##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_database_code_depnum_ccdc_archive     'CCDC 1841284'
_chemical_name_systematic
;\
4-Amino-5-chloro-N-{(3RS,4SR)-1-[3-(4-fluorophenoxy)\
propyl]-3-methoxypiperidin-4-yl}-2-methoxybenzamide monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H29 Cl F N3 O4, H2 O'
_chemical_formula_sum     'C23 H31 Cl F N3 O5'
_chemical_formula_iupac     'C23 H29 Cl F N3 O4, H2 O'
_chemical_formula_weight     483.96
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     12.3225(9)
_cell_length_b     14.5183(8)
_cell_length_c     13.8141(8)
_cell_angle_alpha     90
_cell_angle_beta     98.361(2)
_cell_angle_gamma     90
_cell_volume     2445.1(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     11147
_cell_measurement_theta_min     3.18
_cell_measurement_theta_max     27.45
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'chunk'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.53
_exptl_crystal_size_mid     0.48
_exptl_crystal_size_min     0.4
_exptl_crystal_density_diffrn     1.315
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1024
_exptl_absorpt_coefficient_mu     0.202
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_shelx_estimated_absorpt_T_min     0.901
_shelx_estimated_absorpt_T_max     0.924
_exptl_absorpt_correction_T_min     0.9005
_exptl_absorpt_correction_T_max     0.9236
_exptl_special_details     ?
_diffrn_ambient_temperature     296.15
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19055
_diffrn_reflns_av_R_equivalents     0.0519
_diffrn_reflns_theta_min     3.178
_diffrn_reflns_theta_max     25.096
_diffrn_reflns_theta_full     25.096
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_refine_special_details     ?
_reflns_number_total     4348
_reflns_number_gt     2637
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1393
_refine_ls_R_factor_gt     0.0895
_refine_ls_wR_factor_gt     0.2136
_refine_ls_wR_factor_ref     0.2525
_refine_ls_goodness_of_fit_ref     1.000
_refine_ls_restrained_S_all     1.000
_refine_ls_number_reflns     4348
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.1051P)²+4.5913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.050
_refine_diff_density_min     -0.403
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_extinction_coef     0.0041(14)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
PROCESS-AUTO  (Rigaku, 2006)
;
_computing_cell_refinement
;
PROCESS-AUTO  (Rigaku, 2006)
;
_computing_data_reduction
;
CrystalStructure (Rigaku, 2007)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.4204(3) 0.2612(3) -0.0518(3) 0.0450(10) Uani d 1 . .
    C C2 0.4981(3) 0.3266(3) -0.0726(3) 0.0462(10) Uani d 1 . .
    C C3 0.5244(4) 0.3354(3) -0.1664(3) 0.0502(11) Uani d 1 . .
    H H3 0.575694 0.379382 -0.178535 0.060 Uiso calc 1 . .
    C C4 0.4757(4) 0.2798(3) -0.2432(3) 0.0481(11) Uani d 1 . .
    C C5 0.4001(4) 0.2146(3) -0.2214(3) 0.0525(11) Uani d 1 . .
    C C6 0.3742(4) 0.2057(3) -0.1289(3) 0.0522(11) Uani d 1 . .
    H H6 0.323756 0.160916 -0.117158 0.063 Uiso calc 1 . .
    C C7 0.6330(4) 0.4410(4) -0.0126(4) 0.0728(15) Uani d 1 . .
    H H7A 0.692127 0.406579 -0.033222 0.109 Uiso calc 1 . .
    H H7B 0.659091 0.472967 0.047110 0.109 Uiso calc 1 . .
    H H7C 0.605782 0.484757 -0.062330 0.109 Uiso calc 1 . .
    C C8 0.3783(4) 0.2478(3) 0.0429(3) 0.0500(11) Uani d 1 . .
    C C9 0.3665(4) 0.3025(3) 0.2090(3) 0.0539(12) Uani d 1 . .
    H H9 0.349898 0.238174 0.222715 0.065 Uiso calc 1 . .
    C C10 0.2618(4) 0.3571(4) 0.2051(3) 0.0586(13) Uani d 1 . .
    H H10A 0.207087 0.333192 0.153636 0.070 Uiso calc 1 . .
    H H10B 0.275416 0.421035 0.190438 0.070 Uiso calc 1 . .
    C C11 0.2193(4) 0.3506(4) 0.3030(3) 0.0619(13) Uani d 1 . .
    H H11A 0.151644 0.385323 0.299896 0.074 Uiso calc 1 . .
    H H11B 0.203447 0.286780 0.316341 0.074 Uiso calc 1 . .
    C C12 0.4033(4) 0.3359(4) 0.3875(3) 0.0618(13) Uani d 1 . .
    H H12A 0.391151 0.272511 0.405532 0.074 Uiso calc 1 . .
    H H12B 0.456561 0.362438 0.438508 0.074 Uiso calc 1 . .
    C C13 0.4505(4) 0.3368(3) 0.2918(3) 0.0551(12) Uani d 1 . .
    H H13 0.514764 0.296246 0.298025 0.066 Uiso calc 1 . .
    C C14 0.5809(5) 0.4596(5) 0.3175(5) 0.102(2) Uani d 1 . .
    H H14A 0.573519 0.463728 0.385592 0.154 Uiso calc 1 . .
    H H14B 0.596996 0.519388 0.293625 0.154 Uiso calc 1 . .
    H H14C 0.639420 0.417926 0.309413 0.154 Uiso calc 1 . .
    C C15 0.2584(5) 0.3771(4) 0.4777(3) 0.0758(16) Uani d 1 . .
    H H15A 0.230074 0.315205 0.482562 0.091 Uiso calc 1 . .
    H H15B 0.319074 0.385034 0.530237 0.091 Uiso calc 1 . .
    C C16 0.1723(6) 0.4431(7) 0.4908(5) 0.114(3) Uani d 1 . .
    H H16A 0.122584 0.445981 0.429638 0.137 Uiso calc 1 . .
    H H16B 0.206579 0.503191 0.500696 0.137 Uiso calc 1 . .
    C C17 0.1020(7) 0.4287(8) 0.5733(6) 0.140(3) Uani d 1 . .
    H H17A 0.052082 0.480078 0.575118 0.168 Uiso calc 1 . .
    H H17B 0.059017 0.372786 0.561479 0.168 Uiso calc 1 . .
    C C18 0.1157(5) 0.4117(4) 0.7409(4) 0.0697(15) Uani d 1 . .
    C C19 0.0074(6) 0.4256(4) 0.7456(4) 0.0838(18) Uani d 1 . .
    H H19 -0.039845 0.439471 0.688672 0.101 Uiso calc 1 . .
    C C20 -0.0347(5) 0.4195(4) 0.8349(5) 0.0827(17) Uani d 1 . .
    H H20 -0.108341 0.430685 0.838382 0.099 Uiso calc 1 . .
    C C21 0.0366(5) 0.3968(4) 0.9157(4) 0.0696(15) Uani d 1 . .
    C C22 0.1429(6) 0.3800(4) 0.9108(4) 0.0817(17) Uani d 1 . .
    H H22 0.189916 0.363008 0.966827 0.098 Uiso calc 1 . .
    C C23 0.1818(6) 0.3880(4) 0.8231(4) 0.0839(18) Uani d 1 . .
    H H23 0.255616 0.376737 0.820473 0.101 Uiso calc 1 . .
    Cl Cl1 0.33694(15) 0.14458(11) -0.31512(10) 0.0905(6) Uani d 1 . .
    F F1 -0.0006(4) 0.3878(3) 1.0038(2) 0.1087(13) Uani d 1 . .
    N N1 0.5026(3) 0.2899(3) -0.3347(3) 0.0668(12) Uani d 1 . .
    H H1A 0.472504 0.255336 -0.381597 0.080 Uiso calc 1 . .
    H H1B 0.549698 0.330941 -0.345663 0.080 Uiso calc 1 . .
    N N2 0.4117(3) 0.3047(3) 0.1171(3) 0.0574(10) Uani d 1 . .
    H H2 0.462014 0.344305 0.110529 0.069 Uiso calc 1 . .
    N N3 0.3000(3) 0.3867(3) 0.3827(2) 0.0523(10) Uani d 1 . .
    O O1 0.5470(3) 0.3796(2) 0.0033(2) 0.0608(9) Uani d 1 . .
    O O2 0.3121(3) 0.1858(2) 0.0507(2) 0.0728(11) Uani d 1 . .
    O O3 0.4820(3) 0.4267(2) 0.2644(2) 0.0611(9) Uani d 1 . .
    O O4 0.1677(4) 0.4224(4) 0.6572(3) 0.1035(15) Uani d 1 . .
    O O5 0.1856(4) 0.0853(3) 0.1649(3) 0.1034(16) Uani d 1 . .
    H H5A 0.220616 0.095952 0.119960 0.155 Uiso d 1 . .
    H H5B 0.189336 0.029332 0.156210 0.155 Uiso d 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.408(6) ?
    C1 C6 . 1.389(6) ?
    C1 C8 . 1.488(6) ?
    C2 C3 . 1.387(6) ?
    C2 O1 . 1.368(5) ?
    C3 H3 . 0.9300 ?
    C3 C4 . 1.397(6) ?
    C4 C5 . 1.392(6) ?
    C4 N1 . 1.361(5) ?
    C5 C6 . 1.367(6) ?
    C5 Cl1 . 1.739(4) ?
    C6 H6 . 0.9300 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C7 O1 . 1.426(6) ?
    C8 N2 . 1.335(5) ?
    C8 O2 . 1.230(5) ?
    C9 H9 . 0.9800 ?
    C9 C10 . 1.509(7) ?
    C9 C13 . 1.511(6) ?
    C9 N2 . 1.459(5) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C10 C11 . 1.523(6) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C11 N3 . 1.469(6) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C12 C13 . 1.521(6) ?
    C12 N3 . 1.464(6) ?
    C13 H13 . 0.9800 ?
    C13 O3 . 1.429(6) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C14 O3 . 1.410(6) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C15 C16 . 1.461(9) ?
    C15 N3 . 1.482(6) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C16 C17 . 1.542(10) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C17 O4 . 1.317(9) ?
    C18 C19 . 1.360(8) ?
    C18 C23 . 1.343(8) ?
    C18 O4 . 1.409(6) ?
    C19 H19 . 0.9300 ?
    C19 C20 . 1.409(8) ?
    C20 H20 . 0.9300 ?
    C20 C21 . 1.357(8) ?
    C21 C22 . 1.343(8) ?
    C21 F1 . 1.368(6) ?
    C22 H22 . 0.9300 ?
    C22 C23 . 1.372(7) ?
    C23 H23 . 0.9300 ?
    N1 H1A . 0.8600 ?
    N1 H1B . 0.8600 ?
    N2 H2 . 0.8600 ?
    O5 H5A . 0.8200 ?
    O5 H5B . 0.8231 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C8 . . 127.0(4) ?
    C6 C1 C2 . . 116.7(4) ?
    C6 C1 C8 . . 116.2(4) ?
    C3 C2 C1 . . 120.8(4) ?
    O1 C2 C1 . . 117.4(4) ?
    O1 C2 C3 . . 121.8(4) ?
    C2 C3 H3 . . 119.2 ?
    C2 C3 C4 . . 121.5(4) ?
    C4 C3 H3 . . 119.2 ?
    C5 C4 C3 . . 117.1(4) ?
    N1 C4 C3 . . 120.5(4) ?
    N1 C4 C5 . . 122.4(4) ?
    C4 C5 Cl1 . . 118.5(3) ?
    C6 C5 C4 . . 121.4(4) ?
    C6 C5 Cl1 . . 120.1(4) ?
    C1 C6 H6 . . 118.8 ?
    C5 C6 C1 . . 122.4(4) ?
    C5 C6 H6 . . 118.8 ?
    H7A C7 H7B . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O1 C7 H7A . . 109.5 ?
    O1 C7 H7B . . 109.5 ?
    O1 C7 H7C . . 109.5 ?
    N2 C8 C1 . . 119.1(4) ?
    O2 C8 C1 . . 119.6(4) ?
    O2 C8 N2 . . 121.3(4) ?
    C10 C9 H9 . . 107.8 ?
    C10 C9 C13 . . 110.0(4) ?
    C13 C9 H9 . . 107.8 ?
    N2 C9 H9 . . 107.8 ?
    N2 C9 C10 . . 113.0(4) ?
    N2 C9 C13 . . 110.2(4) ?
    C9 C10 H10A . . 109.7 ?
    C9 C10 H10B . . 109.7 ?
    C9 C10 C11 . . 109.8(4) ?
    H10A C10 H10B . . 108.2 ?
    C11 C10 H10A . . 109.7 ?
    C11 C10 H10B . . 109.7 ?
    C10 C11 H11A . . 109.4 ?
    C10 C11 H11B . . 109.4 ?
    H11A C11 H11B . . 108.0 ?
    N3 C11 C10 . . 111.2(4) ?
    N3 C11 H11A . . 109.4 ?
    N3 C11 H11B . . 109.4 ?
    H12A C12 H12B . . 107.7 ?
    C13 C12 H12A . . 108.9 ?
    C13 C12 H12B . . 108.9 ?
    N3 C12 H12A . . 108.9 ?
    N3 C12 H12B . . 108.9 ?
    N3 C12 C13 . . 113.3(4) ?
    C9 C13 C12 . . 110.4(4) ?
    C9 C13 H13 . . 108.9 ?
    C12 C13 H13 . . 108.9 ?
    O3 C13 C9 . . 106.5(4) ?
    O3 C13 C12 . . 113.0(4) ?
    O3 C13 H13 . . 108.9 ?
    H14A C14 H14B . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    O3 C14 H14A . . 109.5 ?
    O3 C14 H14B . . 109.5 ?
    O3 C14 H14C . . 109.5 ?
    H15A C15 H15B . . 107.7 ?
    C16 C15 H15A . . 108.9 ?
    C16 C15 H15B . . 108.9 ?
    C16 C15 N3 . . 113.5(5) ?
    N3 C15 H15A . . 108.9 ?
    N3 C15 H15B . . 108.9 ?
    C15 C16 H16A . . 107.3 ?
    C15 C16 H16B . . 107.3 ?
    C15 C16 C17 . . 119.9(7) ?
    H16A C16 H16B . . 106.9 ?
    C17 C16 H16A . . 107.3 ?
    C17 C16 H16B . . 107.3 ?
    C16 C17 H17A . . 110.0 ?
    C16 C17 H17B . . 110.0 ?
    H17A C17 H17B . . 108.3 ?
    O4 C17 C16 . . 108.7(7) ?
    O4 C17 H17A . . 110.0 ?
    O4 C17 H17B . . 110.0 ?
    C19 C18 O4 . . 126.1(5) ?
    C23 C18 C19 . . 118.4(5) ?
    C23 C18 O4 . . 115.4(6) ?
    C18 C19 H19 . . 119.3 ?
    C18 C19 C20 . . 121.4(5) ?
    C20 C19 H19 . . 119.3 ?
    C19 C20 H20 . . 121.4 ?
    C21 C20 C19 . . 117.3(6) ?
    C21 C20 H20 . . 121.4 ?
    C20 C21 F1 . . 119.6(6) ?
    C22 C21 C20 . . 121.5(5) ?
    C22 C21 F1 . . 118.8(5) ?
    C21 C22 H22 . . 120.1 ?
    C21 C22 C23 . . 119.8(6) ?
    C23 C22 H22 . . 120.1 ?
    C18 C23 C22 . . 121.5(6) ?
    C18 C23 H23 . . 119.3 ?
    C22 C23 H23 . . 119.3 ?
    C4 N1 H1A . . 120.0 ?
    C4 N1 H1B . . 120.0 ?
    H1A N1 H1B . . 120.0 ?
    C8 N2 C9 . . 122.7(4) ?
    C8 N2 H2 . . 118.6 ?
    C9 N2 H2 . . 118.6 ?
    C11 N3 C15 . . 110.2(4) ?
    C12 N3 C11 . . 110.1(4) ?
    C12 N3 C15 . . 108.8(4) ?
    C2 O1 C7 . . 119.2(4) ?
    C14 O3 C13 . . 114.8(4) ?
    C17 O4 C18 . . 115.8(6) ?
    H5A O5 H5B . . 91.7 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 C2 C3 C4 . . . . -0.4(7) ?
    C1 C2 O1 C7 . . . . 174.5(4) ?
    C1 C8 N2 C9 . . . . 173.6(4) ?
    C2 C1 C6 C5 . . . . -1.4(7) ?
    C2 C1 C8 N2 . . . . 3.2(7) ?
    C2 C1 C8 O2 . . . . -178.2(4) ?
    C2 C3 C4 C5 . . . . -0.4(6) ?
    C2 C3 C4 N1 . . . . 179.7(4) ?
    C3 C2 O1 C7 . . . . -4.5(6) ?
    C3 C4 C5 C6 . . . . 0.3(7) ?
    C3 C4 C5 Cl1 . . . . 179.5(3) ?
    C4 C5 C6 C1 . . . . 0.6(7) ?
    C6 C1 C2 C3 . . . . 1.3(6) ?
    C6 C1 C2 O1 . . . . -177.8(4) ?
    C6 C1 C8 N2 . . . . -173.8(4) ?
    C6 C1 C8 O2 . . . . 4.8(6) ?
    C8 C1 C2 C3 . . . . -175.7(4) ?
    C8 C1 C2 O1 . . . . 5.2(7) ?
    C8 C1 C6 C5 . . . . 175.9(4) ?
    C9 C10 C11 N3 . . . . 59.6(5) ?
    C9 C13 O3 C14 . . . . -162.6(4) ?
    C10 C9 C13 C12 . . . . 54.0(5) ?
    C10 C9 C13 O3 . . . . -69.0(4) ?
    C10 C9 N2 C8 . . . . -84.1(5) ?
    C10 C11 N3 C12 . . . . -58.2(5) ?
    C10 C11 N3 C15 . . . . -178.3(4) ?
    C12 C13 O3 C14 . . . . 76.0(6) ?
    C13 C9 C10 C11 . . . . -57.0(5) ?
    C13 C9 N2 C8 . . . . 152.4(4) ?
    C13 C12 N3 C11 . . . . 56.0(5) ?
    C13 C12 N3 C15 . . . . 176.9(4) ?
    C15 C16 C17 O4 . . . . 55.9(11) ?
    C16 C15 N3 C11 . . . . -74.1(6) ?
    C16 C15 N3 C12 . . . . 165.1(5) ?
    C16 C17 O4 C18 . . . . 178.2(6) ?
    C18 C19 C20 C21 . . . . -1.8(9) ?
    C19 C18 C23 C22 . . . . -1.7(10) ?
    C19 C18 O4 C17 . . . . -14.0(10) ?
    C19 C20 C21 C22 . . . . -0.5(9) ?
    C19 C20 C21 F1 . . . . -178.5(5) ?
    C20 C21 C22 C23 . . . . 1.6(9) ?
    C21 C22 C23 C18 . . . . -0.5(10) ?
    C23 C18 C19 C20 . . . . 2.8(9) ?
    C23 C18 O4 C17 . . . . 167.9(7) ?
    Cl1 C5 C6 C1 . . . . -178.5(4) ?
    F1 C21 C22 C23 . . . . 179.6(5) ?
    N1 C4 C5 C6 . . . . -179.8(4) ?
    N1 C4 C5 Cl1 . . . . -0.7(6) ?
    N2 C9 C10 C11 . . . . 179.4(4) ?
    N2 C9 C13 C12 . . . . 179.2(4) ?
    N2 C9 C13 O3 . . . . 56.2(5) ?
    N3 C12 C13 C9 . . . . -54.3(5) ?
    N3 C12 C13 O3 . . . . 64.8(5) ?
    N3 C15 C16 C17 . . . . 165.9(6) ?
    O1 C2 C3 C4 . . . . 178.7(4) ?
    O2 C8 N2 C9 . . . . -4.9(7) ?
    O4 C18 C19 C20 . . . . -175.2(5) ?
    O4 C18 C23 C22 . . . . 176.6(6) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1B O5 4_665 0.86 2.06 2.894(6) 163.7 yes
    N2 H2 O1 . 0.86 2.00 2.683(5) 135.4 yes
    O5 H5A O2 . 0.82 2.05 2.785(5) 149.1 yes
    O5 H5B N3 2_545 0.82 2.15 2.968(6) 173.8 yes
data_global
_journal_date_recd_electronic     2018-03-24
_journal_date_accepted     2018-05-03
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2018
_journal_volume     74
_journal_issue      6
_journal_page_first     690
_journal_page_last     695
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229618006836
_journal_coeditor_code     SK3687
_publ_contact_author_name     'Xiu-Rong Hu'
_publ_contact_author_address
;
Chemistry Department
Zhejiang University
Hangzhou
Zhejiang 310028
People's Republic of China
;
_publ_contact_author_email     huxiurong@zju.edu.cn
_publ_contact_author_phone     ?
_publ_section_title
;
A new polymorph of the gastrokinetic drug cisapride monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Xin-Bo Zhou'
;
Zhejiang Jingxin Pharmaceutical Co. Ltd
Xinchang
Zhejiang 312500
People's Republic of China
;
    'Jian-Rong Zhu'
;
Zhejiang Jingxin Pharmaceutical Co. Ltd
Xinchang
Zhejiang 312500
People's Republic of China
;
    'Jian-Ming Gu'
;
Chemistry Department
Zhejiang University
Hangzhou
Zhejiang 310028
People's Republic of China
;
    'Xiu-Rong Hu'
;
Chemistry Department
Zhejiang University
Hangzhou
Zhejiang 310028
People's Republic of China
;
_publ_section_synopsis
;
A new polymorph of cisapride monohydrate was obtained and characterized by
single-crystal X-ray diffraction. The molecular conformations, intermolecular
interactions, Hirshfeld surface analysis, crystal habit and relative stability
are compared between the new and a previously reported polymorph.
;
