6) Uani 1 1 d . . . . .
H54A H 0.889762 0.650873 0.044942 0.064 Uiso 1 1 calc GR . . . .
H54B H 0.863173 0.606265 -0.011346 0.064 Uiso 1 1 calc GR . . . .
H54C H 0.937546 0.585760 0.043516 0.064 Uiso 1 1 calc GR . . . .
C55 C 0.80936(16) 0.50381(11) 0.03566(10) 0.0421(5) Uani 1 1 d . . . . .
H55A H 0.787819 0.504113 -0.007041 0.063 Uiso 1 1 calc GR . . . .
H55B H 0.770227 0.481387 0.052998 0.063 Uiso 1 1 calc GR . . . .
H55C H 0.863570 0.482561 0.046459 0.063 Uiso 1 1 calc GR . . . .
C56 C 0.73186(14) 0.60578(12) 0.03840(11) 0.0424(5) Uani 1 1 d . . . . .
H56A H 0.736763 0.649638 0.051672 0.064 Uiso 1 1 calc GR . . . .
H56B H 0.691967 0.583661 0.055267 0.064 Uiso 1 1 calc GR . . . .
H56C H 0.712291 0.604582 -0.004392 0.064 Uiso 1 1 calc GR . . . .
N3 N 1.04410(11) 0.39262(9) 0.30488(8) 0.0317(4) Uani 1 1 d . . . . .
H3A H 1.1024(16) 0.3881(11) 0.3182(11) 0.041(7) Uiso 1 1 d . . . . .
N4 N 0.89746(11) 0.46054(9) 0.31490(8) 0.0319(4) Uani 1 1 d . . . . .
H4 H 0.8385(17) 0.4608(12) 0.3063(11) 0.043(7) Uiso 1 1 d . . . . .
O3 O 1.01506(9) 0.35827(7) 0.18789(7) 0.0333(3) Uani 1 1 d . . . . .
H3B H 1.009121 0.355203 0.221793 0.050 Uiso 1 1 calc GR . . . .
O4 O 0.93758(11) 0.59044(8) 0.31385(7) 0.0452(4) Uani 1 1 d . . . . .
H4A H 0.935426 0.555701 0.330044 0.068 Uiso 1 1 calc GR . . . .
C57 C 0.27292(12) 0.88884(9) 0.28654(9) 0.0253(4) Uani 1 1 d . . . . .
C58 C 0.22161(12) 0.83612(10) 0.26639(9) 0.0282(4) Uani 1 1 d . . . . .
H58 H 0.203193 0.827690 0.225657 0.034 Uiso 1 1 calc R . . . .
C59 C 0.19751(12) 0.79581(9) 0.30660(9) 0.0292(4) Uani 1 1 d . . . . .
H59 H 0.162697 0.760789 0.292206 0.035 Uiso 1 1 calc R . . . .
C60 C 0.22399(12) 0.80636(9) 0.36777(9) 0.0277(4) Uani 1 1 d . . . . .
C61 C 0.27857(11) 0.85862(9) 0.38721(9) 0.0244(4) Uani 1 1 d . . . . .
H61 H 0.298521 0.866078 0.428037 0.029 Uiso 1 1 calc R . . . .
C62 C 0.30409(11) 0.89975(9) 0.34805(8) 0.0229(4) Uani 1 1 d . . . . .
C63 C 0.36847(11) 0.95214(9) 0.37176(8) 0.0224(4) Uani 1 1 d . . . . .
H63 H 0.370918 0.960639 0.413720 0.027 Uiso 1 1 calc R . . . .
C64 C 0.40670(12) 1.06142(9) 0.34764(9) 0.0259(4) Uani 1 1 d . . . . .
C65 C 0.38253(14) 1.12443(10) 0.33223(9) 0.0327(5) Uani 1 1 d . . . . .
H65 H 0.325305 1.134203 0.316402 0.039 Uiso 1 1 calc R . . . .
C66 C 0.44279(15) 1.17285(10) 0.34019(10) 0.0376(5) Uani 1 1 d . . . . .
H66 H 0.426063 1.214876 0.329581 0.045 Uiso 1 1 calc R . . . .
C67 C 0.52804(15) 1.15851(10) 0.36399(10) 0.0388(5) Uani 1 1 d . . . . .
H67 H 0.568704 1.190866 0.369203 0.047 Uiso 1 1 calc R . . . .
C68 C 0.55257(14) 1.09612(10) 0.37997(10) 0.0326(5) Uani 1 1 d . . . . .
H68 H 0.609856 1.086709 0.396050 0.039 Uiso 1 1 calc R . . . .
C69 C 0.49241(12) 1.04709(9) 0.37226(9) 0.0259(4) Uani 1 1 d . . . . .
C70 C 0.45778(11) 0.93178(9) 0.36650(8) 0.0221(4) Uani 1 1 d . . . . .
H70 H 0.455905 0.925267 0.324346 0.027 Uiso 1 1 calc R . . . .
C71 C 0.48687(11) 0.87070(9) 0.40085(8) 0.0212(4) Uani 1 1 d . . . . .
C72 C 0.48154(11) 0.81227(9) 0.37088(8) 0.0227(4) Uani 1 1 d . . . . .
H72 H 0.464533 0.812312 0.329350 0.027 Uiso 1 1 calc R . . . .
C73 C 0.50069(11) 0.75356(9) 0.40059(9) 0.0244(4) Uani 1 1 d . . . . .
C74 C 0.52646(12) 0.75574(10) 0.46295(9) 0.0280(4) Uani 1 1 d . . . . .
H74 H 0.539217 0.717582 0.484281 0.034 Uiso 1 1 calc R . . . .
C75 C 0.53348(12) 0.81328(10) 0.49379(9) 0.0292(4) Uani 1 1 d . . . . .
H75 H 0.551554 0.813255 0.535293 0.035 Uiso 1 1 calc R . . . .
C76 C 0.51377(12) 0.87106(9) 0.46332(9) 0.0256(4) Uani 1 1 d . . . . .
C77 C 0.19492(13) 0.76527(10) 0.41368(10) 0.0331(5) Uani 1 1 d . . . . .
C78 C 0.13770(17) 0.70943(12) 0.38377(12) 0.0478(6) Uani 1 1 d . . . . .
H78A H 0.087477 0.726232 0.356378 0.072 Uiso 1 1 calc GR . . . .
H78B H 0.121809 0.684237 0.413764 0.072 Uiso 1 1 calc GR . . . .
H78C H 0.168070 0.682945 0.362485 0.072 Uiso 1 1 calc GR . . . .
C79 C 0.14341(15) 0.80720(12) 0.44546(11) 0.0424(6) Uani 1 1 d . . . . .
H79A H 0.178451 0.841665 0.465821 0.064 Uiso 1 1 calc GR . . . .
H79B H 0.124388 0.781665 0.473895 0.064 Uiso 1 1 calc GR . . . .
H79C H 0.095040 0.824594 0.416636 0.064 Uiso 1 1 calc GR . . . .
C80 C 0.27233(15) 0.73708(13) 0.45935(11) 0.0475(6) Uani 1 1 d . . . . .
H80A H 0.305261 0.711822 0.438972 0.071 Uiso 1 1 calc GR . . . .
H80B H 0.253400 0.710404 0.487069 0.071 Uiso 1 1 calc GR . . . .
H80C H 0.306781 0.771365 0.480608 0.071 Uiso 1 1 calc GR . . . .
C81 C 0.49125(13) 0.69068(9) 0.36469(9) 0.0286(4) Uani 1 1 d . . . . .
C82 C 0.39914(15) 0.68393(12) 0.32679(12) 0.0460(6) Uani 1 1 d . . . . .
H82A H 0.361691 0.682182 0.352508 0.069 Uiso 1 1 calc GR . . . .
H82B H 0.393475 0.645200 0.303618 0.069 Uiso 1 1 calc GR . . . .
H82C H 0.384558 0.720195 0.300514 0.069 Uiso 1 1 calc GR . . . .
C83 C 0.54941(15) 0.69169(11) 0.32230(10) 0.0379(5) Uani 1 1 d . . . . .
H83A H 0.534694 0.727567 0.295575 0.057 Uiso 1 1 calc GR . . . .
H83B H 0.542309 0.652532 0.299662 0.057 Uiso 1 1 calc GR . . . .
H83C H 0.607603 0.695588 0.345171 0.057 Uiso 1 1 calc GR . . . .
C84 C 0.51394(19) 0.63206(11) 0.40496(11) 0.0480(6) Uani 1 1 d . . . . .
H84A H 0.572385 0.634801 0.427570 0.072 Uiso 1 1 calc GR . . . .
H84B H 0.505687 0.593859 0.380946 0.072 Uiso 1 1 calc GR . . . .
H84C H 0.478063 0.630562 0.431780 0.072 Uiso 1 1 calc GR . . . .
N5 N 0.34495(11) 1.01150(8) 0.33668(7) 0.0254(3) Uani 1 1 d . . . . .
H5A H 0.2959(15) 1.0241(11) 0.3381(10) 0.028(6) Uiso 1 1 d . . . . .
N6 N 0.51784(10) 0.98414(7) 0.39123(7) 0.0248(3) Uani 1 1 d . . . . .
H6 H 0.5691(16) 0.9758(11) 0.3864(10) 0.036(6) Uiso 1 1 d . . . . .
O5 O 0.29163(9) 0.92913(7) 0.24473(6) 0.0288(3) Uani 1 1 d . . . . .
H5B H 0.3119(16) 0.9622(13) 0.2636(12) 0.046(8) Uiso 1 1 d . . . . .
O6 O 0.52011(9) 0.92667(7) 0.49568(6) 0.0316(3) Uani 1 1 d . . . . .
H6A H 0.5210(17) 0.9577(13) 0.4714(12) 0.048(8) Uiso 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
C1 C2 1.385(3) . ?
C1 C6 1.396(3) . ?
C1 O1 1.382(2) . ?
C2 C3 1.389(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.394(3) . ?
C4 C21 1.536(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.505(3) . ?
C7 C14 1.544(2) . ?
C7 N1 1.475(2) . ?
C8 C9 1.386(3) . ?
C8 C13 1.397(3) . ?
C8 N1 1.430(2) . ?
C9 C10 1.386(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.372(3) . ?
C12 C13 1.392(3) . ?
C13 N2 1.414(3) . ?
C14 C15 1.512(3) . ?
C14 N2 1.478(2) . ?
C15 C16 1.397(3) . ?
C15 C20 1.397(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.398(3) . ?
C17 C25 1.533(3) . ?
C18 C19 1.377(3) . ?
C19 C20 1.391(3) . ?
C20 O2 1.355(3) . ?
C21 C22 1.524(3) . ?
C21 C23 1.533(3) . ?
C21 C24 1.547(3) . ?
C25 C26 1.534(3) . ?
C25 C27 1.535(3) . ?
C25 C28 1.531(3) . ?
C29 C30 1.383(3) . ?
C29 C34 1.392(3) . ?
C29 O3 1.385(2) . ?
C30 C31 1.393(3) . ?
C31 C32 1.390(3) . ?
C32 C33 1.391(3) . ?
C32 C49 1.547(3) . ?
C33 C34 1.397(3) . ?
C34 C35 1.506(3) . ?
C35 C42 1.548(3) . ?
C35 N3 1.474(3) . ?
C36 C37 1.392(3) . ?
C36 C41 1.393(3) . ?
C36 N3 1.425(3) . ?
C37 C38 1.387(3) . ?
C38 C39 1.389(4) . ?
C39 C40 1.377(3) . ?
C40 C41 1.394(3) . ?
C41 N4 1.420(3) . ?
C42 C43 1.498(3) . ?
C42 N4 1.464(2) . ?
C43 C44 1.396(3) . ?
C43 C48 1.397(3) . ?
C44 C45 1.384(3) . ?
C45 C46 1.395(3) . ?
C45 C53 1.540(3) . ?
C46 C47 1.383(3) . ?
C47 C48 1.386(3) . ?
C48 O4 1.373(3) . ?
C49 C50 1.531(3) . ?
C49 C51 1.524(3) . ?
C49 C52 1.528(3) . ?
C53 C54 1.531(3) . ?
C53 C55 1.525(3) . ?
C53 C56 1.545(3) . ?
C57 C58 1.384(3) . ?
C57 C62 1.402(3) . ?
C57 O5 1.376(2) . ?
C58 C59 1.386(3) . ?
C59 C60 1.388(3) . ?
C60 C61 1.402(3) . ?
C60 C77 1.535(3) . ?
C61 C62 1.389(3) . ?
C62 C63 1.512(3) . ?
C63 C70 1.551(2) . ?
C63 N5 1.474(2) . ?
C64 C65 1.389(3) . ?
C64 C69 1.394(3) . ?
C64 N5 1.422(2) . ?
C65 C66 1.385(3) . ?
C66 C67 1.385(3) . ?
C67 C68 1.380(3) . ?
C68 C69 1.393(3) . ?
C69 N6 1.409(2) . ?
C70 C71 1.509(2) . ?
C70 N6 1.476(2) . ?
C71 C72 1.392(3) . ?
C71 C76 1.400(3) . ?
C72 C73 1.397(3) . ?
C73 C74 1.397(3) . ?
C73 C81 1.537(3) . ?
C74 C75 1.384(3) . ?
C75 C76 1.389(3) . ?
C76 O6 1.369(2) . ?
C77 C78 1.536(3) . ?
C77 C79 1.529(3) . ?
C77 C80 1.534(3) . ?
C81 C82 1.533(3) . ?
C81 C83 1.535(3) . ?
C81 C84 1.522(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.75(17) . . ?
O1 C1 C2 118.66(17) . . ?
O1 C1 C6 121.59(17) . . ?
C1 C2 C3 120.20(18) . . ?
C2 C3 C4 121.70(18) . . ?
C3 C4 C5 116.72(17) . . ?
C3 C4 C21 124.10(18) . . ?
C5 C4 C21 119.18(17) . . ?
C6 C5 C4 122.99(18) . . ?
C1 C6 C7 121.54(17) . . ?
C5 C6 C1 118.59(17) . . ?
C5 C6 C7 119.72(17) . . ?
C6 C7 C14 111.15(15) . . ?
N1 C7 C6 110.92(15) . . ?
N1 C7 C14 107.60(15) . . ?
C9 C8 C13 120.30(19) . . ?
C9 C8 N1 121.03(18) . . ?
C13 C8 N1 118.66(18) . . ?
C8 C9 C10 120.3(2) . . ?
C9 C10 C11 119.5(2) . . ?
C12 C11 C10 120.3(2) . . ?
C11 C12 C13 120.9(2) . . ?
C8 C13 N2 121.70(18) . . ?
C12 C13 C8 118.7(2) . . ?
C12 C13 N2 119.49(18) . . ?
C15 C14 C7 111.08(15) . . ?
N2 C14 C7 106.99(15) . . ?
N2 C14 C15 110.82(15) . . ?
C16 C15 C14 120.43(17) . . ?
C20 C15 C14 120.98(18) . . ?
C20 C15 C16 118.39(18) . . ?
C17 C16 C15 122.65(18) . . ?
C16 C17 C18 117.08(19) . . ?
C16 C17 C25 123.33(18) . . ?
C18 C17 C25 119.59(19) . . ?
C19 C18 C17 121.7(2) . . ?
C18 C19 C20 120.22(19) . . ?
C19 C20 C15 119.9(2) . . ?
O2 C20 C15 121.82(19) . . ?
O2 C20 C19 118.21(19) . . ?
C4 C21 C24 109.18(16) . . ?
C22 C21 C4 111.72(17) . . ?
C22 C21 C23 108.51(17) . . ?
C22 C21 C24 108.86(18) . . ?
C23 C21 C4 109.30(16) . . ?
C23 C21 C24 109.23(18) . . ?
C17 C25 C26 109.27(18) . . ?
C17 C25 C27 111.66(18) . . ?
C26 C25 C27 108.9(2) . . ?
C28 C25 C17 109.73(18) . . ?
C28 C25 C26 109.60(19) . . ?
C28 C25 C27 107.63(19) . . ?
C8 N1 C7 113.15(15) . . ?
C13 N2 C14 118.27(16) . . ?
C30 C29 C34 120.27(19) . . ?
C30 C29 O3 118.17(18) . . ?
O3 C29 C34 121.56(18) . . ?
C29 C30 C31 119.9(2) . . ?
C32 C31 C30 121.68(19) . . ?
C31 C32 C33 116.89(19) . . ?
C31 C32 C49 123.91(18) . . ?
C33 C32 C49 119.19(19) . . ?
C32 C33 C34 122.92(19) . . ?
C29 C34 C33 118.26(18) . . ?
C29 C34 C35 121.52(18) . . ?
C33 C34 C35 119.80(18) . . ?
C34 C35 C42 110.13(16) . . ?
N3 C35 C34 111.26(16) . . ?
N3 C35 C42 106.95(16) . . ?
C37 C36 C41 119.50(19) . . ?
C37 C36 N3 119.66(19) . . ?
C41 C36 N3 120.74(19) . . ?
C38 C37 C36 120.9(2) . . ?
C37 C38 C39 119.4(2) . . ?
C40 C39 C38 119.8(2) . . ?
C39 C40 C41 121.3(2) . . ?
C36 C41 C40 119.0(2) . . ?
C36 C41 N4 120.25(18) . . ?
C40 C41 N4 120.74(19) . . ?
C43 C42 C35 111.39(16) . . ?
N4 C42 C35 107.23(16) . . ?
N4 C42 C43 112.02(16) . . ?
C44 C43 C42 119.84(18) . . ?
C44 C43 C48 118.31(19) . . ?
C48 C43 C42 121.44(18) . . ?
C45 C44 C43 123.47(19) . . ?
C44 C45 C46 116.16(19) . . ?
C44 C45 C53 123.51(19) . . ?
C46 C45 C53 120.32(19) . . ?
C47 C46 C45 122.3(2) . . ?
C46 C47 C48 120.1(2) . . ?
C47 C48 C43 119.7(2) . . ?
O4 C48 C43 122.3(2) . . ?
O4 C48 C47 118.0(2) . . ?
C50 C49 C32 109.11(17) . . ?
C51 C49 C32 111.32(19) . . ?
C51 C49 C50 108.4(2) . . ?
C51 C49 C52 109.8(2) . . ?
C52 C49 C32 109.47(17) . . ?
C52 C49 C50 108.8(2) . . ?
C45 C53 C56 108.81(17) . . ?
C54 C53 C45 110.10(17) . . ?
C54 C53 C56 109.89(18) . . ?
C55 C53 C45 111.80(17) . . ?
C55 C53 C54 108.50(18) . . ?
C55 C53 C56 107.71(19) . . ?
C36 N3 C35 116.04(16) . . ?
C41 N4 C42 114.79(17) . . ?
C58 C57 C62 119.79(18) . . ?
O5 C57 C58 118.12(17) . . ?
O5 C57 C62 122.09(17) . . ?
C57 C58 C59 120.36(19) . . ?
C58 C59 C60 121.73(19) . . ?
C59 C60 C61 116.84(18) . . ?
C59 C60 C77 123.51(18) . . ?
C61 C60 C77 119.63(18) . . ?
C62 C61 C60 122.77(18) . . ?
C57 C62 C63 121.17(17) . . ?
C61 C62 C57 118.40(17) . . ?
C61 C62 C63 120.31(17) . . ?
C62 C63 C70 110.44(14) . . ?
N5 C63 C62 110.44(15) . . ?
N5 C63 C70 107.35(14) . . ?
C65 C64 C69 119.52(18) . . ?
C65 C64 N5 120.33(18) . . ?
C69 C64 N5 120.12(17) . . ?
C66 C65 C64 120.7(2) . . ?
C65 C66 C67 119.8(2) . . ?
C68 C67 C66 119.9(2) . . ?
C67 C68 C69 120.7(2) . . ?
C64 C69 N6 120.46(17) . . ?
C68 C69 C64 119.37(18) . . ?
C68 C69 N6 120.13(18) . . ?
C71 C70 C63 111.05(14) . . ?
N6 C70 C63 107.88(14) . . ?
N6 C70 C71 109.46(15) . . ?
C72 C71 C70 120.18(16) . . ?
C72 C71 C76 118.90(17) . . ?
C76 C71 C70 120.76(16) . . ?
C71 C72 C73 122.77(17) . . ?
C72 C73 C81 119.99(17) . . ?
C74 C73 C72 116.72(17) . . ?
C74 C73 C81 123.28(17) . . ?
C75 C74 C73 121.65(18) . . ?
C74 C75 C76 120.63(18) . . ?
C75 C76 C71 119.32(18) . . ?
O6 C76 C71 122.05(17) . . ?
O6 C76 C75 118.62(17) . . ?
C60 C77 C78 111.68(18) . . ?
C79 C77 C60 109.01(17) . . ?
C79 C77 C78 107.76(18) . . ?
C79 C77 C80 109.9(2) . . ?
C80 C77 C60 110.17(17) . . ?
C80 C77 C78 108.25(19) . . ?
C82 C81 C73 109.38(16) . . ?
C82 C81 C83 108.06(19) . . ?
C83 C81 C73 110.19(16) . . ?
C84 C81 C73 112.10(18) . . ?
C84 C81 C82 108.75(19) . . ?
C84 C81 C83 108.26(18) . . ?
C64 N5 C63 116.44(15) . . ?
C69 N6 C70 117.06(15) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 261.0 37.8 ?
2 -0.017 0.246 0.761 10.7 0.4 ?
3 -0.017 0.254 0.261 10.7 0.4 ?
4 0.000 0.500 0.500 261.0 37.8 ?
5 0.017 0.746 0.739 10.7 0.4 ?
6 0.017 0.754 0.239 10.7 0.4 ?

_olex2_date_sample_data_collection 2019-09-12
_olex2_date_sample_submission    2019-08-21
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id 'KL 4-T Cry'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.807
