# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_prx-oxa
_database_code_depnum_ccdc_archive 'CCDC 1869754'
loop_
_audit_author_name
_audit_author_address
'Matheus Souza'
;IFSC
Brazil
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            PRX-OXA
_chemical_name_systematic        'Paroxetine oxalate'
_chemical_formula_moiety         'C2 O4, 2(C19 H21 F N O3), 0.5(O2H4)'
_chemical_formula_sum            'C40 H44 F2 N2 O11'
_chemical_formula_weight         766.78
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H20 N1 O7 F1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.960(3)
_cell_length_b                   6.7993(11)
_cell_length_c                   29.935(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.638(14)
_cell_angle_gamma                90
_cell_volume                     3857.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2690
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.6530
_cell_measurement_theta_min      3.0560
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            13051
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.723
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -38.00   1.00  162.50    --   27.63  54.00   0.00   27
  2  ω     19.00 118.00   1.00  162.50    --   27.63  54.00   0.00   99
  3  ω    -69.00 -43.00   1.00  162.50    --   27.63  54.00-120.00   26
  4  ω     16.00  41.00   1.00  162.50    --   27.63  54.00-120.00   25
  5  ω     30.00  57.00   1.00  162.50    --   27.63  54.00 -90.00   27
  6  ω    -69.00 116.00   1.00  162.50    --   27.63  54.00 120.00  185
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0302899000
_diffrn_orient_matrix_UB_12      -0.0124791000
_diffrn_orient_matrix_UB_13      0.0141830000
_diffrn_orient_matrix_UB_21      0.0219384000
_diffrn_orient_matrix_UB_22      0.0082573000
_diffrn_orient_matrix_UB_23      -0.0186838000
_diffrn_orient_matrix_UB_31      0.0015841000
_diffrn_orient_matrix_UB_32      0.1032268000
_diffrn_orient_matrix_UB_33      0.0034104000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          
'As it was not possible to see clear electron-density peaks in difference maps for PRX-OXA which would correspond with acceptable locations for all of the H atoms bonded to water oxygen atoms, the refinement was completed with no allowance for these water H atoms in the model.'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                3878
_reflns_number_total             7554
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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         0.286
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7554
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0774
_refine_ls_restrained_S_all      1.027
_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)+(0.1131P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2097
_refine_ls_wR_factor_ref         0.2645
_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,H) groups
2. Rigid body (RIGU) restrains
 C16B, C15B, C14B, C19B, C18B, C17B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C15A, C16A, C17A, C18A, C19A, C14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: OW1(0.5) OW2(0.5)
4.a Ternary CH refined with riding coordinates:
 C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B)
4.b Secondary CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), C1A(H1AC,H1AD), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C6A(H6AA,
 H6AB), C13A(H13A,H13B), N1B(H1BA,H1BB), C1B(H1BC,H1BD), C2B(H2BA,H2BB),
 C3B(H3BA,H3BB), C6B(H6BA,H6BB), C13B(H13C,H13D)
4.c Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C15A(H15A), C16A(H16A), C18B(H18B),
 C18A(H18A), C19A(H19A), C8B(H8B), C9B(H9B), C12B(H12B), C15B(H15B), C16B(H16B),
  C19B(H19B)
;
_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 0.3437(4) 0.1869(10) 0.65198(18) 0.0961(19) Uani 1 1 d . . . . .
O2 O 0.3269(3) 0.6761(9) 0.68171(16) 0.0735(14) Uani 1 1 d . . . . .
O3 O 0.3275(6) 0.4495(12) 0.6095(2) 0.142(3) Uani 1 1 d . . . . .
O4 O 0.3622(3) 0.4238(9) 0.72337(17) 0.0775(15) Uani 1 1 d . . . . .
O1A O 0.6531(3) 0.8703(10) 0.53428(16) 0.0776(16) Uani 1 1 d . . . . .
O2A O 0.5865(3) 0.4284(10) 0.65019(19) 0.0849(17) Uani 1 1 d . . . . .
O3A O 0.4998(3) 0.6325(12) 0.6760(2) 0.094(2) Uani 1 1 d . . . . .
N1A N 0.6982(4) 0.8723(11) 0.39704(19) 0.0776(18) Uani 1 1 d . . . . .
H1AA H 0.6835 0.7703 0.3806 0.093 Uiso 1 1 calc R . . . .
H1AB H 0.6879 0.9817 0.3819 0.093 Uiso 1 1 calc R . . . .
C1A C 0.6610(4) 0.8737(16) 0.4396(3) 0.083(2) Uani 1 1 d . . . . .
H1AC H 0.6708 0.7517 0.4554 0.100 Uiso 1 1 calc R . . . .
H1AD H 0.6106 0.8799 0.4333 0.100 Uiso 1 1 calc R . . . .
C2A C 0.7749(5) 0.8591(17) 0.4047(3) 0.090(3) Uani 1 1 d . . . . .
H2AA H 0.7984 0.8644 0.3764 0.108 Uiso 1 1 calc R . . . .
H2AB H 0.7868 0.7351 0.4191 0.108 Uiso 1 1 calc R . . . .
C3A C 0.7993(4) 1.0263(18) 0.4338(3) 0.092(3) Uani 1 1 d . . . . .
H3AA H 0.7902 1.1491 0.4181 0.110 Uiso 1 1 calc R . . . .
H3AB H 0.8498 1.0155 0.4391 0.110 Uiso 1 1 calc R . . . .
C4A C 0.7625(4) 1.0315(14) 0.4790(2) 0.070(2) Uani 1 1 d . . . . .
H4A H 0.7722 0.9066 0.4943 0.084 Uiso 1 1 calc R . . . .
C5A C 0.6822(3) 1.0430(13) 0.4690(2) 0.0637(18) Uani 1 1 d . . . . .
H5A H 0.6726 1.1648 0.4524 0.076 Uiso 1 1 calc R . . . .
C6A C 0.6375(4) 1.0434(14) 0.5099(2) 0.072(2) Uani 1 1 d . . . . .
H6AA H 0.6481 1.1583 0.5281 0.086 Uiso 1 1 calc R . . . .
H6AB H 0.5878 1.0466 0.5012 0.086 Uiso 1 1 calc R . . . .
C7A C 0.6103(3) 0.8252(13) 0.5695(2) 0.066(2) Uani 1 1 d . . . . .
C8A C 0.5587(4) 0.9480(14) 0.5840(2) 0.070(2) Uani 1 1 d . . . . .
H8A H 0.5507 1.0678 0.5698 0.085 Uiso 1 1 calc R . . . .
C9A C 0.5173(4) 0.8942(15) 0.6205(3) 0.074(2) Uani 1 1 d . . . . .
H9A H 0.4828 0.9775 0.6313 0.089 Uiso 1 1 calc R . . . .
C10A C 0.5303(4) 0.7128(15) 0.6394(2) 0.072(2) Uani 1 1 d . . . . .
C11A C 0.5826(3) 0.5944(13) 0.6241(2) 0.0653(18) Uani 1 1 d . . . . .
C12A C 0.6239(3) 0.6443(14) 0.5895(2) 0.067(2) Uani 1 1 d . . . . .
H12A H 0.6593 0.5616 0.5797 0.080 Uiso 1 1 calc R . . . .
C13A C 0.5281(5) 0.4446(19) 0.6791(3) 0.102(3) Uani 1 1 d . . . . .
H13A H 0.4924 0.3483 0.6707 0.122 Uiso 1 1 calc R . . . .
H13B H 0.5437 0.4185 0.7097 0.122 Uiso 1 1 calc R . . . .
C14A C 0.7891(4) 1.1962(15) 0.5092(2) 0.075(2) Uani 1 1 d . U . . .
C15A C 0.8087(7) 1.3768(17) 0.4930(3) 0.112(3) Uani 1 1 d . U . . .
H15A H 0.8043 1.3997 0.4624 0.134 Uiso 1 1 calc R . . . .
C16A C 0.8346(7) 1.5258(19) 0.5203(4) 0.126(4) Uani 1 1 d . U . . .
H16A H 0.8494 1.6446 0.5083 0.152 Uiso 1 1 calc R . . . .
C17A C 0.8379(6) 1.495(2) 0.5645(4) 0.109(3) Uani 1 1 d . U . . .
C18B C 0.4965(7) 0.674(3) 0.9278(4) 0.134(4) Uani 1 1 d . U . . .
H18B H 0.5105 0.7210 0.9559 0.160 Uiso 1 1 calc R . . . .
C18A C 0.8207(6) 1.319(2) 0.5817(3) 0.119(4) Uani 1 1 d . U . . .
H18A H 0.8248 1.2985 0.6124 0.143 Uiso 1 1 calc R . . . .
C19A C 0.7969(5) 1.167(2) 0.5540(3) 0.101(3) Uani 1 1 d . U . . .
H19A H 0.7862 1.0452 0.5661 0.122 Uiso 1 1 calc R . . . .
F1A F 0.8625(4) 1.6341(13) 0.5920(2) 0.158(3) Uani 1 1 d . . . . .
O1B O 0.5590(2) 1.0723(10) 0.79504(18) 0.0790(16) Uani 1 1 d . . . . .
O2B O 0.8256(3) 1.3695(12) 0.8131(2) 0.100(2) Uani 1 1 d . . . . .
O3B O 0.7313(3) 1.5710(12) 0.8255(3) 0.108(2) Uani 1 1 d . . . . .
N1B N 0.3637(3) 0.9921(10) 0.73132(18) 0.0633(15) Uani 1 1 d . . . . .
H1BA H 0.3542 0.8759 0.7189 0.076 Uiso 1 1 calc R . . . .
H1BB H 0.3508 1.0852 0.7119 0.076 Uiso 1 1 calc R . . . .
C1B C 0.4400(3) 1.0070(13) 0.7408(2) 0.0622(18) Uani 1 1 d . . . . .
H1BC H 0.4507 1.1372 0.7524 0.075 Uiso 1 1 calc R . . . .
H1BD H 0.4648 0.9911 0.7131 0.075 Uiso 1 1 calc R . . . .
C2B C 0.3223(3) 1.0138(16) 0.7725(2) 0.075(2) Uani 1 1 d . . . . .
H2BA H 0.2725 0.9972 0.7653 0.090 Uiso 1 1 calc R . . . .
H2BB H 0.3293 1.1443 0.7849 0.090 Uiso 1 1 calc R . . . .
C3B C 0.3466(4) 0.8586(18) 0.8064(2) 0.085(3) Uani 1 1 d . . . . .
H3BA H 0.3201 0.8734 0.8335 0.102 Uiso 1 1 calc R . . . .
H3BB H 0.3369 0.7287 0.7943 0.102 Uiso 1 1 calc R . . . .
C4B C 0.4251(3) 0.8769(14) 0.8178(2) 0.068(2) Uani 1 1 d . . . . .
H4B H 0.4338 1.0096 0.8295 0.081 Uiso 1 1 calc R . . . .
C5B C 0.4666(3) 0.8547(13) 0.7741(2) 0.0637(19) Uani 1 1 d . . . . .
H5B H 0.4567 0.7240 0.7617 0.076 Uiso 1 1 calc R . . . .
C6B C 0.5455(4) 0.8751(13) 0.7808(3) 0.069(2) Uani 1 1 d . . . . .
H6BA H 0.5628 0.7828 0.8033 0.082 Uiso 1 1 calc R . . . .
H6BB H 0.5690 0.8486 0.7531 0.082 Uiso 1 1 calc R . . . .
C7B C 0.6301(4) 1.1295(15) 0.7991(2) 0.071(2) Uani 1 1 d . . . . .
C8B C 0.6854(4) 1.0030(15) 0.7916(3) 0.076(2) Uani 1 1 d . . . . .
H8B H 0.6774 0.8722 0.7840 0.091 Uiso 1 1 calc R . . . .
C9B C 0.7535(4) 1.0768(16) 0.7959(3) 0.082(2) Uani 1 1 d . . . . .
H9B H 0.7919 0.9952 0.7910 0.099 Uiso 1 1 calc R . . . .
C10B C 0.7639(4) 1.2621(14) 0.8069(3) 0.069(2) Uani 1 1 d . . . . .
C11B C 0.7076(4) 1.3884(14) 0.8148(3) 0.074(2) Uani 1 1 d . . . . .
C12B C 0.6398(4) 1.3243(15) 0.8100(3) 0.076(2) Uani 1 1 d . . . . .
H12B H 0.6018 1.4084 0.8140 0.091 Uiso 1 1 calc R . . . .
C13B C 0.8064(5) 1.5589(19) 0.8263(4) 0.106(3) Uani 1 1 d . . . . .
H13C H 0.8255 1.6554 0.8061 0.127 Uiso 1 1 calc R . . . .
H13D H 0.8250 1.5856 0.8562 0.127 Uiso 1 1 calc R . . . .
C14B C 0.4503(4) 0.7304(19) 0.8532(3) 0.085(2) Uani 1 1 d . U . . .
C15B C 0.4508(6) 0.535(2) 0.8468(3) 0.105(3) Uani 1 1 d . U . . .
H15B H 0.4342 0.4838 0.8197 0.126 Uiso 1 1 calc R . . . .
C16B C 0.4750(7) 0.412(3) 0.8792(4) 0.140(4) Uani 1 1 d . U . . .
H16B H 0.4756 0.2772 0.8738 0.168 Uiso 1 1 calc R . . . .
C17B C 0.4981(6) 0.481(3) 0.9186(4) 0.120(4) Uani 1 1 d . U . . .
C19B C 0.4737(5) 0.802(2) 0.8946(3) 0.109(3) Uani 1 1 d . U . . .
H19B H 0.4741 0.9367 0.8999 0.131 Uiso 1 1 calc R . . . .
F1B F 0.5195(5) 0.3553(18) 0.9508(2) 0.205(5) Uani 1 1 d . . . . .
OW1 O 0.4722(6) 0.488(2) 0.5166(4) 0.094(4) Uani 0.5 1 d . . P . .
OW2 O 0.4616(7) 0.353(2) 0.5489(5) 0.107(4) Uani 0.5 1 d . . P . .
C20 C 0.3371(4) 0.3623(13) 0.6461(2) 0.072(2) Uani 1 1 d . . . . .
C21 C 0.3438(3) 0.4995(14) 0.6872(2) 0.0648(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.212(11) . ?
O2 C21 1.252(10) . ?
O3 C20 1.253(10) . ?
O4 C21 1.241(9) . ?
O1A C6A 1.411(10) . ?
O1A C7A 1.383(8) . ?
O2A C11A 1.373(10) . ?
O2A C13A 1.429(10) . ?
O3A C10A 1.367(9) . ?
O3A C13A 1.388(13) . ?
N1A H1AA 0.8900 . ?
N1A H1AB 0.8900 . ?
N1A C1A 1.473(9) . ?
N1A C2A 1.468(10) . ?
C1A H1AC 0.9700 . ?
C1A H1AD 0.9700 . ?
C1A C5A 1.497(12) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.497(12) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C4A 1.541(9) . ?
C4A H4A 0.9800 . ?
C4A C5A 1.545(9) . ?
C4A C14A 1.517(12) . ?
C5A H5A 0.9800 . ?
C5A C6A 1.511(9) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C7A C8A 1.368(10) . ?
C7A C12A 1.389(11) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.412(10) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.376(13) . ?
C10A C11A 1.367(11) . ?
C11A C12A 1.360(9) . ?
C12A H12A 0.9300 . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.375(15) . ?
C14A C19A 1.358(11) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.384(14) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.339(15) . ?
C17A C18A 1.346(17) . ?
C17A F1A 1.331(12) . ?
C18B H18B 0.9300 . ?
C18B C17B 1.35(2) . ?
C18B C19B 1.380(17) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.392(16) . ?
C19A H19A 0.9300 . ?
O1B C6B 1.428(10) . ?
O1B C7B 1.404(9) . ?
O2B C10B 1.387(10) . ?
O2B C13B 1.398(14) . ?
O3B C11B 1.356(12) . ?
O3B C13B 1.425(11) . ?
N1B H1BA 0.8900 . ?
N1B H1BB 0.8900 . ?
N1B C1B 1.469(8) . ?
N1B C2B 1.487(8) . ?
C1B H1BC 0.9700 . ?
C1B H1BD 0.9700 . ?
C1B C5B 1.515(10) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2B C3B 1.527(12) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C3B C4B 1.523(9) . ?
C4B H4B 0.9800 . ?
C4B C5B 1.552(8) . ?
C4B C14B 1.522(12) . ?
C5B H5B 0.9800 . ?
C5B C6B 1.509(9) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C7B C8B 1.380(11) . ?
C7B C12B 1.376(13) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.388(11) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.316(13) . ?
C10B C11B 1.394(12) . ?
C11B C12B 1.361(11) . ?
C12B H12B 0.9300 . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.341(16) . ?
C14B C19B 1.391(13) . ?
C15B H15B 0.9300 . ?
C15B C16B 1.351(16) . ?
C16B H16B 0.9300 . ?
C16B C17B 1.332(19) . ?
C17B F1B 1.340(13) . ?
C19B H19B 0.9300 . ?
OW1 OW1 1.47(2) 2_656 ?
OW1 OW2 1.353(17) . ?
C20 C21 1.547(11) . ?

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
C7A O1A C6A 117.3(6) . . ?
C11A O2A C13A 104.5(7) . . ?
C10A O3A C13A 104.4(7) . . ?
H1AA N1A H1AB 108.0 . . ?
C1A N1A H1AA 109.4 . . ?
C1A N1A H1AB 109.4 . . ?
C2A N1A H1AA 109.4 . . ?
C2A N1A H1AB 109.4 . . ?
C2A N1A C1A 111.2(6) . . ?
N1A C1A H1AC 109.1 . . ?
N1A C1A H1AD 109.1 . . ?
N1A C1A C5A 112.7(7) . . ?
H1AC C1A H1AD 107.8 . . ?
C5A C1A H1AC 109.1 . . ?
C5A C1A H1AD 109.1 . . ?
N1A C2A H2AA 109.8 . . ?
N1A C2A H2AB 109.8 . . ?
N1A C2A C3A 109.4(8) . . ?
H2AA C2A H2AB 108.2 . . ?
C3A C2A H2AA 109.8 . . ?
C3A C2A H2AB 109.8 . . ?
C2A C3A H3AA 109.0 . . ?
C2A C3A H3AB 109.0 . . ?
C2A C3A C4A 112.8(7) . . ?
H3AA C3A H3AB 107.8 . . ?
C4A C3A H3AA 109.0 . . ?
C4A C3A H3AB 109.0 . . ?
C3A C4A H4A 107.8 . . ?
C3A C4A C5A 107.4(6) . . ?
C5A C4A H4A 107.8 . . ?
C14A C4A C3A 112.9(7) . . ?
C14A C4A H4A 107.8 . . ?
C14A C4A C5A 112.8(6) . . ?
C1A C5A C4A 108.8(6) . . ?
C1A C5A H5A 108.0 . . ?
C1A C5A C6A 109.3(7) . . ?
C4A C5A H5A 108.0 . . ?
C6A C5A C4A 114.5(6) . . ?
C6A C5A H5A 108.0 . . ?
O1A C6A C5A 107.7(6) . . ?
O1A C6A H6AA 110.2 . . ?
O1A C6A H6AB 110.2 . . ?
C5A C6A H6AA 110.2 . . ?
C5A C6A H6AB 110.2 . . ?
H6AA C6A H6AB 108.5 . . ?
O1A C7A C12A 114.8(6) . . ?
C8A C7A O1A 123.3(8) . . ?
C8A C7A C12A 121.9(6) . . ?
C7A C8A H8A 119.8 . . ?
C7A C8A C9A 120.5(8) . . ?
C9A C8A H8A 119.8 . . ?
C8A C9A H9A 121.5 . . ?
C10A C9A C8A 117.0(7) . . ?
C10A C9A H9A 121.5 . . ?
O3A C10A C9A 127.8(7) . . ?
O3A C10A C11A 111.2(8) . . ?
C11A C10A C9A 120.9(7) . . ?
C10A C11A O2A 108.7(6) . . ?
C12A C11A O2A 128.0(7) . . ?
C12A C11A C10A 123.2(8) . . ?
C7A C12A H12A 121.8 . . ?
C11A C12A C7A 116.5(7) . . ?
C11A C12A H12A 121.8 . . ?
O2A C13A H13A 109.8 . . ?
O2A C13A H13B 109.8 . . ?
O3A C13A O2A 109.6(8) . . ?
O3A C13A H13A 109.8 . . ?
O3A C13A H13B 109.8 . . ?
H13A C13A H13B 108.2 . . ?
C15A C14A C4A 122.5(7) . . ?
C19A C14A C4A 120.4(10) . . ?
C19A C14A C15A 117.1(10) . . ?
C14A C15A H15A 118.6 . . ?
C14A C15A C16A 122.7(9) . . ?
C16A C15A H15A 118.6 . . ?
C15A C16A H16A 120.8 . . ?
C17A C16A C15A 118.3(12) . . ?
C17A C16A H16A 120.8 . . ?
C16A C17A C18A 120.8(11) . . ?
F1A C17A C16A 120.3(12) . . ?
F1A C17A C18A 118.8(10) . . ?
C17B C18B H18B 120.8 . . ?
C17B C18B C19B 118.5(13) . . ?
C19B C18B H18B 120.8 . . ?
C17A C18A H18A 119.7 . . ?
C17A C18A C19A 120.6(10) . . ?
C19A C18A H18A 119.7 . . ?
C14A C19A C18A 120.3(11) . . ?
C14A C19A H19A 119.8 . . ?
C18A C19A H19A 119.8 . . ?
C7B O1B C6B 116.7(6) . . ?
C10B O2B C13B 107.3(7) . . ?
C11B O3B C13B 105.9(8) . . ?
H1BA N1B H1BB 107.9 . . ?
C1B N1B H1BA 109.2 . . ?
C1B N1B H1BB 109.2 . . ?
C1B N1B C2B 112.0(5) . . ?
C2B N1B H1BA 109.2 . . ?
C2B N1B H1BB 109.2 . . ?
N1B C1B H1BC 109.0 . . ?
N1B C1B H1BD 109.0 . . ?
N1B C1B C5B 112.8(6) . . ?
H1BC C1B H1BD 107.8 . . ?
C5B C1B H1BC 109.0 . . ?
C5B C1B H1BD 109.0 . . ?
N1B C2B H2BA 109.9 . . ?
N1B C2B H2BB 109.9 . . ?
N1B C2B C3B 109.0(6) . . ?
H2BA C2B H2BB 108.3 . . ?
C3B C2B H2BA 109.9 . . ?
C3B C2B H2BB 109.9 . . ?
C2B C3B H3BA 109.3 . . ?
C2B C3B H3BB 109.3 . . ?
H3BA C3B H3BB 108.0 . . ?
C4B C3B C2B 111.5(7) . . ?
C4B C3B H3BA 109.3 . . ?
C4B C3B H3BB 109.3 . . ?
C3B C4B H4B 107.9 . . ?
C3B C4B C5B 108.6(5) . . ?
C5B C4B H4B 107.9 . . ?
C14B C4B C3B 112.8(7) . . ?
C14B C4B H4B 107.9 . . ?
C14B C4B C5B 111.6(6) . . ?
C1B C5B C4B 108.7(6) . . ?
C1B C5B H5B 108.2 . . ?
C4B C5B H5B 108.2 . . ?
C6B C5B C1B 109.6(6) . . ?
C6B C5B C4B 113.8(6) . . ?
C6B C5B H5B 108.2 . . ?
O1B C6B C5B 107.2(6) . . ?
O1B C6B H6BA 110.3 . . ?
O1B C6B H6BB 110.3 . . ?
C5B C6B H6BA 110.3 . . ?
C5B C6B H6BB 110.3 . . ?
H6BA C6B H6BB 108.5 . . ?
C8B C7B O1B 123.1(8) . . ?
C12B C7B O1B 114.1(7) . . ?
C12B C7B C8B 122.8(7) . . ?
C7B C8B H8B 121.0 . . ?
C7B C8B C9B 118.0(9) . . ?
C9B C8B H8B 121.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.1(9) . . ?
C10B C9B H9B 120.0 . . ?
O2B C10B C11B 107.5(8) . . ?
C9B C10B O2B 131.0(8) . . ?
C9B C10B C11B 121.5(8) . . ?
O3B C11B C10B 110.7(7) . . ?
O3B C11B C12B 128.5(9) . . ?
C12B C11B C10B 120.7(9) . . ?
C7B C12B H12B 121.6 . . ?
C11B C12B C7B 116.9(8) . . ?
C11B C12B H12B 121.6 . . ?
O2B C13B O3B 108.5(8) . . ?
O2B C13B H13C 110.0 . . ?
O2B C13B H13D 110.0 . . ?
O3B C13B H13C 110.0 . . ?
O3B C13B H13D 110.0 . . ?
H13C C13B H13D 108.4 . . ?
C15B C14B C4B 123.5(9) . . ?
C15B C14B C19B 118.0(10) . . ?
C19B C14B C4B 118.5(11) . . ?
C14B C15B H15B 119.5 . . ?
C14B C15B C16B 121.0(12) . . ?
C16B C15B H15B 119.5 . . ?
C15B C16B H16B 119.5 . . ?
C17B C16B C15B 120.9(16) . . ?
C17B C16B H16B 119.5 . . ?
C16B C17B C18B 121.0(13) . . ?
C16B C17B F1B 119.9(16) . . ?
F1B C17B C18B 119.0(13) . . ?
C18B C19B C14B 120.5(14) . . ?
C18B C19B H19B 119.8 . . ?
C14B C19B H19B 119.8 . . ?
OW2 OW1 OW1 127.4(10) . 2_656 ?
O1 C20 O3 127.2(8) . . ?
O1 C20 C21 118.1(7) . . ?
O3 C20 C21 114.6(8) . . ?
O2 C21 C20 117.3(6) . . ?
O4 C21 O2 125.2(8) . . ?
O4 C21 C20 117.4(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C20 C21 O2 -170.0(8) . . . . ?
O1 C20 C21 O4 6.5(11) . . . . ?
O3 C20 C21 O2 12.3(11) . . . . ?
O3 C20 C21 O4 -171.1(8) . . . . ?
O1A C7A C8A C9A -179.2(7) . . . . ?
O1A C7A C12A C11A -179.7(7) . . . . ?
O2A C11A C12A C7A -177.8(7) . . . . ?
O3A C10A C11A O2A 1.4(9) . . . . ?
O3A C10A C11A C12A -176.5(7) . . . . ?
N1A C1A C5A C4A -59.0(9) . . . . ?
N1A C1A C5A C6A 175.3(7) . . . . ?
N1A C2A C3A C4A 57.7(11) . . . . ?
C1A N1A C2A C3A -56.9(10) . . . . ?
C1A C5A C6A O1A 64.3(8) . . . . ?
C2A N1A C1A C5A 59.8(10) . . . . ?
C2A C3A C4A C5A -57.2(11) . . . . ?
C2A C3A C4A C14A 177.8(8) . . . . ?
C3A C4A C5A C1A 55.7(9) . . . . ?
C3A C4A C5A C6A 178.3(8) . . . . ?
C3A C4A C14A C15A 35.5(12) . . . . ?
C3A C4A C14A C19A -142.1(9) . . . . ?
C4A C5A C6A O1A -58.0(10) . . . . ?
C4A C14A C15A C16A -178.4(10) . . . . ?
C4A C14A C19A C18A -179.5(9) . . . . ?
C5A C4A C14A C15A -86.5(10) . . . . ?
C5A C4A C14A C19A 95.9(9) . . . . ?
C6A O1A C7A C8A -6.2(11) . . . . ?
C6A O1A C7A C12A 174.1(7) . . . . ?
C7A O1A C6A C5A -170.2(6) . . . . ?
C7A C8A C9A C10A -1.7(12) . . . . ?
C8A C7A C12A C11A 0.6(11) . . . . ?
C8A C9A C10A O3A 176.6(7) . . . . ?
C8A C9A C10A C11A 2.0(12) . . . . ?
C9A C10A C11A O2A 176.9(7) . . . . ?
C9A C10A C11A C12A -1.1(12) . . . . ?
C10A O3A C13A O2A 12.3(11) . . . . ?
C10A C11A C12A C7A -0.3(11) . . . . ?
C11A O2A C13A O3A -11.6(11) . . . . ?
C12A C7A C8A C9A 0.4(12) . . . . ?
C13A O2A C11A C10A 6.1(9) . . . . ?
C13A O2A C11A C12A -176.0(9) . . . . ?
C13A O3A C10A C9A 176.4(9) . . . . ?
C13A O3A C10A C11A -8.5(10) . . . . ?
C14A C4A C5A C1A -179.2(7) . . . . ?
C14A C4A C5A C6A -56.6(10) . . . . ?
C14A C15A C16A C17A -3(2) . . . . ?
C15A C14A C19A C18A 2.9(15) . . . . ?
C15A C16A C17A C18A 4(2) . . . . ?
C15A C16A C17A F1A 179.9(11) . . . . ?
C16A C17A C18A C19A -2(2) . . . . ?
C17A C18A C19A C14A -1.6(18) . . . . ?
C19A C14A C15A C16A -0.7(17) . . . . ?
F1A C17A C18A C19A -177.9(11) . . . . ?
O1B C7B C8B C9B 179.0(7) . . . . ?
O1B C7B C12B C11B 179.5(6) . . . . ?
O2B C10B C11B O3B 0.1(9) . . . . ?
O2B C10B C11B C12B 178.3(7) . . . . ?
O3B C11B C12B C7B -179.6(8) . . . . ?
N1B C1B C5B C4B -57.0(8) . . . . ?
N1B C1B C5B C6B 178.1(6) . . . . ?
N1B C2B C3B C4B 58.2(9) . . . . ?
C1B N1B C2B C3B -56.9(9) . . . . ?
C1B C5B C6B O1B 57.0(8) . . . . ?
C2B N1B C1B C5B 58.3(9) . . . . ?
C2B C3B C4B C5B -58.5(10) . . . . ?
C2B C3B C4B C14B 177.3(8) . . . . ?
C3B C4B C5B C1B 56.2(9) . . . . ?
C3B C4B C5B C6B 178.6(8) . . . . ?
C3B C4B C14B C15B 65.8(11) . . . . ?
C3B C4B C14B C19B -113.9(9) . . . . ?
C4B C5B C6B O1B -64.9(8) . . . . ?
C4B C14B C15B C16B 178.7(9) . . . . ?
C4B C14B C19B C18B 179.5(9) . . . . ?
C5B C4B C14B C15B -56.8(11) . . . . ?
C5B C4B C14B C19B 123.5(8) . . . . ?
C6B O1B C7B C8B -2.5(10) . . . . ?
C6B O1B C7B C12B 176.0(7) . . . . ?
C7B O1B C6B C5B -174.0(5) . . . . ?
C7B C8B C9B C10B 0.3(13) . . . . ?
C8B C7B C12B C11B -2.0(12) . . . . ?
C8B C9B C10B O2B -179.8(8) . . . . ?
C8B C9B C10B C11B 0.2(13) . . . . ?
C9B C10B C11B O3B -179.9(8) . . . . ?
C9B C10B C11B C12B -1.7(12) . . . . ?
C10B O2B C13B O3B -3.6(11) . . . . ?
C10B C11B C12B C7B 2.5(12) . . . . ?
C11B O3B C13B O2B 3.6(11) . . . . ?
C12B C7B C8B C9B 0.6(12) . . . . ?
C13B O2B C10B C9B -177.8(10) . . . . ?
C13B O2B C10B C11B 2.1(10) . . . . ?
C13B O3B C11B C10B -2.3(10) . . . . ?
C13B O3B C11B C12B 179.7(9) . . . . ?
C14B C4B C5B C1B -178.9(7) . . . . ?
C14B C4B C5B C6B -56.5(10) . . . . ?
C14B C15B C16B C17B 1.0(19) . . . . ?
C15B C14B C19B C18B -0.2(15) . . . . ?
C15B C16B C17B C18B 1(2) . . . . ?
C15B C16B C17B F1B 177.6(11) . . . . ?
C17B C18B C19B C14B 2.5(18) . . . . ?
C19B C18B C17B C16B -3(2) . . . . ?
C19B C18B C17B F1B -179.4(10) . . . . ?
C19B C14B C15B C16B -1.6(16) . . . . ?

_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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.826
####################################################################### 
# 
# 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_prx-fum
_database_code_depnum_ccdc_archive 'CCDC 1869771'
loop_
_audit_author_name
_audit_author_address
'Matheus Souza'
;IFSC
Brazil
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            PRX-FUM
_chemical_name_systematic        'Paroxetine fumarate'
_chemical_formula_moiety         'C19 H21 F N O3, C4 H3 O4'
_chemical_formula_sum            'C23 H24 F N O7'
_chemical_formula_weight         445.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2223(3)
_cell_length_b                   7.9950(10)
_cell_length_c                   18.538(2)
_cell_angle_alpha                78.672(10)
_cell_angle_beta                 82.396(5)
_cell_angle_gamma                85.860(7)
_cell_volume                     1039.16(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    38820
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.242
_cell_measurement_theta_min      2.849
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.98361
_exptl_absorpt_correction_T_min  0.96640
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'P. Coppens in Crystallographic Computing ed F.R. Ahmed, S.R. Hall and C.P. Huber, Copenhagen, Munksgaard, (1970) pp 255-270'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38812
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.098
_diffrn_reflns_theta_min         2.849
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                14521
_reflns_number_total             15464
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.398
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 6742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         15464
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.048
_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)+(0.0612P)²+0.1507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1061
_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,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B)
2.b Secondary CH2 refined with riding coordinates:
 N1A(H1Aa,H1Ab), C1A(H1Ac,H1Ad), C2A(H2Aa,H2Ab), C3A(H3Aa,H3Ab), C6A(H6Aa,
 H6Ab), C13A(H13a,H13b), N1B(H1Ba,H1Bb), C1B(H1Bc,H1Bd), C2B(H2Ba,H2Bb),
 C3B(H3Ba,H3Bb), C6B(H6Ba,H6Bb), C13B(H13c,H13d)
2.c Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C15A(H15A), C16A(H16A), C18A(H18A),
 C19A(H19A), C21A(H21A), C22A(H22A), C8B(H8B), C9B(H9B), C12B(H12B), C15B(H15B),
  C16B(H16B), C18B(H18B), C19B(H19B), C21B(H21B), C22B(H22B)
2.d Idealised tetrahedral OH refined as rotating group:
 O6A(H6A), O6B(H6B)
;
_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
O1A O 0.9247(2) 0.4848(2) 0.71885(10) 0.0346(4) Uani 1 1 d . . . . .
O2A O 1.1945(2) 0.0849(3) 0.96003(8) 0.0355(4) Uani 1 1 d . . . . .
O3A O 1.4012(2) 0.2174(2) 0.86248(10) 0.0361(4) Uani 1 1 d . . . . .
O4A O 0.48399(16) 0.05891(15) 0.60121(8) 0.0185(2) Uani 1 1 d . . . . .
O5A O 0.24117(16) -0.00819(14) 0.55155(7) 0.0152(2) Uani 1 1 d . . . . .
O7A O 0.18125(16) 0.63508(14) 0.50992(7) 0.0163(2) Uani 1 1 d . . . . .
O6A O 0.36400(17) 0.68368(14) 0.59138(7) 0.0181(2) Uani 1 1 d . . . . .
H6A H 0.3320 0.7861 0.5756 0.027 Uiso 1 1 calc GR . . . .
N1A N 0.86111(19) 0.98191(18) 0.60844(8) 0.0162(2) Uani 1 1 d . . . . .
H1AA H 0.7484 1.0182 0.5926 0.019 Uiso 1 1 calc R . . . .
H1AB H 0.9521 1.0173 0.5708 0.019 Uiso 1 1 calc R . . . .
C1A C 0.8716(2) 0.79270(19) 0.62814(9) 0.0160(3) Uani 1 1 d . . . . .
H1AC H 0.9936 0.7535 0.6459 0.019 Uiso 1 1 calc R . . . .
H1AD H 0.8628 0.7444 0.5835 0.019 Uiso 1 1 calc R . . . .
C2A C 0.8849(2) 1.0577(2) 0.67349(10) 0.0206(3) Uani 1 1 d . . . . .
H2AA H 0.8814 1.1838 0.6592 0.025 Uiso 1 1 calc R . . . .
H2AB H 1.0078 1.0190 0.6906 0.025 Uiso 1 1 calc R . . . .
C3A C 0.7301(2) 1.0036(2) 0.73546(10) 0.0222(3) Uani 1 1 d . . . . .
H3AA H 0.6098 1.0568 0.7201 0.027 Uiso 1 1 calc R . . . .
H3AB H 0.7532 1.0474 0.7797 0.027 Uiso 1 1 calc R . . . .
C4A C 0.7125(2) 0.8096(2) 0.75680(9) 0.0184(3) Uani 1 1 d . . . . .
H4A H 0.8221 0.7600 0.7829 0.022 Uiso 1 1 calc R . . . .
C5A C 0.7148(2) 0.72828(19) 0.68803(9) 0.0145(2) Uani 1 1 d . . . . .
H5A H 0.5932 0.7603 0.6674 0.017 Uiso 1 1 calc R . . . .
C6A C 0.7358(2) 0.5341(2) 0.70663(11) 0.0224(3) Uani 1 1 d . . . . .
H6AA H 0.6503 0.4904 0.7517 0.027 Uiso 1 1 calc R . . . .
H6AB H 0.7027 0.4850 0.6652 0.027 Uiso 1 1 calc R . . . .
C7A C 0.9704(2) 0.3839(2) 0.78317(10) 0.0186(3) Uani 1 1 d . . . . .
C8A C 0.8454(2) 0.3065(2) 0.84083(9) 0.0180(3) Uani 1 1 d . . . . .
H8A H 0.7149 0.3245 0.8380 0.022 Uiso 1 1 calc R . . . .
C9A C 0.9092(2) 0.2015(3) 0.90356(10) 0.0230(3) Uani 1 1 d . . . . .
H9A H 0.8240 0.1474 0.9433 0.028 Uiso 1 1 calc R . . . .
C10A C 1.0982(2) 0.1799(2) 0.90537(9) 0.0209(3) Uani 1 1 d . . . . .
C11A C 1.2216(2) 0.2594(2) 0.84746(10) 0.0212(3) Uani 1 1 d . . . . .
C12A C 1.1647(2) 0.3609(2) 0.78535(11) 0.0241(3) Uani 1 1 d . . . . .
H12A H 1.2515 0.4131 0.7458 0.029 Uiso 1 1 calc R . . . .
C13A C 1.3872(3) 0.1099(3) 0.93381(12) 0.0276(4) Uani 1 1 d . . . . .
H13A H 1.4452 0.1635 0.9686 0.033 Uiso 1 1 calc R . . . .
H13B H 1.4541 -0.0015 0.9307 0.033 Uiso 1 1 calc R . . . .
C14A C 0.5367(2) 0.7688(2) 0.80959(9) 0.0194(3) Uani 1 1 d . . . . .
C15A C 0.3631(2) 0.8330(3) 0.78810(10) 0.0231(3) Uani 1 1 d . . . . .
H15A H 0.3572 0.9010 0.7402 0.028 Uiso 1 1 calc R . . . .
C16A C 0.1994(3) 0.7993(3) 0.83540(11) 0.0261(3) Uani 1 1 d . . . . .
H16A H 0.0818 0.8442 0.8208 0.031 Uiso 1 1 calc R . . . .
C17A C 0.2119(3) 0.6992(3) 0.90409(11) 0.0261(3) Uani 1 1 d . . . . .
C18A C 0.3788(3) 0.6331(3) 0.92780(11) 0.0272(4) Uani 1 1 d . . . . .
H18A H 0.3828 0.5642 0.9756 0.033 Uiso 1 1 calc R . . . .
C19A C 0.5419(3) 0.6699(3) 0.87998(10) 0.0237(3) Uani 1 1 d . . . . .
H19A H 0.6590 0.6267 0.8957 0.028 Uiso 1 1 calc R . . . .
C20A C 0.34171(19) 0.09798(17) 0.56969(8) 0.0121(2) Uani 1 1 d . . . . .
C21A C 0.2753(2) 0.28125(18) 0.55185(9) 0.0126(2) Uani 1 1 d . . . . .
H21A H 0.1749 0.3116 0.5228 0.015 Uiso 1 1 calc R . . . .
C22A C 0.3529(2) 0.40269(18) 0.57552(9) 0.0135(2) Uani 1 1 d . . . . .
H22A H 0.4508 0.3727 0.6059 0.016 Uiso 1 1 calc R . . . .
C23A C 0.2895(2) 0.58444(18) 0.55534(8) 0.0129(2) Uani 1 1 d . . . . .
F1A F 0.0506(2) 0.66480(19) 0.94992(8) 0.0376(3) Uani 1 1 d . . . . .
O1B O 0.30180(17) 0.39604(17) 0.25893(9) 0.0250(3) Uani 1 1 d . . . . .
O2B O 0.64563(19) 0.91604(18) 0.06362(8) 0.0241(3) Uani 1 1 d . . . . .
O3B O 0.80627(18) 0.75816(18) 0.15611(8) 0.0237(3) Uani 1 1 d . . . . .
O4B O 0.54044(17) 0.85774(16) 0.40843(8) 0.0216(2) Uani 1 1 d . . . . .
O5B O 0.78527(16) 0.92600(14) 0.45618(7) 0.0150(2) Uani 1 1 d . . . . .
O6B O 0.63914(16) 0.22868(14) 0.42640(7) 0.0151(2) Uani 1 1 d . . . . .
H6B H 0.6765 0.1270 0.4404 0.023 Uiso 1 1 calc GR . . . .
O7B O 0.86016(18) 0.28221(15) 0.49173(8) 0.0203(2) Uani 1 1 d . . . . .
N1B N 0.16682(18) -0.05961(16) 0.40153(7) 0.0139(2) Uani 1 1 d . . . . .
H1BA H 0.0491 -0.0694 0.4260 0.017 Uiso 1 1 calc R . . . .
H1BB H 0.2487 -0.1022 0.4347 0.017 Uiso 1 1 calc R . . . .
C1B C 0.2003(2) 0.12393(19) 0.37220(9) 0.0147(2) Uani 1 1 d . . . . .
H1BC H 0.3317 0.1360 0.3493 0.018 Uiso 1 1 calc R . . . .
H1BD H 0.1802 0.1875 0.4136 0.018 Uiso 1 1 calc R . . . .
C2B C 0.1887(2) -0.1622(2) 0.34183(9) 0.0175(3) Uani 1 1 d . . . . .
H2BA H 0.1625 -0.2827 0.3636 0.021 Uiso 1 1 calc R . . . .
H2BB H 0.3190 -0.1587 0.3172 0.021 Uiso 1 1 calc R . . . .
C3B C 0.0555(2) -0.0919(2) 0.28535(9) 0.0169(3) Uani 1 1 d . . . . .
H3BA H -0.0749 -0.1036 0.3094 0.020 Uiso 1 1 calc R . . . .
H3BB H 0.0738 -0.1591 0.2452 0.020 Uiso 1 1 calc R . . . .
C4B C 0.0876(2) 0.09658(19) 0.25214(8) 0.0144(2) Uani 1 1 d . . . . .
H4B H 0.2184 0.1045 0.2266 0.017 Uiso 1 1 calc R . . . .
C5B C 0.06985(19) 0.19998(18) 0.31483(8) 0.0132(2) Uani 1 1 d . . . . .
H5B H -0.0614 0.1930 0.3401 0.016 Uiso 1 1 calc R . . . .
C6B C 0.1079(2) 0.3875(2) 0.28668(9) 0.0166(3) Uani 1 1 d . . . . .
H6BA H 0.0301 0.4367 0.2468 0.020 Uiso 1 1 calc R . . . .
H6BB H 0.0781 0.4523 0.3274 0.020 Uiso 1 1 calc R . . . .
C7B C 0.3657(2) 0.5390(2) 0.21069(9) 0.0164(3) Uani 1 1 d . . . . .
C8B C 0.2661(2) 0.6338(2) 0.15652(9) 0.0182(3) Uani 1 1 d . . . . .
H8B H 0.1406 0.6083 0.1547 0.022 Uiso 1 1 calc R . . . .
C9B C 0.3492(2) 0.7677(2) 0.10403(9) 0.0196(3) Uani 1 1 d . . . . .
H9B H 0.2815 0.8356 0.0673 0.023 Uiso 1 1 calc R . . . .
C10B C 0.5320(2) 0.7956(2) 0.10827(9) 0.0177(3) Uani 1 1 d . . . . .
C11B C 0.6289(2) 0.7015(2) 0.16337(9) 0.0172(3) Uani 1 1 d . . . . .
C12B C 0.5503(2) 0.5738(2) 0.21642(10) 0.0189(3) Uani 1 1 d . . . . .
H12B H 0.6169 0.5122 0.2549 0.023 Uiso 1 1 calc R . . . .
C13B C 0.8288(2) 0.8663(2) 0.08417(11) 0.0228(3) Uani 1 1 d . . . . .
H13C H 0.8970 0.9684 0.0857 0.027 Uiso 1 1 calc R . . . .
H13D H 0.9009 0.8039 0.0477 0.027 Uiso 1 1 calc R . . . .
C14B C -0.0430(2) 0.1676(2) 0.19547(8) 0.0160(3) Uani 1 1 d . . . . .
C15B C -0.2356(2) 0.1472(2) 0.21141(10) 0.0202(3) Uani 1 1 d . . . . .
H15B H -0.2851 0.0875 0.2587 0.024 Uiso 1 1 calc R . . . .
C16B C -0.3554(3) 0.2131(3) 0.15899(11) 0.0244(3) Uani 1 1 d . . . . .
H16B H -0.4860 0.1974 0.1696 0.029 Uiso 1 1 calc R . . . .
C17B C -0.2809(3) 0.3015(2) 0.09147(11) 0.0248(3) Uani 1 1 d . . . . .
C18B C -0.0935(3) 0.3281(2) 0.07354(10) 0.0243(3) Uani 1 1 d . . . . .
H18B H -0.0464 0.3914 0.0266 0.029 Uiso 1 1 calc R . . . .
C19B C 0.0256(2) 0.2592(2) 0.12629(9) 0.0198(3) Uani 1 1 d . . . . .
H19B H 0.1560 0.2750 0.1149 0.024 Uiso 1 1 calc R . . . .
C20B C 0.68428(19) 0.81862(18) 0.43808(8) 0.0127(2) Uani 1 1 d . . . . .
C21B C 0.7536(2) 0.63546(18) 0.45448(9) 0.0133(2) Uani 1 1 d . . . . .
H21B H 0.8635 0.6068 0.4782 0.016 Uiso 1 1 calc R . . . .
C22B C 0.6650(2) 0.51216(18) 0.43661(9) 0.0135(2) Uani 1 1 d . . . . .
H22B H 0.5569 0.5408 0.4117 0.016 Uiso 1 1 calc R . . . .
C23B C 0.7318(2) 0.33037(18) 0.45486(8) 0.0131(2) Uani 1 1 d . . . . .
F1B F -0.3984(2) 0.3651(2) 0.04022(8) 0.0381(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C6A 1.427(2) . ?
O1A C7A 1.367(2) . ?
O2A C10A 1.377(2) . ?
O2A C13A 1.427(2) . ?
O3A C11A 1.366(2) . ?
O3A C13A 1.424(3) . ?
O4A C20A 1.2392(17) . ?
O5A C20A 1.2755(17) . ?
O7A C23A 1.2158(18) . ?
O6A H6A 0.8400 . ?
O6A C23A 1.3156(17) . ?
N1A H1AA 0.9100 . ?
N1A H1AB 0.9100 . ?
N1A C1A 1.484(2) . ?
N1A C2A 1.486(2) . ?
C1A H1AC 0.9900 . ?
C1A H1AD 0.9900 . ?
C1A C5A 1.519(2) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.514(2) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.533(3) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.539(2) . ?
C4A C14A 1.510(2) . ?
C5A H5A 1.0000 . ?
C5A C6A 1.524(2) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C8A 1.380(2) . ?
C7A C12A 1.407(2) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.404(2) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.368(2) . ?
C10A C11A 1.383(2) . ?
C11A C12A 1.365(3) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.398(2) . ?
C14A C19A 1.390(2) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.385(2) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.375(3) . ?
C17A C18A 1.372(3) . ?
C17A F1A 1.359(2) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.390(3) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.495(2) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.3266(19) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.482(2) . ?
O1B C6B 1.4283(19) . ?
O1B C7B 1.3730(19) . ?
O2B C10B 1.381(2) . ?
O2B C13B 1.432(2) . ?
O3B C11B 1.3706(19) . ?
O3B C13B 1.436(2) . ?
O4B C20B 1.2312(18) . ?
O5B C20B 1.2845(17) . ?
O6B H6B 0.8400 . ?
O6B C23B 1.3142(17) . ?
O7B C23B 1.2199(18) . ?
N1B H1BA 0.9100 . ?
N1B H1BB 0.9100 . ?
N1B C1B 1.487(2) . ?
N1B C2B 1.488(2) . ?
C1B H1BC 0.9900 . ?
C1B H1BD 0.9900 . ?
C1B C5B 1.522(2) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.515(2) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.534(2) . ?
C4B H4B 1.0000 . ?
C4B C5B 1.540(2) . ?
C4B C14B 1.505(2) . ?
C5B H5B 1.0000 . ?
C5B C6B 1.520(2) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.383(2) . ?
C7B C12B 1.403(2) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.408(2) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.370(2) . ?
C10B C11B 1.382(2) . ?
C11B C12B 1.369(2) . ?
C12B H12B 0.9500 . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.398(2) . ?
C14B C19B 1.393(2) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.388(2) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.373(3) . ?
C17B C18B 1.372(3) . ?
C17B F1B 1.357(2) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.393(2) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.499(2) . ?
C21B H21B 0.9500 . ?
C21B C22B 1.3293(19) . ?
C22B H22B 0.9500 . ?
C22B C23B 1.486(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A O1A C6A 122.46(15) . . ?
C10A O2A C13A 105.10(15) . . ?
C11A O3A C13A 106.00(15) . . ?
C23A O6A H6A 109.5 . . ?
H1AA N1A H1AB 108.1 . . ?
C1A N1A H1AA 109.5 . . ?
C1A N1A H1AB 109.5 . . ?
C1A N1A C2A 110.53(13) . . ?
C2A N1A H1AA 109.5 . . ?
C2A N1A H1AB 109.5 . . ?
N1A C1A H1AC 109.4 . . ?
N1A C1A H1AD 109.4 . . ?
N1A C1A C5A 111.05(12) . . ?
H1AC C1A H1AD 108.0 . . ?
C5A C1A H1AC 109.4 . . ?
C5A C1A H1AD 109.4 . . ?
N1A C2A H2AA 109.7 . . ?
N1A C2A H2AB 109.7 . . ?
N1A C2A C3A 109.70(13) . . ?
H2AA C2A H2AB 108.2 . . ?
C3A C2A H2AA 109.7 . . ?
C3A C2A H2AB 109.7 . . ?
C2A C3A H3AA 108.8 . . ?
C2A C3A H3AB 108.8 . . ?
C2A C3A C4A 113.75(14) . . ?
H3AA C3A H3AB 107.7 . . ?
C4A C3A H3AA 108.8 . . ?
C4A C3A H3AB 108.8 . . ?
C3A C4A H4A 108.1 . . ?
C3A C4A C5A 111.55(13) . . ?
C5A C4A H4A 108.1 . . ?
C14A C4A C3A 110.04(14) . . ?
C14A C4A H4A 108.1 . . ?
C14A C4A C5A 110.77(13) . . ?
C1A C5A C4A 111.75(12) . . ?
C1A C5A H5A 108.1 . . ?
C1A C5A C6A 108.36(13) . . ?
C4A C5A H5A 108.1 . . ?
C6A C5A C4A 112.15(14) . . ?
C6A C5A H5A 108.1 . . ?
O1A C6A C5A 109.10(15) . . ?
O1A C6A H6AA 109.9 . . ?
O1A C6A H6AB 109.9 . . ?
C5A C6A H6AA 109.9 . . ?
C5A C6A H6AB 109.9 . . ?
H6AA C6A H6AB 108.3 . . ?
O1A C7A C8A 125.75(15) . . ?
O1A C7A C12A 112.89(15) . . ?
C8A C7A C12A 121.35(16) . . ?
C7A C8A H8A 119.7 . . ?
C7A C8A C9A 120.70(15) . . ?
C9A C8A H8A 119.7 . . ?
C8A C9A H9A 121.2 . . ?
C10A C9A C8A 117.65(16) . . ?
C10A C9A H9A 121.2 . . ?
O2A C10A C11A 110.26(15) . . ?
C9A C10A O2A 128.74(17) . . ?
C9A C10A C11A 121.00(16) . . ?
O3A C11A C10A 109.69(16) . . ?
C12A C11A O3A 127.38(17) . . ?
C12A C11A C10A 122.92(16) . . ?
C7A C12A H12A 121.8 . . ?
C11A C12A C7A 116.38(16) . . ?
C11A C12A H12A 121.8 . . ?
O2A C13A H13A 109.9 . . ?
O2A C13A H13B 109.9 . . ?
O3A C13A O2A 108.92(14) . . ?
O3A C13A H13A 109.9 . . ?
O3A C13A H13B 109.9 . . ?
H13A C13A H13B 108.3 . . ?
C15A C14A C4A 119.68(15) . . ?
C19A C14A C4A 121.89(15) . . ?
C19A C14A C15A 118.43(16) . . ?
C14A C15A H15A 119.4 . . ?
C16A C15A C14A 121.15(17) . . ?
C16A C15A H15A 119.4 . . ?
C15A C16A H16A 120.9 . . ?
C17A C16A C15A 118.16(18) . . ?
C17A C16A H16A 120.9 . . ?
C18A C17A C16A 122.92(17) . . ?
F1A C17A C16A 117.88(19) . . ?
F1A C17A C18A 119.19(18) . . ?
C17A C18A H18A 120.9 . . ?
C17A C18A C19A 118.18(17) . . ?
C19A C18A H18A 120.9 . . ?
C14A C19A H19A 119.4 . . ?
C18A C19A C14A 121.15(17) . . ?
C18A C19A H19A 119.4 . . ?
O4A C20A O5A 124.83(13) . . ?
O4A C20A C21A 119.68(13) . . ?
O5A C20A C21A 115.48(12) . . ?
C20A C21A H21A 119.1 . . ?
C22A C21A C20A 121.80(13) . . ?
C22A C21A H21A 119.1 . . ?
C21A C22A H22A 119.4 . . ?
C21A C22A C23A 121.11(13) . . ?
C23A C22A H22A 119.4 . . ?
O7A C23A O6A 124.16(13) . . ?
O7A C23A C22A 123.16(13) . . ?
O6A C23A C22A 112.67(13) . . ?
C7B O1B C6B 119.90(13) . . ?
C10B O2B C13B 104.32(13) . . ?
C11B O3B C13B 104.55(13) . . ?
C23B O6B H6B 109.5 . . ?
H1BA N1B H1BB 107.9 . . ?
C1B N1B H1BA 109.1 . . ?
C1B N1B H1BB 109.1 . . ?
C1B N1B C2B 112.30(12) . . ?
C2B N1B H1BA 109.1 . . ?
C2B N1B H1BB 109.1 . . ?
N1B C1B H1BC 109.4 . . ?
N1B C1B H1BD 109.4 . . ?
N1B C1B C5B 111.13(11) . . ?
H1BC C1B H1BD 108.0 . . ?
C5B C1B H1BC 109.4 . . ?
C5B C1B H1BD 109.4 . . ?
N1B C2B H2BA 109.6 . . ?
N1B C2B H2BB 109.6 . . ?
N1B C2B C3B 110.09(12) . . ?
H2BA C2B H2BB 108.2 . . ?
C3B C2B H2BA 109.6 . . ?
C3B C2B H2BB 109.6 . . ?
C2B C3B H3BA 109.4 . . ?
C2B C3B H3BB 109.4 . . ?
C2B C3B C4B 111.25(13) . . ?
H3BA C3B H3BB 108.0 . . ?
C4B C3B H3BA 109.4 . . ?
C4B C3B H3BB 109.4 . . ?
C3B C4B H4B 107.8 . . ?
C3B C4B C5B 109.56(12) . . ?
C5B C4B H4B 107.8 . . ?
C14B C4B C3B 111.78(12) . . ?
C14B C4B H4B 107.8 . . ?
C14B C4B C5B 111.78(12) . . ?
C1B C5B C4B 110.87(12) . . ?
C1B C5B H5B 107.8 . . ?
C4B C5B H5B 107.8 . . ?
C6B C5B C1B 109.41(12) . . ?
C6B C5B C4B 112.84(12) . . ?
C6B C5B H5B 107.8 . . ?
O1B C6B C5B 107.00(12) . . ?
O1B C6B H6BA 110.3 . . ?
O1B C6B H6BB 110.3 . . ?
C5B C6B H6BA 110.3 . . ?
C5B C6B H6BB 110.3 . . ?
H6BA C6B H6BB 108.6 . . ?
O1B C7B C8B 124.06(14) . . ?
O1B C7B C12B 113.92(14) . . ?
C8B C7B C12B 121.80(14) . . ?
C7B C8B H8B 119.7 . . ?
C7B C8B C9B 120.61(14) . . ?
C9B C8B H8B 119.7 . . ?
C8B C9B H9B 121.5 . . ?
C10B C9B C8B 117.02(15) . . ?
C10B C9B H9B 121.5 . . ?
O2B C10B C11B 109.64(14) . . ?
C9B C10B O2B 128.63(15) . . ?
C9B C10B C11B 121.70(15) . . ?
O3B C11B C10B 109.84(14) . . ?
C12B C11B O3B 127.57(15) . . ?
C12B C11B C10B 122.58(14) . . ?
C7B C12B H12B 121.9 . . ?
C11B C12B C7B 116.20(15) . . ?
C11B C12B H12B 121.9 . . ?
O2B C13B O3B 107.40(13) . . ?
O2B C13B H13C 110.2 . . ?
O2B C13B H13D 110.2 . . ?
O3B C13B H13C 110.2 . . ?
O3B C13B H13D 110.2 . . ?
H13C C13B H13D 108.5 . . ?
C15B C14B C4B 121.06(14) . . ?
C19B C14B C4B 120.48(14) . . ?
C19B C14B C15B 118.43(15) . . ?
C14B C15B H15B 119.6 . . ?
C16B C15B C14B 120.85(16) . . ?
C16B C15B H15B 119.6 . . ?
C15B C16B H16B 120.8 . . ?
C17B C16B C15B 118.48(17) . . ?
C17B C16B H16B 120.8 . . ?
C18B C17B C16B 123.00(16) . . ?
F1B C17B C16B 118.31(18) . . ?
F1B C17B C18B 118.68(18) . . ?
C17B C18B H18B 121.0 . . ?
C17B C18B C19B 117.94(17) . . ?
C19B C18B H18B 121.0 . . ?
C14B C19B C18B 121.28(16) . . ?
C14B C19B H19B 119.4 . . ?
C18B C19B H19B 119.4 . . ?
O4B C20B O5B 124.37(14) . . ?
O4B C20B C21B 120.11(13) . . ?
O5B C20B C21B 115.52(13) . . ?
C20B C21B H21B 119.2 . . ?
C22B C21B C20B 121.55(13) . . ?
C22B C21B H21B 119.2 . . ?
C21B C22B H22B 119.4 . . ?
C21B C22B C23B 121.22(13) . . ?
C23B C22B H22B 119.4 . . ?
O6B C23B C22B 112.75(12) . . ?
O7B C23B O6B 124.07(13) . . ?
O7B C23B C22B 123.17(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C7A C8A C9A 178.23(19) . . . . ?
O1A C7A C12A C11A -179.03(18) . . . . ?
O2A C10A C11A O3A 0.5(2) . . . . ?
O2A C10A C11A C12A 179.46(19) . . . . ?
O3A C11A C12A C7A 179.8(2) . . . . ?
O4A C20A C21A C22A -7.1(2) . . . . ?
O5A C20A C21A C22A 171.70(15) . . . . ?
N1A C1A C5A C4A -54.87(16) . . . . ?
N1A C1A C5A C6A -178.93(13) . . . . ?
N1A C2A C3A C4A 54.15(19) . . . . ?
C1A N1A C2A C3A -61.01(18) . . . . ?
C1A C5A C6A O1A 49.05(19) . . . . ?
C2A N1A C1A C5A 62.36(16) . . . . ?
C2A C3A C4A C5A -47.44(18) . . . . ?
C2A C3A C4A C14A -170.79(14) . . . . ?
C3A C4A C5A C1A 46.93(17) . . . . ?
C3A C4A C5A C6A 168.84(13) . . . . ?
C3A C4A C14A C15A 58.3(2) . . . . ?
C3A C4A C14A C19A -121.00(18) . . . . ?
C4A C5A C6A O1A -74.78(18) . . . . ?
C4A C14A C15A C16A -179.39(18) . . . . ?
C4A C14A C19A C18A -179.84(18) . . . . ?
C5A C4A C14A C15A -65.6(2) . . . . ?
C5A C4A C14A C19A 115.19(18) . . . . ?
C6A O1A C7A C8A 5.5(3) . . . . ?
C6A O1A C7A C12A -175.89(19) . . . . ?
C7A O1A C6A C5A 123.72(19) . . . . ?
C7A C8A C9A C10A 0.3(3) . . . . ?
C8A C7A C12A C11A -0.4(3) . . . . ?
C8A C9A C10A O2A 179.8(2) . . . . ?
C8A C9A C10A C11A 0.2(3) . . . . ?
C9A C10A C11A O3A -179.89(19) . . . . ?
C9A C10A C11A C12A -0.9(3) . . . . ?
C10A O2A C13A O3A -1.4(2) . . . . ?
C10A C11A C12A C7A 1.0(3) . . . . ?
C11A O3A C13A O2A 1.7(2) . . . . ?
C12A C7A C8A C9A -0.2(3) . . . . ?
C13A O2A C10A C9A -179.0(2) . . . . ?
C13A O2A C10A C11A 0.6(2) . . . . ?
C13A O3A C11A C10A -1.3(2) . . . . ?
C13A O3A C11A C12A 179.8(2) . . . . ?
C14A C4A C5A C1A 169.87(13) . . . . ?
C14A C4A C5A C6A -68.22(17) . . . . ?
C14A C15A C16A C17A -0.7(3) . . . . ?
C15A C14A C19A C18A 0.9(3) . . . . ?
C15A C16A C17A C18A 0.7(3) . . . . ?
C15A C16A C17A F1A -179.20(18) . . . . ?
C16A C17A C18A C19A 0.1(3) . . . . ?
C17A C18A C19A C14A -0.9(3) . . . . ?
C19A C14A C15A C16A -0.1(3) . . . . ?
C20A C21A C22A C23A 178.03(13) . . . . ?
C21A C22A C23A O7A -8.9(2) . . . . ?
C21A C22A C23A O6A 171.55(15) . . . . ?
F1A C17A C18A C19A 179.96(19) . . . . ?
O1B C7B C8B C9B -173.03(17) . . . . ?
O1B C7B C12B C11B 171.85(15) . . . . ?
O2B C10B C11B O3B 0.2(2) . . . . ?
O2B C10B C11B C12B 179.26(17) . . . . ?
O3B C11B C12B C7B -179.14(17) . . . . ?
O4B C20B C21B C22B 1.2(2) . . . . ?
O5B C20B C21B C22B -178.09(15) . . . . ?
N1B C1B C5B C4B -55.23(16) . . . . ?
N1B C1B C5B C6B 179.68(12) . . . . ?
N1B C2B C3B C4B 57.46(17) . . . . ?
C1B N1B C2B C3B -58.01(17) . . . . ?
C1B C5B C6B O1B 56.10(17) . . . . ?
C2B N1B C1B C5B 57.27(16) . . . . ?
C2B C3B C4B C5B -55.98(16) . . . . ?
C2B C3B C4B C14B 179.55(13) . . . . ?
C3B C4B C5B C1B 54.45(15) . . . . ?
C3B C4B C5B C6B 177.58(12) . . . . ?
C3B C4B C14B C15B 50.5(2) . . . . ?
C3B C4B C14B C19B -131.07(16) . . . . ?
C4B C5B C6B O1B -67.85(16) . . . . ?
C4B C14B C15B C16B 179.94(16) . . . . ?
C4B C14B C19B C18B -179.04(16) . . . . ?
C5B C4B C14B C15B -72.72(19) . . . . ?
C5B C4B C14B C19B 105.71(17) . . . . ?
C6B O1B C7B C8B -36.2(3) . . . . ?
C6B O1B C7B C12B 149.16(16) . . . . ?
C7B O1B C6B C5B 160.55(15) . . . . ?
C7B C8B C9B C10B 1.6(3) . . . . ?
C8B C7B C12B C11B -2.9(3) . . . . ?
C8B C9B C10B O2B 179.28(17) . . . . ?
C8B C9B C10B C11B -2.6(3) . . . . ?
C9B C10B C11B O3B -178.30(17) . . . . ?
C9B C10B C11B C12B 0.8(3) . . . . ?
C10B O2B C13B O3B -19.95(19) . . . . ?
C10B C11B C12B C7B 2.0(3) . . . . ?
C11B O3B C13B O2B 20.12(19) . . . . ?
C12B C7B C8B C9B 1.2(3) . . . . ?
C13B O2B C10B C9B -169.35(18) . . . . ?
C13B O2B C10B C11B 12.32(19) . . . . ?
C13B O3B C11B C10B -12.57(19) . . . . ?
C13B O3B C11B C12B 168.41(18) . . . . ?
C14B C4B C5B C1B 178.92(12) . . . . ?
C14B C4B C5B C6B -57.94(16) . . . . ?
C14B C15B C16B C17B -1.1(3) . . . . ?
C15B C14B C19B C18B -0.6(3) . . . . ?
C15B C16B C17B C18B -0.2(3) . . . . ?
C15B C16B C17B F1B 179.71(17) . . . . ?
C16B C17B C18B C19B 1.0(3) . . . . ?
C17B C18B C19B C14B -0.7(3) . . . . ?
C19B C14B C15B C16B 1.5(3) . . . . ?
C20B C21B C22B C23B -178.34(14) . . . . ?
C21B C22B C23B O6B -173.39(14) . . . . ?
C21B C22B C23B O7B 5.9(2) . . . . ?
F1B C17B C18B C19B -178.83(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_prx-tart
_database_code_depnum_ccdc_archive 'CCDC 1869780'
loop_
_audit_author_name
_audit_author_address
'Matheus Souza'
;IFSC
Brazil
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            PRX-TART
_chemical_name_systematic        'Paroxetine tartrate'
_chemical_formula_moiety         
'0.5(C4 H4 O6), 0.5(C4 H6 O6), C19 H21 F N O3, 0.5(H2 O)'
_chemical_formula_sum            'C23 H27 F N O9.50'
_chemical_formula_weight         488.45
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   14.3395(17)
_cell_length_b                   7.9557(9)
_cell_length_c                   19.608(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.036(2)
_cell_angle_gamma                90
_cell_volume                     2220.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            55494
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.395
_diffrn_reflns_theta_min         1.873
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                9635
_reflns_number_total             11054
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.979
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 3868 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         11054
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.037
_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)+(0.0494P)²+0.8735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1024
_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,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 OW1(HW1A,HW1B)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7A), C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B)
2.c Secondary CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), C1A(H1AC,H1AD), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C13A(H13A,
 H13B), N1B(H1BA,H1BB), C1B(H1BC,H1BD), C2B(H2BA,H2BB), C3B(H3BA,H3BB),
 C6A(H6AA,H6AB), C6B(H6BA,H6BB), C13B(H13C,H13D)
2.d Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C15A(H15A), C16A(H16A), C18A(H18A),
 C19A(H19A), C8B(H8B), C9B(H9B), C12B(H12B), C15B(H15B), C16B(H16B), C18B(H18B),
  C19B(H19B)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6A), O7(H7), O9(H9), O10(H10), O11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.71456(13) 0.5903(3) 0.48465(10) 0.0137(4) Uani 1 1 d . . . . .
O3 O 0.43313(14) 0.3272(3) 0.60130(10) 0.0166(4) Uani 1 1 d . . . . .
O2 O 0.73704(13) 0.3632(3) 0.55182(10) 0.0160(4) Uani 1 1 d . . . . .
O4 O 0.39992(14) 0.6024(3) 0.59816(12) 0.0213(5) Uani 1 1 d . . . . .
O5 O 0.57081(13) 0.6967(2) 0.58920(10) 0.0127(4) Uani 1 1 d . . . . .
H5 H 0.5214 0.7446 0.5940 0.019 Uiso 1 1 calc GR . . . .
O6 O 0.52516(12) 0.5239(2) 0.46251(9) 0.0116(4) Uani 1 1 d . . . . .
H6A H 0.5483 0.6142 0.4534 0.017 Uiso 1 1 calc GR . . . .
O7 O 0.22638(14) 0.5505(3) 0.59224(13) 0.0236(5) Uani 1 1 d . . . . .
H7 H 0.2826 0.5731 0.5966 0.035 Uiso 1 1 calc GR . . . .
O8 O 0.20905(14) 0.8283(3) 0.60402(12) 0.0210(5) Uani 1 1 d . . . . .
O9 O 0.02181(15) 0.8043(3) 0.55946(12) 0.0259(5) Uani 1 1 d . . . . .
H9 H 0.0479 0.8826 0.5813 0.039 Uiso 1 1 calc GR . . . .
O10 O 0.05835(16) 0.6695(3) 0.69665(11) 0.0269(5) Uani 1 1 d . . . . .
H10 H 0.0113 0.7213 0.7043 0.040 Uiso 1 1 calc GR . . . .
O11 O -0.09102(14) 0.4335(3) 0.57531(11) 0.0217(5) Uani 1 1 d . . . . .
H11 H -0.1482 0.4211 0.5701 0.032 Uiso 1 1 calc GR . . . .
O12 O -0.12253(14) 0.6193(3) 0.65412(12) 0.0231(5) Uani 1 1 d . . . . .
C1 C 0.45389(18) 0.4780(4) 0.59652(13) 0.0122(5) Uani 1 1 d . . . . .
C2 C 0.55594(17) 0.5208(3) 0.58728(13) 0.0098(5) Uani 1 1 d . . . . .
H2 H 0.5975 0.4691 0.6249 0.012 Uiso 1 1 calc R . . . .
C3 C 0.58050(17) 0.4497(3) 0.51899(13) 0.0101(5) Uani 1 1 d . . . . .
H3 H 0.5669 0.3289 0.5183 0.012 Uiso 1 1 calc R . . . .
C4 C 0.68600(18) 0.4715(3) 0.51655(13) 0.0117(5) Uani 1 1 d . . . . .
C5 C 0.17779(19) 0.6890(4) 0.59187(14) 0.0140(5) Uani 1 1 d . . . . .
C6 C 0.07263(19) 0.6565(4) 0.57498(15) 0.0196(6) Uani 1 1 d . . . . .
H6 H 0.0623 0.5802 0.5355 0.023 Uiso 1 1 calc R . . . .
C7 C 0.0374(2) 0.5715(4) 0.63774(18) 0.0219(7) Uani 1 1 d . . . . .
H7A H 0.0684 0.4622 0.6453 0.026 Uiso 1 1 calc R . . . .
C8 C -0.0682(2) 0.5437(4) 0.62286(16) 0.0192(6) Uani 1 1 d . . . . .
O1A O 0.38647(14) 0.7614(3) 0.24035(10) 0.0154(4) Uani 1 1 d . . . . .
O2A O 0.64973(15) 0.9870(3) 0.14465(11) 0.0253(5) Uani 1 1 d . . . . .
O3A O 0.59890(15) 0.8927(3) 0.03457(11) 0.0267(5) Uani 1 1 d . . . . .
N1A N 0.31940(16) 0.5379(3) 0.41985(11) 0.0134(5) Uani 1 1 d . . . . .
H1AA H 0.3084 0.6385 0.4371 0.016 Uiso 1 1 calc R . . . .
H1AB H 0.3657 0.4902 0.4475 0.016 Uiso 1 1 calc R . . . .
C1A C 0.35011(18) 0.5602(4) 0.35030(13) 0.0128(5) Uani 1 1 d . . . . .
H1AC H 0.3667 0.4519 0.3325 0.015 Uiso 1 1 calc R . . . .
H1AD H 0.4053 0.6317 0.3537 0.015 Uiso 1 1 calc R . . . .
C2A C 0.23257(19) 0.4320(4) 0.41861(14) 0.0140(5) Uani 1 1 d . . . . .
H2AA H 0.2144 0.4235 0.4645 0.017 Uiso 1 1 calc R . . . .
H2AB H 0.2448 0.3196 0.4027 0.017 Uiso 1 1 calc R . . . .
C3A C 0.15393(18) 0.5129(4) 0.37059(14) 0.0135(5) Uani 1 1 d . . . . .
H3AA H 0.1397 0.6227 0.3882 0.016 Uiso 1 1 calc R . . . .
H3AB H 0.0978 0.4443 0.3688 0.016 Uiso 1 1 calc R . . . .
C4A C 0.18215(18) 0.5315(3) 0.29783(13) 0.0114(5) Uani 1 1 d . . . . .
H4A H 0.1973 0.4194 0.2817 0.014 Uiso 1 1 calc R . . . .
C5A C 0.27164(18) 0.6389(3) 0.30168(13) 0.0114(5) Uani 1 1 d . . . . .
H5A H 0.2579 0.7502 0.3194 0.014 Uiso 1 1 calc R . . . .
C7A C 0.43062(19) 0.7908(3) 0.18350(14) 0.0138(5) Uani 1 1 d . . . . .
C8A C 0.3991(2) 0.7350(4) 0.11819(15) 0.0178(6) Uani 1 1 d . . . . .
H8A H 0.3423 0.6774 0.1101 0.021 Uiso 1 1 calc R . . . .
C9A C 0.4521(2) 0.7644(4) 0.06380(15) 0.0213(6) Uani 1 1 d . . . . .
H9A H 0.4317 0.7275 0.0195 0.026 Uiso 1 1 calc R . . . .
C10A C 0.5348(2) 0.8495(4) 0.07858(14) 0.0172(6) Uani 1 1 d . . . . .
C11A C 0.5651(2) 0.9064(4) 0.14394(15) 0.0164(5) Uani 1 1 d . . . . .
C12A C 0.51502(19) 0.8814(4) 0.19798(14) 0.0143(5) Uani 1 1 d . . . . .
H12A H 0.5355 0.9218 0.2418 0.017 Uiso 1 1 calc R . . . .
C13A C 0.6763(2) 0.9634(4) 0.07735(15) 0.0216(6) Uani 1 1 d . . . . .
H13A H 0.6935 1.0704 0.0587 0.026 Uiso 1 1 calc R . . . .
H13B H 0.7301 0.8888 0.0794 0.026 Uiso 1 1 calc R . . . .
C14A C 0.10411(18) 0.6027(4) 0.24740(14) 0.0121(5) Uani 1 1 d . . . . .
C15A C 0.0767(2) 0.7703(4) 0.25302(15) 0.0199(6) Uani 1 1 d . . . . .
H15A H 0.1041 0.8345 0.2898 0.024 Uiso 1 1 calc R . . . .
C16A C 0.0100(2) 0.8426(4) 0.20532(16) 0.0208(6) Uani 1 1 d . . . . .
H16A H -0.0079 0.9541 0.2094 0.025 Uiso 1 1 calc R . . . .
C17A C -0.02888(19) 0.7455(4) 0.15183(14) 0.0158(6) Uani 1 1 d . . . . .
C18A C -0.0054(2) 0.5810(4) 0.14407(15) 0.0177(6) Uani 1 1 d . . . . .
H18A H -0.0338 0.5180 0.1073 0.021 Uiso 1 1 calc R . . . .
C19A C 0.06205(19) 0.5096(4) 0.19275(14) 0.0149(5) Uani 1 1 d . . . . .
H19A H 0.0790 0.3976 0.1883 0.018 Uiso 1 1 calc R . . . .
F1A F -0.09572(13) 0.8150(2) 0.10460(9) 0.0259(4) Uani 1 1 d . . . . .
O1B O 0.49601(14) 0.2742(3) 0.22408(10) 0.0178(4) Uani 1 1 d . . . . .
O2B O 0.13417(14) 0.1522(3) 0.11096(11) 0.0203(4) Uani 1 1 d . . . . .
O3B O 0.23291(14) 0.2728(3) 0.04001(10) 0.0200(4) Uani 1 1 d . . . . .
N1B N 0.68458(16) 0.6012(3) 0.33889(12) 0.0172(5) Uani 1 1 d . . . . .
H1BA H 0.6595 0.6652 0.3691 0.021 Uiso 1 1 calc R . . . .
H1BB H 0.7194 0.5229 0.3623 0.021 Uiso 1 1 calc R . . . .
C1B C 0.60755(19) 0.5174(4) 0.29344(14) 0.0153(5) Uani 1 1 d . . . . .
H1BC H 0.5636 0.6021 0.2737 0.018 Uiso 1 1 calc R . . . .
H1BD H 0.5739 0.4425 0.3209 0.018 Uiso 1 1 calc R . . . .
C2B C 0.7464(2) 0.7070(4) 0.30107(16) 0.0198(6) Uani 1 1 d . . . . .
H2BA H 0.7966 0.7541 0.3330 0.024 Uiso 1 1 calc R . . . .
H2BB H 0.7104 0.7990 0.2786 0.024 Uiso 1 1 calc R . . . .
C3B C 0.7874(2) 0.6008(4) 0.24805(15) 0.0209(6) Uani 1 1 d . . . . .
H3BA H 0.8259 0.5127 0.2712 0.025 Uiso 1 1 calc R . . . .
H3BB H 0.8274 0.6704 0.2233 0.025 Uiso 1 1 calc R . . . .
C4B C 0.71061(19) 0.5212(4) 0.19688(14) 0.0143(5) Uani 1 1 d . . . . .
H4B H 0.6738 0.6136 0.1741 0.017 Uiso 1 1 calc R . . . .
C6A C 0.30359(19) 0.6604(4) 0.23114(14) 0.0140(5) Uani 1 1 d . . . . .
H6AA H 0.3170 0.5519 0.2120 0.017 Uiso 1 1 calc R . . . .
H6AB H 0.2551 0.7153 0.2001 0.017 Uiso 1 1 calc R . . . .
C5B C 0.64305(19) 0.4170(4) 0.23543(14) 0.0135(5) Uani 1 1 d . . . . .
H5B H 0.6757 0.3163 0.2547 0.016 Uiso 1 1 calc R . . . .
C6B C 0.55808(19) 0.3643(4) 0.18589(14) 0.0150(5) Uani 1 1 d . . . . .
H6BA H 0.5267 0.4627 0.1647 0.018 Uiso 1 1 calc R . . . .
H6BB H 0.5776 0.2936 0.1499 0.018 Uiso 1 1 calc R . . . .
C7B C 0.40673(19) 0.2415(4) 0.19379(15) 0.0142(5) Uani 1 1 d . . . . .
C8B C 0.3474(2) 0.1698(3) 0.23649(14) 0.0147(5) Uani 1 1 d . . . . .
H8B H 0.3709 0.1449 0.2817 0.018 Uiso 1 1 calc R . . . .
C9B C 0.2537(2) 0.1342(4) 0.21356(14) 0.0161(6) Uani 1 1 d . . . . .
H9B H 0.2141 0.0855 0.2422 0.019 Uiso 1 1 calc R . . . .
C10B C 0.22285(19) 0.1746(4) 0.14675(15) 0.0152(5) Uani 1 1 d . . . . .
C11B C 0.2814(2) 0.2463(4) 0.10429(14) 0.0157(5) Uani 1 1 d . . . . .
C12B C 0.3747(2) 0.2797(4) 0.12488(14) 0.0154(5) Uani 1 1 d . . . . .
H12B H 0.4140 0.3246 0.0952 0.018 Uiso 1 1 calc R . . . .
C13B C 0.1363(2) 0.2485(5) 0.04970(15) 0.0221(6) Uani 1 1 d . . . . .
H13C H 0.1058 0.3562 0.0540 0.027 Uiso 1 1 calc R . . . .
H13D H 0.1034 0.1894 0.0107 0.027 Uiso 1 1 calc R . . . .
C14B C 0.75330(19) 0.4257(3) 0.14157(14) 0.0142(5) Uani 1 1 d . . . . .
C15B C 0.8176(2) 0.2957(4) 0.15900(15) 0.0171(6) Uani 1 1 d . . . . .
H15B H 0.8300 0.2617 0.2046 0.020 Uiso 1 1 calc R . . . .
C16B C 0.8631(2) 0.2171(4) 0.10931(17) 0.0208(6) Uani 1 1 d . . . . .
H16B H 0.9066 0.1321 0.1212 0.025 Uiso 1 1 calc R . . . .
C17B C 0.8425(2) 0.2676(4) 0.04224(16) 0.0211(6) Uani 1 1 d . . . . .
C18B C 0.7787(2) 0.3901(4) 0.02236(15) 0.0209(6) Uani 1 1 d . . . . .
H18B H 0.7651 0.4197 -0.0237 0.025 Uiso 1 1 calc R . . . .
C19B C 0.7340(2) 0.4704(4) 0.07299(15) 0.0177(6) Uani 1 1 d . . . . .
H19B H 0.6907 0.5552 0.0604 0.021 Uiso 1 1 calc R . . . .
F1B F 0.88719(15) 0.1904(3) -0.00667(10) 0.0338(5) Uani 1 1 d . . . . .
OW1 O 0.89814(17) 0.6512(4) 0.44028(13) 0.0320(6) Uani 1 1 d . . . . .
HW1A H 0.8471 0.6411 0.4579 0.048 Uiso 1 1 d G . . . .
HW1B H 0.9322 0.7145 0.4680 0.048 Uiso 1 1 d G . . . .


_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 C4 1.230(3) . ?
O3 C1 1.242(3) . ?
O2 C4 1.278(3) . ?
O4 C1 1.259(3) . ?
O5 H5 0.8200 . ?
O5 C2 1.416(3) . ?
O6 H6A 0.8200 . ?
O6 C3 1.411(3) . ?
O7 H7 0.8200 . ?
O7 C5 1.303(4) . ?
O8 C5 1.208(4) . ?
O9 H9 0.8200 . ?
O9 C6 1.397(4) . ?
O10 H10 0.8200 . ?
O10 C7 1.395(4) . ?
O11 H11 0.8200 . ?
O11 C8 1.293(4) . ?
O12 C8 1.209(4) . ?
C1 C2 1.535(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.534(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.529(4) . ?
C5 C6 1.526(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.543(4) . ?
C7 H7A 0.9800 . ?
C7 C8 1.522(4) . ?
O1A C7A 1.368(3) . ?
O1A C6A 1.428(3) . ?
O2A C11A 1.371(3) . ?
O2A C13A 1.430(4) . ?
O3A C10A 1.380(3) . ?
O3A C13A 1.423(4) . ?
N1A H1AA 0.8900 . ?
N1A H1AB 0.8900 . ?
N1A C1A 1.494(3) . ?
N1A C2A 1.501(4) . ?
C1A H1AC 0.9700 . ?
C1A H1AD 0.9700 . ?
C1A C5A 1.518(4) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.521(4) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C4A 1.537(4) . ?
C4A H4A 0.9800 . ?
C4A C5A 1.536(4) . ?
C4A C14A 1.510(4) . ?
C5A H5A 0.9800 . ?
C5A C6A 1.519(4) . ?
C7A C8A 1.378(4) . ?
C7A C12A 1.407(4) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.403(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.365(4) . ?
C10A C11A 1.378(4) . ?
C11A C12A 1.365(4) . ?
C12A H12A 0.9300 . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.398(4) . ?
C14A C19A 1.379(4) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.379(4) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.365(4) . ?
C17A C18A 1.365(4) . ?
C17A F1A 1.365(3) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.394(4) . ?
C19A H19A 0.9300 . ?
O1B C6B 1.425(3) . ?
O1B C7B 1.369(3) . ?
O2B C10B 1.387(3) . ?
O2B C13B 1.428(4) . ?
O3B C11B 1.379(3) . ?
O3B C13B 1.435(4) . ?
N1B H1BA 0.8900 . ?
N1B H1BB 0.8900 . ?
N1B C1B 1.489(4) . ?
N1B C2B 1.485(4) . ?
C1B H1BC 0.9700 . ?
C1B H1BD 0.9700 . ?
C1B C5B 1.527(4) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2B C3B 1.513(4) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C3B C4B 1.532(4) . ?
C4B H4B 0.9800 . ?
C4B C5B 1.542(4) . ?
C4B C14B 1.514(4) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C5B H5B 0.9800 . ?
C5B C6B 1.521(4) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C7B C8B 1.387(4) . ?
C7B C12B 1.406(4) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.394(4) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.368(4) . ?
C10B C11B 1.377(4) . ?
C11B C12B 1.375(4) . ?
C12B H12B 0.9300 . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.400(4) . ?
C14B C19B 1.386(4) . ?
C15B H15B 0.9300 . ?
C15B C16B 1.386(4) . ?
C16B H16B 0.9300 . ?
C16B C17B 1.372(5) . ?
C17B C18B 1.361(5) . ?
C17B F1B 1.363(3) . ?
C18B H18B 0.9300 . ?
C18B C19B 1.400(4) . ?
C19B H19B 0.9300 . ?
OW1 HW1A 0.8504 . ?
OW1 HW1B 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O5 H5 109.5 . . ?
C3 O6 H6A 109.5 . . ?
C5 O7 H7 109.5 . . ?
C6 O9 H9 109.5 . . ?
C7 O10 H10 109.5 . . ?
C8 O11 H11 109.5 . . ?
O3 C1 O4 127.1(3) . . ?
O3 C1 C2 117.6(2) . . ?
O4 C1 C2 115.2(2) . . ?
O5 C2 C1 111.0(2) . . ?
O5 C2 H2 108.6 . . ?
O5 C2 C3 109.8(2) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 C1 110.2(2) . . ?
C3 C2 H2 108.6 . . ?
O6 C3 C2 111.3(2) . . ?
O6 C3 H3 107.9 . . ?
O6 C3 C4 113.0(2) . . ?
C2 C3 H3 107.9 . . ?
C4 C3 C2 108.6(2) . . ?
C4 C3 H3 107.9 . . ?
O1 C4 O2 126.1(2) . . ?
O1 C4 C3 119.7(2) . . ?
O2 C4 C3 114.2(2) . . ?
O7 C5 C6 111.8(2) . . ?
O8 C5 O7 126.1(3) . . ?
O8 C5 C6 122.1(3) . . ?
O9 C6 C5 112.3(3) . . ?
O9 C6 H6 109.0 . . ?
O9 C6 C7 109.2(2) . . ?
C5 C6 H6 109.0 . . ?
C5 C6 C7 108.2(2) . . ?
C7 C6 H6 109.0 . . ?
O10 C7 C6 110.9(2) . . ?
O10 C7 H7A 108.8 . . ?
O10 C7 C8 110.4(2) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 C6 109.0(3) . . ?
C8 C7 H7A 108.8 . . ?
O11 C8 C7 113.3(3) . . ?
O12 C8 O11 125.5(3) . . ?
O12 C8 C7 121.2(3) . . ?
C7A O1A C6A 117.0(2) . . ?
C11A O2A C13A 105.4(2) . . ?
C10A O3A C13A 105.2(2) . . ?
H1AA N1A H1AB 107.8 . . ?
C1A N1A H1AA 109.0 . . ?
C1A N1A H1AB 109.0 . . ?
C1A N1A C2A 112.8(2) . . ?
C2A N1A H1AA 109.0 . . ?
C2A N1A H1AB 109.0 . . ?
N1A C1A H1AC 109.6 . . ?
N1A C1A H1AD 109.6 . . ?
N1A C1A C5A 110.1(2) . . ?
H1AC C1A H1AD 108.2 . . ?
C5A C1A H1AC 109.6 . . ?
C5A C1A H1AD 109.6 . . ?
N1A C2A H2AA 109.9 . . ?
N1A C2A H2AB 109.9 . . ?
N1A C2A C3A 108.8(2) . . ?
H2AA C2A H2AB 108.3 . . ?
C3A C2A H2AA 109.9 . . ?
C3A C2A H2AB 109.9 . . ?
C2A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
C2A C3A C4A 110.9(2) . . ?
H3AA C3A H3AB 108.1 . . ?
C4A C3A H3AA 109.5 . . ?
C4A C3A H3AB 109.5 . . ?
C3A C4A H4A 107.8 . . ?
C5A C4A C3A 108.8(2) . . ?
C5A C4A H4A 107.8 . . ?
C14A C4A C3A 112.7(2) . . ?
C14A C4A H4A 107.8 . . ?
C14A C4A C5A 111.8(2) . . ?
C1A C5A C4A 110.6(2) . . ?
C1A C5A H5A 108.5 . . ?
C1A C5A C6A 109.6(2) . . ?
C4A C5A H5A 108.5 . . ?
C6A C5A C4A 111.2(2) . . ?
C6A C5A H5A 108.5 . . ?
O1A C7A C8A 124.8(3) . . ?
O1A C7A C12A 113.3(2) . . ?
C8A C7A C12A 121.9(3) . . ?
C7A C8A H8A 119.8 . . ?
C7A C8A C9A 120.4(3) . . ?
C9A C8A H8A 119.8 . . ?
C8A C9A H9A 121.3 . . ?
C10A C9A C8A 117.3(3) . . ?
C10A C9A H9A 121.3 . . ?
C9A C10A O3A 128.2(3) . . ?
C9A C10A C11A 121.8(3) . . ?
C11A C10A O3A 110.0(3) . . ?
O2A C11A C10A 109.9(2) . . ?
C12A C11A O2A 127.5(3) . . ?
C12A C11A C10A 122.5(3) . . ?
C7A C12A H12A 122.0 . . ?
C11A C12A C7A 116.0(3) . . ?
C11A C12A H12A 122.0 . . ?
O2A C13A H13A 110.0 . . ?
O2A C13A H13B 110.0 . . ?
O3A C13A O2A 108.6(2) . . ?
O3A C13A H13A 110.0 . . ?
O3A C13A H13B 110.0 . . ?
H13A C13A H13B 108.4 . . ?
C15A C14A C4A 119.9(2) . . ?
C19A C14A C4A 121.7(2) . . ?
C19A C14A C15A 118.2(3) . . ?
C14A C15A H15A 119.3 . . ?
C16A C15A C14A 121.5(3) . . ?
C16A C15A H15A 119.3 . . ?
C15A C16A H16A 121.0 . . ?
C17A C16A C15A 118.0(3) . . ?
C17A C16A H16A 121.0 . . ?
C16A C17A F1A 118.6(3) . . ?
C18A C17A C16A 123.0(3) . . ?
C18A C17A F1A 118.4(3) . . ?
C17A C18A H18A 120.9 . . ?
C17A C18A C19A 118.3(3) . . ?
C19A C18A H18A 120.9 . . ?
C14A C19A C18A 120.9(3) . . ?
C14A C19A H19A 119.5 . . ?
C18A C19A H19A 119.5 . . ?
C7B O1B C6B 118.6(2) . . ?
C10B O2B C13B 104.1(2) . . ?
C11B O3B C13B 104.2(2) . . ?
H1BA N1B H1BB 107.7 . . ?
C1B N1B H1BA 108.9 . . ?
C1B N1B H1BB 108.9 . . ?
C2B N1B H1BA 108.9 . . ?
C2B N1B H1BB 108.9 . . ?
C2B N1B C1B 113.5(2) . . ?
N1B C1B H1BC 109.0 . . ?
N1B C1B H1BD 109.0 . . ?
N1B C1B C5B 112.9(2) . . ?
H1BC C1B H1BD 107.8 . . ?
C5B C1B H1BC 109.0 . . ?
C5B C1B H1BD 109.0 . . ?
N1B C2B H2BA 109.8 . . ?
N1B C2B H2BB 109.8 . . ?
N1B C2B C3B 109.4(3) . . ?
H2BA C2B H2BB 108.2 . . ?
C3B C2B H2BA 109.8 . . ?
C3B C2B H2BB 109.8 . . ?
C2B C3B H3BA 109.2 . . ?
C2B C3B H3BB 109.2 . . ?
C2B C3B C4B 111.9(2) . . ?
H3BA C3B H3BB 107.9 . . ?
C4B C3B H3BA 109.2 . . ?
C4B C3B H3BB 109.2 . . ?
C3B C4B H4B 107.0 . . ?
C3B C4B C5B 110.2(2) . . ?
C5B C4B H4B 107.0 . . ?
C14B C4B C3B 110.8(2) . . ?
C14B C4B H4B 107.0 . . ?
C14B C4B C5B 114.5(2) . . ?
O1A C6A C5A 106.7(2) . . ?
O1A C6A H6AA 110.4 . . ?
O1A C6A H6AB 110.4 . . ?
C5A C6A H6AA 110.4 . . ?
C5A C6A H6AB 110.4 . . ?
H6AA C6A H6AB 108.6 . . ?
C1B C5B C4B 111.8(2) . . ?
C1B C5B H5B 109.2 . . ?
C4B C5B H5B 109.2 . . ?
C6B C5B C1B 107.8(2) . . ?
C6B C5B C4B 109.7(2) . . ?
C6B C5B H5B 109.2 . . ?
O1B C6B C5B 107.8(2) . . ?
O1B C6B H6BA 110.1 . . ?
O1B C6B H6BB 110.1 . . ?
C5B C6B H6BA 110.1 . . ?
C5B C6B H6BB 110.1 . . ?
H6BA C6B H6BB 108.5 . . ?
O1B C7B C8B 115.2(2) . . ?
O1B C7B C12B 123.7(3) . . ?
C8B C7B C12B 121.1(3) . . ?
C7B C8B H8B 119.1 . . ?
C7B C8B C9B 121.8(3) . . ?
C9B C8B H8B 119.1 . . ?
C8B C9B H9B 121.7 . . ?
C10B C9B C8B 116.5(3) . . ?
C10B C9B H9B 121.7 . . ?
C9B C10B O2B 128.5(3) . . ?
C9B C10B C11B 121.8(3) . . ?
C11B C10B O2B 109.7(2) . . ?
C10B C11B O3B 109.8(2) . . ?
C12B C11B O3B 127.1(3) . . ?
C12B C11B C10B 123.1(3) . . ?
C7B C12B H12B 122.2 . . ?
C11B C12B C7B 115.6(3) . . ?
C11B C12B H12B 122.2 . . ?
O2B C13B O3B 107.7(2) . . ?
O2B C13B H13C 110.2 . . ?
O2B C13B H13D 110.2 . . ?
O3B C13B H13C 110.2 . . ?
O3B C13B H13D 110.2 . . ?
H13C C13B H13D 108.5 . . ?
C15B C14B C4B 120.5(2) . . ?
C19B C14B C4B 121.1(3) . . ?
C19B C14B C15B 118.3(3) . . ?
C14B C15B H15B 119.5 . . ?
C16B C15B C14B 121.0(3) . . ?
C16B C15B H15B 119.5 . . ?
C15B C16B H16B 120.8 . . ?
C17B C16B C15B 118.5(3) . . ?
C17B C16B H16B 120.8 . . ?
C18B C17B C16B 122.9(3) . . ?
C18B C17B F1B 118.6(3) . . ?
F1B C17B C16B 118.5(3) . . ?
C17B C18B H18B 120.9 . . ?
C17B C18B C19B 118.3(3) . . ?
C19B C18B H18B 120.9 . . ?
C14B C19B C18B 121.1(3) . . ?
C14B C19B H19B 119.4 . . ?
C18B C19B H19B 119.4 . . ?
HW1A OW1 HW1B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C2 O5 -174.4(2) . . . . ?
O3 C1 C2 C3 63.7(3) . . . . ?
O4 C1 C2 O5 5.8(3) . . . . ?
O4 C1 C2 C3 -116.0(3) . . . . ?
O5 C2 C3 O6 -59.3(3) . . . . ?
O5 C2 C3 C4 65.8(3) . . . . ?
O6 C3 C4 O1 25.1(3) . . . . ?
O6 C3 C4 O2 -157.7(2) . . . . ?
O7 C5 C6 O9 -166.7(2) . . . . ?
O7 C5 C6 C7 72.6(3) . . . . ?
O8 C5 C6 O9 14.2(4) . . . . ?
O8 C5 C6 C7 -106.5(3) . . . . ?
O9 C6 C7 O10 -66.4(3) . . . . ?
O9 C6 C7 C8 55.4(3) . . . . ?
O10 C7 C8 O11 -170.1(3) . . . . ?
O10 C7 C8 O12 9.4(4) . . . . ?
C1 C2 C3 O6 63.3(3) . . . . ?
C1 C2 C3 C4 -171.6(2) . . . . ?
C2 C3 C4 O1 -99.0(3) . . . . ?
C2 C3 C4 O2 78.2(3) . . . . ?
C5 C6 C7 O10 56.2(3) . . . . ?
C5 C6 C7 C8 178.0(2) . . . . ?
C6 C7 C8 O11 67.8(3) . . . . ?
C6 C7 C8 O12 -112.7(3) . . . . ?
O1A C7A C8A C9A -176.7(3) . . . . ?
O1A C7A C12A C11A 176.4(2) . . . . ?
O2A C11A C12A C7A -178.6(3) . . . . ?
O3A C10A C11A O2A -0.4(4) . . . . ?
O3A C10A C11A C12A 179.9(3) . . . . ?
N1A C1A C5A C4A -56.9(3) . . . . ?
N1A C1A C5A C6A -179.8(2) . . . . ?
N1A C2A C3A C4A 58.2(3) . . . . ?
C1A N1A C2A C3A -58.1(3) . . . . ?
C1A C5A C6A O1A -57.5(3) . . . . ?
C2A N1A C1A C5A 57.8(3) . . . . ?
C2A C3A C4A C5A -58.6(3) . . . . ?
C2A C3A C4A C14A 176.9(2) . . . . ?
C3A C4A C5A C1A 57.5(3) . . . . ?
C3A C4A C5A C6A 179.5(2) . . . . ?
C3A C4A C14A C15A 69.4(3) . . . . ?
C3A C4A C14A C19A -114.6(3) . . . . ?
C4A C5A C6A O1A 179.9(2) . . . . ?
C4A C14A C15A C16A 175.7(3) . . . . ?
C4A C14A C19A C18A -175.6(3) . . . . ?
C5A C4A C14A C15A -53.5(3) . . . . ?
C5A C4A C14A C19A 122.5(3) . . . . ?
C7A O1A C6A C5A 177.0(2) . . . . ?
C7A C8A C9A C10A 0.0(5) . . . . ?
C8A C7A C12A C11A -1.8(4) . . . . ?
C8A C9A C10A O3A 179.6(3) . . . . ?
C8A C9A C10A C11A -0.8(5) . . . . ?
C9A C10A C11A O2A 179.9(3) . . . . ?
C9A C10A C11A C12A 0.2(5) . . . . ?
C10A O3A C13A O2A -9.8(3) . . . . ?
C10A C11A C12A C7A 1.1(4) . . . . ?
C11A O2A C13A O3A 9.6(3) . . . . ?
C12A C7A C8A C9A 1.3(4) . . . . ?
C13A O2A C11A C10A -5.6(3) . . . . ?
C13A O2A C11A C12A 174.0(3) . . . . ?
C13A O3A C10A C9A -174.1(3) . . . . ?
C13A O3A C10A C11A 6.3(3) . . . . ?
C14A C4A C5A C1A -177.5(2) . . . . ?
C14A C4A C5A C6A -55.5(3) . . . . ?
C14A C15A C16A C17A -0.1(5) . . . . ?
C15A C14A C19A C18A 0.5(4) . . . . ?
C15A C16A C17A C18A 0.7(5) . . . . ?
C15A C16A C17A F1A 179.3(3) . . . . ?
C16A C17A C18A C19A -0.6(5) . . . . ?
C17A C18A C19A C14A 0.0(4) . . . . ?
C19A C14A C15A C16A -0.4(4) . . . . ?
F1A C17A C18A C19A -179.3(3) . . . . ?
O1B C7B C8B C9B 178.0(3) . . . . ?
O1B C7B C12B C11B -176.6(3) . . . . ?
O2B C10B C11B O3B 0.1(3) . . . . ?
O2B C10B C11B C12B -178.3(3) . . . . ?
O3B C11B C12B C7B 179.7(3) . . . . ?
N1B C1B C5B C4B -49.4(3) . . . . ?
N1B C1B C5B C6B -170.1(2) . . . . ?
N1B C2B C3B C4B 58.6(3) . . . . ?
C1B N1B C2B C3B -56.9(3) . . . . ?
C1B C5B C6B O1B -55.9(3) . . . . ?
C2B N1B C1B C5B 53.3(3) . . . . ?
C2B C3B C4B C5B -56.1(3) . . . . ?
C2B C3B C4B C14B 176.1(3) . . . . ?
C3B C4B C5B C1B 50.6(3) . . . . ?
C3B C4B C5B C6B 170.1(2) . . . . ?
C3B C4B C14B C15B 57.3(4) . . . . ?
C3B C4B C14B C19B -119.0(3) . . . . ?
C4B C5B C6B O1B -177.8(2) . . . . ?
C4B C14B C15B C16B -174.5(3) . . . . ?
C4B C14B C19B C18B 175.3(3) . . . . ?
C6A O1A C7A C8A 2.3(4) . . . . ?
C6A O1A C7A C12A -175.9(2) . . . . ?
C5B C4B C14B C15B -68.1(3) . . . . ?
C5B C4B C14B C19B 115.6(3) . . . . ?
C6B O1B C7B C8B -173.3(2) . . . . ?
C6B O1B C7B C12B 5.4(4) . . . . ?
C7B O1B C6B C5B 167.7(2) . . . . ?
C7B C8B C9B C10B -0.4(4) . . . . ?
C8B C7B C12B C11B 2.0(4) . . . . ?
C8B C9B C10B O2B 179.6(3) . . . . ?
C8B C9B C10B C11B 0.1(4) . . . . ?
C9B C10B C11B O3B 179.6(3) . . . . ?
C9B C10B C11B C12B 1.3(5) . . . . ?
C10B O2B C13B O3B 20.5(3) . . . . ?
C10B C11B C12B C7B -2.3(4) . . . . ?
C11B O3B C13B O2B -20.5(3) . . . . ?
C12B C7B C8B C9B -0.7(4) . . . . ?
C13B O2B C10B C9B 167.7(3) . . . . ?
C13B O2B C10B C11B -12.8(3) . . . . ?
C13B O3B C11B C10B 12.6(3) . . . . ?
C13B O3B C11B C12B -169.2(3) . . . . ?
C14B C4B C5B C1B 176.3(2) . . . . ?
C14B C4B C5B C6B -64.2(3) . . . . ?
C14B C15B C16B C17B -1.1(4) . . . . ?
C15B C14B C19B C18B -1.1(4) . . . . ?
C15B C16B C17B C18B -0.7(5) . . . . ?
C15B C16B C17B F1B 179.9(3) . . . . ?
C16B C17B C18B C19B 1.6(5) . . . . ?
C17B C18B C19B C14B -0.6(4) . . . . ?
C19B C14B C15B C16B 1.9(4) . . . . ?
F1B C17B C18B C19B -179.1(3) . . . . ?

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

data_prx_mal
_database_code_depnum_ccdc_archive 'CCDC 1869756'
loop_
_audit_author_name
_audit_author_address
'Matheus Souza'
;IFSC
Brazil
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            PRX-MAL
_chemical_name_systematic        'Paroxetine maleate'
_chemical_formula_moiety         'C19 H21 F N O3, C4 H3 O4'
_chemical_formula_sum            'C23 H24 F N O7'
_chemical_formula_weight         445.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.629(2)
_cell_length_b                   11.649(2)
_cell_length_c                   17.584(5)
_cell_angle_alpha                77.740(4)
_cell_angle_beta                 77.333(4)
_cell_angle_gamma                71.079(3)
_cell_volume                     2172.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    44075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      2.230
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44075
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.230
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                16370
_reflns_number_total             16775
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.692
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Flack x determined using 7124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1148
_refine_ls_number_reflns         16775
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      1.038
_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)+(0.1176P)²+1.4441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1708
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7444(18)
 0.2556(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C11A) = Uanis(C10A)
4. Rigid body (RIGU) restrains
 C14B, C19B, C18B, C17B, C16B, C15B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17A, C16A, C15A, C14A, C19A, C18A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O3A, C11A, C10A, O2A, C13A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7A, C8A, C9A, C10A, C11A, C12A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11C, C10C, C9C, C8C, C7C, C12C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Riding coordinates:
 O6A(H6A), O6B(H6B), O6C(H6C), O6D(H6D)
5.b Ternary CH refined with riding coordinates:
 C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B), C4C(H4C), C5C(H5C), C4D(H4D), C5D(H5D)
5.c Secondary CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), C1A(H1AC,H1AD), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C6A(H6AA,
 H6AB), C13A(H13A,H13B), N1B(H1BA,H1BB), C1B(H1BC,H1BD), C2B(H2BA,H2BB),
 C3B(H3BA,H3BB), C6B(H6BA,H6BB), C13B(H13C,H13D), N1C(H1CA,H1CB), C1C(H1CC,
 H1CD), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C6C(H6CA,H6CB), C13C(H13E,H13F),
 N1D(H1DA,H1DB), C1D(H1DC,H1DD), C2D(H2DA,H2DB), C3D(H3DA,H3DB), C6D(H6DA,H6DB),
  C13D(H13G,H13H)
5.d Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C9A(H9A), C12A(H12A), C15A(H15A), C16A(H16A), C18A(H18A),
 C19A(H19A), C21A(H21A), C22A(H22A), C8B(H8B), C9B(H9B), C12B(H12B), C15B(H15B),
  C16B(H16B), C18B(H18B), C19B(H19B), C21B(H21B), C22B(H22B), C8C(H8C),
 C9C(H9C), C12C(H12C), C15C(H15C), C16C(H16C), C18C(H18C), C19C(H19C),
 C21C(H21C), C22C(H22C), C8D(H8D), C9D(H9D), C12D(H12D), C15D(H15D), C16D(H16D),
  C18D(H18D), C19D(H19D), C21D(H21D), C22D(H22D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.4429(5) 0.2642(5) 0.5817(3) 0.0160(10) Uani 1 1 d . . . . .
H1AA H 0.3989 0.2445 0.5521 0.019 Uiso 1 1 calc R . . . .
H1AB H 0.5086 0.2830 0.5488 0.019 Uiso 1 1 calc R . . . .
O1A O 0.4881(4) -0.0879(4) 0.7353(2) 0.0157(8) Uani 1 1 d . . . . .
O2A O 0.7672(8) -0.5030(5) 0.8922(4) 0.059(2) Uani 1 1 d . U . . .
O3A O 0.7613(6) -0.4954(5) 0.7609(3) 0.0360(12) Uani 1 1 d . U . . .
O4A O 0.5826(4) 0.3829(4) 0.4674(3) 0.0210(9) Uani 1 1 d . . . . .
O5A O 0.6144(4) 0.4767(4) 0.5549(2) 0.0187(9) Uani 1 1 d . . . . .
O6A O 0.7241(4) 0.6231(4) 0.5546(2) 0.0174(9) Uani 1 1 d . . . . .
H6A H 0.6801 0.5768 0.5597 0.026 Uiso 1 1 d R . . . .
O7A O 0.8357(4) 0.7269(4) 0.4670(2) 0.0213(9) Uani 1 1 d . . . . .
C1A C 0.4889(5) 0.1555(5) 0.6398(3) 0.0142(11) Uani 1 1 d . . . . .
H1AC H 0.5472 0.1716 0.6668 0.017 Uiso 1 1 calc R . . . .
H1AD H 0.5341 0.0843 0.6120 0.017 Uiso 1 1 calc R . . . .
C2A C 0.3645(6) 0.3741(5) 0.6172(4) 0.0208(12) Uani 1 1 d . . . . .
H2AA H 0.3345 0.4418 0.5750 0.025 Uiso 1 1 calc R . . . .
H2AB H 0.4136 0.4012 0.6454 0.025 Uiso 1 1 calc R . . . .
C3A C 0.2562(6) 0.3457(6) 0.6739(4) 0.0221(12) Uani 1 1 d . . . . .
H3AA H 0.2037 0.3252 0.6446 0.027 Uiso 1 1 calc R . . . .
H3AB H 0.2063 0.4194 0.6981 0.027 Uiso 1 1 calc R . . . .
C4A C 0.2971(5) 0.2376(5) 0.7396(3) 0.0143(10) Uani 1 1 d . . . . .
H4A H 0.3449 0.2616 0.7713 0.017 Uiso 1 1 calc R . . . .
C5A C 0.3820(5) 0.1239(5) 0.7022(3) 0.0125(10) Uani 1 1 d . . . . .
H5A H 0.3319 0.0935 0.6759 0.015 Uiso 1 1 calc R . . . .
C6A C 0.4330(5) 0.0237(5) 0.7675(3) 0.0132(10) Uani 1 1 d . . . . .
H6AA H 0.4952 0.0454 0.7876 0.016 Uiso 1 1 calc R . . . .
H6AB H 0.3659 0.0142 0.8117 0.016 Uiso 1 1 calc R . . . .
C7A C 0.5493(5) -0.1890(5) 0.7835(3) 0.0143(10) Uani 1 1 d . U . . .
C8A C 0.5492(6) -0.1918(5) 0.8618(3) 0.0178(11) Uani 1 1 d . U . . .
H8A H 0.5016 -0.1228 0.8870 0.021 Uiso 1 1 calc R . . . .
C9A C 0.6201(8) -0.2977(7) 0.9048(4) 0.0309(15) Uani 1 1 d . U . . .
H9A H 0.6215 -0.3021 0.9591 0.037 Uiso 1 1 calc R . . . .
C10A C 0.6867(7) -0.3936(6) 0.8652(4) 0.0265(10) Uani 1 1 d . U . . .
C11A C 0.6834(7) -0.3904(6) 0.7872(4) 0.0265(10) Uani 1 1 d . U . . .
C12A C 0.6153(5) -0.2909(5) 0.7442(3) 0.0149(10) Uani 1 1 d . U . . .
H12A H 0.6122 -0.2897 0.6905 0.018 Uiso 1 1 calc R . . . .
C13A C 0.8030(8) -0.5732(7) 0.8297(5) 0.0359(17) Uani 1 1 d . U . . .
H13A H 0.7665 -0.6422 0.8439 0.043 Uiso 1 1 calc R . . . .
H13B H 0.8938 -0.6075 0.8197 0.043 Uiso 1 1 calc R . . . .
C14A C 0.1856(5) 0.2096(5) 0.7937(3) 0.0156(11) Uani 1 1 d . U . . .
C15A C 0.1027(5) 0.1749(5) 0.7631(4) 0.0180(11) Uani 1 1 d . U . . .
H15A H 0.1148 0.1723 0.7082 0.022 Uiso 1 1 calc R . . . .
C16A C 0.0013(6) 0.1438(6) 0.8133(5) 0.0278(14) Uani 1 1 d . U . . .
H16A H -0.0568 0.1226 0.7928 0.033 Uiso 1 1 calc R . . . .
C17A C -0.0115(6) 0.1450(6) 0.8918(5) 0.0310(15) Uani 1 1 d . U . . .
C18A C 0.0663(7) 0.1835(8) 0.9249(4) 0.0354(16) Uani 1 1 d . U . . .
H18A H 0.0520 0.1899 0.9794 0.042 Uiso 1 1 calc R . . . .
C19A C 0.1664(6) 0.2120(7) 0.8728(4) 0.0259(13) Uani 1 1 d . U . . .
H19A H 0.2238 0.2341 0.8935 0.031 Uiso 1 1 calc R . . . .
C20A C 0.6283(6) 0.4551(5) 0.4844(3) 0.0168(12) Uani 1 1 d . . . . .
C21A C 0.7041(6) 0.5158(5) 0.4187(4) 0.0191(12) Uani 1 1 d . . . . .
H21A H 0.7076 0.4962 0.3683 0.023 Uiso 1 1 calc R . . . .
C22A C 0.7677(6) 0.5924(5) 0.4181(3) 0.0156(11) Uani 1 1 d . . . . .
H22A H 0.8142 0.6135 0.3685 0.019 Uiso 1 1 calc R . . . .
C23A C 0.7773(5) 0.6504(5) 0.4833(3) 0.0139(10) Uani 1 1 d . . . . .
F1A F -0.1108(4) 0.1180(5) 0.9415(3) 0.0506(14) Uani 1 1 d . . . . .
N1B N 0.8785(5) 0.8191(5) 0.5878(3) 0.0181(10) Uani 1 1 d . . . . .
H1BA H 0.9368 0.8539 0.5582 0.022 Uiso 1 1 calc R . . . .
H1BB H 0.8301 0.8146 0.5550 0.022 Uiso 1 1 calc R . . . .
O1B O 0.7530(4) 1.1033(4) 0.7369(2) 0.0172(8) Uani 1 1 d . . . . .
O2B O 0.3951(7) 1.4509(5) 0.8899(4) 0.058(2) Uani 1 1 d . . . . .
O3B O 0.4649(5) 1.4994(4) 0.7575(3) 0.0306(11) Uani 1 1 d . . . . .
O4B O 0.0490(5) -0.0961(5) 0.4772(3) 0.0251(10) Uani 1 1 d . . . . .
O5B O 0.0999(4) -0.0118(4) 0.5617(2) 0.0184(9) Uani 1 1 d . . . . .
O6B O 0.2272(4) 0.1176(4) 0.5581(2) 0.0172(8) Uani 1 1 d . . . . .
H6B H 0.1827 0.0706 0.5650 0.026 Uiso 1 1 d R . . . .
O7B O 0.3548(4) 0.2019(4) 0.4689(3) 0.0208(9) Uani 1 1 d . . . . .
C1B C 0.8012(5) 0.8995(5) 0.6471(4) 0.0171(11) Uani 1 1 d . . . . .
H1BC H 0.7316 0.8675 0.6754 0.021 Uiso 1 1 calc R . . . .
H1BD H 0.7666 0.9835 0.6198 0.021 Uiso 1 1 calc R . . . .
C2B C 0.9410(6) 0.6918(6) 0.6245(4) 0.0212(12) Uani 1 1 d . . . . .
H2BA H 0.8784 0.6509 0.6538 0.025 Uiso 1 1 calc R . . . .
H2BB H 0.9924 0.6433 0.5828 0.025 Uiso 1 1 calc R . . . .
C3B C 1.0200(6) 0.6969(6) 0.6795(4) 0.0193(12) Uani 1 1 d . . . . .
H3BA H 1.0863 0.7322 0.6492 0.023 Uiso 1 1 calc R . . . .
H3BB H 1.0593 0.6124 0.7043 0.023 Uiso 1 1 calc R . . . .
C4B C 0.9453(5) 0.7748(5) 0.7446(3) 0.0143(10) Uani 1 1 d . . . . .
H4B H 0.8819 0.7352 0.7764 0.017 Uiso 1 1 calc R . . . .
C5B C 0.8781(5) 0.9042(5) 0.7071(3) 0.0116(10) Uani 1 1 d . . . . .
H5B H 0.9408 0.9472 0.6790 0.014 Uiso 1 1 calc R . . . .
C6B C 0.7945(5) 0.9763(5) 0.7717(3) 0.0139(10) Uani 1 1 d . . . . .
H6BA H 0.7231 0.9441 0.7941 0.017 Uiso 1 1 calc R . . . .
H6BB H 0.8405 0.9682 0.8147 0.017 Uiso 1 1 calc R . . . .
C7B C 0.6674(5) 1.1835(5) 0.7840(3) 0.0136(10) Uani 1 1 d . . . . .
C8B C 0.6288(6) 1.1540(6) 0.8629(4) 0.0223(13) Uani 1 1 d . . . . .
H8B H 0.6651 1.0745 0.8894 0.027 Uiso 1 1 calc R . . . .
C9B C 0.5367(7) 1.2392(6) 0.9050(4) 0.0319(17) Uani 1 1 d . . . . .
H9B H 0.5090 1.2189 0.9597 0.038 Uiso 1 1 calc R . . . .
C10B C 0.4875(7) 1.3538(6) 0.8641(4) 0.0278(14) Uani 1 1 d . . . . .
C11B C 0.5301(6) 1.3825(5) 0.7852(4) 0.0184(11) Uani 1 1 d . . . . .
C12B C 0.6196(5) 1.3021(5) 0.7427(3) 0.0143(10) Uani 1 1 d . . . . .
H12B H 0.6484 1.3243 0.6883 0.017 Uiso 1 1 calc R . . . .
C13B C 0.3870(7) 1.5493(7) 0.8264(4) 0.0322(16) Uani 1 1 d . . . . .
H13C H 0.4154 1.6140 0.8382 0.039 Uiso 1 1 calc R . . . .
H13D H 0.3007 1.5857 0.8171 0.039 Uiso 1 1 calc R . . . .
C14B C 1.0274(5) 0.7774(5) 0.7985(3) 0.0165(11) Uani 1 1 d . U . . .
C15B C 1.0125(6) 0.7233(7) 0.8780(4) 0.0265(14) Uani 1 1 d . U . . .
H15B H 0.9500 0.6835 0.8977 0.032 Uiso 1 1 calc R . . . .
C16B C 1.0870(7) 0.7268(9) 0.9281(4) 0.0390(18) Uani 1 1 d . U . . .
H16B H 1.0783 0.6879 0.9814 0.047 Uiso 1 1 calc R . . . .
C17B C 1.1737(7) 0.7876(8) 0.8989(5) 0.0361(16) Uani 1 1 d . U . . .
C18B C 1.1923(7) 0.8414(7) 0.8218(5) 0.0335(15) Uani 1 1 d . U . . .
H18B H 1.2548 0.8815 0.8036 0.040 Uiso 1 1 calc R . . . .
C19B C 1.1194(6) 0.8366(6) 0.7709(4) 0.0213(12) Uani 1 1 d . U . . .
H19B H 1.1316 0.8733 0.7173 0.026 Uiso 1 1 calc R . . . .
C20B C 0.1074(6) -0.0339(6) 0.4925(4) 0.0187(12) Uani 1 1 d . . . . .
C21B C 0.1888(6) 0.0173(6) 0.4249(4) 0.0180(12) Uani 1 1 d . . . . .
H21B H 0.1881 -0.0021 0.3752 0.022 Uiso 1 1 calc R . . . .
C22B C 0.2622(6) 0.0855(6) 0.4227(3) 0.0160(11) Uani 1 1 d . . . . .
H22B H 0.3087 0.1030 0.3724 0.019 Uiso 1 1 calc R . . . .
C23B C 0.2831(5) 0.1388(5) 0.4869(3) 0.0114(10) Uani 1 1 d . . . . .
F1B F 1.2475(6) 0.7929(7) 0.9481(4) 0.070(2) Uani 1 1 d . . . . .
N1C N 0.2029(5) 0.5867(5) 0.4125(3) 0.0170(10) Uani 1 1 d . . . . .
H1CA H 0.1692 0.5279 0.4422 0.020 Uiso 1 1 calc R . . . .
H1CB H 0.2054 0.6366 0.4451 0.020 Uiso 1 1 calc R . . . .
O1C O -0.0723(4) 0.7144(4) 0.2573(2) 0.0175(8) Uani 1 1 d . . . . .
O2C O -0.4026(6) 1.0488(8) 0.0827(4) 0.066(2) Uani 1 1 d . . . . .
O3C O -0.4650(5) 0.9947(6) 0.2171(4) 0.0432(15) Uani 1 1 d . . . . .
O4C O 0.2672(4) 0.6685(4) 0.5259(3) 0.0205(9) Uani 1 1 d . . . . .
O5C O 0.4038(4) 0.7441(4) 0.4380(2) 0.0183(9) Uani 1 1 d . . . . .
O6C O 0.5493(4) 0.8552(4) 0.4373(2) 0.0175(9) Uani 1 1 d . . . . .
H6C H 0.5033 0.8156 0.4323 0.026 Uiso 1 1 d R . . . .
O7C O 0.6085(4) 0.9257(4) 0.5246(3) 0.0225(9) Uani 1 1 d . . . . .
C1C C 0.1235(5) 0.6602(5) 0.3529(3) 0.0144(11) Uani 1 1 d . . . . .
H1CC H 0.1539 0.7307 0.3252 0.017 Uiso 1 1 calc R . . . .
H1CD H 0.0383 0.6931 0.3801 0.017 Uiso 1 1 calc R . . . .
C2C C 0.3313(6) 0.5265(6) 0.3754(4) 0.0204(12) Uani 1 1 d . . . . .
H2CA H 0.3800 0.4770 0.4171 0.024 Uiso 1 1 calc R . . . .
H2CB H 0.3708 0.5903 0.3464 0.024 Uiso 1 1 calc R . . . .
C3C C 0.3310(6) 0.4446(6) 0.3193(4) 0.0216(12) Uani 1 1 d . . . . .
H3CA H 0.2982 0.3767 0.3495 0.026 Uiso 1 1 calc R . . . .
H3CB H 0.4167 0.4081 0.2943 0.026 Uiso 1 1 calc R . . . .
C4C C 0.2533(5) 0.5148(5) 0.2553(3) 0.0162(11) Uani 1 1 d . . . . .
H4C H 0.2931 0.5768 0.2218 0.019 Uiso 1 1 calc R . . . .
C5C C 0.1222(5) 0.5844(5) 0.2930(3) 0.0147(10) Uani 1 1 d . . . . .
H5C H 0.0767 0.5233 0.3197 0.018 Uiso 1 1 calc R . . . .
C6C C 0.0551(5) 0.6686(5) 0.2269(3) 0.0151(11) Uani 1 1 d . . . . .
H6CA H 0.0906 0.7378 0.2055 0.018 Uiso 1 1 calc R . . . .
H6CB H 0.0653 0.6223 0.1835 0.018 Uiso 1 1 calc R . . . .
C7C C -0.1468(5) 0.7942(5) 0.2062(3) 0.0147(10) Uani 1 1 d . U . . .
C8C C -0.1091(6) 0.8263(6) 0.1269(4) 0.0231(13) Uani 1 1 d . U . . .
H8C H -0.0259 0.7912 0.1046 0.028 Uiso 1 1 calc R . . . .
C9C C -0.1898(7) 0.9090(8) 0.0782(4) 0.0348(16) Uani 1 1 d . U . . .
H9C H -0.1650 0.9290 0.0231 0.042 Uiso 1 1 calc R . . . .
C10C C -0.3074(7) 0.9596(7) 0.1153(5) 0.0338(16) Uani 1 1 d . U . . .
C11C C -0.3447(6) 0.9294(6) 0.1944(4) 0.0248(13) Uani 1 1 d . U . . .
C12C C -0.2695(5) 0.8441(6) 0.2424(4) 0.0172(11) Uani 1 1 d . U . . .
H12C H -0.2978 0.8199 0.2965 0.021 Uiso 1 1 calc R . . . .
C13C C -0.5054(8) 1.0650(8) 0.1458(6) 0.048(2) Uani 1 1 d . . . . .
H13E H -0.5398 1.1529 0.1516 0.057 Uiso 1 1 calc R . . . .
H13F H -0.5708 1.0374 0.1341 0.057 Uiso 1 1 calc R . . . .
C14C C 0.2472(5) 0.4300(5) 0.2027(4) 0.0173(11) Uani 1 1 d . . . . .
C15C C 0.2766(7) 0.4534(6) 0.1217(4) 0.0293(14) Uani 1 1 d . . . . .
H15C H 0.3051 0.5225 0.0979 0.035 Uiso 1 1 calc R . . . .
C16C C 0.2652(7) 0.3770(7) 0.0743(4) 0.0336(16) Uani 1 1 d . . . . .
H16C H 0.2861 0.3933 0.0185 0.040 Uiso 1 1 calc R . . . .
C17C C 0.2232(7) 0.2779(6) 0.1097(4) 0.0284(15) Uani 1 1 d . . . . .
C18C C 0.1942(6) 0.2507(6) 0.1890(4) 0.0255(14) Uani 1 1 d . . . . .
H18C H 0.1671 0.1805 0.2121 0.031 Uiso 1 1 calc R . . . .
C19C C 0.2052(6) 0.3283(6) 0.2363(4) 0.0211(12) Uani 1 1 d . . . . .
H19C H 0.1837 0.3114 0.2920 0.025 Uiso 1 1 calc R . . . .
C20C C 0.3468(6) 0.7242(5) 0.5080(4) 0.0171(12) Uani 1 1 d . . . . .
C21C C 0.3731(5) 0.7694(6) 0.5740(3) 0.0155(11) Uani 1 1 d . . . . .
H21C H 0.3290 0.7479 0.6245 0.019 Uiso 1 1 calc R . . . .
C22C C 0.4495(5) 0.8358(5) 0.5734(3) 0.0123(10) Uani 1 1 d . . . . .
H22C H 0.4438 0.8620 0.6220 0.015 Uiso 1 1 calc R . . . .
C23C C 0.5419(6) 0.8743(5) 0.5074(3) 0.0155(11) Uani 1 1 d . . . . .
F1C F 0.2116(5) 0.2038(4) 0.0627(3) 0.0438(12) Uani 1 1 d . . . . .
N1D N -0.2375(5) 0.0246(5) 0.4032(3) 0.0193(10) Uani 1 1 d . . . . .
H1DA H -0.2186 0.0686 0.4332 0.023 Uiso 1 1 calc R . . . .
H1DB H -0.2581 -0.0401 0.4357 0.023 Uiso 1 1 calc R . . . .
O1D O 0.1215(4) -0.0333(4) 0.2564(2) 0.0182(8) Uani 1 1 d . . . . .
O2D O 0.5495(5) -0.3094(8) 0.1019(4) 0.056(2) Uani 1 1 d . . . . .
O3D O 0.5315(5) -0.3051(5) 0.2356(3) 0.0322(12) Uani 1 1 d . . . . .
O4D O 0.7939(5) 0.1395(4) 0.5147(3) 0.0253(10) Uani 1 1 d . . . . .
O5D O 0.9186(4) 0.2343(4) 0.4305(3) 0.0202(9) Uani 1 1 d . . . . .
O6D O 1.0471(4) 0.3589(4) 0.4351(2) 0.0198(9) Uani 1 1 d . . . . .
H6D H 1.0036 0.3186 0.4271 0.030 Uiso 1 1 d R . . . .
O7D O 1.0867(4) 0.4421(4) 0.5248(3) 0.0192(9) Uani 1 1 d . . . . .
C1D C -0.1264(6) -0.0227(5) 0.3443(4) 0.0178(11) Uani 1 1 d . . . . .
H1DC H -0.1434 -0.0787 0.3159 0.021 Uiso 1 1 calc R . . . .
H1DD H -0.0563 -0.0702 0.3722 0.021 Uiso 1 1 calc R . . . .
C2D C -0.3465(6) 0.1046(6) 0.3650(4) 0.0206(12) Uani 1 1 d . . . . .
H2DA H -0.3711 0.0562 0.3347 0.025 Uiso 1 1 calc R . . . .
H2DB H -0.4172 0.1349 0.4060 0.025 Uiso 1 1 calc R . . . .
C3D C -0.3131(6) 0.2113(6) 0.3108(4) 0.0208(12) Uani 1 1 d . . . . .
H3DA H -0.2938 0.2621 0.3419 0.025 Uiso 1 1 calc R . . . .
H3DB H -0.3844 0.2629 0.2850 0.025 Uiso 1 1 calc R . . . .
C4D C -0.2007(5) 0.1676(5) 0.2468(3) 0.0161(11) Uani 1 1 d . . . . .
H4D H -0.2239 0.1213 0.2137 0.019 Uiso 1 1 calc R . . . .
C5D C -0.0916(5) 0.0810(5) 0.2853(3) 0.0150(11) Uani 1 1 d . . . . .
H5D H -0.0620 0.1293 0.3135 0.018 Uiso 1 1 calc R . . . .
C6D C 0.0135(5) 0.0272(5) 0.2216(3) 0.0164(11) Uani 1 1 d . . . . .
H6DA H -0.0087 -0.0319 0.1988 0.020 Uiso 1 1 calc R . . . .
H6DB H 0.0286 0.0936 0.1787 0.020 Uiso 1 1 calc R . . . .
C7D C 0.2268(5) -0.0950(5) 0.2098(3) 0.0162(11) Uani 1 1 d . . . . .
C8D C 0.2361(6) -0.0941(6) 0.1297(4) 0.0225(12) Uani 1 1 d . . . . .
H8D H 0.1690 -0.0464 0.1032 0.027 Uiso 1 1 calc R . . . .
C9D C 0.3447(6) -0.1637(8) 0.0873(4) 0.0304(16) Uani 1 1 d . . . . .
H9D H 0.3529 -0.1640 0.0324 0.036 Uiso 1 1 calc R . . . .
C10D C 0.4371(6) -0.2304(7) 0.1287(4) 0.0300(15) Uani 1 1 d . . . . .
C11D C 0.4277(6) -0.2286(6) 0.2078(4) 0.0207(12) Uani 1 1 d . . . . .
C12D C 0.3232(5) -0.1614(6) 0.2507(4) 0.0180(11) Uani 1 1 d . . . . .
H12D H 0.3173 -0.1604 0.3053 0.022 Uiso 1 1 calc R . . . .
C13D C 0.6140(6) -0.3525(8) 0.1684(4) 0.0324(16) Uani 1 1 d . . . . .
H13G H 0.6406 -0.4434 0.1785 0.039 Uiso 1 1 calc R . . . .
H13H H 0.6880 -0.3235 0.1576 0.039 Uiso 1 1 calc R . . . .
C14D C -0.1674(5) 0.2766(5) 0.1941(4) 0.0195(12) Uani 1 1 d . . . . .
C15D C -0.1773(8) 0.3012(7) 0.1146(4) 0.0332(16) Uani 1 1 d . . . . .
H15D H -0.2087 0.2511 0.0935 0.040 Uiso 1 1 calc R . . . .
C16D C -0.1420(9) 0.3976(8) 0.0664(4) 0.0410(19) Uani 1 1 d . . . . .
H16D H -0.1435 0.4116 0.0113 0.049 Uiso 1 1 calc R . . . .
C17D C -0.1043(7) 0.4734(6) 0.0998(5) 0.0359(18) Uani 1 1 d . . . . .
C18D C -0.0953(6) 0.4549(6) 0.1775(5) 0.0296(15) Uani 1 1 d . . . . .
H18D H -0.0673 0.5082 0.1982 0.036 Uiso 1 1 calc R . . . .
C19D C -0.1281(6) 0.3558(6) 0.2254(4) 0.0242(13) Uani 1 1 d . . . . .
H19D H -0.1239 0.3414 0.2801 0.029 Uiso 1 1 calc R . . . .
C20D C 0.8647(6) 0.2059(6) 0.4990(4) 0.0177(12) Uani 1 1 d . . . . .
C21D C 0.8806(6) 0.2527(5) 0.5688(3) 0.0160(11) Uani 1 1 d . . . . .
H21D H 0.8353 0.2279 0.6179 0.019 Uiso 1 1 calc R . . . .
C22D C 0.9498(5) 0.3246(5) 0.5714(3) 0.0135(11) Uani 1 1 d . . . . .
H22D H 0.9456 0.3434 0.6221 0.016 Uiso 1 1 calc R . . . .
C23D C 1.0324(5) 0.3790(5) 0.5058(3) 0.0129(11) Uani 1 1 d . . . . .
F1D F -0.0722(6) 0.5729(5) 0.0518(4) 0.0599(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A H1AA 0.9100 . ?
N1A H1AB 0.9100 . ?
N1A C1A 1.478(7) . ?
N1A C2A 1.481(8) . ?
O1A C6A 1.426(6) . ?
O1A C7A 1.382(6) . ?
O2A C10A 1.375(8) . ?
O2A C13A 1.417(10) . ?
O3A C11A 1.367(8) . ?
O3A C13A 1.424(9) . ?
O4A C20A 1.243(8) . ?
O5A C20A 1.283(8) . ?
O6A H6A 0.8358 . ?
O6A C23A 1.294(7) . ?
O7A C23A 1.239(7) . ?
C1A H1AC 0.9900 . ?
C1A H1AD 0.9900 . ?
C1A C5A 1.553(8) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.506(9) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.543(8) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.548(7) . ?
C4A C14A 1.516(8) . ?
C5A H5A 1.0000 . ?
C5A C6A 1.521(7) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C8A 1.370(8) . ?
C7A C12A 1.416(8) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.411(8) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.366(10) . ?
C10A C11A 1.373(10) . ?
C11A C12A 1.355(8) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.397(8) . ?
C14A C19A 1.366(9) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.410(9) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.357(12) . ?
C17A C18A 1.402(12) . ?
C17A F1A 1.369(8) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.399(10) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.491(9) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.328(9) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.488(8) . ?
N1B H1BA 0.9100 . ?
N1B H1BB 0.9100 . ?
N1B C1B 1.494(7) . ?
N1B C2B 1.498(8) . ?
O1B C6B 1.442(6) . ?
O1B C7B 1.384(7) . ?
O2B C10B 1.362(8) . ?
O2B C13B 1.416(9) . ?
O3B C11B 1.370(7) . ?
O3B C13B 1.451(8) . ?
O4B C20B 1.241(8) . ?
O5B C20B 1.275(8) . ?
O6B H6B 0.8426 . ?
O6B C23B 1.292(7) . ?
O7B C23B 1.233(7) . ?
C1B H1BC 0.9900 . ?
C1B H1BD 0.9900 . ?
C1B C5B 1.544(7) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.493(9) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.543(8) . ?
C4B H4B 1.0000 . ?
C4B C5B 1.536(7) . ?
C4B C14B 1.496(8) . ?
C5B H5B 1.0000 . ?
C5B C6B 1.528(7) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.366(9) . ?
C7B C12B 1.414(7) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.399(9) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.380(9) . ?
C10B C11B 1.375(9) . ?
C11B C12B 1.358(8) . ?
C12B H12B 0.9500 . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.405(9) . ?
C14B C19B 1.401(9) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.378(10) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.365(13) . ?
C17B C18B 1.370(13) . ?
C17B F1B 1.368(8) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.382(10) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.495(9) . ?
C21B H21B 0.9500 . ?
C21B C22B 1.331(9) . ?
C22B H22B 0.9500 . ?
C22B C23B 1.495(7) . ?
N1C H1CA 0.9100 . ?
N1C H1CB 0.9100 . ?
N1C C1C 1.488(7) . ?
N1C C2C 1.494(8) . ?
O1C C6C 1.424(7) . ?
O1C C7C 1.373(7) . ?
O2C C10C 1.384(9) . ?
O2C C13C 1.434(12) . ?
O3C C11C 1.374(8) . ?
O3C C13C 1.426(10) . ?
O4C C20C 1.246(8) . ?
O5C C20C 1.276(8) . ?
O6C H6C 0.8395 . ?
O6C C23C 1.277(7) . ?
O7C C23C 1.238(7) . ?
C1C H1CC 0.9900 . ?
C1C H1CD 0.9900 . ?
C1C C5C 1.518(8) . ?
C2C H2CA 0.9900 . ?
C2C H2CB 0.9900 . ?
C2C C3C 1.512(9) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C3C C4C 1.527(8) . ?
C4C H4C 1.0000 . ?
C4C C5C 1.550(8) . ?
C4C C14C 1.517(8) . ?
C5C H5C 1.0000 . ?
C5C C6C 1.529(7) . ?
C6C H6CA 0.9900 . ?
C6C H6CB 0.9900 . ?
C7C C8C 1.375(9) . ?
C7C C12C 1.414(8) . ?
C8C H8C 0.9500 . ?
C8C C9C 1.400(9) . ?
C9C H9C 0.9500 . ?
C9C C10C 1.376(11) . ?
C10C C11C 1.369(11) . ?
C11C C12C 1.366(9) . ?
C12C H12C 0.9500 . ?
C13C H13E 0.9900 . ?
C13C H13F 0.9900 . ?
C14C C15C 1.378(10) . ?
C14C C19C 1.394(9) . ?
C15C H15C 0.9500 . ?
C15C C16C 1.395(11) . ?
C16C H16C 0.9500 . ?
C16C C17C 1.373(11) . ?
C17C C18C 1.355(11) . ?
C17C F1C 1.369(8) . ?
C18C H18C 0.9500 . ?
C18C C19C 1.402(9) . ?
C19C H19C 0.9500 . ?
C20C C21C 1.497(8) . ?
C21C H21C 0.9500 . ?
C21C C22C 1.351(9) . ?
C22C H22C 0.9500 . ?
C22C C23C 1.499(8) . ?
N1D H1DA 0.9100 . ?
N1D H1DB 0.9100 . ?
N1D C1D 1.496(8) . ?
N1D C2D 1.506(8) . ?
O1D C6D 1.424(7) . ?
O1D C7D 1.387(7) . ?
O2D C10D 1.382(9) . ?
O2D C13D 1.439(9) . ?
O3D C11D 1.366(8) . ?
O3D C13D 1.435(8) . ?
O4D C20D 1.256(8) . ?
O5D C20D 1.260(8) . ?
O6D H6D 0.8428 . ?
O6D C23D 1.280(7) . ?
O7D C23D 1.243(7) . ?
C1D H1DC 0.9900 . ?
C1D H1DD 0.9900 . ?
C1D C5D 1.516(8) . ?
C2D H2DA 0.9900 . ?
C2D H2DB 0.9900 . ?
C2D C3D 1.500(9) . ?
C3D H3DA 0.9900 . ?
C3D H3DB 0.9900 . ?
C3D C4D 1.549(8) . ?
C4D H4D 1.0000 . ?
C4D C5D 1.530(7) . ?
C4D C14D 1.511(8) . ?
C5D H5D 1.0000 . ?
C5D C6D 1.530(8) . ?
C6D H6DA 0.9900 . ?
C6D H6DB 0.9900 . ?
C7D C8D 1.388(9) . ?
C7D C12D 1.388(8) . ?
C8D H8D 0.9500 . ?
C8D C9D 1.409(9) . ?
C9D H9D 0.9500 . ?
C9D C10D 1.360(10) . ?
C10D C11D 1.375(9) . ?
C11D C12D 1.375(8) . ?
C12D H12D 0.9500 . ?
C13D H13G 0.9900 . ?
C13D H13H 0.9900 . ?
C14D C15D 1.388(10) . ?
C14D C19D 1.401(9) . ?
C15D H15D 0.9500 . ?
C15D C16D 1.376(12) . ?
C16D H16D 0.9500 . ?
C16D C17D 1.378(13) . ?
C17D C18D 1.359(12) . ?
C17D F1D 1.385(8) . ?
C18D H18D 0.9500 . ?
C18D C19D 1.385(10) . ?
C19D H19D 0.9500 . ?
C20D C21D 1.512(8) . ?
C21D H21D 0.9500 . ?
C21D C22D 1.349(9) . ?
C22D H22D 0.9500 . ?
C22D C23D 1.501(8) . ?

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
H1AA N1A H1AB 107.6 . . ?
C1A N1A H1AA 108.7 . . ?
C1A N1A H1AB 108.7 . . ?
C1A N1A C2A 114.2(5) . . ?
C2A N1A H1AA 108.7 . . ?
C2A N1A H1AB 108.7 . . ?
C7A O1A C6A 117.2(4) . . ?
C10A O2A C13A 105.5(5) . . ?
C11A O3A C13A 104.7(5) . . ?
C23A O6A H6A 115.1 . . ?
N1A C1A H1AC 109.3 . . ?
N1A C1A H1AD 109.3 . . ?
N1A C1A C5A 111.5(5) . . ?
H1AC C1A H1AD 108.0 . . ?
C5A C1A H1AC 109.3 . . ?
C5A C1A H1AD 109.3 . . ?
N1A C2A H2AA 109.6 . . ?
N1A C2A H2AB 109.6 . . ?
N1A C2A C3A 110.4(5) . . ?
H2AA C2A H2AB 108.1 . . ?
C3A C2A H2AA 109.6 . . ?
C3A C2A H2AB 109.6 . . ?
C2A C3A H3AA 109.2 . . ?
C2A C3A H3AB 109.2 . . ?
C2A C3A C4A 112.0(5) . . ?
H3AA C3A H3AB 107.9 . . ?
C4A C3A H3AA 109.2 . . ?
C4A C3A H3AB 109.2 . . ?
C3A C4A H4A 108.6 . . ?
C3A C4A C5A 109.6(5) . . ?
C5A C4A H4A 108.6 . . ?
C14A C4A C3A 110.2(5) . . ?
C14A C4A H4A 108.6 . . ?
C14A C4A C5A 111.2(4) . . ?
C1A C5A H5A 108.8 . . ?
C4A C5A C1A 111.6(4) . . ?
C4A C5A H5A 108.8 . . ?
C6A C5A C1A 110.3(4) . . ?
C6A C5A C4A 108.6(4) . . ?
C6A C5A H5A 108.8 . . ?
O1A C6A C5A 107.9(4) . . ?
O1A C6A H6AA 110.1 . . ?
O1A C6A H6AB 110.1 . . ?
C5A C6A H6AA 110.1 . . ?
C5A C6A H6AB 110.1 . . ?
H6AA C6A H6AB 108.4 . . ?
O1A C7A C12A 113.7(5) . . ?
C8A C7A O1A 124.1(5) . . ?
C8A C7A C12A 122.2(5) . . ?
C7A C8A H8A 120.2 . . ?
C7A C8A C9A 119.6(6) . . ?
C9A C8A H8A 120.2 . . ?
C8A C9A H9A 121.3 . . ?
C10A C9A C8A 117.4(6) . . ?
C10A C9A H9A 121.3 . . ?
C9A C10A O2A 128.6(6) . . ?
C9A C10A C11A 122.2(6) . . ?
C11A C10A O2A 109.1(6) . . ?
O3A C11A C10A 110.7(6) . . ?
C12A C11A O3A 127.1(6) . . ?
C12A C11A C10A 122.1(6) . . ?
C7A C12A H12A 121.8 . . ?
C11A C12A C7A 116.4(5) . . ?
C11A C12A H12A 121.8 . . ?
O2A C13A O3A 108.6(5) . . ?
O2A C13A H13A 110.0 . . ?
O2A C13A H13B 110.0 . . ?
O3A C13A H13A 110.0 . . ?
O3A C13A H13B 110.0 . . ?
H13A C13A H13B 108.4 . . ?
C15A C14A C4A 119.7(5) . . ?
C19A C14A C4A 121.6(5) . . ?
C19A C14A C15A 118.7(6) . . ?
C14A C15A H15A 119.9 . . ?
C14A C15A C16A 120.2(6) . . ?
C16A C15A H15A 119.9 . . ?
C15A C16A H16A 120.8 . . ?
C17A C16A C15A 118.5(6) . . ?
C17A C16A H16A 120.8 . . ?
C16A C17A C18A 123.3(6) . . ?
C16A C17A F1A 119.6(7) . . ?
F1A C17A C18A 116.8(7) . . ?
C17A C18A H18A 122.1 . . ?
C19A C18A C17A 115.9(7) . . ?
C19A C18A H18A 122.1 . . ?
C14A C19A C18A 123.2(7) . . ?
C14A C19A H19A 118.4 . . ?
C18A C19A H19A 118.4 . . ?
O4A C20A O5A 122.9(6) . . ?
O4A C20A C21A 117.1(5) . . ?
O5A C20A C21A 120.0(6) . . ?
C20A C21A H21A 114.3 . . ?
C22A C21A C20A 131.4(6) . . ?
C22A C21A H21A 114.3 . . ?
C21A C22A H22A 115.0 . . ?
C21A C22A C23A 129.9(6) . . ?
C23A C22A H22A 115.0 . . ?
O6A C23A C22A 120.8(5) . . ?
O7A C23A O6A 121.1(5) . . ?
O7A C23A C22A 118.1(5) . . ?
H1BA N1B H1BB 107.8 . . ?
C1B N1B H1BA 109.0 . . ?
C1B N1B H1BB 109.0 . . ?
C1B N1B C2B 113.1(4) . . ?
C2B N1B H1BA 109.0 . . ?
C2B N1B H1BB 109.0 . . ?
C7B O1B C6B 117.3(4) . . ?
C10B O2B C13B 106.7(5) . . ?
C11B O3B C13B 105.4(5) . . ?
C23B O6B H6B 115.5 . . ?
N1B C1B H1BC 109.5 . . ?
N1B C1B H1BD 109.5 . . ?
N1B C1B C5B 110.8(5) . . ?
H1BC C1B H1BD 108.1 . . ?
C5B C1B H1BC 109.5 . . ?
C5B C1B H1BD 109.5 . . ?
N1B C2B H2BA 109.7 . . ?
N1B C2B H2BB 109.7 . . ?
H2BA C2B H2BB 108.2 . . ?
C3B C2B N1B 110.0(5) . . ?
C3B C2B H2BA 109.7 . . ?
C3B C2B H2BB 109.7 . . ?
C2B C3B H3BA 109.2 . . ?
C2B C3B H3BB 109.2 . . ?
C2B C3B C4B 112.0(5) . . ?
H3BA C3B H3BB 107.9 . . ?
C4B C3B H3BA 109.2 . . ?
C4B C3B H3BB 109.2 . . ?
C3B C4B H4B 108.1 . . ?
C5B C4B C3B 109.9(5) . . ?
C5B C4B H4B 108.1 . . ?
C14B C4B C3B 110.4(5) . . ?
C14B C4B H4B 108.1 . . ?
C14B C4B C5B 112.2(4) . . ?
C1B C5B H5B 108.7 . . ?
C4B C5B C1B 111.5(4) . . ?
C4B C5B H5B 108.7 . . ?
C6B C5B C1B 109.8(4) . . ?
C6B C5B C4B 109.4(4) . . ?
C6B C5B H5B 108.7 . . ?
O1B C6B C5B 107.8(4) . . ?
O1B C6B H6BA 110.1 . . ?
O1B C6B H6BB 110.1 . . ?
C5B C6B H6BA 110.1 . . ?
C5B C6B H6BB 110.1 . . ?
H6BA C6B H6BB 108.5 . . ?
O1B C7B C12B 113.6(5) . . ?
C8B C7B O1B 124.8(5) . . ?
C8B C7B C12B 121.5(5) . . ?
C7B C8B H8B 119.6 . . ?
C7B C8B C9B 120.9(6) . . ?
C9B C8B H8B 119.6 . . ?
C8B C9B H9B 121.2 . . ?
C10B C9B C8B 117.6(6) . . ?
C10B C9B H9B 121.2 . . ?
O2B C10B C9B 129.4(6) . . ?
O2B C10B C11B 110.1(6) . . ?
C11B C10B C9B 120.5(6) . . ?
O3B C11B C10B 109.7(5) . . ?
C12B C11B O3B 126.8(5) . . ?
C12B C11B C10B 123.4(6) . . ?
C7B C12B H12B 122.0 . . ?
C11B C12B C7B 116.0(5) . . ?
C11B C12B H12B 122.0 . . ?
O2B C13B O3B 107.1(5) . . ?
O2B C13B H13C 110.3 . . ?
O2B C13B H13D 110.3 . . ?
O3B C13B H13C 110.3 . . ?
O3B C13B H13D 110.3 . . ?
H13C C13B H13D 108.6 . . ?
C15B C14B C4B 121.0(5) . . ?
C19B C14B C4B 120.5(5) . . ?
C19B C14B C15B 118.5(6) . . ?
C14B C15B H15B 119.4 . . ?
C16B C15B C14B 121.2(7) . . ?
C16B C15B H15B 119.4 . . ?
C15B C16B H16B 120.9 . . ?
C17B C16B C15B 118.2(7) . . ?
C17B C16B H16B 120.9 . . ?
C16B C17B C18B 122.9(7) . . ?
C16B C17B F1B 118.9(8) . . ?
F1B C17B C18B 118.2(8) . . ?
C17B C18B H18B 120.4 . . ?
C17B C18B C19B 119.3(7) . . ?
C19B C18B H18B 120.4 . . ?
C14B C19B H19B 120.0 . . ?
C18B C19B C14B 119.9(7) . . ?
C18B C19B H19B 120.0 . . ?
O4B C20B O5B 123.3(6) . . ?
O4B C20B C21B 116.9(5) . . ?
O5B C20B C21B 119.9(6) . . ?
C20B C21B H21B 114.6 . . ?
C22B C21B C20B 130.8(6) . . ?
C22B C21B H21B 114.6 . . ?
C21B C22B H22B 114.9 . . ?
C21B C22B C23B 130.3(6) . . ?
C23B C22B H22B 114.9 . . ?
O6B C23B C22B 120.0(5) . . ?
O7B C23B O6B 122.5(5) . . ?
O7B C23B C22B 117.5(5) . . ?
H1CA N1C H1CB 107.9 . . ?
C1C N1C H1CA 109.1 . . ?
C1C N1C H1CB 109.1 . . ?
C1C N1C C2C 112.4(5) . . ?
C2C N1C H1CA 109.1 . . ?
C2C N1C H1CB 109.1 . . ?
C7C O1C C6C 117.3(4) . . ?
C10C O2C C13C 105.1(6) . . ?
C11C O3C C13C 104.9(6) . . ?
C23C O6C H6C 115.4 . . ?
N1C C1C H1CC 109.2 . . ?
N1C C1C H1CD 109.2 . . ?
N1C C1C C5C 111.9(4) . . ?
H1CC C1C H1CD 107.9 . . ?
C5C C1C H1CC 109.2 . . ?
C5C C1C H1CD 109.2 . . ?
N1C C2C H2CA 109.5 . . ?
N1C C2C H2CB 109.5 . . ?
N1C C2C C3C 110.8(5) . . ?
H2CA C2C H2CB 108.1 . . ?
C3C C2C H2CA 109.5 . . ?
C3C C2C H2CB 109.5 . . ?
C2C C3C H3CA 109.2 . . ?
C2C C3C H3CB 109.2 . . ?
C2C C3C C4C 112.0(5) . . ?
H3CA C3C H3CB 107.9 . . ?
C4C C3C H3CA 109.2 . . ?
C4C C3C H3CB 109.2 . . ?
C3C C4C H4C 108.1 . . ?
C3C C4C C5C 110.3(5) . . ?
C5C C4C H4C 108.1 . . ?
C14C C4C C3C 111.4(5) . . ?
C14C C4C H4C 108.1 . . ?
C14C C4C C5C 110.8(5) . . ?
C1C C5C C4C 112.9(5) . . ?
C1C C5C H5C 108.8 . . ?
C1C C5C C6C 109.4(4) . . ?
C4C C5C H5C 108.8 . . ?
C6C C5C C4C 108.1(4) . . ?
C6C C5C H5C 108.8 . . ?
O1C C6C C5C 109.3(4) . . ?
O1C C6C H6CA 109.8 . . ?
O1C C6C H6CB 109.8 . . ?
C5C C6C H6CA 109.8 . . ?
C5C C6C H6CB 109.8 . . ?
H6CA C6C H6CB 108.3 . . ?
O1C C7C C8C 124.8(5) . . ?
O1C C7C C12C 113.9(5) . . ?
C8C C7C C12C 121.3(5) . . ?
C7C C8C H8C 119.1 . . ?
C7C C8C C9C 121.9(6) . . ?
C9C C8C H8C 119.1 . . ?
C8C C9C H9C 122.2 . . ?
C10C C9C C8C 115.6(6) . . ?
C10C C9C H9C 122.2 . . ?
C9C C10C O2C 127.7(7) . . ?
C11C C10C O2C 109.6(7) . . ?
C11C C10C C9C 122.6(6) . . ?
C10C C11C O3C 111.1(6) . . ?
C12C C11C O3C 126.1(7) . . ?
C12C C11C C10C 122.8(6) . . ?
C7C C12C H12C 122.2 . . ?
C11C C12C C7C 115.6(6) . . ?
C11C C12C H12C 122.2 . . ?
O2C C13C H13E 109.9 . . ?
O2C C13C H13F 109.9 . . ?
O3C C13C O2C 108.9(6) . . ?
O3C C13C H13E 109.9 . . ?
O3C C13C H13F 109.9 . . ?
H13E C13C H13F 108.3 . . ?
C15C C14C C4C 121.9(6) . . ?
C15C C14C C19C 118.6(6) . . ?
C19C C14C C4C 119.5(5) . . ?
C14C C15C H15C 119.5 . . ?
C14C C15C C16C 120.9(7) . . ?
C16C C15C H15C 119.5 . . ?
C15C C16C H16C 120.6 . . ?
C17C C16C C15C 118.7(6) . . ?
C17C C16C H16C 120.6 . . ?
C18C C17C C16C 122.4(6) . . ?
C18C C17C F1C 119.2(7) . . ?
F1C C17C C16C 118.4(7) . . ?
C17C C18C H18C 120.7 . . ?
C17C C18C C19C 118.5(6) . . ?
C19C C18C H18C 120.7 . . ?
C14C C19C C18C 120.8(6) . . ?
C14C C19C H19C 119.6 . . ?
C18C C19C H19C 119.6 . . ?
O4C C20C O5C 123.6(6) . . ?
O4C C20C C21C 116.1(6) . . ?
O5C C20C C21C 120.3(5) . . ?
C20C C21C H21C 114.8 . . ?
C22C C21C C20C 130.3(5) . . ?
C22C C21C H21C 114.8 . . ?
C21C C22C H22C 115.2 . . ?
C21C C22C C23C 129.7(5) . . ?
C23C C22C H22C 115.2 . . ?
O6C C23C C22C 120.9(5) . . ?
O7C C23C O6C 122.7(6) . . ?
O7C C23C C22C 116.4(5) . . ?
H1DA N1D H1DB 107.8 . . ?
C1D N1D H1DA 109.1 . . ?
C1D N1D H1DB 109.1 . . ?
C1D N1D C2D 112.6(5) . . ?
C2D N1D H1DA 109.1 . . ?
C2D N1D H1DB 109.1 . . ?
C7D O1D C6D 118.4(4) . . ?
C10D O2D C13D 105.6(5) . . ?
C11D O3D C13D 105.8(5) . . ?
C23D O6D H6D 116.2 . . ?
N1D C1D H1DC 109.3 . . ?
N1D C1D H1DD 109.3 . . ?
N1D C1D C5D 111.6(5) . . ?
H1DC C1D H1DD 108.0 . . ?
C5D C1D H1DC 109.3 . . ?
C5D C1D H1DD 109.3 . . ?
N1D C2D H2DA 109.8 . . ?
N1D C2D H2DB 109.8 . . ?
H2DA C2D H2DB 108.2 . . ?
C3D C2D N1D 109.5(5) . . ?
C3D C2D H2DA 109.8 . . ?
C3D C2D H2DB 109.8 . . ?
C2D C3D H3DA 109.4 . . ?
C2D C3D H3DB 109.4 . . ?
C2D C3D C4D 111.4(5) . . ?
H3DA C3D H3DB 108.0 . . ?
C4D C3D H3DA 109.4 . . ?
C4D C3D H3DB 109.4 . . ?
C3D C4D H4D 108.3 . . ?
C5D C4D C3D 110.3(5) . . ?
C5D C4D H4D 108.3 . . ?
C14D C4D C3D 110.3(5) . . ?
C14D C4D H4D 108.3 . . ?
C14D C4D C5D 111.3(5) . . ?
C1D C5D C4D 112.2(5) . . ?
C1D C5D H5D 108.5 . . ?
C1D C5D C6D 109.4(4) . . ?
C4D C5D H5D 108.5 . . ?
C4D C5D C6D 109.7(5) . . ?
C6D C5D H5D 108.5 . . ?
O1D C6D C5D 108.7(4) . . ?
O1D C6D H6DA 110.0 . . ?
O1D C6D H6DB 110.0 . . ?
C5D C6D H6DA 110.0 . . ?
C5D C6D H6DB 110.0 . . ?
H6DA C6D H6DB 108.3 . . ?
O1D C7D C8D 123.9(5) . . ?
O1D C7D C12D 114.2(5) . . ?
C8D C7D C12D 121.9(5) . . ?
C7D C8D H8D 119.8 . . ?
C7D C8D C9D 120.3(6) . . ?
C9D C8D H8D 119.8 . . ?
C8D C9D H9D 121.5 . . ?
C10D C9D C8D 116.9(6) . . ?
C10D C9D H9D 121.5 . . ?
C9D C10D O2D 128.1(6) . . ?
C9D C10D C11D 122.2(6) . . ?
C11D C10D O2D 109.7(6) . . ?
O3D C11D C10D 110.7(6) . . ?
O3D C11D C12D 127.0(5) . . ?
C12D C11D C10D 122.2(6) . . ?
C7D C12D H12D 121.8 . . ?
C11D C12D C7D 116.4(5) . . ?
C11D C12D H12D 121.8 . . ?
O2D C13D H13G 110.1 . . ?
O2D C13D H13H 110.1 . . ?
O3D C13D O2D 107.9(5) . . ?
O3D C13D H13G 110.1 . . ?
O3D C13D H13H 110.1 . . ?
H13G C13D H13H 108.4 . . ?
C15D C14D C4D 120.8(6) . . ?
C15D C14D C19D 119.0(6) . . ?
C19D C14D C4D 120.2(6) . . ?
C14D C15D H15D 119.8 . . ?
C16D C15D C14D 120.4(7) . . ?
C16D C15D H15D 119.8 . . ?
C15D C16D H16D 120.8 . . ?
C15D C16D C17D 118.5(7) . . ?
C17D C16D H16D 120.8 . . ?
C16D C17D F1D 118.7(8) . . ?
C18D C17D C16D 123.4(7) . . ?
C18D C17D F1D 117.9(8) . . ?
C17D C18D H18D 121.1 . . ?
C17D C18D C19D 117.8(7) . . ?
C19D C18D H18D 121.1 . . ?
C14D C19D H19D 119.6 . . ?
C18D C19D C14D 120.8(6) . . ?
C18D C19D H19D 119.6 . . ?
O4D C20D O5D 123.7(6) . . ?
O4D C20D C21D 115.2(5) . . ?
O5D C20D C21D 121.1(5) . . ?
C20D C21D H21D 115.3 . . ?
C22D C21D C20D 129.4(5) . . ?
C22D C21D H21D 115.3 . . ?
C21D C22D H22D 115.3 . . ?
C21D C22D C23D 129.4(5) . . ?
C23D C22D H22D 115.3 . . ?
O6D C23D C22D 121.2(5) . . ?
O7D C23D O6D 122.6(6) . . ?
O7D C23D C22D 116.2(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1A C1A C5A C4A -51.2(6) . . . . ?
N1A C1A C5A C6A -172.0(4) . . . . ?
N1A C2A C3A C4A 57.3(6) . . . . ?
O1A C7A C8A C9A -176.6(6) . . . . ?
O1A C7A C12A C11A 176.1(5) . . . . ?
O2A C10A C11A O3A -0.5(10) . . . . ?
O2A C10A C11A C12A -177.3(7) . . . . ?
O3A C11A C12A C7A -175.0(7) . . . . ?
O4A C20A C21A C22A -177.2(6) . . . . ?
O5A C20A C21A C22A 1.6(10) . . . . ?
C1A N1A C2A C3A -57.0(7) . . . . ?
C1A C5A C6A O1A -70.0(5) . . . . ?
C2A N1A C1A C5A 54.0(6) . . . . ?
C2A C3A C4A C5A -55.4(6) . . . . ?
C2A C3A C4A C14A -178.2(5) . . . . ?
C3A C4A C5A C1A 51.7(6) . . . . ?
C3A C4A C5A C6A 173.4(5) . . . . ?
C3A C4A C14A C15A 60.5(7) . . . . ?
C3A C4A C14A C19A -122.4(6) . . . . ?
C4A C5A C6A O1A 167.4(4) . . . . ?
C4A C14A C15A C16A 177.4(5) . . . . ?
C4A C14A C19A C18A -178.2(6) . . . . ?
C5A C4A C14A C15A -61.3(6) . . . . ?
C5A C4A C14A C19A 115.7(6) . . . . ?
C6A O1A C7A C8A 7.0(8) . . . . ?
C6A O1A C7A C12A -171.8(5) . . . . ?
C7A O1A C6A C5A 174.9(4) . . . . ?
C7A C8A C9A C10A 0.2(11) . . . . ?
C8A C7A C12A C11A -2.8(9) . . . . ?
C8A C9A C10A O2A 176.2(8) . . . . ?
C8A C9A C10A C11A -1.8(12) . . . . ?
C9A C10A C11A O3A 177.8(7) . . . . ?
C9A C10A C11A C12A 1.1(12) . . . . ?
C10A O2A C13A O3A 10.9(10) . . . . ?
C10A C11A C12A C7A 1.2(10) . . . . ?
C11A O3A C13A O2A -11.1(9) . . . . ?
C12A C7A C8A C9A 2.2(10) . . . . ?
C13A O2A C10A C9A 175.4(9) . . . . ?
C13A O2A C10A C11A -6.5(10) . . . . ?
C13A O3A C11A C10A 7.2(9) . . . . ?
C13A O3A C11A C12A -176.3(8) . . . . ?
C14A C4A C5A C1A 173.8(4) . . . . ?
C14A C4A C5A C6A -64.4(6) . . . . ?
C14A C15A C16A C17A -1.9(9) . . . . ?
C15A C14A C19A C18A -1.2(10) . . . . ?
C15A C16A C17A C18A 4.5(10) . . . . ?
C15A C16A C17A F1A 178.4(6) . . . . ?
C16A C17A C18A C19A -5.2(11) . . . . ?
C17A C18A C19A C14A 3.4(11) . . . . ?
C19A C14A C15A C16A 0.3(8) . . . . ?
C20A C21A C22A C23A -4.7(11) . . . . ?
C21A C22A C23A O6A 4.1(10) . . . . ?
C21A C22A C23A O7A -174.6(6) . . . . ?
F1A C17A C18A C19A -179.3(6) . . . . ?
N1B C1B C5B C4B -53.0(6) . . . . ?
N1B C1B C5B C6B -174.4(4) . . . . ?
N1B C2B C3B C4B 57.6(7) . . . . ?
O1B C7B C8B C9B -176.4(6) . . . . ?
O1B C7B C12B C11B 176.4(5) . . . . ?
O2B C10B C11B O3B -0.7(9) . . . . ?
O2B C10B C11B C12B -177.8(7) . . . . ?
O3B C11B C12B C7B -175.8(6) . . . . ?
O4B C20B C21B C22B -179.4(6) . . . . ?
O5B C20B C21B C22B 1.1(10) . . . . ?
C1B N1B C2B C3B -58.0(7) . . . . ?
C1B C5B C6B O1B -68.9(6) . . . . ?
C2B N1B C1B C5B 55.6(6) . . . . ?
C2B C3B C4B C5B -55.9(6) . . . . ?
C2B C3B C4B C14B 179.9(5) . . . . ?
C3B C4B C5B C1B 52.7(6) . . . . ?
C3B C4B C5B C6B 174.4(4) . . . . ?
C3B C4B C14B C15B -114.5(6) . . . . ?
C3B C4B C14B C19B 66.9(7) . . . . ?
C4B C5B C6B O1B 168.4(4) . . . . ?
C4B C14B C15B C16B -179.2(6) . . . . ?
C4B C14B C19B C18B 178.2(6) . . . . ?
C5B C4B C14B C15B 122.6(6) . . . . ?
C5B C4B C14B C19B -56.1(7) . . . . ?
C6B O1B C7B C8B 6.9(8) . . . . ?
C6B O1B C7B C12B -172.1(5) . . . . ?
C7B O1B C6B C5B 174.7(4) . . . . ?
C7B C8B C9B C10B -0.6(11) . . . . ?
C8B C7B C12B C11B -2.6(8) . . . . ?
C8B C9B C10B O2B 177.5(8) . . . . ?
C8B C9B C10B C11B -1.1(12) . . . . ?
C9B C10B C11B O3B 178.1(7) . . . . ?
C9B C10B C11B C12B 1.0(11) . . . . ?
C10B O2B C13B O3B 9.6(10) . . . . ?
C10B C11B C12B C7B 0.8(9) . . . . ?
C11B O3B C13B O2B -10.0(9) . . . . ?
C12B C7B C8B C9B 2.5(10) . . . . ?
C13B O2B C10B C9B 175.6(9) . . . . ?
C13B O2B C10B C11B -5.7(10) . . . . ?
C13B O3B C11B C10B 6.6(8) . . . . ?
C13B O3B C11B C12B -176.4(6) . . . . ?
C14B C4B C5B C1B 175.9(5) . . . . ?
C14B C4B C5B C6B -62.4(6) . . . . ?
C14B C15B C16B C17B 1.9(11) . . . . ?
C15B C14B C19B C18B -0.5(9) . . . . ?
C15B C16B C17B C18B -2.3(12) . . . . ?
C15B C16B C17B F1B 179.4(7) . . . . ?
C16B C17B C18B C19B 1.3(11) . . . . ?
C17B C18B C19B C14B 0.2(10) . . . . ?
C19B C14B C15B C16B -0.6(10) . . . . ?
C20B C21B C22B C23B -3.3(11) . . . . ?
C21B C22B C23B O6B 2.0(9) . . . . ?
C21B C22B C23B O7B -178.3(6) . . . . ?
F1B C17B C18B C19B 179.6(7) . . . . ?
N1C C1C C5C C4C -51.2(6) . . . . ?
N1C C1C C5C C6C -171.7(4) . . . . ?
N1C C2C C3C C4C 57.0(7) . . . . ?
O1C C7C C8C C9C -179.5(6) . . . . ?
O1C C7C C12C C11C 176.3(5) . . . . ?
O2C C10C C11C O3C 1.0(10) . . . . ?
O2C C10C C11C C12C -179.5(7) . . . . ?
O3C C11C C12C C7C -176.4(6) . . . . ?
O4C C20C C21C C22C -177.2(6) . . . . ?
O5C C20C C21C C22C 2.3(10) . . . . ?
C1C N1C C2C C3C -57.7(6) . . . . ?
C1C C5C C6C O1C -68.4(6) . . . . ?
C2C N1C C1C C5C 54.9(6) . . . . ?
C2C C3C C4C C5C -52.9(7) . . . . ?
C2C C3C C4C C14C -176.4(5) . . . . ?
C3C C4C C5C C1C 50.0(6) . . . . ?
C3C C4C C5C C6C 171.2(5) . . . . ?
C3C C4C C14C C15C -127.2(6) . . . . ?
C3C C4C C14C C19C 55.8(7) . . . . ?
C4C C5C C6C O1C 168.3(4) . . . . ?
C4C C14C C15C C16C -177.2(6) . . . . ?
C4C C14C C19C C18C 177.7(5) . . . . ?
C5C C4C C14C C15C 109.6(6) . . . . ?
C5C C4C C14C C19C -67.3(6) . . . . ?
C6C O1C C7C C8C 4.7(8) . . . . ?
C6C O1C C7C C12C -174.6(5) . . . . ?
C7C O1C C6C C5C 178.7(4) . . . . ?
C7C C8C C9C C10C 2.5(11) . . . . ?
C8C C7C C12C C11C -3.0(9) . . . . ?
C8C C9C C10C O2C 175.6(8) . . . . ?
C8C C9C C10C C11C -1.4(12) . . . . ?
C9C C10C C11C O3C 178.5(8) . . . . ?
C9C C10C C11C C12C -2.0(12) . . . . ?
C10C O2C C13C O3C 6.5(11) . . . . ?
C10C C11C C12C C7C 4.1(10) . . . . ?
C11C O3C C13C O2C -6.0(10) . . . . ?
C12C C7C C8C C9C -0.3(10) . . . . ?
C13C O2C C10C C9C 178.1(9) . . . . ?
C13C O2C C10C C11C -4.6(10) . . . . ?
C13C O3C C11C C10C 3.1(9) . . . . ?
C13C O3C C11C C12C -176.3(7) . . . . ?
C14C C4C C5C C1C 173.8(5) . . . . ?
C14C C4C C5C C6C -64.9(6) . . . . ?
C14C C15C C16C C17C 0.4(11) . . . . ?
C15C C14C C19C C18C 0.6(9) . . . . ?
C15C C16C C17C C18C -1.0(11) . . . . ?
C15C C16C C17C F1C 179.7(7) . . . . ?
C16C C17C C18C C19C 1.4(10) . . . . ?
C17C C18C C19C C14C -1.2(9) . . . . ?
C19C C14C C15C C16C -0.2(10) . . . . ?
C20C C21C C22C C23C -7.1(10) . . . . ?
C21C C22C C23C O6C 7.0(10) . . . . ?
C21C C22C C23C O7C -173.5(6) . . . . ?
F1C C17C C18C C19C -179.3(6) . . . . ?
N1D C1D C5D C4D -52.1(6) . . . . ?
N1D C1D C5D C6D -174.0(5) . . . . ?
N1D C2D C3D C4D 58.0(6) . . . . ?
O1D C7D C8D C9D -177.2(6) . . . . ?
O1D C7D C12D C11D 177.2(5) . . . . ?
O2D C10D C11D O3D -0.1(9) . . . . ?
O2D C10D C11D C12D -177.3(7) . . . . ?
O3D C11D C12D C7D -176.7(6) . . . . ?
O4D C20D C21D C22D 179.7(6) . . . . ?
O5D C20D C21D C22D -1.2(10) . . . . ?
C1D N1D C2D C3D -58.5(6) . . . . ?
C1D C5D C6D O1D -67.9(6) . . . . ?
C2D N1D C1D C5D 55.5(6) . . . . ?
C2D C3D C4D C5D -55.5(7) . . . . ?
C2D C3D C4D C14D -178.9(5) . . . . ?
C3D C4D C5D C1D 51.8(6) . . . . ?
C3D C4D C5D C6D 173.5(5) . . . . ?
C3D C4D C14D C15D -115.4(6) . . . . ?
C3D C4D C14D C19D 63.4(7) . . . . ?
C4D C5D C6D O1D 168.7(4) . . . . ?
C4D C14D C15D C16D -177.3(7) . . . . ?
C4D C14D C19D C18D 178.9(6) . . . . ?
C5D C4D C14D C15D 121.7(6) . . . . ?
C5D C4D C14D C19D -59.5(7) . . . . ?
C6D O1D C7D C8D 4.9(8) . . . . ?
C6D O1D C7D C12D -173.7(5) . . . . ?
C7D O1D C6D C5D 176.4(5) . . . . ?
C7D C8D C9D C10D 0.2(11) . . . . ?
C8D C7D C12D C11D -1.5(9) . . . . ?
C8D C9D C10D O2D 177.0(8) . . . . ?
C8D C9D C10D C11D -1.6(12) . . . . ?
C9D C10D C11D O3D 178.7(7) . . . . ?
C9D C10D C11D C12D 1.5(12) . . . . ?
C10D O2D C13D O3D 5.2(10) . . . . ?
C10D C11D C12D C7D 0.1(10) . . . . ?
C11D O3D C13D O2D -5.3(9) . . . . ?
C12D C7D C8D C9D 1.3(10) . . . . ?
C13D O2D C10D C9D 178.1(9) . . . . ?
C13D O2D C10D C11D -3.2(10) . . . . ?
C13D O3D C11D C10D 3.4(8) . . . . ?
C13D O3D C11D C12D -179.5(7) . . . . ?
C14D C4D C5D C1D 174.6(5) . . . . ?
C14D C4D C5D C6D -63.6(6) . . . . ?
C14D C15D C16D C17D -4.1(12) . . . . ?
C15D C14D C19D C18D -2.3(10) . . . . ?
C15D C16D C17D C18D 2.9(13) . . . . ?
C15D C16D C17D F1D -178.1(7) . . . . ?
C16D C17D C18D C19D -1.3(11) . . . . ?
C17D C18D C19D C14D 1.0(10) . . . . ?
C19D C14D C15D C16D 3.9(10) . . . . ?
C20D C21D C22D C23D -0.4(10) . . . . ?
C21D C22D C23D O6D -1.0(9) . . . . ?
C21D C22D C23D O7D -179.6(6) . . . . ?
F1D C17D C18D C19D 179.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7444(18)
2 0.2556(18)

