# Electronic Supplementary Material (ESI) for Faraday Discussions.
# 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. 
# 
#######################################################################

data_GWO11a
_audit_block_doi                 10.5517/ccdc.csd.cc1zm8b6
_database_code_depnum_ccdc_archive 'CCDC 1835768'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8FD00072G 2018
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            LoratadineI-m100(L13)
_chemical_source_common          ACN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Cl N2 O2'
_chemical_formula_weight         382.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   27.997(4)
_cell_length_b                   4.918(1)
_cell_length_c                   28.971(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.987(1)
_cell_angle_gamma                90.00
_cell_volume                     3772.0(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      68.2

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    1.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4137
_exptl_absorpt_correction_T_max  0.9439
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17978
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         66.58
_reflns_number_total             3284
_reflns_number_gt                3035
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.630 (Bruker AXS, 2003)'
_computing_cell_refinement       'SAINT V7.36A (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT V7.36A (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0611P)²+4.7765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3284
_refine_ls_number_parameters     292
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85064(6) 0.6041(4) 0.37050(6) 0.0248(4) Uani 1 1 d . D .
C2 C 0.88759(7) 0.4141(4) 0.37202(7) 0.0297(4) Uani 1 1 d . . .
H2 H 0.9027 0.3140 0.4012 0.036 Uiso 1 1 calc R . .
C3 C 0.90303(7) 0.3670(4) 0.33182(7) 0.0327(4) Uani 1 1 d . D .
H3 H 0.9282 0.2352 0.3331 0.039 Uiso 1 1 calc R . .
C4 C 0.88092(7) 0.5162(4) 0.28996(7) 0.0320(5) Uani 1 1 d . . .
C5 C 0.84415(7) 0.7078(4) 0.28737(7) 0.0299(4) Uani 1 1 d . D .
H5 H 0.8296 0.8084 0.2582 0.036 Uiso 1 1 calc R . .
C6 C 0.82840(7) 0.7538(4) 0.32775(6) 0.0260(4) Uani 1 1 d . . .
C7 C 0.78778(7) 0.9548(4) 0.32657(7) 0.0299(4) Uani 1 1 d . D .
H7A H 0.7824 1.0772 0.2982 0.036 Uiso 1 1 calc R . .
H7B H 0.7988 1.0673 0.3565 0.036 Uiso 1 1 calc R . .
C8 C 0.73812(7) 0.8144(4) 0.32306(7) 0.0302(4) Uani 1 1 d . . .
H8A H 0.7128 0.9576 0.3214 0.036 Uiso 1 1 calc R D .
H8B H 0.7266 0.7142 0.2917 0.036 Uiso 1 1 calc R . .
C9 C 0.73757(7) 0.6175(4) 0.36332(6) 0.0257(4) Uani 1 1 d . D .
C10 C 0.69159(7) 0.4963(4) 0.35923(7) 0.0325(4) Uani 1 1 d . . .
H10 H 0.6628 0.5383 0.3320 0.039 Uiso 1 1 calc R D .
C11 C 0.68707(7) 0.3164(5) 0.39396(8) 0.0361(5) Uani 1 1 d . D .
H11 H 0.6556 0.2339 0.3911 0.043 Uiso 1 1 calc R . .
C12 C 0.72976(7) 0.2595(4) 0.43306(7) 0.0335(4) Uani 1 1 d . . .
H12 H 0.7270 0.1345 0.4571 0.040 Uiso 1 1 calc R D .
N13 N 0.77461(6) 0.3722(3) 0.43859(6) 0.0297(4) Uani 1 1 d . D .
C14 C 0.77900(7) 0.5481(4) 0.40457(6) 0.0241(4) Uani 1 1 d . . .
C15 C 0.83172(6) 0.6491(4) 0.41288(6) 0.0246(4) Uani 1 1 d . D .
C16 C 0.86042(7) 0.7618(4) 0.45501(6) 0.0262(4) Uani 1 1 d . . .
C17 C 0.84255(7) 0.8242(4) 0.49773(6) 0.0284(4) Uani 1 1 d . C .
H17A H 0.8080 0.7513 0.4912 0.034 Uiso 1 1 calc R . .
H17B H 0.8413 1.0236 0.5018 0.034 Uiso 1 1 calc R . .
C18 C 0.87811(7) 0.6978(4) 0.54461(7) 0.0302(4) Uani 1 1 d . . .
H18A H 0.8681 0.7578 0.5728 0.036 Uiso 1 1 calc R A 1
H18B H 0.8753 0.4972 0.5425 0.036 Uiso 1 1 calc R A 1
C20 C 0.94844(7) 0.7104(5) 0.51174(7) 0.0332(5) Uani 1 1 d . . .
H20A H 0.9481 0.5107 0.5074 0.040 Uiso 1 1 calc R B 1
H20B H 0.9836 0.7745 0.5190 0.040 Uiso 1 1 calc R B 1
C21 C 0.91479(7) 0.8438(4) 0.46492(7) 0.0317(4) Uani 1 1 d . C .
H21A H 0.9179 1.0440 0.4681 0.038 Uiso 1 1 calc R . .
H21B H 0.9259 0.7878 0.4372 0.038 Uiso 1 1 calc R . .
N19A N 0.93044(6) 0.7784(4) 0.55211(5) 0.0320(4) Uani 0.545(6) 1 d PDU C 1
C22A C 0.9594(2) 0.9056(9) 0.5920(2) 0.0318(10) Uani 0.545(6) 1 d PDU C 1
O23A O 1.0027(2) 0.9691(14) 0.5974(3) 0.0371(13) Uani 0.545(6) 1 d PDU C 1
O24A O 0.93525(14) 0.9532(10) 0.62497(13) 0.0343(8) Uani 0.545(6) 1 d PDU C 1
C25A C 0.96544(17) 1.0882(10) 0.66921(17) 0.0369(10) Uani 0.545(6) 1 d PDU C 1
H25A H 0.9998 1.0093 0.6800 0.044 Uiso 0.545(6) 1 calc PR C 1
H25B H 0.9504 1.0554 0.6952 0.044 Uiso 0.545(6) 1 calc PR C 1
C26A C 0.96896(19) 1.3855(12) 0.66221(19) 0.0426(12) Uani 0.545(6) 1 d PDU C 1
H26A H 0.9865 1.4193 0.6385 0.064 Uiso 0.545(6) 1 calc PR C 1
H26B H 0.9878 1.4704 0.6934 0.064 Uiso 0.545(6) 1 calc PR C 1
H26C H 0.9349 1.4633 0.6501 0.064 Uiso 0.545(6) 1 calc PR C 1
N19B N 0.93044(6) 0.7784(4) 0.55211(5) 0.0320(4) Uani 0.455(6) 1 d PDU C 2
C22B C 0.9585(3) 0.9714(12) 0.5839(2) 0.0322(11) Uani 0.455(6) 1 d PDU C 2
O23B O 1.0004(3) 1.0535(17) 0.5874(4) 0.0436(17) Uani 0.455(6) 1 d PDU C 2
O24B O 0.93302(16) 1.0670(11) 0.61290(16) 0.0329(9) Uani 0.455(6) 1 d PDU C 2
C25B C 0.9595(2) 1.2596(15) 0.6500(2) 0.0397(13) Uani 0.455(6) 1 d PDU C 2
H25C H 0.9353 1.3968 0.6540 0.048 Uiso 0.455(6) 1 calc PR C 2
H25D H 0.9852 1.3554 0.6393 0.048 Uiso 0.455(6) 1 calc PR C 2
C26B C 0.9847(2) 1.1257(12) 0.6976(2) 0.0480(16) Uani 0.455(6) 1 d PDU C 2
H26D H 0.9597 1.0235 0.7076 0.072 Uiso 0.455(6) 1 calc PR C 2
H26E H 1.0003 1.2641 0.7223 0.072 Uiso 0.455(6) 1 calc PR C 2
H26F H 1.0108 1.0010 0.6945 0.072 Uiso 0.455(6) 1 calc PR C 2
Cl27 Cl 0.900048(19) 0.46126(14) 0.238953(18) 0.0464(2) Uani 1 1 d . D 2


_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
C1 C2 1.384(3) . ?
C1 C6 1.401(3) . ?
C1 C15 1.503(2) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 Cl27 1.7487(19) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(3) . ?
C7 C8 1.526(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.388(3) . ?
C9 C14 1.410(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 N13 1.334(3) . ?
C12 H12 0.9500 . ?
N13 C14 1.347(2) . ?
C14 C15 1.501(2) . ?
C15 C16 1.343(3) . ?
C16 C21 1.509(3) . ?
C16 C17 1.510(3) . ?
C17 C18 1.531(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N19A 1.464(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C20 N19A 1.455(2) . ?
C20 C21 1.525(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
N19A C22A 1.331(6) . ?
C22A O23A 1.213(7) . ?
C22A O24A 1.358(7) . ?
O24A C25A 1.447(6) . ?
C25A C26A 1.484(7) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C22B O23B 1.214(9) . ?
C22B O24B 1.350(8) . ?
O24B C25B 1.444(8) . ?
C25B C26B 1.484(8) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 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
C2 C1 C6 119.72(17) . . ?
C2 C1 C15 122.14(16) . . ?
C6 C1 C15 118.10(16) . . ?
C1 C2 C3 121.32(18) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 118.43(18) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.62(18) . . ?
C3 C4 Cl27 119.18(16) . . ?
C5 C4 Cl27 119.19(16) . . ?
C4 C5 C6 119.90(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.00(17) . . ?
C5 C6 C7 122.13(16) . . ?
C1 C6 C7 118.86(16) . . ?
C6 C7 C8 111.78(16) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 118.28(15) . . ?
C9 C8 H8A 107.7 . . ?
C7 C8 H8A 107.7 . . ?
C9 C8 H8B 107.7 . . ?
C7 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
C10 C9 C14 116.90(17) . . ?
C10 C9 C8 116.67(16) . . ?
C14 C9 C8 126.43(17) . . ?
C11 C10 C9 121.14(18) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 117.96(18) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
N13 C12 C11 122.95(18) . . ?
N13 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C12 N13 C14 119.04(16) . . ?
N13 C14 C9 122.01(17) . . ?
N13 C14 C15 114.49(15) . . ?
C9 C14 C15 123.41(16) . . ?
C16 C15 C14 123.28(16) . . ?
C16 C15 C1 122.49(16) . . ?
C14 C15 C1 114.19(15) . . ?
C15 C16 C21 123.46(17) . . ?
C15 C16 C17 124.67(16) . . ?
C21 C16 C17 111.87(15) . . ?
C16 C17 C18 110.58(15) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N19A C18 C17 110.63(15) . . ?
N19A C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
N19A C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
N19A C20 C21 109.93(16) . . ?
N19A C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
N19A C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C16 C21 C20 110.31(16) . . ?
C16 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C16 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C22A N19A C20 122.2(3) . . ?
C22A N19A C18 123.6(3) . . ?
C20 N19A C18 114.20(15) . . ?
O23A C22A N19A 122.3(6) . . ?
O23A C22A O24A 124.8(6) . . ?
N19A C22A O24A 112.9(5) . . ?
C22A O24A C25A 114.9(4) . . ?
O24A C25A C26A 112.1(5) . . ?
O24A C25A H25A 109.2 . . ?
C26A C25A H25A 109.2 . . ?
O24A C25A H25B 109.2 . . ?
C26A C25A H25B 109.2 . . ?
H25A C25A H25B 107.9 . . ?
O23B C22B O24B 121.6(7) . . ?
C22B O24B C25B 116.3(5) . . ?
O24B C25B C26B 112.0(7) . . ?
O24B C25B H25C 109.2 . . ?
C26B C25B H25C 109.2 . . ?
O24B C25B H25D 109.2 . . ?
C26B C25B H25D 109.2 . . ?
H25C C25B H25D 107.9 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(3) . . . . ?
C15 C1 C2 C3 177.17(17) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 Cl27 179.68(15) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
Cl27 C4 C5 C6 179.89(14) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -178.56(17) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C15 C1 C6 C5 -177.70(16) . . . . ?
C2 C1 C6 C7 178.89(17) . . . . ?
C15 C1 C6 C7 1.2(2) . . . . ?
C5 C6 C7 C8 105.0(2) . . . . ?
C1 C6 C7 C8 -73.9(2) . . . . ?
C6 C7 C8 C9 59.4(2) . . . . ?
C7 C8 C9 C10 179.20(17) . . . . ?
C7 C8 C9 C14 -0.2(3) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 -179.58(18) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 N13 0.5(3) . . . . ?
C11 C12 N13 C14 -0.5(3) . . . . ?
C12 N13 C14 C9 0.2(3) . . . . ?
C12 N13 C14 C15 -176.43(17) . . . . ?
C10 C9 C14 N13 0.1(3) . . . . ?
C8 C9 C14 N13 179.48(17) . . . . ?
C10 C9 C14 C15 176.45(17) . . . . ?
C8 C9 C14 C15 -4.2(3) . . . . ?
N13 C14 C15 C16 -53.0(2) . . . . ?
C9 C14 C15 C16 130.4(2) . . . . ?
N13 C14 C15 C1 124.75(17) . . . . ?
C9 C14 C15 C1 -51.8(2) . . . . ?
C2 C1 C15 C16 69.0(3) . . . . ?
C6 C1 C15 C16 -113.4(2) . . . . ?
C2 C1 C15 C14 -108.86(19) . . . . ?
C6 C1 C15 C14 68.7(2) . . . . ?
C14 C15 C16 C21 175.10(17) . . . . ?
C1 C15 C16 C21 -2.5(3) . . . . ?
C14 C15 C16 C17 -5.5(3) . . . . ?
C1 C15 C16 C17 176.86(17) . . . . ?
C15 C16 C17 C18 127.0(2) . . . . ?
C21 C16 C17 C18 -53.6(2) . . . . ?
C16 C17 C18 N19A 52.8(2) . . . . ?
C15 C16 C21 C20 -125.4(2) . . . . ?
C17 C16 C21 C20 55.1(2) . . . . ?
N19A C20 C21 C16 -55.8(2) . . . . ?
C21 C20 N19A C22A -121.3(2) . . . . ?
C21 C20 N19A C18 58.0(2) . . . . ?
C17 C18 N19A C22A 122.7(2) . . . . ?
C17 C18 N19A C20 -56.7(2) . . . . ?
C20 N19A C22A O23A -1.1(3) . . . . ?
C18 N19A C22A O23A 179.6(3) . . . . ?
C20 N19A C22A O24A 179.2(2) . . . . ?
C18 N19A C22A O24A -0.1(3) . . . . ?
O23A C22A O24A C25A -0.4(5) . . . . ?
N19A C22A O24A C25A 179.3(4) . . . . ?
C22A O24A C25A C26A 79.3(4) . . . . ?
O23B C22B O24B C25B -3.5(6) . . . . ?
C22B O24B C25B C26B -94.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.059
_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_GWO30a
_audit_block_doi                 10.5517/ccdc.csd.cc1zm8jd
_database_code_depnum_ccdc_archive 'CCDC 1835774'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8FD00072G 2018
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;

_chemical_name_common            loratadine-form2-He
_chemical_source_common          TOL/TBME
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Cl N2 O2'
_chemical_formula_weight         382.87

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   35.652(10)
_cell_length_b                   5.206(2)
_cell_length_c                   22.743(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.418(14)
_cell_angle_gamma                90.00
_cell_volume                     3747(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    10(2)
_cell_measurement_reflns_used    22240
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      25.7

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 loratadine disordered (0.53:0.42) 
;

_diffrn_ambient_temperature      10(2)
_diffrn_radiation_wavelength     0.711
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'beamline PXII SLS'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'one-circle goniometer'
_diffrn_measurement_method       φ-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19746
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3215
_reflns_number_gt                2867
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'DA+ (Wang, 2017)'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0407P)²+11.7293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     265
_refine_ls_number_restraints     282
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36066(7) 0.5924(5) 0.86616(11) 0.0209(5) Uani 1 1 d U . .
C2 C 0.37549(9) 0.7804(7) 0.91464(18) 0.0516(10) Uani 1 1 d U B .
H2 H 0.3986 0.8833 0.9190 0.062 Uiso 1 1 calc R . .
C3 C 0.35817(9) 0.8254(6) 0.95695(16) 0.0440(8) Uani 1 1 d U . .
H3 H 0.3691 0.9563 0.9897 0.053 Uiso 1 1 calc R B .
C4 C 0.32526(7) 0.6778(5) 0.95053(11) 0.0251(6) Uani 1 1 d U B .
C5 C 0.30991(10) 0.4868(7) 0.90393(14) 0.0449(8) Uani 1 1 d U . .
H5 H 0.2872 0.3829 0.9009 0.054 Uiso 1 1 calc R A 1
C6A C 0.32712(9) 0.4431(5) 0.86110(13) 0.0320(6) Uani 0.531(6) 1 d PU B 1
C7A C 0.32033(16) 0.1990(9) 0.8170(2) 0.0210(10) Uani 0.531(6) 1 d PU B 1
H7A H 0.3477 0.1359 0.8214 0.025 Uiso 0.531(6) 1 calc PR B 1
H7B H 0.3069 0.0601 0.8304 0.025 Uiso 0.531(6) 1 calc PR B 1
C8A C 0.29178(18) 0.2808(10) 0.7461(2) 0.0214(10) Uani 0.531(6) 1 d PU B 1
H8A H 0.2668 0.3688 0.7447 0.026 Uiso 0.531(6) 1 calc PR B 1
H8B H 0.2817 0.1248 0.7183 0.026 Uiso 0.531(6) 1 calc PR B 1
C9A C 0.31244(9) 0.4594(5) 0.71552(12) 0.0310(6) Uani 0.531(6) 1 d PU B 1
C6B C 0.32712(9) 0.4431(5) 0.86110(13) 0.0320(6) Uani 0.469(6) 1 d PU B 2
C7B C 0.29553(18) 0.2792(11) 0.8015(3) 0.0208(11) Uani 0.469(6) 1 d PU B 2
H7C H 0.2891 0.1193 0.8187 0.025 Uiso 0.469(6) 1 calc PR B 2
H7D H 0.2688 0.3762 0.7779 0.025 Uiso 0.469(6) 1 calc PR B 2
C8B C 0.3118(2) 0.2082(12) 0.7521(3) 0.0218(11) Uani 0.469(6) 1 d PU B 2
H8C H 0.2929 0.0797 0.7200 0.026 Uiso 0.469(6) 1 calc PR B 2
H8D H 0.3405 0.1345 0.7755 0.026 Uiso 0.469(6) 1 calc PR B 2
C9B C 0.31244(9) 0.4594(5) 0.71552(12) 0.0310(6) Uani 0.469(6) 1 d PU B 2
C10 C 0.28619(9) 0.5186(6) 0.64935(13) 0.0369(7) Uani 1 1 d U . .
H10 H 0.2611 0.4223 0.6251 0.044 Uiso 1 1 calc R B 1
C11 C 0.29626(8) 0.7142(6) 0.61898(13) 0.0323(6) Uani 1 1 d U B .
H11 H 0.2783 0.7575 0.5740 0.039 Uiso 1 1 calc R . .
C12 C 0.33309(8) 0.8455(6) 0.65551(16) 0.0452(8) Uani 1 1 d U . .
H12 H 0.3402 0.9814 0.6346 0.054 Uiso 1 1 calc R B .
N13 N 0.35957(7) 0.7933(5) 0.71895(13) 0.0418(7) Uani 1 1 d U B .
C14 C 0.34945(7) 0.6020(5) 0.74855(12) 0.0202(5) Uani 1 1 d U . .
C15 C 0.37951(7) 0.5568(5) 0.82001(11) 0.0194(5) Uani 1 1 d U B .
C16 C 0.42031(7) 0.4952(5) 0.84023(12) 0.0212(5) Uani 1 1 d U . .
C17 C 0.43862(7) 0.4426(5) 0.79347(11) 0.0200(5) Uani 1 1 d U B .
H17A H 0.4610 0.5700 0.8010 0.024 Uiso 1 1 calc R . .
H17B H 0.4162 0.4610 0.7472 0.024 Uiso 1 1 calc R . .
C18 C 0.45719(7) 0.1722(5) 0.80384(11) 0.0191(5) Uani 1 1 d U . .
H18A H 0.4342 0.0439 0.7910 0.023 Uiso 1 1 calc R B .
H18B H 0.4711 0.1466 0.7754 0.023 Uiso 1 1 calc R . .
N19 N 0.48805(6) 0.1347(4) 0.87349(9) 0.0188(4) Uani 1 1 d U B .
C20 C 0.47246(7) 0.1865(5) 0.92129(11) 0.0223(5) Uani 1 1 d U . .
H20A H 0.4962 0.1746 0.9667 0.027 Uiso 1 1 calc R B .
H20B H 0.4513 0.0547 0.9169 0.027 Uiso 1 1 calc R . .
C21 C 0.45237(7) 0.4519(5) 0.91124(12) 0.0243(5) Uani 1 1 d U B .
H21A H 0.4385 0.4699 0.9400 0.029 Uiso 1 1 calc R . .
H21B H 0.4747 0.5846 0.9246 0.029 Uiso 1 1 calc R . .
C22 C 0.52469(7) 0.0025(5) 0.89402(11) 0.0186(5) Uani 1 1 d U . .
O23 O 0.54862(5) -0.0498(3) 0.95147(8) 0.0240(4) Uani 1 1 d U B .
O24 O 0.53217(5) -0.0629(3) 0.84248(8) 0.0203(4) Uani 1 1 d U B .
C25 C 0.57324(7) -0.1782(5) 0.86081(12) 0.0230(5) Uani 1 1 d U . .
H25A H 0.5949 -0.0880 0.9001 0.028 Uiso 1 1 calc R B .
H25B H 0.5805 -0.1558 0.8240 0.028 Uiso 1 1 calc R . .
C26 C 0.57403(8) -0.4592(5) 0.87625(13) 0.0292(6) Uani 1 1 d U B .
H26A H 0.5701 -0.4812 0.9159 0.044 Uiso 1 1 calc R . .
H26B H 0.6013 -0.5327 0.8842 0.044 Uiso 1 1 calc R . .
H26C H 0.5512 -0.5473 0.8388 0.044 Uiso 1 1 calc R . .
Cl27 Cl 0.302504(19) 0.72978(16) 1.00332(3) 0.0383(2) Uani 1 1 d 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
C1 C2 1.384(4) . ?
C1 C6A 1.386(4) . ?
C1 C15 1.496(3) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.353(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(4) . ?
C4 Cl27 1.752(2) . ?
C5 C6A 1.388(4) . ?
C5 H5 0.9500 . ?
C6A C7A 1.567(5) . ?
C7A C8A 1.518(7) . ?
C7A H7A 0.9900 . ?
C7A H7B 0.9900 . ?
C8A C9A 1.537(5) . ?
C8A H8A 0.9900 . ?
C8A H8B 0.9900 . ?
C9A C10 1.392(4) . ?
C9A C14 1.394(4) . ?
C7B C8B 1.528(8) . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C8B H8C 0.9900 . ?
C8B H8D 0.9900 . ?
C10 C11 1.368(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9500 . ?
C12 N13 1.339(4) . ?
C12 H12 0.9500 . ?
N13 C14 1.341(3) . ?
C14 C15 1.497(3) . ?
C15 C16 1.347(3) . ?
C16 C21 1.505(3) . ?
C16 C17 1.507(3) . ?
C17 C18 1.527(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N19 1.467(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N19 C22 1.355(3) . ?
N19 C20 1.456(3) . ?
C20 C21 1.524(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O23 1.218(3) . ?
C22 O24 1.360(3) . ?
O24 C25 1.454(3) . ?
C25 C26 1.502(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C2 C1 C6A 117.5(2) . . ?
C2 C1 C15 121.1(2) . . ?
C6A C1 C15 121.4(2) . . ?
C3 C2 C1 123.0(3) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 Cl27 119.4(2) . . ?
C5 C4 Cl27 119.7(2) . . ?
C4 C5 C6A 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6A C5 H5 119.5 . . ?
C1 C6A C5 119.5(2) . . ?
C1 C6A C7A 112.4(3) . . ?
C5 C6A C7A 126.5(3) . . ?
C8A C7A C6A 106.4(4) . . ?
C8A C7A H7A 110.4 . . ?
C6A C7A H7A 110.4 . . ?
C8A C7A H7B 110.4 . . ?
C6A C7A H7B 110.4 . . ?
H7A C7A H7B 108.6 . . ?
C7A C8A C9A 115.1(4) . . ?
C7A C8A H8A 108.5 . . ?
C9A C8A H8A 108.5 . . ?
C7A C8A H8B 108.5 . . ?
C9A C8A H8B 108.5 . . ?
H8A C8A H8B 107.5 . . ?
C10 C9A C14 117.6(2) . . ?
C10 C9A C8A 113.5(3) . . ?
C14 C9A C8A 127.6(3) . . ?
C8B C7B H7C 108.8 . . ?
C8B C7B H7D 108.8 . . ?
H7C C7B H7D 107.7 . . ?
C7B C8B H8C 110.3 . . ?
C7B C8B H8D 110.3 . . ?
H8C C8B H8D 108.5 . . ?
C11 C10 C9A 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9A C10 H10 119.7 . . ?
C10 C11 C12 117.8(3) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
N13 C12 C11 123.7(3) . . ?
N13 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
C12 N13 C14 118.2(2) . . ?
N13 C14 C9A 122.1(2) . . ?
N13 C14 C15 116.0(2) . . ?
C9A C14 C15 121.9(2) . . ?
C16 C15 C1 123.6(2) . . ?
C16 C15 C14 121.9(2) . . ?
C1 C15 C14 114.44(19) . . ?
C15 C16 C21 124.7(2) . . ?
C15 C16 C17 123.6(2) . . ?
C21 C16 C17 111.61(19) . . ?
C16 C17 C18 110.88(19) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N19 C18 C17 110.23(19) . . ?
N19 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N19 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C22 N19 C20 118.40(19) . . ?
C22 N19 C18 124.36(19) . . ?
C20 N19 C18 115.28(18) . . ?
N19 C20 C21 111.75(19) . . ?
N19 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N19 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C16 C21 C20 111.6(2) . . ?
C16 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C16 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
O23 C22 N19 124.8(2) . . ?
O23 C22 O24 123.4(2) . . ?
N19 C22 O24 111.76(19) . . ?
C22 O24 C25 115.31(17) . . ?
O24 C25 C26 112.2(2) . . ?
O24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
O24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1 C2 C3 -0.6(5) . . . . ?
C15 C1 C2 C3 177.9(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 Cl27 -179.9(3) . . . . ?
C3 C4 C5 C6A -1.4(5) . . . . ?
Cl27 C4 C5 C6A 179.4(2) . . . . ?
C2 C1 C6A C5 0.1(4) . . . . ?
C15 C1 C6A C5 -178.4(3) . . . . ?
C2 C1 C6A C7A -166.4(3) . . . . ?
C15 C1 C6A C7A 15.1(4) . . . . ?
C4 C5 C6A C1 0.9(5) . . . . ?
C4 C5 C6A C7A 165.3(3) . . . . ?
C1 C6A C7A C8A -87.0(4) . . . . ?
C5 C6A C7A C8A 107.7(4) . . . . ?
C6A C7A C8A C9A 70.8(5) . . . . ?
C7A C8A C9A C10 176.5(4) . . . . ?
C7A C8A C9A C14 -16.9(7) . . . . ?
C14 C9A C10 C11 -1.5(4) . . . . ?
C8A C9A C10 C11 166.5(3) . . . . ?
C9A C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 N13 -0.1(5) . . . . ?
C11 C12 N13 C14 -0.2(5) . . . . ?
C12 N13 C14 C9A -0.4(4) . . . . ?
C12 N13 C14 C15 -178.3(3) . . . . ?
C10 C9A C14 N13 1.3(4) . . . . ?
C8A C9A C14 N13 -164.9(4) . . . . ?
C10 C9A C14 C15 179.0(2) . . . . ?
C8A C9A C14 C15 12.9(5) . . . . ?
C2 C1 C15 C16 61.0(4) . . . . ?
C6A C1 C15 C16 -120.5(3) . . . . ?
C2 C1 C15 C14 -117.5(3) . . . . ?
C6A C1 C15 C14 61.0(3) . . . . ?
N13 C14 C15 C16 -60.0(3) . . . . ?
C9A C14 C15 C16 122.1(3) . . . . ?
N13 C14 C15 C1 118.5(2) . . . . ?
C9A C14 C15 C1 -59.4(3) . . . . ?
C1 C15 C16 C21 0.5(4) . . . . ?
C14 C15 C16 C21 178.8(2) . . . . ?
C1 C15 C16 C17 175.9(2) . . . . ?
C14 C15 C16 C17 -5.8(4) . . . . ?
C15 C16 C17 C18 -120.8(3) . . . . ?
C21 C16 C17 C18 55.2(3) . . . . ?
C16 C17 C18 N19 -54.6(2) . . . . ?
C17 C18 N19 C22 -141.6(2) . . . . ?
C17 C18 N19 C20 54.7(3) . . . . ?
C22 N19 C20 C21 142.4(2) . . . . ?
C18 N19 C20 C21 -52.8(3) . . . . ?
C15 C16 C21 C20 123.0(3) . . . . ?
C17 C16 C21 C20 -52.9(3) . . . . ?
N19 C20 C21 C16 50.6(3) . . . . ?
C20 N19 C22 O23 -9.7(4) . . . . ?
C18 N19 C22 O23 -173.0(2) . . . . ?
C20 N19 C22 O24 171.31(19) . . . . ?
C18 N19 C22 O24 8.0(3) . . . . ?
O23 C22 O24 C25 -6.1(3) . . . . ?
N19 C22 O24 C25 172.96(19) . . . . ?
C22 O24 C25 C26 81.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.063
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene/TBME'
####################################################################### 
# 
# 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_GWO29a
_audit_block_doi                 10.5517/ccdc.csd.cc1zm8hc
_database_code_depnum_ccdc_archive 'CCDC 1835773'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8FD00072G 2018
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            loratadine-form1
_chemical_source_common          TOL/TBME
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Cl N2 O2'
_chemical_formula_weight         382.87

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   27.844(16)
_cell_length_b                   4.867(3)
_cell_length_c                   28.892(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.98(3)
_cell_angle_gamma                90.00
_cell_volume                     3703(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    10(2)
_cell_measurement_reflns_used    21880
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.7

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9029
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 loratadine disordered (0.51:0.49) 
;

_diffrn_ambient_temperature      10(2)
_diffrn_radiation_wavelength     0.711
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'beamline PXII SLS'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'one-circle goniometer'
_diffrn_measurement_method       φ-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19266
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3194
_reflns_number_gt                3115
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'DA+ (Wang, 2017)'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0343P)²+4.7924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0095(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3194
_refine_ls_number_parameters     293
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85097(4) 0.6035(3) 0.37077(4) 0.0111(3) Uani 1 1 d . D .
C2 C 0.88832(5) 0.4099(3) 0.37246(5) 0.0126(3) Uani 1 1 d . . .
H2 H 0.9036 0.3098 0.4018 0.015 Uiso 1 1 calc R . .
C3 C 0.90374(5) 0.3602(3) 0.33207(5) 0.0138(3) Uani 1 1 d . D .
H3 H 0.9291 0.2267 0.3334 0.017 Uiso 1 1 calc R . .
C4 C 0.88130(5) 0.5100(3) 0.28984(5) 0.0130(3) Uani 1 1 d . . .
C5 C 0.84433(5) 0.7061(3) 0.28697(4) 0.0125(3) Uani 1 1 d . D .
H5 H 0.8297 0.8073 0.2576 0.015 Uiso 1 1 calc R . .
C6 C 0.82877(5) 0.7535(3) 0.32758(4) 0.0112(3) Uani 1 1 d . . .
C7 C 0.78784(5) 0.9572(3) 0.32639(4) 0.0127(3) Uani 1 1 d . D .
H7A H 0.7826 1.0817 0.2981 0.015 Uiso 1 1 calc R . .
H7B H 0.7988 1.0699 0.3565 0.015 Uiso 1 1 calc R . .
C8 C 0.73766(5) 0.8143(3) 0.32247(4) 0.0125(3) Uani 1 1 d . . .
H8A H 0.7120 0.9584 0.3206 0.015 Uiso 1 1 calc R D .
H8B H 0.7263 0.7123 0.2911 0.015 Uiso 1 1 calc R . .
C9 C 0.73728(5) 0.6162(3) 0.36298(4) 0.0114(3) Uani 1 1 d . D .
C10 C 0.69091(5) 0.4915(3) 0.35864(5) 0.0128(3) Uani 1 1 d . . .
H10 H 0.6620 0.5327 0.3312 0.015 Uiso 1 1 calc R D .
C11 C 0.68634(5) 0.3091(3) 0.39364(5) 0.0140(3) Uani 1 1 d . D .
H11 H 0.6548 0.2228 0.3906 0.017 Uiso 1 1 calc R . .
C12 C 0.72934(5) 0.2564(3) 0.43342(5) 0.0136(3) Uani 1 1 d . . .
H12 H 0.7266 0.1325 0.4578 0.016 Uiso 1 1 calc R D .
N13 N 0.77442(4) 0.3714(2) 0.43904(4) 0.0124(2) Uani 1 1 d . D .
C14 C 0.77887(5) 0.5483(3) 0.40463(4) 0.0107(3) Uani 1 1 d . . .
C15 C 0.83205(5) 0.6496(3) 0.41308(4) 0.0114(3) Uani 1 1 d . D .
C16 C 0.86069(5) 0.7631(3) 0.45545(4) 0.0125(3) Uani 1 1 d . . .
C17 C 0.84254(5) 0.8283(3) 0.49816(4) 0.0134(3) Uani 1 1 d . C .
H17A H 0.8077 0.7561 0.4915 0.016 Uiso 1 1 calc R . .
H17B H 0.8415 1.0300 0.5022 0.016 Uiso 1 1 calc R . .
C18 C 0.87797(5) 0.7002(3) 0.54546(4) 0.0144(3) Uani 1 1 d . . .
H18A H 0.8678 0.7625 0.5736 0.017 Uiso 1 1 calc R A 1
H18B H 0.8749 0.4976 0.5434 0.017 Uiso 1 1 calc R A 1
C20 C 0.94921(5) 0.7082(3) 0.51300(4) 0.0141(3) Uani 1 1 d . . .
H20A H 0.9485 0.5063 0.5087 0.017 Uiso 1 1 calc R B 1
H20B H 0.9847 0.7713 0.5205 0.017 Uiso 1 1 calc R B 1
C21 C 0.91560(5) 0.8449(3) 0.46568(4) 0.0146(3) Uani 1 1 d . C .
H21A H 0.9189 1.0472 0.4689 0.017 Uiso 1 1 calc R . .
H21B H 0.9269 0.7880 0.4380 0.017 Uiso 1 1 calc R . .
N19A N 0.93078(4) 0.7789(2) 0.55330(4) 0.0147(3) Uani 0.514(5) 1 d PDU C 1
C22A C 0.9590(2) 0.9093(8) 0.59293(19) 0.0160(8) Uani 0.514(5) 1 d PDU C 1
O23A O 1.0026(2) 0.9774(11) 0.5989(2) 0.0149(9) Uani 0.514(5) 1 d PDU C 1
O24A O 0.93442(9) 0.9576(8) 0.62578(10) 0.0146(6) Uani 0.514(5) 1 d PDU C 1
C25A C 0.96473(11) 1.0980(6) 0.67004(13) 0.0147(8) Uani 0.514(5) 1 d PDU C 1
H25A H 0.9992 1.0168 0.6815 0.018 Uiso 0.514(5) 1 calc PR C 1
H25B H 0.9492 1.0697 0.6960 0.018 Uiso 0.514(5) 1 calc PR C 1
C26A C 0.96884(12) 1.4010(9) 0.66193(13) 0.0170(8) Uani 0.514(5) 1 d PDU C 1
H26A H 0.9863 1.4302 0.6379 0.026 Uiso 0.514(5) 1 calc PR C 1
H26B H 0.9881 1.4890 0.6929 0.026 Uiso 0.514(5) 1 calc PR C 1
H26C H 0.9348 1.4813 0.6497 0.026 Uiso 0.514(5) 1 calc PR C 1
N19B N 0.93078(4) 0.7789(2) 0.55330(4) 0.0147(3) Uani 0.486(5) 1 d PDU C 2
C22B C 0.9597(2) 0.9763(9) 0.58549(17) 0.0130(8) Uani 0.486(5) 1 d PDU C 2
O23B O 1.0025(2) 1.0520(12) 0.5893(2) 0.0169(10) Uani 0.486(5) 1 d PDU C 2
O24B O 0.93312(9) 1.0792(8) 0.61374(10) 0.0136(6) Uani 0.486(5) 1 d PDU C 2
C25B C 0.96029(12) 1.2745(10) 0.65132(13) 0.0148(8) Uani 0.486(5) 1 d PDU C 2
H25C H 0.9363 1.4157 0.6552 0.018 Uiso 0.486(5) 1 calc PR C 2
H25D H 0.9867 1.3681 0.6410 0.018 Uiso 0.486(5) 1 calc PR C 2
C26B C 0.98482(12) 1.1334(6) 0.69951(14) 0.0183(9) Uani 0.486(5) 1 d PDU C 2
H26D H 0.9591 1.0295 0.7086 0.027 Uiso 0.486(5) 1 calc PR C 2
H26E H 1.0002 1.2712 0.7247 0.027 Uiso 0.486(5) 1 calc PR C 2
H26F H 1.0112 1.0076 0.6966 0.027 Uiso 0.486(5) 1 calc PR C 2
Cl27 Cl 0.900356(11) 0.45135(7) 0.238568(10) 0.01568(13) Uani 1 1 d . D 2


_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
C1 C2 1.3926(19) . ?
C1 C6 1.4035(19) . ?
C1 C15 1.4971(18) . ?
C2 C3 1.3894(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 Cl27 1.7518(15) . ?
C5 C6 1.3958(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.5024(19) . ?
C7 C8 1.5315(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5191(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3947(19) . ?
C9 C14 1.4115(19) . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 N13 1.3353(18) . ?
C12 H12 0.9500 . ?
N13 C14 1.3508(18) . ?
C14 C15 1.5034(19) . ?
C15 C16 1.3435(19) . ?
C16 C17 1.5113(18) . ?
C16 C21 1.5131(19) . ?
C17 C18 1.5338(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N19A 1.4641(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C20 N19A 1.4580(17) . ?
C20 C21 1.5348(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
N19A C22A 1.321(6) . ?
C22A O23A 1.217(7) . ?
C22A O24A 1.358(6) . ?
O24A C25A 1.453(4) . ?
C25A C26A 1.503(5) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C22B O23B 1.218(7) . ?
C22B O24B 1.363(6) . ?
O24B C25B 1.456(5) . ?
C25B C26B 1.503(5) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 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
C2 C1 C6 119.42(12) . . ?
C2 C1 C15 121.99(11) . . ?
C6 C1 C15 118.54(12) . . ?
C3 C2 C1 121.31(12) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 118.32(13) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.94(12) . . ?
C3 C4 Cl27 119.05(11) . . ?
C5 C4 Cl27 119.00(10) . . ?
C4 C5 C6 119.40(12) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.60(12) . . ?
C5 C6 C7 122.02(11) . . ?
C1 C6 C7 118.37(11) . . ?
C6 C7 C8 111.65(11) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 117.78(11) . . ?
C9 C8 H8A 107.9 . . ?
C7 C8 H8A 107.9 . . ?
C9 C8 H8B 107.9 . . ?
C7 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
C10 C9 C14 116.98(12) . . ?
C10 C9 C8 116.43(11) . . ?
C14 C9 C8 126.59(12) . . ?
C11 C10 C9 121.09(12) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 117.70(12) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
N13 C12 C11 123.16(12) . . ?
N13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C12 N13 C14 119.03(11) . . ?
N13 C14 C9 122.04(12) . . ?
N13 C14 C15 114.26(11) . . ?
C9 C14 C15 123.59(12) . . ?
C16 C15 C1 122.92(12) . . ?
C16 C15 C14 122.98(11) . . ?
C1 C15 C14 114.07(11) . . ?
C15 C16 C17 124.98(12) . . ?
C15 C16 C21 123.29(12) . . ?
C17 C16 C21 111.72(11) . . ?
C16 C17 C18 110.69(11) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N19A C18 C17 110.73(11) . . ?
N19A C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
N19A C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
N19A C20 C21 109.75(11) . . ?
N19A C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
N19A C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C16 C21 C20 110.16(11) . . ?
C16 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C16 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C22A N19A C20 122.8(3) . . ?
C22A N19A C18 122.9(3) . . ?
C20 N19A C18 114.30(11) . . ?
O23A C22A N19A 122.6(6) . . ?
O23A C22A O24A 124.0(5) . . ?
N19A C22A O24A 113.4(4) . . ?
C22A O24A C25A 114.6(3) . . ?
O24A C25A C26A 112.1(4) . . ?
O24A C25A H25A 109.2 . . ?
C26A C25A H25A 109.2 . . ?
O24A C25A H25B 109.2 . . ?
C26A C25A H25B 109.2 . . ?
H25A C25A H25B 107.9 . . ?
O23B C22B O24B 122.7(6) . . ?
C22B O24B C25B 115.8(3) . . ?
O24B C25B C26B 111.2(4) . . ?
O24B C25B H25C 109.4 . . ?
C26B C25B H25C 109.4 . . ?
O24B C25B H25D 109.4 . . ?
C26B C25B H25D 109.4 . . ?
H25C C25B H25D 108.0 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.61(19) . . . . ?
C15 C1 C2 C3 176.87(12) . . . . ?
C1 C2 C3 C4 0.49(19) . . . . ?
C2 C3 C4 C5 0.10(19) . . . . ?
C2 C3 C4 Cl27 179.78(10) . . . . ?
C3 C4 C5 C6 -0.55(19) . . . . ?
Cl27 C4 C5 C6 179.76(9) . . . . ?
C4 C5 C6 C1 0.42(18) . . . . ?
C4 C5 C6 C7 -178.19(11) . . . . ?
C2 C1 C6 C5 0.15(18) . . . . ?
C15 C1 C6 C5 -177.42(11) . . . . ?
C2 C1 C6 C7 178.81(11) . . . . ?
C15 C1 C6 C7 1.25(17) . . . . ?
C5 C6 C7 C8 104.12(14) . . . . ?
C1 C6 C7 C8 -74.52(14) . . . . ?
C6 C7 C8 C9 59.85(14) . . . . ?
C7 C8 C9 C10 179.34(11) . . . . ?
C7 C8 C9 C14 0.03(19) . . . . ?
C14 C9 C10 C11 -0.27(19) . . . . ?
C8 C9 C10 C11 -179.64(12) . . . . ?
C9 C10 C11 C12 0.59(19) . . . . ?
C10 C11 C12 N13 -0.5(2) . . . . ?
C11 C12 N13 C14 0.09(19) . . . . ?
C12 N13 C14 C9 0.26(19) . . . . ?
C12 N13 C14 C15 -176.01(11) . . . . ?
C10 C9 C14 N13 -0.16(18) . . . . ?
C8 C9 C14 N13 179.14(12) . . . . ?
C10 C9 C14 C15 175.75(12) . . . . ?
C8 C9 C14 C15 -5.0(2) . . . . ?
C2 C1 C15 C16 68.86(19) . . . . ?
C6 C1 C15 C16 -113.64(15) . . . . ?
C2 C1 C15 C14 -109.03(14) . . . . ?
C6 C1 C15 C14 68.47(16) . . . . ?
N13 C14 C15 C16 -52.77(18) . . . . ?
C9 C14 C15 C16 131.03(14) . . . . ?
N13 C14 C15 C1 125.12(12) . . . . ?
C9 C14 C15 C1 -51.08(17) . . . . ?
C1 C15 C16 C17 176.45(12) . . . . ?
C14 C15 C16 C17 -5.8(2) . . . . ?
C1 C15 C16 C21 -2.7(2) . . . . ?
C14 C15 C16 C21 174.98(12) . . . . ?
C15 C16 C17 C18 127.01(14) . . . . ?
C21 C16 C17 C18 -53.74(15) . . . . ?
C16 C17 C18 N19A 52.75(15) . . . . ?
C15 C16 C21 C20 -125.30(14) . . . . ?
C17 C16 C21 C20 55.43(15) . . . . ?
N19A C20 C21 C16 -56.00(15) . . . . ?
C21 C20 N19A C22A -120.30(19) . . . . ?
C21 C20 N19A C18 58.02(15) . . . . ?
C17 C18 N19A C22A 121.77(19) . . . . ?
C17 C18 N19A C20 -56.55(15) . . . . ?
C20 N19A C22A O23A -0.8(3) . . . . ?
C18 N19A C22A O23A -179.0(2) . . . . ?
C20 N19A C22A O24A 179.38(18) . . . . ?
C18 N19A C22A O24A 1.2(2) . . . . ?
O23A C22A O24A C25A -0.5(4) . . . . ?
N19A C22A O24A C25A 179.3(3) . . . . ?
C22A O24A C25A C26A 77.9(3) . . . . ?
O23B C22B O24B C25B -3.8(4) . . . . ?
C22B O24B C25B C26B -94.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.059
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene/TBME'
####################################################################### 
# 
# 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_GWO11c
_audit_block_doi                 10.5517/ccdc.csd.cc1zm8c7
_database_code_depnum_ccdc_archive 'CCDC 1835769'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8FD00072G 2018
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            LoratadineI-p80(L13)
_chemical_source_common          ACN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Cl N2 O2'
_chemical_formula_weight         382.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   28.502(15)
_cell_length_b                   5.051(4)
_cell_length_c                   29.231(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.51(3)
_cell_angle_gamma                90.00
_cell_volume                     3966(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    353(2)
_cell_measurement_reflns_used    4407
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      65.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    1.853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4289
_exptl_absorpt_correction_T_max  0.9465
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      353(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19121
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         66.58
_reflns_number_total             3449
_reflns_number_gt                2434
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.630 (Bruker AXS, 2003)'
_computing_cell_refinement       'SAINT V7.36A (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT V7.36A (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1551P)²+3.8557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3449
_refine_ls_number_parameters     292
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.2792
_refine_ls_wR_factor_gt          0.2437
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.84944(12) 0.5700(7) 0.37012(12) 0.0657(8) Uani 1 1 d . . .
C2 C 0.88597(14) 0.3898(9) 0.37106(16) 0.0859(11) Uani 1 1 d . . .
H2 H 0.9008 0.2925 0.3992 0.103 Uiso 1 1 calc R . .
C3 C 0.90114(16) 0.3495(10) 0.33163(18) 0.0940(12) Uani 1 1 d . . .
H3 H 0.9257 0.2255 0.3329 0.113 Uiso 1 1 calc R . .
C4 C 0.87944(15) 0.4954(10) 0.29056(16) 0.0900(12) Uani 1 1 d . . .
C5 C 0.84326(15) 0.6768(9) 0.28825(14) 0.0864(11) Uani 1 1 d . . .
H5 H 0.8290 0.7742 0.2600 0.104 Uiso 1 1 calc R . .
C6 C 0.82764(12) 0.7165(7) 0.32797(12) 0.0705(9) Uani 1 1 d . . .
C7 C 0.78737(16) 0.9123(9) 0.32667(17) 0.0901(12) Uani 1 1 d . . .
H7A H 0.7991 1.0251 0.3551 0.108 Uiso 1 1 calc R . .
H7B H 0.7812 1.0240 0.2983 0.108 Uiso 1 1 calc R . .
C8 C 0.74018(16) 0.7894(10) 0.32537(17) 0.0952(12) Uani 1 1 d . . .
H8A H 0.7272 0.6941 0.2949 0.114 Uiso 1 1 calc R . .
H8B H 0.7169 0.9312 0.3244 0.114 Uiso 1 1 calc R . .
C9 C 0.73930(13) 0.6020(7) 0.36527(13) 0.0727(9) Uani 1 1 d . . .
C10 C 0.69343(15) 0.4941(10) 0.36161(17) 0.0943(13) Uani 1 1 d . . .
H10 H 0.6653 0.5431 0.3359 0.113 Uiso 1 1 calc R . .
C11 C 0.68887(16) 0.3170(11) 0.39517(18) 0.1017(14) Uani 1 1 d . . .
H11 H 0.6580 0.2475 0.3930 0.122 Uiso 1 1 calc R . .
C12 C 0.73063(16) 0.2451(10) 0.43181(17) 0.0980(13) Uani 1 1 d . . .
H12 H 0.7278 0.1198 0.4540 0.118 Uiso 1 1 calc R . .
N13 N 0.77568(12) 0.3455(7) 0.43754(12) 0.0860(9) Uani 1 1 d . . .
C14 C 0.78010(12) 0.5222(7) 0.40495(12) 0.0675(8) Uani 1 1 d . . .
C15 C 0.83221(12) 0.6146(7) 0.41264(12) 0.0687(9) Uani 1 1 d . . .
C16 C 0.86078(13) 0.7288(9) 0.45428(12) 0.0801(10) Uani 1 1 d . . .
C17 C 0.84469(14) 0.7952(10) 0.49694(14) 0.0894(12) Uani 1 1 d . C .
H17A H 0.8421 0.9860 0.4992 0.107 Uiso 1 1 calc R . .
H17B H 0.8120 0.7205 0.4918 0.107 Uiso 1 1 calc R . .
C18 C 0.87987(15) 0.6928(11) 0.54332(14) 0.0933(12) Uani 1 1 d . . .
H18A H 0.8703 0.7569 0.5702 0.112 Uiso 1 1 calc R A 1
H18B H 0.8787 0.5009 0.5434 0.112 Uiso 1 1 calc R A 1
C20 C 0.94737(15) 0.7029(11) 0.50958(15) 0.0974(13) Uani 1 1 d . . .
H20A H 0.9474 0.5114 0.5073 0.117 Uiso 1 1 calc R B 1
H20B H 0.9811 0.7652 0.5156 0.117 Uiso 1 1 calc R B 1
C21 C 0.91414(15) 0.8155(11) 0.46352(15) 0.0975(14) Uani 1 1 d . C .
H21A H 0.9249 0.7569 0.4370 0.117 Uiso 1 1 calc R . .
H21B H 0.9161 1.0072 0.4650 0.117 Uiso 1 1 calc R . .
N19A N 0.93070(12) 0.7811(8) 0.54924(12) 0.0948(10) Uani 0.524(10) 1 d PDU C 1
C22A C 0.9603(4) 0.9101(14) 0.5885(3) 0.0967(18) Uani 0.524(10) 1 d PDU C 1
O23A O 1.0027(3) 0.975(2) 0.5943(4) 0.100(3) Uani 0.524(10) 1 d PDU C 1
O24A O 0.9371(3) 0.9581(18) 0.6212(3) 0.0965(17) Uani 0.524(10) 1 d PDU C 1
C25A C 0.9664(4) 1.087(2) 0.6649(4) 0.112(2) Uani 0.524(10) 1 d PDU C 1
H25A H 1.0001 1.0184 0.6744 0.134 Uiso 0.524(10) 1 calc PR C 1
H25B H 0.9531 1.0425 0.6904 0.134 Uiso 0.524(10) 1 calc PR C 1
C26A C 0.9686(5) 1.373(2) 0.6618(5) 0.134(4) Uani 0.524(10) 1 d PDU C 1
H26A H 0.9954 1.4217 0.6506 0.201 Uiso 0.524(10) 1 calc PR C 1
H26B H 0.9740 1.4485 0.6933 0.201 Uiso 0.524(10) 1 calc PR C 1
H26C H 0.9378 1.4374 0.6395 0.201 Uiso 0.524(10) 1 calc PR C 1
N19B N 0.93070(12) 0.7811(8) 0.54924(12) 0.0948(10) Uani 0.476(10) 1 d PDU C 2
C22B C 0.9580(4) 0.9729(17) 0.5796(3) 0.0935(18) Uani 0.476(10) 1 d PDU C 2
O23B O 0.9972(5) 1.050(3) 0.5791(5) 0.111(3) Uani 0.476(10) 1 d PDU C 2
O24B O 0.9349(4) 1.062(2) 0.6099(3) 0.0988(19) Uani 0.476(10) 1 d PDU C 2
C25B C 0.9623(5) 1.244(3) 0.6465(4) 0.114(2) Uani 0.476(10) 1 d PDU C 2
H25C H 0.9883 1.3240 0.6367 0.137 Uiso 0.476(10) 1 calc PR C 2
H25D H 0.9402 1.3838 0.6495 0.137 Uiso 0.476(10) 1 calc PR C 2
C26B C 0.9842(8) 1.119(4) 0.6926(6) 0.176(7) Uani 0.476(10) 1 d PDU C 2
H26D H 0.9584 1.0507 0.7036 0.265 Uiso 0.476(10) 1 calc PR C 2
H26E H 1.0036 1.2466 0.7156 0.265 Uiso 0.476(10) 1 calc PR C 2
H26F H 1.0053 0.9771 0.6896 0.265 Uiso 0.476(10) 1 calc PR C 2
Cl27 Cl 0.89887(5) 0.4504(4) 0.24030(5) 0.1456(8) 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
C1 C2 1.376(5) . ?
C1 C6 1.393(5) . ?
C1 C15 1.498(5) . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(6) . ?
C4 Cl27 1.750(4) . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(6) . ?
C7 C8 1.470(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.509(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.387(6) . ?
C9 C14 1.400(5) . ?
C10 C11 1.366(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(7) . ?
C11 H11 0.9300 . ?
C12 N13 1.338(5) . ?
C12 H12 0.9300 . ?
N13 C14 1.342(5) . ?
C14 C15 1.500(5) . ?
C15 C16 1.348(5) . ?
C16 C17 1.503(6) . ?
C16 C21 1.518(5) . ?
C17 C18 1.484(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N19A 1.470(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 N19A 1.447(6) . ?
C20 C21 1.477(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
N19A C22A 1.343(9) . ?
C22A O23A 1.208(10) . ?
C22A O24A 1.353(10) . ?
O24A C25A 1.430(11) . ?
C25A C26A 1.446(14) . ?
C25A H25A 0.9700 . ?
C25A H25B 0.9700 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C22B O23B 1.189(11) . ?
C22B O24B 1.346(11) . ?
O24B C25B 1.427(12) . ?
C25B C26B 1.427(16) . ?
C25B H25C 0.9700 . ?
C25B H25D 0.9700 . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.7(3) . . ?
C2 C1 C15 122.6(3) . . ?
C6 C1 C15 118.8(3) . . ?
C3 C2 C1 121.9(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 Cl27 119.4(4) . . ?
C3 C4 Cl27 119.3(4) . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 121.9(3) . . ?
C1 C6 C7 118.8(3) . . ?
C8 C7 C6 114.0(4) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8A 107.4 . . ?
C9 C8 H8A 107.4 . . ?
C7 C8 H8B 107.4 . . ?
C9 C8 H8B 107.4 . . ?
H8A C8 H8B 106.9 . . ?
C10 C9 C14 116.8(4) . . ?
C10 C9 C8 116.5(3) . . ?
C14 C9 C8 126.7(3) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 118.2(4) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
N13 C12 C11 123.3(4) . . ?
N13 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C12 N13 C14 118.5(3) . . ?
N13 C14 C9 122.1(3) . . ?
N13 C14 C15 115.1(3) . . ?
C9 C14 C15 122.8(3) . . ?
C16 C15 C1 123.2(3) . . ?
C16 C15 C14 122.5(3) . . ?
C1 C15 C14 114.3(3) . . ?
C15 C16 C17 125.8(3) . . ?
C15 C16 C21 123.5(3) . . ?
C17 C16 C21 110.7(3) . . ?
C18 C17 C16 112.3(4) . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
N19A C18 C17 109.9(4) . . ?
N19A C18 H18A 109.7 . . ?
C17 C18 H18A 109.7 . . ?
N19A C18 H18B 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
N19A C20 C21 110.1(4) . . ?
N19A C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
N19A C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 C16 110.5(4) . . ?
C20 C21 H21A 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C22A N19A C20 122.4(6) . . ?
C22A N19A C18 124.1(6) . . ?
C20 N19A C18 113.4(3) . . ?
O23A C22A N19A 124.4(10) . . ?
O23A C22A O24A 123.5(9) . . ?
N19A C22A O24A 112.1(8) . . ?
C22A O24A C25A 115.9(8) . . ?
O24A C25A C26A 115.0(11) . . ?
O24A C25A H25A 108.5 . . ?
C26A C25A H25A 108.5 . . ?
O24A C25A H25B 108.5 . . ?
C26A C25A H25B 108.5 . . ?
H25A C25A H25B 107.5 . . ?
O23B C22B O24B 124.6(11) . . ?
C22B O24B C25B 116.3(9) . . ?
C26B C25B O24B 112.5(15) . . ?
C26B C25B H25C 109.1 . . ?
O24B C25B H25C 109.1 . . ?
C26B C25B H25D 109.1 . . ?
O24B C25B H25D 109.1 . . ?
H25C C25B H25D 107.8 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.5(6) . . . . ?
C15 C1 C2 C3 179.5(4) . . . . ?
C1 C2 C3 C4 0.6(7) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C2 C3 C4 Cl27 179.1(3) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
Cl27 C4 C5 C6 -179.5(3) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
C4 C5 C6 C7 -179.2(4) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C15 C1 C6 C5 -179.9(3) . . . . ?
C2 C1 C6 C7 179.5(3) . . . . ?
C15 C1 C6 C7 -0.4(5) . . . . ?
C5 C6 C7 C8 108.7(4) . . . . ?
C1 C6 C7 C8 -70.8(5) . . . . ?
C6 C7 C8 C9 57.7(6) . . . . ?
C7 C8 C9 C10 179.9(4) . . . . ?
C7 C8 C9 C14 -1.5(7) . . . . ?
C14 C9 C10 C11 -0.5(6) . . . . ?
C8 C9 C10 C11 178.3(4) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
C10 C11 C12 N13 2.2(8) . . . . ?
C11 C12 N13 C14 -1.4(7) . . . . ?
C12 N13 C14 C9 -0.5(6) . . . . ?
C12 N13 C14 C15 -177.1(4) . . . . ?
C10 C9 C14 N13 1.4(6) . . . . ?
C8 C9 C14 N13 -177.2(4) . . . . ?
C10 C9 C14 C15 177.7(4) . . . . ?
C8 C9 C14 C15 -0.9(6) . . . . ?
C2 C1 C15 C16 68.9(5) . . . . ?
C6 C1 C15 C16 -111.2(4) . . . . ?
C2 C1 C15 C14 -111.4(4) . . . . ?
C6 C1 C15 C14 68.6(4) . . . . ?
N13 C14 C15 C16 -57.3(5) . . . . ?
C9 C14 C15 C16 126.1(4) . . . . ?
N13 C14 C15 C1 123.0(4) . . . . ?
C9 C14 C15 C1 -53.6(5) . . . . ?
C1 C15 C16 C17 175.8(4) . . . . ?
C14 C15 C16 C17 -3.9(7) . . . . ?
C1 C15 C16 C21 -2.4(6) . . . . ?
C14 C15 C16 C21 177.9(4) . . . . ?
C15 C16 C17 C18 129.2(5) . . . . ?
C21 C16 C17 C18 -52.5(5) . . . . ?
C16 C17 C18 N19A 52.8(5) . . . . ?
N19A C20 C21 C16 -57.2(6) . . . . ?
C15 C16 C21 C20 -127.5(5) . . . . ?
C17 C16 C21 C20 54.1(6) . . . . ?
C21 C20 N19A C22A -123.4(5) . . . . ?
C21 C20 N19A C18 59.8(6) . . . . ?
C17 C18 N19A C22A 126.2(5) . . . . ?
C17 C18 N19A C20 -57.0(6) . . . . ?
C20 N19A C22A O23A 0.9(6) . . . . ?
C18 N19A C22A O23A 177.4(5) . . . . ?
C20 N19A C22A O24A -178.8(5) . . . . ?
C18 N19A C22A O24A -2.3(6) . . . . ?
O23A C22A O24A C25A -1.7(9) . . . . ?
N19A C22A O24A C25A 178.1(9) . . . . ?
C22A O24A C25A C26A 83.6(12) . . . . ?
O23B C22B O24B C25B -6.2(10) . . . . ?
C22B O24B C25B C26B -100.2(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.055
_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_GWO11e
_audit_block_doi                 10.5517/ccdc.csd.cc1zm8d8
_database_code_depnum_ccdc_archive 'CCDC 1835770'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8FD00072G 2018
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            LoratadineI-p25
_chemical_source_common          ACN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Cl N2 O2'
_chemical_formula_weight         382.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   28.301(4)
_cell_length_b                   4.998(1)
_cell_length_c                   29.154(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.217(6)
_cell_angle_gamma                90.00
_cell_volume                     3894(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6060
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      67.44

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    1.887
_exptl_absorpt_correction_type   muli-scan
_exptl_absorpt_correction_T_min  0.4233
_exptl_absorpt_correction_T_max  0.9456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18666
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         66.59
_reflns_number_total             3398
_reflns_number_gt                2777
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.630 (Bruker AXS, 2003)'
_computing_cell_refinement       'SAINT V7.36A (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT V7.36A (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0894P)²+3.8707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3398
_refine_ls_number_parameters     292
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1753
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.84977(8) 0.5874(5) 0.37025(8) 0.0480(5) Uani 1 1 d . D .
C2 C 0.88655(9) 0.4033(6) 0.37147(10) 0.0608(6) Uani 1 1 d . . .
H2 H 0.9013 0.3058 0.3997 0.073 Uiso 1 1 calc R . .
C3 C 0.90190(10) 0.3605(6) 0.33179(11) 0.0673(7) Uani 1 1 d . D .
H3 H 0.9265 0.2349 0.3330 0.081 Uiso 1 1 calc R . .
C4 C 0.88001(10) 0.5074(6) 0.29047(10) 0.0646(7) Uani 1 1 d . . .
C5 C 0.84372(10) 0.6929(6) 0.28798(9) 0.0611(7) Uani 1 1 d . D .
H5 H 0.8296 0.7913 0.2597 0.073 Uiso 1 1 calc R . .
C6 C 0.82783(9) 0.7345(5) 0.32795(8) 0.0509(6) Uani 1 1 d . . .
C7 C 0.78760(10) 0.9334(5) 0.32684(10) 0.0623(7) Uani 1 1 d . D .
H7A H 0.7820 1.0497 0.2989 0.075 Uiso 1 1 calc R . .
H7B H 0.7989 1.0436 0.3558 0.075 Uiso 1 1 calc R . .
C8 C 0.73904(10) 0.8009(6) 0.32421(10) 0.0645(7) Uani 1 1 d . . .
H8A H 0.7271 0.7040 0.2937 0.077 Uiso 1 1 calc R D .
H8B H 0.7149 0.9412 0.3228 0.077 Uiso 1 1 calc R . .
C9 C 0.73844(8) 0.6095(5) 0.36433(8) 0.0512(6) Uani 1 1 d . D .
C10 C 0.69263(10) 0.4954(6) 0.36068(11) 0.0673(7) Uani 1 1 d . . .
H10 H 0.6645 0.5408 0.3346 0.081 Uiso 1 1 calc R D .
C11 C 0.68808(10) 0.3178(7) 0.39458(11) 0.0741(8) Uani 1 1 d . D .
H11 H 0.6573 0.2426 0.3921 0.089 Uiso 1 1 calc R . .
C12 C 0.73031(10) 0.2539(6) 0.43234(11) 0.0697(8) Uani 1 1 d . . .
H12 H 0.7276 0.1308 0.4553 0.084 Uiso 1 1 calc R D .
N13 N 0.77507(8) 0.3594(5) 0.43786(8) 0.0614(6) Uani 1 1 d . D .
C14 C 0.77956(8) 0.5351(5) 0.40474(8) 0.0479(5) Uani 1 1 d . . .
C15 C 0.83173(8) 0.6318(5) 0.41261(8) 0.0488(5) Uani 1 1 d . D .
C16 C 0.86037(9) 0.7460(5) 0.45433(8) 0.0548(6) Uani 1 1 d . . .
C17 C 0.84354(9) 0.8092(6) 0.49698(9) 0.0592(6) Uani 1 1 d . C .
H17A H 0.8103 0.7361 0.4913 0.071 Uiso 1 1 calc R . .
H17B H 0.8416 1.0017 0.5002 0.071 Uiso 1 1 calc R . .
C18 C 0.87901(9) 0.6944(6) 0.54358(9) 0.0625(7) Uani 1 1 d . . .
H18A H 0.8695 0.7558 0.5709 0.075 Uiso 1 1 calc R A 1
H18B H 0.8769 0.5007 0.5425 0.075 Uiso 1 1 calc R A 1
C20 C 0.94760(10) 0.7068(7) 0.51019(10) 0.0680(7) Uani 1 1 d . . .
H20A H 0.9475 0.5137 0.5068 0.082 Uiso 1 1 calc R B 1
H20B H 0.9816 0.7697 0.5168 0.082 Uiso 1 1 calc R B 1
C21 C 0.91398(10) 0.8307(6) 0.46374(9) 0.0653(7) Uani 1 1 d . C .
H21A H 0.9247 0.7750 0.4368 0.078 Uiso 1 1 calc R . .
H21B H 0.9164 1.0241 0.4662 0.078 Uiso 1 1 calc R . .
N19A N 0.93038(8) 0.7776(5) 0.55017(7) 0.0661(6) Uani 0.548(8) 1 d PDU C 1
C22A C 0.9596(3) 0.9065(11) 0.5899(2) 0.0687(13) Uani 0.548(8) 1 d PDU C 1
O23A O 1.0024(3) 0.9719(18) 0.5959(3) 0.0755(19) Uani 0.548(8) 1 d PDU C 1
O24A O 0.9362(2) 0.9540(13) 0.62275(19) 0.0703(12) Uani 0.548(8) 1 d PDU C 1
C25A C 0.9657(3) 1.0824(14) 0.6669(2) 0.0789(16) Uani 0.548(8) 1 d PDU C 1
H25A H 0.9992 1.0078 0.6771 0.095 Uiso 0.548(8) 1 calc PR C 1
H25B H 0.9513 1.0441 0.6921 0.095 Uiso 0.548(8) 1 calc PR C 1
C26A C 0.9689(3) 1.3737(16) 0.6620(3) 0.096(2) Uani 0.548(8) 1 d PDU C 1
H26A H 0.9868 1.4133 0.6400 0.144 Uiso 0.548(8) 1 calc PR C 1
H26B H 0.9863 1.4507 0.6932 0.144 Uiso 0.548(8) 1 calc PR C 1
H26C H 0.9358 1.4475 0.6496 0.144 Uiso 0.548(8) 1 calc PR C 1
N19B N 0.93038(8) 0.7776(5) 0.55017(7) 0.0661(6) Uani 0.452(8) 1 d PDU C 2
C22B C 0.9581(4) 0.9694(14) 0.5811(3) 0.0654(15) Uani 0.452(8) 1 d PDU C 2
O23B O 0.9982(4) 1.048(2) 0.5819(4) 0.087(3) Uani 0.452(8) 1 d PDU C 2
O24B O 0.9339(3) 1.0593(15) 0.6110(2) 0.0707(14) Uani 0.452(8) 1 d PDU C 2
C25B C 0.9607(3) 1.244(2) 0.6482(3) 0.0840(18) Uani 0.452(8) 1 d PDU C 2
H25C H 0.9376 1.3791 0.6520 0.101 Uiso 0.452(8) 1 calc PR C 2
H25D H 0.9859 1.3344 0.6381 0.101 Uiso 0.452(8) 1 calc PR C 2
C26B C 0.9845(4) 1.117(2) 0.6945(4) 0.119(4) Uani 0.452(8) 1 d PDU C 2
H26D H 0.9598 1.0266 0.7047 0.179 Uiso 0.452(8) 1 calc PR C 2
H26E H 1.0010 1.2498 0.7181 0.179 Uiso 0.452(8) 1 calc PR C 2
H26F H 1.0087 0.9898 0.6914 0.179 Uiso 0.452(8) 1 calc PR C 2
Cl27 Cl 0.89940(3) 0.4594(3) 0.23989(3) 0.1032(4) Uani 1 1 d . D 2


_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
C1 C2 1.381(4) . ?
C1 C6 1.394(3) . ?
C1 C15 1.500(3) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 Cl27 1.751(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(4) . ?
C7 C8 1.505(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.516(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.388(4) . ?
C9 C14 1.406(3) . ?
C10 C11 1.366(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C12 N13 1.332(3) . ?
C12 H12 0.9300 . ?
N13 C14 1.342(3) . ?
C14 C15 1.498(3) . ?
C15 C16 1.347(3) . ?
C16 C17 1.504(4) . ?
C16 C21 1.511(3) . ?
C17 C18 1.511(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N19A 1.463(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 N19A 1.448(3) . ?
C20 C21 1.508(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
N19A C22A 1.346(7) . ?
C22A O23A 1.210(8) . ?
C22A O24A 1.351(8) . ?
O24A C25A 1.434(7) . ?
C25A C26A 1.469(10) . ?
C25A H25A 0.9700 . ?
C25A H25B 0.9700 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C22B O23B 1.194(10) . ?
C22B O24B 1.351(9) . ?
O24B C25B 1.438(10) . ?
C25B C26B 1.441(12) . ?
C25B H25C 0.9700 . ?
C25B H25D 0.9700 . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.1(2) . . ?
C2 C1 C15 122.4(2) . . ?
C6 C1 C15 118.5(2) . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 Cl27 119.1(2) . . ?
C3 C4 Cl27 119.3(2) . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 118.8(2) . . ?
C5 C6 C7 122.0(2) . . ?
C6 C7 C8 112.5(2) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 118.7(2) . . ?
C7 C8 H8A 107.6 . . ?
C9 C8 H8A 107.6 . . ?
C7 C8 H8B 107.6 . . ?
C9 C8 H8B 107.6 . . ?
H8A C8 H8B 107.1 . . ?
C10 C9 C14 116.8(2) . . ?
C10 C9 C8 116.6(2) . . ?
C14 C9 C8 126.6(2) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 117.9(3) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
N13 C12 C11 123.3(3) . . ?
N13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C12 N13 C14 118.9(2) . . ?
N13 C14 C9 121.8(2) . . ?
N13 C14 C15 115.0(2) . . ?
C9 C14 C15 123.0(2) . . ?
C16 C15 C14 123.0(2) . . ?
C16 C15 C1 122.7(2) . . ?
C14 C15 C1 114.30(19) . . ?
C15 C16 C17 125.1(2) . . ?
C15 C16 C21 123.6(2) . . ?
C17 C16 C21 111.3(2) . . ?
C16 C17 C18 111.5(2) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N19A C18 C17 110.3(2) . . ?
N19A C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N19A C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
N19A C20 C21 110.0(2) . . ?
N19A C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
N19A C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 C16 110.3(2) . . ?
C20 C21 H21A 109.6 . . ?
C16 C21 H21A 109.6 . . ?
C20 C21 H21B 109.6 . . ?
C16 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C22A N19A C20 122.4(4) . . ?
C22A N19A C18 123.5(4) . . ?
C20 N19A C18 114.1(2) . . ?
O23A C22A N19A 123.7(7) . . ?
O23A C22A O24A 123.4(7) . . ?
N19A C22A O24A 112.9(6) . . ?
C22A O24A C25A 116.0(5) . . ?
O24A C25A C26A 113.1(8) . . ?
O24A C25A H25A 109.0 . . ?
C26A C25A H25A 109.0 . . ?
O24A C25A H25B 109.0 . . ?
C26A C25A H25B 109.0 . . ?
H25A C25A H25B 107.8 . . ?
O23B C22B O24B 124.0(9) . . ?
C22B O24B C25B 116.6(7) . . ?
O24B C25B C26B 113.0(10) . . ?
O24B C25B H25C 109.0 . . ?
C26B C25B H25C 109.0 . . ?
O24B C25B H25D 109.0 . . ?
C26B C25B H25D 109.0 . . ?
H25C C25B H25D 107.8 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(4) . . . . ?
C15 C1 C2 C3 178.5(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 Cl27 179.2(2) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
Cl27 C4 C5 C6 -179.86(19) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C15 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C6 C7 179.7(2) . . . . ?
C15 C1 C6 C7 0.8(3) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C1 C6 C7 C8 -72.9(3) . . . . ?
C5 C6 C7 C8 107.0(3) . . . . ?
C6 C7 C8 C9 59.0(3) . . . . ?
C7 C8 C9 C10 179.1(3) . . . . ?
C7 C8 C9 C14 -1.2(4) . . . . ?
C14 C9 C10 C11 -0.6(4) . . . . ?
C8 C9 C10 C11 179.2(3) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 N13 1.1(5) . . . . ?
C11 C12 N13 C14 -0.7(5) . . . . ?
C12 N13 C14 C9 -0.3(4) . . . . ?
C12 N13 C14 C15 -177.0(2) . . . . ?
C10 C9 C14 N13 1.0(4) . . . . ?
C8 C9 C14 N13 -178.8(2) . . . . ?
C10 C9 C14 C15 177.3(2) . . . . ?
C8 C9 C14 C15 -2.5(4) . . . . ?
N13 C14 C15 C16 -55.3(3) . . . . ?
C9 C14 C15 C16 128.1(3) . . . . ?
N13 C14 C15 C1 123.9(2) . . . . ?
C9 C14 C15 C1 -52.7(3) . . . . ?
C2 C1 C15 C16 69.0(4) . . . . ?
C6 C1 C15 C16 -112.1(3) . . . . ?
C2 C1 C15 C14 -110.2(3) . . . . ?
C6 C1 C15 C14 68.7(3) . . . . ?
C14 C15 C16 C17 -4.3(4) . . . . ?
C1 C15 C16 C17 176.6(2) . . . . ?
C14 C15 C16 C21 176.6(2) . . . . ?
C1 C15 C16 C21 -2.6(4) . . . . ?
C15 C16 C17 C18 127.6(3) . . . . ?
C21 C16 C17 C18 -53.1(3) . . . . ?
C16 C17 C18 N19A 52.6(3) . . . . ?
N19A C20 C21 C16 -56.4(3) . . . . ?
C15 C16 C21 C20 -126.0(3) . . . . ?
C17 C16 C21 C20 54.7(3) . . . . ?
C21 C20 N19A C22A -122.0(3) . . . . ?
C21 C20 N19A C18 58.6(3) . . . . ?
C17 C18 N19A C22A 124.1(3) . . . . ?
C17 C18 N19A C20 -56.5(3) . . . . ?
C20 N19A C22A O23A -0.6(4) . . . . ?
C18 N19A C22A O23A 178.8(4) . . . . ?
C20 N19A C22A O24A 179.8(3) . . . . ?
C18 N19A C22A O24A -0.8(4) . . . . ?
O23A C22A O24A C25A -1.8(6) . . . . ?
N19A C22A O24A C25A 177.8(6) . . . . ?
C22A O24A C25A C26A 81.1(7) . . . . ?
O23B C22B O24B C25B -5.4(8) . . . . ?
C22B O24B C25B C26B -97.0(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.048
_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_GWO11b
_audit_block_doi                 10.5517/ccdc.csd.cc1zm8gb
_database_code_depnum_ccdc_archive 'CCDC 1835772'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8FD00072G 2018
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            LoratadineI-0deg(L13)
_chemical_source_common          ACN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Cl N2 O2'
_chemical_formula_weight         382.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   28.201(6)
_cell_length_b                   4.9720(10)
_cell_length_c                   29.106(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.077(10)
_cell_angle_gamma                90.00
_cell_volume                     3857.0(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7353
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      68.2

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    1.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4205
_exptl_absorpt_correction_T_max  0.9450
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17068
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         66.56
_reflns_number_total             3352
_reflns_number_gt                2881
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.630 (Bruker AXS, 2003)'
_computing_cell_refinement       'SAINT V7.36A (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT V7.36A (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0685P)²+3.6428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3352
_refine_ls_number_parameters     292
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.84997(7) 0.5958(4) 0.37028(7) 0.0402(4) Uani 1 1 d . D .
C2 C 0.88679(8) 0.4095(5) 0.37150(8) 0.0502(5) Uani 1 1 d . . .
H2 H 0.9015 0.3117 0.3998 0.060 Uiso 1 1 calc R . .
C3 C 0.90219(8) 0.3654(5) 0.33171(9) 0.0547(6) Uani 1 1 d . D .
H3 H 0.9268 0.2387 0.3330 0.066 Uiso 1 1 calc R . .
C4 C 0.88027(8) 0.5128(5) 0.29022(8) 0.0534(6) Uani 1 1 d . . .
C5 C 0.84384(8) 0.7004(5) 0.28777(7) 0.0506(5) Uani 1 1 d . D .
H5 H 0.8297 0.7988 0.2594 0.061 Uiso 1 1 calc R . .
C6 C 0.82799(7) 0.7435(4) 0.32781(7) 0.0420(5) Uani 1 1 d . . .
C7 C 0.78763(8) 0.9422(5) 0.32671(8) 0.0507(5) Uani 1 1 d . D .
H7A H 0.7822 1.0598 0.2989 0.061 Uiso 1 1 calc R . .
H7B H 0.7987 1.0523 0.3558 0.061 Uiso 1 1 calc R . .
C8 C 0.73869(8) 0.8070(5) 0.32377(8) 0.0520(5) Uani 1 1 d . . .
H8A H 0.7270 0.7099 0.2932 0.062 Uiso 1 1 calc R D .
H8B H 0.7143 0.9472 0.3223 0.062 Uiso 1 1 calc R . .
C9 C 0.73805(7) 0.6132(4) 0.36389(7) 0.0425(5) Uani 1 1 d . D .
C10 C 0.69230(8) 0.4965(5) 0.36014(8) 0.0544(6) Uani 1 1 d . . .
H10 H 0.6641 0.5397 0.3338 0.065 Uiso 1 1 calc R D .
C11 C 0.68780(9) 0.3186(6) 0.39450(9) 0.0616(6) Uani 1 1 d . D .
H11 H 0.6570 0.2416 0.3920 0.074 Uiso 1 1 calc R . .
C12 C 0.73013(9) 0.2577(5) 0.43264(9) 0.0574(6) Uani 1 1 d . . .
H12 H 0.7274 0.1351 0.4558 0.069 Uiso 1 1 calc R D .
N13 N 0.77484(6) 0.3656(4) 0.43809(6) 0.0502(4) Uani 1 1 d . D .
C14 C 0.77930(7) 0.5410(4) 0.40464(7) 0.0392(4) Uani 1 1 d . . .
C15 C 0.83160(7) 0.6397(4) 0.41260(7) 0.0402(4) Uani 1 1 d . D .
C16 C 0.86020(7) 0.7532(4) 0.45447(7) 0.0436(5) Uani 1 1 d . . .
C17 C 0.84308(8) 0.8149(5) 0.49711(7) 0.0472(5) Uani 1 1 d . C .
H17A H 0.8097 0.7423 0.4912 0.057 Uiso 1 1 calc R . .
H17B H 0.8414 1.0082 0.5007 0.057 Uiso 1 1 calc R . .
C18 C 0.87857(8) 0.6954(5) 0.54369(7) 0.0501(5) Uani 1 1 d . . .
H18A H 0.8690 0.7554 0.5711 0.060 Uiso 1 1 calc R A 1
H18B H 0.8762 0.5007 0.5422 0.060 Uiso 1 1 calc R A 1
C20 C 0.94769(8) 0.7085(6) 0.51037(8) 0.0553(6) Uani 1 1 d . . .
H20A H 0.9475 0.5147 0.5065 0.066 Uiso 1 1 calc R B 1
H20B H 0.9819 0.7713 0.5171 0.066 Uiso 1 1 calc R B 1
C21 C 0.91402(8) 0.8369(5) 0.46390(8) 0.0523(5) Uani 1 1 d . C .
H21A H 0.9167 1.0311 0.4667 0.063 Uiso 1 1 calc R . .
H21B H 0.9247 0.7821 0.4368 0.063 Uiso 1 1 calc R . .
N19A N 0.93025(6) 0.7773(4) 0.55060(6) 0.0533(5) Uani 0.552(7) 1 d PDU C 1
C22A C 0.9594(3) 0.9038(10) 0.5905(2) 0.0543(11) Uani 0.552(7) 1 d PDU C 1
O23A O 1.0024(2) 0.9691(16) 0.5963(3) 0.0633(16) Uani 0.552(7) 1 d PDU C 1
O24A O 0.93594(17) 0.9497(11) 0.62347(16) 0.0571(10) Uani 0.552(7) 1 d PDU C 1
C25A C 0.9657(2) 1.0816(12) 0.6677(2) 0.0633(13) Uani 0.552(7) 1 d PDU C 1
H25A H 0.9992 1.0058 0.6781 0.076 Uiso 0.552(7) 1 calc PR C 1
H25B H 0.9511 1.0460 0.6929 0.076 Uiso 0.552(7) 1 calc PR C 1
C26A C 0.9692(2) 1.3748(13) 0.6620(2) 0.0770(17) Uani 0.552(7) 1 d PDU C 1
H26A H 0.9874 1.4118 0.6401 0.116 Uiso 0.552(7) 1 calc PR C 1
H26B H 0.9864 1.4542 0.6931 0.116 Uiso 0.552(7) 1 calc PR C 1
H26C H 0.9361 1.4495 0.6493 0.116 Uiso 0.552(7) 1 calc PR C 1
N19B N 0.93025(6) 0.7773(4) 0.55060(6) 0.0533(5) Uani 0.448(7) 1 d PDU C 2
C22B C 0.9580(3) 0.9684(13) 0.5819(2) 0.0537(13) Uani 0.448(7) 1 d PDU C 2
O23B O 0.9987(4) 1.047(2) 0.5834(4) 0.074(2) Uani 0.448(7) 1 d PDU C 2
O24B O 0.9333(2) 1.0591(13) 0.6116(2) 0.0567(12) Uani 0.448(7) 1 d PDU C 2
C25B C 0.9598(3) 1.2483(19) 0.6487(2) 0.0700(16) Uani 0.448(7) 1 d PDU C 2
H25C H 0.9363 1.3812 0.6528 0.084 Uiso 0.448(7) 1 calc PR C 2
H25D H 0.9847 1.3413 0.6383 0.084 Uiso 0.448(7) 1 calc PR C 2
C26B C 0.9846(3) 1.1177(18) 0.6955(3) 0.095(3) Uani 0.448(7) 1 d PDU C 2
H26D H 0.9601 1.0241 0.7059 0.143 Uiso 0.448(7) 1 calc PR C 2
H26E H 1.0009 1.2512 0.7192 0.143 Uiso 0.448(7) 1 calc PR C 2
H26F H 1.0091 0.9920 0.6920 0.143 Uiso 0.448(7) 1 calc PR C 2
Cl27 Cl 0.89962(2) 0.4626(2) 0.23955(2) 0.0834(3) Uani 1 1 d . D 2


_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
C1 C2 1.383(3) . ?
C1 C6 1.396(3) . ?
C1 C15 1.500(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 Cl27 1.750(2) . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(3) . ?
C7 C8 1.512(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.519(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.386(3) . ?
C9 C14 1.409(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C12 N13 1.331(3) . ?
C12 H12 0.9300 . ?
N13 C14 1.343(3) . ?
C14 C15 1.499(3) . ?
C15 C16 1.346(3) . ?
C16 C17 1.503(3) . ?
C16 C21 1.510(3) . ?
C17 C18 1.518(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N19A 1.462(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 N19A 1.451(3) . ?
C20 C21 1.516(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
N19A C22A 1.339(7) . ?
C22A O23A 1.214(8) . ?
C22A O24A 1.351(7) . ?
O24A C25A 1.444(6) . ?
C25A C26A 1.474(8) . ?
C25A H25A 0.9700 . ?
C25A H25B 0.9700 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C22B O23B 1.202(10) . ?
C22B O24B 1.354(9) . ?
O24B C25B 1.442(9) . ?
C25B C26B 1.463(10) . ?
C25B H25C 0.9700 . ?
C25B H25D 0.9700 . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.16(19) . . ?
C2 C1 C15 122.29(18) . . ?
C6 C1 C15 118.53(18) . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 Cl27 119.19(18) . . ?
C3 C4 Cl27 119.32(18) . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.22(19) . . ?
C5 C6 C7 122.11(18) . . ?
C1 C6 C7 118.67(18) . . ?
C6 C7 C8 112.37(19) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 118.60(17) . . ?
C7 C8 H8A 107.7 . . ?
C9 C8 H8A 107.7 . . ?
C7 C8 H8B 107.7 . . ?
C9 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
C10 C9 C14 116.80(19) . . ?
C10 C9 C8 116.72(18) . . ?
C14 C9 C8 126.48(18) . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
N13 C12 C11 123.2(2) . . ?
N13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C12 N13 C14 118.99(18) . . ?
N13 C14 C9 121.89(18) . . ?
N13 C14 C15 114.90(17) . . ?
C9 C14 C15 123.13(18) . . ?
C16 C15 C14 123.05(17) . . ?
C16 C15 C1 122.60(17) . . ?
C14 C15 C1 114.33(16) . . ?
C15 C16 C17 125.03(18) . . ?
C15 C16 C21 123.34(19) . . ?
C17 C16 C21 111.63(17) . . ?
C16 C17 C18 111.20(17) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N19A C18 C17 110.50(17) . . ?
N19A C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
N19A C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
N19A C20 C21 110.00(19) . . ?
N19A C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
N19A C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C16 C21 C20 110.20(18) . . ?
C16 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C16 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C22A N19A C20 122.4(4) . . ?
C22A N19A C18 123.5(4) . . ?
C20 N19A C18 114.11(17) . . ?
O23A C22A N19A 123.3(6) . . ?
O23A C22A O24A 123.6(6) . . ?
N19A C22A O24A 113.0(5) . . ?
C22A O24A C25A 115.7(4) . . ?
O24A C25A C26A 113.0(6) . . ?
O24A C25A H25A 109.0 . . ?
C26A C25A H25A 109.0 . . ?
O24A C25A H25B 109.0 . . ?
C26A C25A H25B 109.0 . . ?
H25A C25A H25B 107.8 . . ?
O23B C22B O24B 123.7(8) . . ?
C22B O24B C25B 116.5(6) . . ?
O24B C25B C26B 112.3(9) . . ?
O24B C25B H25C 109.1 . . ?
C26B C25B H25C 109.1 . . ?
O24B C25B H25D 109.1 . . ?
C26B C25B H25D 109.1 . . ?
H25C C25B H25D 107.9 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(3) . . . . ?
C15 C1 C2 C3 177.9(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 Cl27 179.38(17) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
Cl27 C4 C5 C6 -179.91(16) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -178.8(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C15 C1 C6 C5 -178.52(18) . . . . ?
C2 C1 C6 C7 179.20(19) . . . . ?
C15 C1 C6 C7 1.0(3) . . . . ?
C5 C6 C7 C8 106.2(2) . . . . ?
C1 C6 C7 C8 -73.3(2) . . . . ?
C6 C7 C8 C9 59.1(3) . . . . ?
C7 C8 C9 C10 179.1(2) . . . . ?
C7 C8 C9 C14 -0.6(3) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 179.9(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 N13 1.0(4) . . . . ?
C11 C12 N13 C14 -0.6(4) . . . . ?
C12 N13 C14 C9 -0.2(3) . . . . ?
C12 N13 C14 C15 -176.9(2) . . . . ?
C10 C9 C14 N13 0.7(3) . . . . ?
C8 C9 C14 N13 -179.6(2) . . . . ?
C10 C9 C14 C15 177.02(19) . . . . ?
C8 C9 C14 C15 -3.2(3) . . . . ?
N13 C14 C15 C16 -54.3(3) . . . . ?
C9 C14 C15 C16 129.1(2) . . . . ?
N13 C14 C15 C1 124.36(19) . . . . ?
C9 C14 C15 C1 -52.2(3) . . . . ?
C2 C1 C15 C16 69.2(3) . . . . ?
C6 C1 C15 C16 -112.6(2) . . . . ?
C2 C1 C15 C14 -109.5(2) . . . . ?
C6 C1 C15 C14 68.7(2) . . . . ?
C14 C15 C16 C17 -4.6(3) . . . . ?
C1 C15 C16 C17 176.79(19) . . . . ?
C14 C15 C16 C21 176.0(2) . . . . ?
C1 C15 C16 C21 -2.6(3) . . . . ?
C15 C16 C17 C18 127.2(2) . . . . ?
C21 C16 C17 C18 -53.3(3) . . . . ?
C16 C17 C18 N19A 52.6(3) . . . . ?
C15 C16 C21 C20 -125.6(2) . . . . ?
C17 C16 C21 C20 54.9(3) . . . . ?
N19A C20 C21 C16 -56.1(3) . . . . ?
C21 C20 N19A C22A -121.9(3) . . . . ?
C21 C20 N19A C18 58.3(3) . . . . ?
C17 C18 N19A C22A 123.8(3) . . . . ?
C17 C18 N19A C20 -56.4(3) . . . . ?
C20 N19A C22A O23A -0.5(3) . . . . ?
C18 N19A C22A O23A 179.2(3) . . . . ?
C20 N19A C22A O24A 179.8(3) . . . . ?
C18 N19A C22A O24A -0.5(3) . . . . ?
O23A C22A O24A C25A -0.7(5) . . . . ?
N19A C22A O24A C25A 179.0(5) . . . . ?
C22A O24A C25A C26A 79.7(6) . . . . ?
O23B C22B O24B C25B -4.1(7) . . . . ?
C22B O24B C25B C26B -96.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        66.56
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.048
_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_GWO11d
_audit_block_doi                 10.5517/ccdc.csd.cc1zm8f9
_database_code_depnum_ccdc_archive 'CCDC 1835771'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8FD00072G 2018
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            LoratadineI-m173(L13)
_chemical_source_common          ACN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Cl N2 O2'
_chemical_formula_weight         382.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   27.906(4)
_cell_length_b                   4.8860(10)
_cell_length_c                   28.927(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.016(5)
_cell_angle_gamma                90.00
_cell_volume                     3728.9(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      68.2

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    1.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4103
_exptl_absorpt_correction_T_max  0.9432
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17727
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         66.59
_reflns_number_total             3249
_reflns_number_gt                3045
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.630 (Bruker AXS, 2003)'
_computing_cell_refinement       'SAINT V7.36A (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT V7.36A (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+5.1671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3249
_refine_ls_number_parameters     292
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85095(6) 0.6044(3) 0.37067(6) 0.0182(4) Uani 1 1 d . D .
C2 C 0.88815(6) 0.4117(4) 0.37240(6) 0.0210(4) Uani 1 1 d . . .
H2 H 0.9033 0.3118 0.4017 0.025 Uiso 1 1 calc R . .
C3 C 0.90354(6) 0.3626(4) 0.33212(6) 0.0225(4) Uani 1 1 d . D .
H3 H 0.9288 0.2294 0.3335 0.027 Uiso 1 1 calc R . .
C4 C 0.88133(6) 0.5118(4) 0.28996(6) 0.0219(4) Uani 1 1 d . . .
C5 C 0.84441(6) 0.7061(4) 0.28722(6) 0.0212(4) Uani 1 1 d . D .
H5 H 0.8298 0.8070 0.2579 0.025 Uiso 1 1 calc R . .
C6 C 0.82870(6) 0.7533(3) 0.32774(6) 0.0192(4) Uani 1 1 d . . .
C7 C 0.78793(7) 0.9553(4) 0.32639(6) 0.0215(4) Uani 1 1 d . D .
H7A H 0.7826 1.0784 0.2980 0.026 Uiso 1 1 calc R . .
H7B H 0.7990 1.0686 0.3564 0.026 Uiso 1 1 calc R . .
C8 C 0.73809(6) 0.8146(4) 0.32272(6) 0.0221(4) Uani 1 1 d . . .
H8A H 0.7126 0.9588 0.3209 0.026 Uiso 1 1 calc R D .
H8B H 0.7266 0.7132 0.2914 0.026 Uiso 1 1 calc R . .
C9 C 0.73749(6) 0.6170(3) 0.36315(6) 0.0190(4) Uani 1 1 d . D .
C10 C 0.69132(7) 0.4933(4) 0.35888(6) 0.0220(4) Uani 1 1 d . . .
H10 H 0.6624 0.5344 0.3314 0.026 Uiso 1 1 calc R D .
C11 C 0.68669(6) 0.3120(4) 0.39376(6) 0.0249(4) Uani 1 1 d . D .
H11 H 0.6552 0.2276 0.3908 0.030 Uiso 1 1 calc R . .
C12 C 0.72961(6) 0.2571(4) 0.43330(6) 0.0232(4) Uani 1 1 d . . .
H12 H 0.7269 0.1322 0.4575 0.028 Uiso 1 1 calc R D .
N13 N 0.77455(5) 0.3718(3) 0.43893(5) 0.0207(3) Uani 1 1 d . D .
C14 C 0.77905(6) 0.5481(3) 0.40462(6) 0.0176(3) Uani 1 1 d . . .
C15 C 0.83198(6) 0.6494(3) 0.41304(6) 0.0175(3) Uani 1 1 d . D .
C16 C 0.86074(6) 0.7628(3) 0.45538(6) 0.0196(4) Uani 1 1 d . . .
C17 C 0.84259(6) 0.8255(4) 0.49802(6) 0.0209(4) Uani 1 1 d . C .
H17A H 0.8080 0.7513 0.4914 0.025 Uiso 1 1 calc R . .
H17B H 0.8411 1.0263 0.5020 0.025 Uiso 1 1 calc R . .
C18 C 0.87812(6) 0.7002(4) 0.54517(6) 0.0225(4) Uani 1 1 d . . .
H18A H 0.8681 0.7629 0.5732 0.027 Uiso 1 1 calc R A 1
H18B H 0.8751 0.4983 0.5434 0.027 Uiso 1 1 calc R A 1
C20 C 0.94900(6) 0.7094(4) 0.51267(6) 0.0233(4) Uani 1 1 d . . .
H20A H 0.9486 0.5082 0.5084 0.028 Uiso 1 1 calc R B 1
H20B H 0.9844 0.7735 0.5201 0.028 Uiso 1 1 calc R B 1
C21 C 0.91537(7) 0.8440(4) 0.46552(6) 0.0228(4) Uani 1 1 d . C .
H21A H 0.9186 1.0455 0.4687 0.027 Uiso 1 1 calc R . .
H21B H 0.9266 0.7869 0.4379 0.027 Uiso 1 1 calc R . .
N19A N 0.93072(5) 0.7784(3) 0.55291(5) 0.0226(3) Uani 0.522(6) 1 d PDU C 1
C22A C 0.9592(2) 0.9092(9) 0.5927(2) 0.0233(10) Uani 0.522(6) 1 d PDU C 1
O23A O 1.0025(3) 0.9776(15) 0.5986(3) 0.0254(12) Uani 0.522(6) 1 d PDU C 1
O24A O 0.93471(11) 0.9560(9) 0.62545(12) 0.0226(7) Uani 0.522(6) 1 d PDU C 1
C25A C 0.96501(15) 1.0949(8) 0.66980(16) 0.0242(9) Uani 0.522(6) 1 d PDU C 1
H25A H 0.9995 1.0152 0.6811 0.029 Uiso 0.522(6) 1 calc PR C 1
H25B H 0.9496 1.0652 0.6958 0.029 Uiso 0.522(6) 1 calc PR C 1
C26A C 0.96857(17) 1.3940(11) 0.66176(17) 0.0286(11) Uani 0.522(6) 1 d PDU C 1
H26A H 0.9856 1.4243 0.6375 0.043 Uiso 0.522(6) 1 calc PR C 1
H26B H 0.9880 1.4819 0.6926 0.043 Uiso 0.522(6) 1 calc PR C 1
H26C H 0.9344 1.4727 0.6499 0.043 Uiso 0.522(6) 1 calc PR C 1
N19B N 0.93072(5) 0.7784(3) 0.55291(5) 0.0226(3) Uani 0.478(6) 1 d PDU C 2
C22B C 0.9593(3) 0.9748(11) 0.5849(2) 0.0222(11) Uani 0.478(6) 1 d PDU C 2
O23B O 1.0018(3) 1.0516(17) 0.5883(3) 0.0310(15) Uani 0.478(6) 1 d PDU C 2
O24B O 0.93312(12) 1.0768(10) 0.61353(13) 0.0219(8) Uani 0.478(6) 1 d PDU C 2
C25B C 0.95989(18) 1.2687(13) 0.65086(17) 0.0267(11) Uani 0.478(6) 1 d PDU C 2
H25C H 0.9358 1.4087 0.6547 0.032 Uiso 0.478(6) 1 calc PR C 2
H25D H 0.9861 1.3631 0.6405 0.032 Uiso 0.478(6) 1 calc PR C 2
C26B C 0.98456(17) 1.1314(9) 0.69889(18) 0.0302(11) Uani 0.478(6) 1 d PDU C 2
H26D H 0.9592 1.0259 0.7081 0.045 Uiso 0.478(6) 1 calc PR C 2
H26E H 0.9995 1.2701 0.7239 0.045 Uiso 0.478(6) 1 calc PR C 2
H26F H 1.0112 1.0083 0.6962 0.045 Uiso 0.478(6) 1 calc PR C 2
Cl27 Cl 0.900329(16) 0.45447(11) 0.238853(15) 0.03022(16) Uani 1 1 d . D 2


_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
C1 C2 1.390(2) . ?
C1 C6 1.398(2) . ?
C1 C15 1.501(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 Cl27 1.7481(17) . ?
C5 C6 1.398(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(2) . ?
C7 C8 1.524(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.392(2) . ?
C9 C14 1.411(2) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 N13 1.334(2) . ?
C12 H12 0.9500 . ?
N13 C14 1.350(2) . ?
C14 C15 1.500(2) . ?
C15 C16 1.346(2) . ?
C16 C21 1.509(2) . ?
C16 C17 1.510(2) . ?
C17 C18 1.529(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N19A 1.462(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C20 N19A 1.454(2) . ?
C20 C21 1.530(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
N19A C22A 1.330(6) . ?
C22A O23A 1.213(8) . ?
C22A O24A 1.355(7) . ?
O24A C25A 1.454(5) . ?
C25A C26A 1.488(6) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C22B O23B 1.217(8) . ?
C22B O24B 1.365(7) . ?
O24B C25B 1.441(7) . ?
C25B C26B 1.494(6) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 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
C2 C1 C6 119.67(15) . . ?
C2 C1 C15 121.85(15) . . ?
C6 C1 C15 118.43(15) . . ?
C3 C2 C1 121.24(16) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 118.50(16) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.58(16) . . ?
C3 C4 Cl27 119.29(14) . . ?
C5 C4 Cl27 119.13(14) . . ?
C4 C5 C6 119.74(16) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.27(16) . . ?
C5 C6 C7 122.02(15) . . ?
C1 C6 C7 118.70(15) . . ?
C6 C7 C8 111.90(14) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 118.12(14) . . ?
C9 C8 H8A 107.8 . . ?
C7 C8 H8A 107.8 . . ?
C9 C8 H8B 107.8 . . ?
C7 C8 H8B 107.8 . . ?
H8A C8 H8B 107.1 . . ?
C10 C9 C14 116.92(16) . . ?
C10 C9 C8 116.70(15) . . ?
C14 C9 C8 126.38(15) . . ?
C11 C10 C9 121.22(16) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 117.77(16) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
N13 C12 C11 122.99(16) . . ?
N13 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C12 N13 C14 119.14(15) . . ?
N13 C14 C9 121.96(15) . . ?
N13 C14 C15 114.42(14) . . ?
C9 C14 C15 123.53(15) . . ?
C16 C15 C14 123.18(15) . . ?
C16 C15 C1 122.61(15) . . ?
C14 C15 C1 114.18(13) . . ?
C15 C16 C21 123.41(15) . . ?
C15 C16 C17 124.60(15) . . ?
C21 C16 C17 111.99(14) . . ?
C16 C17 C18 110.78(14) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N19A C18 C17 111.04(14) . . ?
N19A C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
N19A C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N19A C20 C21 109.91(14) . . ?
N19A C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
N19A C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C16 C21 C20 110.35(14) . . ?
C16 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C16 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C22A N19A C20 122.6(3) . . ?
C22A N19A C18 123.0(3) . . ?
C20 N19A C18 114.41(13) . . ?
O23A C22A N19A 122.8(6) . . ?
O23A C22A O24A 124.1(6) . . ?
N19A C22A O24A 113.1(5) . . ?
C22A O24A C25A 114.5(3) . . ?
O24A C25A C26A 111.7(4) . . ?
O24A C25A H25A 109.3 . . ?
C26A C25A H25A 109.3 . . ?
O24A C25A H25B 109.3 . . ?
C26A C25A H25B 109.3 . . ?
H25A C25A H25B 107.9 . . ?
O23B C22B O24B 122.6(7) . . ?
C22B O24B C25B 116.3(4) . . ?
O24B C25B C26B 112.0(6) . . ?
O24B C25B H25C 109.2 . . ?
C26B C25B H25C 109.2 . . ?
O24B C25B H25D 109.2 . . ?
C26B C25B H25D 109.2 . . ?
H25C C25B H25D 107.9 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(2) . . . . ?
C15 C1 C2 C3 176.74(15) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 Cl27 179.71(13) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
Cl27 C4 C5 C6 179.74(12) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C5 C6 C7 -178.29(15) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C15 C1 C6 C5 -177.40(14) . . . . ?
C2 C1 C6 C7 178.70(15) . . . . ?
C15 C1 C6 C7 1.5(2) . . . . ?
C5 C6 C7 C8 104.56(18) . . . . ?
C1 C6 C7 C8 -74.26(19) . . . . ?
C6 C7 C8 C9 59.5(2) . . . . ?
C7 C8 C9 C10 179.58(15) . . . . ?
C7 C8 C9 C14 -0.1(3) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
C8 C9 C10 C11 -179.64(16) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 N13 0.2(3) . . . . ?
C11 C12 N13 C14 -0.5(3) . . . . ?
C12 N13 C14 C9 0.6(2) . . . . ?
C12 N13 C14 C15 -176.06(15) . . . . ?
C10 C9 C14 N13 -0.4(2) . . . . ?
C8 C9 C14 N13 179.27(15) . . . . ?
C10 C9 C14 C15 175.99(15) . . . . ?
C8 C9 C14 C15 -4.4(3) . . . . ?
N13 C14 C15 C16 -52.7(2) . . . . ?
C9 C14 C15 C16 130.67(18) . . . . ?
N13 C14 C15 C1 125.22(16) . . . . ?
C9 C14 C15 C1 -51.4(2) . . . . ?
C2 C1 C15 C16 69.1(2) . . . . ?
C6 C1 C15 C16 -113.73(19) . . . . ?
C2 C1 C15 C14 -108.86(17) . . . . ?
C6 C1 C15 C14 68.3(2) . . . . ?
C14 C15 C16 C21 174.87(16) . . . . ?
C1 C15 C16 C21 -2.9(3) . . . . ?
C14 C15 C16 C17 -5.5(3) . . . . ?
C1 C15 C16 C17 176.71(15) . . . . ?
C15 C16 C17 C18 127.33(18) . . . . ?
C21 C16 C17 C18 -53.02(19) . . . . ?
C16 C17 C18 N19A 52.05(19) . . . . ?
C15 C16 C21 C20 -125.43(18) . . . . ?
C17 C16 C21 C20 54.92(19) . . . . ?
N19A C20 C21 C16 -55.65(19) . . . . ?
C21 C20 N19A C22A -120.4(2) . . . . ?
C21 C20 N19A C18 57.6(2) . . . . ?
C17 C18 N19A C22A 122.0(2) . . . . ?
C17 C18 N19A C20 -56.0(2) . . . . ?
C20 N19A C22A O23A -0.9(3) . . . . ?
C18 N19A C22A O23A -178.8(3) . . . . ?
C20 N19A C22A O24A 179.3(2) . . . . ?
C18 N19A C22A O24A 1.4(3) . . . . ?
O23A C22A O24A C25A -0.8(4) . . . . ?
N19A C22A O24A C25A 179.0(4) . . . . ?
C22A O24A C25A C26A 78.3(4) . . . . ?
O23B C22B O24B C25B -4.2(5) . . . . ?
C22B O24B C25B C26B -94.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.057
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
