# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DCK
_database_code_depnum_ccdc_archive 'CCDC 1838630'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems DTC. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   6.4939(3)
_cell_length_b                   13.2876(6)
_cell_length_c                   14.9655(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.9591(12)
_cell_angle_gamma                90
_cell_volume                     1289.63(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C13 H18 Cl1 N1 O1 
# Dc =      1.23 Fooo =    512.00 Mu =     24.50 M =    239.74
# Found Formula = C13 H18 Cl1 N1 O1 
# Dc =      1.23 FOOO =    512.00 Mu =     24.50 M =    239.74

_chemical_formula_sum            'C13 H18 Cl1 N1 O1'
_chemical_formula_moiety         'C13 H18 Cl1 N1 O1'
_chemical_compound_source        ?
_chemical_formula_weight         239.74


_cell_measurement_reflns_used    96
_cell_measurement_theta_min      11
_cell_measurement_theta_max      58
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.185
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_max          0.481

_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    2.450

# Sheldrick geometric approximatio 0.62 0.64 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.64
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            20050
_reflns_number_total             2352
_diffrn_reflns_av_R_equivalents  0.035
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2352 
# Theoretical number of reflections is about 4720 


_diffrn_reflns_theta_min         4.452
_diffrn_reflns_theta_max         68.211
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        68.211
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.36
_oxford_diffrn_Wilson_scale      17.92

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.23


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     7
_refine_ls_number_parameters     152
_oxford_refine_ls_R_factor_ref   0.0384
_refine_ls_wR_factor_ref         0.0895
_refine_ls_goodness_of_fit_ref   0.9535
_refine_ls_shift/su_max          0.0009002
_refine_ls_shift/su_mean         0.0000376


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2352
_refine_ls_R_factor_all          0.0384
_refine_ls_wR_factor_all         0.0895

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2299
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_gt          0.0892

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 11.1 18.3 10.7 4.30 0.926 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.34424(7) 0.03135(3) 0.64510(3) 0.0282 1.0000 Uani . . . . . .
O1 O 0.2921(2) 0.17768(11) 0.44538(9) 0.0390 1.0000 Uani . . . . . .
N1 N 0.6526(2) 0.11927(10) 0.51214(9) 0.0221 1.0000 Uani D . . . . .
C1 C 0.6828(3) 0.29625(12) 0.56029(11) 0.0250 1.0000 Uani . . . . . .
C2 C 0.5320(3) 0.30693(15) 0.62203(13) 0.0361 1.0000 Uani . . . . . .
C3 C 0.5705(4) 0.36517(16) 0.69855(14) 0.0480 1.0000 Uani . . . . . .
C4 C 0.7581(4) 0.41135(16) 0.71390(14) 0.0478 1.0000 Uani . . . . . .
C5 C 0.9079(4) 0.40102(16) 0.65348(14) 0.0439 1.0000 Uani . . . . . .
C6 C 0.8713(3) 0.34381(15) 0.57640(13) 0.0355 1.0000 Uani . . . . . .
C7 C 0.6417(3) 0.22660(12) 0.47986(11) 0.0220 1.0000 Uani D . . . . .
C8 C 0.4211(3) 0.24229(14) 0.43953(11) 0.0266 1.0000 Uani . . . . . .
C9 C 0.3845(3) 0.33960(16) 0.38955(14) 0.0385 1.0000 Uani . . . . . .
C10 C 0.5375(3) 0.34800(16) 0.31505(13) 0.0392 1.0000 Uani . . . . . .
C11 C 0.7581(3) 0.33850(15) 0.35345(12) 0.0337 1.0000 Uani . . . . . .
C12 C 0.7889(3) 0.23894(14) 0.40331(11) 0.0274 1.0000 Uani . . . . . .
C13 C 0.8441(3) 0.08991(14) 0.56443(12) 0.0307 1.0000 Uani D . . . . .
H11 H 0.636(3) 0.0792(12) 0.4637(10) 0.0327 1.0000 Uiso D . . . . .
H12 H 0.546(2) 0.1075(12) 0.5471(11) 0.0329 1.0000 Uiso D . . . . .
H21 H 0.4036 0.2747 0.6115 0.0420 1.0000 Uiso R . . . . .
H31 H 0.4660 0.3736 0.7373 0.0589 1.0000 Uiso R . . . . .
H41 H 0.7826 0.4507 0.7653 0.0575 1.0000 Uiso R . . . . .
H51 H 1.0368 0.4321 0.6649 0.0540 1.0000 Uiso R . . . . .
H61 H 0.9781 0.3371 0.5355 0.0434 1.0000 Uiso R . . . . .
H91 H 0.4093 0.3952 0.4307 0.0468 1.0000 Uiso R . . . . .
H92 H 0.2405 0.3411 0.3650 0.0473 1.0000 Uiso R . . . . .
H101 H 0.5208 0.4122 0.2857 0.0471 1.0000 Uiso R . . . . .
H102 H 0.5091 0.2958 0.2710 0.0473 1.0000 Uiso R . . . . .
H111 H 0.8484 0.3415 0.3041 0.0404 1.0000 Uiso R . . . . .
H112 H 0.7862 0.3942 0.3941 0.0395 1.0000 Uiso R . . . . .
H121 H 0.7550 0.1849 0.3606 0.0332 1.0000 Uiso R . . . . .
H122 H 0.9304 0.2294 0.4244 0.0337 1.0000 Uiso R . . . . .
H131 H 0.8392 0.0189 0.5751 0.0448 1.0000 Uiso R . . . . .
H132 H 0.8462 0.1238 0.6208 0.0465 1.0000 Uiso R . . . . .
H133 H 0.9660 0.1067 0.5316 0.0457 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2492(3)

loop_
_oxford_twin_element_scale_factors
0.821(2)
0.179(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C8 . 1.206(2) yes
N1 . C7 . 1.506(2) yes
N1 . C13 . 1.487(2) yes
N1 . H11 . 0.902(15) no
N1 . H12 . 0.904(15) no
C1 . C2 . 1.388(3) yes
C1 . C6 . 1.388(3) yes
C1 . C7 . 1.531(2) yes
C2 . C3 . 1.394(3) yes
C2 . H21 . 0.944 no
C3 . C4 . 1.373(4) yes
C3 . H31 . 0.922 no
C4 . C5 . 1.369(3) yes
C4 . H41 . 0.937 no
C5 . C6 . 1.392(3) yes
C5 . H51 . 0.941 no
C6 . H61 . 0.952 no
C7 . C8 . 1.540(2) yes
C7 . C12 . 1.538(2) yes
C8 . C9 . 1.506(3) yes
C9 . C10 . 1.535(3) yes
C9 . H91 . 0.970 no
C9 . H92 . 0.987 no
C10 . C11 . 1.521(3) yes
C10 . H101 . 0.962 no
C10 . H102 . 0.968 no
C11 . C12 . 1.527(2) yes
C11 . H111 . 0.968 no
C11 . H112 . 0.969 no
C12 . H121 . 0.979 no
C12 . H122 . 0.964 no
C13 . H131 . 0.957 no
C13 . H132 . 0.956 no
C13 . H133 . 0.979 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . N1 . C13 . 116.18(13) yes
C7 . N1 . H11 . 107.4(10) no
C13 . N1 . H11 . 109.4(10) no
C7 . N1 . H12 . 108.9(10) no
C13 . N1 . H12 . 107.2(10) no
H11 . N1 . H12 . 107.4(13) no
C2 . C1 . C6 . 118.96(17) yes
C2 . C1 . C7 . 119.01(16) yes
C6 . C1 . C7 . 121.89(16) yes
C1 . C2 . C3 . 120.1(2) yes
C1 . C2 . H21 . 119.4 no
C3 . C2 . H21 . 120.5 no
C2 . C3 . C4 . 120.3(2) yes
C2 . C3 . H31 . 118.6 no
C4 . C3 . H31 . 121.1 no
C3 . C4 . C5 . 119.96(19) yes
C3 . C4 . H41 . 119.9 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 120.4(2) yes
C4 . C5 . H51 . 119.4 no
C6 . C5 . H51 . 120.2 no
C5 . C6 . C1 . 120.3(2) yes
C5 . C6 . H61 . 119.0 no
C1 . C6 . H61 . 120.7 no
C1 . C7 . N1 . 108.48(13) yes
C1 . C7 . C8 . 110.32(14) yes
N1 . C7 . C8 . 106.33(13) yes
C1 . C7 . C12 . 115.55(14) yes
N1 . C7 . C12 . 108.62(13) yes
C8 . C7 . C12 . 107.15(13) yes
C7 . C8 . O1 . 120.72(16) yes
C7 . C8 . C9 . 115.51(15) yes
O1 . C8 . C9 . 123.69(16) yes
C8 . C9 . C10 . 109.37(16) yes
C8 . C9 . H91 . 108.8 no
C10 . C9 . H91 . 108.3 no
C8 . C9 . H92 . 108.9 no
C10 . C9 . H92 . 111.4 no
H91 . C9 . H92 . 110.1 no
C9 . C10 . C11 . 110.59(16) yes
C9 . C10 . H101 . 109.5 no
C11 . C10 . H101 . 109.1 no
C9 . C10 . H102 . 109.5 no
C11 . C10 . H102 . 109.9 no
H101 . C10 . H102 . 108.2 no
C10 . C11 . C12 . 110.72(15) yes
C10 . C11 . H111 . 107.7 no
C12 . C11 . H111 . 109.9 no
C10 . C11 . H112 . 108.5 no
C12 . C11 . H112 . 109.8 no
H111 . C11 . H112 . 110.2 no
C7 . C12 . C11 . 112.67(14) yes
C7 . C12 . H121 . 106.3 no
C11 . C12 . H121 . 107.3 no
C7 . C12 . H122 . 111.1 no
C11 . C12 . H122 . 111.9 no
H121 . C12 . H122 . 107.2 no
N1 . C13 . H131 . 108.2 no
N1 . C13 . H132 . 108.3 no
H131 . C13 . H132 . 108.4 no
N1 . C13 . H133 . 110.6 no
H131 . C13 . H133 . 110.1 no
H132 . C13 . H133 . 111.1 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 . H122 . O1 1_655 165.69(5) 0.964 2.452 3.395(3) yes


_chemical_name_systematic        (RS)-deschloroketamine
####################################################################### 
# 
# 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_SDCK
_database_code_depnum_ccdc_archive 'CCDC 1838631'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   6.5215(3)
_cell_length_b                   13.1197(5)
_cell_length_c                   15.0635(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.4163(8)
_cell_angle_gamma                90
_cell_volume                     1288.44(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C13 H18 Cl1 N1 O1 
# Dc =      1.24 Fooo =    512.00 Mu =     24.52 M =    479.49
# Found Formula = C13 H18.00 Cl1 N1 O1 
# Dc =      1.24 FOOO =    512.00 Mu =     24.52 M =    479.49

_chemical_formula_sum            'C13 H18.00 Cl1 N1 O1'
_chemical_formula_moiety         'C13 H18.00 Cl1 N1 O1'
_chemical_compound_source        ?
_chemical_formula_weight         239.74


_cell_measurement_reflns_used    106
_cell_measurement_theta_min      14
_cell_measurement_theta_max      59
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.374
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_max          0.467

_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             511.996
_exptl_absorpt_coefficient_mu    2.452

# Sheldrick geometric approximatio 0.35 0.40 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.34
_exptl_absorpt_correction_T_max  0.40
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            21595
_reflns_number_total             4737
_diffrn_reflns_av_R_equivalents  0.026
# Number of reflections without Friedels Law is 4737 
# Number of reflections with Friedels Law is 2551 
# Theoretical number of reflections is about 2445 


_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         70.034
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        70.034
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              -15
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   1.78
_oxford_diffrn_Wilson_scale      9.45

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.21


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     15
_refine_ls_number_parameters     303
_oxford_refine_ls_R_factor_ref   0.0253
_refine_ls_wR_factor_ref         0.0677
_refine_ls_goodness_of_fit_ref   0.9997
_refine_ls_shift/su_max          0.0009435
_refine_ls_shift/su_mean         0.0001990


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4737
_refine_ls_R_factor_all          0.0253
_refine_ls_wR_factor_all         0.0677

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4701
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_gt          0.0676

_refine_ls_abs_structure_Flack   0.095(10)
_refine_ls_abs_structure_details 'Flack (1983), 2186 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 6.82 10.9 6.07 2.41 0.570 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.28990(16) 0.33877(10) 0.35043(7) 0.0305 1.0000 Uani . . . . . .
N1 N 0.56040(19) 0.27015(11) 0.23362(8) 0.0183 1.0000 Uani D . . . . .
C1 C 0.5536(2) 0.45154(12) 0.18841(10) 0.0213 1.0000 Uani . . . . . .
C2 C 0.3637(3) 0.49841(14) 0.17360(11) 0.0293 1.0000 Uani . . . . . .
C3 C 0.3285(3) 0.55912(15) 0.09883(13) 0.0380 1.0000 Uani . . . . . .
C4 C 0.4819(4) 0.57443(16) 0.03897(12) 0.0421 1.0000 Uani . . . . . .
C5 C 0.6702(4) 0.52942(16) 0.05310(12) 0.0446 1.0000 Uani . . . . . .
C6 C 0.7064(3) 0.46810(14) 0.12741(12) 0.0327 1.0000 Uani . . . . . .
C7 C 0.5873(2) 0.37834(12) 0.26622(9) 0.0183 1.0000 Uani D . . . . .
C8 C 0.4294(2) 0.39759(13) 0.33877(10) 0.0226 1.0000 Uani . . . . . .
C9 C 0.4656(3) 0.49069(16) 0.39533(12) 0.0332 1.0000 Uani . . . . . .
C10 C 0.6852(3) 0.49165(16) 0.43463(12) 0.0363 1.0000 Uani . . . . . .
C11 C 0.8407(3) 0.48154(16) 0.36166(13) 0.0337 1.0000 Uani . . . . . .
C12 C 0.8035(2) 0.38316(13) 0.31003(11) 0.0237 1.0000 Uani . . . . . .
C13 C 0.3833(2) 0.24728(14) 0.17295(11) 0.0277 1.0000 Uani D . . . . .
H11 H 0.674(2) 0.2545(12) 0.2038(10) 0.0198 1.0000 Uiso D . . . . .
H12 H 0.555(2) 0.2280(11) 0.2810(9) 0.0188 1.0000 Uiso D . . . . .
H21 H 0.2590 0.4873 0.2164 0.0310 1.0000 Uiso R . . . . .
H31 H 0.2003 0.5918 0.0884 0.0354 1.0000 Uiso R . . . . .
H41 H 0.4556 0.6165 -0.0105 0.0434 1.0000 Uiso R . . . . .
H51 H 0.7766 0.5392 0.0100 0.0432 1.0000 Uiso R . . . . .
H61 H 0.8340 0.4342 0.1372 0.0291 1.0000 Uiso R . . . . .
H91 H 0.3665 0.4950 0.4443 0.0361 1.0000 Uiso R . . . . .
H92 H 0.4467 0.5519 0.3566 0.0351 1.0000 Uiso R . . . . .
H101 H 0.7081 0.5568 0.4683 0.0357 1.0000 Uiso R . . . . .
H102 H 0.6963 0.4334 0.4777 0.0351 1.0000 Uiso R . . . . .
H111 H 0.9818 0.4815 0.3876 0.0302 1.0000 Uiso R . . . . .
H112 H 0.8257 0.5387 0.3199 0.0303 1.0000 Uiso R . . . . .
H121 H 0.8145 0.3231 0.3530 0.0190 1.0000 Uiso R . . . . .
H122 H 0.9041 0.3782 0.2630 0.0192 1.0000 Uiso R . . . . .
H131 H 0.3763 0.1732 0.1652 0.0344 1.0000 Uiso R . . . . .
H132 H 0.4012 0.2823 0.1154 0.0340 1.0000 Uiso R . . . . .
H133 H 0.2591 0.2698 0.2006 0.0339 1.0000 Uiso R . . . . .
O21 O 0.55956(15) 0.98751(10) 0.19649(8) 0.0316 1.0000 Uani . . . . . .
N21 N 0.91498(19) 1.04077(10) 0.26615(8) 0.0176 1.0000 Uani D . . . . .
C21 C 0.9337(3) 0.85933(12) 0.30904(10) 0.0228 1.0000 Uani . . . . . .
C22 C 0.7736(3) 0.84539(14) 0.36737(11) 0.0308 1.0000 Uani . . . . . .
C23 C 0.8002(4) 0.78284(16) 0.44191(12) 0.0445 1.0000 Uani . . . . . .
C24 C 0.9872(4) 0.73699(16) 0.45841(13) 0.0492 1.0000 Uani . . . . . .
C25 C 1.1462(4) 0.75039(16) 0.40117(14) 0.0468 1.0000 Uani . . . . . .
C26 C 1.1186(3) 0.81119(15) 0.32633(12) 0.0342 1.0000 Uani . . . . . .
C27 C 0.9029(2) 0.93286(12) 0.23132(9) 0.0170 1.0000 Uani D . . . . .
C28 C 0.6862(2) 0.92064(14) 0.19003(9) 0.0219 1.0000 Uani . . . . . .
C29 C 0.6495(3) 0.82395(15) 0.13863(12) 0.0319 1.0000 Uani . . . . . .
C30 C 0.8076(3) 0.81441(15) 0.06512(11) 0.0318 1.0000 Uani . . . . . .
C31 C 1.0241(3) 0.82196(14) 0.10429(11) 0.0298 1.0000 Uani . . . . . .
C32 C 1.0547(2) 0.92142(13) 0.15517(10) 0.0231 1.0000 Uani . . . . . .
C33 C 1.1062(2) 1.06745(13) 0.31746(11) 0.0262 1.0000 Uani D . . . . .
H211 H 0.896(2) 1.0834(11) 0.2183(9) 0.0190 1.0000 Uiso D . . . . .
H212 H 0.807(2) 1.0528(11) 0.2997(10) 0.0196 1.0000 Uiso D . . . . .
H221 H 0.6481 0.8790 0.3549 0.0331 1.0000 Uiso R . . . . .
H231 H 0.6901 0.7736 0.4832 0.0491 1.0000 Uiso R . . . . .
H241 H 1.0078 0.6955 0.5086 0.0506 1.0000 Uiso R . . . . .
H251 H 1.2702 0.7149 0.4147 0.0502 1.0000 Uiso R . . . . .
H261 H 1.2284 0.8192 0.2855 0.0290 1.0000 Uiso R . . . . .
H291 H 0.5083 0.8211 0.1137 0.0372 1.0000 Uiso R . . . . .
H292 H 0.6683 0.7662 0.1795 0.0373 1.0000 Uiso R . . . . .
H301 H 0.7951 0.7457 0.0353 0.0363 1.0000 Uiso R . . . . .
H302 H 0.7868 0.8682 0.0185 0.0365 1.0000 Uiso R . . . . .
H311 H 1.0431 0.7650 0.1477 0.0292 1.0000 Uiso R . . . . .
H312 H 1.1243 0.8135 0.0567 0.0298 1.0000 Uiso R . . . . .
H321 H 1.1934 0.9214 0.1819 0.0226 1.0000 Uiso R . . . . .
H322 H 1.0344 0.9808 0.1119 0.0221 1.0000 Uiso R . . . . .
H331 H 1.1155 1.0281 0.3731 0.0312 1.0000 Uiso R . . . . .
H332 H 1.2236 1.0537 0.2806 0.0309 1.0000 Uiso R . . . . .
H333 H 1.1072 1.1405 0.3299 0.0316 1.0000 Uiso R . . . . .
Cl1 Cl 0.60404(5) 0.12717(6) 0.39748(2) 0.0238 1.0000 Uani . . . . . .
Cl2 Cl 0.89822(5) 0.19458(5) 0.10920(2) 0.0233 1.0000 Uani . . . . . .

_refine_ls_extinction_coef       259(7)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.3372(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C8 . 1.2090(19) yes
N1 . C7 . 1.5108(19) yes
N1 . C13 . 1.4854(18) yes
N1 . H11 . 0.901(14) no
N1 . H12 . 0.904(14) no
C1 . C2 . 1.396(2) yes
C1 . C6 . 1.389(2) yes
C1 . C7 . 1.527(2) yes
C2 . C3 . 1.394(2) yes
C2 . H21 . 0.962 no
C3 . C4 . 1.378(3) yes
C3 . H31 . 0.949 no
C4 . C5 . 1.375(3) yes
C4 . H41 . 0.940 no
C5 . C6 . 1.394(3) yes
C5 . H51 . 0.970 no
C6 . H61 . 0.952 no
C7 . C8 . 1.541(2) yes
C7 . C12 . 1.5433(19) yes
C8 . C9 . 1.505(2) yes
C9 . C10 . 1.536(2) yes
C9 . H91 . 0.995 no
C9 . H92 . 0.999 no
C10 . C11 . 1.520(3) yes
C10 . H101 . 1.003 no
C10 . H102 . 1.004 no
C11 . C12 . 1.523(2) yes
C11 . H111 . 0.991 no
C11 . H112 . 0.982 no
C12 . H121 . 1.021 no
C12 . H122 . 0.979 no
C13 . H131 . 0.979 no
C13 . H132 . 0.990 no
C13 . H133 . 0.966 no
O21 . C28 . 1.210(2) yes
N21 . C27 . 1.5111(18) yes
N21 . C33 . 1.4925(18) yes
N21 . H211 . 0.918(14) no
N21 . H212 . 0.889(14) no
C21 . C22 . 1.393(2) yes
C21 . C26 . 1.380(2) yes
C21 . C27 . 1.527(2) yes
C22 . C23 . 1.398(3) yes
C22 . H221 . 0.944 no
C23 . C24 . 1.377(3) yes
C23 . H231 . 0.969 no
C24 . C25 . 1.376(4) yes
C24 . H241 . 0.938 no
C25 . C26 . 1.389(3) yes
C25 . H251 . 0.951 no
C26 . H261 . 0.961 no
C27 . C28 . 1.5383(19) yes
C27 . C32 . 1.5411(19) yes
C28 . C29 . 1.502(2) yes
C29 . C30 . 1.536(2) yes
C29 . H291 . 0.986 no
C29 . H292 . 0.982 no
C30 . C31 . 1.520(2) yes
C30 . H301 . 1.009 no
C30 . H302 . 1.002 no
C31 . C32 . 1.524(2) yes
C31 . H311 . 0.998 no
C31 . H312 . 0.988 no
C32 . H321 . 0.981 no
C32 . H322 . 1.023 no
C33 . H331 . 0.985 no
C33 . H332 . 0.974 no
C33 . H333 . 0.977 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . N1 . C13 . 118.17(12) yes
C7 . N1 . H11 . 106.6(10) no
C13 . N1 . H11 . 106.5(9) no
C7 . N1 . H12 . 109.0(9) no
C13 . N1 . H12 . 108.5(9) no
H11 . N1 . H12 . 107.6(12) no
C2 . C1 . C6 . 118.26(15) yes
C2 . C1 . C7 . 120.69(14) yes
C6 . C1 . C7 . 120.92(14) yes
C1 . C2 . C3 . 120.57(16) yes
C1 . C2 . H21 . 117.9 no
C3 . C2 . H21 . 121.6 no
C2 . C3 . C4 . 120.30(17) yes
C2 . C3 . H31 . 121.3 no
C4 . C3 . H31 . 118.4 no
C3 . C4 . C5 . 119.76(17) yes
C3 . C4 . H41 . 118.9 no
C5 . C4 . H41 . 121.3 no
C4 . C5 . C6 . 120.33(19) yes
C4 . C5 . H51 . 119.4 no
C6 . C5 . H51 . 120.3 no
C5 . C6 . C1 . 120.77(18) yes
C5 . C6 . H61 . 121.6 no
C1 . C6 . H61 . 117.6 no
C1 . C7 . N1 . 109.15(11) yes
C1 . C7 . C8 . 110.80(12) yes
N1 . C7 . C8 . 108.07(12) yes
C1 . C7 . C12 . 114.54(12) yes
N1 . C7 . C12 . 105.97(12) yes
C8 . C7 . C12 . 108.04(12) yes
C7 . C8 . O1 . 121.13(14) yes
C7 . C8 . C9 . 115.86(13) yes
O1 . C8 . C9 . 122.96(14) yes
C8 . C9 . C10 . 110.90(14) yes
C8 . C9 . H91 . 111.7 no
C10 . C9 . H91 . 109.3 no
C8 . C9 . H92 . 107.9 no
C10 . C9 . H92 . 108.6 no
H91 . C9 . H92 . 108.4 no
C9 . C10 . C11 . 110.67(14) yes
C9 . C10 . H101 . 109.1 no
C11 . C10 . H101 . 110.3 no
C9 . C10 . H102 . 107.1 no
C11 . C10 . H102 . 111.3 no
H101 . C10 . H102 . 108.3 no
C10 . C11 . C12 . 110.03(15) yes
C10 . C11 . H111 . 110.2 no
C12 . C11 . H111 . 109.6 no
C10 . C11 . H112 . 109.8 no
C12 . C11 . H112 . 108.0 no
H111 . C11 . H112 . 109.3 no
C7 . C12 . C11 . 112.66(13) yes
C7 . C12 . H121 . 106.7 no
C11 . C12 . H121 . 108.8 no
C7 . C12 . H122 . 108.0 no
C11 . C12 . H122 . 108.9 no
H121 . C12 . H122 . 111.7 no
N1 . C13 . H131 . 107.9 no
N1 . C13 . H132 . 109.8 no
H131 . C13 . H132 . 111.2 no
N1 . C13 . H133 . 108.7 no
H131 . C13 . H133 . 108.5 no
H132 . C13 . H133 . 110.7 no
C27 . N21 . C33 . 115.81(12) yes
C27 . N21 . H211 . 107.1(9) no
C33 . N21 . H211 . 111.0(9) no
C27 . N21 . H212 . 109.2(10) no
C33 . N21 . H212 . 109.0(9) no
H211 . N21 . H212 . 104.2(12) no
C22 . C21 . C26 . 119.07(16) yes
C22 . C21 . C27 . 118.68(14) yes
C26 . C21 . C27 . 122.13(15) yes
C21 . C22 . C23 . 120.21(18) yes
C21 . C22 . H221 . 118.2 no
C23 . C22 . H221 . 121.6 no
C22 . C23 . C24 . 119.56(19) yes
C22 . C23 . H231 . 120.7 no
C24 . C23 . H231 . 119.7 no
C23 . C24 . C25 . 120.59(17) yes
C23 . C24 . H241 . 120.5 no
C25 . C24 . H241 . 118.9 no
C24 . C25 . C26 . 119.8(2) yes
C24 . C25 . H251 . 116.9 no
C26 . C25 . H251 . 123.2 no
C25 . C26 . C21 . 120.73(19) yes
C25 . C26 . H261 . 119.9 no
C21 . C26 . H261 . 119.3 no
C21 . C27 . N21 . 108.72(11) yes
C21 . C27 . C28 . 110.27(12) yes
N21 . C27 . C28 . 106.12(12) yes
C21 . C27 . C32 . 115.75(12) yes
N21 . C27 . C32 . 108.70(12) yes
C28 . C27 . C32 . 106.84(11) yes
C27 . C28 . O21 . 120.91(14) yes
C27 . C28 . C29 . 115.43(13) yes
O21 . C28 . C29 . 123.60(14) yes
C28 . C29 . C30 . 109.83(14) yes
C28 . C29 . H291 . 111.3 no
C30 . C29 . H291 . 111.1 no
C28 . C29 . H292 . 108.2 no
C30 . C29 . H292 . 108.2 no
H291 . C29 . H292 . 108.1 no
C29 . C30 . C31 . 110.38(13) yes
C29 . C30 . H301 . 110.2 no
C31 . C30 . H301 . 107.1 no
C29 . C30 . H302 . 111.5 no
C31 . C30 . H302 . 109.5 no
H301 . C30 . H302 . 108.0 no
C30 . C31 . C32 . 111.10(13) yes
C30 . C31 . H311 . 107.7 no
C32 . C31 . H311 . 107.4 no
C30 . C31 . H312 . 109.6 no
C32 . C31 . H312 . 112.3 no
H311 . C31 . H312 . 108.5 no
C27 . C32 . C31 . 112.27(13) yes
C27 . C32 . H321 . 107.3 no
C31 . C32 . H321 . 108.3 no
C27 . C32 . H322 . 109.0 no
C31 . C32 . H322 . 108.6 no
H321 . C32 . H322 . 111.4 no
N21 . C33 . H331 . 110.5 no
N21 . C33 . H332 . 108.7 no
H331 . C33 . H332 . 110.8 no
N21 . C33 . H333 . 109.3 no
H331 . C33 . H333 . 110.6 no
H332 . C33 . H333 . 106.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C32 . H321 . O21 1_655 152.75(4) 0.981 2.545 3.446(3) yes


_chemical_name_systematic        (S)-deschloroketamine
####################################################################### 
# 
# 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_RDCK
_database_code_depnum_ccdc_archive 'CCDC 1838632'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   6.5245(3)
_cell_length_b                   13.1240(5)
_cell_length_c                   15.0650(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.4410(10)
_cell_angle_gamma                90
_cell_volume                     1289.57(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C13 H18 Cl1 N1 O1 
# Dc =      1.23 Fooo =    512.00 Mu =     24.50 M =    479.49
# Found Formula = C13 H18.00 Cl1 N1 O1 
# Dc =      1.23 FOOO =    512.00 Mu =     24.50 M =    479.49

_chemical_formula_sum            'C13 H18 Cl1 N1 O1'
_chemical_formula_moiety         'C13 H18 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         239.74


_cell_measurement_reflns_used    493
_cell_measurement_theta_min      3
_cell_measurement_theta_max      76
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.368
_exptl_crystal_size_mid          0.443
_exptl_crystal_size_max          0.536

_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             511.996
_exptl_absorpt_coefficient_mu    2.450

# Sheldrick geometric approximatio 0.34 0.41 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.30
_exptl_absorpt_correction_T_max  0.41
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            36535
_reflns_number_total             5036
_diffrn_reflns_av_R_equivalents  0.034
# Number of reflections without Friedels Law is 5036 
# Number of reflections with Friedels Law is 2649 
# Theoretical number of reflections is about 2541 


_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         72.121
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        72.121
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              -16
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.08
_oxford_diffrn_Wilson_scale      10.95

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.20


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5036
_refine_ls_number_restraints     15
_refine_ls_number_parameters     303
_oxford_refine_ls_R_factor_ref   0.0266
_refine_ls_wR_factor_ref         0.0698
_refine_ls_goodness_of_fit_ref   0.9997
_refine_ls_shift/su_max          0.0009452
_refine_ls_shift/su_mean         0.0000463


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5036
_refine_ls_R_factor_all          0.0266
_refine_ls_wR_factor_all         0.0698

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4934
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_gt          0.0689

_refine_ls_abs_structure_Flack   0.035(8)
_refine_ls_abs_structure_details 'Flack (1983), 2387 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 7.69 12.6 7.32 3.05 0.720 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.70956(16) 0.49972(10) 0.64962(7) 0.0341 1.0000 Uani . . . . . .
N1 N 0.43905(19) 0.56833(10) 0.76635(8) 0.0207 1.0000 Uani D . . . . .
C1 C 0.4465(2) 0.38679(12) 0.81152(10) 0.0241 1.0000 Uani . . . . . .
C2 C 0.6359(3) 0.34004(14) 0.82648(11) 0.0320 1.0000 Uani . . . . . .
C3 C 0.6714(3) 0.27966(15) 0.90120(13) 0.0406 1.0000 Uani . . . . . .
C4 C 0.5184(3) 0.26423(15) 0.96129(12) 0.0451 1.0000 Uani . . . . . .
C5 C 0.3305(4) 0.30969(16) 0.94685(12) 0.0482 1.0000 Uani . . . . . .
C6 C 0.2937(3) 0.37065(14) 0.87268(12) 0.0361 1.0000 Uani . . . . . .
C7 C 0.4125(2) 0.45992(12) 0.73379(9) 0.0205 1.0000 Uani D . . . . .
C8 C 0.5702(2) 0.44111(12) 0.66119(9) 0.0247 1.0000 Uani . . . . . .
C9 C 0.5337(3) 0.34756(16) 0.60472(11) 0.0353 1.0000 Uani . . . . . .
C10 C 0.3141(3) 0.34672(16) 0.56542(12) 0.0395 1.0000 Uani . . . . . .
C11 C 0.1590(3) 0.35686(16) 0.63850(13) 0.0366 1.0000 Uani . . . . . .
C12 C 0.1962(2) 0.45517(13) 0.68992(10) 0.0261 1.0000 Uani . . . . . .
C13 C 0.6164(2) 0.59103(13) 0.82672(11) 0.0302 1.0000 Uani D . . . . .
H11 H 0.325(2) 0.5841(13) 0.7970(10) 0.0313 1.0000 Uiso D . . . . .
H12 H 0.443(2) 0.6094(11) 0.7195(10) 0.0306 1.0000 Uiso D . . . . .
H21 H 0.7426 0.3517 0.7856 0.0395 1.0000 Uiso R . . . . .
H31 H 0.8031 0.2472 0.9109 0.0508 1.0000 Uiso R . . . . .
H41 H 0.5420 0.2238 1.0133 0.0540 1.0000 Uiso R . . . . .
H51 H 0.2286 0.2993 0.9871 0.0586 1.0000 Uiso R . . . . .
H61 H 0.1652 0.4024 0.8648 0.0430 1.0000 Uiso R . . . . .
H91 H 0.6325 0.3454 0.5592 0.0437 1.0000 Uiso R . . . . .
H92 H 0.5497 0.2877 0.6422 0.0431 1.0000 Uiso R . . . . .
H101 H 0.2916 0.2826 0.5336 0.0481 1.0000 Uiso R . . . . .
H102 H 0.3010 0.4026 0.5232 0.0463 1.0000 Uiso R . . . . .
H111 H 0.0213 0.3620 0.6122 0.0446 1.0000 Uiso R . . . . .
H112 H 0.1660 0.2988 0.6781 0.0432 1.0000 Uiso R . . . . .
H121 H 0.1864 0.5116 0.6506 0.0316 1.0000 Uiso R . . . . .
H122 H 0.0951 0.4658 0.7340 0.0299 1.0000 Uiso R . . . . .
H131 H 0.6199 0.6641 0.8343 0.0448 1.0000 Uiso R . . . . .
H132 H 0.5925 0.5570 0.8809 0.0437 1.0000 Uiso R . . . . .
H133 H 0.7423 0.5667 0.8015 0.0447 1.0000 Uiso R . . . . .
O21 O 0.44055(15) -0.14861(10) 0.80357(7) 0.0338 1.0000 Uani . . . . . .
N21 N 0.08534(18) -0.20182(10) 0.73389(8) 0.0197 1.0000 Uani D . . . . .
C21 C 0.0663(2) -0.02080(12) 0.69109(10) 0.0250 1.0000 Uani . . . . . .
C22 C 0.2259(3) -0.00693(14) 0.63252(11) 0.0331 1.0000 Uani . . . . . .
C23 C 0.1992(4) 0.05553(16) 0.55805(12) 0.0472 1.0000 Uani . . . . . .
C24 C 0.0130(4) 0.10159(16) 0.54162(12) 0.0527 1.0000 Uani . . . . . .
C25 C -0.1458(4) 0.08808(16) 0.59870(14) 0.0502 1.0000 Uani . . . . . .
C26 C -0.1187(3) 0.02727(14) 0.67382(12) 0.0370 1.0000 Uani . . . . . .
C27 C 0.0978(2) -0.09441(12) 0.76879(9) 0.0192 1.0000 Uani D . . . . .
C28 C 0.3141(2) -0.08182(13) 0.81008(9) 0.0243 1.0000 Uani . . . . . .
C29 C 0.3502(2) 0.01485(15) 0.86132(12) 0.0348 1.0000 Uani . . . . . .
C30 C 0.1922(3) 0.02432(15) 0.93500(11) 0.0356 1.0000 Uani . . . . . .
C31 C -0.0236(3) 0.01656(14) 0.89578(11) 0.0330 1.0000 Uani . . . . . .
C32 C -0.0542(2) -0.08276(13) 0.84482(9) 0.0254 1.0000 Uani . . . . . .
C33 C -0.1060(2) -0.22891(13) 0.68273(10) 0.0290 1.0000 Uani D . . . . .
H211 H 0.101(2) -0.2440(11) 0.7805(10) 0.0296 1.0000 Uiso D . . . . .
H212 H 0.194(2) -0.2154(12) 0.6990(10) 0.0296 1.0000 Uiso D . . . . .
H221 H 0.3518 -0.0407 0.6439 0.0396 1.0000 Uiso R . . . . .
H231 H 0.3126 0.0665 0.5202 0.0571 1.0000 Uiso R . . . . .
H241 H -0.0052 0.1425 0.4921 0.0633 1.0000 Uiso R . . . . .
H251 H -0.2737 0.1201 0.5877 0.0605 1.0000 Uiso R . . . . .
H261 H -0.2282 0.0184 0.7121 0.0451 1.0000 Uiso R . . . . .
H291 H 0.4888 0.0169 0.8857 0.0432 1.0000 Uiso R . . . . .
H292 H 0.3309 0.0720 0.8205 0.0434 1.0000 Uiso R . . . . .
H301 H 0.2050 0.0903 0.9631 0.0421 1.0000 Uiso R . . . . .
H302 H 0.2134 -0.0299 0.9797 0.0425 1.0000 Uiso R . . . . .
H311 H -0.0521 0.0735 0.8566 0.0403 1.0000 Uiso R . . . . .
H312 H -0.1216 0.0240 0.9430 0.0391 1.0000 Uiso R . . . . .
H321 H -0.1924 -0.0868 0.8214 0.0312 1.0000 Uiso R . . . . .
H322 H -0.0326 -0.1393 0.8861 0.0313 1.0000 Uiso R . . . . .
H331 H -0.1056 -0.1923 0.6263 0.0432 1.0000 Uiso R . . . . .
H332 H -0.2243 -0.2111 0.7173 0.0428 1.0000 Uiso R . . . . .
H333 H -0.1014 -0.2985 0.6715 0.0435 1.0000 Uiso R . . . . .
Cl1 Cl 0.39608(5) 0.71147(5) 0.602645(19) 0.0263 1.0000 Uani . . . . . .
Cl2 Cl 0.10169(5) 0.64412(5) 0.89068(2) 0.0261 1.0000 Uani . . . . . .

_refine_ls_extinction_coef       212(7)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.3095(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C8 . 1.2070(19) yes
N1 . C7 . 1.5135(19) yes
N1 . C13 . 1.4838(18) yes
N1 . H11 . 0.910(14) no
N1 . H12 . 0.889(14) no
C1 . C2 . 1.393(2) yes
C1 . C6 . 1.391(2) yes
C1 . C7 . 1.526(2) yes
C2 . C3 . 1.391(2) yes
C2 . H21 . 0.953 no
C3 . C4 . 1.379(3) yes
C3 . H31 . 0.967 no
C4 . C5 . 1.375(3) yes
C4 . H41 . 0.956 no
C5 . C6 . 1.390(3) yes
C5 . H51 . 0.921 no
C6 . H61 . 0.941 no
C7 . C8 . 1.540(2) yes
C7 . C12 . 1.5443(19) yes
C8 . C9 . 1.509(2) yes
C9 . C10 . 1.537(2) yes
C9 . H91 . 0.954 no
C9 . H92 . 0.972 no
C10 . C11 . 1.520(3) yes
C10 . H101 . 0.978 no
C10 . H102 . 0.974 no
C11 . C12 . 1.521(2) yes
C11 . H111 . 0.975 no
C11 . H112 . 0.968 no
C12 . H121 . 0.949 no
C12 . H122 . 0.958 no
C13 . H131 . 0.966 no
C13 . H132 . 0.947 no
C13 . H133 . 0.968 no
O21 . C28 . 1.209(2) yes
N21 . C27 . 1.5060(18) yes
N21 . C33 . 1.4933(18) yes
N21 . H211 . 0.898(14) no
N21 . H212 . 0.910(14) no
C21 . C22 . 1.394(2) yes
C21 . C26 . 1.381(2) yes
C21 . C27 . 1.528(2) yes
C22 . C23 . 1.397(2) yes
C22 . H221 . 0.945 no
C23 . C24 . 1.374(3) yes
C23 . H231 . 0.956 no
C24 . C25 . 1.375(4) yes
C24 . H241 . 0.925 no
C25 . C26 . 1.392(3) yes
C25 . H251 . 0.945 no
C26 . H261 . 0.937 no
C27 . C28 . 1.5369(18) yes
C27 . C32 . 1.5416(19) yes
C28 . C29 . 1.501(2) yes
C29 . C30 . 1.539(2) yes
C29 . H291 . 0.968 no
C29 . H292 . 0.977 no
C30 . C31 . 1.516(2) yes
C30 . H301 . 0.967 no
C30 . H302 . 0.987 no
C31 . C32 . 1.523(2) yes
C31 . H311 . 0.968 no
C31 . H312 . 0.973 no
C32 . H321 . 0.961 no
C32 . H322 . 0.977 no
C33 . H331 . 0.977 no
C33 . H332 . 0.970 no
C33 . H333 . 0.929 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . N1 . C13 . 117.95(12) yes
C7 . N1 . H11 . 106.8(10) no
C13 . N1 . H11 . 106.2(10) no
C7 . N1 . H12 . 108.6(10) no
C13 . N1 . H12 . 109.0(10) no
H11 . N1 . H12 . 107.9(12) no
C2 . C1 . C6 . 118.28(15) yes
C2 . C1 . C7 . 120.82(13) yes
C6 . C1 . C7 . 120.75(14) yes
C1 . C2 . C3 . 120.71(16) yes
C1 . C2 . H21 . 119.0 no
C3 . C2 . H21 . 120.3 no
C2 . C3 . C4 . 120.40(17) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 119.4 no
C3 . C4 . C5 . 119.29(16) yes
C3 . C4 . H41 . 121.0 no
C5 . C4 . H41 . 119.7 no
C4 . C5 . C6 . 120.81(18) yes
C4 . C5 . H51 . 119.1 no
C6 . C5 . H51 . 120.1 no
C1 . C6 . C5 . 120.51(18) yes
C1 . C6 . H61 . 120.0 no
C5 . C6 . H61 . 119.4 no
C1 . C7 . N1 . 109.22(11) yes
C1 . C7 . C8 . 110.93(12) yes
N1 . C7 . C8 . 107.92(12) yes
C1 . C7 . C12 . 114.63(12) yes
N1 . C7 . C12 . 105.83(11) yes
C8 . C7 . C12 . 108.01(12) yes
C7 . C8 . O1 . 121.30(13) yes
C7 . C8 . C9 . 115.59(13) yes
O1 . C8 . C9 . 123.07(14) yes
C8 . C9 . C10 . 110.81(14) yes
C8 . C9 . H91 . 109.2 no
C10 . C9 . H91 . 111.3 no
C8 . C9 . H92 . 108.5 no
C10 . C9 . H92 . 107.7 no
H91 . C9 . H92 . 109.3 no
C9 . C10 . C11 . 110.58(14) yes
C9 . C10 . H101 . 108.8 no
C11 . C10 . H101 . 109.6 no
C9 . C10 . H102 . 108.2 no
C11 . C10 . H102 . 111.0 no
H101 . C10 . H102 . 108.6 no
C10 . C11 . C12 . 110.04(15) yes
C10 . C11 . H111 . 109.6 no
C12 . C11 . H111 . 106.3 no
C10 . C11 . H112 . 110.8 no
C12 . C11 . H112 . 110.4 no
H111 . C11 . H112 . 109.5 no
C7 . C12 . C11 . 112.61(13) yes
C7 . C12 . H121 . 106.4 no
C11 . C12 . H121 . 109.7 no
C7 . C12 . H122 . 109.6 no
C11 . C12 . H122 . 111.9 no
H121 . C12 . H122 . 106.4 no
N1 . C13 . H131 . 106.7 no
N1 . C13 . H132 . 106.9 no
H131 . C13 . H132 . 111.8 no
N1 . C13 . H133 . 110.5 no
H131 . C13 . H133 . 110.9 no
H132 . C13 . H133 . 110.0 no
C27 . N21 . C33 . 116.11(12) yes
C27 . N21 . H211 . 107.4(10) no
C33 . N21 . H211 . 109.4(9) no
C27 . N21 . H212 . 110.4(10) no
C33 . N21 . H212 . 107.9(10) no
H211 . N21 . H212 . 104.9(12) no
C22 . C21 . C26 . 118.98(15) yes
C22 . C21 . C27 . 118.67(14) yes
C26 . C21 . C27 . 122.22(14) yes
C21 . C22 . C23 . 120.34(18) yes
C21 . C22 . H221 . 118.9 no
C23 . C22 . H221 . 120.8 no
C22 . C23 . C24 . 119.65(19) yes
C22 . C23 . H231 . 119.0 no
C24 . C23 . H231 . 121.4 no
C23 . C24 . C25 . 120.51(17) yes
C23 . C24 . H241 . 119.7 no
C25 . C24 . H241 . 119.8 no
C24 . C25 . C26 . 120.0(2) yes
C24 . C25 . H251 . 120.6 no
C26 . C25 . H251 . 119.4 no
C25 . C26 . C21 . 120.50(18) yes
C25 . C26 . H261 . 119.3 no
C21 . C26 . H261 . 120.2 no
C21 . C27 . N21 . 108.63(11) yes
C21 . C27 . C28 . 110.27(12) yes
N21 . C27 . C28 . 106.43(11) yes
C21 . C27 . C32 . 115.47(12) yes
N21 . C27 . C32 . 108.79(12) yes
C28 . C27 . C32 . 106.87(11) yes
C27 . C28 . O21 . 120.70(14) yes
C27 . C28 . C29 . 115.45(13) yes
O21 . C28 . C29 . 123.78(14) yes
C28 . C29 . C30 . 109.87(14) yes
C28 . C29 . H291 . 110.7 no
C30 . C29 . H291 . 111.1 no
C28 . C29 . H292 . 108.0 no
C30 . C29 . H292 . 108.3 no
H291 . C29 . H292 . 108.8 no
C29 . C30 . C31 . 110.24(13) yes
C29 . C30 . H301 . 109.6 no
C31 . C30 . H301 . 107.5 no
C29 . C30 . H302 . 110.4 no
C31 . C30 . H302 . 109.3 no
H301 . C30 . H302 . 109.8 no
C30 . C31 . C32 . 111.26(13) yes
C30 . C31 . H311 . 110.4 no
C32 . C31 . H311 . 109.4 no
C30 . C31 . H312 . 109.2 no
C32 . C31 . H312 . 112.0 no
H311 . C31 . H312 . 104.4 no
C27 . C32 . C31 . 112.37(13) yes
C27 . C32 . H321 . 109.7 no
C31 . C32 . H321 . 110.0 no
C27 . C32 . H322 . 108.2 no
C31 . C32 . H322 . 108.3 no
H321 . C32 . H322 . 108.2 no
N21 . C33 . H331 . 108.2 no
N21 . C33 . H332 . 109.4 no
H331 . C33 . H332 . 111.6 no
N21 . C33 . H333 . 107.3 no
H331 . C33 . H333 . 108.9 no
H332 . C33 . H333 . 111.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C32 . H321 . O21 1_455 158.52(4) 0.961 2.536 3.449(3) yes


_chemical_name_systematic        (R)-deschloroketamine
