# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_4-Chloropiperidine_monohydrate_100K
_database_code_depnum_ccdc_archive 'CCDC 2026852'
loop_
_audit_author_name
_audit_author_address
'Pawel Socha'
; Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-Chloropiperidine_monohydrate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H12 Cl N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         137.61

_chemical_melting_point          270

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.2628(2)
_cell_length_b                   25.4439(14)
_cell_length_c                   5.2264(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.777(2)
_cell_angle_gamma                90
_cell_volume                     694.96(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      3.2027
_cell_measurement_theta_max      29.1173
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296

_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scan'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            7073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6

_refine_special_details          
;
;

_reflns_number_total             1176
_reflns_number_gt                1041
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0839
_refine_ls_goodness_of_fit_ref   1.320
_refine_ls_restrained_S_all      1.320
_refine_ls_number_reflns         1176
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0112P)²+0.6478P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ' '
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.76527(10) 0.45712(2) 0.94459(11) 0.01893(18) Uani d . . . 1 . .
N N1 0.2416(4) 0.32938(7) 0.5442(4) 0.0162(4) Uani d . . . 1 . .
H H1N1 0.362(6) 0.3178(10) 0.458(5) 0.024 Uiso d U . . 1 . .
C C2 0.1822(4) 0.38455(9) 0.4801(4) 0.0168(5) Uani d . . . 1 . .
H H2A 0.0307 0.3951 0.5635 0.02 Uiso calc U . R 1 . .
H H2B 0.1361 0.3875 0.2915 0.02 Uiso calc U . R 1 . .
C C3 0.4018(4) 0.42299(8) 0.5631(4) 0.0162(5) Uani d . . . 1 . .
H H3A 0.5467 0.4162 0.4629 0.019 Uiso calc U . R 1 . .
H H3B 0.3431 0.4596 0.5293 0.019 Uiso calc U . R 1 . .
C C4 0.4879(4) 0.41576(8) 0.8488(4) 0.0138(5) Uani d . . . 1 . .
H H4 0.3456 0.4268 0.9479 0.017 Uiso calc U . R 1 . .
C C5 0.5547(4) 0.35899(8) 0.9141(4) 0.0150(5) Uani d . . . 1 . .
H H5A 0.5983 0.3552 1.1027 0.018 Uiso calc U . R 1 . .
H H5B 0.7054 0.3483 0.8298 0.018 Uiso calc U . R 1 . .
C C6 0.3262(4) 0.32356(8) 0.8215(4) 0.0159(5) Uani d . . . 1 . .
H H6A 0.3743 0.2865 0.858 0.019 Uiso calc U . R 1 . .
H H6B 0.1819 0.3322 0.9197 0.019 Uiso calc U . R 1 . .
O O1 0.7789(3) 0.27468(6) 0.4306(3) 0.0170(4) Uani d . . . 1 . .
H H1O1 0.785(5) 0.2611(11) 0.290(6) 0.025 Uiso d U . . 1 . .
H H2O1 0.916(6) 0.2901(11) 0.460(5) 0.025 Uiso d U . . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0140(3) 0.0156(3) 0.0268(3) -0.0030(2) 0.0008(2) -0.0038(2)
N1 0.0140(10) 0.0173(10) 0.0177(10) -0.0001(7) 0.0035(8) -0.0036(8)
C2 0.0144(11) 0.0203(12) 0.0155(11) -0.0009(9) 0.0014(9) -0.0001(9)
C3 0.0152(11) 0.0148(11) 0.0184(12) -0.0007(8) 0.0014(9) 0.0014(9)
C4 0.0097(10) 0.0133(10) 0.0185(11) -0.0019(8) 0.0023(9) -0.0021(9)
C5 0.0121(11) 0.0161(11) 0.0166(11) 0.0014(8) 0.0009(8) 0.0006(9)
C6 0.0151(11) 0.0128(11) 0.0202(12) -0.0003(8) 0.0038(9) 0.0022(9)
O1 0.0152(8) 0.0185(9) 0.0177(8) -0.0040(6) 0.0033(7) -0.0028(7)

_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
Cl1 C4 . 1.821(2) ?
N1 C2 . 1.468(3) ?
N1 C6 . 1.472(3) ?
N1 H1N1 . 0.87(3) ?
C2 C3 . 1.537(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.519(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.516(3) ?
C4 H4 . 1.0 ?
C5 C6 . 1.535(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
O1 H1O1 . 0.82(3) ?
O1 H2O1 . 0.82(3) ?

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 N1 C6 . . 110.63(17) ?
C2 N1 H1N1 . . 110.6(18) ?
C6 N1 H1N1 . . 108.9(18) ?
N1 C2 C3 . . 114.29(18) ?
N1 C2 H2A . . 108.7 ?
C3 C2 H2A . . 108.7 ?
N1 C2 H2B . . 108.7 ?
C3 C2 H2B . . 108.7 ?
H2A C2 H2B . . 107.6 ?
C4 C3 C2 . . 109.12(18) ?
C4 C3 H3A . . 109.9 ?
C2 C3 H3A . . 109.9 ?
C4 C3 H3B . . 109.9 ?
C2 C3 H3B . . 109.9 ?
H3A C3 H3B . . 108.3 ?
C5 C4 C3 . . 111.77(18) ?
C5 C4 Cl1 . . 109.39(14) ?
C3 C4 Cl1 . . 109.67(15) ?
C5 C4 H4 . . 108.7 ?
C3 C4 H4 . . 108.7 ?
Cl1 C4 H4 . . 108.7 ?
C4 C5 C6 . . 109.68(17) ?
C4 C5 H5A . . 109.7 ?
C6 C5 H5A . . 109.7 ?
C4 C5 H5B . . 109.7 ?
C6 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
N1 C6 C5 . . 112.71(18) ?
N1 C6 H6A . . 109.0 ?
C5 C6 H6A . . 109.0 ?
N1 C6 H6B . . 109.0 ?
C5 C6 H6B . . 109.0 ?
H6A C6 H6B . . 107.8 ?
H1O1 O1 H2O1 . . 104.(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . 55.0(2) ?
N1 C2 C3 C4 . . . . -54.1(2) ?
C2 C3 C4 C5 . . . . 53.8(2) ?
C2 C3 C4 Cl1 . . . . 175.33(14) ?
C3 C4 C5 C6 . . . . -55.5(2) ?
Cl1 C4 C5 C6 . . . . -177.14(15) ?
C2 N1 C6 C5 . . . . -55.6(2) ?
C4 C5 C6 N1 . . . . 56.2(2) ?

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 H1N1 O1 . 0.87(3) 2.47(3) 3.269(3) 152.(2) ?
O1 H1O1 O1 4_565 0.82(3) 2.08(3) 2.8994(14) 177.(3) ?
O1 H2O1 N1 1_655 0.82(3) 1.99(3) 2.806(3) 177.(3) ?
####################################################################### 
# 
# 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_4-Chloropiperidine_monohydrate_190K
_database_code_depnum_ccdc_archive 'CCDC 2026853'
loop_
_audit_author_name
_audit_author_address
'Pawel Socha'
; Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-Chloropiperidine_monohydrate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H12 Cl N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         137.61

_chemical_melting_point          270

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.2978(2)
_cell_length_b                   25.4806(15)
_cell_length_c                   5.2759(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.132(2)
_cell_angle_gamma                90
_cell_volume                     706.69(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      3.1981
_cell_measurement_theta_max      26.3236
_cell_measurement_temperature    190.(2)

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296

_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_T_max  0.7454

_exptl_special_details           
;
;

_diffrn_ambient_temperature      190.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            7214
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6

_refine_special_details          
;
;

_reflns_number_total             1203
_reflns_number_gt                1045
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0837
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_restrained_S_all      1.210
_refine_ls_number_reflns         1203
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0154P)²+0.5576P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.76543(11) 0.45675(2) 0.94266(12) 0.0343(2) Uani d . . . 1 . .
N N1 0.2440(4) 0.32960(7) 0.5453(4) 0.0281(4) Uani d . . . 1 . .
H H1N1 0.366(6) 0.3173(10) 0.461(5) 0.042 Uiso d U . . 1 . .
C C2 0.1859(4) 0.38458(9) 0.4808(4) 0.0291(5) Uani d . . . 1 . .
H H2A 0.0356 0.3953 0.5625 0.035 Uiso calc U . R 1 . .
H H2B 0.14 0.3875 0.2936 0.035 Uiso calc U . R 1 . .
C C3 0.4044(4) 0.42262(8) 0.5636(4) 0.0279(5) Uani d . . . 1 . .
H H3A 0.5483 0.4155 0.4654 0.034 Uiso calc U . R 1 . .
H H3B 0.3471 0.4592 0.5289 0.034 Uiso calc U . R 1 . .
C C4 0.4897(4) 0.41566(8) 0.8465(4) 0.0227(5) Uani d . . . 1 . .
H H4 0.3483 0.4269 0.9435 0.027 Uiso calc U . R 1 . .
C C5 0.5550(4) 0.35908(8) 0.9120(4) 0.0254(5) Uani d . . . 1 . .
H H5A 0.5985 0.3554 1.0991 0.03 Uiso calc U . R 1 . .
H H5B 0.7047 0.3483 0.8294 0.03 Uiso calc U . R 1 . .
C C6 0.3279(4) 0.32383(8) 0.8196(4) 0.0275(5) Uani d . . . 1 . .
H H6A 0.3753 0.2868 0.8563 0.033 Uiso calc U . R 1 . .
H H6B 0.1846 0.3326 0.916 0.033 Uiso calc U . R 1 . .
O O1 0.7826(3) 0.27448(6) 0.4308(3) 0.0292(4) Uani d . . . 1 . .
H H1O1 0.789(5) 0.2604(11) 0.290(6) 0.044 Uiso d U . . 1 . .
H H2O1 0.921(6) 0.2899(11) 0.458(5) 0.044 Uiso d U . . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0264(3) 0.0273(3) 0.0482(4) -0.0058(2) 0.0006(2) -0.0075(3)
N1 0.0258(10) 0.0290(10) 0.0299(10) -0.0024(8) 0.0053(8) -0.0069(8)
C2 0.0252(12) 0.0364(13) 0.0249(11) -0.0010(9) -0.0006(9) 0.0020(10)
C3 0.0282(12) 0.0252(12) 0.0300(12) -0.0016(9) 0.0020(9) 0.0049(9)
C4 0.0179(10) 0.0214(10) 0.0288(12) -0.0024(8) 0.0030(8) -0.0029(9)
C5 0.0222(11) 0.0260(11) 0.0274(11) 0.0012(9) 0.0010(9) 0.0019(9)
C6 0.0274(12) 0.0218(11) 0.0337(12) -0.0015(9) 0.0052(9) 0.0033(9)
O1 0.0272(9) 0.0321(9) 0.0286(8) -0.0065(7) 0.0052(7) -0.0036(7)

_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
Cl1 C4 . 1.817(2) ?
N1 C2 . 1.465(3) ?
N1 C6 . 1.468(3) ?
C2 C3 . 1.531(3) ?
C3 C4 . 1.516(3) ?
C4 C5 . 1.513(3) ?
C5 C6 . 1.532(3) ?

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 N1 C6 . . 110.72(17) ?
N1 C2 C3 . . 114.16(18) ?
C4 C3 C2 . . 109.22(18) ?
C5 C4 C3 . . 111.61(17) ?
C5 C4 Cl1 . . 109.40(14) ?
C3 C4 Cl1 . . 109.79(15) ?
C4 C5 C6 . . 109.74(17) ?
N1 C6 C5 . . 112.64(18) ?

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
C6 N1 C2 C3 . . . . 55.1(2) ?
N1 C2 C3 C4 . . . . -54.2(3) ?
C2 C3 C4 C5 . . . . 54.0(2) ?
C2 C3 C4 Cl1 . . . . 175.49(15) ?
C3 C4 C5 C6 . . . . -55.5(2) ?
Cl1 C4 C5 C6 . . . . -177.21(15) ?
C2 N1 C6 C5 . . . . -55.5(2) ?
C4 C5 C6 N1 . . . . 56.2(2) ?

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 H1N1 O1 . 0.88(3) 2.49(3) 3.302(3) 154.(2) ?
O1 H1O1 O1 4_565 0.83(3) 2.09(3) 2.9181(14) 177.(3) ?
O1 H2O1 N1 1_655 0.83(3) 1.99(3) 2.819(3) 176.(3) ?
####################################################################### 
# 
# 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_4-Methylpiperidine_hemihydrate_100K
_database_code_depnum_ccdc_archive 'CCDC 2026856'
loop_
_audit_author_name
_audit_author_address
'Pawel Socha'
; Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-Methylpiperidine_hemihydrate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H28 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         216.36

_chemical_melting_point          253

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.3056(4)
_cell_length_b                   23.544(2)
_cell_length_c                   11.1942(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.188(2)
_cell_angle_gamma                90
_cell_volume                     1380.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9073
_cell_measurement_theta_min      3.1839
_cell_measurement_theta_max      26.4628
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       cylidricall
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.041
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488

_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'TWINABS-2012/1 (Bruker AXS Inc., 2012)'
_exptl_absorpt_correction_T_min  0.496420
_exptl_absorpt_correction_T_max  0.745372

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            2364
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;

Refined as a 5-component twin.
;

_reflns_number_total             2364
_reflns_number_gt                2007
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1240
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_number_reflns         2364
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+1.1659P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.030(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'
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       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ' '
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4231(3) 0.58749(6) 0.49400(13) 0.0254(3) Uani d . . . 1 . .
H H1 0.544(5) 0.6020(10) 0.470(2) 0.038 Uiso d U . . 1 . .
H H2 0.497(4) 0.5654(10) 0.561(2) 0.038 Uiso d U . . 1 . .
N N1 0.7009(3) 0.51301(7) 0.68264(14) 0.0240(4) Uani d . . . 1 . .
H H1N1 0.658(4) 0.4823(10) 0.642(2) 0.036 Uiso d U . . 1 . .
C C2 0.6946(4) 0.50242(8) 0.81134(16) 0.0247(4) Uani d . . . 1 . .
H H2A 0.8181 0.4721 0.841 0.03 Uiso calc U . R 1 . .
H H2B 0.5221 0.4893 0.8216 0.03 Uiso calc U . R 1 . .
C C3 0.7610(3) 0.55619(8) 0.88551(16) 0.0243(4) Uani d . . . 1 . .
H H3A 0.7617 0.5478 0.9722 0.029 Uiso calc U . R 1 . .
H H3B 0.6291 0.5854 0.8604 0.029 Uiso calc U . R 1 . .
C C4 1.0230(3) 0.57930(7) 0.86849(16) 0.0208(4) Uani d . . . 1 . .
H H4 1.1542 0.5503 0.9005 0.025 Uiso calc U . R 1 . .
C C5 1.0299(3) 0.58659(8) 0.73298(16) 0.0221(4) Uani d . . . 1 . .
H H5A 0.9105 0.6172 0.7005 0.027 Uiso calc U . R 1 . .
H H5B 1.2038 0.598 0.7214 0.027 Uiso calc U . R 1 . .
C C6 0.9563(3) 0.53192(8) 0.66315(16) 0.0228(4) Uani d . . . 1 . .
H H6A 0.9558 0.5384 0.5757 0.027 Uiso calc U . R 1 . .
H H6B 1.0834 0.502 0.6906 0.027 Uiso calc U . R 1 . .
C C7 1.0893(4) 0.63454(8) 0.93851(18) 0.0300(5) Uani d . . . 1 . .
H H7A 1.2596 0.6473 0.9269 0.045 Uiso calc U . R 1 . .
H H7B 1.0874 0.628 1.0248 0.045 Uiso calc U . R 1 . .
H H7C 0.9634 0.6638 0.9086 0.045 Uiso calc U . R 1 . .
N N2 0.8720(3) 0.63820(7) 0.41626(14) 0.0256(4) Uani d . . . 1 . .
H H1N2 1.012(5) 0.6223(10) 0.457(2) 0.038 Uiso d U . . 1 . .
C C8 0.8681(4) 0.69749(8) 0.45717(17) 0.0265(4) Uani d . . . 1 . .
H H8A 1.0246 0.7172 0.4419 0.032 Uiso calc U . R 1 . .
H H8B 0.8642 0.6985 0.5453 0.032 Uiso calc U . R 1 . .
C C9 0.6338(3) 0.72750(8) 0.38966(16) 0.0227(4) Uani d . . . 1 . .
H H9A 0.6322 0.7674 0.4175 0.027 Uiso calc U . R 1 . .
H H9B 0.4778 0.7087 0.4082 0.027 Uiso calc U . R 1 . .
C C10 0.6323(3) 0.72642(8) 0.25317(16) 0.0227(4) Uani d . . . 1 . .
H H10 0.7878 0.747 0.2363 0.027 Uiso calc U . R 1 . .
C C11 0.6514(4) 0.66488(8) 0.21298(16) 0.0263(4) Uani d . . . 1 . .
H H11A 0.6658 0.6639 0.1259 0.032 Uiso calc U . R 1 . .
H H11B 0.4941 0.6443 0.2239 0.032 Uiso calc U . R 1 . .
C C12 0.8824(4) 0.63533(8) 0.28559(17) 0.0256(4) Uani d . . . 1 . .
H H12A 0.8859 0.5951 0.2602 0.031 Uiso calc U . R 1 . .
H H12B 1.0409 0.6538 0.269 0.031 Uiso calc U . R 1 . .
C C13 0.3979(4) 0.75665(10) 0.18426(19) 0.0362(5) Uani d . . . 1 . .
H H13A 0.3988 0.7534 0.097 0.054 Uiso calc U . R 1 . .
H H13B 0.4022 0.7968 0.2073 0.054 Uiso calc U . R 1 . .
H H13C 0.2426 0.739 0.2043 0.054 Uiso calc U . R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0156(7) 0.0297(7) 0.0302(7) -0.0009(5) 0.0019(5) 0.0054(6)
N1 0.0197(9) 0.0277(9) 0.0233(8) -0.0036(6) -0.0005(6) 0.0007(6)
C2 0.0183(10) 0.0291(10) 0.0269(10) -0.0024(7) 0.0042(7) 0.0043(8)
C3 0.0187(10) 0.0316(10) 0.0228(9) 0.0022(7) 0.0041(7) 0.0014(8)
C4 0.0164(9) 0.0237(9) 0.0219(9) 0.0024(7) 0.0020(7) 0.0000(7)
C5 0.0187(10) 0.0238(9) 0.0243(9) -0.0006(7) 0.0046(7) 0.0019(7)
C6 0.0202(10) 0.0252(10) 0.0236(9) 0.0008(7) 0.0051(7) 0.0002(7)
C7 0.0285(11) 0.0311(11) 0.0300(11) 0.0007(8) 0.0035(8) -0.0086(8)
N2 0.0162(9) 0.0300(9) 0.0300(9) 0.0031(6) 0.0022(6) 0.0104(7)
C8 0.0178(10) 0.0364(11) 0.0244(10) -0.0039(8) 0.0011(7) 0.0005(8)
C9 0.0185(10) 0.0235(9) 0.0274(10) -0.0009(7) 0.0073(7) -0.0023(7)
C10 0.0115(9) 0.0299(10) 0.0286(10) 0.0032(7) 0.0086(7) 0.0091(8)
C11 0.0202(10) 0.0384(11) 0.0209(9) 0.0026(8) 0.0052(7) -0.0021(8)
C12 0.0185(10) 0.0255(10) 0.0343(11) 0.0041(7) 0.0088(8) 0.0000(8)
C13 0.0230(11) 0.0494(13) 0.0380(12) 0.0127(9) 0.0104(9) 0.0192(10)

_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
O1 H1 . 0.81(3) ?
O1 H2 . 0.94(2) ?
N1 C2 . 1.468(2) ?
N1 C6 . 1.475(2) ?
N1 H1N1 . 0.86(2) ?
C2 C3 . 1.524(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.532(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C7 . 1.530(2) ?
C4 C5 . 1.533(2) ?
C4 H4 . 1.0 ?
C5 C6 . 1.524(2) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
N2 C8 . 1.470(2) ?
N2 C12 . 1.474(2) ?
N2 H1N2 . 0.89(2) ?
C8 C9 . 1.522(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.527(2) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C11 . 1.525(3) ?
C10 C13 . 1.530(3) ?
C10 H10 . 1.0 ?
C11 C12 . 1.526(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?

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
H1 O1 H2 . . 105.(2) ?
C2 N1 C6 . . 111.22(14) ?
C2 N1 H1N1 . . 108.9(15) ?
C6 N1 H1N1 . . 110.3(16) ?
N1 C2 C3 . . 110.73(15) ?
N1 C2 H2A . . 109.5 ?
C3 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 108.1 ?
C2 C3 C4 . . 111.26(15) ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3B . . 109.4 ?
C4 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C7 C4 C3 . . 112.15(15) ?
C7 C4 C5 . . 111.83(15) ?
C3 C4 C5 . . 109.16(14) ?
C7 C4 H4 . . 107.8 ?
C3 C4 H4 . . 107.8 ?
C5 C4 H4 . . 107.8 ?
C6 C5 C4 . . 111.62(14) ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5B . . 109.3 ?
C4 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
N1 C6 C5 . . 110.20(15) ?
N1 C6 H6A . . 109.6 ?
C5 C6 H6A . . 109.6 ?
N1 C6 H6B . . 109.6 ?
C5 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C8 N2 C12 . . 110.92(14) ?
C8 N2 H1N2 . . 106.9(15) ?
C12 N2 H1N2 . . 109.2(15) ?
N2 C8 C9 . . 109.70(15) ?
N2 C8 H8A . . 109.7 ?
C9 C8 H8A . . 109.7 ?
N2 C8 H8B . . 109.7 ?
C9 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
C8 C9 C10 . . 111.26(14) ?
C8 C9 H9A . . 109.4 ?
C10 C9 H9A . . 109.4 ?
C8 C9 H9B . . 109.4 ?
C10 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
C11 C10 C9 . . 108.73(14) ?
C11 C10 C13 . . 112.33(17) ?
C9 C10 C13 . . 111.76(15) ?
C11 C10 H10 . . 108.0 ?
C9 C10 H10 . . 108.0 ?
C13 C10 H10 . . 108.0 ?
C10 C11 C12 . . 111.19(15) ?
C10 C11 H11A . . 109.4 ?
C12 C11 H11A . . 109.4 ?
C10 C11 H11B . . 109.4 ?
C12 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
N2 C12 C11 . . 110.71(14) ?
N2 C12 H12A . . 109.5 ?
C11 C12 H12A . . 109.5 ?
N2 C12 H12B . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . 59.97(19) ?
N1 C2 C3 C4 . . . . -57.05(19) ?
C2 C3 C4 C7 . . . . 177.88(15) ?
C2 C3 C4 C5 . . . . 53.38(19) ?
C7 C4 C5 C6 . . . . -178.37(15) ?
C3 C4 C5 C6 . . . . -53.68(19) ?
C2 N1 C6 C5 . . . . -59.75(19) ?
C4 C5 C6 N1 . . . . 57.02(19) ?
C12 N2 C8 C9 . . . . 60.36(18) ?
N2 C8 C9 C10 . . . . -59.01(19) ?
C8 C9 C10 C11 . . . . 55.61(19) ?
C8 C9 C10 C13 . . . . -179.82(16) ?
C9 C10 C11 C12 . . . . -54.16(19) ?
C13 C10 C11 C12 . . . . -178.39(15) ?
C8 N2 C12 C11 . . . . -59.52(19) ?
C10 C11 C12 N2 . . . . 56.7(2) ?

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
O1 H1 N2 . 0.81(3) 2.11(3) 2.918(2) 176.(2) ?
O1 H2 N1 . 0.94(2) 2.02(3) 2.952(2) 169.(2) ?
N1 H1N1 O1 3_666 0.86(2) 2.24(2) 3.087(2) 168.(2) ?
N2 H1N2 O1 1_655 0.89(2) 2.30(2) 3.150(2) 159.(2) ?
####################################################################### 
# 
# 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_4-Chloropiperidine_trihydrate_100K
_database_code_depnum_ccdc_archive 'CCDC 2026854'
loop_
_audit_author_name
_audit_author_address
'Pawel Socha'
; Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-Chloropiperidine_trihydrate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H16 Cl N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         173.64

_chemical_melting_point          263

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4835(14)
_cell_length_b                   6.2084(5)
_cell_length_c                   12.2415(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.025(4)
_cell_angle_gamma                90
_cell_volume                     945.10(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2822
_cell_measurement_theta_min      3.2766
_cell_measurement_theta_max      26.1184
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'cylindricall '
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.5845
_exptl_absorpt_correction_T_max  0.7454

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9555
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             1654
_reflns_number_gt                1221
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1227
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.108
_refine_ls_number_reflns         1654
_refine_ls_number_parameters     112
_refine_ls_number_restraints     6
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+1.1858P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.92016(7) 0.83273(13) 0.56052(7) 0.0268(3) Uani d . . . 1 . .
N N1 0.7820(2) 0.2233(4) 0.7078(2) 0.0241(7) Uani d . . . 1 . .
H H1N1 0.838(3) 0.161(6) 0.707(3) 0.036 Uiso d U . . 1 . .
C C2 0.8009(3) 0.4125(5) 0.7794(3) 0.0271(8) Uani d . . . 1 . .
H H2A 0.8341 0.3643 0.8517 0.033 Uiso calc U . R 1 . .
H H2B 0.7309 0.4796 0.7911 0.033 Uiso calc U . R 1 . .
C C3 0.8737(3) 0.5818(5) 0.7329(3) 0.0242(8) Uani d . . . 1 . .
H H3A 0.878 0.7105 0.7809 0.029 Uiso calc U . R 1 . .
H H3B 0.9471 0.5229 0.7307 0.029 Uiso calc U . R 1 . .
C C4 0.8290(3) 0.6446(5) 0.6188(2) 0.0188(7) Uani d . . . 1 . .
H H4 0.7582 0.7174 0.6235 0.023 Uiso calc U . R 1 . .
C C5 0.8124(3) 0.4508(5) 0.5448(2) 0.0207(7) Uani d . . . 1 . .
H H5A 0.8826 0.3835 0.534 0.025 Uiso calc U . R 1 . .
H H5B 0.7785 0.4958 0.4722 0.025 Uiso calc U . R 1 . .
C C6 0.7401(3) 0.2883(5) 0.5969(3) 0.0245(8) Uani d . . . 1 . .
H H6A 0.6678 0.3523 0.6002 0.029 Uiso calc U . R 1 . .
H H6B 0.7322 0.1587 0.5497 0.029 Uiso calc U . R 1 . .
O O1 0.6251(2) -0.0194(4) 0.79270(19) 0.0257(6) Uani d . . D 1 . .
H H1O1 0.678(2) 0.045(6) 0.760(3) 0.038 Uiso d U . D 1 . .
H H2O1 0.583(3) -0.074(6) 0.739(2) 0.038 Uiso d U . D 1 . .
O O2 0.49036(19) -0.1891(4) 0.62625(19) 0.0272(6) Uani d . . D 1 . .
H H1O2 0.453(3) -0.294(5) 0.654(3) 0.041 Uiso d U . D 1 . .
H H2O2 0.528(3) -0.216(6) 0.571(2) 0.041 Uiso d U . D 1 . .
O O3 0.6153(2) -0.1746(4) 0.45517(19) 0.0318(6) Uani d . . D 1 . .
H H1O3 0.581(3) -0.066(5) 0.423(3) 0.048 Uiso d U . D 1 . .
H H2O3 0.616(3) -0.283(5) 0.408(3) 0.048 Uiso d U . D 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0314(5) 0.0213(4) 0.0286(5) -0.0025(4) 0.0081(3) 0.0046(3)
N1 0.0262(16) 0.0188(14) 0.0272(15) -0.0010(11) 0.0019(13) 0.0012(11)
C2 0.039(2) 0.0227(17) 0.0203(17) -0.0066(14) 0.0054(15) 0.0015(13)
C3 0.032(2) 0.0218(17) 0.0179(17) -0.0087(14) -0.0003(14) -0.0021(13)
C4 0.0224(17) 0.0154(15) 0.0193(16) -0.0021(12) 0.0044(13) 0.0000(13)
C5 0.0261(18) 0.0200(16) 0.0155(16) 0.0031(13) -0.0015(13) -0.0010(13)
C6 0.0277(19) 0.0204(17) 0.0246(18) -0.0014(13) -0.0018(14) -0.0048(13)
O1 0.0315(15) 0.0213(12) 0.0243(13) -0.0069(10) 0.0034(11) 0.0023(10)
O2 0.0341(15) 0.0246(13) 0.0235(13) -0.0019(10) 0.0055(10) -0.0002(10)
O3 0.0374(15) 0.0313(14) 0.0259(13) 0.0104(12) -0.0012(11) -0.0066(11)

_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
Cl1 C4 . 1.819(3) ?
N1 C6 . 1.468(4) ?
N1 C2 . 1.472(4) ?
N1 H1N1 . 0.80(4) ?
C2 C3 . 1.531(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.510(4) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.509(4) ?
C4 H4 . 1.0 ?
C5 C6 . 1.529(4) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
O1 H1O1 . 0.892(19) ?
O1 H2O1 . 0.877(19) ?
O2 H1O2 . 0.888(18) ?
O2 H2O2 . 0.872(18) ?
O3 H1O3 . 0.875(19) ?
O3 H2O3 . 0.886(19) ?

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
C6 N1 C2 . . 110.9(2) ?
C6 N1 H1N1 . . 112.(3) ?
C2 N1 H1N1 . . 107.(3) ?
N1 C2 C3 . . 113.3(3) ?
N1 C2 H2A . . 108.9 ?
C3 C2 H2A . . 108.9 ?
N1 C2 H2B . . 108.9 ?
C3 C2 H2B . . 108.9 ?
H2A C2 H2B . . 107.7 ?
C4 C3 C2 . . 109.8(3) ?
C4 C3 H3A . . 109.7 ?
C2 C3 H3A . . 109.7 ?
C4 C3 H3B . . 109.7 ?
C2 C3 H3B . . 109.7 ?
H3A C3 H3B . . 108.2 ?
C5 C4 C3 . . 111.7(2) ?
C5 C4 Cl1 . . 109.6(2) ?
C3 C4 Cl1 . . 109.6(2) ?
C5 C4 H4 . . 108.6 ?
C3 C4 H4 . . 108.6 ?
Cl1 C4 H4 . . 108.6 ?
C4 C5 C6 . . 109.3(3) ?
C4 C5 H5A . . 109.8 ?
C6 C5 H5A . . 109.8 ?
C4 C5 H5B . . 109.8 ?
C6 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.3 ?
N1 C6 C5 . . 113.0(3) ?
N1 C6 H6A . . 109.0 ?
C5 C6 H6A . . 109.0 ?
N1 C6 H6B . . 109.0 ?
C5 C6 H6B . . 109.0 ?
H6A C6 H6B . . 107.8 ?
H1O1 O1 H2O1 . . 105.(3) ?
H1O2 O2 H2O2 . . 119.(4) ?
H1O3 O3 H2O3 . . 109.(4) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . -54.5(4) ?
N1 C2 C3 C4 . . . . 54.1(4) ?
C2 C3 C4 C5 . . . . -54.7(4) ?
C2 C3 C4 Cl1 . . . . -176.4(2) ?
C3 C4 C5 C6 . . . . 55.6(3) ?
Cl1 C4 C5 C6 . . . . 177.3(2) ?
C2 N1 C6 C5 . . . . 55.5(4) ?
C4 C5 C6 N1 . . . . -56.1(3) ?

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 H1N1 Cl1 1_545 0.80(4) 2.96(4) 3.556(3) 133.(3) ?
O1 H1O1 N1 . 0.892(19) 1.87(2) 2.747(4) 169.(4) ?
O1 H2O1 O2 . 0.877(19) 1.860(19) 2.737(3) 179.(4) ?
O2 H1O2 O1 2_646 0.888(18) 1.854(19) 2.742(3) 178.(4) ?
O2 H2O2 O3 . 0.872(18) 1.88(2) 2.720(3) 161.(4) ?
O3 H1O3 O2 3_656 0.875(19) 1.89(2) 2.757(3) 172.(4) ?
O3 H2O3 O1 4 0.886(19) 1.88(2) 2.761(3) 171.(4) ?
####################################################################### 
# 
# 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_4-Chloropiperidine_trihydrate_210K
_database_code_depnum_ccdc_archive 'CCDC 2026855'
loop_
_audit_author_name
_audit_author_address
'Pawel Socha'
; Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-Chloropiperidine_trihydrate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H16 Cl N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         173.64

_chemical_melting_point          263

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5492(19)
_cell_length_b                   6.2375(7)
_cell_length_c                   12.3157(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.551(5)
_cell_angle_gamma                90
_cell_volume                     961.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1801
_cell_measurement_theta_min      3.2571
_cell_measurement_theta_max      23.3075
_cell_measurement_temperature    210.(2)

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.6084
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      210.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9733
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             1687
_reflns_number_gt                1013
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1281
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_refine_ls_number_reflns         1687
_refine_ls_number_parameters     112
_refine_ls_number_restraints     6
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.6338P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.91996(8) 0.82805(16) 0.56013(9) 0.0578(3) Uani d . . . 1 . .
N N1 0.7808(3) 0.2256(5) 0.7077(3) 0.0485(9) Uani d . . . 1 . .
H H1N1 0.836(3) 0.161(7) 0.704(4) 0.073 Uiso d U . . 1 . .
C C2 0.8009(3) 0.4122(6) 0.7777(3) 0.0557(11) Uani d . . . 1 . .
H H2A 0.8337 0.3643 0.8484 0.067 Uiso calc U . R 1 . .
H H2B 0.7325 0.4798 0.7901 0.067 Uiso calc U . R 1 . .
C C3 0.8734(3) 0.5786(6) 0.7308(3) 0.0505(10) Uani d . . . 1 . .
H H3A 0.8783 0.7053 0.778 0.061 Uiso calc U . R 1 . .
H H3B 0.9454 0.5192 0.7279 0.061 Uiso calc U . R 1 . .
C C4 0.8295(3) 0.6413(5) 0.6186(3) 0.0370(8) Uani d . . . 1 . .
H H4 0.76 0.714 0.6242 0.044 Uiso calc U . R 1 . .
C C5 0.8118(3) 0.4506(6) 0.5459(3) 0.0461(10) Uani d . . . 1 . .
H H5A 0.8804 0.383 0.5342 0.055 Uiso calc U . R 1 . .
H H5B 0.7782 0.4956 0.4749 0.055 Uiso calc U . R 1 . .
C C6 0.7397(3) 0.2910(6) 0.5987(3) 0.0516(10) Uani d . . . 1 . .
H H6A 0.6689 0.3557 0.6028 0.062 Uiso calc U . R 1 . .
H H6B 0.731 0.1635 0.5524 0.062 Uiso calc U . R 1 . .
O O1 0.6246(2) -0.0173(4) 0.7930(2) 0.0501(7) Uani d . . D 1 . .
H H1O1 0.679(2) 0.050(6) 0.764(3) 0.075 Uiso d U . D 1 . .
H H2O1 0.583(3) -0.078(7) 0.740(3) 0.075 Uiso d U . D 1 . .
O O2 0.4924(2) -0.1889(4) 0.6269(2) 0.0542(7) Uani d . . D 1 . .
H H1O2 0.452(3) -0.294(5) 0.649(3) 0.081 Uiso d U . D 1 . .
H H2O2 0.528(3) -0.223(7) 0.571(3) 0.081 Uiso d U . D 1 . .
O O3 0.6135(2) -0.1748(5) 0.4535(2) 0.0596(8) Uani d . . D 1 . .
H H1O3 0.577(3) -0.071(6) 0.422(3) 0.089 Uiso d U . D 1 . .
H H2O3 0.614(4) -0.278(5) 0.404(3) 0.089 Uiso d U . D 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0643(7) 0.0452(5) 0.0663(7) -0.0050(5) 0.0197(5) 0.0116(5)
N1 0.055(2) 0.0392(18) 0.052(2) -0.0034(15) 0.0050(18) 0.0039(15)
C2 0.074(3) 0.055(2) 0.038(2) -0.017(2) 0.005(2) 0.0022(19)
C3 0.067(3) 0.046(2) 0.037(2) -0.0165(19) -0.004(2) -0.0008(17)
C4 0.037(2) 0.0303(18) 0.044(2) 0.0009(15) 0.0075(16) 0.0025(16)
C5 0.058(3) 0.044(2) 0.036(2) 0.0029(18) 0.0018(19) -0.0039(17)
C6 0.056(3) 0.040(2) 0.058(3) -0.0043(17) -0.006(2) -0.0096(19)
O1 0.062(2) 0.0421(15) 0.0465(17) -0.0120(13) 0.0053(14) 0.0026(12)
O2 0.070(2) 0.0460(16) 0.0487(17) -0.0026(14) 0.0157(14) -0.0020(13)
O3 0.073(2) 0.0549(18) 0.0511(18) 0.0145(15) 0.0034(15) -0.0072(14)

_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
Cl1 C4 . 1.815(3) ?
N1 C6 . 1.457(5) ?
N1 C2 . 1.459(5) ?
N1 H1N1 . 0.81(4) ?
C2 C3 . 1.523(5) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C3 C4 . 1.499(5) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C4 C5 . 1.495(4) ?
C4 H4 . 0.99 ?
C5 C6 . 1.525(5) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
O1 H1O1 . 0.896(19) ?
O1 H2O1 . 0.883(19) ?
O2 H1O2 . 0.881(19) ?
O2 H2O2 . 0.876(19) ?
O3 H1O3 . 0.872(19) ?
O3 H2O3 . 0.884(19) ?

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
C6 N1 C2 . . 110.7(3) ?
C6 N1 H1N1 . . 109.(3) ?
C2 N1 H1N1 . . 109.(3) ?
N1 C2 C3 . . 113.6(3) ?
N1 C2 H2A . . 108.8 ?
C3 C2 H2A . . 108.8 ?
N1 C2 H2B . . 108.8 ?
C3 C2 H2B . . 108.8 ?
H2A C2 H2B . . 107.7 ?
C4 C3 C2 . . 109.9(3) ?
C4 C3 H3A . . 109.7 ?
C2 C3 H3A . . 109.7 ?
C4 C3 H3B . . 109.7 ?
C2 C3 H3B . . 109.7 ?
H3A C3 H3B . . 108.2 ?
C5 C4 C3 . . 111.8(3) ?
C5 C4 Cl1 . . 110.0(2) ?
C3 C4 Cl1 . . 109.7(2) ?
C5 C4 H4 . . 108.4 ?
C3 C4 H4 . . 108.4 ?
Cl1 C4 H4 . . 108.4 ?
C4 C5 C6 . . 109.2(3) ?
C4 C5 H5A . . 109.8 ?
C6 C5 H5A . . 109.8 ?
C4 C5 H5B . . 109.8 ?
C6 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.3 ?
N1 C6 C5 . . 113.4(3) ?
N1 C6 H6A . . 108.9 ?
C5 C6 H6A . . 108.9 ?
N1 C6 H6B . . 108.9 ?
C5 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.7 ?
H1O1 O1 H2O1 . . 109.(4) ?
H1O2 O2 H2O2 . . 114.(4) ?
H1O3 O3 H2O3 . . 105.(4) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . -54.1(5) ?
N1 C2 C3 C4 . . . . 54.0(5) ?
C2 C3 C4 C5 . . . . -54.6(4) ?
C2 C3 C4 Cl1 . . . . -176.8(3) ?
C3 C4 C5 C6 . . . . 55.3(4) ?
Cl1 C4 C5 C6 . . . . 177.5(3) ?
C2 N1 C6 C5 . . . . 55.2(4) ?
C4 C5 C6 N1 . . . . -56.0(4) ?

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 H1N1 Cl1 1_545 0.81(4) 2.97(4) 3.606(3) 137.(4) ?
O1 H1O1 N1 . 0.896(19) 1.86(2) 2.751(4) 172.(4) ?
O1 H2O1 O2 . 0.883(19) 1.86(2) 2.747(4) 176.(4) ?
O2 H1O2 O1 2_646 0.881(19) 1.87(2) 2.748(4) 175.(4) ?
O2 H2O2 O3 . 0.876(19) 1.89(3) 2.719(4) 156.(4) ?
O3 H1O3 O2 3_656 0.872(19) 1.91(2) 2.772(4) 169.(5) ?
O3 H2O3 O1 4 0.884(19) 1.89(2) 2.767(4) 175.(4) ?
####################################################################### 
# 
# 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_4-Methylpiperidine_hemihydrate_175K
_database_code_depnum_ccdc_archive 'CCDC 2026857'
loop_
_audit_author_name
_audit_author_address
'Pawel Socha'
; Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-Methylpiperidine_hemihydrate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H28 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         216.36

_chemical_melting_point          253

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.3447(4)
_cell_length_b                   23.720(2)
_cell_length_c                   11.2047(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.241(2)
_cell_angle_gamma                90
_cell_volume                     1402.05(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      3.1674
_cell_measurement_theta_max      26.3025
_cell_measurement_temperature    175.(2)

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488

_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'TWINABS-2012/1 (Bruker AXS Inc., 2012)'
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      175.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            2391
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2391
_reflns_number_gt                1977
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1402
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_number_reflns         2391
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+0.6417P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.036(6)

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'

_computing_data_collection       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4181(2) 0.58806(6) 0.49398(13) 0.0405(4) Uani d . . . 1 . .
H H1 0.539(5) 0.6007(11) 0.468(2) 0.061 Uiso d U . . 1 . .
H H2 0.484(4) 0.5678(10) 0.561(2) 0.061 Uiso d U . . 1 . .
N N1 0.6964(3) 0.51308(7) 0.68154(14) 0.0388(4) Uani d . . . 1 . .
H H1N1 0.658(4) 0.4830(10) 0.641(2) 0.058 Uiso d U . . 1 . .
C C2 0.6892(4) 0.50247(8) 0.80978(17) 0.0419(5) Uani d . . . 1 . .
H H2A 0.8111 0.4722 0.8393 0.05 Uiso calc U . R 1 . .
H H2B 0.5176 0.4896 0.8197 0.05 Uiso calc U . R 1 . .
C C3 0.7557(3) 0.55547(8) 0.88428(16) 0.0397(5) Uani d . . . 1 . .
H H3A 0.7561 0.5469 0.9708 0.048 Uiso calc U . R 1 . .
H H3B 0.6249 0.5846 0.8595 0.048 Uiso calc U . R 1 . .
C C4 1.0148(3) 0.57841(7) 0.86800(15) 0.0338(4) Uani d . . . 1 . .
H H4 1.1448 0.5495 0.9 0.041 Uiso calc U . R 1 . .
C C5 1.0223(3) 0.58575(7) 0.73297(15) 0.0350(4) Uani d . . . 1 . .
H H5A 0.9041 0.6162 0.7005 0.042 Uiso calc U . R 1 . .
H H5B 1.1952 0.5971 0.7217 0.042 Uiso calc U . R 1 . .
C C6 0.9495(3) 0.53180(7) 0.66289(16) 0.0363(4) Uani d . . . 1 . .
H H6A 0.9498 0.5384 0.5757 0.044 Uiso calc U . R 1 . .
H H6B 1.0755 0.502 0.6903 0.044 Uiso calc U . R 1 . .
C C7 1.0810(4) 0.63288(9) 0.93825(18) 0.0503(5) Uani d . . . 1 . .
H H7A 1.2484 0.646 0.9252 0.075 Uiso calc U . R 1 . .
H H7B 1.0832 0.626 1.0246 0.075 Uiso calc U . R 1 . .
H H7C 0.9538 0.6617 0.91 0.075 Uiso calc U . R 1 . .
N N2 0.8645(3) 0.63845(7) 0.41549(15) 0.0426(4) Uani d . . . 1 . .
H H1N2 1.000(5) 0.6226(10) 0.457(2) 0.064 Uiso d U . . 1 . .
C C8 0.8675(4) 0.69712(9) 0.45641(17) 0.0445(5) Uani d . . . 1 . .
H H8A 1.0235 0.716 0.4397 0.053 Uiso calc U . R 1 . .
H H8B 0.8672 0.6983 0.5447 0.053 Uiso calc U . R 1 . .
C C9 0.6368(3) 0.72765(8) 0.39111(16) 0.0385(5) Uani d . . . 1 . .
H H9A 0.6401 0.7673 0.4188 0.046 Uiso calc U . R 1 . .
H H9B 0.4817 0.7098 0.4115 0.046 Uiso calc U . R 1 . .
C C10 0.6281(3) 0.72627(8) 0.25513(16) 0.0372(5) Uani d . . . 1 . .
H H10 0.7824 0.746 0.2364 0.045 Uiso calc U . R 1 . .
C C11 0.6406(4) 0.66533(9) 0.21497(16) 0.0425(5) Uani d . . . 1 . .
H H11A 0.6505 0.6642 0.1275 0.051 Uiso calc U . R 1 . .
H H11B 0.484 0.6455 0.2276 0.051 Uiso calc U . R 1 . .
C C12 0.8693(4) 0.63529(8) 0.28501(18) 0.0428(5) Uani d . . . 1 . .
H H12A 0.8684 0.5953 0.2596 0.051 Uiso calc U . R 1 . .
H H12B 1.0267 0.6529 0.2668 0.051 Uiso calc U . R 1 . .
C C13 0.3954(4) 0.75678(11) 0.1876(2) 0.0622(7) Uani d . . . 1 . .
H H13A 0.3943 0.7537 0.1003 0.093 Uiso calc U . R 1 . .
H H13B 0.4016 0.7966 0.211 0.093 Uiso calc U . R 1 . .
H H13C 0.2412 0.7395 0.2081 0.093 Uiso calc U . R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0253(7) 0.0474(8) 0.0474(8) -0.0014(5) 0.0019(5) 0.0089(6)
N1 0.0346(9) 0.0419(9) 0.0374(9) -0.0046(7) -0.0021(6) 0.0018(7)
C2 0.0332(10) 0.0474(11) 0.0447(11) -0.0052(8) 0.0048(8) 0.0094(8)
C3 0.0326(10) 0.0521(11) 0.0349(9) 0.0042(8) 0.0073(7) 0.0036(8)
C4 0.0277(9) 0.0385(10) 0.0342(9) 0.0049(7) 0.0025(7) 0.0005(7)
C5 0.0313(10) 0.0373(10) 0.0364(10) -0.0001(7) 0.0059(7) 0.0024(7)
C6 0.0363(10) 0.0393(10) 0.0339(9) 0.0024(7) 0.0075(7) -0.0001(7)
C7 0.0521(13) 0.0514(12) 0.0465(11) 0.0009(9) 0.0052(9) -0.0146(9)
N2 0.0256(9) 0.0504(10) 0.0511(10) 0.0050(7) 0.0044(7) 0.0197(8)
C8 0.0322(10) 0.0624(13) 0.0373(10) -0.0111(9) 0.0005(8) 0.0003(9)
C9 0.0331(10) 0.0381(10) 0.0466(11) -0.0034(7) 0.0133(8) -0.0041(8)
C10 0.0225(9) 0.0450(10) 0.0470(11) 0.0064(7) 0.0143(7) 0.0152(8)
C11 0.0340(10) 0.0603(13) 0.0333(10) 0.0044(8) 0.0060(7) -0.0039(8)
C12 0.0337(10) 0.0398(11) 0.0574(12) 0.0080(8) 0.0148(8) 0.0016(9)
C13 0.0402(12) 0.0827(17) 0.0673(14) 0.0238(11) 0.0196(10) 0.0379(12)

_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
O1 H1 . 0.81(3) ?
O1 H2 . 0.91(3) ?
N1 C2 . 1.465(2) ?
N1 C6 . 1.470(2) ?
N1 H1N1 . 0.86(2) ?
C2 C3 . 1.519(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.526(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C7 . 1.525(2) ?
C4 C5 . 1.530(2) ?
C4 H4 . 1.0 ?
C5 C6 . 1.519(2) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
N2 C8 . 1.465(3) ?
N2 C12 . 1.468(2) ?
N2 H1N2 . 0.88(3) ?
C8 C9 . 1.514(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.517(2) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C11 . 1.519(3) ?
C10 C13 . 1.530(3) ?
C10 H10 . 1.0 ?
C11 C12 . 1.520(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?

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
H1 O1 H2 . . 106.(2) ?
C2 N1 C6 . . 111.14(14) ?
C2 N1 H1N1 . . 110.0(16) ?
C6 N1 H1N1 . . 108.7(16) ?
N1 C2 C3 . . 110.86(15) ?
N1 C2 H2A . . 109.5 ?
C3 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 108.1 ?
C2 C3 C4 . . 111.46(15) ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3B . . 109.3 ?
C4 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
C7 C4 C3 . . 112.34(15) ?
C7 C4 C5 . . 111.92(15) ?
C3 C4 C5 . . 109.09(14) ?
C7 C4 H4 . . 107.8 ?
C3 C4 H4 . . 107.8 ?
C5 C4 H4 . . 107.8 ?
C6 C5 C4 . . 111.73(14) ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5B . . 109.3 ?
C4 C5 H5B . . 109.3 ?
H5A C5 H5B . . 107.9 ?
N1 C6 C5 . . 110.24(14) ?
N1 C6 H6A . . 109.6 ?
C5 C6 H6A . . 109.6 ?
N1 C6 H6B . . 109.6 ?
C5 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C8 N2 C12 . . 111.05(14) ?
C8 N2 H1N2 . . 106.1(16) ?
C12 N2 H1N2 . . 111.0(16) ?
N2 C8 C9 . . 109.65(15) ?
N2 C8 H8A . . 109.7 ?
C9 C8 H8A . . 109.7 ?
N2 C8 H8B . . 109.7 ?
C9 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
C8 C9 C10 . . 111.49(14) ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9B . . 109.3 ?
C10 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
C9 C10 C11 . . 108.80(14) ?
C9 C10 C13 . . 112.22(15) ?
C11 C10 C13 . . 112.00(18) ?
C9 C10 H10 . . 107.9 ?
C11 C10 H10 . . 107.9 ?
C13 C10 H10 . . 107.9 ?
C10 C11 C12 . . 111.31(15) ?
C10 C11 H11A . . 109.4 ?
C12 C11 H11A . . 109.4 ?
C10 C11 H11B . . 109.4 ?
C12 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
N2 C12 C11 . . 110.44(14) ?
N2 C12 H12A . . 109.6 ?
C11 C12 H12A . . 109.6 ?
N2 C12 H12B . . 109.6 ?
C11 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . 59.72(19) ?
N1 C2 C3 C4 . . . . -56.8(2) ?
C2 C3 C4 C7 . . . . 177.82(15) ?
C2 C3 C4 C5 . . . . 53.11(19) ?
C7 C4 C5 C6 . . . . -178.50(15) ?
C3 C4 C5 C6 . . . . -53.55(19) ?
C2 N1 C6 C5 . . . . -59.65(19) ?
C4 C5 C6 N1 . . . . 57.07(18) ?
C12 N2 C8 C9 . . . . 60.36(19) ?
N2 C8 C9 C10 . . . . -58.72(19) ?
C8 C9 C10 C11 . . . . 55.30(19) ?
C8 C9 C10 C13 . . . . 179.80(17) ?
C9 C10 C11 C12 . . . . -54.03(19) ?
C13 C10 C11 C12 . . . . -178.66(15) ?
C8 N2 C12 C11 . . . . -59.6(2) ?
C10 C11 C12 N2 . . . . 56.7(2) ?

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
O1 H1 N2 . 0.81(3) 2.12(3) 2.927(2) 174.(2) ?
O1 H2 N1 . 0.91(3) 2.08(3) 2.965(2) 164.(2) ?
N1 H1N1 O1 3_666 0.86(2) 2.25(2) 3.100(2) 170.(2) ?
N2 H1N2 O1 1_655 0.88(3) 2.36(3) 3.181(2) 157.(2) ?
####################################################################### 
# 
# 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_4-Methylpiperidine_trihydrate_100K
_database_code_depnum_ccdc_archive 'CCDC 2026858'
loop_
_audit_author_name
_audit_author_address
'Pawel Socha'
; Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-Methylpiperidine_trihydrate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H19 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         153.22

_chemical_melting_point          263

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.176(3)
_cell_length_b                   6.3382(11)
_cell_length_c                   11.846(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.596(7)
_cell_angle_gamma                90
_cell_volume                     961.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7592
_cell_measurement_theta_min      3.1852
_cell_measurement_theta_max      30.0394
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.5113
_exptl_absorpt_correction_T_max  0.7461

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            11101
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             1684
_reflns_number_gt                1518
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1083
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.141
_refine_ls_number_reflns         1684
_refine_ls_number_parameters     114
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.5540P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.079(9)

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'
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'

_computing_data_collection       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.75001(10) 0.8763(2) 0.45552(11) 0.0188(3) Uani d . . . 1 . .
H H1N1 0.7322(15) 0.966(3) 0.5045(17) 0.028 Uiso d U . . 1 . .
C C2 0.86391(11) 0.8831(2) 0.47064(13) 0.0198(4) Uani d . . . 1 . .
H H2A 0.8987 0.8299 0.5487 0.024 Uiso calc U . R 1 . .
H H2B 0.8868 1.0304 0.464 0.024 Uiso calc U . R 1 . .
C C3 0.89423(11) 0.7477(2) 0.37818(13) 0.0186(4) Uani d . . . 1 . .
H H3A 0.971 0.7508 0.3888 0.022 Uiso calc U . R 1 . .
H H3B 0.8623 0.8065 0.3005 0.022 Uiso calc U . R 1 . .
C C4 0.85832(11) 0.5197(2) 0.38425(12) 0.0165(4) Uani d . . . 1 . .
H H4 0.8971 0.4587 0.46 0.02 Uiso calc U . R 1 . .
C C5 0.74171(12) 0.5151(2) 0.38154(13) 0.0193(4) Uani d . . . 1 . .
H H5A 0.7014 0.5585 0.3036 0.023 Uiso calc U . R 1 . .
H H5B 0.721 0.3691 0.3956 0.023 Uiso calc U . R 1 . .
C C6 0.71514(12) 0.6610(3) 0.47265(14) 0.0224(4) Uani d . . . 1 . .
H H6A 0.6388 0.6603 0.4659 0.027 Uiso calc U . R 1 . .
H H6B 0.75 0.6107 0.5513 0.027 Uiso calc U . R 1 . .
C C7 0.88332(14) 0.3869(3) 0.28674(14) 0.0277(4) Uani d . . . 1 . .
H H7A 0.8473 0.4458 0.2115 0.042 Uiso calc U . R 1 . .
H H7B 0.8599 0.2415 0.293 0.042 Uiso calc U . R 1 . .
H H7C 0.9588 0.3881 0.2931 0.042 Uiso calc U . R 1 . .
O O1 0.62487(9) 1.02283(16) 0.24612(9) 0.0175(3) Uani d . . . 1 . .
H H1O1 0.6655(16) 0.981(3) 0.3061(18) 0.026 Uiso d U . . 1 . .
H H2O1 0.5951(15) 0.924(3) 0.2131(17) 0.026 Uiso d U . . 1 . .
O O2 0.51274(9) 0.68766(17) 0.13357(9) 0.0180(3) Uani d . . . 1 . .
H H1O2 0.4705(16) 0.650(3) 0.1735(17) 0.027 Uiso d U . . 1 . .
H H2O2 0.5501(16) 0.587(3) 0.1278(17) 0.027 Uiso d U . . 1 . .
O O3 0.62387(9) 0.34052(17) 0.08458(10) 0.0196(3) Uani d . . D 1 . .
H H1O3 0.5857(14) 0.303(3) 0.0219(15) 0.029 Uiso d U . D 1 . .
H H2O3 0.6320(15) 0.251(4) 0.1310(18) 0.029 Uiso d U . . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0204(7) 0.0183(7) 0.0171(6) 0.0036(5) 0.0031(5) -0.0051(5)
C2 0.0200(8) 0.0170(7) 0.0189(8) -0.0030(6) -0.0024(6) -0.0008(6)
C3 0.0143(7) 0.0224(8) 0.0191(7) -0.0007(6) 0.0036(5) 0.0036(6)
C4 0.0194(8) 0.0167(7) 0.0125(7) 0.0048(6) 0.0022(5) 0.0026(5)
C5 0.0203(8) 0.0156(7) 0.0223(8) -0.0041(6) 0.0057(6) -0.0021(6)
C6 0.0205(8) 0.0259(8) 0.0237(8) -0.0022(6) 0.0107(6) -0.0008(6)
C7 0.0354(9) 0.0270(9) 0.0216(8) 0.0125(7) 0.0086(7) -0.0002(6)
O1 0.0224(6) 0.0118(5) 0.0162(6) -0.0019(4) 0.0004(4) -0.0005(4)
O2 0.0203(6) 0.0155(6) 0.0180(6) -0.0014(4) 0.0040(4) -0.0011(4)
O3 0.0267(6) 0.0177(6) 0.0134(5) -0.0010(4) 0.0025(4) 0.0032(4)

_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
N1 C6 . 1.469(2) ?
N1 C2 . 1.470(2) ?
N1 H1N1 . 0.88(2) ?
C2 C3 . 1.517(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.527(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C7 . 1.527(2) ?
C4 C5 . 1.530(2) ?
C4 H4 . 1.0 ?
C5 C6 . 1.523(2) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
O1 H1O1 . 0.83(2) ?
O1 H2O1 . 0.79(2) ?
O2 H1O2 . 0.84(2) ?
O2 H2O2 . 0.82(2) ?
O3 H1O3 . 0.828(15) ?
O3 H2O3 . 0.78(2) ?

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
C6 N1 C2 . . 110.73(12) ?
C6 N1 H1N1 . . 111.7(13) ?
C2 N1 H1N1 . . 108.8(12) ?
N1 C2 C3 . . 109.27(11) ?
N1 C2 H2A . . 109.8 ?
C3 C2 H2A . . 109.8 ?
N1 C2 H2B . . 109.8 ?
C3 C2 H2B . . 109.8 ?
H2A C2 H2B . . 108.3 ?
C2 C3 C4 . . 111.36(12) ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3B . . 109.4 ?
C4 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C7 C4 C3 . . 111.21(12) ?
C7 C4 C5 . . 111.58(12) ?
C3 C4 C5 . . 109.75(11) ?
C7 C4 H4 . . 108.1 ?
C3 C4 H4 . . 108.1 ?
C5 C4 H4 . . 108.1 ?
C6 C5 C4 . . 111.74(12) ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5B . . 109.3 ?
C4 C5 H5B . . 109.3 ?
H5A C5 H5B . . 107.9 ?
N1 C6 C5 . . 109.56(12) ?
N1 C6 H6A . . 109.8 ?
C5 C6 H6A . . 109.8 ?
N1 C6 H6B . . 109.8 ?
C5 C6 H6B . . 109.8 ?
H6A C6 H6B . . 108.2 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
H1O1 O1 H2O1 . . 108.2(19) ?
H1O2 O2 H2O2 . . 108.2(19) ?
H1O3 O3 H2O3 . . 112.(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . 63.16(15) ?
N1 C2 C3 C4 . . . . -58.38(15) ?
C2 C3 C4 C7 . . . . 176.70(12) ?
C2 C3 C4 C5 . . . . 52.74(15) ?
C7 C4 C5 C6 . . . . -175.51(12) ?
C3 C4 C5 C6 . . . . -51.77(16) ?
C2 N1 C6 C5 . . . . -62.10(16) ?
C4 C5 C6 N1 . . . . 56.41(16) ?

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 H1N1 O3 4_576 0.88(2) 2.25(2) 3.0848(17) 156.8(17) ?
O1 H1O1 N1 . 0.83(2) 1.97(2) 2.7949(17) 174.2(19) ?
O1 H2O1 O2 . 0.79(2) 1.96(2) 2.7472(15) 176.(2) ?
O2 H1O2 O1 2_645 0.84(2) 1.92(2) 2.7613(16) 171.3(19) ?
O2 H2O2 O3 . 0.82(2) 1.97(2) 2.7788(16) 169.4(19) ?
O3 H1O3 O2 3_665 0.828(15) 1.989(16) 2.7862(15) 161.3(19) ?
O3 H2O3 O1 1_545 0.78(2) 2.01(2) 2.7758(16) 170.(2) ?
####################################################################### 
# 
# 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_4-Methylpiperidine_trihydrate_200K
_database_code_depnum_ccdc_archive 'CCDC 2026859'
loop_
_audit_author_name
_audit_author_address
'Pawel Socha'
; Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-Methylpiperidine_trihydrate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H19 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         153.22

_chemical_melting_point          263

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2473(10)
_cell_length_b                   6.3988(4)
_cell_length_c                   11.8886(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.251(2)
_cell_angle_gamma                90
_cell_volume                     980.93(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5635
_cell_measurement_theta_min      3.1598
_cell_measurement_theta_max      27.7603
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.038
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.5284
_exptl_absorpt_correction_T_max  0.7457

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            11408
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             1723
_reflns_number_gt                1472
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1113
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.072
_refine_ls_number_reflns         1723
_refine_ls_number_parameters     114
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.3619P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.090(10)

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'
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'

_computing_data_collection       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.74857(11) 0.8752(2) 0.45248(12) 0.0396(4) Uani d . . . 1 . .
H H1N1 0.7299(16) 0.962(3) 0.4992(19) 0.059 Uiso d U . . 1 . .
C C2 0.86132(13) 0.8814(3) 0.46967(14) 0.0433(4) Uani d . . . 1 . .
H H2A 0.8943 0.829 0.5478 0.052 Uiso calc U . R 1 . .
H H2B 0.8844 1.0271 0.4633 0.052 Uiso calc U . R 1 . .
C C3 0.89348(12) 0.7472(3) 0.37940(14) 0.0412(4) Uani d . . . 1 . .
H H3A 0.97 0.7498 0.3918 0.049 Uiso calc U . R 1 . .
H H3B 0.8636 0.8056 0.3018 0.049 Uiso calc U . R 1 . .
C C4 0.85737(12) 0.5222(2) 0.38424(13) 0.0359(4) Uani d . . . 1 . .
H H4 0.8941 0.4616 0.4601 0.043 Uiso calc U . R 1 . .
C C5 0.74143(12) 0.5189(3) 0.37921(14) 0.0412(4) Uani d . . . 1 . .
H H5A 0.703 0.5621 0.3012 0.049 Uiso calc U . R 1 . .
H H5B 0.7201 0.3745 0.3927 0.049 Uiso calc U . R 1 . .
C C6 0.71319(14) 0.6631(3) 0.46846(16) 0.0478(5) Uani d . . . 1 . .
H H6A 0.6371 0.6629 0.4601 0.057 Uiso calc U . R 1 . .
H H6B 0.7462 0.6131 0.5471 0.057 Uiso calc U . R 1 . .
C C7 0.88418(17) 0.3895(3) 0.28863(17) 0.0600(6) Uani d . . . 1 . .
H H7A 0.8492 0.4463 0.2132 0.09 Uiso calc U . R 1 . .
H H7B 0.8613 0.2454 0.2954 0.09 Uiso calc U . R 1 . .
H H7C 0.9594 0.3916 0.2958 0.09 Uiso calc U . R 1 . .
O O1 0.62400(9) 1.02250(16) 0.24406(10) 0.0364(3) Uani d . . . 1 . .
H H1O1 0.6656(16) 0.977(3) 0.3043(19) 0.055 Uiso d U . . 1 . .
H H2O1 0.5940(16) 0.923(4) 0.2118(18) 0.055 Uiso d U . . 1 . .
O O2 0.51263(9) 0.68734(17) 0.13417(9) 0.0366(3) Uani d . . . 1 . .
H H1O2 0.4698(16) 0.647(3) 0.1747(18) 0.055 Uiso d U . . 1 . .
H H2O2 0.5478(17) 0.592(4) 0.1262(18) 0.055 Uiso d U . . 1 . .
O O3 0.62217(9) 0.34028(18) 0.08341(10) 0.0395(3) Uani d . . D 1 . .
H H1O3 0.5832(15) 0.307(3) 0.0211(15) 0.059 Uiso d U . D 1 . .
H H2O3 0.6273(16) 0.246(4) 0.1306(19) 0.059 Uiso d U . . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0440(8) 0.0387(8) 0.0349(7) 0.0079(6) 0.0064(6) -0.0071(6)
C2 0.0425(9) 0.0389(9) 0.0415(9) -0.0043(7) -0.0051(7) -0.0031(7)
C3 0.0298(8) 0.0498(10) 0.0439(9) -0.0019(7) 0.0082(6) 0.0065(7)
C4 0.0405(9) 0.0366(8) 0.0294(7) 0.0105(6) 0.0057(6) 0.0051(6)
C5 0.0418(9) 0.0334(8) 0.0485(9) -0.0072(7) 0.0108(7) -0.0032(7)
C6 0.0443(9) 0.0538(11) 0.0509(10) -0.0016(8) 0.0227(8) 0.0014(8)
C7 0.0749(13) 0.0602(12) 0.0473(10) 0.0269(10) 0.0190(9) -0.0011(9)
O1 0.0459(7) 0.0269(6) 0.0335(6) -0.0032(5) 0.0029(5) -0.0005(4)
O2 0.0402(6) 0.0333(6) 0.0352(6) -0.0033(5) 0.0061(5) -0.0026(5)
O3 0.0508(7) 0.0370(6) 0.0287(6) -0.0021(5) 0.0050(5) 0.0045(5)

_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
N1 C2 . 1.461(2) ?
N1 C6 . 1.462(2) ?
N1 H1N1 . 0.86(2) ?
C2 C3 . 1.510(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.522(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.523(2) ?
C4 C7 . 1.524(2) ?
C4 H4 . 1.0 ?
C5 C6 . 1.516(2) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
O1 H1O1 . 0.85(2) ?
O1 H2O1 . 0.80(2) ?
O2 H1O2 . 0.86(2) ?
O2 H2O2 . 0.79(2) ?
O3 H1O3 . 0.828(16) ?
O3 H2O3 . 0.82(2) ?

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 N1 C6 . . 110.77(13) ?
C2 N1 H1N1 . . 109.2(14) ?
C6 N1 H1N1 . . 111.5(14) ?
N1 C2 C3 . . 109.34(12) ?
N1 C2 H2A . . 109.8 ?
C3 C2 H2A . . 109.8 ?
N1 C2 H2B . . 109.8 ?
C3 C2 H2B . . 109.8 ?
H2A C2 H2B . . 108.3 ?
C2 C3 C4 . . 111.63(13) ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3B . . 109.3 ?
C4 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
C3 C4 C5 . . 109.55(12) ?
C3 C4 C7 . . 111.68(14) ?
C5 C4 C7 . . 111.59(14) ?
C3 C4 H4 . . 108.0 ?
C5 C4 H4 . . 108.0 ?
C7 C4 H4 . . 108.0 ?
C6 C5 C4 . . 111.85(13) ?
C6 C5 H5A . . 109.2 ?
C4 C5 H5A . . 109.2 ?
C6 C5 H5B . . 109.2 ?
C4 C5 H5B . . 109.2 ?
H5A C5 H5B . . 107.9 ?
N1 C6 C5 . . 109.65(13) ?
N1 C6 H6A . . 109.7 ?
C5 C6 H6A . . 109.7 ?
N1 C6 H6B . . 109.7 ?
C5 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
H1O1 O1 H2O1 . . 106.(2) ?
H1O2 O2 H2O2 . . 108.(2) ?
H1O3 O3 H2O3 . . 111.(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . 62.90(17) ?
N1 C2 C3 C4 . . . . -58.19(17) ?
C2 C3 C4 C5 . . . . 52.48(17) ?
C2 C3 C4 C7 . . . . 176.63(14) ?
C3 C4 C5 C6 . . . . -51.58(18) ?
C7 C4 C5 C6 . . . . -175.78(14) ?
C2 N1 C6 C5 . . . . -62.02(18) ?
C4 C5 C6 N1 . . . . 56.44(19) ?



#===END
