# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Q_DH
_database_code_depnum_ccdc_archive 'CCDC 1051731'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_audit_creation_date             2014-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            'Quifenadine hydrochloride dihydrate DH'
_chemical_name_systematic        
'1-azabicyclo[2.2.2]oct-8-yl-diphenyl-methanol hydrochloride dihydrate'
_chemical_formula_moiety         'C20 H24 N O, Cl, 2(H2 O)'
_chemical_formula_sum            'C20 H28 Cl N O3'
_chemical_formula_weight         365.88
_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'
Cl Cl 0.1484 0.1585 '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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.33880(10)
_cell_length_b                   8.6008(2)
_cell_length_c                   18.404(5)
_cell_angle_alpha                100.0241(11)
_cell_angle_beta                 92.3170(11)
_cell_angle_gamma                103.4511(12)
_cell_volume                     957.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8094
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.007
_diffrn_reflns_theta_min         2.255
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3235
_reflns_number_total             4630
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      0.929
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1484
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B), O2(H2A,H2B)
2.b Ternary CH refined with riding coordinates:
 N3(H3), C8(H8), C10(H10)
2.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C21(H21), C24(H24)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Cl24 Cl 0.37551(8) 0.05221(6) 0.13017(3) 0.03401(17) Uani 1 1 d . . . . .
O25 O 0.7044(2) 0.20385(18) 0.02114(9) 0.0424(4) Uani 1 1 d . . . . .
H48 H 0.6269 0.1634 0.0531 0.064 Uiso 1 1 d G . . . .
H49 H 0.6841 0.1349 -0.0192 0.064 Uiso 1 1 d G . . . .
O5 O 0.47133(19) 0.87238(15) 0.26146(7) 0.0251(3) Uani 1 1 d . . . . .
H26 H 0.4650 0.9332 0.2322 0.038 Uiso 1 1 calc GR . . . .
N14 N 0.7804(2) 0.69282(18) 0.10033(8) 0.0259(3) Uani 1 1 d . . . . .
H37 H 0.7961 0.7238 0.0517 0.031 Uiso 1 1 calc R . . . .
C3 C 0.8016(3) 1.0806(2) 0.30772(9) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.6837(3) 1.1843(2) 0.34464(10) 0.0286(4) Uani 1 1 d . . . . .
H30 H 0.5415 1.1415 0.3547 0.034 Uiso 1 1 calc R . . . .
C1 C 0.6929(3) 0.8972(2) 0.28987(9) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.8160(3) 0.7994(2) 0.23545(9) 0.0223(4) Uani 1 1 d . . . . .
H25 H 0.9688 0.8297 0.2553 0.027 Uiso 1 1 calc R . . . .
C4 C 0.6865(3) 0.8347(2) 0.36339(9) 0.0226(4) Uani 1 1 d . . . . .
C6 C 0.7395(3) 0.6121(2) 0.22554(10) 0.0254(4) Uani 1 1 d . . . . .
H23 H 0.7238 0.5805 0.2741 0.030 Uiso 1 1 calc R . . . .
C17 C 0.8752(3) 0.7906(2) 0.47170(11) 0.0332(5) Uani 1 1 d . . . . .
H40 H 1.0053 0.7989 0.4990 0.040 Uiso 1 1 calc R . . . .
C8 C 1.0134(3) 1.1480(2) 0.29346(10) 0.0275(4) Uani 1 1 d . . . . .
H29 H 1.0950 1.0813 0.2692 0.033 Uiso 1 1 calc R . . . .
C21 C 0.9866(3) 1.4137(2) 0.35207(11) 0.0330(5) Uani 1 1 d . . . . .
H46 H 1.0490 1.5244 0.3674 0.040 Uiso 1 1 calc R . . . .
C10 C 0.8774(3) 0.8460(2) 0.40523(10) 0.0279(4) Uani 1 1 d . . . . .
H31 H 1.0099 0.8916 0.3885 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8113(3) 0.8434(2) 0.15784(10) 0.0263(4) Uani 1 1 d . . . . .
H28 H 0.6931 0.8953 0.1514 0.032 Uiso 1 1 calc R . . . .
H27 H 0.9468 0.9193 0.1526 0.032 Uiso 1 1 calc R . . . .
C12 C 0.5258(3) 0.5449(2) 0.17730(11) 0.0310(4) Uani 1 1 d . . . . .
H33 H 0.4143 0.5946 0.1986 0.037 Uiso 1 1 calc R . . . .
H32 H 0.4782 0.4282 0.1745 0.037 Uiso 1 1 calc R . . . .
C11 C 0.4903(3) 0.7671(2) 0.38953(11) 0.0308(4) Uani 1 1 d . . . . .
H34 H 0.3600 0.7591 0.3624 0.037 Uiso 1 1 calc R . . . .
C16 C 0.7751(3) 1.3493(2) 0.36635(11) 0.0325(4) Uani 1 1 d . . . . .
H39 H 0.6943 1.4168 0.3905 0.039 Uiso 1 1 calc R . . . .
C15 C 1.1051(3) 1.3144(2) 0.31511(11) 0.0324(4) Uani 1 1 d . . . . .
H38 H 1.2465 1.3584 0.3046 0.039 Uiso 1 1 calc R . . . .
C13 C 0.9139(3) 0.5404(2) 0.18654(11) 0.0314(4) Uani 1 1 d . . . . .
H36 H 1.0482 0.5711 0.2185 0.038 Uiso 1 1 calc R . . . .
H35 H 0.8663 0.4226 0.1757 0.038 Uiso 1 1 calc R . . . .
C22 C 0.6784(4) 0.7230(2) 0.49717(11) 0.0372(5) Uani 1 1 d . . . . .
H47 H 0.6754 0.6858 0.5417 0.045 Uiso 1 1 calc R . . . .
C19 C 0.5607(3) 0.5824(3) 0.09962(12) 0.0408(5) Uani 1 1 d . . . . .
H42 H 0.5490 0.4821 0.0644 0.049 Uiso 1 1 calc R . . . .
H43 H 0.4497 0.6340 0.0845 0.049 Uiso 1 1 calc R . . . .
C20 C 0.9521(3) 0.6051(3) 0.11482(11) 0.0364(5) Uani 1 1 d . . . . .
H45 H 1.0951 0.6790 0.1191 0.044 Uiso 1 1 calc R . . . .
H44 H 0.9457 0.5156 0.0740 0.044 Uiso 1 1 calc R . . . .
C18 C 0.4875(4) 0.7113(3) 0.45597(11) 0.0395(5) Uani 1 1 d . . . . .
H41 H 0.3552 0.6655 0.4728 0.047 Uiso 1 1 calc R . . . .
O26 O 0.8528(2) 0.73893(18) -0.04030(8) 0.0351(3) Uani 1 1 d . . . . .
H50 H 0.7954 0.7884 -0.0689 0.053 Uiso 1 1 d G . . . .
H51 H 0.9906 0.7709 -0.0384 0.053 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
O5 C1 1.433(2) . ?
N14 C7 1.491(2) . ?
N14 C19 1.490(3) . ?
N14 C20 1.501(2) . ?
C3 C9 1.399(3) . ?
C3 C1 1.539(2) . ?
C3 C8 1.388(3) . ?
C9 C16 1.382(3) . ?
C1 C2 1.548(2) . ?
C1 C4 1.539(2) . ?
C2 C6 1.545(2) . ?
C2 C7 1.541(2) . ?
C4 C10 1.382(3) . ?
C4 C11 1.388(3) . ?
C6 C12 1.523(3) . ?
C6 C13 1.531(3) . ?
C17 C10 1.387(3) . ?
C17 C22 1.385(3) . ?
C8 C15 1.393(3) . ?
C21 C16 1.381(3) . ?
C21 C15 1.377(3) . ?
C12 C19 1.533(3) . ?
C11 C18 1.388(3) . ?
C13 C20 1.526(3) . ?
C22 C18 1.376(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N14 C20 109.43(15) . . ?
C19 N14 C7 111.54(15) . . ?
C19 N14 C20 109.58(15) . . ?
C9 C3 C1 117.66(15) . . ?
C8 C3 C9 118.13(16) . . ?
C8 C3 C1 124.09(15) . . ?
C16 C9 C3 121.03(17) . . ?
O5 C1 C3 109.55(13) . . ?
O5 C1 C2 110.68(13) . . ?
O5 C1 C4 106.78(13) . . ?
C3 C1 C2 112.95(14) . . ?
C3 C1 C4 107.41(14) . . ?
C4 C1 C2 109.22(13) . . ?
C6 C2 C1 115.64(14) . . ?
C7 C2 C1 112.54(13) . . ?
C7 C2 C6 107.60(14) . . ?
C10 C4 C1 120.43(16) . . ?
C10 C4 C11 118.46(16) . . ?
C11 C4 C1 121.11(16) . . ?
C12 C6 C2 112.04(15) . . ?
C12 C6 C13 107.90(15) . . ?
C13 C6 C2 107.37(15) . . ?
C22 C17 C10 119.69(18) . . ?
C3 C8 C15 120.82(17) . . ?
C15 C21 C16 120.12(18) . . ?
C4 C10 C17 121.35(18) . . ?
N14 C7 C2 109.58(13) . . ?
C6 C12 C19 108.73(15) . . ?
C4 C11 C18 120.36(18) . . ?
C21 C16 C9 119.91(18) . . ?
C21 C15 C8 119.98(18) . . ?
C20 C13 C6 108.91(14) . . ?
C18 C22 C17 119.42(18) . . ?
N14 C19 C12 109.39(15) . . ?
N14 C20 C13 109.11(14) . . ?
C22 C18 C11 120.7(2) . . ?

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
O5 C1 C2 C6 -66.86(18) . . . . ?
O5 C1 C2 C7 57.36(18) . . . . ?
O5 C1 C4 C10 -178.42(15) . . . . ?
O5 C1 C4 C11 1.1(2) . . . . ?
C3 C9 C16 C21 -0.5(3) . . . . ?
C3 C1 C2 C6 169.88(14) . . . . ?
C3 C1 C2 C7 -65.90(18) . . . . ?
C3 C1 C4 C10 -61.0(2) . . . . ?
C3 C1 C4 C11 118.52(18) . . . . ?
C3 C8 C15 C21 0.9(3) . . . . ?
C9 C3 C1 O5 44.2(2) . . . . ?
C9 C3 C1 C2 168.08(15) . . . . ?
C9 C3 C1 C4 -71.43(19) . . . . ?
C9 C3 C8 C15 -0.3(3) . . . . ?
C1 C3 C9 C16 176.25(15) . . . . ?
C1 C3 C8 C15 -176.22(16) . . . . ?
C1 C2 C6 C12 75.81(19) . . . . ?
C1 C2 C6 C13 -165.89(14) . . . . ?
C1 C2 C7 N14 -140.13(14) . . . . ?
C1 C4 C10 C17 179.89(16) . . . . ?
C1 C4 C11 C18 -179.99(17) . . . . ?
C2 C1 C4 C10 61.9(2) . . . . ?
C2 C1 C4 C11 -118.66(18) . . . . ?
C2 C6 C12 C19 62.8(2) . . . . ?
C2 C6 C13 C20 -54.9(2) . . . . ?
C4 C1 C2 C6 50.42(19) . . . . ?
C4 C1 C2 C7 174.64(14) . . . . ?
C4 C11 C18 C22 0.5(3) . . . . ?
C6 C2 C7 N14 -11.58(19) . . . . ?
C6 C12 C19 N14 -8.5(2) . . . . ?
C6 C13 C20 N14 -9.7(2) . . . . ?
C17 C22 C18 C11 -0.3(3) . . . . ?
C8 C3 C9 C16 0.0(3) . . . . ?
C8 C3 C1 O5 -139.82(16) . . . . ?
C8 C3 C1 C2 -15.9(2) . . . . ?
C8 C3 C1 C4 104.56(18) . . . . ?
C10 C4 C11 C18 -0.5(3) . . . . ?
C10 C17 C22 C18 0.2(3) . . . . ?
C7 N14 C19 C12 -55.1(2) . . . . ?
C7 N14 C20 C13 67.39(19) . . . . ?
C7 C2 C6 C12 -50.94(19) . . . . ?
C7 C2 C6 C13 67.36(17) . . . . ?
C12 C6 C13 C20 66.0(2) . . . . ?
C11 C4 C10 C17 0.4(3) . . . . ?
C16 C21 C15 C8 -1.4(3) . . . . ?
C15 C21 C16 C9 1.1(3) . . . . ?
C13 C6 C12 C19 -55.1(2) . . . . ?
C22 C17 C10 C4 -0.2(3) . . . . ?
C19 N14 C7 C2 67.15(18) . . . . ?
C19 N14 C20 C13 -55.2(2) . . . . ?
C20 N14 C7 C2 -54.27(18) . . . . ?
C20 N14 C19 C12 66.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile/water'
####################################################################### 
# 
# 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_Q_A
_database_code_depnum_ccdc_archive 'CCDC 1051732'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_audit_creation_date             2014-05-19
_audit_creation_method           'Materials Studio'

_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_hall  '-P 1'
_symmetry_Int_Tables_number      2
_symmetry_cell_setting           triclinic
_chemical_name_systematic        
'1-Azabicyclo[2.2.2]oct-3-yl(diphenyl)methanol hydrochloride'
_chemical_name_common            'Quifenadine hydrochloride form A'
_chemical_formula_moiety         'C20 H24 N O, Cl'
_chemical_formula_sum            'C20 H24 Cl N O'
_chemical_formula_weight         329.85
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
_cell_length_a                   6.3724(2)
_cell_length_b                   12.6985(5)
_cell_length_c                   10.7590(4)
_cell_angle_alpha                96.031(15)
_cell_angle_beta                 98.883(15)
_cell_angle_gamma                80.676(2)
_cell_volume                     845.94(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_ambient_temperature      293(2)

_pd_spec_mounting                capillary
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  white

_pd_meas_2theta_range_min        5.00
_pd_meas_2theta_range_max        70.00
_pd_meas_2theta_range_inc        0.01

_pd_proc_ls_profile_function     'Pseudo Voigt'
_pd_proc_ls_background_function  'linear extrapolation'

_pd_proc_ls_prof_R_factor        none
_pd_proc_ls_prof_wR_factor       none

_refine_ls_goodness_of_fit_all   none

_refine_ls_restrained_S_all      ?
_refine_ls_shift/su_max          ?
_refine_ls_shift/su_mean         ?

_refine_ls_R_factor_all          none

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
C1 C -0.17755(26) 0.78682(19) 0.22867(14) 0.01267 Uiso 1
C2 C 0.03509(27) 0.77968(25) 0.32161(16) 0.01267 Uiso 1
C3 C -0.14994(30) 0.71554(15) 0.10647(17) 0.01267 Uiso 1
C4 C -0.25099(28) 0.90297(17) 0.19456(13) 0.01267 Uiso 1
O5 O -0.34044(27) 0.75632(21) 0.29013(19) 0.01267 Uiso 1
C6 C 0.03126(44) 0.85769(19) 0.44282(27) 0.01267 Uiso 1
C7 C 0.11671(47) 0.66558(23) 0.36443(22) 0.01267 Uiso 1
C8 C 0.03799(40) 0.70190(26) 0.05071(27) 0.01267 Uiso 1
C9 C -0.31712(38) 0.66354(24) 0.04441(25) 0.01267 Uiso 1
C10 C -0.10956(33) 0.96521(19) 0.16141(39) 0.01267 Uiso 1
C11 C -0.46511(33) 0.95043(20) 0.19492(36) 0.01267 Uiso 1
C12 C -0.10165(44) 0.82474(39) 0.53675(17 0.01267 Uiso 1
C13 C 0.26518(49) 0.85335(25) 0.50926(32) 0.01267 Uiso 1
N14 N 0.18153(56) 0.66815(22) 0.50458(23) 0.01267 Uiso 1
C15 C 0.05671(50) 0.64082(25) -0.06368(30 0.01267 Uiso 1
C16 C -0.30210(45) 0.60335(24) -0.07040(28) 0.01267 Uiso 1
C17 C -0.17807(37) 1.07013(18) 0.13146(40) 0.01267 Uiso 1
C18 C -0.53557(38) 1.05573(19) 0.16758(39 0.01267 Uiso 1
C19 C -0.00994(57) 0.71009(42) 0.57081(17) 0.01267 Uiso 1
C20 C 0.35028(42) 0.73895(25) 0.54612(21) 0.01267 Uiso 1
C21 C -0.11554(49) 0.59238(13) -0.12619(24 0.01267 Uiso 1
C22 C -0.39092(37) 1.11649(14) 0.13614(22) 0.01267 Uiso 1
H23 H -0.03165 0.93968 0.4171 0.0152 Uiso 1
Cl24 Cl -0.65573(50) 0.47818(22) 0.65642(28) 0.01267 Uiso 1
H25 H 0.16166 0.80085 0.27397 0.0152 Uiso 1
H26 H -0.32076 0.67855 0.28523 0.0152 Uiso 1
H27 H 0.25617 0.62882 0.31958 0.0152 Uiso 1
H28 H 0.00006 0.61018 0.34061 0.0152 Uiso 1
H29 H 0.17685 0.73967 0.09549 0.0152 Uiso 1
H30 H -0.46598 0.66971 0.086 0.0152 Uiso 1
H31 H 0.05847 0.9308 0.156 0.0152 Uiso 1
H32 H -0.58122 0.90288 0.2177 0.0152 Uiso 1
H33 H -0.27283 0.8311 0.49882 0.0152 Uiso 1
H34 H -0.09048 0.88035 0.62262 0.0152 Uiso 1
H35 H 0.27375 0.90992 0.59409 0.0152 Uiso 1
H36 H 0.36676 0.87698 0.44613 0.0152 Uiso 1
H37 H 0.24183 0.59265 0.52843 0.0152 Uiso 1
H38 H 0.2073 0.62931 -0.10487 0.0152 Uiso 1
H39 H -0.43726 0.563 -0.11621 0.0152 Uiso 1
H40 H -0.06474 1.11696 0.10362 0.0152 Uiso 1
H41 H -0.70458 1.09064 0.16849 0.0152 Uiso 1
H42 H -0.12591 0.65356 0.54436 0.0152 Uiso 1
H43 H 0.04596 0.70692 0.67267 0.0152 Uiso 1
H44 H 0.39298 0.73525 0.64894 0.0152 Uiso 1
H45 H 0.4928 0.70319 0.50256 0.0152 Uiso 1
H46 H -0.10198 0.5435 -0.2158 0.0152 Uiso 1
H47 H -0.4453 1.19951 0.11276 0.0152 Uiso 1

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_ccdc_geom_bond_type
C1 C2 1.551(3) . S
C1 C3 1.533(3) . S
C1 C4 1.538(3) . S
C1 O5 1.435(3) . S
C2 C6 1.553(4) . S
C2 C7 1.550(4) . S
C2 H25 1.101 . S
C3 C8 1.399(3) . D
C3 C9 1.391(3) . S
C4 C10 1.398(3) . D
C4 C11 1.400(3) . S
O5 H26 0.970 . S
C6 C12 1.544(4) . S
C6 C13 1.546(4) . S
C6 H23 1.101 . S
C7 N14 1.500(3) . S
C7 H27 1.092 . S
C7 H28 1.089 . S
C8 C15 1.395(4) . S
C8 H29 1.097 . S
C9 C16 1.390(4) . D
C9 H30 1.098 . S
C10 C17 1.388(4) . S
C10 H31 1.097 . S
C11 C18 1.387(4) . D
C11 H32 1.097 . S
C12 C19 1.538(7) . S
C12 H33 1.097 . S
C12 H34 1.103 . S
C13 C20 1.536(5) . S
C13 H35 1.100 . S
C13 H36 1.101 . S
N14 C19 1.502(5) . S
N14 C20 1.499(5) . S
N14 H37 1.017 . S
C15 C21 1.392(4) . D
C15 H38 1.101 . S
C16 C21 1.394(4) . S
C16 H39 1.099 . S
C17 C22 1.394(4) . D
C17 H40 1.100 . S
C18 C22 1.394(4) . S
C18 H41 1.097 . S
C19 H42 1.098 . S
C19 H43 1.102 . S
C20 H44 1.102 . S
C20 H45 1.097 . S
C21 H46 1.098 . S
C22 H47 1.098 . S
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C3 . . . 111.32(18)
C2 C1 C4 . . . 109.9(2)
C2 C1 O5 . . . 108.63(15)
C1 C2 C6 . . . 115.5(2)
C1 C2 C7 . . . 113.3(2)
C1 C2 H25 . . . 108.9
C3 C1 C4 . . . 108.31(13)
C3 C1 O5 . . . 110.77(18)
C1 C3 C8 . . . 122.6(2)
C1 C3 C9 . . . 120.22(19)
C4 C1 O5 . . . 107.83(18)
C1 C4 C10 . . . 122.08(18)
C1 C4 C11 . . . 120.70(19)
C1 O5 H26 . . . 107.6
C6 C2 C7 . . . 107.16(18)
C6 C2 H25 . . . 104.9
C2 C6 C12 . . . 112.5(2)
C2 C6 C13 . . . 107.4(2)
C2 C6 H23 . . . 109.8
C7 C2 H25 . . . 106.3
C2 C7 N14 . . . 111.31(19)
C2 C7 H27 . . . 110.6
C2 C7 H28 . . . 114.5
C8 C3 C9 . . . 117.2(2)
C3 C8 C15 . . . 121.8(3)
C3 C8 H29 . . . 120.9
C3 C9 C16 . . . 121.7(2)
C3 C9 H30 . . . 119.9
C10 C4 C11 . . . 117.2(2)
C4 C10 C17 . . . 121.4(2)
C4 C10 H31 . . . 120.1
C4 C11 C18 . . . 122.2(2)
C4 C11 H32 . . . 119.0
C12 C6 C13 . . . 107.4(2)
C12 C6 H23 . . . 110.2
C6 C12 C19 . . . 109.0(3)
C6 C12 H33 . . . 111.9
C6 C12 H34 . . . 108.8
C13 C6 H23 . . . 109.6
C6 C13 C20 . . . 109.1(3)
C6 C13 H35 . . . 110.8
C6 C13 H36 . . . 110.2
N14 C7 H27 . . . 107.9
N14 C7 H28 . . . 106.6
C7 N14 C19 . . . 110.0(3)
C7 N14 C20 . . . 110.6(2)
C7 N14 H37 . . . 109.0
H27 C7 H28 . . . 105.7
C15 C8 H29 . . . 117.3
C8 C15 C21 . . . 120.0(3)
C8 C15 H38 . . . 120.8
C16 C9 H30 . . . 118.4
C9 C16 C21 . . . 120.5(3)
C9 C16 H39 . . . 119.6
C17 C10 H31 . . . 118.5
C10 C17 C22 . . . 120.3(2)
C10 C17 H40 . . . 120.1
C18 C11 H32 . . . 118.8
C11 C18 C22 . . . 119.5(2)
C11 C18 H41 . . . 120.5
C19 C12 H33 . . . 111.1
C19 C12 H34 . . . 109.7
C12 C19 N14 . . . 110.2(3)
C12 C19 H42 . . . 113.2
C12 C19 H43 . . . 111.9
H33 C12 H34 . . . 106.3
C20 C13 H35 . . . 109.8
C20 C13 H36 . . . 110.0
C13 C20 N14 . . . 110.1(2)
C13 C20 H44 . . . 112.5
C13 C20 H45 . . . 112.5
H35 C13 H36 . . . 107.0
C19 N14 C20 . . . 108.8(2)
C19 N14 H37 . . . 109.5
N14 C19 H42 . . . 107.4
N14 C19 H43 . . . 106.6
C20 N14 H37 . . . 108.9
N14 C20 H44 . . . 106.6
N14 C20 H45 . . . 107.5
C21 C15 H38 . . . 119.3
C15 C21 C16 . . . 118.8(2)
C15 C21 H46 . . . 120.6
C21 C16 H39 . . . 120.0
C16 C21 H46 . . . 120.6
C22 C17 H40 . . . 119.7
C17 C22 C18 . . . 119.46(19)
C17 C22 H47 . . . 120.4
C22 C18 H41 . . . 120.1
C18 C22 H47 . . . 120.2
H42 C19 H43 . . . 107.3
H44 C20 H45 . . . 107.4


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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 C6 . . . . 174.0(2)
C3 C1 C2 C7 . . . . -61.9(2)
C3 C1 C2 H25 . . . . 56.2
C4 C1 C2 C6 . . . . 54.0(3)
C4 C1 C2 C7 . . . . 178.11(16)
C4 C1 C2 H25 . . . . -63.8
O5 C1 C2 C6 . . . . -63.8(3)
O5 C1 C2 C7 . . . . 60.4(2)
O5 C1 C2 H25 . . . . 178.5
C2 C1 C3 C8 . . . . -36.9(3)
C2 C1 C3 C9 . . . . 144.9(2)
C4 C1 C3 C8 . . . . 84.0(3)
C4 C1 C3 C9 . . . . -94.2(2)
O5 C1 C3 C8 . . . . -157.9(2)
O5 C1 C3 C9 . . . . 23.9(3)
C2 C1 C4 C10 . . . . 46.2(3)
C2 C1 C4 C11 . . . . -134.2(2)
C3 C1 C4 C10 . . . . -75.6(3)
C3 C1 C4 C11 . . . . 104.0(3)
O5 C1 C4 C10 . . . . 164.5(2)
O5 C1 C4 C11 . . . . -15.9(3)
C2 C1 O5 H26 . . . . -80.4
C3 C1 O5 H26 . . . . 42.2
C4 C1 O5 H26 . . . . 160.5
C1 C2 C6 C12 . . . . 72.5(3)
C1 C2 C6 C13 . . . . -169.6(2)
C1 C2 C6 H23 . . . . -50.6
C7 C2 C6 C12 . . . . -54.8(3)
C7 C2 C6 C13 . . . . 63.1(3)
C7 C2 C6 H23 . . . . -177.9
H25 C2 C6 C12 . . . . -167.6
H25 C2 C6 C13 . . . . -49.7
H25 C2 C6 H23 . . . . 69.4
C1 C2 C7 N14 . . . . -133.2(2)
C1 C2 C7 H27 . . . . 106.9
C1 C2 C7 H28 . . . . -12.3
C6 C2 C7 N14 . . . . -4.6(3)
C6 C2 C7 H27 . . . . -124.5
C6 C2 C7 H28 . . . . 116.3
H25 C2 C7 N14 . . . . 107.2
H25 C2 C7 H27 . . . . -12.7
H25 C2 C7 H28 . . . . -131.9
C1 C3 C8 C15 . . . . -176.9(3)
C1 C3 C8 H29 . . . . 2.7
C9 C3 C8 C15 . . . . 1.4(4)
C9 C3 C8 H29 . . . . -179.0
C1 C3 C9 C16 . . . . 176.1(2)
C1 C3 C9 H30 . . . . -3.6
C8 C3 C9 C16 . . . . -2.2(4)
C8 C3 C9 H30 . . . . 178.1
C1 C4 C10 C17 . . . . -179.7(3)
C1 C4 C10 H31 . . . . 2.0
C11 C4 C10 C17 . . . . 0.8(5)
C11 C4 C10 H31 . . . . -177.6
C1 C4 C11 C18 . . . . 178.4(3)
C1 C4 C11 H32 . . . . -1.4
C10 C4 C11 C18 . . . . -2.0(5)
C10 C4 C11 H32 . . . . 178.2
C2 C6 C12 C19 . . . . 57.2(3)
C2 C6 C12 H33 . . . . -66.0
C2 C6 C12 H34 . . . . 176.9
C13 C6 C12 C19 . . . . -60.7(3)
C13 C6 C12 H33 . . . . 176.0
C13 C6 C12 H34 . . . . 58.9
H23 C6 C12 C19 . . . . -180
H23 C6 C12 H33 . . . . 56.8
H23 C6 C12 H34 . . . . -60.4
C2 C6 C13 C20 . . . . -61.5(3)
C2 C6 C13 H35 . . . . 177.5
C2 C6 C13 H36 . . . . 59.3
C12 C6 C13 C20 . . . . 59.6(3)
C12 C6 C13 H35 . . . . -61.3
C12 C6 C13 H36 . . . . -179.6
H23 C6 C13 C20 . . . . 179.3
H23 C6 C13 H35 . . . . 58.4
H23 C6 C13 H36 . . . . -59.9
C2 C7 N14 C19 . . . . 63.1(3)
C2 C7 N14 C20 . . . . -57.2(3)
C2 C7 N14 H37 . . . . -176.8
H27 C7 N14 C19 . . . . -175.5
H27 C7 N14 C20 . . . . 64.3
H27 C7 N14 H37 . . . . -55.4
H28 C7 N14 C19 . . . . -62.3
H28 C7 N14 C20 . . . . 177.4
H28 C7 N14 H37 . . . . 57.7
C3 C8 C15 C21 . . . . 0.7(5)
C3 C8 C15 H38 . . . . -178.4
H29 C8 C15 C21 . . . . -178.9
H29 C8 C15 H38 . . . . 2.0
C3 C9 C16 C21 . . . . 0.9(4)
C3 C9 C16 H39 . . . . 179.6
H30 C9 C16 C21 . . . . -179.4
H30 C9 C16 H39 . . . . -0.7
C4 C10 C17 C22 . . . . 1.1(6)
C4 C10 C17 H40 . . . . -178.6
H31 C10 C17 C22 . . . . 179.4
H31 C10 C17 H40 . . . . -0.3
C4 C11 C18 C22 . . . . 1.4(6)
C4 C11 C18 H41 . . . . 179.9
H32 C11 C18 C22 . . . . -178.8
H32 C11 C18 H41 . . . . -0.2
C6 C12 C19 N14 . . . . 1.3(3)
C6 C12 C19 H42 . . . . -118.9
C6 C12 C19 H43 . . . . 119.7
H33 C12 C19 N14 . . . . 125.0
H33 C12 C19 H42 . . . . 4.8
H33 C12 C19 H43 . . . . -116.6
H34 C12 C19 N14 . . . . -117.8
H34 C12 C19 H42 . . . . 122.0
H34 C12 C19 H43 . . . . 0.6
C6 C13 C20 N14 . . . . 0.7(3)
C6 C13 C20 H44 . . . . -118.0
C6 C13 C20 H45 . . . . 120.6
H35 C13 C20 N14 . . . . 122.3
H35 C13 C20 H44 . . . . 3.5
H35 C13 C20 H45 . . . . -117.9
H36 C13 C20 N14 . . . . -120.2
H36 C13 C20 H44 . . . . 121.1
H36 C13 C20 H45 . . . . -0.4
C7 N14 C19 C12 . . . . -60.8(3)
C7 N14 C19 H42 . . . . 62.9
C7 N14 C19 H43 . . . . 177.7
C20 N14 C19 C12 . . . . 60.5(3)
C20 N14 C19 H42 . . . . -175.8
C20 N14 C19 H43 . . . . -61.1
H37 N14 C19 C12 . . . . 179.5
H37 N14 C19 H42 . . . . -56.8
H37 N14 C19 H43 . . . . 57.9
C7 N14 C20 C13 . . . . 59.3(3)
C7 N14 C20 H44 . . . . -178.5
C7 N14 C20 H45 . . . . -63.6
C19 N14 C20 C13 . . . . -61.7(3)
C19 N14 C20 H44 . . . . 60.6
C19 N14 C20 H45 . . . . 175.5
H37 N14 C20 C13 . . . . 179.0
H37 N14 C20 H44 . . . . -58.7
H37 N14 C20 H45 . . . . 56.1
C8 C15 C21 C16 . . . . -2.0(4)
C8 C15 C21 H46 . . . . -179.4
H38 C15 C21 C16 . . . . 177.1
H38 C15 C21 H46 . . . . -0.3
C9 C16 C21 C15 . . . . 1.3(4)
C9 C16 C21 H46 . . . . 178.6
H39 C16 C21 C15 . . . . -177.4
H39 C16 C21 H46 . . . . -0.1
C10 C17 C22 C18 . . . . -1.7(5)
C10 C17 C22 H47 . . . . 179.8
H40 C17 C22 C18 . . . . 178.0
H40 C17 C22 H47 . . . . -0.5
C11 C18 C22 C17 . . . . 0.5(5)
C11 C18 C22 H47 . . . . 179.0
H41 C18 C22 C17 . . . . -178.0
H41 C18 C22 H47 . . . . 0.5

_exptl_crystal_colour            White
_exptl_crystal_description       Powder
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_Q_B
_database_code_depnum_ccdc_archive 'CCDC 1051733'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_audit_creation_date             2014-05-28
_audit_creation_method           'Materials Studio'
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_hall  '-P 1'
_symmetry_Int_Tables_number      2
_symmetry_cell_setting           triclinic
_chemical_name_systematic        
'1-Azabicyclo[2.2.2]oct-3-yl(diphenyl)methanol hydrochloride'
_chemical_name_common            'Quifenadine hydrochloride form B'
_chemical_formula_moiety         'C20 H24 N O, Cl'
_chemical_formula_sum            'C20 H24 Cl N O'
_chemical_formula_weight         329.85
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
_cell_length_a                   6.4080(5)
_cell_length_b                   9.2806(6)
_cell_length_c                   18.3548(12)
_cell_angle_alpha                113.091(9)
_cell_angle_beta                 83.621(11)
_cell_angle_gamma                116.501(13)
_cell_volume                     895.91(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_monochromator  none
_diffrn_ambient_temperature      293(2)

_pd_spec_mounting                capillary
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  white

_pd_meas_2theta_range_min        4.50
_pd_meas_2theta_range_max        70.00
_pd_meas_2theta_range_inc        0.01

_pd_proc_ls_profile_function     'Pseudo Voigt'
_pd_proc_ls_background_function  'linear extrapolation'

_pd_proc_ls_prof_R_factor        none
_pd_proc_ls_prof_wR_factor       none

_refine_ls_goodness_of_fit_all   none
_refine_ls_restrained_S_all      ?
_refine_ls_shift/su_max          ?
_refine_ls_shift/su_mean         ?

_refine_ls_R_factor_all          none

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
C1 C 0.2049(3) 0.823(2) 0.2791(2) 0.0127 Uiso 1
C2 C 0.3953(3) 0.8500(2) 0.2194(2) 0.0127 Uiso 1
C3 C 0.1369(4) 0.6588(2) 0.2959(2) 0.0127 Uiso 1
C4 C 0.3051(4) 0.9825(4) 0.3569(3) 0.0127 Uiso 1
O5 O -0.0001(3) 0.8113(2) 0.2479(2) 0.0127 Uiso 1
C6 C 0.4741(4) 1.0174(2) 0.2007(2) 0.0127 Uiso 1
C7 C 0.3223(2) 0.6926(2) 0.1387(1) 0.0127 Uiso 1
C8 C 0.2829(3) 0.5781(3) 0.2860(2) 0.0127 Uiso 1
C9 C -0.0798(3) 0.5862(3) 0.3252(2) 0.0127 Uiso 1
C10 C 0.5094(4) 1.0225(3) 0.3970(1) 0.0127 Uiso 1
C11 C 0.1973(4) 1.0929(3) 0.3908(1) 0.0127 Uiso 1
C12 C 0.2900(3) 1.0002(4) 0.1457(2) 0.0127 Uiso 1
C13 C 0.6984(3) 1.0383(1) 0.1552(1) 0.0127 Uiso 1
N14 N 0.3851(4) 0.7502(4) 0.0702(1) 0.0127 Uiso 1
C15 C 0.2145(3) 0.4303(3) 0.3030(2) 0.0127 Uiso 1
C16 C -0.1499(4) 0.4403(3) 0.3436(3) 0.0127 Uiso 1
C17 C 0.6037(4) 1.1668(3) 0.4677(1) 0.0127 Uiso 1
C18 C 0.2890(4) 1.2382(3) 0.4613(1) 0.0127 Uiso 1
C19 C 0.2420(3) 0.8401(2) 0.0682(1) 0.0127 Uiso 1
C20 C 0.6411(1) 0.8716(2) 0.0800(1) 0.0127 Uiso 1
C21 C -0.0025(4) 0.3609(3) 0.3323(2) 0.0127 Uiso 1
C22 C 0.4939(3) 1.2760(2) 0.4999(2) 0.0127 Uiso 1
H23 H 0.5077 1.1188 0.2489 0.0152 Uiso 1
Cl24 Cl 0.3174(6) 0.5351(2) -0.1076(3) 0.0127 Uiso 1
H25 H 0.5339 0.8615 0.2413 0.0152 Uiso 1
H26 H -0.0861 0.6932 0.2132 0.0152 Uiso 1
H27 H 0.3962 0.6193 0.1334 0.0152 Uiso 1
H28 H 0.1575 0.6171 0.1307 0.0152 Uiso 1
H29 H 0.4544 0.6297 0.265 0.0152 Uiso 1
H30 H -0.1966 0.6461 0.3345 0.0152 Uiso 1
H31 H 0.5952 0.9382 0.3737 0.0152 Uiso 1
H32 H 0.0367 1.0627 0.3619 0.0152 Uiso 1
H33 H 0.1481 0.9916 0.1711 0.0152 Uiso 1
H34 H 0.3495 1.104 0.1346 0.0152 Uiso 1
H35 H 0.7537 1.1388 0.1418 0.0152 Uiso 1
H36 H 0.8218 1.0575 0.1883 0.0152 Uiso 1
H37 H 0.35 0.6454 0.0187 0.0152 Uiso 1
H38 H 0.3312 0.3705 0.2941 0.0152 Uiso 1
H39 H -0.3186 0.3886 0.3663 0.0152 Uiso 1
H40 H 0.7596 1.1933 0.4981 0.0152 Uiso 1
H41 H 0.2009 1.3206 0.4863 0.0152 Uiso 1
H42 H 0.0813 0.7549 0.0589 0.0152 Uiso 1
H43 H 0.2821 0.8708 0.0226 0.0152 Uiso 1
H44 H 0.6789 0.8953 0.0326 0.0152 Uiso 1
H45 H 0.7223 0.8076 0.082 0.0152 Uiso 1
H46 H -0.0572 0.2466 0.3459 0.0152 Uiso 1
H47 H 0.5661 1.3885 0.5548 0.0152 Uiso 1



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . . 1.548(9)
C1 C3 . . 1.534(16)
C1 C4 . . 1.530(10)
C1 O5 . . 1.434(8)
C2 C6 . . 1.570(3)
C2 C7 . . 1.547(4)
C2 H25 . . .961
C3 C8 . . 1.396(4)
C3 C9 . . 1.398(4)
C4 C10 . . 1.400(5)
C4 C11 . . 1.396(5)
O5 H26 . . .950
C6 C12 . . 1.551(4)
C6 C13 . . 1.553(3)
C6 H23 . . .961
C7 N14 . . 1.500(3)
C7 H27 . . .960
C7 H28 . . .960
C8 C15 . . 1.393(4)
C8 H29 . . 1.080
C9 C16 . . 1.390(4)
C9 H30 . . 1.080
C10 C17 . . 1.390(3)
C10 H31 . . 1.080
C11 C18 . . 1.390(3)
C11 H32 . . 1.080
C12 C19 . . 1.535(4)
C12 H33 . . .960
C12 H34 . . .961
C13 C20 . . 1.538(2)
C13 H35 . . .960
C13 H36 . . .960
N14 C19 . . 1.501(4)
N14 C20 . . 1.500(3)
N14 H37 . . 1.010
C15 C21 . . 1.394(4)
C15 H38 . . 1.080
C16 C21 . . 1.391(4)
C16 H39 . . 1.080
C17 C22 . . 1.396(4)
C17 H40 . . 1.080
C18 C22 . . 1.396(4)
C18 H41 . . 1.080
C19 H42 . . .960
C19 H43 . . .960
C20 H44 . . .959
C20 H45 . . .960
C21 H46 . . 1.080
C22 H47 . . 1.080

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C3 . . . 113.9(7)
C2 C1 C4 . . . 106.6(8)
C2 C1 O5 . . . 108.5(5)
C1 C2 C6 . . . 116.2(6)
C1 C2 C7 . . . 112.3(5)
C1 C2 H25 . . . 108.2
C3 C1 C4 . . . 108.5(5)
C3 C1 O5 . . . 108.5(9)
C1 C3 C8 . . . 123.8(4)
C1 C3 C9 . . . 119.4(4)
C4 C1 O5 . . . 110.8(7)
C1 C4 C10 . . . 120.8(4)
C1 C4 C11 . . . 121.8(4)
C1 O5 H26 . . . 106.8
C6 C2 C7 . . . 106.8(2)
C6 C2 H25 . . . 105.6(
C2 C6 C12 . . . 112.7(2)
C2 C6 C13 . . . 106.85(18)
C2 C6 H23 . . . 110.8
C7 C2 H25 . . . 107.2
C2 C7 N14 . . . 111.65(18)
C2 C7 H27 . . . 112.1
C2 C7 H28 . . . 113.44
C8 C3 C9 . . . 116.8(2)
C3 C8 C15 . . . 121.7(2)
C3 C8 H29 . . . 120.5
C3 C9 C16 . . . 122.4(2)
C3 C9 H30 . . . 119.0
C10 C4 C11 . . . 117.5(4)
C4 C10 C17 . . . 121.8(3)
C4 C10 H31 . . . 119.8
C4 C11 C18 . . . 121.7(3)
C4 C11 H32 . . . 118.9
C12 C6 C13 . . . 107.0(2)
C12 C6 H23 . . . 109.6
C6 C12 C19 . . . 109.0(2)
C6 C12 H33 . . . 111.5
C6 C12 H34 . . . 109.1
C13 C6 H23 . . . 109.9
C6 C13 C20 . . . 108.58(15)
C6 C13 H35 . . . 110.4
C6 C13 H36 . . . 110.3
N14 C7 H27 . . . 107.3
N14 C7 H28 . . . 106.6
C7 N14 C19 . . . 109.12(18)
C7 N14 C20 . . . 109.18(17)
C7 N14 H37 . . . 109.8
H27 C7 H28 . . . 105.4
C15 C8 H29 . . . 117.8
C8 C15 C21 . . . 120.2(2)
C8 C15 H38 . . . 119.7
C16 C9 H30 . . . 118.6
C9 C16 C21 . . . 119.8(3)
C9 C16 H39 . . . 120.0
C17 C10 H31 . . . 118.4
C10 C17 C22 . . . 119.6(3)
C10 C17 H40 . . . 120.3
C18 C11 H32 . . . 119.4
C11 C18 C22 . . . 119.7(3)
C11 C18 H41 . . . 120.0
C19 C12 H33 . . . 110.8
C19 C12 H34 . . . 110.2
C12 C19 N14 . . . 110.54(18)
C12 C19 H42 . . . 112.8
C12 C19 H43 . . . 112.2
H33 C12 H34 . . . 106.1
C20 C13 H35 . . . 110.8
C20 C13 H36 . . . 110.23
C13 C20 N14 . . . 110.73(14)
C13 C20 H44 . . . 112.5
C13 C20 H45 . . . 112.23
H35 C13 H36 . . . 106.6
C19 N14 C20 . . . 110.5(2)
C19 N14 H37 . . . 108.9
N14 C19 H42 . . . 106.8
N14 C19 H43 . . . 106.8
C20 N14 H37 . . . 109.3
N14 C20 H44 . . . 107.0
N14 C20 H45 . . . 106.4
C21 C15 H38 . . . 120.1
C15 C21 C16 . . . 119.1(3)
C15 C21 H46 . . . 120.9
C21 C16 H39 . . . 120.3
C16 C21 H46 . . . 120.0
C22 C17 H40 . . . 120.1
C17 C22 C18 . . . 119.7(3)
C17 C22 H47 . . . 120.1
C22 C18 H41 . . . 120.3
C18 C22 H47 . . . 120.2
H42 C19 H43 . . . 107.4
H44 C20 H45 . . . 107.6


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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 C6 . . . . -179.3(4)
C3 C1 C2 C7 . . . . 57.4(5)
C3 C1 C2 H25 . . . . -60.8
C4 C1 C2 C6 . . . . -59.7(7)
C4 C1 C2 C7 . . . . 177.0(5)
C4 C1 C2 H25 . . . . 58.8
O5 C1 C2 C6 . . . . 59.7(9)
O5 C1 C2 C7 . . . . -63.7(10)
O5 C1 C2 H25 . . . . 178.2
C2 C1 C3 C8 . . . . 24.0(6)
C2 C1 C3 C9 . . . . -158.1(4)
C4 C1 C3 C8 . . . . -94.6(5)
C4 C1 C3 C9 . . . . 83.4(6)
O5 C1 C3 C8 . . . . 145.0(4)
O5 C1 C3 C9 . . . . -37.1(5)
C2 C1 C4 C10 . . . . -60.5(10)
C2 C1 C4 C11 . . . . 119.8(5)
C3 C1 C4 C10 . . . . 62.6(7)
C3 C1 C4 C11 . . . . -117.1(5)
O5 C1 C4 C10 . . . . -178.4(6)
O5 C1 C4 C11 . . . . 1.9(12)
C2 C1 O5 H26 . . . . 85.0
C3 C1 O5 H26 . . . . -39.3
C4 C1 O5 H26 . . . . -158.3
C1 C2 C6 C12 . . . . -74.7(4)
C1 C2 C6 C13 . . . . 168.0(3)
C1 C2 C6 H23 . . . . 48.4
C7 C2 C6 C12 . . . . 51.5(3)
C7 C2 C6 C13 . . . . -65.8(2)
C7 C2 C6 H23 . . . . 174.6
H25 C2 C6 C12 . . . . 165.00
H25 C2 C6 C13 . . . . 48.00
H25 C2 C6 H23 . . . . -71.5
C1 C2 C7 N14 . . . . 137.6(5)
C1 C2 C7 H27 . . . . -102.0
C1 C2 C7 H28 . . . . 17.2
C6 C2 C7 N14 . . . . 9.2(2)
C6 C2 C7 H27 . . . . 129.5
C6 C2 C7 H28 . . . . -111.3
H25 C2 C7 N14 . . . . -104.00
H25 C2 C7 H27 . . . . 16.7
H25 C2 C7 H28 . . . . 135.9
C1 C3 C8 C15 . . . . 179.2(4)
C1 C3 C8 H29 . . . . -0.5
C9 C3 C8 C15 . . . . 1.2(5)
C9 C3 C8 H29 . . . . -178.5
C1 C3 C9 C16 . . . . -178.3(4)
C1 C3 C9 H30 . . . . 1.0
C8 C3 C9 C16 . . . . -0.3(5)
C8 C3 C9 H30 . . . . 179.1
C1 C4 C10 C17 . . . . 179.9(7)
C1 C4 C10 H31 . . . . -1.6
C11 C4 C10 C17 . . . . -0.3(5)
C11 C4 C10 H31 . . . . 178.1
C1 C4 C11 C18 . . . . -179.7(7)
C1 C4 C11 H32 . . . . 1.5
C10 C4 C11 C18 . . . . 0.6(5)
C10 C4 C11 H32 . . . . -178.2
C2 C6 C12 C19 . . . . -57.5(3)
C2 C6 C12 H33 . . . . 65.2
C2 C6 C12 H34 . . . . -177.8
C13 C6 C12 C19 . . . . 59.7(3)
C13 C6 C12 H33 . . . . -177.6
C13 C6 C12 H34 . . . . -60.7
H23 C6 C12 C19 . . . . 179.00
H23 C6 C12 H33 . . . . -58.5
H23 C6 C12 H34 . . . . 58.4
C2 C6 C13 C20 . . . . 57.9(2)
C2 C6 C13 H35 . . . . 179.5
C2 C6 C13 H36 . . . . -63.0
C12 C6 C13 C20 . . . . -63.1(2)
C12 C6 C13 H35 . . . . 58.6
C12 C6 C13 H36 . . . . 176.1
H23 C6 C13 C20 . . . . 178.00
H23 C6 C13 H35 . . . . -60.3
H23 C6 C13 H36 . . . . 57.2
C2 C7 N14 C19 . . . . -66.2(2)
C2 C7 N14 C20 . . . . 54.7(2)
C2 C7 N14 H37 . . . . 174.5
H27 C7 N14 C19 . . . . 171.00
H27 C7 N14 C20 . . . . -69.00
H27 C7 N14 H37 . . . . 51.3
H28 C7 N14 C19 . . . . 58.00
H28 C7 N14 C20 . . . . 179.00
H28 C7 N14 H37 . . . . -61.2
C3 C8 C15 C21 . . . . -1.4(5)
C3 C8 C15 H38 . . . . 179.4
H29 C8 C15 C21 . . . . 178.00
H29 C8 C15 H38 . . . . -0.9
C3 C9 C16 C21 . . . . -0.5(6)
C3 C9 C16 H39 . . . . 179.8(5)
H30 C9 C16 C21 . . . . -179.9(5)
H30 C9 C16 H39 . . . . 0.4(8)
C4 C10 C17 C22 . . . . -0.3(4)
C4 C10 C17 H40 . . . . 178.7
H31 C10 C17 C22 . . . . -179.00
H31 C10 C17 H40 . . . . 0.3
C4 C11 C18 C22 . . . . -0.1(4)
C4 C11 C18 H41 . . . . -179.5
H32 C11 C18 C22 . . . . 179.00
H32 C11 C18 H41 . . . . -0.8
C6 C12 C19 N14 . . . . 0.5(3)
C6 C12 C19 H42 . . . . 120.1
C6 C12 C19 H43 . . . . -118.5
H33 C12 C19 N14 . . . . -123.00
H33 C12 C19 H42 . . . . -3.1
H33 C12 C19 H43 . . . . 118.4
H34 C12 C19 N14 . . . . 120.00
H34 C12 C19 H42 . . . . -120.2
H34 C12 C19 H43 . . . . 1.2
C6 C13 C20 N14 . . . . 5.4(2)
C6 C13 C20 H44 . . . . 125.1
C6 C13 C20 H45 . . . . -113.3
H35 C13 C20 N14 . . . . -116.00
H35 C13 C20 H44 . . . . 3.8
H35 C13 C20 H45 . . . . 125.3
H36 C13 C20 N14 . . . . 126.00
H36 C13 C20 H44 . . . . -114.0
H36 C13 C20 H45 . . . . 7.6
C7 N14 C19 C12 . . . . 60.0(3)
C7 N14 C19 H42 . . . . -63.1
C7 N14 C19 H43 . . . . -177.7
C20 N14 C19 C12 . . . . -60.1(2)
C20 N14 C19 H42 . . . . 176.84
C20 N14 C19 H43 . . . . 62.2
H37 N14 C19 C12 . . . . 179.9(3)
H37 N14 C19 H42 . . . . 56.8
H37 N14 C19 H43 . . . . -57.8
C7 N14 C20 C13 . . . . -63.5(2)
C7 N14 C20 H44 . . . . 173.6
C7 N14 C20 H45 . . . . 58.8
C19 N14 C20 C13 . . . . 56.55(18)
C19 N14 C20 H44 . . . . -66.4
C19 N14 C20 H45 . . . . 178.77
H37 N14 C20 C13 . . . . 176.00
H37 N14 C20 H44 . . . . 53.5
H37 N14 C20 H45 . . . . -61.00
C8 C15 C21 C16 . . . . 0.6(5)
C8 C15 C21 H46 . . . . -179.8
H38 C15 C21 C16 . . . . 179.8(5)
H38 C15 C21 H46 . . . . -0.6
C9 C16 C21 C15 . . . . 0.4(6)
C9 C16 C21 H46 . . . . -179.00
H39 C16 C21 C15 . . . . -179.9(5)
H39 C16 C21 H46 . . . . 0.4(8)
C10 C17 C22 C18 . . . . 0.7(4)
C10 C17 C22 H47 . . . . -180.0(4)
H40 C17 C22 C18 . . . . -178.00
H40 C17 C22 H47 . . . . 1.00
C11 C18 C22 C17 . . . . -0.5(4)
C11 C18 C22 H47 . . . . -179.8(4)
H41 C18 C22 C17 . . . . 179.00
H41 C18 C22 H47 . . . . -0.5(5)
_exptl_crystal_colour            White
_exptl_crystal_description       Powder
_exptl_crystal_recrystallization_method 'Dehydration from dihydrate'
####################################################################### 
# 
# 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_Q_C
_database_code_depnum_ccdc_archive 'CCDC 1051734'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_audit_creation_date             2014-05-16
_audit_creation_method           'Materials Studio'
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_hall  '-P 1'
_symmetry_Int_Tables_number      2
_symmetry_cell_setting           triclinic
_chemical_name_systematic        
'1-Azabicyclo[2.2.2]oct-3-yl(diphenyl)methanol hydrochloride'
_chemical_name_common            'Quifenadine hydrochloride form C'
_chemical_formula_moiety         'C20 H24 N O, Cl'
_chemical_formula_sum            'C20 H24 Cl N O'
_chemical_formula_weight         329.85
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
_cell_length_a                   6.4493(10)
_cell_length_b                   12.9516(18)
_cell_length_c                   11.2219(14)
_cell_angle_alpha                97.596(8)
_cell_angle_beta                 106.619(12)
_cell_angle_gamma                75.255(13)
_cell_volume                     866.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_monochromator  none
_diffrn_ambient_temperature      293(2)
_pd_spec_mounting                capillary
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  white

_pd_meas_2theta_range_min        5.00
_pd_meas_2theta_range_max        70.00
_pd_meas_2theta_range_inc        0.01

_pd_proc_ls_profile_function     'Pseudo Voigt'
_pd_proc_ls_background_function  'linear extrapolation'

_pd_proc_ls_prof_R_factor        none
_pd_proc_ls_prof_wR_factor       none

_refine_ls_goodness_of_fit_all   none
_refine_ls_restrained_S_all      ?
_refine_ls_shift/su_max          ?
_refine_ls_shift/su_mean         ?

_refine_ls_R_factor_all          none

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
C1 C 0.1887(9) 0.7068(4) 0.2712(3) 0.01267 Uiso 1
C2 C -0.0381(9) 0.7164(2) 0.1716(3) 0.01267 Uiso 1
C3 C 0.1596(1) 0.7787(2) 0.3887(3) 0.01267 Uiso 1
C4 C 0.2796(1) 0.5896(3) 0.3065(3) 0.01267 Uiso 1
O5 O 0.3414(1) 0.7368(4) 0.2179(3) 0.01267 Uiso 1
C6 C -0.0450(9) 0.6375(7) 0.0530(3) 0.01267 Uiso 1
C7 C -0.1346(4) 0.8313(2) 0.1262(4) 0.01267 Uiso 1
C8 C 0.3099(2) 0.8423(3) 0.4489(5) 0.01267 Uiso 1
C9 C -0.0140(2) 0.7820(2) 0.4428(1) 0.01267 Uiso 1
C10 C 0.4861(4) 0.5303(7) 0.2908(1) 0.01267 Uiso 1
C11 C 0.1592(1) 0.5372(3) 0.3552(2) 0.01267 Uiso 1
C12 C 0.0735(3) 0.6661(8) -0.0364(3) 0.01267 Uiso 1
C13 C -0.2949(2) 0.6486(3) -0.0179(5) 0.01267 Uiso 1
N14 N -0.2233(2) 0.8306(4) -0.0132(4) 0.01267 Uiso 1
C15 C 0.2903(2) 0.9051(2) 0.5578(9) 0.01267 Uiso 1
C16 C -0.0345(2) 0.8435(2) 0.5524(1) 0.01267 Uiso 1
C17 C 0.5671(2) 0.4234(7) 0.3191(1) 0.01267 Uiso 1
C18 C 0.2375(2) 0.4304(3) 0.3843(9) 0.01267 Uiso 1
C19 C -0.0349(1) 0.7824(8) -0.0728(4) 0.01267 Uiso 1
C20 C -0.3963(1) 0.7653(3) -0.0557(3) 0.01267 Uiso 1
C21 C 0.1194(2) 0.9051(2) 0.6114(2) 0.01267 Uiso 1
C22 C 0.4412(2) 0.3727(4) 0.3649(4) 0.01267 Uiso 1
H23 H 0.0193 0.5654 0.0772 0.0152 Uiso 1
H25 H -0.1441 0.7016 0.2087 0.0152 Uiso 1
H26 H 0.3119 0.8128 0.2221 0.0152 Uiso 1
H27 H -0.2526 0.8684 0.1624 0.0152 Uiso 1
H28 H -0.0269 0.8755 0.1487 0.0152 Uiso 1
H29 H 0.4307 0.8437 0.4156 0.0152 Uiso 1
H30 H -0.1267 0.7419 0.4044 0.0152 Uiso 1
H31 H 0.5745 0.5644 0.2591 0.0152 Uiso 1
H32 H 0.0195 0.5746 0.3697 0.0152 Uiso 1
H33 H 0.2303 0.6576 0.0013 0.0152 Uiso 1
H34 H 0.0589 0.6178 -0.1096 0.0152 Uiso 1
H35 H -0.3103 0.5996 -0.0905 0.0152 Uiso 1
H36 H -0.3734 0.6301 0.0343 0.0152 Uiso 1
H37 H -0.2892 0.9063 -0.0392 0.0152 Uiso 1
H38 H 0.3948 0.9496 0.5957 0.0152 Uiso 1
H39 H -0.1564 0.8457 0.5864 0.0152 Uiso 1
H40 H 0.7082 0.3844 0.3077 0.0152 Uiso 1
H41 H 0.1528 0.3964 0.4188 0.0152 Uiso 1
H42 H 0.0687 0.8287 -0.0467 0.0152 Uiso 1
H43 H -0.0964 0.7862 -0.1613 0.0152 Uiso 1
H44 H -0.4529 0.7703 -0.1443 0.0152 Uiso 1
H45 H -0.5153 0.7998 -0.0191 0.0152 Uiso 1
H46 H 0.1042 0.9492 0.6855 0.0152 Uiso 1
H47 H 0.4951 0.2988 0.3837 0.0152 Uiso 1
Cl24 Cl -0.3300(2) 1.0292(4) -0.1557(7) 0.01267 Uiso 1

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_ccdc_geom_bond_type
C1 C2 1.554(7) . S
C1 C3 1.539(5) . S
C1 C4 1.542(6) . S
C1 O5 1.439(6) . S
C2 C6 1.564(6) . S
C2 C7 1.552(4) . S
C2 H25 1.103 . S
C3 C8 1.400(4) . S
C3 C9 1.408(2) . D
C4 C10 1.404(6) . S
C4 C11 1.404(3) . D
O5 H26 0.971 . S
C6 C12 1.552(7) . S
C6 C13 1.559(7) . S
C6 H23 1.104 . S
C7 N14 1.504(6) . S
C7 H27 1.098 . S
C7 H28 1.083 . S
C8 C15 1.394(12) . D
C8 H29 1.102 . S
C9 C16 1.395(2) . S
C9 H30 1.091 . S
C10 C17 1.394(12) . D
C10 H31 1.096 . S
C11 C18 1.395(6) . S
C11 H32 1.104 . S
C12 C19 1.545(14) . S
C12 H33 1.100 . S
C12 H34 1.103 . S
C13 C20 1.549(5) . S
C13 H35 1.100 . S
C13 H36 1.102 . S
N14 C19 1.511(6) . S
N14 C20 1.502(4) . S
N14 H37 1.021 . S
C15 C21 1.399(5) . S
C15 H38 0.97 . S
C16 C21 1.396(3) . D
C16 H39 1.103 . S
C17 C22 1.398(6) . S
C17 H40 1.106 . S
C18 C22 1.397(5) . D
C18 H41 1.097 . S
C19 H42 1.093 . S
C19 H43 1.103 . S
C20 H44 1.102 . S
C20 H45 1.106 . S
C21 H46 1.102 . S
C22 H47 1.097 . S

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C3 . . . 110.3(4)
C2 C1 C4 . . . 109.1(3)
C2 C1 O5 . . . 108.4(3)
C1 C2 C6 . . . 117.0(4)
C1 C2 C7 . . . 112.1(3)
C1 C2 H25 . . . 108.6
C3 C1 C4 . . . 109.0(3)
C3 C1 O5 . . . 111.0(4)
C1 C3 C8 . . . 121.0(3)
C1 C3 C9 . . . 122.2(3)
C4 C1 O5 . . . 109.0(4)
C1 C4 C10 . . . 121.5(4)
C1 C4 C11 . . . 121.5(3)
C1 O5 H26 . . . 107.4
C6 C2 C7 . . . 107.3(4)
C6 C2 H25 . . . 105.2
C2 C6 C12 . . . 112.5(6)
C2 C6 C13 . . . 106.6(5)
C2 C6 H23 . . . 110.0
C7 C2 H25 . . . 105.8
C2 C7 N14 . . . 111.9(3)
C2 C7 H27 . . . 111.4
C2 C7 H28 . . . 113.2
C8 C3 C9 . . . 116.7(3)
C3 C8 C15 . . . 121.8(3)
C3 C8 H29 . . . 119.9
C3 C9 C16 . . . 122.20(18)
C3 C9 H30 . . . 120.7
C10 C4 C11 . . . 117.0(4)
C4 C10 C17 . . . 122.0(4)
C4 C10 H31 . . . 119.1
C4 C11 C18 . . . 121.9(3)
C4 C11 H32 . . . 120.2
C12 C6 C13 . . . 107.7(3)
C12 C6 H23 . . . 109.9
C6 C12 C19 . . . 108.7(5)
C6 C12 H33 . . . 111.3
C6 C12 H34 . . . 110.1
C13 C6 H23 . . . 110.3
C6 C13 C20 . . . 109.0(4)
C6 C13 H35 . . . 109.9
C6 C13 H36 . . . 109.9
N14 C7 H27 . . . 108.1
N14 C7 H28 . . . 106.3
C7 N14 C19 . . . 109.3(3)
C7 N14 C20 . . . 109.8(3)
C7 N14 H37 . . . 109.7
H27 C7 H28 . . . 105.6
C15 C8 H29 . . . 118.6
C8 C15 C21 . . . 120.5(4)
C8 C15 H38 . . . 119.3
C16 C9 H30 . . . 116.6
C9 C16 C21 . . . 119.87(15)
C9 C16 H39 . . . 121.1
C17 C10 H31 . . . 118.5
C10 C17 C22 . . . 119.7(4)
C10 C17 H40 . . . 121.1
C18 C11 H32 . . . 118.4
C11 C18 C22 . . . 119.8(4)
C11 C18 H41 . . . 119.9
C19 C12 H33 . . . 111.3
C19 C12 H34 . . . 110.2
C12 C19 N14 . . . 110.9(4)
C12 C19 H42 . . . 112.4
C12 C19 H43 . . . 111.9
H33 C12 H34 . . . 105.8
C20 C13 H35 . . . 110.4
C20 C13 H36 . . . 109.8
C13 C20 N14 . . . 110.4(3)
C13 C20 H44 . . . 112.9
C13 C20 H45 . . . 112.7
H35 C13 H36 . . . 107.2
C19 N14 C20 . . . 109.4(4)
C19 N14 H37 . . . 108.8
N14 C19 H42 . . . 106.7
N14 C19 H43 . . . 106.8
C20 N14 H37 . . . 109.9
N14 C20 H44 . . . 106.5
N14 C20 H45 . . . 107.0
C21 C15 H38 . . . 119.7
C15 C21 C16 . . . 119.0(3)
C15 C21 H46 . . . 121.1
C21 C16 H39 . . . 119.1
C16 C21 H46 . . . 120.3
C22 C17 H40 . . . 119.6
C17 C22 C18 . . . 119.6(5)
C17 C22 H47 . . . 119.7
C22 C18 H41 . . . 119.8
C18 C22 H47 . . . 120.7
H42 C19 H43 . . . 107.4
H44 C20 H45 . . . 107.3

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 C6 . . . . -172.2(4)
C3 C1 C2 C7 . . . . 63.3(5)
C3 C1 C2 H25 . . . . -53.7
C4 C1 C2 C6 . . . . -52.5(5)
C4 C1 C2 C7 . . . . -177.0(3)
C4 C1 C2 H25 . . . . 66.0
O5 C1 C2 C6 . . . . 66.1(5)
O5 C1 C2 C7 . . . . -58.5(5)
O5 C1 C2 H25 . . . . -175.7
C2 C1 C3 C8 . . . . -135.9(4)
C2 C1 C3 C9 . . . . 45.8(4)
C4 C1 C3 C8 . . . . 104.4(4)
C4 C1 C3 C9 . . . . -73.9(4)
O5 C1 C3 C8 . . . . -15.8(5)
O5 C1 C3 C9 . . . . 165.9(3)
C2 C1 C4 C10 . . . . 121.0(4)
C2 C1 C4 C11 . . . . -58.7(4)
C3 C1 C4 C10 . . . . -118.6(4)
C3 C1 C4 C11 . . . . 61.8(5)
O5 C1 C4 C10 . . . . 2.8(4)
O5 C1 C4 C11 . . . . -176.9(3)
C2 C1 O5 H26 . . . . 80.0
C3 C1 O5 H26 . . . . -40.9
C4 C1 O5 H26 . . . . -161.1
C1 C2 C6 C12 . . . . -72.8(6)
C1 C2 C6 C13 . . . . 169.4(4)
C1 C2 C6 H23 . . . . 50.3
C7 C2 C6 C12 . . . . 54.1(6)
C7 C2 C6 C13 . . . . -63.6(5)
C7 C2 C6 H23 . . . . 177.5
H25 C2 C6 C12 . . . . 166.7
H25 C2 C6 C13 . . . . 49.2
H25 C2 C6 H23 . . . . -70.1
C1 C2 C7 N14 . . . . 135.4(3)
C1 C2 C7 H27 . . . . -103.7
C1 C2 C7 H28 . . . . 15.1
C6 C2 C7 N14 . . . . 5.6(5)
C6 C2 C7 H27 . . . . 126.7
C6 C2 C7 H28 . . . . -114.5
H25 C2 C7 N14 . . . . -106.4
H25 C2 C7 H27 . . . . 14.7
H25 C2 C7 H28 . . . . 133.6
C1 C3 C8 C15 . . . . -177.8(4)
C1 C3 C8 H29 . . . . 2.2
C9 C3 C8 C15 . . . . .6(6)
C9 C3 C8 H29 . . . . -179.3
C1 C3 C9 C16 . . . . 177.1(3)
C1 C3 C9 H30 . . . . -3.8
C8 C3 C9 C16 . . . . -1.3(4)
C8 C3 C9 H30 . . . . 177.8
C1 C4 C10 C17 . . . . -178.2(3)
C1 C4 C10 H31 . . . . 1.6
C11 C4 C10 C17 . . . . 1.5(4)
C11 C4 C10 H31 . . . . -178.3
C1 C4 C11 C18 . . . . 178.3(5)
C1 C4 C11 H32 . . . . -1.9
C10 C4 C11 C18 . . . . -1.4(6)
C10 C4 C11 H32 . . . . 178.4
C2 C6 C12 C19 . . . . -56.8(5)
C2 C6 C12 H33 . . . . 65.8
C2 C6 C12 H34 . . . . -177.2
C13 C6 C12 C19 . . . . 60.3(6)
C13 C6 C12 H33 . . . . -177.5
C13 C6 C12 H34 . . . . -60.6
H23 C6 C12 C19 . . . . -180.0
H23 C6 C12 H33 . . . . -57.4
H23 C6 C12 H34 . . . . 59.5
C2 C6 C13 C20 . . . . 60.9(5)
C2 C6 C13 H35 . . . . -177.7
C2 C6 C13 H36 . . . . -60.0
C12 C6 C13 C20 . . . . -60.0(7)
C12 C6 C13 H35 . . . . 61.2
C12 C6 C13 H36 . . . . 178.9
H23 C6 C13 C20 . . . . 179.8
H23 C6 C13 H35 . . . . -58.6
H23 C6 C13 H36 . . . . 59.1
C2 C7 N14 C19 . . . . -63.2(5)
C2 C7 N14 C20 . . . . 56.8(4)
C2 C7 N14 H37 . . . . 178.1
H27 C7 N14 C19 . . . . 174.4
H27 C7 N14 C20 . . . . -65.7
H27 C7 N14 H37 . . . . 55.1
H28 C7 N14 C19 . . . . 61.4
H28 C7 N14 C20 . . . . -178.7
H28 C7 N14 H37 . . . . -57.9
C3 C8 C15 C21 . . . . .9(7)
C3 C8 C15 H38 . . . . -178.3
H29 C8 C15 C21 . . . . -179.2
H29 C8 C15 H38 . . . . 1.7
C3 C9 C16 C21 . . . . .5(3)
C3 C9 C16 H39 . . . . 178.6
H30 C9 C16 C21 . . . . -178.6
H30 C9 C16 H39 . . . . -.6
C4 C10 C17 C22 . . . . -.2(4)
C4 C10 C17 H40 . . . . -180.0
H31 C10 C17 C22 . . . . -179.9
H31 C10 C17 H40 . . . . .3
C4 C11 C18 C22 . . . . -.1(9)
C4 C11 C18 H41 . . . . 179.1
H32 C11 C18 C22 . . . . -179.9
H32 C11 C18 H41 . . . . -.6
C6 C12 C19 N14 . . . . -1.3(5)
C6 C12 C19 H42 . . . . 118.3
C6 C12 C19 H43 . . . . -120.8
H33 C12 C19 N14 . . . . -123.9
H33 C12 C19 H42 . . . . -4.2
H33 C12 C19 H43 . . . . 116.7
H34 C12 C19 N14 . . . . 119.1
H34 C12 C19 H42 . . . . -121.2
H34 C12 C19 H43 . . . . -.4
C6 C13 C20 N14 . . . . .3(4)
C6 C13 C20 H44 . . . . 119.3
C6 C13 C20 H45 . . . . -118.9
H35 C13 C20 N14 . . . . -120.9
H35 C13 C20 H44 . . . . -2.0
H35 C13 C20 H45 . . . . 119.8
H36 C13 C20 N14 . . . . 121.2
H36 C13 C20 H44 . . . . -119.9
H36 C13 C20 H45 . . . . 1.9
C7 N14 C19 C12 . . . . 60.4(5)
C7 N14 C19 H42 . . . . -62.8
C7 N14 C19 H43 . . . . -177.5
C20 N14 C19 C12 . . . . -59.8(4)
C20 N14 C19 H42 . . . . 177.0
C20 N14 C19 H43 . . . . 62.4
H37 N14 C19 C12 . . . . 179.9
H37 N14 C19 H42 . . . . 57.0
H37 N14 C19 H43 . . . . -57.7
C7 N14 C20 C13 . . . . -59.9(4)
C7 N14 C20 H44 . . . . 177.1
C7 N14 C20 H45 . . . . 62.6
C19 N14 C20 C13 . . . . 60.0(5)
C19 N14 C20 H44 . . . . -63.1
C19 N14 C20 H45 . . . . -177.6
H37 N14 C20 C13 . . . . 179.1
H37 N14 C20 H44 . . . . 56.4
H37 N14 C20 H45 . . . . -58.2
C8 C15 C21 C16 . . . . -1.7(6)
C8 C15 C21 H46 . . . . -178.9
H38 C15 C21 C16 . . . . 177.5
H38 C15 C21 H46 . . . . .2
C9 C16 C21 C15 . . . . 1.0(4)
C9 C16 C21 H46 . . . . 178.3
H39 C16 C21 C15 . . . . -177.1
H39 C16 C21 H46 . . . . .2
C10 C17 C22 C18 . . . . -1.3(6)
C10 C17 C22 H47 . . . . 179.3
H40 C17 C22 C18 . . . . 178.5
H40 C17 C22 H47 . . . . -.9
C11 C18 C22 C17 . . . . 1.5(9)
C11 C18 C22 H47 . . . . -179.1
H41 C18 C22 C17 . . . . -177.8
H41 C18 C22 H47 . . . . 1.6

_exptl_crystal_colour            White
_exptl_crystal_description       Powder
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: iso-butanol '
