# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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data_2-NO2radical
_database_code_depnum_ccdc_archive 'CCDC 2004974'
loop_
_audit_author_name
_audit_author_address
'thomas l gianetti'
;University of Arizona
United States of America
;
_audit_update_record             
;
2020-05-20 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;
_audit_creation_date             2019-10-30
_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            2-NO2radical
_chemical_name_systematic        2-NO2radical
_chemical_formula_moiety         'C31 H38 N5 O4'
_chemical_formula_sum            'C31 H38 N5 O4'
_chemical_formula_weight         544.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.834(7)
_cell_length_b                   11.010(7)
_cell_length_c                   13.357(9)
_cell_angle_alpha                71.977(17)
_cell_angle_beta                 84.217(17)
_cell_angle_gamma                64.762(17)
_cell_volume                     1369.6(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3993
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0757 before and 0.0448 after correction. The Ratio of minimum to maximum transmission is 0.8423. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark gray'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             582
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12298
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.545
_diffrn_reflns_theta_min         1.604
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3329
_reflns_number_total             5025
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.260
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.022
_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)+(0.0625P)²+1.1428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1487
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00Q(H00C,H00D), C00S(H00E,H00F), C00T(H00G,H00H), C00X(H00I,
 H00J), C00Y(H00K,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R), C00U(H00U),
 C00V(H00V), C00W(H00W)
2.c Idealised Me refined as rotating group:
 C00Z(H00Q,H00S,H00T), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C012(H01G,
 H01H,H01I), C013(H01J,H01K,H01L), C014(H01M,H01N,H01O)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.35755(18) 0.72620(18) 0.00308(12) 0.0269(4) Uani 1 1 d . . . . .
O002 O 0.52279(17) 0.80091(18) 0.09446(13) 0.0269(4) Uani 1 1 d . . . . .
O003 O -0.15677(17) 1.08037(18) 0.31801(13) 0.0276(4) Uani 1 1 d . . . . .
O004 O -0.14414(18) 0.9851(2) 0.48643(13) 0.0314(5) Uani 1 1 d . . . . .
N005 N -0.0968(2) 0.9875(2) 0.39885(15) 0.0222(5) Uani 1 1 d . . . . .
N006 N 0.3652(2) 0.5108(2) 0.36619(15) 0.0215(5) Uani 1 1 d . . . . .
N007 N 0.0949(2) 1.0048(2) 0.22232(15) 0.0211(5) Uani 1 1 d . . . . .
N008 N 0.3995(2) 0.1266(2) 0.60386(16) 0.0261(5) Uani 1 1 d . . . . .
N009 N 0.0592(2) 1.4140(3) 0.2279(2) 0.0376(6) Uani 1 1 d . . . . .
C00A C 0.2236(2) 0.7570(2) 0.29483(18) 0.0200(5) Uani 1 1 d . . . . .
C00B C 0.3053(2) 0.7589(3) 0.20453(18) 0.0197(5) Uani 1 1 d . . . . .
C00C C 0.2406(2) 0.8700(3) 0.11024(18) 0.0203(5) Uani 1 1 d . . . . .
C00D C 0.0308(2) 0.8731(2) 0.39009(18) 0.0210(5) Uani 1 1 d . . . . .
C00E C 0.1366(2) 0.9952(3) 0.12060(18) 0.0207(5) Uani 1 1 d . . . . .
C00F C 0.2544(2) 0.6297(3) 0.37681(18) 0.0211(5) Uani 1 1 d . . . . .
C00G C 0.2687(2) 0.8571(3) 0.00745(18) 0.0220(5) Uani 1 1 d . . . . .
C00H C 0.1128(2) 0.8816(2) 0.30165(17) 0.0194(5) Uani 1 1 d . . . . .
C00I C 0.4703(3) 0.5240(3) 0.29991(18) 0.0226(5) Uani 1 1 d . . . . .
C00J C 0.4415(2) 0.6515(3) 0.21910(18) 0.0215(5) Uani 1 1 d . . . . .
C00K C 0.0683(2) 1.1338(3) 0.24717(19) 0.0230(6) Uani 1 1 d . . . . .
H00A H 0.044289 1.122712 0.321975 0.028 Uiso 1 1 calc R . . . .
H00B H -0.010458 1.212598 0.203195 0.028 Uiso 1 1 calc R . . . .
C00L C 0.0646(2) 0.7477(3) 0.47092(18) 0.0228(6) Uani 1 1 d . . . . .
H00L H 0.010255 0.745358 0.531309 0.027 Uiso 1 1 calc R . . . .
C00M C 0.5520(3) 0.6697(3) 0.16188(19) 0.0241(6) Uani 1 1 d . . . . .
C00N C 0.6013(3) 0.4153(3) 0.3154(2) 0.0263(6) Uani 1 1 d . . . . .
H00N H 0.618516 0.327519 0.366874 0.032 Uiso 1 1 calc R . . . .
C00O C 0.2043(3) 0.9688(3) -0.07927(19) 0.0250(6) Uani 1 1 d . . . . .
H00O H 0.226053 0.959896 -0.148109 0.030 Uiso 1 1 calc R . . . .
C00P C 0.0712(3) 1.1085(3) 0.03281(19) 0.0241(6) Uani 1 1 d . . . . .
H00P H 0.002656 1.194100 0.041042 0.029 Uiso 1 1 calc R . . . .
C00Q C 0.5069(3) 0.1737(3) 0.59669(19) 0.0250(6) Uani 1 1 d . . . . .
H00C H 0.583412 0.120102 0.558428 0.030 Uiso 1 1 calc R . . . .
H00D H 0.541568 0.152896 0.668649 0.030 Uiso 1 1 calc R . . . .
C00R C 0.1748(3) 0.6274(3) 0.46532(19) 0.0238(6) Uani 1 1 d . . . . .
H00R H 0.196678 0.542818 0.521586 0.029 Uiso 1 1 calc R . . . .
C00S C 0.3846(3) 0.3718(3) 0.43671(18) 0.0237(6) Uani 1 1 d . . . . .
H00E H 0.435926 0.300752 0.399636 0.028 Uiso 1 1 calc R . . . .
H00F H 0.293964 0.370076 0.452127 0.028 Uiso 1 1 calc R . . . .
C00T C 0.4604(3) 0.3299(3) 0.54081(19) 0.0254(6) Uani 1 1 d . . . . .
H00G H 0.540807 0.352620 0.527162 0.030 Uiso 1 1 calc R . . . .
H00H H 0.399565 0.384446 0.586723 0.030 Uiso 1 1 calc R . . . .
C00U C 0.1076(3) 1.0943(3) -0.06584(19) 0.0262(6) Uani 1 1 d . . . . .
H00U H 0.065677 1.172076 -0.126076 0.031 Uiso 1 1 calc R . . . .
C00V C 0.6818(3) 0.5629(3) 0.1796(2) 0.0275(6) Uani 1 1 d . . . . .
H00V H 0.755275 0.576017 0.139751 0.033 Uiso 1 1 calc R . . . .
C00W C 0.7046(3) 0.4365(3) 0.2556(2) 0.0295(6) Uani 1 1 d . . . . .
H00W H 0.793904 0.362740 0.266539 0.035 Uiso 1 1 calc R . . . .
C00X C 0.1913(3) 1.1681(3) 0.2277(2) 0.0293(6) Uani 1 1 d . . . . .
H00I H 0.204781 1.195647 0.150925 0.035 Uiso 1 1 calc R . . . .
H00J H 0.273344 1.082603 0.260858 0.035 Uiso 1 1 calc R . . . .
C00Y C 0.1784(3) 1.2852(3) 0.2704(2) 0.0312(6) Uani 1 1 d . . . . .
H00K H 0.173658 1.254358 0.348109 0.037 Uiso 1 1 calc R . . . .
H00M H 0.261000 1.303769 0.253543 0.037 Uiso 1 1 calc R . . . .
C00Z C 0.4551(3) -0.0257(3) 0.6436(2) 0.0330(6) Uani 1 1 d . . . . .
H00Q H 0.528663 -0.066564 0.598818 0.049 Uiso 1 1 calc GR . . . .
H00S H 0.382806 -0.056654 0.642906 0.049 Uiso 1 1 calc GR . . . .
H00T H 0.491229 -0.056609 0.715869 0.049 Uiso 1 1 calc GR . . . .
C010 C 0.2928(3) 0.1877(3) 0.6709(2) 0.0347(7) Uani 1 1 d . . . . .
H01A H 0.331969 0.162819 0.741312 0.052 Uiso 1 1 calc GR . . . .
H01B H 0.223237 0.151572 0.676050 0.052 Uiso 1 1 calc GR . . . .
H01C H 0.250971 0.290247 0.640864 0.052 Uiso 1 1 calc GR . . . .
C011 C 0.6162(3) 0.8143(3) 0.0140(2) 0.0367(7) Uani 1 1 d . . . . .
H01D H 0.574067 0.906326 -0.038827 0.055 Uiso 1 1 calc GR . . . .
H01E H 0.640063 0.739950 -0.019505 0.055 Uiso 1 1 calc GR . . . .
H01F H 0.698878 0.805986 0.044700 0.055 Uiso 1 1 calc GR . . . .
C012 C 0.3824(3) 0.7048(3) -0.0980(2) 0.0397(7) Uani 1 1 d . . . . .
H01G H 0.422322 0.767479 -0.142067 0.060 Uiso 1 1 calc GR . . . .
H01H H 0.296211 0.725374 -0.131122 0.060 Uiso 1 1 calc GR . . . .
H01I H 0.445922 0.606916 -0.090592 0.060 Uiso 1 1 calc GR . . . .
C013 C 0.0350(3) 1.5145(3) 0.2849(3) 0.0448(8) Uani 1 1 d . . . . .
H01J H 0.027793 1.471350 0.360022 0.067 Uiso 1 1 calc GR . . . .
H01K H -0.050154 1.597580 0.257986 0.067 Uiso 1 1 calc GR . . . .
H01L H 0.111036 1.542494 0.275050 0.067 Uiso 1 1 calc GR . . . .
C014 C 0.0750(4) 1.4786(4) 0.1190(3) 0.0663(12) Uani 1 1 d . . . . .
H01M H 0.156052 1.498200 0.112281 0.099 Uiso 1 1 calc GR . . . .
H01N H -0.005946 1.566723 0.092385 0.099 Uiso 1 1 calc GR . . . .
H01O H 0.085579 1.414902 0.078004 0.099 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
O001 C00G 1.366(3) . ?
O001 C012 1.422(3) . ?
O002 C00M 1.364(3) . ?
O002 C011 1.418(3) . ?
O003 N005 1.235(3) . ?
O004 N005 1.226(3) . ?
N005 C00D 1.444(3) . ?
N006 C00F 1.384(3) . ?
N006 C00I 1.400(3) . ?
N006 C00S 1.465(3) . ?
N007 C00E 1.409(3) . ?
N007 C00H 1.388(3) . ?
N007 C00K 1.461(3) . ?
N008 C00Q 1.447(3) . ?
N008 C00Z 1.452(3) . ?
N008 C010 1.447(3) . ?
N009 C00Y 1.445(4) . ?
N009 C013 1.452(4) . ?
N009 C014 1.437(4) . ?
C00A C00B 1.423(3) . ?
C00A C00F 1.414(3) . ?
C00A C00H 1.408(3) . ?
C00B C00C 1.438(3) . ?
C00B C00J 1.428(3) . ?
C00C C00E 1.397(3) . ?
C00C C00G 1.413(3) . ?
C00D C00H 1.409(3) . ?
C00D C00L 1.390(3) . ?
C00E C00P 1.393(3) . ?
C00F C00R 1.391(3) . ?
C00G C00O 1.375(3) . ?
C00I C00J 1.410(3) . ?
C00I C00N 1.395(3) . ?
C00J C00M 1.409(3) . ?
C00K H00A 0.9900 . ?
C00K H00B 0.9900 . ?
C00K C00X 1.512(4) . ?
C00L H00L 0.9500 . ?
C00L C00R 1.372(3) . ?
C00M C00V 1.379(4) . ?
C00N H00N 0.9500 . ?
C00N C00W 1.368(4) . ?
C00O H00O 0.9500 . ?
C00O C00U 1.386(4) . ?
C00P H00P 0.9500 . ?
C00P C00U 1.374(4) . ?
C00Q H00C 0.9900 . ?
C00Q H00D 0.9900 . ?
C00Q C00T 1.520(4) . ?
C00R H00R 0.9500 . ?
C00S H00E 0.9900 . ?
C00S H00F 0.9900 . ?
C00S C00T 1.527(3) . ?
C00T H00G 0.9900 . ?
C00T H00H 0.9900 . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C00W 1.382(4) . ?
C00W H00W 0.9500 . ?
C00X H00I 0.9900 . ?
C00X H00J 0.9900 . ?
C00X C00Y 1.514(4) . ?
C00Y H00K 0.9900 . ?
C00Y H00M 0.9900 . ?
C00Z H00Q 0.9800 . ?
C00Z H00S 0.9800 . ?
C00Z H00T 0.9800 . ?
C010 H01A 0.9800 . ?
C010 H01B 0.9800 . ?
C010 H01C 0.9800 . ?
C011 H01D 0.9800 . ?
C011 H01E 0.9800 . ?
C011 H01F 0.9800 . ?
C012 H01G 0.9800 . ?
C012 H01H 0.9800 . ?
C012 H01I 0.9800 . ?
C013 H01J 0.9800 . ?
C013 H01K 0.9800 . ?
C013 H01L 0.9800 . ?
C014 H01M 0.9800 . ?
C014 H01N 0.9800 . ?
C014 H01O 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00G O001 C012 117.3(2) . . ?
C00M O002 C011 117.2(2) . . ?
O003 N005 C00D 119.11(19) . . ?
O004 N005 O003 122.5(2) . . ?
O004 N005 C00D 118.3(2) . . ?
C00F N006 C00I 120.0(2) . . ?
C00F N006 C00S 120.2(2) . . ?
C00I N006 C00S 119.05(19) . . ?
C00E N007 C00K 118.98(19) . . ?
C00H N007 C00E 118.1(2) . . ?
C00H N007 C00K 121.0(2) . . ?
C00Q N008 C00Z 110.3(2) . . ?
C010 N008 C00Q 111.4(2) . . ?
C010 N008 C00Z 109.8(2) . . ?
C00Y N009 C013 111.3(2) . . ?
C014 N009 C00Y 111.0(2) . . ?
C014 N009 C013 107.9(3) . . ?
C00F C00A C00B 119.6(2) . . ?
C00H C00A C00B 119.7(2) . . ?
C00H C00A C00F 120.6(2) . . ?
C00A C00B C00C 115.7(2) . . ?
C00A C00B C00J 116.1(2) . . ?
C00J C00B C00C 128.2(2) . . ?
C00E C00C C00B 118.3(2) . . ?
C00E C00C C00G 117.6(2) . . ?
C00G C00C C00B 124.0(2) . . ?
C00H C00D N005 123.0(2) . . ?
C00L C00D N005 116.1(2) . . ?
C00L C00D C00H 120.7(2) . . ?
C00C C00E N007 118.8(2) . . ?
C00P C00E N007 119.7(2) . . ?
C00P C00E C00C 121.5(2) . . ?
N006 C00F C00A 118.1(2) . . ?
N006 C00F C00R 122.1(2) . . ?
C00R C00F C00A 119.8(2) . . ?
O001 C00G C00C 114.9(2) . . ?
O001 C00G C00O 124.2(2) . . ?
C00O C00G C00C 120.8(2) . . ?
N007 C00H C00A 117.5(2) . . ?
N007 C00H C00D 124.7(2) . . ?
C00D C00H C00A 117.7(2) . . ?
N006 C00I C00J 118.3(2) . . ?
C00N C00I N006 120.8(2) . . ?
C00N C00I C00J 120.9(2) . . ?
C00I C00J C00B 119.0(2) . . ?
C00M C00J C00B 123.3(2) . . ?
C00M C00J C00I 117.5(2) . . ?
N007 C00K H00A 109.4 . . ?
N007 C00K H00B 109.4 . . ?
N007 C00K C00X 111.3(2) . . ?
H00A C00K H00B 108.0 . . ?
C00X C00K H00A 109.4 . . ?
C00X C00K H00B 109.4 . . ?
C00D C00L H00L 119.3 . . ?
C00R C00L C00D 121.4(2) . . ?
C00R C00L H00L 119.3 . . ?
O002 C00M C00J 115.5(2) . . ?
O002 C00M C00V 123.4(2) . . ?
C00V C00M C00J 121.0(2) . . ?
C00I C00N H00N 120.4 . . ?
C00W C00N C00I 119.3(2) . . ?
C00W C00N H00N 120.4 . . ?
C00G C00O H00O 120.1 . . ?
C00G C00O C00U 119.7(2) . . ?
C00U C00O H00O 120.1 . . ?
C00E C00P H00P 120.6 . . ?
C00U C00P C00E 118.8(2) . . ?
C00U C00P H00P 120.6 . . ?
N008 C00Q H00C 108.9 . . ?
N008 C00Q H00D 108.9 . . ?
N008 C00Q C00T 113.2(2) . . ?
H00C C00Q H00D 107.8 . . ?
C00T C00Q H00C 108.9 . . ?
C00T C00Q H00D 108.9 . . ?
C00F C00R H00R 120.2 . . ?
C00L C00R C00F 119.7(2) . . ?
C00L C00R H00R 120.2 . . ?
N006 C00S H00E 108.6 . . ?
N006 C00S H00F 108.6 . . ?
N006 C00S C00T 114.5(2) . . ?
H00E C00S H00F 107.6 . . ?
C00T C00S H00E 108.6 . . ?
C00T C00S H00F 108.6 . . ?
C00Q C00T C00S 111.0(2) . . ?
C00Q C00T H00G 109.4 . . ?
C00Q C00T H00H 109.4 . . ?
C00S C00T H00G 109.4 . . ?
C00S C00T H00H 109.4 . . ?
H00G C00T H00H 108.0 . . ?
C00O C00U H00U 119.3 . . ?
C00P C00U C00O 121.3(2) . . ?
C00P C00U H00U 119.3 . . ?
C00M C00V H00V 120.2 . . ?
C00M C00V C00W 119.7(2) . . ?
C00W C00V H00V 120.2 . . ?
C00N C00W C00V 121.5(2) . . ?
C00N C00W H00W 119.3 . . ?
C00V C00W H00W 119.3 . . ?
C00K C00X H00I 108.9 . . ?
C00K C00X H00J 108.9 . . ?
C00K C00X C00Y 113.3(2) . . ?
H00I C00X H00J 107.7 . . ?
C00Y C00X H00I 108.9 . . ?
C00Y C00X H00J 108.9 . . ?
N009 C00Y C00X 112.7(2) . . ?
N009 C00Y H00K 109.0 . . ?
N009 C00Y H00M 109.0 . . ?
C00X C00Y H00K 109.0 . . ?
C00X C00Y H00M 109.0 . . ?
H00K C00Y H00M 107.8 . . ?
N008 C00Z H00Q 109.5 . . ?
N008 C00Z H00S 109.5 . . ?
N008 C00Z H00T 109.5 . . ?
H00Q C00Z H00S 109.5 . . ?
H00Q C00Z H00T 109.5 . . ?
H00S C00Z H00T 109.5 . . ?
N008 C010 H01A 109.5 . . ?
N008 C010 H01B 109.5 . . ?
N008 C010 H01C 109.5 . . ?
H01A C010 H01B 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 109.5 . . ?
O002 C011 H01D 109.5 . . ?
O002 C011 H01E 109.5 . . ?
O002 C011 H01F 109.5 . . ?
H01D C011 H01E 109.5 . . ?
H01D C011 H01F 109.5 . . ?
H01E C011 H01F 109.5 . . ?
O001 C012 H01G 109.5 . . ?
O001 C012 H01H 109.5 . . ?
O001 C012 H01I 109.5 . . ?
H01G C012 H01H 109.5 . . ?
H01G C012 H01I 109.5 . . ?
H01H C012 H01I 109.5 . . ?
N009 C013 H01J 109.5 . . ?
N009 C013 H01K 109.5 . . ?
N009 C013 H01L 109.5 . . ?
H01J C013 H01K 109.5 . . ?
H01J C013 H01L 109.5 . . ?
H01K C013 H01L 109.5 . . ?
N009 C014 H01M 109.5 . . ?
N009 C014 H01N 109.5 . . ?
N009 C014 H01O 109.5 . . ?
H01M C014 H01N 109.5 . . ?
H01M C014 H01O 109.5 . . ?
H01N C014 H01O 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene/hexanes'
_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_2-Hradical
_database_code_depnum_ccdc_archive 'CCDC 2004977'
loop_
_audit_author_name
_audit_author_address
'thomas l gianetti'
;University of Arizona
United States of America
;
_audit_update_record             
;
2020-05-20 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;
_audit_creation_date             2019-10-30
_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            2-Hradical
_chemical_name_systematic        2-Hradical
_chemical_formula_moiety         'C30.95 H38.88 N4 O2, 0.33(H2 O)'
_chemical_formula_sum            'C30.95 H39.55 N4 O2.33'
_chemical_formula_weight         505.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   20.1829(5)
_cell_length_b                   10.7314(3)
_cell_length_c                   25.5707(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5538.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.08
_cell_measurement_theta_min      3.56
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1038 before and 0.0593 after correction. The Ratio of minimum to maximum transmission is 0.8361. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            45766
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         73.269
_diffrn_reflns_theta_min         3.560
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5594
_reflns_number_total             7238
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.535
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         7238
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0669
_refine_ls_restrained_S_all      1.109
_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)+(0.0528P)²+3.1410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C3AA-N0AB
 1.47 with sigma of 0.01
 N0AA-C4 \\sim N0AB-C1AA
 with sigma of 0.02
 N0AA-C6 \\sim N0AB-C6A
 with sigma of 0.02
 C3-C4 \\sim C4AA-C1AA
 with sigma of 0.02
 N0AA-C3 \\sim N0AB-C4AA
 with sigma of 0.04
 C4-C6 \\sim C1AA-C6A
 with sigma of 0.04
3. Others
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=1-FVAR(1)
 Fixed Sof: N0AA(0.6667) C3(0.6667) H3A(0.6667) H3B(0.6667) C4(0.6667)
 H4A(0.6667) C6(0.6667) H6A(0.6667) H6B(0.6667) H6C(0.6667) C4AA(0.33333)
 H4AD(0.33333) H4AE(0.33333) C1AA(0.33333) H1AA(0.33333) H1AB(0.33333)
 N0AB(0.33333) C6A(0.33333) H6AA(0.33333) H6AB(0.33333) H6AC(0.33333)
 O2A(0.33333) H2AA(0.33333) H2AB(0.33333) H3AC(0.6667) H3AD(0.6667)
 H3AE(0.6667) H3AF(0.33333) H3AG(0.33333) H3AH(0.33333) H4B(0.6667)
 C0AA(0.33333) H0AA(0.33333) H0AB(0.33333) C2(0.6667) H2A(0.6667) H2B(0.6667)
4.a Free rotating group:
 O2A(H2AA,H2AB)
4.b Secondary CH2 refined with riding coordinates:
 C00I(H00C,H00E), C3A(H3AA,H3AB), C3(H3A,H3B), C4AA(H4AD,H4AE), C1AA(H1AA,
 H1AB), C0AA(H0AA,H0AB), C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00Q(H00Q), C00R(H00R)
4.d Idealised Me refined as rotating group:
 C00K(H00F,H00G,H00H), C00S(H00K,H00P,H00S), C4A(H4AA,H4AB,H4AC), C6(H6A,H6B,
 H6C), C1(H1A,H1B,H1C), C6A(H6AA,H6AB,H6AC), C3AA(H3AC,H3AD,H3AE), C3AA(H3AF,
 H3AG,H3AH)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.45057(5) 0.69694(10) 0.24546(5) 0.0259(3) Uani 1 1 d . . . . .
O002 O 0.48079(5) 0.52500(11) 0.32277(5) 0.0303(3) Uani 1 1 d . . . . .
N003 N 0.30077(7) 0.35716(13) 0.22486(6) 0.0290(3) Uani 1 1 d . . . . .
N004 N 0.26211(7) 0.67505(14) 0.35348(6) 0.0325(3) Uani 1 1 d . . . . .
C006 C 0.38231(7) 0.51901(14) 0.23939(7) 0.0218(3) Uani 1 1 d . . . . .
C007 C 0.43592(7) 0.59010(13) 0.21894(7) 0.0220(3) Uani 1 1 d . . . . .
C008 C 0.35822(7) 0.41990(14) 0.20826(7) 0.0244(3) Uani 1 1 d . . . . .
C009 C 0.37464(8) 0.61189(15) 0.33316(7) 0.0255(3) Uani 1 1 d . . . . .
C00A C 0.46905(8) 0.55368(15) 0.17422(7) 0.0275(4) Uani 1 1 d . . . . .
H00A H 0.506428 0.599244 0.162211 0.033 Uiso 1 1 calc R . . . .
C00B C 0.39167(8) 0.38416(15) 0.16286(7) 0.0275(4) Uani 1 1 d . . . . .
H00B H 0.376410 0.315134 0.142960 0.033 Uiso 1 1 calc R . . . .
C00C C 0.44192(8) 0.60796(15) 0.34944(7) 0.0274(4) Uani 1 1 d . . . . .
C00D C 0.44705(9) 0.44972(16) 0.14705(7) 0.0300(4) Uani 1 1 d . . . . .
H00D H 0.470610 0.423009 0.116906 0.036 Uiso 1 1 calc R . . . .
C00E C 0.33005(8) 0.68021(15) 0.36472(7) 0.0294(4) Uani 1 1 d . . . . .
C00F C 0.27986(7) 0.51370(15) 0.28989(7) 0.0277(4) Uani 1 1 d . . . . .
C00G C 0.23657(8) 0.57818(16) 0.32336(8) 0.0313(4) Uani 1 1 d . . . . .
C00H C 0.25565(8) 0.41783(16) 0.25772(7) 0.0295(4) Uani 1 1 d . . . . .
C00I C 0.28010(9) 0.24444(16) 0.19710(8) 0.0331(4) Uani 1 1 d . . . . .
H00C H 0.251192 0.194810 0.220432 0.040 Uiso 1 1 calc R . . . .
H00E H 0.319881 0.193708 0.189363 0.040 Uiso 1 1 calc R . . . .
C00J C 0.34871(8) 0.54805(16) 0.28774(8) 0.0309(4) Uani 1 1 d . . . . .
C00K C 0.51037(8) 0.75927(16) 0.23176(8) 0.0327(4) Uani 1 1 d . . . . .
H00F H 0.507389 0.789065 0.195608 0.049 Uiso 1 1 calc GR . . . .
H00G H 0.547702 0.701381 0.234981 0.049 Uiso 1 1 calc GR . . . .
H00H H 0.517181 0.830257 0.255259 0.049 Uiso 1 1 calc GR . . . .
C00L C 0.46477(9) 0.68065(18) 0.38996(8) 0.0349(4) Uani 1 1 d . . . . .
H00L H 0.510381 0.679945 0.399146 0.042 Uiso 1 1 calc R . . . .
C00M C 0.14701(8) 0.44762(19) 0.29404(9) 0.0418(5) Uani 1 1 d . . . . .
H00M H 0.101721 0.423931 0.295995 0.050 Uiso 1 1 calc R . . . .
C00N C 0.18863(8) 0.38387(17) 0.26066(8) 0.0359(4) Uani 1 1 d . . . . .
H00N H 0.172048 0.317523 0.239829 0.043 Uiso 1 1 calc R . . . .
C00O C 0.35370(10) 0.75343(18) 0.40568(8) 0.0385(4) Uani 1 1 d . . . . .
H00O H 0.323772 0.802375 0.425689 0.046 Uiso 1 1 calc R . . . .
C00P C 0.24310(10) 0.26904(18) 0.14599(9) 0.0381(5) Uani 1 1 d . . . . .
C00Q C 0.42034(10) 0.7550(2) 0.41724(8) 0.0412(5) Uani 1 1 d . . . . .
H00Q H 0.436165 0.807836 0.444317 0.049 Uiso 1 1 calc R . . . .
C00R C 0.16931(8) 0.54497(18) 0.32472(9) 0.0399(5) Uani 1 1 d . . . . .
H00R H 0.139338 0.589125 0.346566 0.048 Uiso 1 1 calc R . . . .
C00S C 0.54995(8) 0.52762(19) 0.33333(9) 0.0398(5) Uani 1 1 d . . . . .
H00K H 0.572693 0.468214 0.310414 0.060 Uiso 1 1 calc GR . . . .
H00P H 0.557715 0.504765 0.369927 0.060 Uiso 1 1 calc GR . . . .
H00S H 0.567111 0.611671 0.326928 0.060 Uiso 1 1 calc GR . . . .
C3A C 0.22893(13) 0.1473(2) 0.11790(9) 0.0538(8) Uani 0.977(5) 1 d . . P A 2
H3AA H 0.268654 0.093448 0.119950 0.065 Uiso 0.977(5) 1 calc R . P A 2
H3AB H 0.192268 0.103853 0.136029 0.065 Uiso 0.977(5) 1 calc R . P A 2
C4A C 0.20500(17) 0.0446(2) 0.03740(11) 0.0737(11) Uani 0.977(5) 1 d . . P A 2
H4AA H 0.246896 -0.001032 0.040404 0.111 Uiso 0.977(5) 1 calc GR . P A 2
H4AB H 0.194477 0.057508 0.000386 0.111 Uiso 0.977(5) 1 calc GR . P A 2
H4AC H 0.169498 -0.003633 0.053956 0.111 Uiso 0.977(5) 1 calc GR . P A 2
N1 N 0.21114(9) 0.16453(16) 0.06330(7) 0.0415(4) Uani 1 1 d . . . . .
N0AA N 0.08061(12) 0.7482(3) 0.44001(13) 0.0432(7) Uani 0.6667 1 d D . P B 1
C3 C 0.20086(16) 0.7095(3) 0.44032(14) 0.0378(7) Uani 0.6667 1 d D . P B 1
H3A H 0.188888 0.620274 0.437808 0.045 Uiso 0.6667 1 calc R . P B 1
H3B H 0.239880 0.716650 0.463593 0.045 Uiso 0.6667 1 calc R . P B 1
C4 C 0.14348(16) 0.7811(3) 0.46392(14) 0.0447(8) Uani 0.6667 1 d D . P B 1
H4A H 0.1514(17) 0.878(3) 0.4518(14) 0.054 Uiso 0.6667 1 d R . P C 1
C6 C 0.0308(2) 0.8457(4) 0.4488(2) 0.0697(15) Uani 0.6667 1 d D . P B 1
H6A H 0.021886 0.853224 0.486299 0.105 Uiso 0.6667 1 calc GR . P B 1
H6B H -0.010235 0.823583 0.430448 0.105 Uiso 0.6667 1 calc GR . P B 1
H6C H 0.047400 0.925329 0.435352 0.105 Uiso 0.6667 1 calc GR . P B 1
C1 C 0.14995(13) 0.2327(3) 0.05895(10) 0.0759(9) Uani 1 1 d . . . . .
H1A H 0.114574 0.186805 0.076776 0.114 Uiso 1 1 calc GR . . . .
H1B H 0.138501 0.242876 0.021945 0.114 Uiso 1 1 calc GR . . . .
H1C H 0.155118 0.314904 0.075153 0.114 Uiso 1 1 calc GR . . . .
C4AA C 0.1760(2) 0.7317(5) 0.4176(2) 0.0253(11) Uani 0.3333 1 d D . P B 2
H4AD H 0.165118 0.641771 0.418304 0.030 Uiso 0.3333 1 calc R . P B 2
H4AE H 0.205463 0.750245 0.447522 0.030 Uiso 0.3333 1 calc R . P B 2
C1AA C 0.1137(2) 0.8073(5) 0.42167(19) 0.0241(10) Uani 0.3333 1 d D . P B 2
H1AA H 0.125615 0.896785 0.420248 0.029 Uiso 0.3333 1 calc R . P B 2
H1AB H 0.085531 0.789100 0.390931 0.029 Uiso 0.3333 1 calc R . P B 2
N0AB N 0.0742(2) 0.7845(4) 0.47009(19) 0.0257(10) Uani 0.3333 1 d D . P B 2
C6A C 0.0211(4) 0.8789(8) 0.4740(3) 0.049(2) Uani 0.3333 1 d D . P B 2
H6AA H -0.006860 0.875089 0.442698 0.074 Uiso 0.3333 1 calc GR . P B 2
H6AB H 0.040805 0.962011 0.476914 0.074 Uiso 0.3333 1 calc GR . P B 2
H6AC H -0.006013 0.862040 0.505039 0.074 Uiso 0.3333 1 calc GR . P B 2
H00I H 0.2687(10) 0.3225(18) 0.1243(8) 0.029(5) Uiso 1 1 d . . . . .
H00J H 0.2022(13) 0.314(2) 0.1525(10) 0.055(7) Uiso 1 1 d . . . . .
O2A O 0.1441(2) 0.8210(5) 0.56548(16) 0.0412(10) Uani 0.3333 1 d . . P D 2
H2AA H 0.126980 0.832420 0.534644 0.062 Uiso 0.3333 1 d G . P D 2
H2AB H 0.186636 0.817459 0.559939 0.062 Uiso 0.3333 1 d G . P D 2
C3AA C 0.05279(11) 0.6410(2) 0.46414(11) 0.0589(7) Uani 1 1 d D . . . .
H3AC H 0.083954 0.571300 0.461399 0.088 Uiso 0.6667 1 calc GR . P B 1
H3AD H 0.011234 0.619107 0.446571 0.088 Uiso 0.6667 1 calc GR . P B 1
H3AE H 0.043982 0.658720 0.501091 0.088 Uiso 0.6667 1 calc GR . P B 1
H3AF H 0.019318 0.633440 0.436556 0.088 Uiso 0.3333 1 calc GR . P B 2
H3AG H 0.034303 0.611225 0.497301 0.088 Uiso 0.3333 1 calc GR . P B 2
H3AH H 0.091654 0.590870 0.454937 0.088 Uiso 0.3333 1 calc GR . P B 2
H4B H 0.1399(16) 0.763(3) 0.5058(14) 0.042(9) Uiso 0.6667 1 d . . P E 1
C0AA C 0.2107(6) 0.7640(14) 0.3666(4) 0.030(2) Uani 0.3333 1 d . . P B 2
H0AA H 0.177635 0.766312 0.338013 0.036 Uiso 0.3333 1 calc R . P B 2
H0AB H 0.230550 0.848064 0.369583 0.036 Uiso 0.3333 1 calc R . P B 2
C2 C 0.2191(3) 0.7586(7) 0.3855(2) 0.0333(12) Uani 0.6667 1 d . . P B 1
H2A H 0.177635 0.774133 0.365924 0.040 Uiso 0.6667 1 calc R . P B 1
H2B H 0.241978 0.839647 0.389616 0.040 Uiso 0.6667 1 calc R . P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C007 1.3644(18) . ?
O001 C00K 1.4236(18) . ?
O002 C00C 1.369(2) . ?
O002 C00S 1.4221(19) . ?
N003 C008 1.406(2) . ?
N003 C00H 1.400(2) . ?
N003 C00I 1.463(2) . ?
N004 C00E 1.402(2) . ?
N004 C00G 1.393(2) . ?
N004 C0AA 1.449(14) . ?
N004 C2 1.493(7) . ?
C006 C007 1.424(2) . ?
C006 C008 1.415(2) . ?
C006 C00J 1.444(2) . ?
C007 C00A 1.381(2) . ?
C008 C00B 1.397(2) . ?
C009 C00C 1.421(2) . ?
C009 C00E 1.414(2) . ?
C009 C00J 1.446(2) . ?
C00A C00D 1.387(2) . ?
C00B C00D 1.381(2) . ?
C00C C00L 1.377(3) . ?
C00E C00O 1.394(3) . ?
C00F C00G 1.405(2) . ?
C00F C00H 1.405(2) . ?
C00F C00J 1.439(2) . ?
C00G C00R 1.404(2) . ?
C00H C00N 1.403(2) . ?
C00I C00P 1.528(3) . ?
C00L C00Q 1.388(3) . ?
C00M C00N 1.379(3) . ?
C00M C00R 1.382(3) . ?
C00O C00Q 1.377(3) . ?
C00P C3A 1.518(3) . ?
C3A N1 1.453(3) . ?
C4A N1 1.453(3) . ?
N1 C1 1.440(3) . ?
N0AA C4 1.452(4) . ?
N0AA C6 1.468(5) . ?
N0AA C3AA 1.421(3) . ?
C3 C4 1.515(4) . ?
C3 C2 1.542(6) . ?
C4AA C1AA 1.500(6) . ?
C4AA C0AA 1.520(13) . ?
C1AA N0AB 1.493(6) . ?
N0AB C6A 1.479(7) . ?
N0AB C3AA 1.607(5) . ?

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
C007 O001 C00K 117.14(13) . . ?
C00C O002 C00S 117.07(14) . . ?
C008 N003 C00I 118.97(15) . . ?
C00H N003 C008 119.66(14) . . ?
C00H N003 C00I 119.36(14) . . ?
C00E N004 C0AA 128.8(5) . . ?
C00E N004 C2 115.6(3) . . ?
C00G N004 C00E 120.32(14) . . ?
C00G N004 C0AA 110.8(5) . . ?
C00G N004 C2 122.5(3) . . ?
C007 C006 C00J 123.77(14) . . ?
C008 C006 C007 117.22(15) . . ?
C008 C006 C00J 118.86(14) . . ?
O001 C007 C006 115.62(14) . . ?
O001 C007 C00A 122.99(14) . . ?
C00A C007 C006 121.36(14) . . ?
N003 C008 C006 118.25(15) . . ?
C00B C008 N003 121.20(15) . . ?
C00B C008 C006 120.54(14) . . ?
C00C C009 C00J 124.54(15) . . ?
C00E C009 C00C 117.16(16) . . ?
C00E C009 C00J 118.27(15) . . ?
C007 C00A C00D 119.16(15) . . ?
C00D C00B C008 119.64(15) . . ?
O002 C00C C009 114.90(15) . . ?
O002 C00C C00L 123.48(15) . . ?
C00L C00C C009 121.60(16) . . ?
C00B C00D C00A 121.47(17) . . ?
N004 C00E C009 119.01(16) . . ?
C00O C00E N004 120.75(16) . . ?
C00O C00E C009 120.22(16) . . ?
C00G C00F C00J 119.84(16) . . ?
C00H C00F C00G 120.07(15) . . ?
C00H C00F C00J 120.07(16) . . ?
N004 C00G C00F 118.32(14) . . ?
N004 C00G C00R 122.26(17) . . ?
C00R C00G C00F 119.42(18) . . ?
N003 C00H C00F 117.77(14) . . ?
N003 C00H C00N 122.59(16) . . ?
C00N C00H C00F 119.61(17) . . ?
N003 C00I C00P 114.29(14) . . ?
C006 C00J C009 128.29(14) . . ?
C00F C00J C006 115.53(15) . . ?
C00F C00J C009 116.12(16) . . ?
C00C C00L C00Q 119.18(17) . . ?
C00N C00M C00R 121.87(16) . . ?
C00M C00N C00H 119.44(18) . . ?
C00Q C00O C00E 120.18(17) . . ?
C3A C00P C00I 110.37(16) . . ?
C00O C00Q C00L 121.05(18) . . ?
C00M C00R C00G 119.53(18) . . ?
N1 C3A C00P 113.07(17) . . ?
C4A N1 C3A 110.27(18) . . ?
C1 N1 C3A 110.5(2) . . ?
C1 N1 C4A 110.0(2) . . ?
C4 N0AA C6 111.2(3) . . ?
C3AA N0AA C4 111.0(3) . . ?
C3AA N0AA C6 103.9(3) . . ?
C4 C3 C2 111.8(4) . . ?
N0AA C4 C3 112.2(3) . . ?
C1AA C4AA C0AA 108.8(6) . . ?
N0AB C1AA C4AA 114.6(4) . . ?
C1AA N0AB C3AA 102.9(4) . . ?
C6A N0AB C1AA 109.4(4) . . ?
C6A N0AB C3AA 117.8(5) . . ?
N004 C0AA C4AA 112.2(8) . . ?
N004 C2 C3 115.6(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene/hexanes'
_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_2-NO2cation
_database_code_depnum_ccdc_archive 'CCDC 2004975'
loop_
_audit_author_name
_audit_author_address
'thomas l gianetti'
;University of Arizona
United States of America
;
_audit_update_record             
;
2020-05-20 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;
_audit_creation_date             2019-11-22
_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            2-NO2cation
_chemical_name_systematic        2-NO2cation
_chemical_formula_moiety         'B F4, C31 H38 N5 O4'
_chemical_formula_sum            'C31 H39 B F4 N5 O4'
_chemical_formula_weight         632.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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'
B B 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   22.4230(7)
_cell_length_b                   11.1591(4)
_cell_length_c                   26.6457(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.7260(10)
_cell_angle_gamma                90
_cell_volume                     6103.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9744
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      73.18
_cell_measurement_theta_min      3.92
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0834 before and 0.0551 after correction. The Ratio of minimum to maximum transmission is 0.8493. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2664
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'from acetonitrile ether layering'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            72727
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         73.298
_diffrn_reflns_theta_min         3.923
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8589
_reflns_number_total             9160
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.337
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         9160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      0.965
_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)+(0.0610P)²+5.1492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1114
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00S(H00C,H00D), C00X(H00F,H00G), C00Z(H00H,H00I), C011(H01A,
 H01B), C012(H01C,H01D)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00Y(H00Y), C010(H010)
2.c Idealised Me refined as rotating group:
 C013(H01E,H01F,H01G), C014(H01H,H01I,H01J), C015(H01K,H01L,H01M), C016(H01N,
 H01O,H01P), C017(H01Q,H01R,H01S), C018(H01T,H01U,H01V)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.66233(4) 0.75770(7) 0.70744(3) 0.03669(16) Uani 1 1 d . . . . .
F002 F 0.57018(3) 0.66857(7) 0.64678(3) 0.03785(17) Uani 1 1 d . . . . .
F003 F 0.65648(4) 0.55488(7) 0.70006(3) 0.03868(17) Uani 1 1 d . . . . .
O004 O 0.51603(3) 0.69601(6) 0.34371(3) 0.02178(14) Uani 1 1 d . . . . .
F005 F 0.59597(4) 0.65305(7) 0.73796(3) 0.04144(19) Uani 1 1 d . . . . .
O006 O 0.60976(3) 0.53395(6) 0.38709(3) 0.02270(14) Uani 1 1 d . . . . .
O007 O 0.84918(3) 0.98418(7) 0.45305(3) 0.02603(15) Uani 1 1 d . . . . .
O008 O 0.84755(4) 1.14203(7) 0.50028(3) 0.02932(17) Uani 1 1 d . . . . .
N009 N 0.71979(3) 0.90160(7) 0.39329(3) 0.01498(13) Uani 1 1 d . . . . .
N00A N 0.63062(3) 0.82701(7) 0.52719(3) 0.01507(13) Uani 1 1 d . . . . .
N00B N 0.82419(4) 1.04632(7) 0.47764(3) 0.01947(15) Uani 1 1 d . . . . .
N00C N 0.67057(4) 1.08374(7) 0.63564(3) 0.02205(16) Uani 1 1 d . . . . .
N00D N 0.59365(4) 1.03687(8) 0.36532(4) 0.02542(17) Uani 1 1 d . . . . .
C00E C 0.71365(4) 0.97932(8) 0.54548(3) 0.01641(15) Uani 1 1 d . . . . .
H00E H 0.709801 1.001928 0.578420 0.020 Uiso 1 1 calc R . . . .
C00F C 0.58024(4) 0.73727(7) 0.43672(4) 0.01563(15) Uani 1 1 d . . . . .
C00G C 0.67780(4) 0.85831(7) 0.46141(3) 0.01296(14) Uani 1 1 d . . . . .
C00H C 0.67356(4) 0.88863(7) 0.51189(3) 0.01364(14) Uani 1 1 d . . . . .
C00I C 0.72346(4) 0.91976(7) 0.44525(3) 0.01343(14) Uani 1 1 d . . . . .
C00J C 0.69415(4) 0.79472(8) 0.36650(3) 0.01580(15) Uani 1 1 d . . . . .
C00K C 0.63564(4) 0.77159(7) 0.42624(3) 0.01380(14) Uani 1 1 d . . . . .
C00L C 0.58190(4) 0.75663(8) 0.49004(4) 0.01634(15) Uani 1 1 d . . . . .
C00M C 0.65428(4) 0.72341(8) 0.38451(3) 0.01540(15) Uani 1 1 d . . . . .
C00N C 0.76565(4) 1.00263(8) 0.48230(3) 0.01575(15) Uani 1 1 d . . . . .
C00O C 0.63790(4) 0.60583(8) 0.36192(4) 0.01866(16) Uani 1 1 d . . . . .
C00P C 0.52251(4) 0.68431(8) 0.39618(4) 0.01893(16) Uani 1 1 d . . . . .
C00Q C 0.63443(4) 0.83860(8) 0.58397(3) 0.01811(16) Uani 1 1 d . . . . .
H00A H 0.679137 0.863472 0.608377 0.022 Uiso 1 1 calc R . . . .
H00B H 0.626424 0.759043 0.596502 0.022 Uiso 1 1 calc R . . . .
C00R C 0.75823(4) 1.03454(8) 0.53008(3) 0.01703(15) Uani 1 1 d . . . . .
H00R H 0.784837 1.096293 0.552578 0.020 Uiso 1 1 calc R . . . .
C00S C 0.73113(5) 1.00087(8) 0.36101(4) 0.01988(17) Uani 1 1 d . . . . .
H00C H 0.760922 0.973033 0.344313 0.024 Uiso 1 1 calc R . . . .
H00D H 0.752434 1.068436 0.385844 0.024 Uiso 1 1 calc R . . . .
C00T C 0.47670(4) 0.63160(9) 0.41143(4) 0.02394(19) Uani 1 1 d . . . . .
H00T H 0.440410 0.590637 0.385168 0.029 Uiso 1 1 calc R . . . .
C00U C 0.65465(5) 0.56862(9) 0.31987(4) 0.02271(18) Uani 1 1 d . . . . .
H00U H 0.642820 0.490876 0.304544 0.027 Uiso 1 1 calc R . . . .
C00V C 0.53423(4) 0.70315(9) 0.50494(4) 0.02179(17) Uani 1 1 d . . . . .
H00V H 0.536520 0.711119 0.541163 0.026 Uiso 1 1 calc R . . . .
C00W C 0.70924(4) 0.75769(9) 0.32243(4) 0.01966(16) Uani 1 1 d . . . . .
H00W H 0.732863 0.808749 0.308457 0.024 Uiso 1 1 calc R . . . .
C00X C 0.58602(5) 0.92856(9) 0.58982(4) 0.02169(17) Uani 1 1 d . . . . .
H00F H 0.543690 0.918410 0.558189 0.026 Uiso 1 1 calc R . . . .
H00G H 0.579248 0.908347 0.623324 0.026 Uiso 1 1 calc R . . . .
C00Y C 0.68911(5) 0.64606(9) 0.30000(4) 0.02243(18) Uani 1 1 d . . . . .
H00Y H 0.698929 0.620924 0.270112 0.027 Uiso 1 1 calc R . . . .
C00Z C 0.66750(5) 1.04460(9) 0.31577(4) 0.02354(18) Uani 1 1 d . . . . .
H00H H 0.677806 1.096898 0.290323 0.028 Uiso 1 1 calc R . . . .
H00I H 0.642842 0.974703 0.294664 0.028 Uiso 1 1 calc R . . . .
C010 C 0.48444(5) 0.63931(9) 0.46610(5) 0.02522(19) Uani 1 1 d . . . . .
H010 H 0.454166 0.598923 0.476849 0.030 Uiso 1 1 calc R . . . .
C011 C 0.60574(5) 1.06043(9) 0.59304(4) 0.02316(18) Uani 1 1 d . . . . .
H01A H 0.604913 1.085535 0.557130 0.028 Uiso 1 1 calc R . . . .
H01B H 0.573402 1.109546 0.600441 0.028 Uiso 1 1 calc R . . . .
C012 C 0.62488(5) 1.11376(9) 0.33830(4) 0.02389(18) Uani 1 1 d . . . . .
H01C H 0.652011 1.174181 0.364897 0.029 Uiso 1 1 calc R . . . .
H01D H 0.590716 1.157089 0.307797 0.029 Uiso 1 1 calc R . . . .
C013 C 0.45646(5) 0.65559(11) 0.30134(5) 0.0302(2) Uani 1 1 d . . . . .
H01E H 0.456180 0.676089 0.265485 0.045 Uiso 1 1 calc GR . . . .
H01F H 0.419549 0.694492 0.305536 0.045 Uiso 1 1 calc GR . . . .
H01G H 0.452867 0.568505 0.303995 0.045 Uiso 1 1 calc GR . . . .
C014 C 0.58087(6) 0.42463(9) 0.36001(5) 0.0329(2) Uani 1 1 d . . . . .
H01H H 0.551223 0.441934 0.322074 0.049 Uiso 1 1 calc GR . . . .
H01I H 0.556481 0.387286 0.379234 0.049 Uiso 1 1 calc GR . . . .
H01J H 0.615140 0.369894 0.360213 0.049 Uiso 1 1 calc GR . . . .
C015 C 0.67423(6) 1.06082(10) 0.69073(4) 0.0292(2) Uani 1 1 d . . . . .
H01K H 0.642236 1.110864 0.697389 0.044 Uiso 1 1 calc GR . . . .
H01L H 0.718060 1.080080 0.717710 0.044 Uiso 1 1 calc GR . . . .
H01M H 0.664845 0.976138 0.694077 0.044 Uiso 1 1 calc GR . . . .
C016 C 0.69159(6) 1.20593(10) 0.63179(5) 0.0319(2) Uani 1 1 d . . . . .
H01N H 0.689478 1.219944 0.594807 0.048 Uiso 1 1 calc GR . . . .
H01O H 0.736462 1.217104 0.658628 0.048 Uiso 1 1 calc GR . . . .
H01P H 0.662925 1.262778 0.639360 0.048 Uiso 1 1 calc GR . . . .
C017 C 0.57872(6) 1.10297(12) 0.40611(5) 0.0361(3) Uani 1 1 d . . . . .
H01Q H 0.618520 1.140576 0.432416 0.054 Uiso 1 1 calc GR . . . .
H01R H 0.561342 1.047719 0.425484 0.054 Uiso 1 1 calc GR . . . .
H01S H 0.546282 1.164990 0.387820 0.054 Uiso 1 1 calc GR . . . .
C018 C 0.53445(6) 0.98339(11) 0.32561(6) 0.0400(3) Uani 1 1 d . . . . .
H01T H 0.503803 1.046824 0.305771 0.060 Uiso 1 1 calc GR . . . .
H01U H 0.514637 0.932397 0.344667 0.060 Uiso 1 1 calc GR . . . .
H01V H 0.544935 0.934852 0.299597 0.060 Uiso 1 1 calc GR . . . .
B019 B 0.62127(6) 0.65915(10) 0.69835(5) 0.0237(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 B019 1.3915(13) . ?
F002 B019 1.3946(13) . ?
F003 B019 1.3964(13) . ?
O004 C00P 1.3525(12) . ?
O004 C013 1.4313(11) . ?
F005 B019 1.3864(12) . ?
O006 C00O 1.3534(12) . ?
O006 C014 1.4325(12) . ?
O007 N00B 1.2327(11) . ?
O008 N00B 1.2348(11) . ?
N009 C00I 1.3685(10) . ?
N009 C00J 1.3901(11) . ?
N009 C00S 1.4858(11) . ?
N00A C00H 1.3719(10) . ?
N00A C00L 1.3856(11) . ?
N00A C00Q 1.4864(11) . ?
N00B C00N 1.4517(10) . ?
N00C C011 1.4635(13) . ?
N00C C015 1.4595(12) . ?
N00C C016 1.4596(13) . ?
N00D C012 1.4665(13) . ?
N00D C017 1.4596(15) . ?
N00D C018 1.4518(15) . ?
C00E C00H 1.4091(11) . ?
C00E C00R 1.3701(11) . ?
C00F C00K 1.4307(11) . ?
C00F C00L 1.4227(12) . ?
C00F C00P 1.4374(11) . ?
C00G C00H 1.4266(11) . ?
C00G C00I 1.4350(10) . ?
C00G C00K 1.4126(11) . ?
C00I C00N 1.4047(11) . ?
C00J C00M 1.4171(12) . ?
C00J C00W 1.4085(12) . ?
C00K C00M 1.4403(11) . ?
C00L C00V 1.4134(11) . ?
C00M C00O 1.4285(12) . ?
C00N C00R 1.3948(11) . ?
C00O C00U 1.3813(13) . ?
C00P C00T 1.3791(13) . ?
C00Q C00X 1.5319(13) . ?
C00S C00Z 1.5306(14) . ?
C00T C010 1.3987(16) . ?
C00U C00Y 1.3976(15) . ?
C00V C010 1.3767(14) . ?
C00W C00Y 1.3768(13) . ?
C00X C011 1.5290(14) . ?
C00Z C012 1.5266(14) . ?

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
C00P O004 C013 117.59(8) . . ?
C00O O006 C014 117.50(8) . . ?
C00I N009 C00J 119.39(7) . . ?
C00I N009 C00S 121.37(7) . . ?
C00J N009 C00S 118.30(7) . . ?
C00H N00A C00L 121.18(7) . . ?
C00H N00A C00Q 119.94(7) . . ?
C00L N00A C00Q 118.84(7) . . ?
O007 N00B O008 123.50(8) . . ?
O007 N00B C00N 118.47(8) . . ?
O008 N00B C00N 117.98(8) . . ?
C015 N00C C011 112.65(8) . . ?
C015 N00C C016 110.19(9) . . ?
C016 N00C C011 111.08(8) . . ?
C017 N00D C012 111.58(9) . . ?
C018 N00D C012 111.10(9) . . ?
C018 N00D C017 109.51(10) . . ?
C00R C00E C00H 119.24(8) . . ?
C00K C00F C00P 123.61(8) . . ?
C00L C00F C00K 118.58(7) . . ?
C00L C00F C00P 117.82(7) . . ?
C00H C00G C00I 119.72(7) . . ?
C00K C00G C00H 120.49(7) . . ?
C00K C00G C00I 119.74(7) . . ?
N00A C00H C00E 121.05(7) . . ?
N00A C00H C00G 118.82(7) . . ?
C00E C00H C00G 120.12(7) . . ?
N009 C00I C00G 118.24(7) . . ?
N009 C00I C00N 123.91(7) . . ?
C00N C00I C00G 117.62(7) . . ?
N009 C00J C00M 119.66(7) . . ?
N009 C00J C00W 119.44(8) . . ?
C00W C00J C00M 120.89(8) . . ?
C00F C00K C00M 126.53(7) . . ?
C00G C00K C00F 117.11(7) . . ?
C00G C00K C00M 116.32(7) . . ?
N00A C00L C00F 119.72(7) . . ?
N00A C00L C00V 120.44(8) . . ?
C00V C00L C00F 119.83(8) . . ?
C00J C00M C00K 118.06(7) . . ?
C00J C00M C00O 117.61(8) . . ?
C00O C00M C00K 124.25(8) . . ?
C00I C00N N00B 122.50(7) . . ?
C00R C00N N00B 115.87(7) . . ?
C00R C00N C00I 121.04(7) . . ?
O006 C00O C00M 115.32(8) . . ?
O006 C00O C00U 123.84(8) . . ?
C00U C00O C00M 120.68(9) . . ?
O004 C00P C00F 115.27(8) . . ?
O004 C00P C00T 124.23(8) . . ?
C00T C00P C00F 120.42(9) . . ?
N00A C00Q C00X 114.06(7) . . ?
C00E C00R C00N 121.86(8) . . ?
N009 C00S C00Z 111.79(7) . . ?
C00P C00T C010 119.05(9) . . ?
C00O C00U C00Y 119.58(8) . . ?
C010 C00V C00L 118.92(9) . . ?
C00Y C00W C00J 118.72(9) . . ?
C011 C00X C00Q 115.82(7) . . ?
C00W C00Y C00U 121.99(8) . . ?
C012 C00Z C00S 112.59(8) . . ?
C00V C010 C00T 122.55(9) . . ?
N00C C011 C00X 112.91(8) . . ?
N00D C012 C00Z 113.28(8) . . ?
F001 B019 F002 109.61(8) . . ?
F001 B019 F003 109.10(9) . . ?
F002 B019 F003 108.94(9) . . ?
F005 B019 F001 110.55(9) . . ?
F005 B019 F002 109.15(9) . . ?
F005 B019 F003 109.47(8) . . ?

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

data_2-Hcation
_database_code_depnum_ccdc_archive 'CCDC 2004976'
loop_
_audit_author_name
_audit_author_address
'thomas l gianetti'
;University of Arizona
United States of America
;
_audit_update_record             
;
2020-05-20 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;
_audit_creation_date             2019-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        2-Hcation
_chemical_formula_moiety         'C1 H2 Cl2, B F4, C31 H39 N4 O2'
_chemical_formula_sum            'C32 H41 B Cl2 F4 N4 O2'
_chemical_formula_weight         671.43
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   11.5110(3)
_cell_length_b                   12.4254(3)
_cell_length_c                   13.1831(3)
_cell_angle_alpha                85.1060(18)
_cell_angle_beta                 78.778(2)
_cell_angle_gamma                64.945(3)
_cell_volume                     1675.45(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12735
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.3260
_cell_measurement_theta_min      3.1460
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.3308
_exptl_crystal_description       block
_exptl_crystal_F_000             704.9552
_exptl_crystal_recrystallization_method DCM/Hexane
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35035
_diffrn_reflns_theta_full        26.3714
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.15
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 16.0839
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7904   38.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00    2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7904  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   14.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7904   38.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00   20.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7904  -99.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  5 omega  -21.00   13.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7904  -99.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00   -9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4154  -38.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega   -3.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4154   71.0000  133.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega  -44.00   49.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4154  -71.0000    2.0000 93

#__ type_ start__ end____ width___ exp.time_
  9 omega  -98.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7904 -179.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
 10 omega    1.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4154   57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   -3.00   95.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4154   38.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
 12 omega  -25.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4154  -99.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
 13 omega  -25.00   38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4154  -99.0000   90.0000 63

#__ type_ start__ end____ width___ exp.time_
 14 omega    1.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4154   57.0000  -60.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -13
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                6350
_reflns_number_total             6857
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3598
_refine_diff_density_min         -0.2530
_refine_diff_density_rms         0.0538
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             6.4655
_refine_ls_goodness_of_fit_ref   1.0699
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    67
_refine_ls_number_parameters     440
_refine_ls_number_reflns         6857
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.0699
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+1.2295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1060
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl2A)=Sof(C19A)=Sof(H19c)=Sof(H19d)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl2)=Sof(Cl1)=Sof(C19)=Sof(H19a)=Sof(H19b)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C00U(H00a,H00b), C00V(H00c,H00d), C00W(H00e,H00f), C00Z(H00g,H00i), C012(H01g,
 H01h), C013(H01i,H01j), C19(H19a,H19b), C19A(H19c,H19d)
3.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00X(H00X), C00Y(H00Y)
3.c Idealised Me refined as rotating group:
 C010(H01a,H01b,H01c), C011(H01d,H01e,H01f), C014(H01k,H01l,H01m), C015(H01n,
 H01o,H01p), C016(H01q,H01r,H01s), C018(H01t,H01u,H01v)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_disorder_group
Cl2 Cl 0.6481(7) 0.0801(7) 0.0532(6) 0.0643(14) Uani 0.458(15) . 1
Cl1 Cl 0.8937(5) -0.1394(2) 0.0022(2) 0.0542(11) Uani 0.458(15) . 1
F003 F 0.98678(10) -0.09681(9) 0.35618(8) 0.0341(2) Uani 1.000000 . .
O004 O 0.48235(10) 0.24523(9) 0.71789(8) 0.0202(2) Uani 1.000000 . .
O005 O 0.36688(11) 0.14794(9) 0.61248(9) 0.0220(2) Uani 1.000000 . .
F006 F 0.90882(11) 0.01158(10) 0.21780(9) 0.0400(3) Uani 1.000000 . .
F007 F 1.12459(11) -0.11507(11) 0.20372(9) 0.0473(3) Uani 1.000000 . .
F008 F 1.04188(11) 0.05447(10) 0.29791(11) 0.0469(3) Uani 1.000000 . .
N009 N 0.56842(13) 0.33716(12) 0.36173(10) 0.0200(3) Uani 1.000000 . .
N00A N 0.15058(12) 0.56344(11) 0.56883(10) 0.0194(3) Uani 1.000000 . .
N00B N -0.22375(13) 0.74113(12) 0.72701(11) 0.0231(3) Uani 1.000000 . .
N10 N 0.68199(15) 0.43610(14) 0.05950(11) 0.0322(3) Uani 1.000000 . .
C00D C 0.60778(15) 0.26320(13) 0.44471(12) 0.0184(3) Uani 1.000000 . .
C00E C 0.38486(15) 0.36015(13) 0.54016(11) 0.0169(3) Uani 1.000000 . .
C00F C 0.45541(15) 0.44050(14) 0.37489(12) 0.0189(3) Uani 1.000000 . .
C00G C 0.23817(15) 0.55352(13) 0.47828(12) 0.0189(3) Uani 1.000000 . .
C00H C 0.73476(15) 0.17254(14) 0.43602(12) 0.0200(3) Uani 1.000000 . .
H00H H 0.79353(15) 0.15892(14) 0.37207(12) 0.0240(4) Uiso 1.000000 R .
C00I C 0.56548(15) 0.21048(13) 0.62646(12) 0.0178(3) Uani 1.000000 . .
C00J C 0.27339(14) 0.35683(14) 0.60911(12) 0.0182(3) Uani 1.000000 . .
C00K C 0.15964(15) 0.46405(14) 0.62899(12) 0.0201(3) Uani 1.000000 . .
C00L C 0.26792(15) 0.24939(14) 0.65307(12) 0.0201(3) Uani 1.000000 . .
C00M C 0.36055(14) 0.45202(13) 0.46624(11) 0.0173(3) Uani 1.000000 . .
C00N C 0.77268(15) 0.10405(14) 0.52100(13) 0.0216(3) Uani 1.000000 . .
H00N H 0.85750(15) 0.04130(14) 0.51428(13) 0.0259(4) Uiso 1.000000 R .
C00O C 0.51748(14) 0.27744(13) 0.53844(11) 0.0171(3) Uani 1.000000 . .
C00P C 0.42607(16) 0.52793(14) 0.29817(12) 0.0211(3) Uani 1.000000 . .
H00P H 0.48757(16) 0.52103(14) 0.23669(12) 0.0253(4) Uiso 1.000000 R .
C00Q C 0.30622(16) 0.62481(14) 0.31282(12) 0.0219(3) Uani 1.000000 . .
H00Q H 0.28744(16) 0.68377(14) 0.26018(12) 0.0263(4) Uiso 1.000000 R .
C00R C 0.21258(16) 0.63979(14) 0.40048(12) 0.0216(3) Uani 1.000000 . .
H00R H 0.13185(16) 0.70794(14) 0.40766(12) 0.0259(4) Uiso 1.000000 R .
C00S C 0.69025(15) 0.12380(14) 0.61723(12) 0.0207(3) Uani 1.000000 . .
H00S H 0.72041(15) 0.07762(14) 0.67563(12) 0.0249(4) Uiso 1.000000 R .
C00T C 0.05583(16) 0.46786(15) 0.70810(13) 0.0257(4) Uani 1.000000 . .
H00T H -0.01611(16) 0.54110(15) 0.72838(13) 0.0309(4) Uiso 1.000000 R .
C00U C 0.03681(15) 0.67740(14) 0.59468(13) 0.0214(3) Uani 1.000000 . .
H00a H 0.01533(15) 0.68668(14) 0.67078(13) 0.0257(4) Uiso 1.000000 R .
H00b H 0.06048(15) 0.74291(14) 0.56525(13) 0.0257(4) Uiso 1.000000 R .
C00V C -0.08461(15) 0.68906(14) 0.55488(13) 0.0230(3) Uani 1.000000 . .
H00c H -0.07911(15) 0.71374(14) 0.48132(13) 0.0276(4) Uiso 1.000000 R .
H00d H -0.09075(15) 0.61161(14) 0.56034(13) 0.0276(4) Uiso 1.000000 R .
C00W C -0.20436(16) 0.78171(15) 0.61991(13) 0.0254(4) Uani 1.000000 . .
H00e H -0.28227(16) 0.79772(15) 0.58947(13) 0.0305(4) Uiso 1.000000 R .
H00f H -0.19374(16) 0.85681(15) 0.61901(13) 0.0305(4) Uiso 1.000000 R .
C00X C 0.16290(17) 0.25320(16) 0.72586(13) 0.0268(4) Uani 1.000000 . .
H00X H 0.15967(17) 0.18199(16) 0.75579(13) 0.0322(4) Uiso 1.000000 R .
C00Y C 0.06129(17) 0.36316(17) 0.75507(14) 0.0300(4) Uani 1.000000 . .
H00Y H -0.00712(17) 0.36582(17) 0.80979(14) 0.0360(5) Uiso 1.000000 R .
C00Z C 0.64475(16) 0.30356(15) 0.25638(12) 0.0235(3) Uani 1.000000 . .
H00g H 0.68678(16) 0.21580(15) 0.25154(12) 0.0282(4) Uiso 1.000000 R .
H00i H 0.58417(16) 0.33343(15) 0.20620(12) 0.0282(4) Uiso 1.000000 R .
C010 C 0.51864(18) 0.17237(16) 0.80654(13) 0.0303(4) Uani 1.000000 . .
H01a H 0.5390(13) 0.0899(3) 0.7911(4) 0.0454(6) Uiso 1.000000 GR .
H01b H 0.5954(8) 0.1768(9) 0.8240(6) 0.0454(6) Uiso 1.000000 GR .
H01c H 0.4464(5) 0.2006(7) 0.8651(3) 0.0454(6) Uiso 1.000000 GR .
C011 C 0.35808(18) 0.03829(15) 0.64407(15) 0.0318(4) Uani 1.000000 . .
H01d H 0.4313(7) -0.0272(2) 0.6050(8) 0.0478(6) Uiso 1.000000 GR .
H01e H 0.3609(13) 0.0258(6) 0.7181(3) 0.0478(6) Uiso 1.000000 GR .
H01f H 0.2760(6) 0.0411(5) 0.6308(10) 0.0478(6) Uiso 1.000000 GR .
C012 C 0.74968(17) 0.35050(17) 0.22525(13) 0.0289(4) Uani 1.000000 . .
H01g H 0.71632(17) 0.43277(17) 0.25062(13) 0.0347(5) Uiso 1.000000 R .
H01h H 0.82702(17) 0.30046(17) 0.25657(13) 0.0347(5) Uiso 1.000000 R .
C013 C 0.78750(17) 0.34825(17) 0.10754(14) 0.0315(4) Uani 1.000000 . .
H01i H 0.80928(17) 0.26814(17) 0.08199(14) 0.0378(5) Uiso 1.000000 R .
H01j H 0.86590(17) 0.36471(17) 0.08757(14) 0.0378(5) Uiso 1.000000 R .
C014 C -0.29238(17) 0.66462(16) 0.73836(15) 0.0304(4) Uani 1.000000 . .
H01k H -0.3802(5) 0.7100(3) 0.7227(10) 0.0456(6) Uiso 1.000000 GR .
H01l H -0.2448(7) 0.5976(6) 0.6905(7) 0.0456(6) Uiso 1.000000 GR .
H01m H -0.2984(11) 0.6346(9) 0.8095(3) 0.0456(6) Uiso 1.000000 GR .
C015 C -0.29489(19) 0.84093(17) 0.79782(16) 0.0367(4) Uani 1.000000 . .
H01n H -0.2474(7) 0.8912(7) 0.7917(8) 0.0550(7) Uiso 1.000000 GR .
H01o H -0.3816(5) 0.8876(7) 0.7806(7) 0.0550(7) Uiso 1.000000 GR .
H01p H -0.3035(12) 0.81115(17) 0.86889(19) 0.0550(7) Uiso 1.000000 GR .
C016 C 0.6887(2) 0.4026(2) -0.04565(15) 0.0453(5) Uani 1.000000 . .
H01q H 0.7704(7) 0.3981(14) -0.0885(3) 0.0679(8) Uiso 1.000000 GR .
H01r H 0.6853(16) 0.3250(7) -0.0445(2) 0.0679(8) Uiso 1.000000 GR .
H01s H 0.6149(9) 0.4623(8) -0.0745(5) 0.0679(8) Uiso 1.000000 GR .
B017 B 1.01591(19) -0.03685(17) 0.26841(16) 0.0277(4) Uani 1.000000 . .
C018 C 0.6800(2) 0.5533(2) 0.05883(17) 0.0480(5) Uani 1.000000 . .
H01t H 0.6722(17) 0.5767(7) 0.1298(2) 0.0720(8) Uiso 1.000000 GR .
H01u H 0.7608(7) 0.5523(4) 0.0172(11) 0.0720(8) Uiso 1.000000 GR .
H01v H 0.6055(10) 0.6102(3) 0.0290(12) 0.0720(8) Uiso 1.000000 GR .
C19 C 0.8074(17) 0.0176(11) 0.0145(10) 0.042(2) Uani 0.458(15) . 1
H19a H 0.8260(17) 0.0525(11) -0.0537(10) 0.050(3) Uiso 0.458(15) R 1
H19b H 0.8465(17) 0.0432(11) 0.0630(10) 0.050(3) Uiso 0.458(15) R 1
Cl2A Cl 0.6419(4) 0.0565(7) 0.0467(5) 0.0644(13) Uani 0.542(15) . 2
C19A C 0.8195(15) -0.0190(15) 0.0134(11) 0.088(5) Uani 0.542(15) . 2
H19c H 0.8510(15) 0.0059(15) -0.0559(11) 0.106(6) Uiso 0.542(15) R 2
H19d H 0.8612(15) -0.0014(15) 0.0649(11) 0.106(6) Uiso 0.542(15) R 2
Cl1A Cl 0.8530(7) -0.1702(9) 0.0147(3) 0.105(2) Uani 0.542(15) . 2


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
Cl2 C19 1.650(19) . ?
Cl1 C19 1.780(13) . ?
F003 B017 1.386(2) . ?
O004 C00I 1.3582(18) . ?
O004 C010 1.4315(19) . ?
O005 C00L 1.3544(19) . ?
O005 C011 1.4296(19) . ?
F006 B017 1.397(2) . ?
F007 B017 1.390(2) . ?
F008 B017 1.391(2) . ?
N009 C00D 1.384(2) . ?
N009 C00F 1.381(2) . ?
N009 C00Z 1.479(2) . ?
N00A C00G 1.381(2) . ?
N00A C00K 1.386(2) . ?
N00A C00U 1.475(2) . ?
N00B C00W 1.466(2) . ?
N00B C014 1.455(2) . ?
N00B C015 1.456(2) . ?
N10 C013 1.458(2) . ?
N10 C016 1.460(2) . ?
N10 C018 1.445(3) . ?
C00D C00H 1.407(2) . ?
C00D C00O 1.421(2) . ?
C00E C00J 1.435(2) . ?
C00E C00M 1.406(2) . ?
C00E C00O 1.431(2) . ?
C00F C00M 1.431(2) . ?
C00F C00P 1.397(2) . ?
C00G C00M 1.429(2) . ?
C00G C00R 1.397(2) . ?
C00H H00H 0.9500 . ?
C00H C00N 1.372(2) . ?
C00I C00O 1.428(2) . ?
C00I C00S 1.372(2) . ?
C00J C00K 1.416(2) . ?
C00J C00L 1.431(2) . ?
C00K C00T 1.412(2) . ?
C00L C00X 1.376(2) . ?
C00N H00N 0.9500 . ?
C00N C00S 1.399(2) . ?
C00P H00P 0.9500 . ?
C00P C00Q 1.385(2) . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.383(2) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00T H00T 0.9500 . ?
C00T C00Y 1.374(2) . ?
C00U H00a 0.9900 . ?
C00U H00b 0.9900 . ?
C00U C00V 1.533(2) . ?
C00V H00c 0.9900 . ?
C00V H00d 0.9900 . ?
C00V C00W 1.525(2) . ?
C00W H00e 0.9900 . ?
C00W H00f 0.9900 . ?
C00X H00X 0.9500 . ?
C00X C00Y 1.394(3) . ?
C00Y H00Y 0.9500 . ?
C00Z H00g 0.9900 . ?
C00Z H00i 0.9900 . ?
C00Z C012 1.527(2) . ?
C010 H01a 0.9800 . ?
C010 H01b 0.9800 . ?
C010 H01c 0.9800 . ?
C011 H01d 0.9800 . ?
C011 H01e 0.9800 . ?
C011 H01f 0.9800 . ?
C012 H01g 0.9900 . ?
C012 H01h 0.9900 . ?
C012 C013 1.527(2) . ?
C013 H01i 0.9900 . ?
C013 H01j 0.9900 . ?
C014 H01k 0.9800 . ?
C014 H01l 0.9800 . ?
C014 H01m 0.9800 . ?
C015 H01n 0.9800 . ?
C015 H01o 0.9800 . ?
C015 H01p 0.9800 . ?
C016 H01q 0.9800 . ?
C016 H01r 0.9800 . ?
C016 H01s 0.9800 . ?
C018 H01t 0.9800 . ?
C018 H01u 0.9800 . ?
C018 H01v 0.9800 . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
Cl2A C19A 1.830(17) . ?
C19A H19c 0.9900 . ?
C19A H19d 0.9900 . ?
C19A Cl1A 1.750(13) . ?

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
C010 O004 C00I 117.29(12) . . ?
C011 O005 C00L 117.57(13) . . ?
C00F N009 C00D 120.94(13) . . ?
C00Z N009 C00D 120.05(13) . . ?
C00Z N009 C00F 118.97(13) . . ?
C00K N00A C00G 120.55(13) . . ?
C00U N00A C00G 119.58(13) . . ?
C00U N00A C00K 119.38(13) . . ?
C014 N00B C00W 111.48(13) . . ?
C015 N00B C00W 111.35(14) . . ?
C015 N00B C014 109.44(14) . . ?
C016 N10 C013 111.82(16) . . ?
C018 N10 C013 111.99(16) . . ?
C018 N10 C016 109.65(16) . . ?
C00H C00D N009 120.62(14) . . ?
C00O C00D N009 119.34(14) . . ?
C00O C00D C00H 120.02(14) . . ?
C00M C00E C00J 116.60(13) . . ?
C00O C00E C00J 126.07(14) . . ?
C00O C00E C00M 117.32(13) . . ?
C00M C00F N009 118.17(13) . . ?
C00P C00F N009 122.15(14) . . ?
C00P C00F C00M 119.40(14) . . ?
C00M C00G N00A 117.94(13) . . ?
C00R C00G N00A 122.52(14) . . ?
C00R C00G C00M 119.52(14) . . ?
H00H C00H C00D 120.39(9) . . ?
C00N C00H C00D 119.22(14) . . ?
C00N C00H H00H 120.39(9) . . ?
C00O C00I O004 115.00(13) . . ?
C00S C00I O004 124.03(14) . . ?
C00S C00I C00O 120.81(14) . . ?
C00K C00J C00E 118.43(14) . . ?
C00L C00J C00E 123.32(14) . . ?
C00L C00J C00K 118.09(14) . . ?
C00J C00K N00A 119.42(14) . . ?
C00T C00K N00A 120.77(14) . . ?
C00T C00K C00J 119.79(14) . . ?
C00J C00L O005 115.17(13) . . ?
C00X C00L O005 124.26(14) . . ?
C00X C00L C00J 120.40(15) . . ?
C00F C00M C00E 119.88(14) . . ?
C00G C00M C00E 120.44(14) . . ?
C00G C00M C00F 119.55(14) . . ?
H00N C00N C00H 118.99(9) . . ?
C00S C00N C00H 122.02(15) . . ?
C00S C00N H00N 118.99(9) . . ?
C00E C00O C00D 118.38(13) . . ?
C00I C00O C00D 117.84(14) . . ?
C00I C00O C00E 123.76(14) . . ?
H00P C00P C00F 120.40(9) . . ?
C00Q C00P C00F 119.20(15) . . ?
C00Q C00P H00P 120.40(9) . . ?
H00Q C00Q C00P 118.44(9) . . ?
C00R C00Q C00P 123.12(14) . . ?
C00R C00Q H00Q 118.44(9) . . ?
C00Q C00R C00G 119.20(15) . . ?
H00R C00R C00G 120.40(9) . . ?
H00R C00R C00Q 120.40(9) . . ?
C00N C00S C00I 119.38(14) . . ?
H00S C00S C00I 120.31(9) . . ?
H00S C00S C00N 120.31(9) . . ?
H00T C00T C00K 120.77(10) . . ?
C00Y C00T C00K 118.45(16) . . ?
C00Y C00T H00T 120.77(10) . . ?
H00a C00U N00A 108.75(8) . . ?
H00b C00U N00A 108.75(8) . . ?
H00b C00U H00a 107.6 . . ?
C00V C00U N00A 114.01(13) . . ?
C00V C00U H00a 108.75(9) . . ?
C00V C00U H00b 108.75(9) . . ?
H00c C00V C00U 109.98(9) . . ?
H00d C00V C00U 109.98(9) . . ?
H00d C00V H00c 108.4 . . ?
C00W C00V C00U 108.56(13) . . ?
C00W C00V H00c 109.98(9) . . ?
C00W C00V H00d 109.98(9) . . ?
C00V C00W N00B 111.22(13) . . ?
H00e C00W N00B 109.39(8) . . ?
H00e C00W C00V 109.39(9) . . ?
H00f C00W N00B 109.39(8) . . ?
H00f C00W C00V 109.39(9) . . ?
H00f C00W H00e 108.0 . . ?
H00X C00X C00L 120.50(10) . . ?
C00Y C00X C00L 118.99(15) . . ?
C00Y C00X H00X 120.50(10) . . ?
C00X C00Y C00T 122.82(16) . . ?
H00Y C00Y C00T 118.59(10) . . ?
H00Y C00Y C00X 118.59(10) . . ?
H00g C00Z N009 108.61(8) . . ?
H00i C00Z N009 108.61(8) . . ?
H00i C00Z H00g 107.6 . . ?
C012 C00Z N009 114.60(13) . . ?
C012 C00Z H00g 108.61(10) . . ?
C012 C00Z H00i 108.61(9) . . ?
H01a C010 O004 109.5 . . ?
H01b C010 O004 109.5 . . ?
H01b C010 H01a 109.5 . . ?
H01c C010 O004 109.5 . . ?
H01c C010 H01a 109.5 . . ?
H01c C010 H01b 109.5 . . ?
H01d C011 O005 109.5 . . ?
H01e C011 O005 109.5 . . ?
H01e C011 H01d 109.5 . . ?
H01f C011 O005 109.5 . . ?
H01f C011 H01d 109.5 . . ?
H01f C011 H01e 109.5 . . ?
H01g C012 C00Z 109.86(10) . . ?
H01h C012 C00Z 109.86(9) . . ?
H01h C012 H01g 108.3 . . ?
C013 C012 C00Z 109.13(14) . . ?
C013 C012 H01g 109.86(10) . . ?
C013 C012 H01h 109.86(10) . . ?
C012 C013 N10 111.31(14) . . ?
H01i C013 N10 109.37(10) . . ?
H01i C013 C012 109.37(10) . . ?
H01j C013 N10 109.37(9) . . ?
H01j C013 C012 109.37(9) . . ?
H01j C013 H01i 108.0 . . ?
H01k C014 N00B 109.5 . . ?
H01l C014 N00B 109.5 . . ?
H01l C014 H01k 109.5 . . ?
H01m C014 N00B 109.5 . . ?
H01m C014 H01k 109.5 . . ?
H01m C014 H01l 109.5 . . ?
H01n C015 N00B 109.5 . . ?
H01o C015 N00B 109.5 . . ?
H01o C015 H01n 109.5 . . ?
H01p C015 N00B 109.5 . . ?
H01p C015 H01n 109.5 . . ?
H01p C015 H01o 109.5 . . ?
H01q C016 N10 109.5 . . ?
H01r C016 N10 109.5 . . ?
H01r C016 H01q 109.5 . . ?
H01s C016 N10 109.5 . . ?
H01s C016 H01q 109.5 . . ?
H01s C016 H01r 109.5 . . ?
F006 B017 F003 109.18(15) . . ?
F007 B017 F003 109.50(15) . . ?
F007 B017 F006 110.44(16) . . ?
F008 B017 F003 108.82(16) . . ?
F008 B017 F006 109.17(15) . . ?
F008 B017 F007 109.70(15) . . ?
H01t C018 N10 109.5 . . ?
H01u C018 N10 109.5 . . ?
H01u C018 H01t 109.5 . . ?
H01v C018 N10 109.5 . . ?
H01v C018 H01t 109.5 . . ?
H01v C018 H01u 109.5 . . ?
Cl1 C19 Cl2 121.1(10) . . ?
H19a C19 Cl2 107.1(5) . . ?
H19a C19 Cl1 107.1(5) . . ?
H19b C19 Cl2 107.1(5) . . ?
H19b C19 Cl1 107.1(4) . . ?
H19b C19 H19a 106.8 . . ?
H19c C19A Cl2A 110.8(5) . . ?
H19d C19A Cl2A 110.8(5) . . ?
H19d C19A H19c 108.88874069(3) . . ?
Cl1A C19A Cl2A 104.6(8) . . ?
Cl1A C19A H19c 110.8(5) . . ?
Cl1A C19A H19d 110.8(5) . . ?

_olex2_submission_original_sample_id tlg4xr1
_olex2_submission_special_instructions 'No special instructions were received'
