# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_023TB220_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1877765'
_audit_update_record             
;
2018-11-08 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Fentanyl citrate hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '8(C22 H29 N2 O), 8(C6 H7 O7), 9(H2 O)'
_chemical_formula_sum            'C224 H306 N16 O74'
_chemical_formula_weight         4406.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   34.603(2)
_cell_length_b                   9.5694(6)
_cell_length_c                   20.2633(12)
_cell_angle_alpha                90
_cell_angle_beta                 120.599(2)
_cell_angle_gamma                90
_cell_volume                     5775.4(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9527
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      30.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             2354
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.302
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6425
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            109161
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         30.607
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8854
_reflns_number_gt                6575
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+5.4221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8854
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.33991(4) 0.78241(11) 0.67511(6) 0.0309(2) Uani 1 1 d . . . . .
N1 N 0.37106(3) 0.67218(11) 0.61494(6) 0.0186(2) Uani 1 1 d . . . . .
N2 N 0.26251(3) 0.46826(10) 0.42109(6) 0.01357(19) Uani 1 1 d . . . . .
H2 H 0.284536 0.390962 0.432868 0.016 Uiso 1 1 calc R U . . .
C1 C 0.41977(11) 0.8225(3) 0.81074(15) 0.0441(7) Uani 0.75 1 d . . P A 1
H1A H 0.400234 0.904868 0.794618 0.053 Uiso 0.75 1 calc R U P A 1
H1B H 0.450324 0.849655 0.849854 0.053 Uiso 0.75 1 calc R U P A 1
H1C H 0.408448 0.752566 0.832062 0.053 Uiso 0.75 1 calc R U P A 1
C1' C 0.4307(4) 0.8779(11) 0.7918(7) 0.073(4) Uani 0.25 1 d . . P A 2
H1A' H 0.462372 0.873372 0.832314 0.088 Uiso 0.25 1 calc R U P A 2
H1B' H 0.425403 0.963568 0.761835 0.088 Uiso 0.25 1 calc R U P A 2
H1C' H 0.411794 0.878208 0.814907 0.088 Uiso 0.25 1 calc R U P A 2
C2 C 0.42024(6) 0.7630(3) 0.74424(11) 0.0566(6) Uani 1 1 d . . . . .
H2A H 0.436518 0.672867 0.759329 0.068 Uiso 0.75 1 calc R U P A 1
H2B H 0.436903 0.826965 0.729134 0.068 Uiso 0.75 1 calc R U P A 1
H2A' H 0.427714 0.679282 0.777225 0.068 Uiso 0.25 1 calc R U P A 2
H2B' H 0.441215 0.763961 0.724576 0.068 Uiso 0.25 1 calc R U P A 2
C3 C 0.37384(5) 0.73931(15) 0.67593(8) 0.0268(3) Uani 1 1 d . . . . .
C4 C 0.40978(4) 0.61075(14) 0.61745(8) 0.0214(3) Uani 1 1 d . . . . .
C5 C 0.43246(5) 0.68414(17) 0.58845(9) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.423085 0.775401 0.568028 0.035 Uiso 1 1 calc R U . . .
C6 C 0.46920(5) 0.6218(2) 0.58980(10) 0.0418(4) Uani 1 1 d . . . . .
H6 H 0.484933 0.670532 0.569819 0.050 Uiso 1 1 calc R U . . .
C7 C 0.46036(6) 0.41749(19) 0.64906(10) 0.0414(4) Uani 1 1 d . . . . .
H7 H 0.470138 0.326783 0.670078 0.050 Uiso 1 1 calc R U . . .
C8 C 0.42333(5) 0.47727(15) 0.64772(8) 0.0288(3) Uani 1 1 d . . . . .
H8 H 0.407500 0.427590 0.667214 0.035 Uiso 1 1 calc R U . . .
C9 C 0.32606(4) 0.64771(12) 0.54701(7) 0.0164(2) Uani 1 1 d . . . . .
H9 H 0.307149 0.732015 0.539403 0.020 Uiso 1 1 calc R U . . .
C10 C 0.48291(5) 0.4895(2) 0.61998(11) 0.0456(5) Uani 1 1 d . . . . .
H10 H 0.508050 0.447871 0.620705 0.055 Uiso 1 1 calc R U . . .
C11 C 0.32817(4) 0.62576(13) 0.47449(7) 0.0188(2) Uani 1 1 d . . . . .
H11A H 0.340882 0.710010 0.464215 0.023 Uiso 1 1 calc R U . . .
H11B H 0.348078 0.545703 0.481729 0.023 Uiso 1 1 calc R U . . .
C12 C 0.28151(4) 0.59758(13) 0.40666(7) 0.0178(2) Uani 1 1 d . . . . .
H12A H 0.261678 0.678164 0.398878 0.021 Uiso 1 1 calc R U . . .
H12B H 0.283123 0.585487 0.359600 0.021 Uiso 1 1 calc R U . . .
C13 C 0.25828(4) 0.48897(13) 0.49046(7) 0.0177(2) Uani 1 1 d . . . . .
H13A H 0.245923 0.403188 0.500109 0.021 Uiso 1 1 calc R U . . .
H13B H 0.237200 0.566661 0.481098 0.021 Uiso 1 1 calc R U . . .
C14 C 0.30367(4) 0.52197(13) 0.56034(7) 0.0185(2) Uani 1 1 d . . . . .
H14A H 0.323496 0.439458 0.573210 0.022 Uiso 1 1 calc R U . . .
H14B H 0.299708 0.541315 0.604540 0.022 Uiso 1 1 calc R U . . .
C15 C 0.21926(4) 0.42624(12) 0.35132(7) 0.0160(2) Uani 1 1 d . . . . .
H15A H 0.222438 0.433216 0.305566 0.019 Uiso 1 1 calc R U . . .
H15B H 0.195145 0.491108 0.344231 0.019 Uiso 1 1 calc R U . . .
C16 C 0.20620(4) 0.27711(12) 0.35850(7) 0.0182(2) Uani 1 1 d . . . . .
H16A H 0.232099 0.214233 0.373508 0.022 Uiso 1 1 calc R U . . .
H16B H 0.198442 0.273394 0.399224 0.022 Uiso 1 1 calc R U . . .
C17 C 0.16669(4) 0.22722(13) 0.28386(7) 0.0191(2) Uani 1 1 d . . . . .
C18 C 0.17147(5) 0.11977(15) 0.24222(8) 0.0254(3) Uani 1 1 d . . . . .
H18 H 0.199707 0.074724 0.262013 0.030 Uiso 1 1 calc R U . . .
C19 C 0.13549(6) 0.07754(17) 0.17212(9) 0.0329(3) Uani 1 1 d . . . . .
H19 H 0.139230 0.003955 0.144377 0.039 Uiso 1 1 calc R U . . .
C20 C 0.09435(6) 0.14241(19) 0.14275(9) 0.0370(4) Uani 1 1 d . . . . .
H20 H 0.069926 0.115197 0.094240 0.044 Uiso 1 1 calc R U . . .
C21 C 0.08880(5) 0.2471(2) 0.18419(10) 0.0385(4) Uani 1 1 d . . . . .
H21 H 0.060334 0.290586 0.164531 0.046 Uiso 1 1 calc R U . . .
C22 C 0.12467(5) 0.28905(16) 0.25448(9) 0.0286(3) Uani 1 1 d . . . . .
H22 H 0.120480 0.360608 0.282739 0.034 Uiso 1 1 calc R U . . .
O2 O 0.48474(3) 0.17118(11) 0.51629(7) 0.0343(3) Uani 1 1 d . . . . .
H2C H 0.5088(6) 0.1165(13) 0.5170(10) 0.041 Uiso 1 1 calc R U . . .
O3 O 0.44931(3) -0.03452(11) 0.48345(7) 0.0315(2) Uani 1 1 d . . . . .
O4 O 0.37988(4) 0.00860(12) 0.53544(6) 0.0303(2) Uani 1 1 d . . . . .
H4O H 0.365571 0.036412 0.556218 0.036 Uiso 1 1 calc R U . . .
O5 O 0.28601(3) -0.13307(10) 0.31124(5) 0.0237(2) Uani 1 1 d . . . . .
H50 H 0.2587(6) -0.1625(16) 0.2976(6) 0.028 Uiso 1 1 calc R U . . .
O6 O 0.28156(3) -0.03459(11) 0.40668(6) 0.0293(2) Uani 1 1 d . . . . .
O7 O 0.32694(4) 0.21636(12) 0.51568(6) 0.0323(2) Uani 1 1 d . . . . .
O8 O 0.31824(3) 0.28218(10) 0.40330(6) 0.0274(2) Uani 1 1 d . . . . .
C23 C 0.44917(4) 0.09086(15) 0.49417(8) 0.0250(3) Uani 1 1 d . . . . .
C24 C 0.40925(4) 0.17347(14) 0.48204(9) 0.0261(3) Uani 1 1 d . . . . .
H24A H 0.399785 0.234810 0.437008 0.031 Uiso 1 1 calc R U . . .
H24B H 0.419008 0.234868 0.527134 0.031 Uiso 1 1 calc R U . . .
C25 C 0.36809(4) 0.09136(13) 0.46956(7) 0.0188(2) Uani 1 1 d . . . . .
C26 C 0.34820(4) -0.00161(12) 0.39840(7) 0.0165(2) Uani 1 1 d . . . . .
H26A H 0.346793 0.052287 0.355529 0.020 Uiso 1 1 calc R U . . .
H26B H 0.368517 -0.082011 0.408775 0.020 Uiso 1 1 calc R U . . .
C27 C 0.30189(4) -0.05607(12) 0.37393(7) 0.0160(2) Uani 1 1 d . . . . .
C28 C 0.33430(4) 0.20513(13) 0.46185(8) 0.0216(3) Uani 1 1 d . . . . .
O1W O 0.29297(4) 0.25618(13) 0.25288(7) 0.0336(3) Uani 1 1 d . . . . .
H1WA H 0.3101(8) 0.259(2) 0.2373(13) 0.051(7) Uiso 1 1 d . . . . .
H1WB H 0.3072(7) 0.263(2) 0.3044(14) 0.051(6) Uiso 1 1 d . . . . .
O2W O 0.0226(5) 0.4620(19) 0.3343(7) 0.084(5) Uani 0.125 1 d . . P . .


_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 C3 1.2365(17) . ?
N1 C3 1.3522(17) . ?
N1 C4 1.4401(16) . ?
N1 C9 1.4806(16) . ?
N2 C13 1.4984(15) . ?
N2 C12 1.4984(15) . ?
N2 C15 1.4987(15) . ?
N2 H2 1.0000 . ?
C1 C2 1.470(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1' C2 1.383(10) . ?
C1' H1A' 0.9800 . ?
C1' H1B' 0.9800 . ?
C1' H1C' 0.9800 . ?
C2 C3 1.511(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 H2A' 0.9900 . ?
C2 H2B' 0.9900 . ?
C4 C5 1.387(2) . ?
C4 C8 1.391(2) . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 C10 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C10 1.378(3) . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C11 1.5224(17) . ?
C9 C14 1.5279(17) . ?
C9 H9 1.0000 . ?
C10 H10 0.9500 . ?
C11 C12 1.5198(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5189(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5259(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5097(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.3919(19) . ?
C17 C18 1.3923(19) . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O2 C23 1.3209(17) . ?
O2 H2C 0.98(2) . ?
O3 C23 1.2198(17) . ?
O4 C25 1.4218(17) . ?
O4 H4O 0.8400 . ?
O5 C27 1.3220(15) . ?
O5 H50 0.885(19) . ?
O6 C27 1.2053(15) . ?
O7 C28 1.2445(17) . ?
O8 C28 1.2605(18) . ?
C23 C24 1.4994(17) . ?
C24 C25 1.5308(18) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5278(17) . ?
C25 C28 1.5462(16) . ?
C26 C27 1.5085(16) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
O1W H1WA 0.80(2) . ?
O1W H1WB 0.90(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
C3 N1 C4 121.97(11) . . ?
C3 N1 C9 118.47(10) . . ?
C4 N1 C9 119.18(10) . . ?
C13 N2 C12 109.62(9) . . ?
C13 N2 C15 113.15(9) . . ?
C12 N2 C15 111.35(9) . . ?
C13 N2 H2 107.5 . . ?
C12 N2 H2 107.5 . . ?
C15 N2 H2 107.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1' H1A' 109.5 . . ?
C2 C1' H1B' 109.5 . . ?
H1A' C1' H1B' 109.5 . . ?
C2 C1' H1C' 109.5 . . ?
H1A' C1' H1C' 109.5 . . ?
H1B' C1' H1C' 109.5 . . ?
C1' C2 C3 122.5(5) . . ?
C1 C2 C3 113.30(18) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C1' C2 H2A' 106.7 . . ?
C3 C2 H2A' 106.7 . . ?
C1' C2 H2B' 106.7 . . ?
C3 C2 H2B' 106.7 . . ?
H2A' C2 H2B' 106.6 . . ?
O1 C3 N1 121.38(13) . . ?
O1 C3 C2 121.41(13) . . ?
N1 C3 C2 117.19(13) . . ?
C5 C4 C8 121.02(13) . . ?
C5 C4 N1 119.68(12) . . ?
C8 C4 N1 119.29(13) . . ?
C4 C5 C6 118.85(16) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C10 C6 C5 120.42(17) . . ?
C10 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C10 C7 C8 120.16(16) . . ?
C10 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C4 119.13(16) . . ?
C7 C8 H8 120.4 . . ?
C4 C8 H8 120.4 . . ?
N1 C9 C11 112.00(10) . . ?
N1 C9 C14 110.38(10) . . ?
C11 C9 C14 109.87(10) . . ?
N1 C9 H9 108.2 . . ?
C11 C9 H9 108.2 . . ?
C14 C9 H9 108.2 . . ?
C7 C10 C6 120.41(15) . . ?
C7 C10 H10 119.8 . . ?
C6 C10 H10 119.8 . . ?
C12 C11 C9 110.27(10) . . ?
C12 C11 H11A 109.6 . . ?
C9 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C9 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C11 109.86(10) . . ?
N2 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N2 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 C14 110.72(10) . . ?
N2 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C9 112.06(10) . . ?
C13 C14 H14A 109.2 . . ?
C9 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C9 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C16 111.28(9) . . ?
N2 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N2 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 111.19(10) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C22 C17 C18 118.37(13) . . ?
C22 C17 C16 120.68(12) . . ?
C18 C17 C16 120.95(12) . . ?
C19 C18 C17 120.89(14) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.05(15) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.74(14) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.29(15) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.62(15) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C23 O2 H2C 109.5 . . ?
C25 O4 H4O 109.5 . . ?
C27 O5 H50 109.5 . . ?
O3 C23 O2 123.05(12) . . ?
O3 C23 C24 125.19(12) . . ?
O2 C23 C24 111.74(12) . . ?
C23 C24 C25 117.30(11) . . ?
C23 C24 H24A 108.0 . . ?
C25 C24 H24A 108.0 . . ?
C23 C24 H24B 108.0 . . ?
C25 C24 H24B 108.0 . . ?
H24A C24 H24B 107.2 . . ?
O4 C25 C26 109.75(10) . . ?
O4 C25 C24 109.42(11) . . ?
C26 C25 C24 112.90(10) . . ?
O4 C25 C28 109.15(10) . . ?
C26 C25 C28 111.13(10) . . ?
C24 C25 C28 104.32(10) . . ?
C27 C26 C25 113.84(10) . . ?
C27 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
O6 C27 O5 123.39(12) . . ?
O6 C27 C26 125.45(11) . . ?
O5 C27 C26 111.16(10) . . ?
O7 C28 O8 125.84(12) . . ?
O7 C28 C25 116.99(12) . . ?
O8 C28 C25 117.08(11) . . ?
H1WA O1W H1WB 112(2) . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_mo_023VB214_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1877768'
_audit_update_record             
;
2018-11-08 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Fentanyl citrate toluene solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H29 N2 O, C6 H7 O7, C7 H8'
_chemical_formula_sum            'C35 H44 N2 O8'
_chemical_formula_weight         620.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.9040(12)
_cell_length_b                   9.6858(6)
_cell_length_c                   19.3593(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.125(3)
_cell_angle_gamma                90
_cell_volume                     3190.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.93

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61126
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.376
_diffrn_reflns_theta_max         28.008
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7638
_reflns_number_gt                6103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0768P)²+2.4348P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7638
_refine_ls_number_parameters     414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.18746(8) 0.73218(15) 0.23128(7) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.46956(8) 0.78890(13) 0.45003(7) 0.0107(3) Uani 1 1 d . . . . .
H1 H 0.461244 0.798984 0.498518 0.013 Uiso 1 1 calc R U . . .
N2 N 0.21876(8) 0.76319(14) 0.35313(7) 0.0130(3) Uani 1 1 d . . . . .
C1 C 0.85284(10) 0.73271(17) 0.57307(10) 0.0189(3) Uani 1 1 d . . . . .
H1A H 0.908336 0.741003 0.585589 0.023 Uiso 1 1 calc R U . . .
C2 C 0.81713(10) 0.73120(18) 0.62731(9) 0.0196(3) Uani 1 1 d . . . . .
H2 H 0.848107 0.738011 0.676912 0.023 Uiso 1 1 calc R U . . .
C3 C 0.73565(10) 0.71965(17) 0.60867(9) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.711293 0.719117 0.645815 0.021 Uiso 1 1 calc R U . . .
C4 C 0.68956(9) 0.70890(16) 0.53625(9) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.72647(10) 0.71004(17) 0.48236(9) 0.0171(3) Uani 1 1 d . . . . .
H5 H 0.695787 0.702488 0.432713 0.021 Uiso 1 1 calc R U . . .
C6 C 0.80775(10) 0.72215(17) 0.50082(10) 0.0181(3) Uani 1 1 d . . . . .
H6 H 0.832311 0.723168 0.463826 0.022 Uiso 1 1 calc R U . . .
C7 C 0.60166(9) 0.68989(18) 0.51679(9) 0.0167(3) Uani 1 1 d . . . . .
H7A H 0.586015 0.698437 0.561356 0.020 Uiso 1 1 calc R U . . .
H7B H 0.587658 0.595756 0.497082 0.020 Uiso 1 1 calc R U . . .
C8 C 0.55618(9) 0.79494(16) 0.46111(8) 0.0131(3) Uani 1 1 d . . . . .
H8A H 0.575734 0.888753 0.477536 0.016 Uiso 1 1 calc R U . . .
H8B H 0.565741 0.777440 0.414182 0.016 Uiso 1 1 calc R U . . .
C9 C 0.42808(9) 0.90559(15) 0.40260(8) 0.0124(3) Uani 1 1 d . . . . .
H9A H 0.435099 0.896945 0.354033 0.015 Uiso 1 1 calc R U . . .
H9B H 0.451557 0.994364 0.424073 0.015 Uiso 1 1 calc R U . . .
C10 C 0.34078(9) 0.90527(16) 0.39460(8) 0.0135(3) Uani 1 1 d . . . . .
H10A H 0.314461 0.982089 0.362474 0.016 Uiso 1 1 calc R U . . .
H10B H 0.333517 0.919399 0.442747 0.016 Uiso 1 1 calc R U . . .
C11 C 0.30372(9) 0.76844(15) 0.36252(8) 0.0122(3) Uani 1 1 d . . . . .
H11 H 0.310409 0.758704 0.313354 0.015 Uiso 1 1 calc R U . . .
C12 C 0.34724(9) 0.64919(15) 0.40930(9) 0.0132(3) Uani 1 1 d . . . . .
H12A H 0.339883 0.654229 0.457848 0.016 Uiso 1 1 calc R U . . .
H12B H 0.324926 0.560565 0.386617 0.016 Uiso 1 1 calc R U . . .
C13 C 0.43460(9) 0.65375(15) 0.41775(8) 0.0124(3) Uani 1 1 d . . . . .
H13A H 0.461748 0.577136 0.449581 0.015 Uiso 1 1 calc R U . . .
H13B H 0.442288 0.641473 0.369649 0.015 Uiso 1 1 calc R U . . .
C14 C 0.19445(9) 0.77062(16) 0.41734(8) 0.0133(3) Uani 1 1 d . . . . .
C15 C 0.18113(10) 0.89856(17) 0.44379(9) 0.0177(3) Uani 1 1 d . . . . .
H15 H 0.186505 0.980616 0.418871 0.021 Uiso 1 1 calc R U . . .
C16 C 0.15988(10) 0.90583(18) 0.50699(10) 0.0208(4) Uani 1 1 d . . . . .
H16 H 0.150555 0.993181 0.525066 0.025 Uiso 1 1 calc R U . . .
C17 C 0.15223(10) 0.78666(19) 0.54373(9) 0.0201(3) Uani 1 1 d . . . . .
H17 H 0.138581 0.792253 0.587298 0.024 Uiso 1 1 calc R U . . .
C18 C 0.16462(9) 0.65888(18) 0.51657(9) 0.0183(3) Uani 1 1 d . . . . .
H18 H 0.158342 0.576840 0.541087 0.022 Uiso 1 1 calc R U . . .
C19 C 0.18617(9) 0.65070(17) 0.45362(9) 0.0152(3) Uani 1 1 d . . . . .
H19 H 0.195214 0.563262 0.435462 0.018 Uiso 1 1 calc R U . . .
C20 C 0.16660(10) 0.74349(18) 0.28563(9) 0.0171(3) Uani 1 1 d . . . . .
C21 C 0.07978(10) 0.7401(2) 0.27944(10) 0.0239(4) Uani 1 1 d . . . . .
H21A H 0.074282 0.718346 0.327591 0.029 Uiso 1 1 calc R U . . .
H21B H 0.056648 0.832470 0.264751 0.029 Uiso 1 1 calc R U . . .
C22 C 0.03502(11) 0.6342(2) 0.22476(11) 0.0290(4) Uani 1 1 d . . . . .
H22A H 0.039473 0.656328 0.176797 0.044 Uiso 1 1 calc R U . . .
H22B H -0.020447 0.635373 0.222405 0.044 Uiso 1 1 calc R U . . .
H22C H 0.057037 0.542271 0.239632 0.044 Uiso 1 1 calc R U . . .
O2 O 0.43644(7) 0.77061(12) 0.75630(6) 0.0119(2) Uani 1 1 d . . . . .
H2A H 0.4779(13) 0.727(2) 0.76263(19) 0.018 Uiso 1 1 calc R U . . .
O3 O 0.43315(8) 0.47830(13) 0.64287(7) 0.0232(3) Uani 1 1 d . . . . .
O4 O 0.38084(7) 0.46901(12) 0.73423(6) 0.0187(3) Uani 1 1 d . . . . .
H4 H 0.4161(13) 0.402(3) 0.7506(8) 0.028 Uiso 1 1 calc R U . . .
O5 O 0.52844(6) 0.78372(11) 0.67075(6) 0.0133(2) Uani 1 1 d . . . . .
O6 O 0.42686(7) 0.82335(13) 0.57082(6) 0.0167(2) Uani 1 1 d . . . . .
O7 O 0.44535(7) 1.08141(12) 0.69203(6) 0.0173(2) Uani 1 1 d . . . . .
O8 O 0.37688(7) 1.07496(12) 0.77059(6) 0.0159(2) Uani 1 1 d . . . . .
H8 H 0.4114(12) 1.143(2) 0.7927(9) 0.024 Uiso 1 1 calc R U . . .
C23 C 0.34390(9) 0.65637(16) 0.65279(8) 0.0129(3) Uani 1 1 d . . . . .
H23A H 0.299589 0.656868 0.673182 0.015 Uiso 1 1 calc R U . . .
H23B H 0.321926 0.660916 0.599170 0.015 Uiso 1 1 calc R U . . .
C24 C 0.39703(9) 0.78315(15) 0.68107(8) 0.0103(3) Uani 1 1 d . . . . .
C25 C 0.34448(9) 0.91151(16) 0.67353(8) 0.0124(3) Uani 1 1 d . . . . .
H25A H 0.320206 0.934453 0.621508 0.015 Uiso 1 1 calc R U . . .
H25B H 0.301901 0.892795 0.694844 0.015 Uiso 1 1 calc R U . . .
C26 C 0.39071(9) 0.52501(16) 0.67464(9) 0.0143(3) Uani 1 1 d . . . . .
C27 C 0.45615(9) 0.79867(15) 0.63719(8) 0.0116(3) Uani 1 1 d . . . . .
C28 C 0.39370(9) 1.03056(15) 0.71233(8) 0.0121(3) Uani 1 1 d . . . . .
C29 C 0.17002(13) 0.1549(2) 0.67182(12) 0.0343(5) Uani 1 1 d . . . . .
H29 H 0.200278 0.073277 0.686279 0.041 Uiso 1 1 calc R U . . .
C30 C 0.20341(12) 0.2827(2) 0.69378(11) 0.0321(5) Uani 1 1 d . . . . .
H30 H 0.257191 0.289165 0.722023 0.039 Uiso 1 1 calc R U . . .
C31 C 0.15838(11) 0.4014(2) 0.67457(10) 0.0253(4) Uani 1 1 d . . . . .
H31 H 0.181373 0.488804 0.690585 0.030 Uiso 1 1 calc R U . . .
C32 C 0.07989(10) 0.39398(18) 0.63208(9) 0.0196(3) Uani 1 1 d . . . . .
C33 C 0.04768(11) 0.26495(19) 0.60854(10) 0.0226(4) Uani 1 1 d . . . . .
H33 H -0.005382 0.258114 0.578394 0.027 Uiso 1 1 calc R U . . .
C34 C 0.09255(13) 0.1464(2) 0.62881(11) 0.0294(4) Uani 1 1 d . . . . .
H34 H 0.069837 0.058717 0.613003 0.035 Uiso 1 1 calc R U . . .
C35 C 0.03004(13) 0.5215(2) 0.61246(12) 0.0319(4) Uani 1 1 d . . . . .
H35A H 0.006843 0.526890 0.559534 0.048 Uiso 1 1 calc R U . . .
H35B H 0.062680 0.603251 0.630053 0.048 Uiso 1 1 calc R U . . .
H35C H -0.011927 0.517616 0.635003 0.048 Uiso 1 1 calc R U . . .


_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 1.226(2) . ?
N1 C8 1.499(2) . ?
N1 C9 1.4992(19) . ?
N1 C13 1.5008(18) . ?
N1 H1 1.0000 . ?
N2 C20 1.363(2) . ?
N2 C14 1.4408(19) . ?
N2 C11 1.476(2) . ?
C1 C6 1.384(3) . ?
C1 C2 1.389(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.394(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 C7 1.511(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.525(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.522(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.389(2) . ?
C14 C15 1.390(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.522(2) . ?
C21 C22 1.512(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O2 C24 1.4123(17) . ?
O2 H2A 0.83(2) . ?
O3 C26 1.205(2) . ?
O4 C26 1.335(2) . ?
O4 H4 0.89(2) . ?
O5 C27 1.2630(19) . ?
O6 C27 1.2505(19) . ?
O7 C28 1.2160(19) . ?
O8 C28 1.3262(18) . ?
O8 H8 0.91(2) . ?
C23 C26 1.510(2) . ?
C23 C24 1.545(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.538(2) . ?
C24 C27 1.557(2) . ?
C25 C28 1.503(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C29 C34 1.380(3) . ?
C29 C30 1.383(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.387(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.392(3) . ?
C32 C35 1.502(3) . ?
C33 C34 1.386(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 110.58(11) . . ?
C8 N1 C13 111.87(11) . . ?
C9 N1 C13 109.86(12) . . ?
C8 N1 H1 108.1 . . ?
C9 N1 H1 108.1 . . ?
C13 N1 H1 108.1 . . ?
C20 N2 C14 122.25(13) . . ?
C20 N2 C11 119.70(13) . . ?
C14 N2 C11 117.93(12) . . ?
C6 C1 C2 120.14(16) . . ?
C6 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 C3 119.72(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.77(15) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.77(15) . . ?
C3 C4 C7 120.36(14) . . ?
C5 C4 C7 120.82(14) . . ?
C6 C5 C4 120.57(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 120.03(15) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C7 C8 112.43(13) . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 112.16(12) . . ?
N1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 110.98(12) . . ?
N1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 110.26(12) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C12 111.34(12) . . ?
N2 C11 C10 112.42(12) . . ?
C12 C11 C10 109.84(13) . . ?
N2 C11 H11 107.7 . . ?
C12 C11 H11 107.7 . . ?
C10 C11 H11 107.7 . . ?
C13 C12 C11 111.12(12) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N1 C13 C12 110.59(12) . . ?
N1 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C19 C14 C15 120.12(15) . . ?
C19 C14 N2 120.20(14) . . ?
C15 C14 N2 119.67(14) . . ?
C14 C15 C16 119.63(15) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.48(16) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.69(15) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.20(16) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 119.87(15) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
O1 C20 N2 122.33(15) . . ?
O1 C20 C21 120.44(15) . . ?
N2 C20 C21 117.20(14) . . ?
C22 C21 C20 112.08(15) . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 O2 H2A 109.5 . . ?
C26 O4 H4 109.5 . . ?
C28 O8 H8 109.5 . . ?
C26 C23 C24 110.09(12) . . ?
C26 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
C26 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.2 . . ?
O2 C24 C25 105.19(12) . . ?
O2 C24 C23 110.61(12) . . ?
C25 C24 C23 108.52(12) . . ?
O2 C24 C27 111.38(12) . . ?
C25 C24 C27 111.69(12) . . ?
C23 C24 C27 109.36(12) . . ?
C28 C25 C24 109.06(12) . . ?
C28 C25 H25A 109.9 . . ?
C24 C25 H25A 109.9 . . ?
C28 C25 H25B 109.9 . . ?
C24 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
O3 C26 O4 124.23(15) . . ?
O3 C26 C23 123.83(15) . . ?
O4 C26 C23 111.92(13) . . ?
O6 C27 O5 125.84(14) . . ?
O6 C27 C24 116.11(13) . . ?
O5 C27 C24 118.04(13) . . ?
O7 C28 O8 122.70(14) . . ?
O7 C28 C25 122.40(14) . . ?
O8 C28 C25 114.90(13) . . ?
C34 C29 C30 119.75(18) . . ?
C34 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C29 C30 C31 120.00(19) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C32 120.74(19) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C31 C32 C33 118.63(17) . . ?
C31 C32 C35 121.21(18) . . ?
C33 C32 C35 120.16(17) . . ?
C34 C33 C32 120.42(18) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C29 C34 C33 120.42(19) . . ?
C29 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_mo_023VB133_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1877766'
_audit_update_record             
;
2018-11-08 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Fentanyl citrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H29 N2 O, C6 H7 O7'
_chemical_formula_sum            'C28 H36 N2 O8'
_chemical_formula_weight         528.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9630(5)
_cell_length_b                   11.2533(7)
_cell_length_c                   14.8740(9)
_cell_angle_alpha                109.411(2)
_cell_angle_beta                 96.728(2)
_cell_angle_gamma                107.486(2)
_cell_volume                     1309.72(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      30.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            84871
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.455
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8025
_reflns_number_gt                6758
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+0.5033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8025
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.66211(9) 0.74419(7) 0.74241(6) 0.01507(15) Uani 1 1 d . . . . .
N1 N 0.42775(10) 0.65093(8) 0.77852(6) 0.01114(15) Uani 1 1 d . . . . .
N2 N 0.13778(10) 0.30135(8) 0.51860(6) 0.01019(15) Uani 1 1 d . . . . .
H2 H 0.039484 0.302994 0.543822 0.012 Uiso 1 1 calc R U . . .
C1 C 0.57902(16) 0.98640(11) 0.87681(9) 0.0260(2) Uani 1 1 d . . . . .
H1A H 0.624152 1.003442 0.823437 0.039 Uiso 1 1 calc R U . . .
H1B H 0.623989 1.068868 0.936796 0.039 Uiso 1 1 calc R U . . .
H1C H 0.461556 0.959487 0.858665 0.039 Uiso 1 1 calc R U . . .
C2 C 0.62167(12) 0.87318(10) 0.89478(8) 0.01626(19) Uani 1 1 d . . . . .
H2A H 0.739264 0.904977 0.922035 0.020 Uiso 1 1 calc R U . . .
H2B H 0.566059 0.848798 0.943368 0.020 Uiso 1 1 calc R U . . .
C3 C 0.57200(11) 0.75038(10) 0.80019(7) 0.01197(17) Uani 1 1 d . . . . .
C4 C 0.32462(11) 0.65400(10) 0.84590(7) 0.01119(17) Uani 1 1 d . . . . .
H4O H 0.504(2) 0.1744(19) 0.6237(14) 0.040(5) Uiso 1 1 d . . . . .
C5 C 0.33792(12) 0.59351(10) 0.91279(7) 0.01497(19) Uani 1 1 d . . . . .
H5 H 0.416065 0.552529 0.914815 0.018 Uiso 1 1 calc R U . . .
C6 C 0.23640(13) 0.59336(11) 0.97655(8) 0.0179(2) Uani 1 1 d . . . . .
H6 H 0.244657 0.551869 1.022133 0.021 Uiso 1 1 calc R U . . .
C7 C 0.12249(13) 0.65407(11) 0.97360(8) 0.0177(2) Uani 1 1 d . . . . .
H7 H 0.052598 0.653413 1.016914 0.021 Uiso 1 1 calc R U . . .
C8 C 0.11085(12) 0.71555(11) 0.90752(7) 0.01609(19) Uani 1 1 d . . . . .
H8 H 0.034066 0.757991 0.906301 0.019 Uiso 1 1 calc R U . . .
C9 C 0.21155(12) 0.71507(10) 0.84307(7) 0.01329(18) Uani 1 1 d . . . . .
H9 H 0.203000 0.756301 0.797347 0.016 Uiso 1 1 calc R U . . .
C10 C 0.37354(11) 0.53446(10) 0.68315(7) 0.01117(17) Uani 1 1 d . . . . .
H10 H 0.470873 0.531925 0.657020 0.013 Uiso 1 1 calc R U . . .
C11 C 0.25737(12) 0.55021(10) 0.60840(7) 0.01421(18) Uani 1 1 d . . . . .
H11A H 0.308257 0.636973 0.601621 0.017 Uiso 1 1 calc R U . . .
H11B H 0.158660 0.551789 0.631678 0.017 Uiso 1 1 calc R U . . .
C12 C 0.21273(12) 0.43373(10) 0.50892(7) 0.01444(18) Uani 1 1 d . . . . .
H12A H 0.135832 0.444250 0.461349 0.017 Uiso 1 1 calc R U . . .
H12B H 0.310530 0.435114 0.483834 0.017 Uiso 1 1 calc R U . . .
C13 C 0.25129(12) 0.28546(10) 0.59242(7) 0.01368(18) Uani 1 1 d . . . . .
H13A H 0.349982 0.283703 0.569167 0.016 Uiso 1 1 calc R U . . .
H13B H 0.199759 0.198259 0.598449 0.016 Uiso 1 1 calc R U . . .
C14 C 0.29695(12) 0.39991(10) 0.69239(7) 0.01266(17) Uani 1 1 d . . . . .
H14A H 0.373902 0.388109 0.739098 0.015 Uiso 1 1 calc R U . . .
H14B H 0.199641 0.398660 0.718014 0.015 Uiso 1 1 calc R U . . .
C15 C 0.08643(12) 0.18135(10) 0.42311(7) 0.01366(18) Uani 1 1 d . . . . .
H15A H 0.053116 0.097743 0.436275 0.016 Uiso 1 1 calc R U . . .
H15B H 0.179680 0.183711 0.393118 0.016 Uiso 1 1 calc R U . . .
C16 C -0.05207(12) 0.17662(10) 0.35041(7) 0.01549(19) Uani 1 1 d . . . . .
H16A H -0.140072 0.187808 0.382899 0.019 Uiso 1 1 calc R U . . .
H16B H -0.014372 0.251600 0.327957 0.019 Uiso 1 1 calc R U . . .
C17 C -0.11425(11) 0.04282(10) 0.26318(7) 0.01274(18) Uani 1 1 d . . . . .
C18 C -0.26193(12) -0.05617(11) 0.25079(8) 0.0166(2) Uani 1 1 d . . . . .
H18 H -0.324669 -0.039426 0.297494 0.020 Uiso 1 1 calc R U . . .
C19 C -0.31807(13) -0.17924(11) 0.17055(8) 0.0201(2) Uani 1 1 d . . . . .
H19 H -0.419147 -0.245714 0.162507 0.024 Uiso 1 1 calc R U . . .
C20 C -0.22682(14) -0.20514(11) 0.10223(8) 0.0216(2) Uani 1 1 d . . . . .
H20 H -0.264966 -0.289161 0.047491 0.026 Uiso 1 1 calc R U . . .
C21 C -0.07955(15) -0.10738(12) 0.11453(8) 0.0227(2) Uani 1 1 d . . . . .
H21 H -0.016739 -0.124782 0.067970 0.027 Uiso 1 1 calc R U . . .
C22 C -0.02298(13) 0.01588(11) 0.19439(8) 0.0185(2) Uani 1 1 d . . . . .
H22 H 0.078205 0.082016 0.202158 0.022 Uiso 1 1 calc R U . . .
O2 O 0.69914(10) 0.53823(8) 0.85056(6) 0.01882(16) Uani 1 1 d . . . . .
O3 O 0.78466(9) 0.55456(8) 0.71796(5) 0.01600(15) Uani 1 1 d . . . . .
H3 H 0.7454(18) 0.6180(16) 0.7291(7) 0.024 Uiso 1 1 calc R U . . .
O4 O 0.56390(9) 0.22314(8) 0.68154(6) 0.01392(14) Uani 1 1 d . . . . .
O5 O 0.58633(10) -0.06622(8) 0.61723(6) 0.01824(16) Uani 1 1 d . . . . .
H5A H 0.5174(18) -0.1384(16) 0.5658(10) 0.027 Uiso 1 1 calc R U . . .
O6 O 0.68112(10) -0.00669(8) 0.49947(6) 0.01801(16) Uani 1 1 d . . . . .
O7 O 0.61264(9) 0.27919(7) 0.52570(5) 0.01711(15) Uani 1 1 d . . . . .
O8 O 0.87982(9) 0.34088(8) 0.56994(6) 0.01803(16) Uani 1 1 d . . . . .
C23 C 0.76187(12) 0.49953(10) 0.78415(7) 0.01278(18) Uani 1 1 d . . . . .
C24 C 0.82426(12) 0.38551(10) 0.76734(7) 0.01392(18) Uani 1 1 d . . . . .
H24A H 0.821496 0.358284 0.824121 0.017 Uiso 1 1 calc R U . . .
H24B H 0.937913 0.417786 0.763257 0.017 Uiso 1 1 calc R U . . .
C25 C 0.72559(11) 0.26223(9) 0.67322(7) 0.01044(17) Uani 1 1 d . . . . .
C26 C 0.79090(12) 0.14802(10) 0.66787(8) 0.01454(18) Uani 1 1 d . . . . .
H26A H 0.900759 0.173129 0.656626 0.017 Uiso 1 1 calc R U . . .
H26B H 0.797514 0.136026 0.731021 0.017 Uiso 1 1 calc R U . . .
C27 C 0.68180(12) 0.01721(10) 0.58564(7) 0.01340(18) Uani 1 1 d . . . . .
C28 C 0.74069(12) 0.29669(9) 0.58119(7) 0.01129(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
O1 C3 1.2459(12) . ?
N1 C3 1.3495(12) . ?
N1 C4 1.4399(12) . ?
N1 C10 1.4786(12) . ?
N2 C13 1.5002(12) . ?
N2 C15 1.5004(12) . ?
N2 C12 1.5017(12) . ?
N2 H2 1.0000 . ?
C1 C2 1.5284(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5094(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C9 1.3888(14) . ?
C4 C5 1.3924(14) . ?
C5 C6 1.3892(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3927(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3881(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3913(14) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C14 1.5227(13) . ?
C10 C11 1.5239(13) . ?
C10 H10 1.0000 . ?
C11 C12 1.5247(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5183(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5233(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5129(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.3952(14) . ?
C17 C18 1.3955(14) . ?
C18 C19 1.3919(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.3884(17) . ?
C19 H19 0.9500 . ?
C20 C21 1.3868(16) . ?
C20 H20 0.9500 . ?
C21 C22 1.3904(15) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O2 C23 1.2136(12) . ?
O3 C23 1.3308(12) . ?
O3 H3 0.864(16) . ?
O4 C25 1.4157(11) . ?
O4 H4O 0.855(19) . ?
O5 C27 1.3187(12) . ?
O5 H5A 0.896(17) . ?
O6 C27 1.2179(13) . ?
O7 C28 1.2536(12) . ?
O8 C28 1.2497(12) . ?
C23 C24 1.5074(14) . ?
C24 C25 1.5325(13) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5480(13) . ?
C25 C28 1.5514(13) . ?
C26 C27 1.5089(14) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C4 121.99(8) . . ?
C3 N1 C10 119.36(8) . . ?
C4 N1 C10 118.64(7) . . ?
C13 N2 C15 109.77(7) . . ?
C13 N2 C12 110.31(8) . . ?
C15 N2 C12 113.41(7) . . ?
C13 N2 H2 107.7 . . ?
C15 N2 H2 107.7 . . ?
C12 N2 H2 107.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 110.47(9) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 N1 121.22(9) . . ?
O1 C3 C2 119.74(9) . . ?
N1 C3 C2 119.01(8) . . ?
C9 C4 C5 120.47(9) . . ?
C9 C4 N1 120.19(9) . . ?
C5 C4 N1 119.33(9) . . ?
C6 C5 C4 119.69(10) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 119.95(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.15(9) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.06(10) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 119.67(9) . . ?
C4 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N1 C10 C14 112.77(8) . . ?
N1 C10 C11 111.60(8) . . ?
C14 C10 C11 109.74(8) . . ?
N1 C10 H10 107.5 . . ?
C14 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C10 C11 C12 110.43(8) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C11 110.05(8) . . ?
N2 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 C14 111.52(8) . . ?
N2 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C10 109.52(8) . . ?
C13 C14 H14A 109.8 . . ?
C10 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C10 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
N2 C15 C16 112.99(8) . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 109.81(8) . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C22 C17 C18 118.92(9) . . ?
C22 C17 C16 120.21(9) . . ?
C18 C17 C16 120.86(9) . . ?
C19 C18 C17 120.54(10) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.21(10) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.46(10) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 120.61(10) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 120.26(10) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C23 O3 H3 109.5 . . ?
C25 O4 H4O 107.4(12) . . ?
C27 O5 H5A 109.5 . . ?
O2 C23 O3 123.40(9) . . ?
O2 C23 C24 124.41(9) . . ?
O3 C23 C24 112.18(8) . . ?
C23 C24 C25 112.42(8) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
O4 C25 C24 106.75(7) . . ?
O4 C25 C26 110.18(8) . . ?
C24 C25 C26 107.98(8) . . ?
O4 C25 C28 111.36(8) . . ?
C24 C25 C28 110.89(8) . . ?
C26 C25 C28 109.59(8) . . ?
C27 C26 C25 110.33(8) . . ?
C27 C26 H26A 109.6 . . ?
C25 C26 H26A 109.6 . . ?
C27 C26 H26B 109.6 . . ?
C25 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
O6 C27 O5 124.14(10) . . ?
O6 C27 C26 123.11(9) . . ?
O5 C27 C26 112.74(9) . . ?
O8 C28 O7 126.06(9) . . ?
O8 C28 C25 116.85(9) . . ?
O7 C28 C25 117.08(8) . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.051

