# 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).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_MeQn_17srv201
_database_code_depnum_ccdc_archive 'CCDC 1985987'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2020-02-24 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;


_audit_creation_date             2017-08-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B F4, C21 H27 N2 O2, 0.5(H2 O)'
_chemical_formula_sum            'C21 H28 B F4 N2 O2.50'
_chemical_formula_weight         435.26
_chemical_absolute_configuration ad
_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 0.0181 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'
B B 0.0090 0.0039 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.0721(2)
_cell_length_b                   15.6353(5)
_cell_length_c                   16.4422(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.2832(14)
_cell_angle_gamma                90
_cell_volume                     2053.52(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9656
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      74.25
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.683
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0898 before and 0.0443 after correction. 
The Ratio of minimum to maximum transmission is 0.8637. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23769
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.988
_diffrn_reflns_theta_min         2.716
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.804
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                6575
_reflns_number_total             6963
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 2602 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         6963
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.070
_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)+(0.0400P)²+1.6700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1050
_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. Restrained distances
 C8B-C7A \\sim C8A-C7A
 with sigma of 0.002
 C9A-C8A \\sim C9B-C8B
 with sigma of 0.002
 N1A-C10B \\sim N1A-C10A
 with sigma of 0.002
 C8A-C7A \\sim C8B-C7B
 with sigma of 0.002
 C7B-C6B \\sim C7A-C6A
 with sigma of 0.002
 C7A-C3A \\sim C7B-C3A
 with sigma of 0.002
 N1A-C6A \\sim N1A-C6B
 with sigma of 0.002
 O1A-H1A \\sim O1W-H1WB \\sim O1W-H1WA \\sim O1-H1
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uiso(C7B) = Uiso(C7A)
4. Others
 Fixed Sof: H3A(0.6) H3AA(0.4) C6A(0.6) H6AA(0.6) H6AB(0.6) C6B(0.4) H6BA(0.4)
 H6BB(0.4) C7A(0.6) H7A(0.6) C7B(0.4) H7B(0.4) C8A(0.6) H8A(0.6) C8B(0.4)
 H8B(0.4) C9A(0.6) H9AA(0.6) H9AB(0.6) C9B(0.4) H9BA(0.4) H9BB(0.4) C10A(0.4)
 H10A(0.4) H10B(0.4) H10C(0.4) C10B(0.6) H10D(0.6) H10E(0.6) H10F(0.6)
5.a Ternary CH refined with riding coordinates:
 C1(H1B), C3(H3), C7(H7), C11(H11), C1A(H1AA), C3A(H3A), C3A(H3AA), C7A(H7A),
 C7B(H7B), C11A(H11A)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C2A(H2AA,H2AB), C4A(H4AA,
 H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C6B(H6BA,H6BB)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C8A(H8A), C8B(H8B),
 C13A(H13A), C14A(H14A), C16A(H16A), C17A(H17A), C19A(H19A)
5.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C9B(H9BA,H9BB)
5.e Idealised Me refined as rotating group:
 C10(H10G,H10H,H10I), C21(H21D,H21E,H21F), C10A(H10A,H10B,H10C), C10B(H10D,
 H10E,H10F), C21A(H21A,H21B,H21C)
;
_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
F1 F 0.6445(3) 0.41788(15) 0.92357(14) 0.0350(5) Uani 1 1 d . . . . .
F2 F 0.7190(4) 0.34887(19) 0.81368(16) 0.0537(8) Uani 1 1 d . . . . .
F3 F 0.7413(4) 0.28200(17) 0.93804(18) 0.0547(7) Uani 1 1 d . . . . .
F4 F 0.9186(3) 0.3888(2) 0.9181(2) 0.0624(8) Uani 1 1 d . . . . .
B1 B 0.7602(6) 0.3582(3) 0.8982(3) 0.0315(10) Uani 1 1 d . . . . .
F1A F 0.3196(3) 0.56796(15) 0.46455(15) 0.0370(6) Uani 1 1 d . . . . .
F2A F 0.2843(3) 0.70998(16) 0.44200(17) 0.0425(6) Uani 1 1 d . . . . .
F3A F 0.1693(3) 0.6449(2) 0.54502(15) 0.0469(7) Uani 1 1 d . . . . .
F4A F 0.0634(3) 0.62016(19) 0.41259(15) 0.0460(7) Uani 1 1 d . . . . .
B1A B 0.2093(5) 0.6363(3) 0.4659(3) 0.0278(9) Uani 1 1 d . . . . .
O1 O 0.3702(3) 0.42557(17) 0.79720(15) 0.0262(6) Uani 1 1 d D . . . .
O2 O 0.6831(3) 0.71299(16) 0.55845(15) 0.0232(5) Uani 1 1 d . . . . .
N1 N 0.3192(4) 0.38643(19) 0.61406(18) 0.0224(6) Uani 1 1 d . . . . .
N2 N 0.3725(4) 0.7425(2) 0.83493(18) 0.0217(6) Uani 1 1 d . . . . .
C1 C 0.2826(4) 0.4696(2) 0.6583(2) 0.0183(7) Uani 1 1 d . . . . .
H1B H 0.2964 0.5179 0.6200 0.022 Uiso 1 1 calc R . . . .
C2 C 0.0968(4) 0.4688(3) 0.6715(2) 0.0247(8) Uani 1 1 d . . . . .
H2A H 0.0892 0.4769 0.7306 0.030 Uiso 1 1 calc R . . . .
H2B H 0.0366 0.5165 0.6406 0.030 Uiso 1 1 calc R . . . .
C3 C 0.0149(5) 0.3837(3) 0.6421(2) 0.0300(9) Uani 1 1 d . . . . .
H3 H -0.1033 0.3824 0.6538 0.036 Uiso 1 1 calc R . . . .
C4 C 0.1140(6) 0.3102(3) 0.6876(3) 0.0395(11) Uani 1 1 d . . . . .
H4A H 0.1239 0.3194 0.7477 0.047 Uiso 1 1 calc R . . . .
H4B H 0.0548 0.2554 0.6742 0.047 Uiso 1 1 calc R . . . .
C5 C 0.2878(5) 0.3066(2) 0.6616(3) 0.0337(9) Uani 1 1 d . . . . .
H5A H 0.3736 0.3018 0.7109 0.040 Uiso 1 1 calc R . . . .
H5B H 0.2965 0.2556 0.6268 0.040 Uiso 1 1 calc R . . . .
C6 C 0.1991(4) 0.3850(3) 0.5338(2) 0.0234(7) Uani 1 1 d . . . . .
H6A H 0.2316 0.3385 0.4984 0.028 Uiso 1 1 calc R . . . .
H6B H 0.2067 0.4398 0.5046 0.028 Uiso 1 1 calc R . . . .
C7 C 0.0179(5) 0.3709(2) 0.5493(2) 0.0257(8) Uani 1 1 d . . . . .
H7 H -0.0129 0.3101 0.5355 0.031 Uiso 1 1 calc R . . . .
C8 C -0.0985(5) 0.4273(3) 0.4943(2) 0.0295(8) Uani 1 1 d . . . . .
H8 H -0.0745 0.4867 0.4936 0.035 Uiso 1 1 calc R . . . .
C9 C -0.2326(5) 0.3988(3) 0.4468(3) 0.0383(10) Uani 1 1 d . . . . .
H9A H -0.2594 0.3396 0.4463 0.046 Uiso 1 1 calc R . . . .
H9B H -0.3025 0.4375 0.4129 0.046 Uiso 1 1 calc R . . . .
C10 C 0.4940(5) 0.3847(3) 0.5940(3) 0.0366(10) Uani 1 1 d . . . . .
H10G H 0.5156 0.4372 0.5647 0.055 Uiso 1 1 calc GR . . . .
H10H H 0.5079 0.3350 0.5593 0.055 Uiso 1 1 calc GR . . . .
H10I H 0.5733 0.3807 0.6450 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.4042(4) 0.4857(2) 0.7372(2) 0.0219(7) Uani 1 1 d . . . . .
H11 H 0.5211 0.4766 0.7255 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3881(4) 0.5776(2) 0.7673(2) 0.0197(7) Uani 1 1 d . . . . .
C13 C 0.3137(4) 0.5922(2) 0.8354(2) 0.0236(8) Uani 1 1 d . . . . .
H13 H 0.2643 0.5462 0.8610 0.028 Uiso 1 1 calc R . . . .
C14 C 0.3098(5) 0.6754(2) 0.8678(2) 0.0250(8) Uani 1 1 d . . . . .
H14 H 0.2594 0.6835 0.9160 0.030 Uiso 1 1 calc R . . . .
C15 C 0.4419(4) 0.7299(2) 0.7644(2) 0.0186(7) Uani 1 1 d . . . . .
C16 C 0.5033(4) 0.8029(2) 0.7274(2) 0.0213(7) Uani 1 1 d . . . . .
H16 H 0.4914 0.8579 0.7504 0.026 Uiso 1 1 calc R . . . .
C17 C 0.5796(4) 0.7948(2) 0.6589(2) 0.0214(7) Uani 1 1 d . . . . .
H17 H 0.6197 0.8440 0.6341 0.026 Uiso 1 1 calc R . . . .
C18 C 0.5985(4) 0.7132(2) 0.6251(2) 0.0188(7) Uani 1 1 d . . . . .
C19 C 0.5378(4) 0.6416(2) 0.6577(2) 0.0183(7) Uani 1 1 d . . . . .
H19 H 0.5505 0.5873 0.6334 0.022 Uiso 1 1 calc R . . . .
C20 C 0.4549(4) 0.6482(2) 0.7288(2) 0.0174(7) Uani 1 1 d . . . . .
C21 C 0.7319(5) 0.6317(3) 0.5303(2) 0.0258(8) Uani 1 1 d . . . . .
H21D H 0.8045 0.6400 0.4880 0.039 Uiso 1 1 calc GR . . . .
H21E H 0.6321 0.5995 0.5070 0.039 Uiso 1 1 calc GR . . . .
H21F H 0.7928 0.5998 0.5764 0.039 Uiso 1 1 calc GR . . . .
H1 H 0.465(4) 0.421(3) 0.829(2) 0.032(12) Uiso 1 1 d D . . . .
O1A O -0.1106(3) 0.47171(17) 0.17297(17) 0.0260(6) Uani 1 1 d D . . . .
O2A O 0.2995(3) 0.19175(17) -0.02765(16) 0.0288(6) Uani 1 1 d . . . . .
N1A N 0.1949(4) 0.5444(2) 0.10340(19) 0.0275(7) Uani 1 1 d D . . . .
N2A N 0.0497(4) 0.1730(2) 0.26851(19) 0.0257(7) Uani 1 1 d . . . . .
C1A C 0.1831(4) 0.4701(2) 0.1631(2) 0.0221(7) Uani 1 1 d . . . . .
H1AA H 0.2745 0.4288 0.1557 0.026 Uiso 1 1 calc R . . . .
C2A C 0.2218(6) 0.5061(3) 0.2508(2) 0.0338(9) Uani 1 1 d . . . . .
H2AA H 0.1278 0.4933 0.2814 0.041 Uiso 1 1 calc R . . . .
H2AB H 0.3239 0.4785 0.2799 0.041 Uiso 1 1 calc R . . . .
C3A C 0.2482(6) 0.6026(3) 0.2481(2) 0.0405(11) Uani 1 1 d D . . . .
H3A H 0.2713 0.6264 0.3051 0.049 Uiso 0.6 1 calc R . P A 1
H3AA H 0.2626 0.6247 0.3058 0.049 Uiso 0.4 1 calc R . P B 2
C4A C 0.0919(6) 0.6434(3) 0.2009(3) 0.0375(10) Uani 1 1 d . . . . .
H4AA H -0.0076 0.6267 0.2261 0.045 Uiso 1 1 calc R . . . .
H4AB H 0.1021 0.7065 0.2034 0.045 Uiso 1 1 calc R . . . .
C5A C 0.0711(5) 0.6141(3) 0.1125(2) 0.0303(9) Uani 1 1 d . . . . .
H5AA H -0.0442 0.5926 0.0959 0.036 Uiso 1 1 calc R . . . .
H5AB H 0.0895 0.6628 0.0764 0.036 Uiso 1 1 calc R . . . .
C6A C 0.3664(7) 0.5849(6) 0.1137(6) 0.030(2) Uiso 0.6 1 d D . P C 1
H6AA H 0.3698 0.6320 0.0738 0.036 Uiso 0.6 1 calc R . P C 1
H6AB H 0.4523 0.5420 0.1049 0.036 Uiso 0.6 1 calc R . P C 1
C6B C 0.3706(9) 0.5757(10) 0.1331(9) 0.041(5) Uiso 0.4 1 d D . P C 2
H6BA H 0.4124 0.6049 0.0866 0.049 Uiso 0.4 1 calc R . P C 2
H6BB H 0.4426 0.5250 0.1472 0.049 Uiso 0.4 1 calc R . P C 2
C7A C 0.3976(6) 0.6190(6) 0.2015(3) 0.0418(13) Uiso 0.6 1 d D . P C 1
H7A H 0.3973 0.6825 0.1942 0.050 Uiso 0.6 1 calc R . P C 1
C7B C 0.3940(6) 0.6360(8) 0.2064(4) 0.0418(13) Uiso 0.4 1 d D . P C 2
H7B H 0.3877 0.6982 0.1921 0.050 Uiso 0.4 1 calc R . P C 2
C8A C 0.5837(7) 0.5978(4) 0.2323(4) 0.0260(13) Uani 0.6 1 d D . P C 1
H8A H 0.6624 0.5969 0.1946 0.031 Uiso 0.6 1 calc R . P C 1
C8B C 0.5214(10) 0.6132(6) 0.2832(5) 0.032(2) Uani 0.4 1 d D . P C 2
H8B H 0.4878 0.6202 0.3359 0.038 Uiso 0.4 1 calc R . P C 2
C9A C 0.6328(10) 0.5811(5) 0.3099(4) 0.0315(15) Uiso 0.6 1 d D . P C 1
H9AA H 0.5543 0.5819 0.3477 0.038 Uiso 0.6 1 calc R . P C 1
H9AB H 0.7469 0.5681 0.3284 0.038 Uiso 0.6 1 calc R . P C 1
C9B C 0.6724(11) 0.5850(7) 0.2794(8) 0.034(2) Uiso 0.4 1 d D . P C 2
H9BA H 0.7093 0.5774 0.2276 0.041 Uiso 0.4 1 calc R . P C 2
H9BB H 0.7454 0.5720 0.3285 0.041 Uiso 0.4 1 calc R . P C 2
C10A C 0.2279(14) 0.5047(6) 0.0221(4) 0.030(2) Uiso 0.4 1 d D . P C 1
H10A H 0.3123 0.4596 0.0332 0.046 Uiso 0.4 1 calc GR . P C 1
H10B H 0.2686 0.5490 -0.0123 0.046 Uiso 0.4 1 calc GR . P C 1
H10C H 0.1238 0.4803 -0.0065 0.046 Uiso 0.4 1 calc GR . P C 1
C10B C 0.1401(8) 0.5182(4) 0.0135(3) 0.0243(13) Uiso 0.6 1 d D . P C 2
H10D H 0.2051 0.4684 0.0005 0.037 Uiso 0.6 1 calc GR . P C 2
H10E H 0.1594 0.5659 -0.0227 0.037 Uiso 0.6 1 calc GR . P C 2
H10F H 0.0207 0.5037 0.0055 0.037 Uiso 0.6 1 calc GR . P C 2
C11A C 0.0166(4) 0.4208(2) 0.1462(2) 0.0192(7) Uani 1 1 d . . . . .
H11A H -0.0115 0.4114 0.0856 0.023 Uiso 1 1 calc R . . . .
C12A C 0.0351(4) 0.3345(2) 0.1889(2) 0.0205(7) Uani 1 1 d . . . . .
C13A C -0.0236(4) 0.3223(3) 0.2630(2) 0.0243(8) Uani 1 1 d . . . . .
H13A H -0.0716 0.3687 0.2888 0.029 Uiso 1 1 calc R . . . .
C14A C -0.0120(5) 0.2409(3) 0.3001(2) 0.0274(8) Uani 1 1 d . . . . .
H14A H -0.0515 0.2347 0.3515 0.033 Uiso 1 1 calc R . . . .
C15A C 0.1088(4) 0.1838(2) 0.1950(2) 0.0222(7) Uani 1 1 d . . . . .
C16A C 0.1748(5) 0.1108(2) 0.1594(2) 0.0272(8) Uani 1 1 d . . . . .
H16A H 0.1756 0.0572 0.1867 0.033 Uiso 1 1 calc R . . . .
C17A C 0.2369(5) 0.1164(2) 0.0867(2) 0.0283(8) Uani 1 1 d . . . . .
H17A H 0.2816 0.0670 0.0641 0.034 Uiso 1 1 calc R . . . .
C18A C 0.2348(4) 0.1956(2) 0.0449(2) 0.0230(8) Uani 1 1 d . . . . .
C19A C 0.1694(4) 0.2670(2) 0.0763(2) 0.0202(7) Uani 1 1 d . . . . .
H19A H 0.1661 0.3195 0.0470 0.024 Uiso 1 1 calc R . . . .
C20A C 0.1059(4) 0.2628(2) 0.1527(2) 0.0199(7) Uani 1 1 d . . . . .
C21A C 0.2985(5) 0.2696(3) -0.0740(2) 0.0325(9) Uani 1 1 d . . . . .
H21A H 0.3435 0.2587 -0.1252 0.049 Uiso 1 1 calc GR . . . .
H21B H 0.3678 0.3125 -0.0416 0.049 Uiso 1 1 calc GR . . . .
H21C H 0.1834 0.2909 -0.0867 0.049 Uiso 1 1 calc GR . . . .
H1A H -0.206(4) 0.454(4) 0.148(3) 0.08(2) Uiso 1 1 d D . . . .
O1W O 0.5992(3) 0.40175(17) 0.09350(16) 0.0274(6) Uani 1 1 d D . . . .
H1WA H 0.607(7) 0.399(4) 0.0416(16) 0.065(18) Uiso 1 1 d D . . . .
H1WB H 0.607(7) 0.351(2) 0.115(3) 0.064(18) Uiso 1 1 d 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
F1 B1 1.425(5) . ?
F2 B1 1.389(5) . ?
F3 B1 1.378(6) . ?
F4 B1 1.360(6) . ?
F1A B1A 1.393(5) . ?
F2A B1A 1.385(5) . ?
F3A B1A 1.391(5) . ?
F4A B1A 1.386(5) . ?
O1 C11 1.418(4) . ?
O1 H1 0.87(2) . ?
O2 C18 1.372(4) . ?
O2 C21 1.428(4) . ?
N1 C1 1.539(4) . ?
N1 C5 1.513(5) . ?
N1 C6 1.520(5) . ?
N1 C10 1.495(5) . ?
N2 C14 1.314(5) . ?
N2 C15 1.372(4) . ?
C1 H1B 1.0000 . ?
C1 C2 1.546(5) . ?
C1 C11 1.530(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.532(6) . ?
C3 H3 1.0000 . ?
C3 C4 1.532(6) . ?
C3 C7 1.544(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.526(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.536(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.494(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.318(6) . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C10 H10G 0.9800 . ?
C10 H10H 0.9800 . ?
C10 H10I 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.531(5) . ?
C12 C13 1.364(5) . ?
C12 C20 1.418(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.408(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.416(5) . ?
C15 C20 1.415(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.365(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.409(5) . ?
C18 C19 1.363(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.431(5) . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
O1A C11A 1.418(4) . ?
O1A H1A 0.87(2) . ?
O2A C18A 1.371(4) . ?
O2A C21A 1.436(5) . ?
N1A C1A 1.534(5) . ?
N1A C5A 1.501(5) . ?
N1A C6A 1.509(6) . ?
N1A C6B 1.513(6) . ?
N1A C10A 1.531(6) . ?
N1A C10B 1.536(6) . ?
N2A C14A 1.311(5) . ?
N2A C15A 1.372(5) . ?
C1A H1AA 1.0000 . ?
C1A C2A 1.538(5) . ?
C1A C11A 1.539(5) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.524(6) . ?
C3A H3A 1.0000 . ?
C3A H3AA 1.0000 . ?
C3A C4A 1.523(7) . ?
C3A C7A 1.541(7) . ?
C3A C7B 1.537(7) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.510(6) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.525(8) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C6B C7B 1.521(8) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.551(7) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.551(7) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.306(7) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.307(7) . ?
C9A H9AA 0.9500 . ?
C9A H9AB 0.9500 . ?
C9B H9BA 0.9500 . ?
C9B H9BB 0.9500 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11A H11A 1.0000 . ?
C11A C12A 1.518(5) . ?
C12A C13A 1.383(5) . ?
C12A C20A 1.428(5) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.410(5) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.420(5) . ?
C15A C20A 1.415(5) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.364(6) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.416(5) . ?
C18A C19A 1.367(5) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.425(5) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
O1W H1WA 0.87(2) . ?
O1W H1WB 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
F2 B1 F1 106.8(3) . . ?
F3 B1 F1 107.8(4) . . ?
F3 B1 F2 111.0(4) . . ?
F4 B1 F1 109.4(4) . . ?
F4 B1 F2 111.0(4) . . ?
F4 B1 F3 110.8(4) . . ?
F2A B1A F1A 109.1(3) . . ?
F2A B1A F3A 110.8(4) . . ?
F2A B1A F4A 109.7(3) . . ?
F3A B1A F1A 108.9(3) . . ?
F4A B1A F1A 109.7(4) . . ?
F4A B1A F3A 108.6(3) . . ?
C11 O1 H1 103(3) . . ?
C18 O2 C21 117.0(3) . . ?
C5 N1 C1 113.3(3) . . ?
C5 N1 C6 107.6(3) . . ?
C6 N1 C1 106.3(3) . . ?
C10 N1 C1 111.8(3) . . ?
C10 N1 C5 109.4(3) . . ?
C10 N1 C6 108.2(3) . . ?
C14 N2 C15 117.5(3) . . ?
N1 C1 H1B 107.1 . . ?
N1 C1 C2 108.4(3) . . ?
C2 C1 H1B 107.1 . . ?
C11 C1 N1 113.3(3) . . ?
C11 C1 H1B 107.1 . . ?
C11 C1 C2 113.5(3) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.2(3) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3 109.7 . . ?
C2 C3 C7 110.9(3) . . ?
C4 C3 C2 109.0(3) . . ?
C4 C3 H3 109.7 . . ?
C4 C3 C7 107.7(3) . . ?
C7 C3 H3 109.7 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 C3 109.1(3) . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
N1 C5 C4 110.1(3) . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
N1 C6 C7 111.2(3) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C3 C7 H7 108.0 . . ?
C6 C7 C3 107.2(3) . . ?
C6 C7 H7 108.0 . . ?
C8 C7 C3 115.1(3) . . ?
C8 C7 C6 110.2(3) . . ?
C8 C7 H7 108.0 . . ?
C7 C8 H8 118.3 . . ?
C9 C8 C7 123.4(4) . . ?
C9 C8 H8 118.3 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
N1 C10 H10G 109.5 . . ?
N1 C10 H10H 109.5 . . ?
N1 C10 H10I 109.5 . . ?
H10G C10 H10H 109.5 . . ?
H10G C10 H10I 109.5 . . ?
H10H C10 H10I 109.5 . . ?
O1 C11 C1 108.4(3) . . ?
O1 C11 H11 108.8 . . ?
O1 C11 C12 111.3(3) . . ?
C1 C11 H11 108.8 . . ?
C1 C11 C12 110.8(3) . . ?
C12 C11 H11 108.8 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 C20 118.5(3) . . ?
C20 C12 C11 122.1(3) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
N2 C14 C13 123.4(3) . . ?
N2 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N2 C15 C16 117.3(3) . . ?
N2 C15 C20 122.9(3) . . ?
C20 C15 C16 119.8(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
O2 C18 C17 114.3(3) . . ?
C19 C18 O2 124.1(3) . . ?
C19 C18 C17 121.5(3) . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C12 C20 C19 124.1(3) . . ?
C15 C20 C12 117.5(3) . . ?
C15 C20 C19 118.4(3) . . ?
O2 C21 H21D 109.5 . . ?
O2 C21 H21E 109.5 . . ?
O2 C21 H21F 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C11A O1A H1A 108(4) . . ?
C18A O2A C21A 116.8(3) . . ?
C1A N1A C10B 112.2(3) . . ?
C5A N1A C1A 112.5(3) . . ?
C5A N1A C6A 107.3(4) . . ?
C5A N1A C6B 109.9(6) . . ?
C5A N1A C10A 125.7(5) . . ?
C5A N1A C10B 100.7(4) . . ?
C6A N1A C1A 112.8(5) . . ?
C6A N1A C10A 89.8(5) . . ?
C6B N1A C1A 100.4(7) . . ?
C6B N1A C10B 121.6(6) . . ?
C10A N1A C1A 106.6(5) . . ?
C14A N2A C15A 116.7(3) . . ?
N1A C1A H1AA 107.2 . . ?
N1A C1A C2A 107.4(3) . . ?
N1A C1A C11A 113.4(3) . . ?
C2A C1A H1AA 107.2 . . ?
C2A C1A C11A 114.0(3) . . ?
C11A C1A H1AA 107.2 . . ?
C1A C2A H2AA 109.6 . . ?
C1A C2A H2AB 109.6 . . ?
H2AA C2A H2AB 108.1 . . ?
C3A C2A C1A 110.3(3) . . ?
C3A C2A H2AA 109.6 . . ?
C3A C2A H2AB 109.6 . . ?
C2A C3A H3A 110.5 . . ?
C2A C3A H3AA 108.2 . . ?
C2A C3A C7A 107.6(5) . . ?
C2A C3A C7B 118.0(6) . . ?
C4A C3A C2A 108.7(4) . . ?
C4A C3A H3A 110.5 . . ?
C4A C3A H3AA 108.2 . . ?
C4A C3A C7A 109.1(4) . . ?
C4A C3A C7B 105.1(4) . . ?
C7A C3A H3A 110.5 . . ?
C7B C3A H3AA 108.2 . . ?
C3A C4A H4AA 109.8 . . ?
C3A C4A H4AB 109.8 . . ?
H4AA C4A H4AB 108.2 . . ?
C5A C4A C3A 109.4(3) . . ?
C5A C4A H4AA 109.8 . . ?
C5A C4A H4AB 109.8 . . ?
N1A C5A C4A 109.5(3) . . ?
N1A C5A H5AA 109.8 . . ?
N1A C5A H5AB 109.8 . . ?
C4A C5A H5AA 109.8 . . ?
C4A C5A H5AB 109.8 . . ?
H5AA C5A H5AB 108.2 . . ?
N1A C6A H6AA 110.5 . . ?
N1A C6A H6AB 110.5 . . ?
N1A C6A C7A 106.1(5) . . ?
H6AA C6A H6AB 108.7 . . ?
C7A C6A H6AA 110.5 . . ?
C7A C6A H6AB 110.5 . . ?
N1A C6B H6BA 108.0 . . ?
N1A C6B H6BB 108.0 . . ?
N1A C6B C7B 117.3(7) . . ?
H6BA C6B H6BB 107.2 . . ?
C7B C6B H6BA 108.0 . . ?
C7B C6B H6BB 108.0 . . ?
C3A C7A H7A 103.7 . . ?
C3A C7A C8A 126.3(4) . . ?
C6A C7A C3A 112.2(5) . . ?
C6A C7A H7A 103.7 . . ?
C6A C7A C8A 104.8(5) . . ?
C8A C7A H7A 103.7 . . ?
C3A C7B H7B 114.8 . . ?
C3A C7B C8B 91.1(4) . . ?
C6B C7B C3A 97.3(8) . . ?
C6B C7B H7B 114.8 . . ?
C6B C7B C8B 119.7(9) . . ?
C8B C7B H7B 114.8 . . ?
C7A C8A H8A 119.8 . . ?
C9A C8A C7A 120.3(6) . . ?
C9A C8A H8A 119.8 . . ?
C7B C8B H8B 118.2 . . ?
C9B C8B C7B 123.5(9) . . ?
C9B C8B H8B 118.2 . . ?
C8A C9A H9AA 120.0 . . ?
C8A C9A H9AB 120.0 . . ?
H9AA C9A H9AB 120.0 . . ?
C8B C9B H9BA 120.0 . . ?
C8B C9B H9BB 120.0 . . ?
H9BA C9B H9BB 120.0 . . ?
N1A C10A H10A 109.5 . . ?
N1A C10A H10B 109.5 . . ?
N1A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N1A C10B H10D 109.5 . . ?
N1A C10B H10E 109.5 . . ?
N1A C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
O1A C11A C1A 108.4(3) . . ?
O1A C11A H11A 108.7 . . ?
O1A C11A C12A 112.5(3) . . ?
C1A C11A H11A 108.7 . . ?
C12A C11A C1A 109.7(3) . . ?
C12A C11A H11A 108.7 . . ?
C13A C12A C11A 120.4(3) . . ?
C13A C12A C20A 117.8(3) . . ?
C20A C12A C11A 121.7(3) . . ?
C12A C13A H13A 120.1 . . ?
C12A C13A C14A 119.8(4) . . ?
C14A C13A H13A 120.1 . . ?
N2A C14A C13A 124.4(3) . . ?
N2A C14A H14A 117.8 . . ?
C13A C14A H14A 117.8 . . ?
N2A C15A C16A 117.5(3) . . ?
N2A C15A C20A 123.9(3) . . ?
C20A C15A C16A 118.6(3) . . ?
C15A C16A H16A 119.5 . . ?
C17A C16A C15A 121.1(3) . . ?
C17A C16A H16A 119.5 . . ?
C16A C17A H17A 120.0 . . ?
C16A C17A C18A 120.1(4) . . ?
C18A C17A H17A 120.0 . . ?
O2A C18A C17A 113.9(3) . . ?
C19A C18A O2A 125.5(3) . . ?
C19A C18A C17A 120.6(3) . . ?
C18A C19A H19A 119.9 . . ?
C18A C19A C20A 120.2(3) . . ?
C20A C19A H19A 119.9 . . ?
C15A C20A C12A 117.4(3) . . ?
C15A C20A C19A 119.4(3) . . ?
C19A C20A C12A 123.2(3) . . ?
O2A C21A H21A 109.5 . . ?
O2A C21A H21B 109.5 . . ?
O2A C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
H1WA O1W H1WB 111(6) . . ?

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
O1 H1 F1 0.87(2) 1.97(3) 2.812(3) 166(4) .
O1A H1A O1W 0.87(2) 1.88(3) 2.740(4) 173(6) 1_455
O1W H1WA F1 0.87(2) 2.03(3) 2.881(4) 168(6) 1_554
O1W H1WB N2 0.87(2) 1.88(3) 2.750(4) 179(6) 2_646

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C11 O1 -70.8(3) . . . . ?
C1 C2 C3 C4 56.7(4) . . . . ?
C1 C2 C3 C7 -61.7(4) . . . . ?
C1 C11 C12 C13 107.5(4) . . . . ?
C1 C11 C12 C20 -75.4(4) . . . . ?
C2 C1 N1 C5 -59.5(4) . . . . ?
C2 C1 N1 C6 58.4(3) . . . . ?
C2 C1 N1 C10 176.3(3) . . . . ?
C2 C1 C11 O1 53.4(4) . . . . ?
C2 C1 C11 C12 -68.9(4) . . . . ?
C2 C3 C4 C5 -66.3(4) . . . . ?
C2 C3 C7 C6 51.5(4) . . . . ?
C2 C3 C7 C8 -71.5(4) . . . . ?
C3 C2 C1 N1 4.0(4) . . . . ?
C3 C2 C1 C11 -122.9(3) . . . . ?
C3 C4 C5 N1 11.8(5) . . . . ?
C3 C7 C6 N1 12.8(4) . . . . ?
C3 C7 C8 C9 -110.8(4) . . . . ?
C4 C3 C7 C6 -67.8(4) . . . . ?
C4 C3 C7 C8 169.2(3) . . . . ?
C4 C5 N1 C1 50.7(4) . . . . ?
C4 C5 N1 C6 -66.5(4) . . . . ?
C4 C5 N1 C10 176.1(3) . . . . ?
C5 C4 C3 C7 54.1(4) . . . . ?
C6 C7 C8 C9 127.8(4) . . . . ?
C7 C6 N1 C1 -69.7(3) . . . . ?
C7 C6 N1 C5 52.0(4) . . . . ?
C7 C6 N1 C10 170.1(3) . . . . ?
C8 C7 C6 N1 138.7(3) . . . . ?
C11 C1 N1 C5 67.4(4) . . . . ?
C11 C1 N1 C6 -174.6(3) . . . . ?
C11 C1 N1 C10 -56.7(4) . . . . ?
C12 C11 C1 N1 166.9(3) . . . . ?
C13 C12 C11 O1 -13.2(4) . . . . ?
C17 C18 O2 C21 169.4(3) . . . . ?
C19 C18 O2 C21 -10.0(5) . . . . ?
C20 C12 C11 O1 163.9(3) . . . . ?
N1A C1A C11A O1A -74.2(3) . . . . ?
C1A C11A C12A C13A 100.0(4) . . . . ?
C1A C11A C12A C20A -82.8(4) . . . . ?
C2A C1A C11A O1A 49.1(4) . . . . ?
C2A C1A C11A C12A -74.0(4) . . . . ?
C3A C2A C1A N1A 3.2(5) . . . . ?
C3A C2A C1A C11A -123.3(4) . . . . ?
C12A C11A C1A N1A 162.7(3) . . . . ?
C13A C12A C11A O1A -20.8(5) . . . . ?
C20A C12A C11A O1A 156.4(3) . . . . ?

_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_Me2Qn_17srv202
_database_code_depnum_ccdc_archive 'CCDC 1985988'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2020-02-24 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2017-08-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(B F4), C22 H30 N2 O2'
_chemical_formula_sum            'C22 H30 B2 F8 N2 O2'
_chemical_formula_weight         528.10
_chemical_absolute_configuration ad
_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 0.0181 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'
B B 0.0090 0.0039 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.6961(3)
_cell_length_b                   10.2407(3)
_cell_length_c                   23.6533(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2348.65(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      74.48
_cell_measurement_theta_min      3.74
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    1.195
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0883 before and 0.0471 after correction. 
The Ratio of minimum to maximum transmission is 0.8778. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27372
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.468
_diffrn_reflns_theta_min         3.737
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4411
_reflns_number_total             4554
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         4554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.067
_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)+(0.0330P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0651
_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
F1 F 0.00225(13) 0.67925(13) 0.45672(5) 0.0342(3) Uani 1 1 d . . . . .
F2 F 0.21356(12) 0.67705(12) 0.49781(5) 0.0322(3) Uani 1 1 d . . . . .
F3 F 0.02555(14) 0.73557(13) 0.54922(5) 0.0377(3) Uani 1 1 d . . . . .
F4 F 0.05660(14) 0.52419(12) 0.52173(6) 0.0378(3) Uani 1 1 d . . . . .
B1 B 0.0734(2) 0.6544(2) 0.50688(9) 0.0236(4) Uani 1 1 d . . . . .
F5 F 0.59403(13) 0.51518(12) 0.67169(5) 0.0327(3) Uani 1 1 d . . . . .
F6 F 0.81417(13) 0.44283(15) 0.67660(5) 0.0412(3) Uani 1 1 d . . . . .
F7 F 0.69877(13) 0.49848(13) 0.75681(5) 0.0362(3) Uani 1 1 d . . . . .
F8 F 0.63772(14) 0.31504(11) 0.70792(5) 0.0345(3) Uani 1 1 d . . . . .
B2 B 0.6869(2) 0.4416(2) 0.70330(9) 0.0226(4) Uani 1 1 d . . . . .
O1 O 0.35231(13) 0.54639(13) 0.40969(6) 0.0227(3) Uani 1 1 d . . . . .
O2 O -0.29723(14) 0.36533(16) 0.41068(7) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.19834(16) 0.61718(14) 0.29655(7) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.18751(19) 0.09305(15) 0.44419(7) 0.0256(4) Uani 1 1 d . . . . .
C1 C 0.22640(17) 0.48527(16) 0.32510(7) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.36107(19) 0.42932(17) 0.29997(8) 0.0195(4) Uani 1 1 d . . . . .
C3 C 0.42923(19) 0.52798(19) 0.26075(8) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.4511(2) 0.6567(2) 0.29240(10) 0.0325(5) Uani 1 1 d . . . . .
C5 C 0.3116(2) 0.71561(18) 0.30739(9) 0.0281(4) Uani 1 1 d . . . . .
C6 C 0.1911(2) 0.59092(19) 0.23312(8) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.3343(2) 0.5555(2) 0.20984(8) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.3385(2) 0.4471(2) 0.16751(9) 0.0318(5) Uani 1 1 d . . . . .
C9 C 0.2365(3) 0.3731(2) 0.14960(11) 0.0383(5) Uani 1 1 d . . . . .
C10 C 0.0623(2) 0.6727(2) 0.31445(9) 0.0267(4) Uani 1 1 d . . . . .
C11 C 0.22680(18) 0.49191(17) 0.39035(7) 0.0170(3) Uani 1 1 d . . . . .
C12 C 0.20890(19) 0.35264(17) 0.41201(7) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.3235(2) 0.28026(18) 0.42538(8) 0.0226(4) Uani 1 1 d . . . . .
C14 C 0.3101(2) 0.14966(19) 0.44081(8) 0.0262(4) Uani 1 1 d . . . . .
C15 C 0.0675(2) 0.16144(18) 0.43412(7) 0.0237(4) Uani 1 1 d . . . . .
C16 C -0.0630(2) 0.1010(2) 0.43976(8) 0.0301(5) Uani 1 1 d . . . . .
C17 C -0.1797(2) 0.1710(2) 0.43084(9) 0.0318(5) Uani 1 1 d . . . . .
C18 C -0.1736(2) 0.3049(2) 0.41539(8) 0.0263(4) Uani 1 1 d . . . . .
C19 C -0.0478(2) 0.36418(19) 0.40776(8) 0.0221(4) Uani 1 1 d . . . . .
C20 C 0.0759(2) 0.29458(17) 0.41730(7) 0.0194(4) Uani 1 1 d . . . . .
C21 C -0.2956(2) 0.5006(2) 0.39436(9) 0.0323(5) Uani 1 1 d . . . . .
C22 C 0.1816(3) -0.0485(2) 0.45752(10) 0.0362(5) Uani 1 1 d . . . . .
H1 H 0.329(3) 0.596(3) 0.4374(13) 0.046(8) Uiso 1 1 d . . . . .
H1A H 0.148(2) 0.434(2) 0.3139(9) 0.017(5) Uiso 1 1 d . . . . .
H2A H 0.337(2) 0.349(2) 0.2801(10) 0.026(6) Uiso 1 1 d . . . . .
H2B H 0.427(2) 0.411(2) 0.3303(10) 0.020(5) Uiso 1 1 d . . . . .
H3 H 0.515(2) 0.495(2) 0.2471(9) 0.022(5) Uiso 1 1 d . . . . .
H4A H 0.503(3) 0.641(3) 0.3282(13) 0.046(8) Uiso 1 1 d . . . . .
H4B H 0.501(3) 0.716(3) 0.2675(11) 0.037(7) Uiso 1 1 d . . . . .
H5A H 0.300(2) 0.740(2) 0.3476(10) 0.023(5) Uiso 1 1 d . . . . .
H5B H 0.287(3) 0.791(3) 0.2853(11) 0.031(6) Uiso 1 1 d . . . . .
H6A H 0.123(3) 0.520(3) 0.2285(10) 0.030(6) Uiso 1 1 d . . . . .
H6B H 0.158(3) 0.672(2) 0.2155(10) 0.028(6) Uiso 1 1 d . . . . .
H7 H 0.367(3) 0.635(3) 0.1895(11) 0.039(7) Uiso 1 1 d . . . . .
H8 H 0.436(3) 0.433(3) 0.1505(12) 0.047(8) Uiso 1 1 d . . . . .
H9A H 0.255(2) 0.308(2) 0.1228(10) 0.025(6) Uiso 1 1 d . . . . .
H9B H 0.142(4) 0.383(3) 0.1625(15) 0.062(9) Uiso 1 1 d . . . . .
H10A H 0.050(2) 0.752(2) 0.2924(10) 0.025(6) Uiso 1 1 d . . . . .
H10B H 0.068(3) 0.694(3) 0.3545(11) 0.034(6) Uiso 1 1 d . . . . .
H10C H -0.011(3) 0.606(3) 0.3060(10) 0.030(6) Uiso 1 1 d . . . . .
H11 H 0.152(2) 0.542(2) 0.4045(8) 0.014(5) Uiso 1 1 d . . . . .
H13 H 0.417(2) 0.319(2) 0.4240(9) 0.022(5) Uiso 1 1 d . . . . .
H14 H 0.383(3) 0.099(3) 0.4490(10) 0.029(6) Uiso 1 1 d . . . . .
H16 H -0.065(3) 0.009(3) 0.4511(11) 0.041(7) Uiso 1 1 d . . . . .
H17 H -0.268(3) 0.130(3) 0.4342(11) 0.037(7) Uiso 1 1 d . . . . .
H19 H -0.042(2) 0.456(2) 0.3986(8) 0.015(5) Uiso 1 1 d . . . . .
H21A H -0.395(3) 0.533(3) 0.3991(11) 0.037(7) Uiso 1 1 d . . . . .
H21B H -0.266(3) 0.510(3) 0.3555(12) 0.040(7) Uiso 1 1 d . . . . .
H21C H -0.234(3) 0.557(3) 0.4214(12) 0.041(7) Uiso 1 1 d . . . . .
H22A H 0.121(3) -0.062(2) 0.4904(12) 0.038(7) Uiso 1 1 d . . . . .
H22B H 0.133(3) -0.095(2) 0.4276(11) 0.030(6) Uiso 1 1 d . . . . .
H22C H 0.279(3) -0.078(3) 0.4643(13) 0.050(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
F1 B1 1.396(3) . ?
F2 B1 1.395(3) . ?
F3 B1 1.382(2) . ?
F4 B1 1.388(2) . ?
F5 B2 1.392(2) . ?
F6 B2 1.387(3) . ?
F7 B2 1.398(2) . ?
F8 B2 1.385(2) . ?
O1 C11 1.415(2) . ?
O1 H1 0.86(3) . ?
O2 C18 1.354(3) . ?
O2 C21 1.439(3) . ?
N1 C1 1.535(2) . ?
N1 C5 1.513(2) . ?
N1 C6 1.526(2) . ?
N1 C10 1.498(2) . ?
N2 C14 1.325(3) . ?
N2 C15 1.379(3) . ?
N2 C22 1.485(2) . ?
C1 C2 1.545(2) . ?
C1 C11 1.545(2) . ?
C1 H1A 0.96(2) . ?
C2 C3 1.523(2) . ?
C2 H2A 0.98(2) . ?
C2 H2B 0.98(2) . ?
C3 C4 1.531(3) . ?
C3 C7 1.542(3) . ?
C3 H3 0.96(2) . ?
C4 C5 1.523(3) . ?
C4 H4A 1.00(3) . ?
C4 H4B 0.97(3) . ?
C5 H5A 0.99(2) . ?
C5 H5B 0.97(3) . ?
C6 C7 1.537(3) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.98(3) . ?
C7 C8 1.495(3) . ?
C7 H7 1.00(3) . ?
C8 C9 1.317(3) . ?
C8 H8 1.04(3) . ?
C9 H9A 0.93(3) . ?
C9 H9B 0.97(4) . ?
C10 H10A 0.97(2) . ?
C10 H10B 0.97(3) . ?
C10 H10C 1.01(3) . ?
C11 C12 1.525(2) . ?
C11 H11 0.95(2) . ?
C12 C13 1.373(3) . ?
C12 C20 1.425(3) . ?
C13 C14 1.392(3) . ?
C13 H13 0.99(2) . ?
C14 H14 0.90(3) . ?
C15 C16 1.415(3) . ?
C15 C20 1.423(3) . ?
C16 C17 1.356(3) . ?
C16 H16 0.97(3) . ?
C17 C18 1.420(3) . ?
C17 H17 0.95(3) . ?
C18 C19 1.374(3) . ?
C19 C20 1.413(3) . ?
C19 H19 0.96(2) . ?
C21 H21A 1.03(3) . ?
C21 H21B 0.97(3) . ?
C21 H21C 1.05(3) . ?
C22 H22A 0.98(3) . ?
C22 H22B 0.97(3) . ?
C22 H22C 1.01(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
F2 B1 F1 108.68(17) . . ?
F3 B1 F1 109.88(17) . . ?
F3 B1 F2 109.77(17) . . ?
F3 B1 F4 110.80(17) . . ?
F4 B1 F1 109.42(17) . . ?
F4 B1 F2 108.25(17) . . ?
F5 B2 F7 108.29(16) . . ?
F6 B2 F5 109.01(16) . . ?
F6 B2 F7 109.56(16) . . ?
F8 B2 F5 109.07(16) . . ?
F8 B2 F6 110.54(17) . . ?
F8 B2 F7 110.31(16) . . ?
C11 O1 H1 105(2) . . ?
C18 O2 C21 116.91(16) . . ?
C5 N1 C1 112.53(14) . . ?
C5 N1 C6 108.50(15) . . ?
C6 N1 C1 106.60(13) . . ?
C10 N1 C1 111.46(14) . . ?
C10 N1 C5 109.81(15) . . ?
C10 N1 C6 107.73(15) . . ?
C14 N2 C15 121.63(16) . . ?
C14 N2 C22 118.35(19) . . ?
C15 N2 C22 119.99(19) . . ?
N1 C1 C2 107.88(13) . . ?
N1 C1 C11 113.66(14) . . ?
N1 C1 H1A 102.6(13) . . ?
C2 C1 H1A 111.0(12) . . ?
C11 C1 C2 113.49(14) . . ?
C11 C1 H1A 107.6(12) . . ?
C1 C2 H2A 107.1(14) . . ?
C1 C2 H2B 110.0(13) . . ?
C3 C2 C1 110.81(14) . . ?
C3 C2 H2A 111.9(14) . . ?
C3 C2 H2B 107.0(13) . . ?
H2A C2 H2B 110.1(19) . . ?
C2 C3 C4 109.50(17) . . ?
C2 C3 C7 109.77(15) . . ?
C2 C3 H3 110.3(14) . . ?
C4 C3 C7 107.90(16) . . ?
C4 C3 H3 110.6(14) . . ?
C7 C3 H3 108.7(13) . . ?
C3 C4 H4A 110.2(17) . . ?
C3 C4 H4B 108.1(15) . . ?
C5 C4 C3 109.36(17) . . ?
C5 C4 H4A 108.1(17) . . ?
C5 C4 H4B 109.3(16) . . ?
H4A C4 H4B 112(2) . . ?
N1 C5 C4 109.98(15) . . ?
N1 C5 H5A 104.3(14) . . ?
N1 C5 H5B 105.3(15) . . ?
C4 C5 H5A 114.9(14) . . ?
C4 C5 H5B 114.3(15) . . ?
H5A C5 H5B 107(2) . . ?
N1 C6 C7 110.65(15) . . ?
N1 C6 H6A 105.7(14) . . ?
N1 C6 H6B 106.3(14) . . ?
C7 C6 H6A 113.1(14) . . ?
C7 C6 H6B 110.1(14) . . ?
H6A C6 H6B 111(2) . . ?
C3 C7 H7 109.6(16) . . ?
C6 C7 C3 107.60(15) . . ?
C6 C7 H7 105.5(16) . . ?
C8 C7 C3 111.79(17) . . ?
C8 C7 C6 116.08(18) . . ?
C8 C7 H7 105.9(15) . . ?
C7 C8 H8 112.9(16) . . ?
C9 C8 C7 128.5(2) . . ?
C9 C8 H8 118.6(16) . . ?
C8 C9 H9A 118.9(15) . . ?
C8 C9 H9B 123(2) . . ?
H9A C9 H9B 118(3) . . ?
N1 C10 H10A 106.0(14) . . ?
N1 C10 H10B 107.9(16) . . ?
N1 C10 H10C 107.9(14) . . ?
H10A C10 H10B 110(2) . . ?
H10A C10 H10C 111.9(19) . . ?
H10B C10 H10C 113(2) . . ?
O1 C11 C1 110.03(14) . . ?
O1 C11 C12 110.98(14) . . ?
O1 C11 H11 108.9(12) . . ?
C1 C11 H11 112.1(12) . . ?
C12 C11 C1 107.11(14) . . ?
C12 C11 H11 107.7(12) . . ?
C13 C12 C11 119.35(16) . . ?
C13 C12 C20 119.13(16) . . ?
C20 C12 C11 121.49(16) . . ?
C12 C13 C14 120.24(19) . . ?
C12 C13 H13 121.0(14) . . ?
C14 C13 H13 118.8(14) . . ?
N2 C14 C13 121.32(19) . . ?
N2 C14 H14 115.7(16) . . ?
C13 C14 H14 123.0(16) . . ?
N2 C15 C16 121.08(17) . . ?
N2 C15 C20 119.13(18) . . ?
C16 C15 C20 119.79(19) . . ?
C15 C16 H16 117.7(16) . . ?
C17 C16 C15 120.03(18) . . ?
C17 C16 H16 122.3(16) . . ?
C16 C17 C18 121.03(19) . . ?
C16 C17 H17 120.0(16) . . ?
C18 C17 H17 118.9(16) . . ?
O2 C18 C17 115.19(17) . . ?
O2 C18 C19 124.95(19) . . ?
C19 C18 C17 119.84(19) . . ?
C18 C19 C20 120.61(17) . . ?
C18 C19 H19 121.0(13) . . ?
C20 C19 H19 118.3(13) . . ?
C15 C20 C12 118.43(17) . . ?
C19 C20 C12 122.92(16) . . ?
C19 C20 C15 118.64(17) . . ?
O2 C21 H21A 105.7(15) . . ?
O2 C21 H21B 110.9(17) . . ?
O2 C21 H21C 112.0(15) . . ?
H21A C21 H21B 110(2) . . ?
H21A C21 H21C 107(2) . . ?
H21B C21 H21C 111(2) . . ?
N2 C22 H22A 108.9(15) . . ?
N2 C22 H22B 109.8(15) . . ?
N2 C22 H22C 107.0(17) . . ?
H22A C22 H22B 103(2) . . ?
H22A C22 H22C 113(2) . . ?
H22B C22 H22C 115(2) . . ?

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
O1 H1 F2 0.86(3) 1.99(3) 2.8187(18) 160(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C11 O1 -77.26(17) . . . . ?
C1 C2 C3 C4 54.7(2) . . . . ?
C1 C2 C3 C7 -63.6(2) . . . . ?
C1 C11 C12 C13 94.42(18) . . . . ?
C1 C11 C12 C20 -83.90(19) . . . . ?
C2 C1 N1 C5 -61.53(19) . . . . ?
C2 C1 N1 C6 57.30(17) . . . . ?
C2 C1 N1 C10 174.60(15) . . . . ?
C2 C1 C11 O1 46.52(19) . . . . ?
C2 C1 C11 C12 -74.20(18) . . . . ?
C2 C3 C4 C5 -65.0(2) . . . . ?
C2 C3 C7 C6 51.7(2) . . . . ?
C2 C3 C7 C8 -76.9(2) . . . . ?
C3 C2 C1 N1 6.2(2) . . . . ?
C3 C2 C1 C11 -120.63(17) . . . . ?
C3 C4 C5 N1 10.9(2) . . . . ?
C3 C7 C6 N1 12.8(2) . . . . ?
C3 C7 C8 C9 120.0(2) . . . . ?
C4 C3 C7 C6 -67.6(2) . . . . ?
C4 C3 C7 C8 163.85(17) . . . . ?
C4 C5 N1 C1 52.0(2) . . . . ?
C4 C5 N1 C6 -65.7(2) . . . . ?
C4 C5 N1 C10 176.77(17) . . . . ?
C5 C4 C3 C7 54.4(2) . . . . ?
C6 C7 C8 C9 -3.9(3) . . . . ?
C7 C6 N1 C1 -69.71(19) . . . . ?
C7 C6 N1 C5 51.7(2) . . . . ?
C7 C6 N1 C10 170.55(16) . . . . ?
C8 C7 C6 N1 138.86(17) . . . . ?
C11 C1 N1 C5 65.25(19) . . . . ?
C11 C1 N1 C6 -175.93(14) . . . . ?
C11 C1 N1 C10 -58.63(19) . . . . ?
C12 C11 C1 N1 162.02(14) . . . . ?
C13 C12 C11 O1 -25.7(2) . . . . ?
C17 C18 O2 C21 -179.21(17) . . . . ?
C19 C18 O2 C21 2.5(3) . . . . ?
C20 C12 C11 O1 155.98(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instruction_details 
;
TITL 17srv202
CELL 1.54178 9.6961 10.2407 23.6533 90 90 90
ZERR 4 0.0003 0.0003 0.0008 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H B F N O
UNIT 88 120 8 32 8 8

L.S. 9
PLAN  5
SIZE 0.12 0.28 0.39
TEMP -153.15
HTAB O1 F2
CONF C2 C1 N1 C5
CONF C11 C1 N1 C5
CONF C2 C1 N1 C6
CONF C11 C1 N1 C6
CONF C2 C1 N1 C10
CONF C11 C1 N1 C10
CONF C3 C2 C1 N1
CONF C3 C2 C1 C11
CONF C1 C2 C3 C4
CONF C1 C2 C3 C7
CONF C2 C3 C4 C5
CONF C5 C4 C3 C7
CONF C3 C4 C5 N1
CONF C4 C5 N1 C1
CONF C4 C5 N1 C6
CONF C4 C5 N1 C10
CONF C7 C6 N1 C1
CONF C7 C6 N1 C5
CONF C7 C6 N1 C10
CONF C3 C7 C6 N1
CONF C8 C7 C6 N1
CONF C2 C3 C7 C6
CONF C4 C3 C7 C6
CONF C2 C3 C7 C8
CONF C4 C3 C7 C8
CONF C3 C7 C8 C9
CONF C6 C7 C8 C9
CONF N1 C1 C11 O1
CONF C2 C1 C11 O1
CONF C12 C11 C1 N1
CONF C2 C1 C11 C12
CONF C13 C12 C11 O1
CONF C1 C11 C12 C13
CONF C20 C12 C11 O1
CONF C1 C11 C12 C20
CONF C17 C18 O2 C21
CONF C19 C18 O2 C21
BOND $h
fmap 2
acta 
OMIT -2 145
OMIT 8 7 7
WGHT 0.033 0.5
FVAR 0.29601
REM <olex2.extras>
REM <HklSrc "%.\\17srv202.hkl">
REM </olex2.extras>

F1    4     0.00225  0.67925  0.45672  11.00000  0.03601  0.03615  0.03044 =
 -0.00444 -0.00296  0.01038 
F2    4     0.21355  0.67705  0.49781  11.00000  0.02736  0.03086  0.03853 =
 -0.00628  0.00721 -0.00556 
F3    4     0.02555  0.73557  0.54922  11.00000  0.03761  0.04147  0.03409 =
 -0.01514  0.00443  0.00805 
F4    4     0.05660  0.52419  0.52173  11.00000  0.04377  0.02376  0.04576 =
 0.00534  0.00149 -0.00935 
B1    3     0.07340  0.65436  0.50688  11.00000  0.02618  0.01972  0.02501 =
 -0.00210  0.00279 -0.00093 

F5    4     0.59403  0.51519  0.67169  11.00000  0.03375  0.03014  0.03417 =
 0.00418 -0.00515  0.00382 
F6    4     0.81417  0.44283  0.67659  11.00000  0.02205  0.06790  0.03362 =
 -0.01290  0.00152 -0.00524 
F7    4     0.69877  0.49848  0.75681  11.00000  0.04665  0.03997  0.02210 =
 -0.00667  0.00008 -0.01061 
F8    4     0.63772  0.31504  0.70792  11.00000  0.04292  0.01923  0.04136 =
 -0.00319  0.00263  0.00158 
B2    3     0.68685  0.44156  0.70330  11.00000  0.02108  0.02303  0.02367 =
 -0.00299 -0.00030 -0.00216 

O1    6     0.35231  0.54639  0.40969  11.00000  0.01845  0.02080  0.02885 =
 -0.00614 -0.00197 -0.00256 
O2    6    -0.29723  0.36533  0.41068  11.00000  0.01891  0.04546  0.03585 =
 -0.00420  0.00431 -0.00662 
N1    5     0.19834  0.61718  0.29655  11.00000  0.01942  0.01377  0.02485 =
 0.00134 -0.00050  0.00234 
N2    5     0.18751  0.09305  0.44419  11.00000  0.04251  0.01675  0.01744 =
 0.00148 -0.00136  0.00084 
C1    1     0.22640  0.48527  0.32510  11.00000  0.01602  0.01119  0.02240 =
 0.00047 -0.00015 -0.00058 
C2    1     0.36107  0.42932  0.29997  11.00000  0.01911  0.01694  0.02255 =
 0.00184  0.00253  0.00287 
C3    1     0.42923  0.52798  0.26076  11.00000  0.01692  0.02640  0.03221 =
 0.00771  0.00571  0.00235 
C4    1     0.45115  0.65674  0.29240  11.00000  0.02410  0.02534  0.04819 =
 0.00743 -0.00077 -0.00770 
C5    1     0.31162  0.71561  0.30739  11.00000  0.03231  0.01417  0.03791 =
 0.00368 -0.00433 -0.00631 
C6    1     0.19115  0.59092  0.23312  11.00000  0.02413  0.02368  0.02233 =
 0.00305 -0.00004  0.00480 
C7    1     0.33434  0.55550  0.20984  11.00000  0.02671  0.02887  0.02729 =
 0.00714  0.00472  0.00580 
C8    1     0.33853  0.44712  0.16751  11.00000  0.03201  0.03591  0.02760 =
 0.00641  0.00664  0.00989 
C9    1     0.23646  0.37307  0.14960  11.00000  0.04013  0.03288  0.04175 =
 -0.00237  0.00658  0.00089 
C10   1     0.06226  0.67268  0.31445  11.00000  0.02596  0.02382  0.03042 =
 0.00040  0.00217  0.01244 
C11   1     0.22680  0.49191  0.39035  11.00000  0.01469  0.01403  0.02238 =
 -0.00198  0.00059 -0.00059 
C12   1     0.20890  0.35263  0.41201  11.00000  0.02301  0.01670  0.01551 =
 -0.00255  0.00133 -0.00009 
C13   1     0.32349  0.28026  0.42538  11.00000  0.02592  0.02185  0.02003 =
 -0.00128 -0.00224  0.00348 
C14   1     0.31010  0.14966  0.44081  11.00000  0.03571  0.02281  0.02023 =
 -0.00072 -0.00414  0.00703 
C15   1     0.06751  0.16144  0.43412  11.00000  0.03622  0.01941  0.01551 =
 -0.00221  0.00209 -0.00339 
C16   1    -0.06296  0.10102  0.43976  11.00000  0.04386  0.02355  0.02297 =
 -0.00244  0.00613 -0.01222 
C17   1    -0.17969  0.17103  0.43084  11.00000  0.03410  0.03488  0.02644 =
 -0.00576  0.00847 -0.01840 
C18   1    -0.17356  0.30486  0.41539  11.00000  0.02342  0.03358  0.02186 =
 -0.00603  0.00310 -0.00774 
C19   1    -0.04780  0.36418  0.40776  11.00000  0.02276  0.02155  0.02184 =
 -0.00179  0.00379 -0.00382 
C20   1     0.07591  0.29458  0.41730  11.00000  0.02593  0.01771  0.01455 =
 -0.00207  0.00175 -0.00240 
C21   1    -0.29556  0.50064  0.39436  11.00000  0.02087  0.04672  0.02942 =
 -0.00002  0.00285  0.00413 
C22   1     0.18156 -0.04854  0.45752  11.00000  0.06195  0.01683  0.02994 =
 0.00538 -0.00409 -0.00129 
H1    2     0.32891  0.59639  0.43738  11.00000  0.04643 
H1a   2     0.14817  0.43410  0.31385  11.00000  0.01714 
H2a   2     0.33677  0.34865  0.28013  11.00000  0.02629 
H2b   2     0.42699  0.41059  0.33030  11.00000  0.02011 
H3    2     0.51527  0.49450  0.24708  11.00000  0.02170 
H4a   2     0.50259  0.64095  0.32819  11.00000  0.04555 
H4b   2     0.50061  0.71621  0.26750  11.00000  0.03724 
H5a   2     0.30019  0.73953  0.34764  11.00000  0.02312 
H5b   2     0.28699  0.79139  0.28528  11.00000  0.03132 
H6a   2     0.12309  0.52034  0.22846  11.00000  0.02995 
H6b   2     0.15789  0.67222  0.21553  11.00000  0.02801 
H7    2     0.36715  0.63500  0.18953  11.00000  0.03936 
H8    2     0.43632  0.43257  0.15053  11.00000  0.04709 
H9a   2     0.25481  0.30841  0.12280  11.00000  0.02497 
H9b   2     0.14167  0.38306  0.16251  11.00000  0.06191 
H10a  2     0.04973  0.75181  0.29244  11.00000  0.02517 
H10b  2     0.06836  0.69415  0.35453  11.00000  0.03359 
H10c  2    -0.01111  0.60574  0.30598  11.00000  0.02976 
H11   2     0.15236  0.54244  0.40455  11.00000  0.01421 
H13   2     0.41660  0.31922  0.42402  11.00000  0.02231 
H14   2     0.38253  0.09854  0.44899  11.00000  0.02896 
H16   2    -0.06498  0.00950  0.45106  11.00000  0.04111 
H17   2    -0.26769  0.13003  0.43423  11.00000  0.03688 
H19   2    -0.04164  0.45559  0.39860  11.00000  0.01485 
H21a  2    -0.39510  0.53293  0.39908  11.00000  0.03670 
H21b  2    -0.26581  0.51033  0.35549  11.00000  0.03986 
H21c  2    -0.23377  0.55739  0.42144  11.00000  0.04054 
H22a  2     0.12099 -0.06158  0.49039  11.00000  0.03819 
H22b  2     0.13291 -0.09471  0.42764  11.00000  0.03017 
H22c  2     0.27944 -0.07825  0.46431  11.00000  0.04979 
HKLF 4

END
;
