#------------------------------------------------------------------------------
#$Date: 2022-02-15 01:10:09 +0200 (Tue, 15 Feb 2022) $
#$Revision: 272951 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/63/1566352.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1566352
loop_
_publ_author_name
'Bing, Jade A.'
'Schley, Nathan D.'
'Johnston, Jeffrey N.'
_publ_section_title
;
 Fluorine-induced diastereodivergence discovered in an equally rare
 enantioselective syn-aza-Henry reaction
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC05910F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H23 F N2 O4'
_chemical_formula_sum            'C17 H23 F N2 O4'
_chemical_formula_weight         338.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-26 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.1130(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.32624(13)
_cell_length_b                   15.5828(2)
_cell_length_c                   11.74267(16)
_cell_measurement_reflns_used    13960
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      72.1280
_cell_measurement_theta_min      3.9090
_cell_volume                     1815.31(4)
_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)'
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.101
_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_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_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0273
_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
_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_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc05910f2.cif
_cod_data_source_block           jab-1-299
_cod_original_cell_volume        1815.30(4)
_cod_database_code               1566352
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C17H23FN2O4
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 . . . .
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'
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
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 . . ?
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_
_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
