# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_jab-1-299
_database_code_depnum_ccdc_archive 'CCDC 2118052'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H23 F N2 O4'
_chemical_formula_sum            'C17 H23 F N2 O4'
_chemical_formula_weight         338.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H23FN2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.32624(13)
_cell_length_b                   15.5828(2)
_cell_length_c                   11.74267(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.1130(14)
_cell_angle_gamma                90
_cell_volume                     1815.30(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13960
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      72.1280
_cell_measurement_theta_min      3.9090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 -6 0.0513
0 -10 -1 0.0906
-7 0 2 0.0797
-3 2 7 0.0499
0 8 -4 0.0614
0 -9 3 0.0597
7 2 -2 0.0478
1 -6 6 0.0468
6 4 1 0.0571
0 -4 7 0.0337
2 2 6 0.0494

_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.101
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.8324 -0.7434 -6.0731 0.9448 -0.0678 0.0895
-0.0361 -9.9049 -1.1421 0.2423 -0.6950 -0.6648
-6.9778 0.0914 1.8232 0.4583 0.7227 -0.5950
-3.1347 1.8172 6.9604 -0.5772 0.6368 -0.4214
0.1512 8.0878 -3.8925 0.3919 0.4041 0.7736
-0.1319 -9.0476 2.8772 -0.2579 -0.5021 -0.7947
6.9901 1.8964 -1.7951 -0.4824 -0.5900 0.7380
0.7997 -6.1911 5.9489 -0.7603 -0.3023 -0.6607
5.9364 3.8046 1.2114 -0.7722 -0.2682 0.6593
-0.2030 -4.2147 6.9528 -0.8061 -0.0438 -0.6386
1.8385 1.7373 6.0872 -0.9569 0.1342 -0.0180

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24691
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.965
_diffrn_reflns_theta_min         3.918
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00  -7.00   1.00    1.00    --  -36.45 -19.00  60.00  101
  2  ω   -104.00 -20.00   1.00    1.00    --  -36.45 -57.00 -90.00   84
  3  ω   -106.00 -18.00   1.00    1.00    --  -36.45 -38.00  30.00   88
  4  ω   -106.00  33.00   1.00    1.00    --  -36.45   0.00 120.00  139
  5  ω     23.00  90.00   1.00    1.00    --   36.45-125.00  60.00   67
  6  ω    -33.00  55.00   1.00    1.00    --   36.45 -38.00-120.00   88
  7  ω     23.00  90.00   1.00    1.00    --   36.45-125.00-180.00   67
  8  ω     18.00 106.00   1.00    1.00    --   36.45  38.00  90.00   88
  9  ω     10.00 104.00   1.00    1.00    --   36.45  77.00  30.00   94
 10  ω     91.00 176.00   1.00    3.00    --  108.65  61.00  90.00   85
 11  ω     82.00 176.00   1.00    3.00    --  108.65  77.00   0.00   94
 12  ω     82.00 176.00   1.00    3.00    --  108.65  77.00  30.00   94
 13  ω     82.00 176.00   1.00    3.00    --  108.65  77.00  60.00   94
 14  ω     39.00 115.00   1.00    3.00    --  108.65-111.00 -30.00   76
 15  ω     41.00 135.00   1.00    3.00    --  108.65 -77.00 150.00   94
 16  ω     82.00 176.00   1.00    3.00    --  108.65  77.00  90.00   94
 17  ω     39.00 109.00   1.00    3.00    --  108.65 -94.00-150.00   70
 18  ω     87.00 178.00   1.00    3.00    --  108.65  30.00 150.00   91
 19  ω     39.00 109.00   1.00    3.00    --  108.65 -94.00  30.00   70
 20  ω     87.00 178.00   1.00    3.00    --  108.65  30.00  60.00   91
 21  ω     87.00 178.00   1.00    3.00    --  108.65  30.00 120.00   91
 22  ω     39.00 109.00   1.00    3.00    --  108.65 -94.00 120.00   70
 23  ω     91.00 176.00   1.00    3.00    --  108.65  61.00 120.00   85
 24  ω     91.00 176.00   1.00    3.00    --  108.65  61.00  60.00   85
 25  ω     42.00 127.00   1.00    3.00    --  108.65 -61.00 -60.00   85
 26  ω     70.00 178.00   1.00    3.00    --  108.65  15.00-180.00  108
 27  ω     91.00 176.00   1.00    3.00    --  108.65  61.00 -30.00   85
 28  ω     91.00 177.00   1.00    3.00    --  108.65  45.00  90.00   86
 29  ω     87.00 178.00   1.00    3.00    --  108.65  30.00  90.00   91
 30  ω     91.00 177.00   1.00    3.00    --  108.65  45.00  30.00   86
 31  ω     91.00 177.00   1.00    3.00    --  108.65  45.00  60.00   86
 32  ω     91.00 177.00   1.00    3.00    --  108.65  45.00 150.00   86
 33  ω     82.00 176.00   1.00    3.00    --  108.65  77.00 120.00   94
 34  ω    -33.00  49.00   1.00    1.00    --   36.45 -38.00 120.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0983944000
_diffrn_orient_matrix_UB_12      -0.0097210000
_diffrn_orient_matrix_UB_13      -0.1247005000
_diffrn_orient_matrix_UB_21      -0.0944651000
_diffrn_orient_matrix_UB_22      0.0668841000
_diffrn_orient_matrix_UB_23      0.0314861000
_diffrn_orient_matrix_UB_31      0.0742039000
_diffrn_orient_matrix_UB_32      0.0721435000
_diffrn_orient_matrix_UB_33      -0.0459553000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                6613
_reflns_number_total             6879
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.187
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         6879
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.027
_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)+(0.0289P)²+0.3462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0687
_refine_special_details          
'A disordered vinyl group was modeled over two positions without restraint.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H5AC)=Sof(H5AD)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7BA)=Sof(H7BB)=1-FVAR(1)
 Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C2(H2B), C2A(H2AA)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C5A(H5AC,H5AD)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), N2A(H2A), C6A(H6A),
 C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C6B(H6B), C00W(H00W)
3.d X=CH2 refined with riding coordinates:
 C7(H7A,H7B), C7A(H7AA,H7AB), C7B(H7BA,H7BB)
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15D,H15E,H15F), C16(H16D,H16E,H16F), C15A(H15A,H15B,
 H15C), C16A(H16A,H16B,H16C), C17A(H17A,H17B,H17C)
;
_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
F1 F 0.43013(12) 0.52428(8) 0.53511(10) 0.0267(3) Uani 1 1 d . . . . .
O1 O 0.26155(19) 0.54623(14) 0.33713(14) 0.0438(5) Uani 1 1 d . . . . .
O2 O 0.08974(16) 0.54317(12) 0.40832(13) 0.0349(4) Uani 1 1 d . . . . .
O3 O 0.13778(13) 0.44863(9) 0.78640(11) 0.0193(3) Uani 1 1 d . . . . .
O4 O 0.34138(13) 0.41329(9) 0.91318(12) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.21016(19) 0.54156(13) 0.41840(14) 0.0267(4) Uani 1 1 d . . . . .
N2 N 0.33149(15) 0.45242(11) 0.72927(13) 0.0175(3) Uani 1 1 d . . . . .
H2 H 0.417459 0.459121 0.753425 0.021 Uiso 1 1 calc R . . . .
C1 C 0.30384(19) 0.53614(14) 0.54753(16) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.26186(19) 0.45592(13) 0.60367(16) 0.0187(4) Uani 1 1 d . . . . .
H2B H 0.164789 0.459286 0.594776 0.022 Uiso 1 1 calc R . . . .
C3 C 0.25919(19) 0.43840(12) 0.80848(16) 0.0161(4) Uani 1 1 d . . . . .
C4 C 0.2895(2) 0.37417(15) 0.54094(18) 0.0249(4) Uani 1 1 d . . . . .
H4A H 0.249717 0.380352 0.456223 0.030 Uiso 1 1 calc R . . . .
H4B H 0.386061 0.367519 0.554825 0.030 Uiso 1 1 calc R . . . .
C5 C 0.2326(2) 0.29337(14) 0.58386(19) 0.0267(4) Uani 1 1 d . . . . .
H5A H 0.269832 0.243307 0.555238 0.032 Uiso 1 1 calc R . . . .
H5B H 0.262029 0.292032 0.669797 0.032 Uiso 1 1 calc R . . . .
C6 C 0.0816(2) 0.28777(15) 0.5439(2) 0.0308(5) Uani 1 1 d . . . . .
H6 H 0.039987 0.295614 0.463545 0.037 Uiso 1 1 calc R . . . .
C7 C 0.0033(3) 0.27278(18) 0.6124(2) 0.0402(6) Uani 1 1 d . . . . .
H7A H 0.040706 0.264550 0.693324 0.048 Uiso 1 1 calc R . . . .
H7B H -0.089671 0.270372 0.580110 0.048 Uiso 1 1 calc R . . . .
C8 C 0.29695(19) 0.62345(14) 0.60151(17) 0.0202(4) Uani 1 1 d . . . . .
C9 C 0.3703(2) 0.68980(15) 0.56980(18) 0.0258(4) Uani 1 1 d . . . . .
H9 H 0.423241 0.679172 0.518870 0.031 Uiso 1 1 calc R . . . .
C10 C 0.3646(2) 0.77125(15) 0.6139(2) 0.0300(5) Uani 1 1 d . . . . .
H10 H 0.413903 0.815369 0.592677 0.036 Uiso 1 1 calc R . . . .
C11 C 0.2126(2) 0.72152(14) 0.72178(18) 0.0253(4) Uani 1 1 d . . . . .
H11 H 0.159445 0.732323 0.772436 0.030 Uiso 1 1 calc R . . . .
C12 C 0.2186(2) 0.63933(13) 0.67856(17) 0.0211(4) Uani 1 1 d . . . . .
H12 H 0.170617 0.594962 0.700890 0.025 Uiso 1 1 calc R . . . .
C13 C 0.2852(2) 0.39577(14) 1.01388(16) 0.0212(4) Uani 1 1 d . . . . .
C14 C 0.4085(2) 0.36585(16) 1.11023(18) 0.0293(5) Uani 1 1 d . . . . .
H14A H 0.442780 0.314000 1.085214 0.044 Uiso 1 1 calc GR . . . .
H14B H 0.383803 0.355207 1.181951 0.044 Uiso 1 1 calc GR . . . .
H14C H 0.476798 0.409476 1.124247 0.044 Uiso 1 1 calc GR . . . .
C15 C 0.2308(3) 0.47818(18) 1.0502(2) 0.0399(6) Uani 1 1 d . . . . .
H15D H 0.300383 0.520968 1.067240 0.060 Uiso 1 1 calc GR . . . .
H15E H 0.201067 0.468163 1.119633 0.060 Uiso 1 1 calc GR . . . .
H15F H 0.156208 0.497802 0.986867 0.060 Uiso 1 1 calc GR . . . .
C16 C 0.1829(2) 0.32427(18) 0.9827(2) 0.0365(6) Uani 1 1 d . . . . .
H16D H 0.103967 0.344158 0.924192 0.055 Uiso 1 1 calc GR . . . .
H16E H 0.158733 0.306754 1.052530 0.055 Uiso 1 1 calc GR . . . .
H16F H 0.220793 0.276419 0.951687 0.055 Uiso 1 1 calc GR . . . .
F1A F 0.97240(11) 0.60937(8) 0.82176(10) 0.0227(2) Uani 1 1 d . . . . .
O1A O 0.88651(17) 0.75544(10) 0.74790(15) 0.0323(4) Uani 1 1 d . . . . .
O2A O 0.68933(16) 0.70752(11) 0.65060(15) 0.0315(4) Uani 1 1 d . . . . .
O3A O 0.61884(13) 0.42142(9) 0.73833(13) 0.0228(3) Uani 1 1 d . . . . .
O4A O 0.80116(14) 0.33564(10) 0.81711(13) 0.0251(3) Uani 1 1 d . . . . .
N1A N 0.80210(18) 0.69881(11) 0.71939(15) 0.0229(4) Uani 1 1 d . . . . .
N2A N 0.83123(16) 0.45784(11) 0.73394(14) 0.0190(3) Uani 1 1 d . . . . .
H2A H 0.913472 0.440632 0.750134 0.023 Uiso 1 1 calc R . . . .
C1A C 0.83558(19) 0.60935(13) 0.77558(17) 0.0186(4) Uani 1 1 d . . . . .
C2A C 0.79672(18) 0.54062(13) 0.67767(16) 0.0178(4) Uani 1 1 d . . . . .
H2AA H 0.699333 0.543002 0.640300 0.021 Uiso 1 1 calc R . . . .
C3A C 0.73891(19) 0.40656(13) 0.76197(17) 0.0185(4) Uani 1 1 d . . . . .
C4A C 0.8715(2) 0.55257(14) 0.58249(17) 0.0216(4) Uani 1 1 d . . . . .
H4AA H 0.965853 0.538322 0.615860 0.026 Uiso 1 1 calc R . . . .
H4AB H 0.866023 0.612279 0.558271 0.026 Uiso 1 1 calc R . . . .
C5A C 0.8119(2) 0.49582(15) 0.47331(19) 0.0257(4) Uani 1 1 d . . . . .
H5AA H 0.882304 0.480040 0.437192 0.031 Uiso 0.697(10) 1 calc R . P A 1
H5AB H 0.775853 0.443576 0.497584 0.031 Uiso 0.697(10) 1 calc R . P A 1
H5AC H 0.854281 0.510868 0.411977 0.031 Uiso 0.303(10) 1 calc R . P A 2
H5AD H 0.833836 0.436396 0.494832 0.031 Uiso 0.303(10) 1 calc R . P A 2
C6A C 0.7000(4) 0.5435(2) 0.3831(3) 0.0259(11) Uani 0.697(10) 1 d . . P A 1
H6A H 0.723293 0.593402 0.349992 0.031 Uiso 0.697(10) 1 calc R . P A 1
C7A C 0.5723(5) 0.5191(3) 0.3487(3) 0.0274(10) Uani 0.697(10) 1 d . . P A 1
H7AA H 0.545399 0.469517 0.379925 0.033 Uiso 0.697(10) 1 calc R . P A 1
H7AB H 0.509506 0.551429 0.293178 0.033 Uiso 0.697(10) 1 calc R . P A 1
C8A C 0.7668(2) 0.60077(12) 0.87378(17) 0.0194(4) Uani 1 1 d . . . . .
C9A C 0.8438(2) 0.58172(14) 0.98844(18) 0.0252(4) Uani 1 1 d . . . . .
H9A H 0.936846 0.575962 1.005101 0.030 Uiso 1 1 calc R . . . .
C10A C 0.7807(3) 0.57136(16) 1.0779(2) 0.0325(5) Uani 1 1 d . . . . .
H10A H 0.831763 0.558868 1.154685 0.039 Uiso 1 1 calc R . . . .
C11A C 0.6421(3) 0.57960(17) 1.0530(2) 0.0339(5) Uani 1 1 d . . . . .
H11A H 0.600222 0.572342 1.113031 0.041 Uiso 1 1 calc R . . . .
C12A C 0.5657(2) 0.59863(15) 0.9389(2) 0.0302(5) Uani 1 1 d . . . . .
H12A H 0.472740 0.604456 0.922573 0.036 Uiso 1 1 calc R . . . .
C13A C 0.6276(2) 0.60902(14) 0.84896(18) 0.0249(4) Uani 1 1 d . . . . .
H13A H 0.576180 0.621454 0.772284 0.030 Uiso 1 1 calc R . . . .
C14A C 0.7307(2) 0.27736(14) 0.87858(19) 0.0245(4) Uani 1 1 d . . . . .
C15A C 0.8393(2) 0.21223(15) 0.9331(2) 0.0351(5) Uani 1 1 d . . . . .
H15A H 0.866579 0.183281 0.871381 0.053 Uiso 1 1 calc GR . . . .
H15B H 0.804606 0.171116 0.977997 0.053 Uiso 1 1 calc GR . . . .
H15C H 0.915512 0.241079 0.984472 0.053 Uiso 1 1 calc GR . . . .
C16A C 0.6888(3) 0.32647(18) 0.9738(2) 0.0382(6) Uani 1 1 d . . . . .
H16A H 0.765781 0.355389 1.023981 0.057 Uiso 1 1 calc GR . . . .
H16B H 0.653023 0.287257 1.020414 0.057 Uiso 1 1 calc GR . . . .
H16C H 0.621169 0.367896 0.937490 0.057 Uiso 1 1 calc GR . . . .
C17A C 0.6121(3) 0.23420(17) 0.7910(3) 0.0407(6) Uani 1 1 d . . . . .
H17A H 0.543062 0.275936 0.759576 0.061 Uiso 1 1 calc GR . . . .
H17B H 0.576828 0.189842 0.830717 0.061 Uiso 1 1 calc GR . . . .
H17C H 0.641514 0.209547 0.727539 0.061 Uiso 1 1 calc GR . . . .
C6B C 0.6678(7) 0.5034(6) 0.4255(7) 0.026(3) Uani 0.303(10) 1 d . . P A 2
H6B H 0.612435 0.467242 0.454252 0.031 Uiso 0.303(10) 1 calc R . P A 2
C7B C 0.6121(13) 0.5590(10) 0.3434(9) 0.041(3) Uani 0.303(10) 1 d . . P A 2
H7BA H 0.665844 0.595717 0.313608 0.049 Uiso 0.303(10) 1 calc R . P A 2
H7BB H 0.518762 0.562003 0.314795 0.049 Uiso 0.303(10) 1 calc R . P A 2
C00W C 0.2855(2) 0.78801(16) 0.6900(2) 0.0294(5) Uani 1 1 d . . . . .
H00W H 0.281416 0.843098 0.719304 0.035 Uiso 1 1 calc R . . . .


_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 C1 1.364(2) . ?
O1 N1 1.216(2) . ?
O2 N1 1.216(2) . ?
O3 C3 1.218(2) . ?
O4 C3 1.344(2) . ?
O4 C13 1.480(2) . ?
N1 C1 1.558(2) . ?
N2 H2 0.8600 . ?
N2 C2 1.451(2) . ?
N2 C3 1.362(2) . ?
C1 C2 1.531(3) . ?
C1 C8 1.511(3) . ?
C2 H2B 0.9800 . ?
C2 C4 1.537(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.533(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.501(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.310(4) . ?
C7 H7A 0.9300 . ?
C7 H7B 0.9300 . ?
C8 C9 1.392(3) . ?
C8 C12 1.393(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9300 . ?
C10 C00W 1.392(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C11 C00W 1.391(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.523(3) . ?
C13 C15 1.510(3) . ?
C13 C16 1.509(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15D 0.9600 . ?
C15 H15E 0.9600 . ?
C15 H15F 0.9600 . ?
C16 H16D 0.9600 . ?
C16 H16E 0.9600 . ?
C16 H16F 0.9600 . ?
F1A C1A 1.366(2) . ?
O1A N1A 1.220(2) . ?
O2A N1A 1.227(2) . ?
O3A C3A 1.215(2) . ?
O4A C3A 1.350(2) . ?
O4A C14A 1.472(2) . ?
N1A C1A 1.540(3) . ?
N2A H2A 0.8600 . ?
N2A C2A 1.448(2) . ?
N2A C3A 1.353(3) . ?
C1A C2A 1.541(3) . ?
C1A C8A 1.518(3) . ?
C2A H2AA 0.9800 . ?
C2A C4A 1.536(2) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.538(3) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A H5AC 0.9700 . ?
C5A H5AD 0.9700 . ?
C5A C6A 1.526(4) . ?
C5A C6B 1.442(7) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.324(7) . ?
C7A H7AA 0.9300 . ?
C7A H7AB 0.9300 . ?
C8A C9A 1.392(3) . ?
C8A C13A 1.391(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.391(3) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.385(4) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.385(3) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.388(3) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.516(3) . ?
C14A C16A 1.514(3) . ?
C14A C17A 1.520(3) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C6B H6B 0.9300 . ?
C6B C7B 1.305(18) . ?
C7B H7BA 0.9300 . ?
C7B H7BB 0.9300 . ?
C00W H00W 0.9300 . ?

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
C3 O4 C13 119.78(14) . . ?
O1 N1 O2 125.41(18) . . ?
O1 N1 C1 118.60(17) . . ?
O2 N1 C1 115.96(15) . . ?
C2 N2 H2 120.4 . . ?
C3 N2 H2 120.4 . . ?
C3 N2 C2 119.28(15) . . ?
F1 C1 N1 104.89(14) . . ?
F1 C1 C2 109.19(16) . . ?
F1 C1 C8 108.94(16) . . ?
C2 C1 N1 106.84(15) . . ?
C8 C1 N1 105.70(16) . . ?
C8 C1 C2 120.18(15) . . ?
N2 C2 C1 110.40(16) . . ?
N2 C2 H2B 108.3 . . ?
N2 C2 C4 110.50(17) . . ?
C1 C2 H2B 108.3 . . ?
C1 C2 C4 110.97(15) . . ?
C4 C2 H2B 108.3 . . ?
O3 C3 O4 125.75(16) . . ?
O3 C3 N2 124.08(17) . . ?
O4 C3 N2 110.16(15) . . ?
C2 C4 H4A 109.1 . . ?
C2 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C2 112.58(16) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.88(19) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C5 C6 H6 117.2 . . ?
C7 C6 C5 125.7(2) . . ?
C7 C6 H6 117.2 . . ?
C6 C7 H7A 120.0 . . ?
C6 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
C9 C8 C1 117.65(18) . . ?
C9 C8 C12 119.9(2) . . ?
C12 C8 C1 122.40(18) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C00W 120.5(2) . . ?
C00W C10 H10 119.7 . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C00W 120.5(2) . . ?
C00W C11 H11 119.7 . . ?
C8 C12 H12 120.2 . . ?
C11 C12 C8 119.70(19) . . ?
C11 C12 H12 120.2 . . ?
O4 C13 C14 102.58(15) . . ?
O4 C13 C15 109.15(18) . . ?
O4 C13 C16 110.24(16) . . ?
C15 C13 C14 110.52(18) . . ?
C16 C13 C14 109.82(18) . . ?
C16 C13 C15 113.9(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15D 109.5 . . ?
C13 C15 H15E 109.5 . . ?
C13 C15 H15F 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C13 C16 H16D 109.5 . . ?
C13 C16 H16E 109.5 . . ?
C13 C16 H16F 109.5 . . ?
H16D C16 H16E 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C3A O4A C14A 120.38(15) . . ?
O1A N1A O2A 125.17(19) . . ?
O1A N1A C1A 118.61(17) . . ?
O2A N1A C1A 116.20(17) . . ?
C2A N2A H2A 118.8 . . ?
C3A N2A H2A 118.8 . . ?
C3A N2A C2A 122.44(16) . . ?
F1A C1A N1A 104.75(15) . . ?
F1A C1A C2A 108.84(15) . . ?
F1A C1A C8A 110.41(15) . . ?
C2A C1A N1A 109.18(15) . . ?
C8A C1A N1A 107.96(15) . . ?
C8A C1A C2A 115.19(15) . . ?
N2A C2A C1A 107.38(15) . . ?
N2A C2A H2AA 109.3 . . ?
N2A C2A C4A 109.30(15) . . ?
C1A C2A H2AA 109.3 . . ?
C4A C2A C1A 112.29(15) . . ?
C4A C2A H2AA 109.3 . . ?
O3A C3A O4A 125.82(18) . . ?
O3A C3A N2A 125.11(18) . . ?
O4A C3A N2A 109.05(16) . . ?
C2A C4A H4AA 109.3 . . ?
C2A C4A H4AB 109.3 . . ?
C2A C4A C5A 111.78(16) . . ?
H4AA C4A H4AB 107.9 . . ?
C5A C4A H4AA 109.3 . . ?
C5A C4A H4AB 109.3 . . ?
C4A C5A H5AA 109.6 . . ?
C4A C5A H5AB 109.6 . . ?
C4A C5A H5AC 108.7 . . ?
C4A C5A H5AD 108.7 . . ?
H5AA C5A H5AB 108.1 . . ?
H5AC C5A H5AD 107.6 . . ?
C6A C5A C4A 110.4(2) . . ?
C6A C5A H5AA 109.6 . . ?
C6A C5A H5AB 109.6 . . ?
C6B C5A C4A 114.1(3) . . ?
C6B C5A H5AC 108.7 . . ?
C6B C5A H5AD 108.7 . . ?
C5A C6A H6A 117.6 . . ?
C7A C6A C5A 124.7(4) . . ?
C7A C6A H6A 117.6 . . ?
C6A C7A H7AA 120.0 . . ?
C6A C7A H7AB 120.0 . . ?
H7AA C7A H7AB 120.0 . . ?
C9A C8A C1A 119.43(18) . . ?
C9A C8A C13A 120.11(18) . . ?
C13A C8A C1A 120.43(17) . . ?
C8A C9A H9A 120.2 . . ?
C10A C9A C8A 119.6(2) . . ?
C10A C9A H9A 120.2 . . ?
C9A C10A H10A 119.9 . . ?
C11A C10A C9A 120.2(2) . . ?
C11A C10A H10A 119.9 . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A C10A 120.1(2) . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A H12A 119.9 . . ?
C11A C12A C13A 120.2(2) . . ?
C13A C12A H12A 119.9 . . ?
C8A C13A H13A 120.1 . . ?
C12A C13A C8A 119.8(2) . . ?
C12A C13A H13A 120.1 . . ?
O4A C14A C15A 102.20(16) . . ?
O4A C14A C16A 109.37(18) . . ?
O4A C14A C17A 110.89(18) . . ?
C15A C14A C17A 110.6(2) . . ?
C16A C14A C15A 110.84(19) . . ?
C16A C14A C17A 112.5(2) . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C14A C16A H16A 109.5 . . ?
C14A C16A H16B 109.5 . . ?
C14A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C14A C17A H17A 109.5 . . ?
C14A C17A H17B 109.5 . . ?
C14A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C5A C6B H6B 118.8 . . ?
C7B C6B C5A 122.5(11) . . ?
C7B C6B H6B 118.8 . . ?
C6B C7B H7BA 120.0 . . ?
C6B C7B H7BB 120.0 . . ?
H7BA C7B H7BB 120.0 . . ?
C10 C00W H00W 120.3 . . ?
C11 C00W C10 119.3(2) . . ?
C11 C00W H00W 120.3 . . ?

_olex2_date_sample_data_collection 2019-08-05
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.866
####################################################################### 
# 
# 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_jab-bab-6214
_database_code_depnum_ccdc_archive 'CCDC 2118054'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2019-08-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H31 F N2 O4'
_chemical_formula_sum            'C20 H31 F N2 O4'
_chemical_formula_weight         382.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H31FN2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   11.84190(10)
_cell_length_b                   11.84190(10)
_cell_length_c                   27.22040(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3305.73(6)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    31810
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.1010
_cell_measurement_theta_min      4.2960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1236
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -2 -1 0.0323
-7 2 1 0.0323
1 -1 17 0.1952
-7 2 -4 0.0574
6 -1 -8 0.0914
2 -7 -1 0.0166
-1 7 -1 0.0341

_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.065
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.0000 -2.0000 -0.9995 -0.2535 0.5953 -0.6815
-7.0000 2.0000 0.9995 0.2535 -0.5953 0.6815
1.0000 -1.0000 16.9999 -0.4223 0.6157 0.6253
-7.0000 2.0000 -4.0005 0.3932 -0.7384 0.4813
6.0000 -1.0000 -7.9995 -0.1105 0.2658 -0.9062
2.0000 -7.0000 -1.0000 0.7823 0.5111 0.1004
-1.0000 7.0000 -0.9999 -0.8038 -0.4952 -0.2865

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            50607
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.268
_diffrn_reflns_theta_min         4.311
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -10.00   1.00    1.50    --  -36.45 -77.00  90.00   94
  2  ω   -104.00 -20.00   1.00    1.50    --  -36.45 -57.00-150.00   84
  3  ω    -53.00  31.00   1.00    1.50    --  -36.45  57.00-180.00   84
  4  ω   -104.00 -20.00   1.00    1.50    --  -36.45 -57.00 -90.00   84
  5  ω    -31.00  53.00   1.00    1.50    --   36.45 -57.00  60.00   84
  6  ω     18.00 106.00   1.00    1.50    --   36.45  38.00-180.00   88
  7  ω      7.00 108.00   1.00    1.50    --   36.45  19.00-180.00  101
  8  ω     39.00 130.00   1.00    5.00    --  108.65 -30.00 -60.00   91
  9  ω     91.00 176.00   1.00    5.00    --  108.65  61.00 120.00   85
 10  ω     70.00 178.00   1.00    5.00    --  108.65  15.00-180.00  108
 11  ω     91.00 176.00   1.00    5.00    --  108.65  61.00-150.00   85
 12  ω     40.00 126.00   1.00    5.00    --  108.65 -45.00  30.00   86
 13  ω     82.00 176.00   1.00    5.00    --  108.65  77.00  90.00   94
 14  ω     91.00 176.00   1.00    5.00    --  108.65  61.00-120.00   85
 15  ω     91.00 177.00   1.00    5.00    --  108.65  45.00 120.00   86
 16  ω     87.00 178.00   1.00    5.00    --  108.65  30.00 150.00   91
 17  ω     91.00 177.00   1.00    5.00    --  108.65  45.00 150.00   86
 18  ω     82.00 176.00   1.00    5.00    --  108.65  77.00 120.00   94
 19  ω     41.00 135.00   1.00    5.00    --  108.65 -77.00 -30.00   94
 20  ω     70.00 178.00   1.00    5.00    --  108.65  15.00 150.00  108
 21  ω   -104.00 -10.00   1.00    1.50    --  -36.45 -77.00 -30.00   94
 22  ω    -63.00  31.00   1.00    1.50    --  -36.45  77.00-150.00   94
 23  ω   -104.00 -20.00   1.00    1.50    --  -36.45 -57.00   0.00   84
 24  ω    -31.00  53.00   1.00    1.50    --   36.45 -57.00   0.00   84
 25  ω      4.00  34.00   1.00    1.50    --   36.45  87.00 158.59   30
 26  ω    -12.00  70.00   1.00    1.50    --   36.45 -89.00 -60.00   82
 27  ω     91.00 177.00   1.00    5.00    --  108.65  43.00  17.31   86
 28  ω     40.00 143.00   1.00    5.00    --  108.65 -90.00  75.06  103
 29  ω     40.00 142.00   1.00    5.00    --  108.65 -89.00-153.45  102
 30  ω     82.00 176.00   1.00    5.00    --  108.65  77.00 -90.00   94
 31  ω     91.00 177.00   1.00    5.00    --  108.65  45.00  60.00   86
 32  ω     87.00 178.00   1.00    5.00    --  108.65  30.00 -30.00   91
 33  ω     82.00 176.00   1.00    5.00    --  108.65  77.00 -30.00   94
 34  ω     82.00 146.00   1.00    5.00    --  108.65  77.00-180.00   64
 35  ω     41.00 135.00   1.00    5.00    --  108.65 -77.00 150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0773059000
_diffrn_orient_matrix_UB_12      -0.1298605000
_diffrn_orient_matrix_UB_13      -0.0279312000
_diffrn_orient_matrix_UB_21      0.0730726000
_diffrn_orient_matrix_UB_22      -0.0562185000
_diffrn_orient_matrix_UB_23      0.0286138000
_diffrn_orient_matrix_UB_31      -0.1060311000
_diffrn_orient_matrix_UB_32      -0.0503570000
_diffrn_orient_matrix_UB_33      0.0400551000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4305
_reflns_number_total             4353
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.140
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 2063 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4353
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0232
_refine_ls_restrained_S_all      1.052
_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)+(0.0329P)²+0.3875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0586
_refine_special_details          'Refined without restraint.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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
F1 F 1.10806(8) 0.80755(8) 0.56449(3) 0.02072(18) Uani 1 1 d . . . . .
O1 O 0.77643(10) 0.85127(10) 0.48902(4) 0.0192(2) Uani 1 1 d . . . . .
O2 O 0.76338(10) 0.90858(10) 0.56809(4) 0.0184(2) Uani 1 1 d . . . . .
O3 O 1.04203(12) 0.67556(12) 0.44870(4) 0.0280(3) Uani 1 1 d . . . . .
O4 O 1.16562(12) 0.67670(12) 0.50782(5) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.86626(12) 0.80039(12) 0.55308(4) 0.0152(2) Uani 1 1 d . . . . .
H1 H 0.887979 0.815172 0.583551 0.018 Uiso 1 1 calc R . . . .
N2 N 1.09028(12) 0.70676(12) 0.48978(5) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.79988(13) 0.85392(13) 0.53281(5) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.90218(13) 0.71869(13) 0.52513(5) 0.0143(3) Uani 1 1 d . . . . .
H2 H 0.862350 0.703529 0.492467 0.017 Uiso 1 1 calc R . . . .
C3 C 1.05163(14) 0.79286(14) 0.51940(5) 0.0158(3) Uani 1 1 d . . . . .
C4 C 1.10972(14) 0.92302(14) 0.49333(5) 0.0178(3) Uani 1 1 d . . . . .
H4A H 1.081856 0.977425 0.509935 0.021 Uiso 1 1 calc R . . . .
H4B H 1.076465 0.909023 0.459992 0.021 Uiso 1 1 calc R . . . .
C5 C 1.25912(14) 0.99493(15) 0.49174(6) 0.0235(3) Uani 1 1 d . . . . .
H5A H 1.292974 1.014663 0.524989 0.028 Uiso 1 1 calc R . . . .
H5B H 1.287542 0.938758 0.476983 0.028 Uiso 1 1 calc R . . . .
C6 C 1.31364(14) 1.11996(14) 0.46265(5) 0.0192(3) Uani 1 1 d . . . . .
C7 C 1.29002(16) 1.21949(16) 0.47679(6) 0.0261(3) Uani 1 1 d . . . . .
H7 H 1.241718 1.210006 0.504998 0.031 Uiso 1 1 calc R . . . .
C8 C 1.33800(16) 1.33227(16) 0.44912(7) 0.0298(4) Uani 1 1 d . . . . .
H8 H 1.321694 1.398071 0.458846 0.036 Uiso 1 1 calc R . . . .
C9 C 1.41019(17) 1.34782(16) 0.40701(6) 0.0289(4) Uani 1 1 d . . . . .
H9 H 1.441208 1.423278 0.388290 0.035 Uiso 1 1 calc R . . . .
C10 C 1.43584(17) 1.25102(16) 0.39299(6) 0.0275(3) Uani 1 1 d . . . . .
H10 H 1.485338 1.261533 0.365041 0.033 Uiso 1 1 calc R . . . .
C11 C 1.38757(16) 1.13776(15) 0.42072(6) 0.0230(3) Uani 1 1 d . . . . .
H11 H 1.405038 1.072716 0.411040 0.028 Uiso 1 1 calc R . . . .
C12 C 0.85281(13) 0.58620(13) 0.55088(5) 0.0163(3) Uani 1 1 d . . . . .
H12A H 0.854577 0.599844 0.586074 0.020 Uiso 1 1 calc R . . . .
H12B H 0.913414 0.555735 0.543830 0.020 Uiso 1 1 calc R . . . .
C13 C 0.71461(14) 0.47761(14) 0.53656(5) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.61419(16) 0.52245(17) 0.54139(7) 0.0308(4) Uani 1 1 d . . . . .
H14A H 0.617189 0.554310 0.574073 0.046 Uiso 1 1 calc GR . . . .
H14B H 0.528604 0.450316 0.534978 0.046 Uiso 1 1 calc GR . . . .
H14C H 0.633829 0.590823 0.518152 0.046 Uiso 1 1 calc GR . . . .
C15 C 0.67752(17) 0.36228(15) 0.57123(7) 0.0293(4) Uani 1 1 d . . . . .
H15A H 0.741129 0.334895 0.568706 0.044 Uiso 1 1 calc GR . . . .
H15B H 0.593312 0.291337 0.562297 0.044 Uiso 1 1 calc GR . . . .
H15C H 0.674892 0.388380 0.604407 0.044 Uiso 1 1 calc GR . . . .
C16 C 0.71413(17) 0.43266(16) 0.48378(6) 0.0269(3) Uani 1 1 d . . . . .
H16A H 0.628734 0.362286 0.475795 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.776303 0.403521 0.480825 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.737057 0.503990 0.461622 0.040 Uiso 1 1 calc GR . . . .
C17 C 0.67660(16) 0.96127(16) 0.55686(6) 0.0217(3) Uani 1 1 d . . . . .
C18 C 0.54669(17) 0.8523(2) 0.53854(7) 0.0347(4) Uani 1 1 d . . . . .
H18A H 0.558349 0.823013 0.507055 0.052 Uiso 1 1 calc GR . . . .
H18B H 0.486360 0.883726 0.535536 0.052 Uiso 1 1 calc GR . . . .
H18C H 0.513050 0.781090 0.561417 0.052 Uiso 1 1 calc GR . . . .
C19 C 0.7422(2) 1.07472(19) 0.52128(6) 0.0349(4) Uani 1 1 d . . . . .
H19A H 0.828055 1.135520 0.533000 0.052 Uiso 1 1 calc GR . . . .
H19B H 0.691683 1.117465 0.518809 0.052 Uiso 1 1 calc GR . . . .
H19C H 0.748406 1.042961 0.489526 0.052 Uiso 1 1 calc GR . . . .
C20 C 0.66194(17) 1.00896(17) 0.60717(6) 0.0260(3) Uani 1 1 d . . . . .
H20A H 0.621873 0.936513 0.629442 0.039 Uiso 1 1 calc GR . . . .
H20B H 0.608374 1.048339 0.604343 0.039 Uiso 1 1 calc GR . . . .
H20C H 0.746342 1.072062 0.619417 0.039 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
F1 C3 1.3662(16) . ?
O1 C1 1.2206(18) . ?
O2 C1 1.3446(17) . ?
O2 C17 1.4765(16) . ?
O3 N2 1.2258(19) . ?
O4 N2 1.2171(18) . ?
N1 H1 0.8600 . ?
N1 C1 1.3500(18) . ?
N1 C2 1.4517(17) . ?
N2 C3 1.5381(17) . ?
C2 H2 0.9800 . ?
C2 C3 1.5406(18) . ?
C2 C12 1.5420(18) . ?
C3 C4 1.5140(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.533(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.510(2) . ?
C6 C7 1.395(2) . ?
C6 C11 1.389(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(2) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5425(19) . ?
C13 C14 1.531(2) . ?
C13 C15 1.533(2) . ?
C13 C16 1.531(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.515(2) . ?
C17 C19 1.517(2) . ?
C17 C20 1.524(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C17 120.98(11) . . ?
C1 N1 H1 118.9 . . ?
C1 N1 C2 122.14(11) . . ?
C2 N1 H1 118.9 . . ?
O3 N2 C3 115.45(12) . . ?
O4 N2 O3 125.40(13) . . ?
O4 N2 C3 119.14(13) . . ?
O1 C1 O2 125.87(13) . . ?
O1 C1 N1 124.44(13) . . ?
O2 C1 N1 109.68(12) . . ?
N1 C2 H2 108.9 . . ?
N1 C2 C3 108.00(11) . . ?
N1 C2 C12 110.58(11) . . ?
C3 C2 H2 108.9 . . ?
C3 C2 C12 111.66(11) . . ?
C12 C2 H2 108.9 . . ?
F1 C3 N2 105.46(11) . . ?
F1 C3 C2 109.33(11) . . ?
F1 C3 C4 110.30(12) . . ?
N2 C3 C2 108.24(11) . . ?
C4 C3 N2 107.15(11) . . ?
C4 C3 C2 115.82(11) . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 112.92(12) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.62(12) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C7 C6 C5 121.05(14) . . ?
C11 C6 C5 120.51(14) . . ?
C11 C6 C7 118.43(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.41(16) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.44(16) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.75(15) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.81(15) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 H11 119.4 . . ?
C10 C11 C6 121.14(15) . . ?
C10 C11 H11 119.4 . . ?
C2 C12 H12A 108.3 . . ?
C2 C12 H12B 108.3 . . ?
C2 C12 C13 115.96(11) . . ?
H12A C12 H12B 107.4 . . ?
C13 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
C14 C13 C12 111.93(12) . . ?
C14 C13 C15 109.27(13) . . ?
C15 C13 C12 107.41(12) . . ?
C16 C13 C12 110.17(12) . . ?
C16 C13 C14 109.42(14) . . ?
C16 C13 C15 108.56(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 C18 109.45(13) . . ?
O2 C17 C19 110.48(13) . . ?
O2 C17 C20 101.70(11) . . ?
C18 C17 C19 113.36(15) . . ?
C18 C17 C20 110.86(14) . . ?
C19 C17 C20 110.38(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_date_sample_data_collection 2019-08-15
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.174
_oxdiff_exptl_absorpt_empirical_full_min 0.842
####################################################################### 
# 
# 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_jab-4-262-d1
_database_code_depnum_ccdc_archive 'CCDC 2118055'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2019-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H31 F N2 O4'
_chemical_formula_sum            'C20 H31 F N2 O4'
_chemical_formula_weight         382.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H31FN2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.50004(6)
_cell_length_b                   18.45454(10)
_cell_length_c                   30.36728(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6444.79(6)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    24703
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.1420
_cell_measurement_theta_min      2.7800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -7 -3 0.1185
-5 10 0 0.1161
-2 -1 -19 0.1650
2 1 19 0.1650
7 5 3 0.1072
7 -5 0 0.1129
6 -5 -8 0.1499
7 1 -5 0.1475
6 7 1 0.1253

_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.246
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.9950 -6.9988 -2.9982 -0.9411 0.1133 0.3322
-4.9991 9.9891 -0.0071 0.3224 0.4718 0.9037
-1.9978 -1.0057 -18.9916 -0.4006 0.8974 -0.2048
1.9978 1.0057 18.9916 0.4006 -0.8974 0.2048
6.9948 5.0010 2.9996 0.8767 -0.2077 -0.5130
6.9969 -4.9919 0.0057 0.1636 -0.3815 -0.9376
5.9979 -4.9947 -7.9910 0.0123 0.0146 -0.9915
6.9960 1.0019 -4.9948 0.5242 0.0319 -0.8204
5.9951 6.9982 0.9991 0.9214 -0.0224 -0.3727

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35099
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.268
_diffrn_reflns_theta_min         2.802
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.00    --  -36.45  57.00 -90.00   84
  2  ω   -106.00 -18.00   1.00    1.00    --  -36.45 -38.00  30.00   88
  3  ω      1.00  75.00   1.00    1.00    --   36.45 -99.00-150.00   74
  4  ω     20.00 104.00   1.00    1.00    --   36.45  57.00  90.00   84
  5  ω     23.00  90.00   1.00    1.00    --   36.45-125.00  90.00   67
  6  ω     39.00 109.00   1.00    1.00    --  108.65 -94.00  90.00   70
  7  ω     91.00 176.00   1.00    1.00    --  108.65  61.00  60.00   85
  8  ω    100.00 178.00   1.00    1.00    --  108.65 111.00 -60.00   78
  9  ω     39.00 109.00   1.00    1.00    --  108.65 -94.00 -90.00   70
 10  ω     82.00 176.00   1.00    1.00    --  108.65  77.00-180.00   94
 11  ω     91.00 176.00   1.00    1.00    --  108.65  61.00  30.00   85
 12  ω     39.00 109.00   1.00    1.00    --  108.65 -94.00  30.00   70
 13  ω     40.00 126.00   1.00    1.00    --  108.65 -45.00  30.00   86
 14  ω   -104.00 -20.00   1.00    1.00    --  -36.45 -57.00-180.00   84
 15  ω   -104.00 -60.00   1.00    1.00    --  -36.45 -77.00 -60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0721841000
_diffrn_orient_matrix_UB_12      0.0684075000
_diffrn_orient_matrix_UB_13      0.0098779000
_diffrn_orient_matrix_UB_21      -0.0323566000
_diffrn_orient_matrix_UB_22      0.0310101000
_diffrn_orient_matrix_UB_23      -0.0454931000
_diffrn_orient_matrix_UB_31      -0.1080427000
_diffrn_orient_matrix_UB_32      0.0364157000
_diffrn_orient_matrix_UB_33      0.0202218000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                12176
_reflns_number_total             12498
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.165
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 5234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     748
_refine_ls_number_reflns         12498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.046
_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)+(0.0423P)²+0.9956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0771
_refine_special_details          'refined without restraint'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C2B(H2B), C2C(H2C)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C11(H11A,H11B), C4B(H4BA,H4BB), C5B(H5BA,H5BB),
 C11B(H11C,H11D), C4C(H4CA,H4CB), C5C(H5CA,H5CB), C11C(H11E,H11F)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C9(H9), C10(H10), C15(H15), C01L(H01L), C7(H7), N1B(H1B),
 C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B), C1A(H1A), N1C(H1C), C7C(H7C),
 C8C(H8C), C9C(H9C), C10C(H10C)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C1D(H1DA,H1DB,H1DC), C13B(H13D,H13E,H13F),
 C14B(H14D,H14E,H14F), C15B(H15A,H15B,H15C), C17B(H17D,H17E,H17F), C18B(H18D,
 H18E,H18F), C19B(H19D,H19E,H19F), C13C(H13G,H13H,H13I), C14C(H14G,H14H,H14I),
 C15C(H15D,H15E,H15F), C17C(H17G,H17H,H17I), C18C(H18G,H18H,H18I), C19C(H19G,
 H19H,H19I)
;
_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
F1 F 0.46586(10) 0.60539(6) 0.40583(4) 0.0231(2) Uani 1 1 d . . . . .
O1 O 0.75996(11) 0.44681(7) 0.41738(4) 0.0197(3) Uani 1 1 d . . . . .
O2 O 0.86475(11) 0.44505(7) 0.35342(4) 0.0190(3) Uani 1 1 d . . . . .
O3 O 0.64970(15) 0.65029(9) 0.32180(5) 0.0365(4) Uani 1 1 d . . . . .
O4 O 0.46995(14) 0.67506(9) 0.33598(5) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.69606(13) 0.50086(8) 0.35441(5) 0.0151(3) Uani 1 1 d . . . . .
H1 H 0.715293 0.515445 0.328521 0.018 Uiso 1 1 calc R . . . .
N2 N 0.56198(15) 0.64579(8) 0.34416(5) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.77364(15) 0.46227(9) 0.37879(6) 0.0158(3) Uani 1 1 d . . . . .
C2 C 0.58213(15) 0.51767(9) 0.37135(6) 0.0142(3) Uani 1 1 d . . . . .
H2 H 0.571181 0.488411 0.397957 0.017 Uiso 1 1 calc R . . . .
C3 C 0.57153(16) 0.59792(10) 0.38526(6) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.66548(18) 0.62730(10) 0.41490(7) 0.0236(4) Uani 1 1 d . . . . .
H4A H 0.740611 0.619193 0.401243 0.028 Uiso 1 1 calc R . . . .
H4B H 0.664238 0.601111 0.442588 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6505(2) 0.70898(11) 0.42412(7) 0.0291(5) Uani 1 1 d . . . . .
H5A H 0.688278 0.736130 0.400811 0.035 Uiso 1 1 calc R . . . .
H5B H 0.568274 0.720691 0.423323 0.035 Uiso 1 1 calc R . . . .
C6 C 0.69980(18) 0.73297(10) 0.46790(6) 0.0232(4) Uani 1 1 d . . . . .
C8 C 0.6508(2) 0.70670(12) 0.50662(7) 0.0313(5) Uani 1 1 d . . . . .
H8 H 0.592380 0.671918 0.505133 0.038 Uiso 1 1 calc R . . . .
C9 C 0.77433(19) 0.78314(12) 0.55001(7) 0.0307(5) Uani 1 1 d . . . . .
H9 H 0.798674 0.800055 0.577348 0.037 Uiso 1 1 calc R . . . .
C10 C 0.82433(18) 0.80925(11) 0.51226(8) 0.0296(5) Uani 1 1 d . . . . .
H10 H 0.882682 0.844024 0.513992 0.035 Uiso 1 1 calc R . . . .
C11 C 0.48661(15) 0.49559(9) 0.33886(6) 0.0161(3) Uani 1 1 d . . . . .
H11A H 0.515666 0.502657 0.309186 0.019 Uiso 1 1 calc R . . . .
H11B H 0.420929 0.527926 0.342797 0.019 Uiso 1 1 calc R . . . .
C12 C 0.44296(16) 0.41694(9) 0.34305(6) 0.0177(4) Uani 1 1 d . . . . .
C13 C 0.36455(17) 0.40216(11) 0.30319(6) 0.0223(4) Uani 1 1 d . . . . .
H13A H 0.301055 0.435928 0.303119 0.033 Uiso 1 1 calc GR . . . .
H13B H 0.334697 0.353659 0.304899 0.033 Uiso 1 1 calc GR . . . .
H13C H 0.408832 0.407631 0.276596 0.033 Uiso 1 1 calc GR . . . .
C14 C 0.54334(17) 0.36207(10) 0.34308(7) 0.0242(4) Uani 1 1 d . . . . .
H14A H 0.590701 0.369381 0.317435 0.036 Uiso 1 1 calc GR . . . .
H14B H 0.512352 0.313765 0.342779 0.036 Uiso 1 1 calc GR . . . .
H14C H 0.589705 0.368748 0.369055 0.036 Uiso 1 1 calc GR . . . .
C15 C 0.6875(2) 0.73150(14) 0.54727(7) 0.0353(5) Uani 1 1 d . . . . .
H15 H 0.653733 0.713404 0.572831 0.042 Uiso 1 1 calc R . . . .
C16 C 0.95918(15) 0.39789(10) 0.37032(6) 0.0176(4) Uani 1 1 d . . . . .
C17 C 1.04368(16) 0.39772(11) 0.33207(6) 0.0234(4) Uani 1 1 d . . . . .
H17A H 1.006231 0.377934 0.306497 0.035 Uiso 1 1 calc GR . . . .
H17B H 1.110147 0.368676 0.339432 0.035 Uiso 1 1 calc GR . . . .
H17C H 1.068214 0.446433 0.326019 0.035 Uiso 1 1 calc GR . . . .
C18 C 0.91112(17) 0.32243(10) 0.37822(7) 0.0225(4) Uani 1 1 d . . . . .
H18A H 0.856502 0.323824 0.402115 0.034 Uiso 1 1 calc GR . . . .
H18B H 0.973679 0.290127 0.385486 0.034 Uiso 1 1 calc GR . . . .
H18C H 0.872778 0.305601 0.352072 0.034 Uiso 1 1 calc GR . . . .
C19 C 1.01503(16) 0.43158(10) 0.41085(6) 0.0214(4) Uani 1 1 d . . . . .
H19A H 1.032498 0.481554 0.405083 0.032 Uiso 1 1 calc GR . . . .
H19B H 1.085505 0.406124 0.417764 0.032 Uiso 1 1 calc GR . . . .
H19C H 0.962329 0.428322 0.435289 0.032 Uiso 1 1 calc GR . . . .
C1D C 0.37171(19) 0.40791(12) 0.38517(7) 0.0296(5) Uani 1 1 d . . . . .
H1DA H 0.420430 0.416701 0.410274 0.044 Uiso 1 1 calc GR . . . .
H1DB H 0.341443 0.359490 0.386579 0.044 Uiso 1 1 calc GR . . . .
H1DC H 0.308481 0.441881 0.385104 0.044 Uiso 1 1 calc GR . . . .
C01L C 0.78797(18) 0.78382(11) 0.47116(7) 0.0260(4) Uani 1 1 d . . . . .
H01L H 0.823336 0.801228 0.445728 0.031 Uiso 1 1 calc R . . . .
C7 C 0.29098(18) 0.60935(11) 0.64221(7) 0.0243(4) Uani 1 1 d . . . . .
H7 H 0.249838 0.626497 0.617993 0.029 Uiso 1 1 calc R . . . .
F1B F 0.43684(9) 0.37216(6) 0.56199(3) 0.0200(2) Uani 1 1 d . . . . .
O1B O 0.79451(11) 0.46605(7) 0.58244(4) 0.0204(3) Uani 1 1 d . . . . .
O2B O 0.84866(11) 0.52872(7) 0.52064(4) 0.0205(3) Uani 1 1 d . . . . .
O3B O 0.46796(12) 0.50762(8) 0.48561(5) 0.0268(3) Uani 1 1 d . . . . .
O4B O 0.33503(12) 0.42652(9) 0.49714(5) 0.0294(3) Uani 1 1 d . . . . .
N1B N 0.69579(13) 0.45823(8) 0.51745(5) 0.0160(3) Uani 1 1 d . . . . .
H1B H 0.687932 0.477038 0.491709 0.019 Uiso 1 1 calc R . . . .
N2B N 0.42623(13) 0.45650(8) 0.50596(5) 0.0180(3) Uani 1 1 d . . . . .
C1B C 0.78190(15) 0.48269(9) 0.54393(6) 0.0161(3) Uani 1 1 d . . . . .
C2B C 0.61632(15) 0.40141(9) 0.53093(6) 0.0147(3) Uani 1 1 d . . . . .
H2B H 0.651362 0.377209 0.556410 0.018 Uiso 1 1 calc R . . . .
C3B C 0.49702(15) 0.43046(9) 0.54581(6) 0.0155(3) Uani 1 1 d . . . . .
C4B C 0.49748(16) 0.49027(10) 0.58002(6) 0.0180(4) Uani 1 1 d . . . . .
H4BA H 0.536981 0.532406 0.568158 0.022 Uiso 1 1 calc R . . . .
H4BB H 0.540180 0.474134 0.605767 0.022 Uiso 1 1 calc R . . . .
C5B C 0.37347(16) 0.51149(11) 0.59368(6) 0.0209(4) Uani 1 1 d . . . . .
H5BA H 0.340602 0.542287 0.570985 0.025 Uiso 1 1 calc R . . . .
H5BB H 0.326429 0.467933 0.595199 0.025 Uiso 1 1 calc R . . . .
C6B C 0.36539(16) 0.55057(10) 0.63733(6) 0.0193(4) Uani 1 1 d . . . . .
C7B C 0.42487(19) 0.52557(11) 0.67429(7) 0.0263(4) Uani 1 1 d . . . . .
H7B H 0.474228 0.485874 0.671713 0.032 Uiso 1 1 calc R . . . .
C8B C 0.41154(19) 0.55901(12) 0.71485(7) 0.0293(4) Uani 1 1 d . . . . .
H8B H 0.452241 0.541910 0.739184 0.035 Uiso 1 1 calc R . . . .
C9B C 0.33753(19) 0.61796(11) 0.71918(7) 0.0266(4) Uani 1 1 d . . . . .
H9B H 0.328668 0.640507 0.746363 0.032 Uiso 1 1 calc R . . . .
C10B C 0.27730(19) 0.64293(11) 0.68307(7) 0.0293(5) Uani 1 1 d . . . . .
H10B H 0.227345 0.682290 0.685908 0.035 Uiso 1 1 calc R . . . .
C11B C 0.60327(15) 0.34413(9) 0.49464(6) 0.0162(3) Uani 1 1 d . . . . .
H11C H 0.616072 0.367349 0.466394 0.019 Uiso 1 1 calc R . . . .
H11D H 0.523817 0.326494 0.494962 0.019 Uiso 1 1 calc R . . . .
C12B C 0.68578(15) 0.27862(10) 0.49825(6) 0.0176(4) Uani 1 1 d . . . . .
C13B C 0.67125(18) 0.23393(11) 0.45604(6) 0.0243(4) Uani 1 1 d . . . . .
H13D H 0.591755 0.218693 0.453315 0.037 Uiso 1 1 calc GR . . . .
H13E H 0.720796 0.192120 0.457335 0.037 Uiso 1 1 calc GR . . . .
H13F H 0.692092 0.262999 0.431039 0.037 Uiso 1 1 calc GR . . . .
C14B C 0.81249(16) 0.30282(11) 0.50302(7) 0.0236(4) Uani 1 1 d . . . . .
H14D H 0.831450 0.336105 0.479812 0.035 Uiso 1 1 calc GR . . . .
H14E H 0.862602 0.261319 0.501266 0.035 Uiso 1 1 calc GR . . . .
H14F H 0.822866 0.326219 0.530982 0.035 Uiso 1 1 calc GR . . . .
C15B C 0.65219(18) 0.23119(11) 0.53750(6) 0.0244(4) Uani 1 1 d . . . . .
H15A H 0.657771 0.259033 0.564121 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.703883 0.190438 0.539174 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.573812 0.214311 0.533864 0.037 Uiso 1 1 calc GR . . . .
C16B C 0.96083(16) 0.55552(10) 0.53772(6) 0.0210(4) Uani 1 1 d . . . . .
C17B C 1.00285(19) 0.60262(12) 0.49998(7) 0.0322(5) Uani 1 1 d . . . . .
H17D H 1.009433 0.573782 0.473784 0.048 Uiso 1 1 calc GR . . . .
H17E H 1.077434 0.622733 0.507204 0.048 Uiso 1 1 calc GR . . . .
H17F H 0.948272 0.641142 0.495065 0.048 Uiso 1 1 calc GR . . . .
C18B C 1.04114(18) 0.49146(12) 0.54517(8) 0.0316(5) Uani 1 1 d . . . . .
H18D H 1.010243 0.461410 0.568164 0.047 Uiso 1 1 calc GR . . . .
H18E H 1.116747 0.508663 0.553547 0.047 Uiso 1 1 calc GR . . . .
H18F H 1.047238 0.463788 0.518498 0.047 Uiso 1 1 calc GR . . . .
C19B C 0.94245(19) 0.60073(12) 0.57876(7) 0.0305(5) Uani 1 1 d . . . . .
H19D H 0.885131 0.637339 0.572998 0.046 Uiso 1 1 calc GR . . . .
H19E H 1.014420 0.623361 0.586985 0.046 Uiso 1 1 calc GR . . . .
H19F H 0.916170 0.570157 0.602324 0.046 Uiso 1 1 calc GR . . . .
C1A C 0.39150(18) 0.37869(11) 0.78195(9) 0.0339(5) Uani 1 1 d . . . . .
H1A H 0.371742 0.386858 0.752672 0.041 Uiso 1 1 calc R . . . .
F1C F 0.79803(9) 0.27972(5) 0.72603(3) 0.0190(2) Uani 1 1 d . . . . .
O1C O 0.81476(11) 0.52153(7) 0.74980(4) 0.0187(3) Uani 1 1 d . . . . .
O2C O 0.75122(12) 0.57874(7) 0.68747(4) 0.0198(3) Uani 1 1 d . . . . .
O3C O 0.62122(13) 0.35940(8) 0.64953(5) 0.0275(3) Uani 1 1 d . . . . .
O4C O 0.71658(14) 0.25833(8) 0.65072(5) 0.0315(3) Uani 1 1 d . . . . .
N1C N 0.79899(13) 0.46374(8) 0.68370(5) 0.0155(3) Uani 1 1 d . . . . .
H1C H 0.776420 0.467497 0.656801 0.019 Uiso 1 1 calc R . . . .
N2C N 0.68945(14) 0.31664(8) 0.66629(5) 0.0189(3) Uani 1 1 d . . . . .
C1C C 0.79042(15) 0.52188(9) 0.71066(6) 0.0154(3) Uani 1 1 d . . . . .
C2C C 0.84514(15) 0.39560(9) 0.69907(6) 0.0146(3) Uani 1 1 d . . . . .
H2C H 0.884071 0.405769 0.727101 0.018 Uiso 1 1 calc R . . . .
C3C C 0.74732(16) 0.34106(9) 0.70936(6) 0.0156(3) Uani 1 1 d . . . . .
C4C C 0.65604(16) 0.36895(9) 0.74102(6) 0.0165(3) Uani 1 1 d . . . . .
H4CA H 0.615447 0.409157 0.727344 0.020 Uiso 1 1 calc R . . . .
H4CB H 0.694513 0.387259 0.767172 0.020 Uiso 1 1 calc R . . . .
C5C C 0.56666(17) 0.31166(10) 0.75483(7) 0.0242(4) Uani 1 1 d . . . . .
H5CA H 0.518370 0.299082 0.729779 0.029 Uiso 1 1 calc R . . . .
H5CB H 0.606719 0.268199 0.764456 0.029 Uiso 1 1 calc R . . . .
C6C C 0.49136(17) 0.33969(10) 0.79156(7) 0.0221(4) Uani 1 1 d . . . . .
C7C C 0.5218(2) 0.32870(14) 0.83531(7) 0.0352(5) Uani 1 1 d . . . . .
H7C H 0.588587 0.302843 0.842484 0.042 Uiso 1 1 calc R . . . .
C8C C 0.4503(3) 0.35721(17) 0.86856(8) 0.0560(9) Uani 1 1 d . . . . .
H8C H 0.470251 0.350662 0.897974 0.067 Uiso 1 1 calc R . . . .
C9C C 0.3504(3) 0.39497(14) 0.85780(11) 0.0574(9) Uani 1 1 d . . . . .
H9C H 0.302870 0.413245 0.879956 0.069 Uiso 1 1 calc R . . . .
C10C C 0.3213(2) 0.40547(13) 0.81450(11) 0.0507(8) Uani 1 1 d . . . . .
H10C H 0.253962 0.430727 0.807248 0.061 Uiso 1 1 calc R . . . .
C11C C 0.93900(16) 0.36563(9) 0.66795(6) 0.0173(4) Uani 1 1 d . . . . .
H11E H 0.924332 0.383735 0.638479 0.021 Uiso 1 1 calc R . . . .
H11F H 0.932367 0.313252 0.667024 0.021 Uiso 1 1 calc R . . . .
C12C C 1.06443(16) 0.38577(10) 0.68125(6) 0.0194(4) Uani 1 1 d . . . . .
C13C C 1.14675(18) 0.35838(12) 0.64524(7) 0.0271(4) Uani 1 1 d . . . . .
H13G H 1.135692 0.307241 0.641222 0.041 Uiso 1 1 calc GR . . . .
H13H H 1.225749 0.367560 0.653800 0.041 Uiso 1 1 calc GR . . . .
H13I H 1.130386 0.383160 0.618149 0.041 Uiso 1 1 calc GR . . . .
C14C C 1.07979(18) 0.46765(11) 0.68642(8) 0.0295(5) Uani 1 1 d . . . . .
H14G H 1.056786 0.491442 0.659695 0.044 Uiso 1 1 calc GR . . . .
H14H H 1.159900 0.478318 0.692506 0.044 Uiso 1 1 calc GR . . . .
H14I H 1.032339 0.484572 0.710310 0.044 Uiso 1 1 calc GR . . . .
C15C C 1.09574(19) 0.34725(15) 0.72408(7) 0.0350(5) Uani 1 1 d . . . . .
H15D H 1.045282 0.363705 0.747193 0.053 Uiso 1 1 calc GR . . . .
H15E H 1.174954 0.357895 0.731666 0.053 Uiso 1 1 calc GR . . . .
H15F H 1.086683 0.295908 0.720329 0.053 Uiso 1 1 calc GR . . . .
C16C C 0.76927(18) 0.65346(9) 0.70388(6) 0.0208(4) Uani 1 1 d . . . . .
C17C C 0.7258(2) 0.69869(11) 0.66543(7) 0.0316(5) Uani 1 1 d . . . . .
H17G H 0.771228 0.688075 0.639715 0.047 Uiso 1 1 calc GR . . . .
H17H H 0.732907 0.749202 0.672494 0.047 Uiso 1 1 calc GR . . . .
H17I H 0.645647 0.687375 0.659794 0.047 Uiso 1 1 calc GR . . . .
C18C C 0.89815(18) 0.66525(10) 0.71114(7) 0.0254(4) Uani 1 1 d . . . . .
H18G H 0.923553 0.636889 0.735837 0.038 Uiso 1 1 calc GR . . . .
H18H H 0.912457 0.715614 0.716902 0.038 Uiso 1 1 calc GR . . . .
H18I H 0.940165 0.650711 0.685291 0.038 Uiso 1 1 calc GR . . . .
C19C C 0.69606(18) 0.66731(11) 0.74473(6) 0.0255(4) Uani 1 1 d . . . . .
H19G H 0.615831 0.657705 0.738236 0.038 Uiso 1 1 calc GR . . . .
H19H H 0.704674 0.716930 0.753652 0.038 Uiso 1 1 calc GR . . . .
H19I H 0.721466 0.636049 0.768095 0.038 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
F1 C3 1.373(2) . ?
O1 C1 1.216(2) . ?
O2 C1 1.339(2) . ?
O2 C16 1.483(2) . ?
O3 N2 1.219(2) . ?
O4 N2 1.214(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.361(2) . ?
N1 C2 1.441(2) . ?
N2 C3 1.533(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.545(2) . ?
C2 C11 1.531(2) . ?
C3 C4 1.507(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.543(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.512(3) . ?
C6 C8 1.391(3) . ?
C6 C01L 1.385(3) . ?
C8 H8 0.9300 . ?
C8 C15 1.383(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C9 C15 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C01L 1.397(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.541(2) . ?
C12 C13 1.534(2) . ?
C12 C14 1.536(3) . ?
C12 C1D 1.528(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C16 C17 1.514(2) . ?
C16 C18 1.517(3) . ?
C16 C19 1.521(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C1D H1DA 0.9600 . ?
C1D H1DB 0.9600 . ?
C1D H1DC 0.9600 . ?
C01L H01L 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6B 1.390(3) . ?
C7 C10B 1.396(3) . ?
F1B C3B 1.370(2) . ?
O1B C1B 1.218(2) . ?
O2B C1B 1.346(2) . ?
O2B C16B 1.476(2) . ?
O3B N2B 1.225(2) . ?
O4B N2B 1.216(2) . ?
N1B H1B 0.8600 . ?
N1B C1B 1.353(2) . ?
N1B C2B 1.450(2) . ?
N2B C3B 1.536(2) . ?
C2B H2B 0.9800 . ?
C2B C3B 1.541(2) . ?
C2B C11B 1.534(2) . ?
C3B C4B 1.516(2) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B C5B 1.536(2) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C5B C6B 1.512(2) . ?
C6B C7B 1.393(3) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.386(3) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.388(3) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.376(3) . ?
C10B H10B 0.9300 . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C11B C12B 1.541(2) . ?
C12B C13B 1.533(3) . ?
C12B C14B 1.531(2) . ?
C12B C15B 1.528(2) . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C15B H15A 0.9600 . ?
C15B H15B 0.9600 . ?
C15B H15C 0.9600 . ?
C16B C17B 1.518(3) . ?
C16B C18B 1.517(3) . ?
C16B C19B 1.515(3) . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C1A H1A 0.9300 . ?
C1A C6C 1.386(3) . ?
C1A C10C 1.369(3) . ?
F1C C3C 1.3703(19) . ?
O1C C1C 1.221(2) . ?
O2C C1C 1.342(2) . ?
O2C C16C 1.481(2) . ?
O3C N2C 1.224(2) . ?
O4C N2C 1.216(2) . ?
N1C H1C 0.8600 . ?
N1C C1C 1.353(2) . ?
N1C C2C 1.442(2) . ?
N2C C3C 1.535(2) . ?
C2C H2C 0.9800 . ?
C2C C3C 1.541(2) . ?
C2C C11C 1.538(2) . ?
C3C C4C 1.514(2) . ?
C4C H4CA 0.9700 . ?
C4C H4CB 0.9700 . ?
C4C C5C 1.533(2) . ?
C5C H5CA 0.9700 . ?
C5C H5CB 0.9700 . ?
C5C C6C 1.504(3) . ?
C6C C7C 1.389(3) . ?
C7C H7C 0.9300 . ?
C7C C8C 1.405(4) . ?
C8C H8C 0.9300 . ?
C8C C9C 1.383(5) . ?
C9C H9C 0.9300 . ?
C9C C10C 1.370(5) . ?
C10C H10C 0.9300 . ?
C11C H11E 0.9700 . ?
C11C H11F 0.9700 . ?
C11C C12C 1.543(3) . ?
C12C C13C 1.532(3) . ?
C12C C14C 1.529(3) . ?
C12C C15C 1.525(3) . ?
C13C H13G 0.9600 . ?
C13C H13H 0.9600 . ?
C13C H13I 0.9600 . ?
C14C H14G 0.9600 . ?
C14C H14H 0.9600 . ?
C14C H14I 0.9600 . ?
C15C H15D 0.9600 . ?
C15C H15E 0.9600 . ?
C15C H15F 0.9600 . ?
C16C C17C 1.520(3) . ?
C16C C18C 1.514(3) . ?
C16C C19C 1.521(3) . ?
C17C H17G 0.9600 . ?
C17C H17H 0.9600 . ?
C17C H17I 0.9600 . ?
C18C H18G 0.9600 . ?
C18C H18H 0.9600 . ?
C18C H18I 0.9600 . ?
C19C H19G 0.9600 . ?
C19C H19H 0.9600 . ?
C19C H19I 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C16 120.87(13) . . ?
C1 N1 H1 119.5 . . ?
C1 N1 C2 120.98(14) . . ?
C2 N1 H1 119.5 . . ?
O3 N2 C3 115.69(15) . . ?
O4 N2 O3 125.26(17) . . ?
O4 N2 C3 119.04(16) . . ?
O1 C1 O2 126.87(16) . . ?
O1 C1 N1 124.21(16) . . ?
O2 C1 N1 108.92(14) . . ?
N1 C2 H2 107.0 . . ?
N1 C2 C3 112.06(14) . . ?
N1 C2 C11 111.41(14) . . ?
C3 C2 H2 107.0 . . ?
C11 C2 H2 107.0 . . ?
C11 C2 C3 112.00(14) . . ?
F1 C3 N2 104.42(14) . . ?
F1 C3 C2 106.88(14) . . ?
F1 C3 C4 109.07(15) . . ?
N2 C3 C2 109.59(14) . . ?
C4 C3 N2 109.28(15) . . ?
C4 C3 C2 116.85(15) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C5 112.31(16) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.81(16) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C8 C6 C5 119.28(18) . . ?
C01L C6 C5 122.40(19) . . ?
C01L C6 C8 118.20(18) . . ?
C6 C8 H8 119.5 . . ?
C15 C8 C6 121.0(2) . . ?
C15 C8 H8 119.5 . . ?
C10 C9 H9 120.2 . . ?
C10 C9 C15 119.7(2) . . ?
C15 C9 H9 120.2 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C01L 120.25(19) . . ?
C01L C10 H10 119.9 . . ?
C2 C11 H11A 108.4 . . ?
C2 C11 H11B 108.4 . . ?
C2 C11 C12 115.53(14) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C13 C12 C11 107.09(15) . . ?
C13 C12 C14 108.97(15) . . ?
C14 C12 C11 112.10(15) . . ?
C1D C12 C11 110.27(15) . . ?
C1D C12 C13 109.02(16) . . ?
C1D C12 C14 109.31(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15 119.9 . . ?
C9 C15 C8 120.2(2) . . ?
C9 C15 H15 119.9 . . ?
O2 C16 C17 101.86(14) . . ?
O2 C16 C18 109.06(14) . . ?
O2 C16 C19 110.44(15) . . ?
C17 C16 C18 110.68(16) . . ?
C17 C16 C19 110.52(16) . . ?
C18 C16 C19 113.63(15) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C1D H1DA 109.5 . . ?
C12 C1D H1DB 109.5 . . ?
C12 C1D H1DC 109.5 . . ?
H1DA C1D H1DB 109.5 . . ?
H1DA C1D H1DC 109.5 . . ?
H1DB C1D H1DC 109.5 . . ?
C6 C01L C10 120.7(2) . . ?
C6 C01L H01L 119.7 . . ?
C10 C01L H01L 119.7 . . ?
C6B C7 H7 119.6 . . ?
C6B C7 C10B 120.73(19) . . ?
C10B C7 H7 119.6 . . ?
C1B O2B C16B 121.70(14) . . ?
C1B N1B H1B 118.8 . . ?
C1B N1B C2B 122.32(15) . . ?
C2B N1B H1B 118.8 . . ?
O3B N2B C3B 115.51(14) . . ?
O4B N2B O3B 125.25(16) . . ?
O4B N2B C3B 119.24(15) . . ?
O1B C1B O2B 126.58(16) . . ?
O1B C1B N1B 125.01(16) . . ?
O2B C1B N1B 108.41(15) . . ?
N1B C2B H2B 107.1 . . ?
N1B C2B C3B 113.11(14) . . ?
N1B C2B C11B 110.91(14) . . ?
C3B C2B H2B 107.1 . . ?
C11B C2B H2B 107.1 . . ?
C11B C2B C3B 111.29(14) . . ?
F1B C3B N2B 105.11(13) . . ?
F1B C3B C2B 106.36(14) . . ?
F1B C3B C4B 109.12(14) . . ?
N2B C3B C2B 110.49(13) . . ?
C4B C3B N2B 108.31(14) . . ?
C4B C3B C2B 116.82(14) . . ?
C3B C4B H4BA 109.3 . . ?
C3B C4B H4BB 109.3 . . ?
C3B C4B C5B 111.56(15) . . ?
H4BA C4B H4BB 108.0 . . ?
C5B C4B H4BA 109.3 . . ?
C5B C4B H4BB 109.3 . . ?
C4B C5B H5BA 108.6 . . ?
C4B C5B H5BB 108.6 . . ?
H5BA C5B H5BB 107.6 . . ?
C6B C5B C4B 114.54(15) . . ?
C6B C5B H5BA 108.6 . . ?
C6B C5B H5BB 108.6 . . ?
C7 C6B C5B 120.26(17) . . ?
C7 C6B C7B 118.36(17) . . ?
C7B C6B C5B 121.21(17) . . ?
C6B C7B H7B 119.5 . . ?
C8B C7B C6B 120.94(19) . . ?
C8B C7B H7B 119.5 . . ?
C7B C8B H8B 120.0 . . ?
C7B C8B C9B 120.1(2) . . ?
C9B C8B H8B 120.0 . . ?
C8B C9B H9B 120.1 . . ?
C10B C9B C8B 119.71(19) . . ?
C10B C9B H9B 120.1 . . ?
C7 C10B H10B 119.9 . . ?
C9B C10B C7 120.18(19) . . ?
C9B C10B H10B 119.9 . . ?
C2B C11B H11C 108.4 . . ?
C2B C11B H11D 108.4 . . ?
C2B C11B C12B 115.42(14) . . ?
H11C C11B H11D 107.5 . . ?
C12B C11B H11C 108.4 . . ?
C12B C11B H11D 108.4 . . ?
C13B C12B C11B 107.19(15) . . ?
C14B C12B C11B 111.34(15) . . ?
C14B C12B C13B 109.87(15) . . ?
C15B C12B C11B 110.44(15) . . ?
C15B C12B C13B 108.45(15) . . ?
C15B C12B C14B 109.50(16) . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C12B C14B H14D 109.5 . . ?
C12B C14B H14E 109.5 . . ?
C12B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C12B C15B H15A 109.5 . . ?
C12B C15B H15B 109.5 . . ?
C12B C15B H15C 109.5 . . ?
H15A C15B H15B 109.5 . . ?
H15A C15B H15C 109.5 . . ?
H15B C15B H15C 109.5 . . ?
O2B C16B C17B 101.82(15) . . ?
O2B C16B C18B 108.87(15) . . ?
O2B C16B C19B 110.60(15) . . ?
C18B C16B C17B 111.41(18) . . ?
C19B C16B C17B 110.51(17) . . ?
C19B C16B C18B 113.05(18) . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C16B C18B H18D 109.5 . . ?
C16B C18B H18E 109.5 . . ?
C16B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C16B C19B H19D 109.5 . . ?
C16B C19B H19E 109.5 . . ?
C16B C19B H19F 109.5 . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C6C C1A H1A 119.2 . . ?
C10C C1A H1A 119.2 . . ?
C10C C1A C6C 121.6(3) . . ?
C1C O2C C16C 120.30(13) . . ?
C1C N1C H1C 119.3 . . ?
C1C N1C C2C 121.49(14) . . ?
C2C N1C H1C 119.3 . . ?
O3C N2C C3C 116.29(14) . . ?
O4C N2C O3C 124.99(16) . . ?
O4C N2C C3C 118.67(15) . . ?
O1C C1C O2C 126.30(16) . . ?
O1C C1C N1C 124.61(16) . . ?
O2C C1C N1C 109.09(14) . . ?
N1C C2C H2C 106.4 . . ?
N1C C2C C3C 111.49(14) . . ?
N1C C2C C11C 111.91(14) . . ?
C3C C2C H2C 106.4 . . ?
C11C C2C H2C 106.4 . . ?
C11C C2C C3C 113.71(14) . . ?
F1C C3C N2C 104.87(13) . . ?
F1C C3C C2C 107.69(14) . . ?
F1C C3C C4C 109.97(14) . . ?
N2C C3C C2C 109.58(14) . . ?
C4C C3C N2C 109.89(14) . . ?
C4C C3C C2C 114.40(14) . . ?
C3C C4C H4CA 108.8 . . ?
C3C C4C H4CB 108.8 . . ?
C3C C4C C5C 113.85(15) . . ?
H4CA C4C H4CB 107.7 . . ?
C5C C4C H4CA 108.8 . . ?
C5C C4C H4CB 108.8 . . ?
C4C C5C H5CA 109.5 . . ?
C4C C5C H5CB 109.5 . . ?
H5CA C5C H5CB 108.1 . . ?
C6C C5C C4C 110.60(15) . . ?
C6C C5C H5CA 109.5 . . ?
C6C C5C H5CB 109.5 . . ?
C1A C6C C5C 120.0(2) . . ?
C1A C6C C7C 119.1(2) . . ?
C7C C6C C5C 120.94(19) . . ?
C6C C7C H7C 120.5 . . ?
C6C C7C C8C 119.0(3) . . ?
C8C C7C H7C 120.5 . . ?
C7C C8C H8C 119.8 . . ?
C9C C8C C7C 120.3(3) . . ?
C9C C8C H8C 119.8 . . ?
C8C C9C H9C 120.0 . . ?
C10C C9C C8C 120.1(2) . . ?
C10C C9C H9C 120.0 . . ?
C1A C10C H10C 120.1 . . ?
C9C C10C C1A 119.8(3) . . ?
C9C C10C H10C 120.1 . . ?
C2C C11C H11E 108.7 . . ?
C2C C11C H11F 108.7 . . ?
C2C C11C C12C 114.11(14) . . ?
H11E C11C H11F 107.6 . . ?
C12C C11C H11E 108.7 . . ?
C12C C11C H11F 108.7 . . ?
C13C C12C C11C 108.13(15) . . ?
C14C C12C C11C 111.89(16) . . ?
C14C C12C C13C 109.14(16) . . ?
C15C C12C C11C 109.37(16) . . ?
C15C C12C C13C 107.99(16) . . ?
C15C C12C C14C 110.23(18) . . ?
C12C C13C H13G 109.5 . . ?
C12C C13C H13H 109.5 . . ?
C12C C13C H13I 109.5 . . ?
H13G C13C H13H 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
C12C C14C H14G 109.5 . . ?
C12C C14C H14H 109.5 . . ?
C12C C14C H14I 109.5 . . ?
H14G C14C H14H 109.5 . . ?
H14G C14C H14I 109.5 . . ?
H14H C14C H14I 109.5 . . ?
C12C C15C H15D 109.5 . . ?
C12C C15C H15E 109.5 . . ?
C12C C15C H15F 109.5 . . ?
H15D C15C H15E 109.5 . . ?
H15D C15C H15F 109.5 . . ?
H15E C15C H15F 109.5 . . ?
O2C C16C C17C 101.94(15) . . ?
O2C C16C C18C 108.66(15) . . ?
O2C C16C C19C 110.69(15) . . ?
C18C C16C C17C 110.81(18) . . ?
C18C C16C C19C 113.50(17) . . ?
C19C C16C C17C 110.61(16) . . ?
C16C C17C H17G 109.5 . . ?
C16C C17C H17H 109.5 . . ?
C16C C17C H17I 109.5 . . ?
H17G C17C H17H 109.5 . . ?
H17G C17C H17I 109.5 . . ?
H17H C17C H17I 109.5 . . ?
C16C C18C H18G 109.5 . . ?
C16C C18C H18H 109.5 . . ?
C16C C18C H18I 109.5 . . ?
H18G C18C H18H 109.5 . . ?
H18G C18C H18I 109.5 . . ?
H18H C18C H18I 109.5 . . ?
C16C C19C H19G 109.5 . . ?
C16C C19C H19H 109.5 . . ?
C16C C19C H19I 109.5 . . ?
H19G C19C H19H 109.5 . . ?
H19G C19C H19I 109.5 . . ?
H19H C19C H19I 109.5 . . ?

_olex2_date_sample_data_collection 2019-10-31
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.063
_oxdiff_exptl_absorpt_empirical_full_min 0.903
####################################################################### 
# 
# 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_bav-6-286
_database_code_depnum_ccdc_archive 'CCDC 2118056'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2019-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 Cl F N2 O4'
_chemical_formula_sum            'C21 H24 Cl F N2 O4'
_chemical_formula_weight         422.87
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H24ClFN2O4
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'
Cl Cl 0.3639 0.7018 '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                   12.8885(3)
_cell_length_b                   5.3127(2)
_cell_length_c                   15.1705(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.058(2)
_cell_angle_gamma                90
_cell_volume                     1034.72(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6589
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.1280
_cell_measurement_theta_min      3.4290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.972
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 0 6 0.0045
-6 0 -6 0.0125
7 0 -6 0.0169
-7 0 6 0.0119
1 -3 0 0.1215
-1 3 0 0.1215

_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.017
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.9961 0.0003 5.9775 -0.9799 0.0536 -0.0419
-5.9961 -0.0003 -5.9775 0.9799 -0.0536 0.0419
7.0075 0.0013 -6.0030 -0.3020 -0.9271 0.2058
-7.0075 -0.0013 6.0030 0.3020 0.9271 -0.2058
0.9953 -2.9984 -0.0179 -0.0721 -0.2636 -0.8335
-0.9953 2.9984 0.0179 0.0721 0.2636 0.8335

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13856
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.299
_diffrn_reflns_theta_min         2.924
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -20.00   1.00    5.58    --  -36.45 -57.00  60.00   84
  2  ω   -104.00 -10.00   1.00    5.58    --  -36.45 -77.00 -60.00   94
  3  ω    -53.00  31.00   1.00    5.58    --  -36.45  57.00-120.00   84
  4  ω   -104.00 -10.00   1.00    5.58    --  -36.45 -77.00  90.00   94
  5  ω    -53.00  31.00   1.00    5.58    --  -36.45  57.00 150.00   84
  6  ω   -104.00 -10.00   1.00    5.58    --  -36.45 -77.00  30.00   94
  7  ω   -106.00 -18.00   1.00    5.58    --  -36.45 -38.00  90.00   88
  8  ω    -33.00  55.00   1.00    5.58    --   36.45 -38.00 -60.00   88
  9  ω    -31.00  63.00   1.00    5.58    --   36.45 -77.00  60.00   94
 10  ω     20.00 104.00   1.00    5.58    --   36.45  57.00 120.00   84
 11  ω     10.00 104.00   1.00    5.58    --   36.45  77.00-150.00   94
 12  ω     70.00 178.00   1.00   22.33    --  108.65  15.00 150.00  108
 13  ω     91.00 176.00   1.00   22.33    --  108.65  61.00 120.00   85
 14  ω     82.00 176.00   1.00   22.33    --  108.65  77.00 120.00   94
 15  ω     70.00 178.00   1.00   22.33    --  108.65  15.00  90.00  108
 16  ω     40.00 126.00   1.00   22.33    --  108.65 -45.00-120.00   86
 17  ω     87.00 178.00   1.00   22.33    --  108.65  30.00 120.00   91
 18  ω     87.00 178.00   1.00   22.33    --  108.65  30.00 150.00   91
 19  ω     41.00 137.00   1.00   22.33    --  108.65 -80.00  59.85   96
 20  ω     82.00 176.00   1.00   22.33    --  108.65  77.00   0.00   94
 21  ω     82.00 176.00   1.00   22.33    --  108.65  77.00  30.00   94
 22  ω     40.00 126.00   1.00   22.33    --  108.65 -45.00   0.00   86
 23  ω     87.00 178.00   1.00   22.33    --  108.65  30.00  90.00   91
 24  ω     91.00 176.00   1.00   22.33    --  108.65  61.00  90.00   85
 25  ω     82.00 176.00   1.00   22.33    --  108.65  77.00 150.00   94
 26  ω     82.00 176.00   1.00   22.33    --  108.65  77.00  90.00   94
 27  ω     87.00 178.00   1.00   22.33    --  108.65  30.00-180.00   91
 28  ω     91.00 176.00   1.00   22.33    --  108.65  61.00  30.00   85
 29  ω     91.00 118.00   1.00   22.33    --  108.65  30.00  60.00   27
 30  ω    149.00 176.00   1.00   22.33    --  108.65  61.00 150.00   27
 31  ω     82.00 108.00   1.00   22.33    --  108.65  77.00  60.00   26
 32  ω     92.00 117.00   1.00   22.33    --  108.65  61.00 150.00   25
 33  ω     92.00 117.00   1.00   22.33    --  108.65  61.00  60.00   25
 34  ω     92.00 119.00   1.00   22.33    --  108.65  45.00  60.00   27
 35  ω     94.00 148.00   1.00   22.33    --  108.65  45.00 120.00   54
 36  ω    122.00 177.00   1.00   22.33    --  108.65  15.00-120.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0987047000
_diffrn_orient_matrix_UB_12      -0.0083228000
_diffrn_orient_matrix_UB_13      -0.0649164000
_diffrn_orient_matrix_UB_21      -0.0670317000
_diffrn_orient_matrix_UB_22      0.0652016000
_diffrn_orient_matrix_UB_23      0.0762010000
_diffrn_orient_matrix_UB_31      0.0125301000
_diffrn_orient_matrix_UB_32      0.2822733000
_diffrn_orient_matrix_UB_33      -0.0196001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.779
_reflns_Friedel_fraction_max     0.751
_reflns_number_gt                3532
_reflns_number_total             3635
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.537
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.049
_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)+(0.0519P)²+0.2614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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
Cl1 Cl -0.07035(4) 0.88784(15) 0.07046(4) 0.02325(17) Uani 1 1 d . . . . .
F1 F 0.34817(14) 0.8706(4) 0.34146(10) 0.0300(4) Uani 1 1 d . . . . .
O1 O 0.52340(19) 0.7020(7) 0.39638(18) 0.0477(8) Uani 1 1 d . . . . .
O2 O 0.4675(2) 0.3164(7) 0.40232(18) 0.0446(7) Uani 1 1 d . . . . .
O3 O 0.45469(15) 0.1328(4) 0.17898(13) 0.0231(4) Uani 1 1 d . . . . .
O4 O 0.56359(14) 0.4480(4) 0.14300(12) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.4563(2) 0.5358(7) 0.38682(17) 0.0309(7) Uani 1 1 d . . . . .
N2 N 0.42283(17) 0.5465(5) 0.20761(14) 0.0189(5) Uani 1 1 d . . . . .
H2 H 0.441343 0.699479 0.199182 0.023 Uiso 1 1 calc R . . . .
C1 C 0.33173(19) 0.4946(6) 0.25480(16) 0.0174(6) Uani 1 1 d . . . . .
H1 H 0.325849 0.311786 0.261288 0.021 Uiso 1 1 calc R . . . .
C2 C 0.3476(2) 0.6113(7) 0.34850(18) 0.0220(6) Uani 1 1 d . . . . .
C3 C 0.2680(2) 0.5302(7) 0.41103(16) 0.0202(6) Uani 1 1 d . . . . .
H3A H 0.267653 0.347856 0.414398 0.024 Uiso 1 1 calc R . . . .
H3B H 0.199403 0.583700 0.386803 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2891(2) 0.6377(7) 0.50505(17) 0.0266(7) Uani 1 1 d . . . . .
H4A H 0.352652 0.565370 0.533389 0.032 Uiso 1 1 calc R . . . .
H4B H 0.298204 0.818616 0.502093 0.032 Uiso 1 1 calc R . . . .
C5 C 0.1986(2) 0.5771(7) 0.55884(16) 0.0223(6) Uani 1 1 d . . . . .
C6 C 0.1990(2) 0.3644(7) 0.61194(17) 0.0259(6) Uani 1 1 d . . . . .
H6 H 0.256134 0.256764 0.615325 0.031 Uiso 1 1 calc R . . . .
C7 C 0.1149(2) 0.3106(7) 0.66012(18) 0.0264(7) Uani 1 1 d . . . . .
H7 H 0.115988 0.167080 0.695283 0.032 Uiso 1 1 calc R . . . .
C8 C 0.0294(2) 0.4695(7) 0.65609(18) 0.0277(7) Uani 1 1 d . . . . .
H8 H -0.026467 0.434133 0.688905 0.033 Uiso 1 1 calc R . . . .
C9 C 0.0277(2) 0.6814(7) 0.6028(2) 0.0301(8) Uani 1 1 d . . . . .
H9 H -0.029551 0.788507 0.599494 0.036 Uiso 1 1 calc R . . . .
C10 C 0.1119(2) 0.7339(7) 0.55438(18) 0.0255(6) Uani 1 1 d . . . . .
H10 H 0.110123 0.876011 0.518469 0.031 Uiso 1 1 calc R . . . .
C11 C 0.23094(19) 0.5906(6) 0.20599(16) 0.0170(6) Uani 1 1 d . . . . .
C12 C 0.13797(19) 0.4596(6) 0.21250(16) 0.0170(6) Uani 1 1 d . . . . .
H12 H 0.138455 0.311838 0.245402 0.020 Uiso 1 1 calc R . . . .
C13 C 0.0447(2) 0.5473(6) 0.17043(16) 0.0180(6) Uani 1 1 d . . . . .
H13 H -0.017107 0.459651 0.174959 0.022 Uiso 1 1 calc R . . . .
C14 C 0.04549(19) 0.7670(6) 0.12179(16) 0.0181(6) Uani 1 1 d . . . . .
C15 C 0.13705(19) 0.8992(7) 0.11288(16) 0.0188(5) Uani 1 1 d . . . . .
H15 H 0.136371 1.045308 0.079081 0.023 Uiso 1 1 calc R . . . .
C16 C 0.2293(2) 0.8096(6) 0.15517(16) 0.0188(6) Uani 1 1 d . . . . .
H16 H 0.290966 0.896621 0.149619 0.023 Uiso 1 1 calc R . . . .
C17 C 0.47901(19) 0.3529(6) 0.17665(15) 0.0173(6) Uani 1 1 d . . . . .
C18 C 0.64797(19) 0.2778(6) 0.12022(17) 0.0176(6) Uani 1 1 d . . . . .
C19 C 0.7289(2) 0.4637(7) 0.0921(2) 0.0279(7) Uani 1 1 d . . . . .
H19A H 0.700137 0.557413 0.041599 0.042 Uiso 1 1 calc GR . . . .
H19B H 0.789394 0.373373 0.076904 0.042 Uiso 1 1 calc GR . . . .
H19C H 0.748259 0.577248 0.139923 0.042 Uiso 1 1 calc GR . . . .
C20 C 0.6904(2) 0.1363(7) 0.20239(18) 0.0254(7) Uani 1 1 d . . . . .
H20A H 0.705573 0.253113 0.250062 0.038 Uiso 1 1 calc GR . . . .
H20B H 0.753034 0.049363 0.190576 0.038 Uiso 1 1 calc GR . . . .
H20C H 0.639596 0.016669 0.218571 0.038 Uiso 1 1 calc GR . . . .
C21 C 0.6114(2) 0.1063(7) 0.04419(19) 0.0249(6) Uani 1 1 d . . . . .
H21A H 0.565046 -0.018410 0.064380 0.037 Uiso 1 1 calc GR . . . .
H21B H 0.670351 0.024830 0.022192 0.037 Uiso 1 1 calc GR . . . .
H21C H 0.575441 0.203742 -0.002285 0.037 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
Cl1 C14 1.744(3) . ?
F1 C2 1.381(4) . ?
O1 N1 1.235(4) . ?
O2 N1 1.195(5) . ?
O3 C17 1.212(4) . ?
O4 C17 1.343(3) . ?
O4 C18 1.478(3) . ?
N1 C2 1.523(4) . ?
N2 H2 0.8600 . ?
N2 C1 1.454(3) . ?
N2 C17 1.365(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.548(4) . ?
C1 C11 1.525(4) . ?
C2 C3 1.519(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.538(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.516(4) . ?
C5 C6 1.388(5) . ?
C5 C10 1.391(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(4) . ?
C11 C16 1.395(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(4) . ?
C14 C15 1.390(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C18 C19 1.525(4) . ?
C18 C20 1.516(4) . ?
C18 C21 1.512(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O4 C18 119.8(2) . . ?
O1 N1 C2 117.9(3) . . ?
O2 N1 O1 127.1(3) . . ?
O2 N1 C2 115.0(3) . . ?
C1 N2 H2 119.9 . . ?
C17 N2 H2 119.9 . . ?
C17 N2 C1 120.2(3) . . ?
N2 C1 H1 108.1 . . ?
N2 C1 C2 109.2(2) . . ?
N2 C1 C11 112.8(2) . . ?
C2 C1 H1 108.1 . . ?
C11 C1 H1 108.1 . . ?
C11 C1 C2 110.5(2) . . ?
F1 C2 N1 106.3(3) . . ?
F1 C2 C1 109.2(2) . . ?
F1 C2 C3 109.9(3) . . ?
N1 C2 C1 106.7(2) . . ?
C3 C2 N1 109.6(2) . . ?
C3 C2 C1 114.7(2) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.6(2) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.8(2) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 C10 118.6(3) . . ?
C10 C5 C4 120.0(3) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.9(3) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 121.0(3) . . ?
C5 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C1 119.9(3) . . ?
C16 C11 C1 121.2(2) . . ?
C16 C11 C12 118.9(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.7(2) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 Cl1 120.2(2) . . ?
C13 C14 C15 121.7(3) . . ?
C15 C14 Cl1 118.1(2) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.5 . . ?
O3 C17 O4 126.5(3) . . ?
O3 C17 N2 124.8(2) . . ?
O4 C17 N2 108.7(3) . . ?
O4 C18 C19 101.8(2) . . ?
O4 C18 C20 109.3(2) . . ?
O4 C18 C21 111.1(2) . . ?
C20 C18 C19 110.2(2) . . ?
C21 C18 C19 110.6(2) . . ?
C21 C18 C20 113.2(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_date_sample_data_collection 2019-07-23
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.806
####################################################################### 
# 
# 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_jab-4-237
_database_code_depnum_ccdc_archive 'CCDC 2118053'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2019-10-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H32 N2 O4'
_chemical_formula_sum            'C20 H32 N2 O4'
_chemical_formula_weight         364.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H32N2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   11.84105(5)
_cell_length_b                   11.84105(5)
_cell_length_c                   27.02804(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3281.90(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    39640
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.2310
_cell_measurement_theta_min      4.2980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.474
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1188
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 7 0 0.0586
1 -7 0 0.0586
-8 5 -1 0.0534
8 -5 1 0.0534
-1 -1 -17 0.1380
1 1 17 0.1380

_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.107
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 7.0000 -0.0000 0.9733 0.1233 -0.0940
1.0000 -7.0000 0.0000 -0.9733 -0.1233 0.0940
-8.0000 5.0000 -0.9998 0.1239 0.8251 -0.6424
8.0000 -5.0000 0.9998 -0.1239 -0.8251 0.6424
-1.0000 -1.0000 -16.9999 -0.2354 -0.4489 -0.8655
1.0000 1.0000 16.9999 0.2354 0.4489 0.8655

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            62164
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.350
_diffrn_reflns_theta_min         4.311
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  33.00   1.00    1.00    --  -36.45  38.00  60.00   88
  2  ω   -108.00  -7.00   1.00    1.00    --  -36.45 -19.00 -90.00  101
  3  ω     23.00  90.00   1.00    1.00    --   36.45-125.00  90.00   67
  4  ω    -31.00  53.00   1.00    1.00    --   36.45 -57.00 150.00   84
  5  ω     20.00 104.00   1.00    1.00    --   36.45  57.00  30.00   84
  6  ω     23.00  90.00   1.00    1.00    --   36.45-125.00-180.00   67
  7  ω     20.00 104.00   1.00    1.00    --   36.45  57.00 150.00   84
  8  ω     23.00  90.00   1.00    1.00    --   36.45-125.00  30.00   67
  9  ω     20.00 104.00   1.00    1.00    --   36.45  57.00 -90.00   84
 10  ω     39.00 109.00   1.00    2.23    --  108.65 -94.00 -60.00   70
 11  ω     39.00 109.00   1.00    2.23    --  108.65 -94.00-120.00   70
 12  ω     39.00 109.00   1.00    2.23    --  108.65 -94.00  30.00   70
 13  ω     39.00 130.00   1.00    2.23    --  108.65 -30.00-120.00   91
 14  ω     39.00 115.00   1.00    2.23    --  108.65-111.00 150.00   76
 15  ω     70.00 178.00   1.00    2.23    --  108.65  15.00-150.00  108
 16  ω     91.00 177.00   1.00    2.23    --  108.65  45.00-180.00   86
 17  ω     39.00 178.00   1.00    2.23    --  108.65   0.00 -30.00  139
 18  ω     40.00 126.00   1.00    2.23    --  108.65 -45.00   0.00   86
 19  ω     40.00 126.00   1.00    2.23    --  108.65 -45.00  90.00   86
 20  ω     42.00 127.00   1.00    2.23    --  108.65 -61.00-120.00   85
 21  ω     40.00 126.00   1.00    2.23    --  108.65 -45.00 150.00   86
 22  ω     39.00 115.00   1.00    2.23    --  108.65-111.00-150.00   76
 23  ω     42.00 127.00   1.00    2.23    --  108.65 -61.00   0.00   85
 24  ω    -53.00  31.00   1.00    1.00    --  -36.45  57.00  90.00   84
 25  ω    -31.00  53.00   1.00    1.00    --   36.45 -57.00-120.00   84
 26  ω     10.00 104.00   1.00    1.00    --   36.45  77.00 -60.00   94
 27  ω    -33.00  55.00   1.00    1.00    --   36.45 -38.00 -90.00   88
 28  ω     10.00 104.00   1.00    1.00    --   36.45  77.00-180.00   94
 29  ω     20.00 104.00   1.00    1.00    --   36.45  57.00  90.00   84
 30  ω     70.00 178.00   1.00    2.23    --  108.65  15.00  90.00  108
 31  ω     82.00 176.00   1.00    2.23    --  108.65  77.00 120.00   94
 32  ω     91.00 177.00   1.00    2.23    --  108.65  45.00 -30.00   86
 33  ω     82.00 176.00   1.00    2.23    --  108.65  77.00-150.00   94
 34  ω     82.00 176.00   1.00    2.23    --  108.65  77.00 -90.00   94
 35  ω     87.00 178.00   1.00    2.23    --  108.65  30.00 120.00   91
 36  ω     82.00 176.00   1.00    2.23    --  108.65  77.00-120.00   94
 37  ω     82.00 176.00   1.00    2.23    --  108.65  77.00   0.00   94
 38  ω     82.00 176.00   1.00    2.23    --  108.65  77.00  60.00   94
 39  ω     82.00 176.00   1.00    2.23    --  108.65  77.00-180.00   94
 40  ω     82.00 176.00   1.00    2.23    --  108.65  77.00  30.00   94
 41  ω     91.00 177.00   1.00    2.23    --  108.65  45.00   0.00   86
 42  ω     10.00 104.00   1.00    1.00    --   36.45  77.00  30.00   94
 43  ω     10.00 104.00   1.00    1.00    --   36.45  77.00 -90.00   94
 44  ω     23.00  90.00   1.00    1.00    --   36.45-125.00-120.00   67
 45  ω     10.00 104.00   1.00    1.00    --   36.45  77.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0783614000
_diffrn_orient_matrix_UB_12      0.1502438000
_diffrn_orient_matrix_UB_13      0.0004024000
_diffrn_orient_matrix_UB_21      -0.1056174000
_diffrn_orient_matrix_UB_22      0.0025281000
_diffrn_orient_matrix_UB_23      0.0324706000
_diffrn_orient_matrix_UB_31      0.0725380000
_diffrn_orient_matrix_UB_32      -0.0030592000
_diffrn_orient_matrix_UB_33      0.0468276000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4213
_reflns_number_total             4242
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.160
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.082
_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)+(0.0424P)²+0.3618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          'Refined without restraint.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.06766(11) 0.15660(12) 0.51173(4) 0.0247(2) Uani 1 1 d . . . . .
O2 O -0.14251(11) 0.09469(12) 0.43276(4) 0.0241(2) Uani 1 1 d . . . . .
O3 O 0.37986(15) 0.32585(14) 0.54591(6) 0.0417(3) Uani 1 1 d . . . . .
O4 O 0.49181(13) 0.31310(15) 0.48512(6) 0.0446(4) Uani 1 1 d . . . . .
N1 N 0.06907(13) 0.20446(13) 0.44620(5) 0.0214(3) Uani 1 1 d . . . . .
H1 H 0.073780 0.190679 0.415228 0.026 Uiso 1 1 calc R . . . .
N2 N 0.38900(14) 0.28955(14) 0.50445(6) 0.0304(3) Uani 1 1 d . . . . .
C1 C -0.04956(15) 0.15169(15) 0.46755(6) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.18937(15) 0.28373(15) 0.47345(6) 0.0209(3) Uani 1 1 d . . . . .
H2 H 0.167739 0.297060 0.507149 0.025 Uiso 1 1 calc R . . . .
C3 C 0.26417(15) 0.20822(16) 0.47598(6) 0.0237(3) Uani 1 1 d . . . . .
H3 H 0.285347 0.193938 0.442345 0.028 Uiso 1 1 calc R . . . .
C4 C 0.18978(17) 0.07744(16) 0.50256(7) 0.0265(3) Uani 1 1 d . . . . .
H4A H 0.105650 0.025512 0.486736 0.032 Uiso 1 1 calc R . . . .
H4B H 0.174269 0.092569 0.536513 0.032 Uiso 1 1 calc R . . . .
C5 C 0.26216(19) 0.00023(18) 0.50252(8) 0.0343(4) Uani 1 1 d . . . . .
H5A H 0.268997 -0.023763 0.468797 0.041 Uiso 1 1 calc R . . . .
H5B H 0.349835 0.055260 0.515063 0.041 Uiso 1 1 calc R . . . .
C6 C 0.19420(17) -0.12099(17) 0.53358(7) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.2531(2) -0.13561(18) 0.57550(8) 0.0350(4) Uani 1 1 d . . . . .
H7 H 0.337245 -0.070950 0.583646 0.042 Uiso 1 1 calc R . . . .
C8 C 0.1890(2) -0.24485(19) 0.60558(8) 0.0394(5) Uani 1 1 d . . . . .
H8 H 0.229896 -0.252830 0.633640 0.047 Uiso 1 1 calc R . . . .
C9 C 0.0645(2) -0.34133(19) 0.59368(8) 0.0398(5) Uani 1 1 d . . . . .
H9 H 0.020774 -0.414016 0.614002 0.048 Uiso 1 1 calc R . . . .
C10 C 0.0047(2) -0.33026(19) 0.55168(9) 0.0400(5) Uani 1 1 d . . . . .
H10 H -0.078840 -0.396192 0.543437 0.048 Uiso 1 1 calc R . . . .
C11 C 0.06865(19) -0.22114(19) 0.52173(9) 0.0367(4) Uani 1 1 d . . . . .
H11 H 0.027667 -0.214430 0.493440 0.044 Uiso 1 1 calc R . . . .
C12 C 0.27084(15) 0.41718(15) 0.44840(6) 0.0230(3) Uani 1 1 d . . . . .
H12A H 0.258893 0.404807 0.412910 0.028 Uiso 1 1 calc R . . . .
H12B H 0.362098 0.448049 0.455291 0.028 Uiso 1 1 calc R . . . .
C13 C 0.24079(16) 0.52522(16) 0.46360(7) 0.0270(4) Uani 1 1 d . . . . .
C14 C 0.2798(2) 0.5648(2) 0.51730(8) 0.0398(5) Uani 1 1 d . . . . .
H14A H 0.228219 0.491784 0.538519 0.060 Uiso 1 1 calc GR . . . .
H14B H 0.265224 0.635344 0.525659 0.060 Uiso 1 1 calc GR . . . .
H14C H 0.370398 0.592309 0.521549 0.060 Uiso 1 1 calc GR . . . .
C15 C 0.09670(19) 0.4828(2) 0.45649(10) 0.0407(5) Uani 1 1 d . . . . .
H15A H 0.071731 0.455120 0.422908 0.061 Uiso 1 1 calc GR . . . .
H15B H 0.083453 0.554731 0.463620 0.061 Uiso 1 1 calc GR . . . .
H15C H 0.044554 0.411822 0.478482 0.061 Uiso 1 1 calc GR . . . .
C16 C 0.3231(2) 0.64406(18) 0.43069(9) 0.0404(5) Uani 1 1 d . . . . .
H16A H 0.413618 0.670529 0.434352 0.061 Uiso 1 1 calc GR . . . .
H16B H 0.309456 0.714384 0.440342 0.061 Uiso 1 1 calc GR . . . .
H16C H 0.297665 0.621709 0.396766 0.061 Uiso 1 1 calc GR . . . .
C17 C -0.28132(15) 0.04543(18) 0.44439(7) 0.0283(4) Uani 1 1 d . . . . .
C18 C -0.32995(19) -0.0665(2) 0.48096(8) 0.0436(5) Uani 1 1 d . . . . .
H18A H -0.304437 -0.127645 0.470027 0.065 Uiso 1 1 calc GR . . . .
H18B H -0.423294 -0.109292 0.483043 0.065 Uiso 1 1 calc GR . . . .
H18C H -0.292878 -0.033356 0.512939 0.065 Uiso 1 1 calc GR . . . .
C19 C -0.34503(18) -0.0041(2) 0.39418(7) 0.0337(4) Uani 1 1 d . . . . .
H19A H -0.310595 0.066766 0.370992 0.051 Uiso 1 1 calc GR . . . .
H19B H -0.437563 -0.040083 0.397119 0.051 Uiso 1 1 calc GR . . . .
H19C H -0.327157 -0.070369 0.382739 0.051 Uiso 1 1 calc GR . . . .
C20 C -0.2984(2) 0.1572(2) 0.46185(9) 0.0427(5) Uani 1 1 d . . . . .
H20A H -0.259734 0.184959 0.493990 0.064 Uiso 1 1 calc GR . . . .
H20B H -0.389651 0.129107 0.463680 0.064 Uiso 1 1 calc GR . . . .
H20C H -0.256619 0.228458 0.438988 0.064 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.220(2) . ?
O2 C1 1.3447(19) . ?
O2 C17 1.4772(19) . ?
O3 N2 1.224(2) . ?
O4 N2 1.222(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.349(2) . ?
N1 C2 1.454(2) . ?
N2 C3 1.510(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.543(2) . ?
C2 C12 1.537(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.525(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.534(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.503(2) . ?
C6 C7 1.386(3) . ?
C6 C11 1.399(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.545(2) . ?
C13 C14 1.524(3) . ?
C13 C15 1.531(2) . ?
C13 C16 1.533(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.517(3) . ?
C17 C19 1.521(2) . ?
C17 C20 1.511(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C17 121.29(13) . . ?
C1 N1 H1 118.7 . . ?
C1 N1 C2 122.64(13) . . ?
C2 N1 H1 118.7 . . ?
O3 N2 C3 117.39(14) . . ?
O4 N2 O3 124.35(17) . . ?
O4 N2 C3 118.25(17) . . ?
O1 C1 O2 126.10(15) . . ?
O1 C1 N1 124.33(15) . . ?
O2 C1 N1 109.56(14) . . ?
N1 C2 H2 108.9 . . ?
N1 C2 C3 108.01(13) . . ?
N1 C2 C12 110.44(13) . . ?
C3 C2 H2 108.9 . . ?
C12 C2 H2 108.9 . . ?
C12 C2 C3 111.61(13) . . ?
N2 C3 C2 108.39(13) . . ?
N2 C3 H3 109.2 . . ?
N2 C3 C4 106.96(13) . . ?
C2 C3 H3 109.2 . . ?
C4 C3 C2 113.69(13) . . ?
C4 C3 H3 109.2 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.18(14) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C4 112.14(15) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C7 C6 C5 120.90(17) . . ?
C7 C6 C11 117.99(17) . . ?
C11 C6 C5 121.10(18) . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.34(18) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.07(19) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.16(19) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C2 C12 H12A 108.1 . . ?
C2 C12 H12B 108.1 . . ?
C2 C12 C13 116.63(14) . . ?
H12A C12 H12B 107.3 . . ?
C13 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
C14 C13 C12 110.38(15) . . ?
C14 C13 C15 109.68(17) . . ?
C14 C13 C16 108.32(16) . . ?
C15 C13 C12 112.03(14) . . ?
C15 C13 C16 108.73(16) . . ?
C16 C13 C12 107.59(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 C18 110.17(15) . . ?
O2 C17 C19 101.65(13) . . ?
O2 C17 C20 109.29(15) . . ?
C18 C17 C19 110.24(16) . . ?
C20 C17 C18 113.77(18) . . ?
C20 C17 C19 111.04(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_date_sample_data_collection 2019-10-07
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.879
