# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx_a
_database_code_depnum_ccdc_archive 'CCDC 1585426'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-02-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_shelx_a             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
RESPONSE: Missing reflection is associated with reflection behind beam-stop.
;
# Added during the CSD deposition process: Tuesday 14 November 2017 06:08 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide hydrochloride oxalic acid'
_chemical_name_common            'Metoclopramide hydrochloride oxalic acid'
_chemical_melting_point          416
_chemical_formula_moiety         'C14 H23 Cl N3 O2, 0.5(C2 H2 O4), Cl'
_chemical_formula_sum            'C15 H24 Cl2 N3 O4'
_chemical_formula_weight         381.27

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   7.5270(4)
_cell_length_b                   14.1483(9)
_cell_length_c                   34.3682(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3660.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    32557
_cell_measurement_theta_min      3.114
_cell_measurement_theta_max      27.457

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.379
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'abscor, T.Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       \wscan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            32551
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4170
_reflns_number_gt                3418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'RAPID-AUTO (Rigaku, 2009)'
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2009)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2009)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.6278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4170
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.10497(5) 0.48204(3) 0.15636(2) 0.01734(11) Uani 1 1 d . . . . .
H1A H 0.081(3) 0.2364(16) 0.1809(6) 0.022(5) Uiso 1 1 d . . . . .
H1B H 0.060(3) 0.3171(15) 0.1548(6) 0.022(5) Uiso 1 1 d . . . . .
O1 O -0.02415(16) 0.32479(8) 0.31399(3) 0.0155(2) Uani 1 1 d . . . . .
O2 O -0.16039(16) 0.60676(8) 0.29792(3) 0.0184(3) Uani 1 1 d . . . . .
H2 H -0.132(3) 0.4326(17) 0.3467(6) 0.027(6) Uiso 1 1 d . . . . .
N1 N 0.02346(19) 0.28683(10) 0.17473(4) 0.0151(3) Uani 1 1 d . . . . .
N2 N -0.14334(19) 0.48899(10) 0.34201(4) 0.0141(3) Uani 1 1 d . . . . .
N3 N 0.02307(18) 0.65730(9) 0.41918(4) 0.0122(3) Uani 1 1 d . . . . .
H3 H -0.066(3) 0.6956(15) 0.4148(5) 0.018(5) Uiso 1 1 d . . . . .
C1 C -0.0162(2) 0.34166(11) 0.20664(4) 0.0120(3) Uani 1 1 d . . . . .
C2 C -0.0791(2) 0.43465(11) 0.20302(4) 0.0125(3) Uani 1 1 d . . . . .
C3 C -0.1186(2) 0.48902(11) 0.23514(5) 0.0131(3) Uani 1 1 d . . . . .
H3A H -0.159489 0.551953 0.231558 0.016 Uiso 1 1 calc R U . . .
C4 C -0.0999(2) 0.45351(11) 0.27291(4) 0.0123(3) Uani 1 1 d . . . . .
C5 C -0.0411(2) 0.35897(11) 0.27695(4) 0.0120(3) Uani 1 1 d . . . . .
C6 C -0.0005(2) 0.30470(11) 0.24448(4) 0.0123(3) Uani 1 1 d . . . . .
H6 H 0.038567 0.241402 0.247883 0.015 Uiso 1 1 calc R U . . .
C7 C 0.0347(2) 0.22915(11) 0.31910(5) 0.0152(3) Uani 1 1 d . . . . .
H7A H 0.032696 0.213065 0.346829 0.023 Uiso 1 1 calc R U . . .
H7B H 0.156018 0.222644 0.309103 0.023 Uiso 1 1 calc R U . . .
H7C H -0.044442 0.186396 0.304849 0.023 Uiso 1 1 calc R U . . .
C8 C -0.1362(2) 0.52158(11) 0.30512(4) 0.0129(3) Uani 1 1 d . . . . .
C9 C -0.1613(2) 0.55279(11) 0.37492(4) 0.0141(3) Uani 1 1 d . . . . .
H9A H -0.218374 0.519685 0.397009 0.017 Uiso 1 1 calc R U . . .
H9B H -0.236260 0.607545 0.367678 0.017 Uiso 1 1 calc R U . . .
C10 C 0.0246(2) 0.58638(11) 0.38653(4) 0.0134(3) Uani 1 1 d . . . . .
H10A H 0.096201 0.530997 0.394538 0.016 Uiso 1 1 calc R U . . .
H10B H 0.082877 0.615059 0.363564 0.016 Uiso 1 1 calc R U . . .
C11 C 0.1876(2) 0.71896(11) 0.41833(5) 0.0148(3) Uani 1 1 d . . . . .
H11A H 0.172197 0.771561 0.437023 0.018 Uiso 1 1 calc R U . . .
H11B H 0.200154 0.746757 0.392034 0.018 Uiso 1 1 calc R U . . .
C12 C 0.3562(2) 0.66557(12) 0.42834(5) 0.0186(3) Uani 1 1 d . . . . .
H12A H 0.349737 0.643244 0.455297 0.028 Uiso 1 1 calc R U . . .
H12B H 0.458789 0.707625 0.425374 0.028 Uiso 1 1 calc R U . . .
H12C H 0.369121 0.611347 0.410825 0.028 Uiso 1 1 calc R U . . .
C13 C -0.0093(2) 0.61045(11) 0.45789(4) 0.0156(3) Uani 1 1 d . . . . .
H13A H 0.089089 0.565919 0.463300 0.019 Uiso 1 1 calc R U . . .
H13B H -0.120593 0.573316 0.456402 0.019 Uiso 1 1 calc R U . . .
C14 C -0.0235(2) 0.68027(12) 0.49130(5) 0.0191(3) Uani 1 1 d . . . . .
H14A H -0.058735 0.646739 0.515025 0.029 Uiso 1 1 calc R U . . .
H14B H -0.112830 0.728315 0.485024 0.029 Uiso 1 1 calc R U . . .
H14C H 0.091813 0.710818 0.495397 0.029 Uiso 1 1 calc R U . . .
O3 O -0.17051(15) 0.94567(8) 0.47381(4) 0.0183(3) Uani 1 1 d . . . . .
O4 O 0.12581(17) 0.93201(9) 0.46783(4) 0.0275(3) Uani 1 1 d . . . . .
C15 C -0.0044(2) 0.96410(11) 0.48297(5) 0.0154(3) Uani 1 1 d . . . . .
H3B H -0.175(3) 0.9045(19) 0.4537(8) 0.046(7) Uiso 1 1 d . . . . .
Cl2 Cl -0.25605(5) 0.81646(3) 0.40917(2) 0.01442(10) 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
Cl1 C2 1.7488(16) . ?
O1 C5 1.3677(18) . ?
O1 C7 1.4347(19) . ?
O2 C8 1.244(2) . ?
N1 C1 1.376(2) . ?
N1 H1A 0.86(2) . ?
N1 H1B 0.85(2) . ?
N2 C8 1.350(2) . ?
N2 C9 1.4535(19) . ?
N2 H2 0.82(2) . ?
N3 C10 1.5055(19) . ?
N3 C13 1.5063(19) . ?
N3 C11 1.515(2) . ?
N3 H3 0.88(2) . ?
C1 C2 1.404(2) . ?
C1 C6 1.407(2) . ?
C2 C3 1.378(2) . ?
C3 C4 1.399(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.416(2) . ?
C4 C8 1.492(2) . ?
C5 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.531(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.518(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O3 C15 1.316(2) . ?
O3 H3B 0.90(3) . ?
O4 C15 1.199(2) . ?
C15 C15 1.552(3) 5_576 ?

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
C5 O1 C7 118.44(12) . . ?
C1 N1 H1A 112.4(14) . . ?
C1 N1 H1B 115.2(14) . . ?
H1A N1 H1B 117(2) . . ?
C8 N2 C9 121.50(14) . . ?
C8 N2 H2 120.9(16) . . ?
C9 N2 H2 117.5(16) . . ?
C10 N3 C13 111.48(12) . . ?
C10 N3 C11 111.29(12) . . ?
C13 N3 C11 113.76(12) . . ?
C10 N3 H3 106.8(13) . . ?
C13 N3 H3 107.5(13) . . ?
C11 N3 H3 105.5(13) . . ?
N1 C1 C2 122.07(14) . . ?
N1 C1 C6 120.60(14) . . ?
C2 C1 C6 117.30(14) . . ?
C3 C2 C1 121.67(14) . . ?
C3 C2 Cl1 119.76(12) . . ?
C1 C2 Cl1 118.57(12) . . ?
C2 C3 C4 121.40(14) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C5 117.50(14) . . ?
C3 C4 C8 115.97(14) . . ?
C5 C4 C8 126.46(14) . . ?
O1 C5 C6 122.14(14) . . ?
O1 C5 C4 117.03(13) . . ?
C6 C5 C4 120.82(14) . . ?
C5 C6 C1 121.27(14) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N2 120.79(14) . . ?
O2 C8 C4 120.30(14) . . ?
N2 C8 C4 118.91(14) . . ?
N2 C9 C10 108.08(13) . . ?
N2 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
N2 C9 H9B 110.1 . . ?
C10 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
N3 C10 C9 113.22(12) . . ?
N3 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N3 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N3 C11 C12 113.13(13) . . ?
N3 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 113.13(13) . . ?
N3 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N3 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 O3 H3B 110.3(17) . . ?
O4 C15 O3 126.72(15) . . ?
O4 C15 C15 122.74(19) . 5_576 ?
O3 C15 C15 110.53(17) . 5_576 ?

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
N1 C1 C2 C3 179.95(15) . . . . ?
C6 C1 C2 C3 2.1(2) . . . . ?
N1 C1 C2 Cl1 -0.7(2) . . . . ?
C6 C1 C2 Cl1 -178.61(11) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
Cl1 C2 C3 C4 179.89(12) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C2 C3 C4 C8 176.28(14) . . . . ?
C7 O1 C5 C6 -1.1(2) . . . . ?
C7 O1 C5 C4 179.85(13) . . . . ?
C3 C4 C5 O1 -179.65(13) . . . . ?
C8 C4 C5 O1 3.5(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C8 C4 C5 C6 -175.60(14) . . . . ?
O1 C5 C6 C1 -178.99(14) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
N1 C1 C6 C5 -179.61(14) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
C9 N2 C8 O2 -6.4(2) . . . . ?
C9 N2 C8 C4 174.08(14) . . . . ?
C3 C4 C8 O2 -8.2(2) . . . . ?
C5 C4 C8 O2 168.74(15) . . . . ?
C3 C4 C8 N2 171.40(14) . . . . ?
C5 C4 C8 N2 -11.7(2) . . . . ?
C8 N2 C9 C10 -85.75(18) . . . . ?
C13 N3 C10 C9 76.56(16) . . . . ?
C11 N3 C10 C9 -155.26(13) . . . . ?
N2 C9 C10 N3 176.96(12) . . . . ?
C10 N3 C11 C12 -68.66(16) . . . . ?
C13 N3 C11 C12 58.28(17) . . . . ?
C10 N3 C13 C14 -176.34(13) . . . . ?
C11 N3 C13 C14 56.81(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O2 0.86(2) 2.06(2) 2.9046(19) 165.7(19) 4_545 yes
N1 H1B Cl1 0.85(2) 2.64(2) 2.9936(15) 106.1(16) . yes
N1 H1B Cl2 0.85(2) 2.65(2) 3.3993(15) 147.5(18) 4_545 yes
N2 H2 O1 0.82(2) 2.06(2) 2.6701(18) 131(2) . yes
N2 H2 Cl2 0.82(2) 2.83(2) 3.4438(15) 133.2(19) 7 yes
N3 H3 Cl2 0.88(2) 2.24(2) 3.0988(14) 167.8(18) . yes
O3 H3B Cl2 0.90(3) 2.07(3) 2.9481(13) 165(2) . yes
C3 H3A O2 0.95 2.41 2.7439(19) 100.4 . yes
C7 H7C O2 0.98 2.50 3.386(2) 149.9 7 yes
C11 H11A O4 0.99 2.53 3.492(2) 164.3 . yes
C12 H12B Cl2 0.98 2.70 3.6754(17) 173.8 1_655 yes
C13 H13B O3 0.99 2.47 3.397(2) 156.2 7 yes

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.108


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1585430'
_audit_update_record             
;
2017-12-12 deposited with the CCDC.
2018-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'4-Amino-5-chloro-N-((2-diethylamino)-ethyl)-2-methoxybenzamide hydrochloride monohydrate'
_chemical_name_common            'Metoclopramide HCl Monohydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H23 Cl N3 O2, Cl, H2 O'
_chemical_formula_sum            'C14 H25 Cl2 N3 O3'
_chemical_formula_weight         354.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.1124(17)
_cell_length_b                   8.5524(12)
_cell_length_c                   16.849(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.605(7)
_cell_angle_gamma                90
_cell_volume                     1725.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17713
_cell_measurement_theta_min      3.072
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.182
_exptl_absorpt_coefficient_mu    0.391
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   'abscor, T. Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with SHINE monochromator X-ray'
_diffrn_measurement_device_type  'RIGAKU XtaLab'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            17713
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3954
_reflns_number_gt                3386
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'RIGAKU CrystalClear-SM Expert2.0 r4'
_computing_cell_refinement       'RIGAKU CrystalClear-SM Expert2.0 r4'
_computing_data_reduction        'RIGAKU CrystalClear-SM Expert2.0 r4'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²+0.6960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3954
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44426(8) 0.32792(12) 0.54043(6) 0.0260(2) Uani 1 1 d . . . . .
H1A H 0.6089(16) -0.009(2) 0.3553(10) 0.036(5) Uiso 1 1 d . . . . .
H1B H 0.5239(15) -0.086(2) 0.2995(11) 0.036(5) Uiso 1 1 d . . . . .
C1 C 0.46120(11) 0.06070(15) 0.36981(8) 0.0222(3) Uani 1 1 d . . . . .
N1 N 0.53892(11) -0.01957(16) 0.33655(8) 0.0299(3) Uani 1 1 d . . . . .
Cl2 Cl 0.20182(3) -0.07218(4) 0.60419(2) 0.03058(10) Uani 1 1 d . . . . .
H2 H 0.2901(14) 0.3546(19) 0.5784(10) 0.029(4) Uiso 1 1 d . . . . .
C2 C 0.34667(11) 0.05333(16) 0.33959(8) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.22460(10) 0.35815(14) 0.55235(7) 0.0229(2) Uani 1 1 d . . . . .
O2 O 0.11081(8) 0.30504(14) 0.43764(6) 0.0333(3) Uani 1 1 d . . . . .
O3 O -0.03618(12) 0.25685(14) 0.29789(7) 0.0371(3) Uani 1 1 d . . . . .
H3C H -0.0882(19) 0.213(3) 0.3197(13) 0.063(7) Uiso 1 1 d . . . . .
H3B H 0.0110(18) 0.273(2) 0.3343(13) 0.052(6) Uiso 1 1 d . . . . .
H3 H 0.1091(14) 0.133(2) 0.6333(9) 0.030(4) Uiso 1 1 d . . . . .
C3 C 0.26925(11) 0.13252(16) 0.37582(8) 0.0224(3) Uani 1 1 d . . . . .
H3A H 0.192580 0.124698 0.353671 0.027 Uiso 1 1 calc R U . . .
N3 N 0.05581(9) 0.20054(13) 0.64721(7) 0.0207(2) Uani 1 1 d . . . . .
C7 C 0.56066(11) 0.34343(18) 0.57121(9) 0.0305(3) Uani 1 1 d . . . . .
H7A H 0.592433 0.239945 0.585295 0.046 Uiso 1 1 calc R U . . .
H7B H 0.569621 0.409905 0.619117 0.046 Uiso 1 1 calc R U . . .
H7C H 0.599492 0.391039 0.530249 0.046 Uiso 1 1 calc R U . . .
C6 C 0.49291(11) 0.15669(16) 0.43722(8) 0.0221(3) Uani 1 1 d . . . . .
H6 H 0.569882 0.167826 0.457918 0.027 Uiso 1 1 calc R U . . .
C5 C 0.41443(11) 0.23519(15) 0.47402(8) 0.0207(3) Uani 1 1 d . . . . .
C4 C 0.29945(11) 0.22424(15) 0.44418(8) 0.0210(3) Uani 1 1 d . . . . .
C8 C 0.20533(11) 0.29916(16) 0.47750(8) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.13872(11) 0.44057(16) 0.58790(8) 0.0238(3) Uani 1 1 d . . . . .
H9A H 0.071698 0.451817 0.546767 0.029 Uiso 1 1 calc R U . . .
H9B H 0.166156 0.546960 0.603332 0.029 Uiso 1 1 calc R U . . .
C10 C 0.10501(12) 0.36084(16) 0.66105(8) 0.0248(3) Uani 1 1 d . . . . .
H10A H 0.171705 0.353420 0.702734 0.030 Uiso 1 1 calc R U . . .
H10B H 0.049978 0.428130 0.682629 0.030 Uiso 1 1 calc R U . . .
C11 C 0.02077(12) 0.13734(17) 0.72308(8) 0.0264(3) Uani 1 1 d . . . . .
H11A H -0.020787 0.038517 0.710637 0.032 Uiso 1 1 calc R U . . .
H11B H -0.030463 0.212986 0.743114 0.032 Uiso 1 1 calc R U . . .
C12 C 0.11855(13) 0.10703(19) 0.78852(9) 0.0327(3) Uani 1 1 d . . . . .
H12A H 0.174374 0.043215 0.766970 0.049 Uiso 1 1 calc R U . . .
H12B H 0.092410 0.051438 0.833054 0.049 Uiso 1 1 calc R U . . .
H12C H 0.152117 0.206828 0.807867 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.30247(3) -0.06043(5) 0.25461(2) 0.03225(10) Uani 1 1 d . . . . .
C14 C -0.14028(12) 0.2835(2) 0.58751(9) 0.0329(3) Uani 1 1 d . . . . .
H14A H -0.170783 0.247277 0.634976 0.049 Uiso 1 1 calc R U . . .
H14B H -0.196799 0.271360 0.539819 0.049 Uiso 1 1 calc R U . . .
H14C H -0.119296 0.393870 0.594196 0.049 Uiso 1 1 calc R U . . .
C13 C -0.03814(11) 0.18738(17) 0.57750(8) 0.0245(3) Uani 1 1 d . . . . .
H13A H -0.060334 0.076218 0.570630 0.029 Uiso 1 1 calc R U . . .
H13B H -0.010302 0.221284 0.527917 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3749(16) . ?
O1 C7 1.4338(16) . ?
C1 N1 1.3525(18) . ?
C1 C2 1.4058(19) . ?
C1 C6 1.4076(19) . ?
N1 H1A 0.865(19) . ?
N1 H1B 0.841(19) . ?
C2 C3 1.3718(19) . ?
C2 Cl1 1.7475(14) . ?
N2 C8 1.3459(17) . ?
N2 C9 1.4574(17) . ?
N2 H2 0.848(17) . ?
O2 C8 1.2386(16) . ?
O3 H3C 0.86(2) . ?
O3 H3B 0.79(2) . ?
C3 C4 1.3963(19) . ?
C3 H3A 0.9500 . ?
N3 C10 1.4992(17) . ?
N3 C11 1.5062(18) . ?
N3 C13 1.5124(17) . ?
N3 H3 0.924(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 C5 1.3839(19) . ?
C6 H6 0.9500 . ?
C5 C4 1.4113(18) . ?
C4 C8 1.4890(18) . ?
C9 C10 1.5171(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C13 1.515(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C7 118.17(11) . . ?
N1 C1 C2 122.51(13) . . ?
N1 C1 C6 120.50(13) . . ?
C2 C1 C6 116.99(12) . . ?
C1 N1 H1A 120.0(12) . . ?
C1 N1 H1B 124.2(12) . . ?
H1A N1 H1B 115.8(17) . . ?
C3 C2 C1 121.32(12) . . ?
C3 C2 Cl1 119.57(10) . . ?
C1 C2 Cl1 119.10(10) . . ?
C8 N2 C9 122.14(12) . . ?
C8 N2 H2 119.3(11) . . ?
C9 N2 H2 118.4(11) . . ?
H3C O3 H3B 104(2) . . ?
C2 C3 C4 122.16(12) . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
C10 N3 C11 110.61(10) . . ?
C10 N3 C13 115.10(11) . . ?
C11 N3 C13 110.95(10) . . ?
C10 N3 H3 109.7(10) . . ?
C11 N3 H3 106.7(10) . . ?
C13 N3 H3 103.2(10) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 C1 121.44(12) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C5 C6 122.00(12) . . ?
O1 C5 C4 116.96(12) . . ?
C6 C5 C4 121.04(12) . . ?
C3 C4 C5 116.99(12) . . ?
C3 C4 C8 115.60(12) . . ?
C5 C4 C8 127.41(12) . . ?
O2 C8 N2 120.64(12) . . ?
O2 C8 C4 120.71(12) . . ?
N2 C8 C4 118.65(12) . . ?
N2 C9 C10 114.32(11) . . ?
N2 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
N2 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N3 C10 C9 115.70(11) . . ?
N3 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
N3 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
N3 C11 C12 112.97(12) . . ?
N3 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C13 C14 113.90(11) . . ?
N3 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N3 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178.16(13) . . . . ?
C6 C1 C2 C3 -1.93(19) . . . . ?
N1 C1 C2 Cl1 -1.33(18) . . . . ?
C6 C1 C2 Cl1 178.57(10) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
Cl1 C2 C3 C4 179.51(10) . . . . ?
N1 C1 C6 C5 -177.54(13) . . . . ?
C2 C1 C6 C5 2.55(19) . . . . ?
C7 O1 C5 C6 0.56(19) . . . . ?
C7 O1 C5 C4 -178.91(12) . . . . ?
C1 C6 C5 O1 179.27(12) . . . . ?
C1 C6 C5 C4 -1.3(2) . . . . ?
C2 C3 C4 C5 1.31(19) . . . . ?
C2 C3 C4 C8 -178.43(12) . . . . ?
O1 C5 C4 C3 178.80(11) . . . . ?
C6 C5 C4 C3 -0.68(19) . . . . ?
O1 C5 C4 C8 -1.5(2) . . . . ?
C6 C5 C4 C8 179.02(13) . . . . ?
C9 N2 C8 O2 -4.4(2) . . . . ?
C9 N2 C8 C4 176.71(12) . . . . ?
C3 C4 C8 O2 -14.15(19) . . . . ?
C5 C4 C8 O2 166.14(13) . . . . ?
C3 C4 C8 N2 164.78(12) . . . . ?
C5 C4 C8 N2 -14.9(2) . . . . ?
C8 N2 C9 C10 116.45(14) . . . . ?
C11 N3 C10 C9 -177.25(11) . . . . ?
C13 N3 C10 C9 -50.51(16) . . . . ?
N2 C9 C10 N3 -61.38(16) . . . . ?
C10 N3 C11 C12 -66.52(15) . . . . ?
C13 N3 C11 C12 164.47(12) . . . . ?
C10 N3 C13 C14 -63.22(16) . . . . ?
C11 N3 C13 C14 63.34(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1B Cl1 0.841(19) 2.684(18) 3.0078(15) 104.5(14) . yes
N1 H1B O3 0.841(19) 2.146(19) 2.9606(18) 163.2(17) 2_545 yes
N1 H1A Cl2 0.865(19) 2.394(19) 3.2460(15) 168.6(16) 3_656 yes
N2 H2 O1 0.848(17) 2.075(16) 2.7103(15) 131.3(14) . yes
N3 H3 Cl2 0.924(17) 2.176(18) 3.0785(12) 165.1(14) . yes
O3 H3B O2 0.79(2) 1.99(2) 2.7622(16) 170(2) . yes
O3 H3C Cl2 0.86(2) 2.35(2) 3.1989(14) 169(2) 3_556 yes
C3 H3A O2 0.95 2.40 2.7465(17) 100.8 . yes
C9 H9A O2 0.99 2.33 2.7588(17) 104.9 . yes
C13 H13B O2 0.99 2.38 3.3307(18) 161.7 . yes

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.043


_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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1585431'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-02-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: Due to the small size of the crystal, high angle reflection was very weak and lead to high Rint.
;
_vrf_PLAT020_shelx               
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.133 Report
RESPONSE: Due to the small size of the crystal, high angle reflection was very weak and lead to high Rint.
;
_vrf_PLAT026_shelx               
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        49% Check
RESPONSE: This alert is due to the small size of the crystal.
;
_vrf_PLAT911_shelx               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         20 Report
RESPONSE: Related with the reflection behind beam stop and weak diffraction due to the small sized crystal
;
# Added during the CSD deposition process: Tuesday 14 November 2017 06:23 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'4-Amino-5-chloro-N-((2-diethylamino)-ethyl)-2-methoxybenzamide hydrochloride monohydrate'
_chemical_name_common            'Metoclopramide HCl anhydrate'
_chemical_melting_point          460
_chemical_formula_moiety         'C14 H23 Cl N3 O2, Cl'
_chemical_formula_sum            'C14 H23 Cl2 N3 O2'
_chemical_formula_weight         336.25

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   14.6866(4)
_cell_length_b                   7.0245(2)
_cell_length_c                   33.0316(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3407.74(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    36288
_cell_measurement_theta_min      4.028
_cell_measurement_theta_max      68.165

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.493
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   'abscor, T. Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID2'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            36288
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_av_R_equivalents  0.1327
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         4.028
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3100
_reflns_number_gt                1526
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'RAPID-AUTO (Rigaku, 2009)'
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2009)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2009)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1287P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2502
_refine_ls_wR_factor_gt          0.1996
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30062(9) 0.6489(2) 0.59075(4) 0.0615(5) Uani 1 1 d . . . . .
C1 C 0.1517(4) 0.7010(7) 0.54242(17) 0.0493(13) Uani 1 1 d . . . . .
O1 O 0.1273(2) 0.8512(5) 0.43621(11) 0.0514(10) Uani 1 1 d . . . . .
N1 N 0.1001(3) 0.6491(6) 0.57457(14) 0.0591(13) Uani 1 1 d . . . . .
H1A H 0.040433 0.645669 0.572382 0.071 Uiso 1 1 calc R U . . .
H1B H 0.126313 0.618707 0.597648 0.071 Uiso 1 1 calc R U . . .
Cl2 Cl 0.41032(10) 1.3641(2) 0.31051(5) 0.0651(5) Uani 1 1 d . . . . .
C2 C 0.2476(3) 0.7050(8) 0.54501(16) 0.0476(14) Uani 1 1 d . . . . .
O2 O 0.4088(2) 0.8335(5) 0.44591(11) 0.0625(12) Uani 1 1 d . . . . .
N2 N 0.2900(3) 0.9183(7) 0.40672(13) 0.0535(12) Uani 1 1 d . . . . .
H2 H 0.230424 0.917148 0.403708 0.064 Uiso 1 1 calc R U . . .
N3 N 0.4195(3) 0.9194(6) 0.30883(12) 0.0520(12) Uani 1 1 d . . . . .
H3 H 0.420725 1.061745 0.308379 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2997(3) 0.7509(7) 0.51197(16) 0.0480(14) Uani 1 1 d . . . . .
H3A H 0.364118 0.748526 0.514537 0.058 Uiso 1 1 calc R U . . .
C7 C 0.0291(3) 0.8584(8) 0.43210(18) 0.0590(16) Uani 1 1 d . . . . .
H7A H 0.013175 0.890444 0.404108 0.088 Uiso 1 1 calc R U . . .
H7B H 0.004506 0.955590 0.450373 0.088 Uiso 1 1 calc R U . . .
H7C H 0.003158 0.734083 0.439061 0.088 Uiso 1 1 calc R U . . .
C6 C 0.1136(4) 0.7498(7) 0.50565(15) 0.0466(13) Uani 1 1 d . . . . .
H6 H 0.049129 0.748015 0.503098 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1647(4) 0.8005(7) 0.47271(16) 0.0475(13) Uani 1 1 d . . . . .
C4 C 0.2617(3) 0.8011(7) 0.47466(17) 0.0452(13) Uani 1 1 d . . . . .
C8 C 0.3259(4) 0.8510(7) 0.44144(17) 0.0478(13) Uani 1 1 d . . . . .
C9 C 0.3462(4) 0.9928(8) 0.37402(15) 0.0567(15) Uani 1 1 d . . . . .
H9A H 0.409008 1.012478 0.384021 0.068 Uiso 1 1 calc R U . . .
H9B H 0.321932 1.117664 0.365268 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3480(4) 0.8596(7) 0.33853(17) 0.0586(16) Uani 1 1 d . . . . .
H10A H 0.360938 0.728738 0.348040 0.070 Uiso 1 1 calc R U . . .
H10B H 0.287748 0.859292 0.325130 0.070 Uiso 1 1 calc R U . . .
C11 C 0.5123(4) 0.8512(9) 0.3232(2) 0.0735(19) Uani 1 1 d . . . . .
H11A H 0.512422 0.849522 0.353138 0.088 Uiso 1 1 calc R U . . .
H11B H 0.521122 0.718557 0.313819 0.088 Uiso 1 1 calc R U . . .
C12 C 0.5895(4) 0.9652(10) 0.30937(18) 0.084(2) Uani 1 1 d . . . . .
H12A H 0.645989 0.912945 0.320616 0.126 Uiso 1 1 calc R U . . .
H12B H 0.581930 1.096975 0.318511 0.126 Uiso 1 1 calc R U . . .
H12C H 0.592435 0.962135 0.279740 0.126 Uiso 1 1 calc R U . . .
C13 C 0.4020(5) 0.8538(9) 0.26733(18) 0.0691(19) Uani 1 1 d . . . . .
H13A H 0.386353 0.716736 0.268082 0.083 Uiso 1 1 calc R U . . .
H13B H 0.458539 0.867630 0.251279 0.083 Uiso 1 1 calc R U . . .
C14 C 0.3268(4) 0.9596(11) 0.24642(18) 0.079(2) Uani 1 1 d . . . . .
H14A H 0.323806 0.920008 0.217999 0.119 Uiso 1 1 calc R U . . .
H14B H 0.338667 1.096697 0.247861 0.119 Uiso 1 1 calc R U . . .
H14C H 0.268713 0.931181 0.259731 0.119 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.745(5) . ?
C1 N1 1.355(6) . ?
C1 C6 1.381(7) . ?
C1 C2 1.411(7) . ?
O1 C5 1.372(6) . ?
O1 C7 1.450(5) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C2 C3 1.372(7) . ?
O2 C8 1.232(6) . ?
N2 C8 1.348(6) . ?
N2 C9 1.457(6) . ?
N2 H2 0.8800 . ?
N3 C13 1.469(6) . ?
N3 C10 1.496(6) . ?
N3 C11 1.521(7) . ?
N3 H3 1.0000 . ?
C3 C4 1.398(7) . ?
C3 H3A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 C5 1.369(7) . ?
C6 H6 0.9500 . ?
C5 C4 1.427(7) . ?
C4 C8 1.488(7) . ?
C9 C10 1.500(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.461(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.500(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 C1 C6 122.0(5) . . ?
N1 C1 C2 121.1(5) . . ?
C6 C1 C2 117.0(5) . . ?
C5 O1 C7 119.3(4) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 Cl1 119.6(4) . . ?
C1 C2 Cl1 119.6(4) . . ?
C8 N2 C9 122.3(5) . . ?
C8 N2 H2 118.8 . . ?
C9 N2 H2 118.8 . . ?
C13 N3 C10 113.7(5) . . ?
C13 N3 C11 110.4(5) . . ?
C10 N3 C11 109.6(4) . . ?
C13 N3 H3 107.7 . . ?
C10 N3 H3 107.7 . . ?
C11 N3 H3 107.7 . . ?
C2 C3 C4 122.6(5) . . ?
C2 C3 H3A 118.7 . . ?
C4 C3 H3A 118.7 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 C1 122.8(5) . . ?
C5 C6 H6 118.6 . . ?
C1 C6 H6 118.6 . . ?
C6 C5 O1 123.1(5) . . ?
C6 C5 C4 120.8(5) . . ?
O1 C5 C4 116.0(5) . . ?
C3 C4 C5 116.0(5) . . ?
C3 C4 C8 117.2(5) . . ?
C5 C4 C8 126.9(5) . . ?
O2 C8 N2 121.6(5) . . ?
O2 C8 C4 120.9(5) . . ?
N2 C8 C4 117.5(5) . . ?
N2 C9 C10 111.5(4) . . ?
N2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N3 C10 C9 110.5(4) . . ?
N3 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 N3 115.2(5) . . ?
C12 C11 H11A 108.5 . . ?
N3 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
N3 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 113.8(5) . . ?
N3 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N3 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N1 C1 C2 C3 177.6(5) . . . . ?
C6 C1 C2 C3 -1.6(8) . . . . ?
N1 C1 C2 Cl1 -1.9(7) . . . . ?
C6 C1 C2 Cl1 179.0(4) . . . . ?
C1 C2 C3 C4 1.9(8) . . . . ?
Cl1 C2 C3 C4 -178.7(4) . . . . ?
N1 C1 C6 C5 -179.2(5) . . . . ?
C2 C1 C6 C5 -0.1(8) . . . . ?
C1 C6 C5 O1 -179.3(5) . . . . ?
C1 C6 C5 C4 1.5(8) . . . . ?
C7 O1 C5 C6 2.2(7) . . . . ?
C7 O1 C5 C4 -178.5(4) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C2 C3 C4 C8 179.0(5) . . . . ?
C6 C5 C4 C3 -1.2(7) . . . . ?
O1 C5 C4 C3 179.5(4) . . . . ?
C6 C5 C4 C8 179.4(5) . . . . ?
O1 C5 C4 C8 0.1(7) . . . . ?
C9 N2 C8 O2 -6.5(8) . . . . ?
C9 N2 C8 C4 172.6(5) . . . . ?
C3 C4 C8 O2 5.7(8) . . . . ?
C5 C4 C8 O2 -174.9(5) . . . . ?
C3 C4 C8 N2 -173.3(5) . . . . ?
C5 C4 C8 N2 6.0(8) . . . . ?
C8 N2 C9 C10 108.0(6) . . . . ?
C13 N3 C10 C9 -155.6(5) . . . . ?
C11 N3 C10 C9 80.3(6) . . . . ?
N2 C9 C10 N3 -169.1(4) . . . . ?
C13 N3 C11 C12 81.1(6) . . . . ?
C10 N3 C11 C12 -153.0(5) . . . . ?
C10 N3 C13 C14 73.6(7) . . . . ?
C11 N3 C13 C14 -162.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1B Cl1 0.88 2.58 2.993(4) 109.7 . yes
N1 H1A O2 0.88 2.03 2.893(5) 166.1 3_466 yes
N2 H2 O1 0.88 1.91 2.622(5) 136.5 . yes
C3 H3A O2 0.95 2.43 2.768(6) 100.4 . yes
C9 H9A O2 0.99 2.40 2.782(6) 102.1 . yes
N3 H3 Cl2 1.00 2.13 3.127(5) 174.1 . yes
C9 H9B Cl2 0.99 2.82 3.478(5) 124.5 . yes
C13 H13B Cl2 0.99 2.81 3.770(7) 164.6 4_645 yes

_refine_diff_density_max         0.729
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.081


_exptl_crystal_recrystallization_method 'From the Melt'
