# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_II_100K
_oxford_structure_analysis_title '100K in P2(1)/c'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone Hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'


#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 

# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 


_cell_length_a                   9.9973(13)
_cell_length_b                   22.788(3)
_cell_length_c                   10.4078(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.2430(10)
_cell_angle_gamma                90
_cell_volume                     2370.5(5)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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            8

# Given Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.20 Fooo =    912.00 Mu =      2.92 M =    427.41
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.20 FOOO =    912.00 Mu =      2.92 M =    427.41

_chemical_formula_sum            'C11 H16 Cl1 N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    3387
_cell_measurement_theta_min      4
_cell_measurement_theta_max      26
_cell_measurement_temperature    100

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.292

# Sheldrick geometric approximatio 0.94 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# 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      100
_diffrn_reflns_number            15326
_reflns_number_total             4706
_diffrn_reflns_av_R_equivalents  0.038
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4706 
# Theoretical number of reflections is about 9715 


_diffrn_reflns_theta_min         3.369
_diffrn_reflns_theta_max         26.390
_diffrn_measured_fraction_theta_max 0.969

_diffrn_reflns_theta_full        25.071
_diffrn_measured_fraction_theta_full 0.974


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.13
_oxford_diffrn_Wilson_scale      100.45

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

_refine_diff_density_min         -0.48
_refine_diff_density_max         0.52


# 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>-10.0\s(I)
_refine_ls_number_reflns         4702
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0649
_refine_ls_wR_factor_ref         0.0872
_refine_ls_goodness_of_fit_ref   1.0075
_refine_ls_shift/su_max          0.0006751
_refine_ls_shift/su_mean         0.0000293


# The values computed from all data 
_oxford_reflns_number_all        4702
_refine_ls_R_factor_all          0.0649
_refine_ls_wR_factor_all         0.0872

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3354
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_gt          0.0732

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 1.56P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5983(2) -0.07252(9) 0.4261(2) 0.0368 1.0000 Uani . . . . . .
C2 C 0.6700(2) -0.01813(9) 0.4730(2) 0.0280 1.0000 Uani . . . . . .
C3 C 0.7269(2) -0.01585(9) 0.5954(2) 0.0310 1.0000 Uani . . . . . .
C4 C 0.7944(2) 0.03376(9) 0.6385(2) 0.0293 1.0000 Uani . . . . . .
C5 C 0.80747(19) 0.08255(8) 0.5582(2) 0.0229 1.0000 Uani . . . . . .
C6 C 0.74915(19) 0.08092(9) 0.4358(2) 0.0240 1.0000 Uani . . . . . .
C7 C 0.6801(2) 0.03115(9) 0.3941(2) 0.0262 1.0000 Uani . . . . . .
C8 C 0.8842(2) 0.13409(8) 0.6079(2) 0.0224 1.0000 Uani . . . . . .
O9 O 0.90776(16) 0.14130(6) 0.72233(14) 0.0334 1.0000 Uani . . . . . .
C10 C 0.94075(19) 0.17708(8) 0.51080(19) 0.0206 1.0000 Uani . . . . . .
C11 C 1.0637(2) 0.14998(9) 0.4486(2) 0.0303 1.0000 Uani . . . . . .
N12 N 0.97731(16) 0.23255(6) 0.57795(15) 0.0199 1.0000 Uani . . . . . .
C13 C 1.0019(2) 0.28274(8) 0.4899(2) 0.0253 1.0000 Uani . . . . . .
C14 C 0.0536(2) 0.55884(9) 0.3450(2) 0.0337 1.0000 Uani . . . . . .
C15 C 0.1446(2) 0.51183(9) 0.3981(2) 0.0264 1.0000 Uani . . . . . .
C16 C 0.2290(2) 0.52352(9) 0.5027(2) 0.0316 1.0000 Uani . . . . . .
C17 C 0.3132(2) 0.48089(9) 0.5541(2) 0.0313 1.0000 Uani . . . . . .
C18 C 0.3153(2) 0.42462(9) 0.5007(2) 0.0252 1.0000 Uani . . . . . .
C19 C 0.23175(19) 0.41267(9) 0.39529(19) 0.0241 1.0000 Uani . . . . . .
C20 C 0.1475(2) 0.45586(9) 0.3452(2) 0.0259 1.0000 Uani . . . . . .
C21 C 0.4030(2) 0.37910(9) 0.5620(2) 0.0257 1.0000 Uani . . . . . .
O22 O 0.44599(16) 0.38439(7) 0.67182(16) 0.0410 1.0000 Uani . . . . . .
C23 C 0.44332(19) 0.32645(8) 0.48187(19) 0.0227 1.0000 Uani . . . . . .
C24 C 0.5559(2) 0.34334(9) 0.3925(2) 0.0324 1.0000 Uani . . . . . .
N25 N 0.48582(16) 0.27858(7) 0.57060(16) 0.0215 1.0000 Uani . . . . . .
C26 C 0.5171(2) 0.22218(8) 0.5052(2) 0.0264 1.0000 Uani . . . . . .
Cl1 Cl 0.74975(5) 0.28796(2) 0.72776(5) 0.0241 1.0000 Uani . . . . . .
Cl2 Cl 0.24898(5) 0.26335(2) 0.22947(5) 0.0250 1.0000 Uani . . . . . .
H13 H 0.5241 -0.0616 0.3731 0.0662 1.0000 Uiso R . . . . .
H11 H 0.6579 -0.0964 0.3788 0.0652 1.0000 Uiso R . . . . .
H12 H 0.5663 -0.0951 0.4966 0.0663 1.0000 Uiso R . . . . .
H31 H 0.7189 -0.0483 0.6502 0.0453 1.0000 Uiso R . . . . .
H41 H 0.8338 0.0336 0.7231 0.0399 1.0000 Uiso R . . . . .
H61 H 0.7550 0.1141 0.3820 0.0332 1.0000 Uiso R . . . . .
H71 H 0.6375 0.0320 0.3121 0.0369 1.0000 Uiso R . . . . .
H101 H 0.8739 0.1875 0.4457 0.0275 1.0000 Uiso R . . . . .
H113 H 1.0958 0.1759 0.3842 0.0505 1.0000 Uiso R . . . . .
H111 H 1.1335 0.1445 0.5137 0.0509 1.0000 Uiso R . . . . .
H112 H 1.0408 0.1131 0.4129 0.0510 1.0000 Uiso R . . . . .
H131 H 1.0253 0.3159 0.5438 0.0444 1.0000 Uiso R . . . . .
H133 H 1.0760 0.2741 0.4353 0.0445 1.0000 Uiso R . . . . .
H132 H 0.9232 0.2901 0.4379 0.0451 1.0000 Uiso R . . . . .
H142 H 0.0127 0.5462 0.2636 0.0607 1.0000 Uiso R . . . . .
H141 H 0.1057 0.5939 0.3327 0.0600 1.0000 Uiso R . . . . .
H143 H -0.0153 0.5679 0.4054 0.0595 1.0000 Uiso R . . . . .
H161 H 0.2273 0.5610 0.5407 0.0453 1.0000 Uiso R . . . . .
H171 H 0.3676 0.4887 0.6294 0.0446 1.0000 Uiso R . . . . .
H191 H 0.2329 0.3752 0.3566 0.0340 1.0000 Uiso R . . . . .
H201 H 0.0916 0.4469 0.2739 0.0352 1.0000 Uiso R . . . . .
H231 H 0.3694 0.3127 0.4314 0.0303 1.0000 Uiso R . . . . .
H242 H 0.5762 0.3116 0.3345 0.0558 1.0000 Uiso R . . . . .
H241 H 0.6341 0.3514 0.4463 0.0550 1.0000 Uiso R . . . . .
H243 H 0.5292 0.3773 0.3444 0.0559 1.0000 Uiso R . . . . .
H262 H 0.5382 0.1927 0.5709 0.0457 1.0000 Uiso R . . . . .
H263 H 0.5945 0.2272 0.4528 0.0462 1.0000 Uiso R . . . . .
H261 H 0.4411 0.2107 0.4511 0.0464 1.0000 Uiso R . . . . .
H121 H 1.0523 0.2258 0.6294 0.0346 1.0000 Uiso R . . . . .
H122 H 0.9106 0.2440 0.6344 0.0353 1.0000 Uiso R . . . . .
H252 H 0.4181 0.2701 0.6269 0.0366 1.0000 Uiso R . . . . .
H251 H 0.5601 0.2898 0.6175 0.0366 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0335(13) 0.0281(12) 0.0490(16) -0.0098(11) 0.0094(11) -0.0074(9)
C2 0.0219(10) 0.0231(11) 0.0395(14) -0.0055(9) 0.0077(10) -0.0001(8)
C3 0.0307(11) 0.0221(11) 0.0403(15) 0.0053(9) 0.0032(10) 0.0004(9)
C4 0.0300(11) 0.0269(11) 0.0310(13) 0.0044(10) -0.0003(10) -0.0012(9)
C5 0.0248(10) 0.0212(10) 0.0227(11) -0.0006(8) 0.0023(9) -0.0005(8)
C6 0.0229(10) 0.0233(10) 0.0261(12) -0.0004(9) 0.0049(9) -0.0003(8)
C7 0.0225(10) 0.0301(11) 0.0262(12) -0.0065(9) 0.0020(9) -0.0015(8)
C8 0.0229(10) 0.0222(10) 0.0219(12) 0.0013(8) -0.0017(9) 0.0034(8)
O9 0.0468(10) 0.0316(9) 0.0216(9) 0.0039(7) -0.0063(7) -0.0062(7)
C10 0.0219(10) 0.0203(10) 0.0197(11) -0.0022(8) -0.0009(8) -0.0006(8)
C11 0.0305(12) 0.0252(11) 0.0355(13) -0.0097(9) 0.0081(10) -0.0007(9)
N12 0.0198(8) 0.0212(8) 0.0188(9) 0.0007(7) 0.0018(7) 0.0001(6)
C13 0.0302(11) 0.0195(11) 0.0264(12) 0.0028(9) 0.0059(9) 0.0004(8)
C14 0.0369(13) 0.0238(11) 0.0406(14) 0.0039(10) 0.0093(11) 0.0046(9)
C15 0.0270(11) 0.0243(11) 0.0282(13) 0.0048(9) 0.0092(10) -0.0007(9)
C16 0.0348(12) 0.0187(11) 0.0414(14) -0.0043(9) 0.0055(11) -0.0013(9)
C17 0.0331(12) 0.0277(12) 0.0331(13) -0.0068(10) -0.0023(10) -0.0021(9)
C18 0.0228(10) 0.0250(11) 0.0281(12) -0.0016(9) 0.0043(9) -0.0006(8)
C19 0.0273(11) 0.0215(10) 0.0237(11) -0.0036(8) 0.0027(9) 0.0003(8)
C20 0.0256(11) 0.0260(11) 0.0262(12) 0.0009(9) 0.0015(9) 0.0009(8)
C21 0.0239(11) 0.0273(11) 0.0259(12) -0.0067(9) 0.0001(9) -0.0016(8)
O22 0.0484(10) 0.0431(10) 0.0308(10) -0.0127(7) -0.0133(8) 0.0131(8)
C23 0.0221(10) 0.0239(10) 0.0220(11) -0.0004(8) -0.0013(8) -0.0001(8)
C24 0.0365(13) 0.0289(12) 0.0322(13) 0.0060(10) 0.0096(10) 0.0013(9)
N25 0.0178(8) 0.0247(9) 0.0221(9) 0.0003(7) 0.0014(7) -0.0013(6)
C26 0.0325(12) 0.0208(11) 0.0259(12) -0.0029(8) 0.0011(9) 0.0018(8)
Cl1 0.0174(2) 0.0356(3) 0.0194(3) -0.0058(2) -0.00034(19) 0.0014(2)
Cl2 0.0180(2) 0.0372(3) 0.0198(3) -0.0052(2) 0.00000(19) 0.0026(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.10310(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
C1 . C2 . 1.507(3) yes
C1 . H13 . 0.948 no
C1 . H11 . 0.951 no
C1 . H12 . 0.957 no
C2 . C3 . 1.385(3) yes
C2 . C7 . 1.397(3) yes
C3 . C4 . 1.386(3) yes
C3 . H31 . 0.938 no
C4 . C5 . 1.398(3) yes
C4 . H41 . 0.957 no
C5 . C6 . 1.390(3) yes
C5 . C8 . 1.489(3) yes
C6 . C7 . 1.392(3) yes
C6 . H61 . 0.943 no
C7 . H71 . 0.945 no
C8 . O9 . 1.220(2) yes
C8 . C10 . 1.525(3) yes
C10 . C11 . 1.531(3) yes
C10 . N12 . 1.486(2) yes
C10 . H101 . 0.971 no
C11 . H113 . 0.954 no
C11 . H111 . 0.970 no
C11 . H112 . 0.945 no
N12 . C13 . 1.489(2) yes
N12 . H121 . 0.925 no
N12 . H122 . 0.935 no
C13 . H131 . 0.967 no
C13 . H133 . 0.964 no
C13 . H132 . 0.960 no
C14 . C15 . 1.504(3) yes
C14 . H142 . 0.976 no
C14 . H141 . 0.963 no
C14 . H143 . 0.965 no
C15 . C16 . 1.388(3) yes
C15 . C20 . 1.390(3) yes
C16 . C17 . 1.385(3) yes
C16 . H161 . 0.941 no
C17 . C18 . 1.398(3) yes
C17 . H171 . 0.961 no
C18 . C19 . 1.391(3) yes
C18 . C21 . 1.493(3) yes
C19 . C20 . 1.389(3) yes
C19 . H191 . 0.944 no
C20 . H201 . 0.942 no
C21 . O22 . 1.218(3) yes
C21 . C23 . 1.521(3) yes
C23 . C24 . 1.525(3) yes
C23 . N25 . 1.485(2) yes
C23 . H231 . 0.950 no
C24 . H242 . 0.967 no
C24 . H241 . 0.969 no
C24 . H243 . 0.957 no
N25 . C26 . 1.491(2) yes
N25 . H252 . 0.925 no
N25 . H251 . 0.916 no
C26 . H262 . 0.978 no
C26 . H263 . 0.963 no
C26 . H261 . 0.971 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
C2 . C1 . H13 . 109.5 no
C2 . C1 . H11 . 109.8 no
H13 . C1 . H11 . 109.8 no
C2 . C1 . H12 . 111.1 no
H13 . C1 . H12 . 108.5 no
H11 . C1 . H12 . 108.2 no
C1 . C2 . C3 . 120.8(2) yes
C1 . C2 . C7 . 120.7(2) yes
C3 . C2 . C7 . 118.52(19) yes
C2 . C3 . C4 . 121.0(2) yes
C2 . C3 . H31 . 119.4 no
C4 . C3 . H31 . 119.6 no
C3 . C4 . C5 . 120.4(2) yes
C3 . C4 . H41 . 118.9 no
C5 . C4 . H41 . 120.7 no
C4 . C5 . C6 . 118.91(19) yes
C4 . C5 . C8 . 118.27(19) yes
C6 . C5 . C8 . 122.81(18) yes
C5 . C6 . C7 . 120.17(19) yes
C5 . C6 . H61 . 119.5 no
C7 . C6 . H61 . 120.3 no
C2 . C7 . C6 . 120.9(2) yes
C2 . C7 . H71 . 120.7 no
C6 . C7 . H71 . 118.3 no
C5 . C8 . O9 . 122.16(18) yes
C5 . C8 . C10 . 118.16(17) yes
O9 . C8 . C10 . 119.59(18) yes
C8 . C10 . C11 . 109.49(16) yes
C8 . C10 . N12 . 109.00(15) yes
C11 . C10 . N12 . 110.52(15) yes
C8 . C10 . H101 . 111.1 no
C11 . C10 . H101 . 110.5 no
N12 . C10 . H101 . 106.2 no
C10 . C11 . H113 . 109.5 no
C10 . C11 . H111 . 109.2 no
H113 . C11 . H111 . 108.8 no
C10 . C11 . H112 . 109.6 no
H113 . C11 . H112 . 110.9 no
H111 . C11 . H112 . 108.9 no
C10 . N12 . C13 . 113.96(16) yes
C10 . N12 . H121 . 108.6 no
C13 . N12 . H121 . 109.9 no
C10 . N12 . H122 . 111.2 no
C13 . N12 . H122 . 107.6 no
H121 . N12 . H122 . 105.2 no
N12 . C13 . H131 . 106.5 no
N12 . C13 . H133 . 110.2 no
H131 . C13 . H133 . 108.8 no
N12 . C13 . H132 . 109.7 no
H131 . C13 . H132 . 112.0 no
H133 . C13 . H132 . 109.5 no
C15 . C14 . H142 . 110.4 no
C15 . C14 . H141 . 108.3 no
H142 . C14 . H141 . 110.3 no
C15 . C14 . H143 . 110.3 no
H142 . C14 . H143 . 109.7 no
H141 . C14 . H143 . 107.7 no
C14 . C15 . C16 . 120.30(19) yes
C14 . C15 . C20 . 121.7(2) yes
C16 . C15 . C20 . 118.0(2) yes
C15 . C16 . C17 . 121.5(2) yes
C15 . C16 . H161 . 119.2 no
C17 . C16 . H161 . 119.3 no
C16 . C17 . C18 . 120.2(2) yes
C16 . C17 . H171 . 120.9 no
C18 . C17 . H171 . 118.8 no
C17 . C18 . C19 . 118.7(2) yes
C17 . C18 . C21 . 118.7(2) yes
C19 . C18 . C21 . 122.57(18) yes
C18 . C19 . C20 . 120.37(19) yes
C18 . C19 . H191 . 120.0 no
C20 . C19 . H191 . 119.6 no
C15 . C20 . C19 . 121.3(2) yes
C15 . C20 . H201 . 119.6 no
C19 . C20 . H201 . 119.1 no
C18 . C21 . O22 . 121.63(18) yes
C18 . C21 . C23 . 118.27(18) yes
O22 . C21 . C23 . 120.04(19) yes
C21 . C23 . C24 . 110.09(16) yes
C21 . C23 . N25 . 108.29(16) yes
C24 . C23 . N25 . 111.07(16) yes
C21 . C23 . H231 . 110.6 no
C24 . C23 . H231 . 108.8 no
N25 . C23 . H231 . 108.0 no
C23 . C24 . H242 . 111.1 no
C23 . C24 . H241 . 107.0 no
H242 . C24 . H241 . 109.0 no
C23 . C24 . H243 . 108.8 no
H242 . C24 . H243 . 109.8 no
H241 . C24 . H243 . 111.2 no
C23 . N25 . C26 . 114.15(16) yes
C23 . N25 . H252 . 110.1 no
C26 . N25 . H252 . 105.9 no
C23 . N25 . H251 . 110.1 no
C26 . N25 . H251 . 107.9 no
H252 . N25 . H251 . 108.4 no
N25 . C26 . H262 . 108.4 no
N25 . C26 . H263 . 109.5 no
H262 . C26 . H263 . 108.3 no
N25 . C26 . H261 . 109.2 no
H262 . C26 . H261 . 112.0 no
H263 . C26 . H261 . 109.4 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/09/11 at 10:17:19
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE N   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 263,X'S) H   ( 261,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/09/11 at 10:17:19
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983740'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_II_123K
_oxford_structure_analysis_title 'mebrII_0m in P2(1)/c'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone Hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'

#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 




# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 





_cell_length_a                   10.0093(3)
_cell_length_b                   22.8207(8)
_cell_length_c                   10.4016(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.416(2)
_cell_angle_gamma                90
_cell_volume                     2375.20(14)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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            8

# Given Formula = C11 H14 Cl1 N1 O1 
# Dc =      1.18 Fooo =    912.00 Mu =      2.91 M =    423.38
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.20 FOOO =    912.00 Mu =      2.92 M =    427.41

_chemical_formula_sum            'C11 H16 Cl N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    5197
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.50

_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.292

# Sheldrick geometric approximatio 0.97 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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      123
_diffrn_reflns_number            26575
_reflns_number_total             4513
_diffrn_reflns_av_R_equivalents  0.046
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4513 
# Theoretical number of reflections is about 9050 


_diffrn_reflns_theta_min         1.785
_diffrn_reflns_theta_max         25.710
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        25.710
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   2.13
_oxford_diffrn_Wilson_scale      100.45

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

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.39


# 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>-10.0\s(I)
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0625
_refine_ls_wR_factor_ref         0.1000
_refine_ls_goodness_of_fit_ref   1.0990
_refine_ls_shift/su_max          0.0003626
_refine_ls_shift/su_mean         0.0000215


# The values computed from all data 
_oxford_reflns_number_all        4494
_refine_ls_R_factor_all          0.0625
_refine_ls_wR_factor_all         0.1000

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3110
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_gt          0.0806

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 1.67P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5972(3) -0.07111(11) 0.4210(3) 0.0440 1.0000 Uani . . . . . .
C2 C 0.6699(2) -0.01713(11) 0.4686(2) 0.0330 1.0000 Uani . . . . . .
C3 C 0.7291(3) -0.01584(11) 0.5903(3) 0.0374 1.0000 Uani . . . . . .
C4 C 0.7972(2) 0.03319(10) 0.6345(2) 0.0338 1.0000 Uani . . . . . .
C5 C 0.8089(2) 0.08238(10) 0.5562(2) 0.0260 1.0000 Uani . . . . . .
C6 C 0.7481(2) 0.08181(10) 0.4339(2) 0.0283 1.0000 Uani . . . . . .
C7 C 0.6793(2) 0.03242(10) 0.3917(2) 0.0319 1.0000 Uani . . . . . .
C8 C 0.8859(2) 0.13375(10) 0.6061(2) 0.0260 1.0000 Uani . . . . . .
O9 O 0.91099(18) 0.14013(7) 0.72114(15) 0.0394 1.0000 Uani . . . . . .
C10 C 0.9411(2) 0.17708(9) 0.5105(2) 0.0232 1.0000 Uani . . . . . .
C11 C 1.0625(2) 0.15049(10) 0.4460(2) 0.0344 1.0000 Uani . . . . . .
N12 N 0.97835(18) 0.23227(7) 0.57857(17) 0.0233 1.0000 Uani . . . . . .
C13 C 1.0032(2) 0.28254(10) 0.4915(2) 0.0306 1.0000 Uani . . . . . .
C14 C 0.0580(3) 0.55896(11) 0.3494(3) 0.0401 1.0000 Uani . . . . . .
C15 C 0.1481(2) 0.51178(10) 0.4026(2) 0.0305 1.0000 Uani . . . . . .
C16 C 0.2311(3) 0.52244(11) 0.5089(3) 0.0374 1.0000 Uani . . . . . .
C17 C 0.3138(3) 0.47950(11) 0.5599(3) 0.0365 1.0000 Uani . . . . . .
C18 C 0.3162(2) 0.42353(10) 0.5052(2) 0.0278 1.0000 Uani . . . . . .
C19 C 0.2337(2) 0.41261(10) 0.3978(2) 0.0285 1.0000 Uani . . . . . .
C20 C 0.1509(2) 0.45621(10) 0.3484(2) 0.0295 1.0000 Uani . . . . . .
C21 C 0.4027(2) 0.37793(10) 0.5659(2) 0.0310 1.0000 Uani . . . . . .
O22 O 0.44490(19) 0.38228(8) 0.67629(17) 0.0475 1.0000 Uani . . . . . .
C23 C 0.4437(2) 0.32578(10) 0.4849(2) 0.0258 1.0000 Uani . . . . . .
C24 C 0.5564(3) 0.34333(11) 0.3976(2) 0.0377 1.0000 Uani . . . . . .
N25 N 0.48569(17) 0.27747(8) 0.57217(17) 0.0242 1.0000 Uani . . . . . .
C26 C 0.5163(2) 0.22137(10) 0.5056(2) 0.0312 1.0000 Uani . . . . . .
Cl1 Cl 0.75029(5) 0.28623(3) 0.72832(5) 0.0291 1.0000 Uani . . . . . .
Cl2 Cl 0.24945(5) 0.26456(3) 0.22983(5) 0.0300 1.0000 Uani . . . . . .
H13 H 0.5230 -0.0602 0.3680 0.0662 1.0000 Uiso R . . . . .
H11 H 0.6568 -0.0950 0.3737 0.0652 1.0000 Uiso R . . . . .
H12 H 0.5652 -0.0937 0.4915 0.0663 1.0000 Uiso R . . . . .
H31 H 0.7211 -0.0483 0.6451 0.0453 1.0000 Uiso R . . . . .
H41 H 0.8366 0.0331 0.7191 0.0399 1.0000 Uiso R . . . . .
H61 H 0.7539 0.1150 0.3801 0.0332 1.0000 Uiso R . . . . .
H71 H 0.6367 0.0333 0.3097 0.0369 1.0000 Uiso R . . . . .
H101 H 0.8743 0.1875 0.4454 0.0275 1.0000 Uiso R . . . . .
H113 H 1.0947 0.1764 0.3817 0.0505 1.0000 Uiso R . . . . .
H111 H 1.1323 0.1450 0.5111 0.0509 1.0000 Uiso R . . . . .
H112 H 1.0397 0.1136 0.4103 0.0510 1.0000 Uiso R . . . . .
H131 H 1.0266 0.3157 0.5454 0.0444 1.0000 Uiso R . . . . .
H133 H 1.0773 0.2739 0.4370 0.0445 1.0000 Uiso R . . . . .
H132 H 0.9245 0.2899 0.4395 0.0451 1.0000 Uiso R . . . . .
H142 H 0.0171 0.5463 0.2680 0.0607 1.0000 Uiso R . . . . .
H141 H 0.1101 0.5940 0.3371 0.0600 1.0000 Uiso R . . . . .
H143 H -0.0109 0.5680 0.4099 0.0595 1.0000 Uiso R . . . . .
H161 H 0.2294 0.5599 0.5469 0.0453 1.0000 Uiso R . . . . .
H171 H 0.3681 0.4873 0.6352 0.0446 1.0000 Uiso R . . . . .
H191 H 0.2349 0.3751 0.3591 0.0340 1.0000 Uiso R . . . . .
H201 H 0.0951 0.4472 0.2771 0.0352 1.0000 Uiso R . . . . .
H231 H 0.3698 0.3120 0.4345 0.0303 1.0000 Uiso R . . . . .
H242 H 0.5767 0.3116 0.3396 0.0558 1.0000 Uiso R . . . . .
H241 H 0.6346 0.3514 0.4514 0.0550 1.0000 Uiso R . . . . .
H243 H 0.5297 0.3773 0.3495 0.0559 1.0000 Uiso R . . . . .
H262 H 0.5375 0.1919 0.5714 0.0457 1.0000 Uiso R . . . . .
H263 H 0.5937 0.2264 0.4533 0.0462 1.0000 Uiso R . . . . .
H261 H 0.4403 0.2099 0.4516 0.0464 1.0000 Uiso R . . . . .
H121 H 1.0534 0.2255 0.6300 0.0346 1.0000 Uiso R . . . . .
H122 H 0.9117 0.2437 0.6351 0.0353 1.0000 Uiso R . . . . .
H251 H 0.5599 0.2887 0.6190 0.0366 1.0000 Uiso R . . . . .
H252 H 0.4180 0.2690 0.6285 0.0366 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0387(15) 0.0338(15) 0.0601(18) -0.0152(13) 0.0096(13) -0.0084(12)
C2 0.0286(13) 0.0277(14) 0.0429(15) -0.0074(11) 0.0081(11) -0.0011(10)
C3 0.0416(15) 0.0248(13) 0.0459(16) 0.0070(12) 0.0031(12) -0.0002(11)
C4 0.0383(14) 0.0290(14) 0.0339(14) 0.0055(11) -0.0022(11) -0.0023(11)
C5 0.0266(12) 0.0246(12) 0.0267(12) -0.0002(10) -0.0007(9) -0.0003(9)
C6 0.0296(12) 0.0284(13) 0.0271(12) 0.0005(10) 0.0018(10) -0.0021(10)
C7 0.0315(13) 0.0339(14) 0.0302(13) -0.0069(11) 0.0013(10) -0.0034(10)
C8 0.0287(12) 0.0250(12) 0.0240(13) 0.0032(10) -0.0030(9) 0.0027(9)
O9 0.0614(12) 0.0349(10) 0.0214(9) 0.0045(7) -0.0107(8) -0.0101(8)
C10 0.0260(12) 0.0242(12) 0.0193(11) -0.0023(9) -0.0034(9) 0.0003(9)
C11 0.0341(14) 0.0288(14) 0.0404(15) -0.0115(11) 0.0062(11) -0.0020(10)
N12 0.0251(10) 0.0235(10) 0.0212(9) -0.0002(8) -0.0009(7) 0.0013(8)
C13 0.0369(14) 0.0266(14) 0.0287(13) 0.0033(10) 0.0055(10) -0.0012(10)
C14 0.0457(16) 0.0290(14) 0.0461(16) 0.0067(12) 0.0108(12) 0.0040(11)
C15 0.0304(13) 0.0280(13) 0.0335(14) 0.0060(11) 0.0091(10) -0.0004(10)
C16 0.0445(15) 0.0243(13) 0.0436(16) -0.0061(11) 0.0044(12) 0.0001(11)
C17 0.0393(14) 0.0315(15) 0.0385(15) -0.0090(12) -0.0047(11) -0.0006(11)
C18 0.0279(12) 0.0277(13) 0.0281(13) -0.0023(10) 0.0020(10) -0.0016(10)
C19 0.0349(13) 0.0242(12) 0.0265(12) -0.0045(10) 0.0012(10) -0.0004(10)
C20 0.0298(13) 0.0291(13) 0.0297(13) -0.0001(10) 0.0012(10) 0.0015(10)
C21 0.0347(14) 0.0311(14) 0.0269(13) -0.0057(10) -0.0038(10) -0.0003(10)
O22 0.0605(13) 0.0480(12) 0.0331(10) -0.0144(9) -0.0184(9) 0.0151(9)
C23 0.0247(12) 0.0272(13) 0.0253(12) -0.0011(10) -0.0047(9) -0.0004(9)
C24 0.0455(16) 0.0341(14) 0.0337(14) 0.0079(11) 0.0072(11) 0.0026(12)
N25 0.0196(9) 0.0294(11) 0.0236(10) -0.0010(8) 0.0001(7) -0.0034(8)
C26 0.0393(14) 0.0245(13) 0.0298(13) -0.0021(10) 0.0015(10) 0.0015(10)
Cl1 0.0230(3) 0.0423(3) 0.0218(3) -0.0065(3) -0.0030(2) 0.0017(2)
Cl2 0.0230(3) 0.0444(4) 0.0224(3) -0.0072(3) -0.0025(2) 0.0033(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.10300(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
C1 . C2 . 1.508(3) yes
C1 . H13 . 0.947 no
C1 . H11 . 0.953 no
C1 . H12 . 0.958 no
C2 . C3 . 1.385(4) yes
C2 . C7 . 1.389(3) yes
C3 . C4 . 1.383(3) yes
C3 . H31 . 0.939 no
C4 . C5 . 1.394(3) yes
C4 . H41 . 0.955 no
C5 . C6 . 1.397(3) yes
C5 . C8 . 1.489(3) yes
C6 . C7 . 1.387(3) yes
C6 . H61 . 0.944 no
C7 . H71 . 0.944 no
C8 . O9 . 1.225(3) yes
C8 . C10 . 1.516(3) yes
C10 . C11 . 1.528(3) yes
C10 . N12 . 1.488(3) yes
C10 . H101 . 0.970 no
C11 . H113 . 0.955 no
C11 . H111 . 0.969 no
C11 . H112 . 0.946 no
N12 . C13 . 1.486(3) yes
N12 . H121 . 0.924 no
N12 . H122 . 0.937 no
C13 . H131 . 0.968 no
C13 . H133 . 0.966 no
C13 . H132 . 0.959 no
C14 . C15 . 1.501(3) yes
C14 . H142 . 0.975 no
C14 . H141 . 0.965 no
C14 . H143 . 0.967 no
C15 . C16 . 1.388(3) yes
C15 . C20 . 1.388(3) yes
C16 . C17 . 1.380(3) yes
C16 . H161 . 0.942 no
C17 . C18 . 1.399(3) yes
C17 . H171 . 0.960 no
C18 . C19 . 1.395(3) yes
C18 . C21 . 1.484(3) yes
C19 . C20 . 1.386(3) yes
C19 . H191 . 0.945 no
C20 . H201 . 0.940 no
C21 . O22 . 1.218(3) yes
C21 . C23 . 1.520(3) yes
C23 . C24 . 1.520(3) yes
C23 . N25 . 1.482(3) yes
C23 . H231 . 0.950 no
C24 . H242 . 0.968 no
C24 . H241 . 0.968 no
C24 . H243 . 0.958 no
N25 . C26 . 1.491(3) yes
N25 . H251 . 0.915 no
N25 . H252 . 0.927 no
C26 . H262 . 0.978 no
C26 . H263 . 0.965 no
C26 . H261 . 0.970 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
C2 . C1 . H13 . 110.0 no
C2 . C1 . H11 . 109.4 no
H13 . C1 . H11 . 109.9 no
C2 . C1 . H12 . 110.9 no
H13 . C1 . H12 . 108.3 no
H11 . C1 . H12 . 108.2 no
C1 . C2 . C3 . 120.6(2) yes
C1 . C2 . C7 . 121.0(2) yes
C3 . C2 . C7 . 118.4(2) yes
C2 . C3 . C4 . 121.2(2) yes
C2 . C3 . H31 . 119.8 no
C4 . C3 . H31 . 119.0 no
C3 . C4 . C5 . 120.4(2) yes
C3 . C4 . H41 . 119.5 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 118.9(2) yes
C4 . C5 . C8 . 118.7(2) yes
C6 . C5 . C8 . 122.4(2) yes
C5 . C6 . C7 . 119.9(2) yes
C5 . C6 . H61 . 120.0 no
C7 . C6 . H61 . 120.2 no
C2 . C7 . C6 . 121.3(2) yes
C2 . C7 . H71 . 120.1 no
C6 . C7 . H71 . 118.6 no
C5 . C8 . O9 . 121.7(2) yes
C5 . C8 . C10 . 118.57(18) yes
O9 . C8 . C10 . 119.6(2) yes
C8 . C10 . C11 . 109.61(19) yes
C8 . C10 . N12 . 109.32(17) yes
C11 . C10 . N12 . 110.64(17) yes
C8 . C10 . H101 . 111.2 no
C11 . C10 . H101 . 109.5 no
N12 . C10 . H101 . 106.5 no
C10 . C11 . H113 . 110.3 no
C10 . C11 . H111 . 108.2 no
H113 . C11 . H111 . 108.7 no
C10 . C11 . H112 . 109.8 no
H113 . C11 . H112 . 111.0 no
H111 . C11 . H112 . 108.8 no
C10 . N12 . C13 . 114.04(17) yes
C10 . N12 . H121 . 109.0 no
C13 . N12 . H121 . 109.6 no
C10 . N12 . H122 . 111.1 no
C13 . N12 . H122 . 107.4 no
H121 . N12 . H122 . 105.4 no
N12 . C13 . H131 . 107.0 no
N12 . C13 . H133 . 110.1 no
H131 . C13 . H133 . 108.7 no
N12 . C13 . H132 . 109.4 no
H131 . C13 . H132 . 111.9 no
H133 . C13 . H132 . 109.6 no
C15 . C14 . H142 . 110.1 no
C15 . C14 . H141 . 108.7 no
H142 . C14 . H141 . 110.3 no
C15 . C14 . H143 . 110.2 no
H142 . C14 . H143 . 109.7 no
H141 . C14 . H143 . 107.8 no
C14 . C15 . C16 . 120.7(2) yes
C14 . C15 . C20 . 121.6(2) yes
C16 . C15 . C20 . 117.7(2) yes
C15 . C16 . C17 . 121.5(2) yes
C15 . C16 . H161 . 118.5 no
C17 . C16 . H161 . 120.0 no
C16 . C17 . C18 . 120.6(2) yes
C16 . C17 . H171 . 120.3 no
C18 . C17 . H171 . 119.1 no
C17 . C18 . C19 . 118.2(2) yes
C17 . C18 . C21 . 118.9(2) yes
C19 . C18 . C21 . 122.8(2) yes
C18 . C19 . C20 . 120.4(2) yes
C18 . C19 . H191 . 119.3 no
C20 . C19 . H191 . 120.4 no
C15 . C20 . C19 . 121.6(2) yes
C15 . C20 . H201 . 120.1 no
C19 . C20 . H201 . 118.4 no
C18 . C21 . O22 . 121.9(2) yes
C18 . C21 . C23 . 118.44(19) yes
O22 . C21 . C23 . 119.6(2) yes
C21 . C23 . C24 . 109.84(19) yes
C21 . C23 . N25 . 108.64(18) yes
C24 . C23 . N25 . 111.02(18) yes
C21 . C23 . H231 . 110.3 no
C24 . C23 . H231 . 109.7 no
N25 . C23 . H231 . 107.3 no
C23 . C24 . H242 . 110.3 no
C23 . C24 . H241 . 107.8 no
H242 . C24 . H241 . 108.9 no
C23 . C24 . H243 . 108.9 no
H242 . C24 . H243 . 109.9 no
H241 . C24 . H243 . 111.0 no
C23 . N25 . C26 . 114.38(17) yes
C23 . N25 . H252 . 109.9 no
C26 . N25 . H252 . 106.1 no
C23 . N25 . H251 . 109.4 no
C26 . N25 . H251 . 108.3 no
H252 . N25 . H251 . 108.6 no
N25 . C26 . H262 . 107.9 no
N25 . C26 . H263 . 109.7 no
H262 . C26 . H263 . 108.3 no
N25 . C26 . H261 . 109.5 no
H262 . C26 . H261 . 111.9 no
H263 . C26 . H261 . 109.5 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 02/09/11 at 11:41:42
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE N   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 263,X'S) H   ( 261,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 02/09/11 at 11:41:42
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983741'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_II_150K
_oxford_structure_analysis_title '150K in P2(1)/c'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone Hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'


#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 

# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 

_cell_length_a                   10.0604(18)
_cell_length_b                   22.876(4)
_cell_length_c                   10.4041(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.741(2)
_cell_angle_gamma                90
_cell_volume                     2393.3(7)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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            8

# Given Formula = C11 H16 Cl1 N1 O2 
# Dc =      1.27 Fooo =    912.00 Mu =      3.01 M =    459.41
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.19 FOOO =    912.00 Mu =      2.90 M =    427.41

_chemical_formula_sum            'C11 H16 Cl1 N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    5197
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.290

# Sheldrick geometric approximatio 0.94 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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      150
_diffrn_reflns_number            15469
_reflns_number_total             4743
_diffrn_reflns_av_R_equivalents  0.052
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4743 
# Theoretical number of reflections is about 9817 


_diffrn_reflns_theta_min         3.853
_diffrn_reflns_theta_max         26.399
_diffrn_measured_fraction_theta_max 0.966

_diffrn_reflns_theta_full        25.343
_diffrn_measured_fraction_theta_full 0.972


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   2.13
_oxford_diffrn_Wilson_scale      100.45

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

_refine_diff_density_min         -0.47
_refine_diff_density_max         0.62


# 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>-10.0\s(I)
_refine_ls_number_reflns         4738
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0840
_refine_ls_wR_factor_ref         0.0769
_refine_ls_goodness_of_fit_ref   0.7821
_refine_ls_shift/su_max          0.0002202
_refine_ls_shift/su_mean         0.0000220


# The values computed from all data 
_oxford_reflns_number_all        4738
_refine_ls_R_factor_all          0.0840
_refine_ls_wR_factor_all         0.0769

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2781
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_gt          0.0717

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5958(2) -0.06915(8) 0.4125(2) 0.0536 1.0000 Uani . . . . . .
C2 C 0.6700(2) -0.01613(8) 0.4612(2) 0.0392 1.0000 Uani . . . . . .
C3 C 0.7331(2) -0.01598(9) 0.5810(2) 0.0451 1.0000 Uani . . . . . .
C4 C 0.8023(2) 0.03210(8) 0.6272(2) 0.0411 1.0000 Uani . . . . . .
C5 C 0.81156(19) 0.08233(8) 0.5513(2) 0.0310 1.0000 Uani . . . . . .
C6 C 0.74793(19) 0.08298(8) 0.4314(2) 0.0336 1.0000 Uani . . . . . .
C7 C 0.6770(2) 0.03443(8) 0.3874(2) 0.0378 1.0000 Uani . . . . . .
C8 C 0.88975(19) 0.13278(8) 0.6026(2) 0.0303 1.0000 Uani . . . . . .
O9 O 0.91697(15) 0.13824(6) 0.71718(14) 0.0485 1.0000 Uani . . . . . .
C10 C 0.94212(19) 0.17711(7) 0.50853(18) 0.0271 1.0000 Uani . . . . . .
C11 C 1.0613(2) 0.15180(8) 0.4405(2) 0.0425 1.0000 Uani . . . . . .
N12 N 0.97980(15) 0.23137(6) 0.57817(14) 0.0270 1.0000 Uani . . . . . .
C13 C 1.0053(2) 0.28248(7) 0.49347(18) 0.0344 1.0000 Uani . . . . . .
C14 C 0.0656(2) 0.55985(8) 0.3576(2) 0.0512 1.0000 Uani . . . . . .
C15 C 0.1532(2) 0.51178(8) 0.4104(2) 0.0379 1.0000 Uani . . . . . .
C16 C 0.2336(2) 0.52113(9) 0.5186(2) 0.0467 1.0000 Uani . . . . . .
C17 C 0.3142(2) 0.47743(8) 0.5705(2) 0.0456 1.0000 Uani . . . . . .
C18 C 0.3171(2) 0.42230(8) 0.5119(2) 0.0332 1.0000 Uani . . . . . .
C19 C 0.23757(19) 0.41273(8) 0.4035(2) 0.0332 1.0000 Uani . . . . . .
C20 C 0.15610(19) 0.45701(8) 0.3536(2) 0.0357 1.0000 Uani . . . . . .
C21 C 0.4023(2) 0.37589(8) 0.5714(2) 0.0344 1.0000 Uani . . . . . .
O22 O 0.44251(16) 0.37879(6) 0.68331(15) 0.0561 1.0000 Uani . . . . . .
C23 C 0.44441(19) 0.32496(7) 0.48887(18) 0.0287 1.0000 Uani . . . . . .
C24 C 0.5578(2) 0.34340(8) 0.4042(2) 0.0435 1.0000 Uani . . . . . .
N25 N 0.48564(15) 0.27569(6) 0.57394(15) 0.0287 1.0000 Uani . . . . . .
C26 C 0.5150(2) 0.22037(7) 0.50485(19) 0.0356 1.0000 Uani . . . . . .
Cl1 Cl 0.75134(5) 0.28339(2) 0.72840(5) 0.0338 1.0000 Uani . . . . . .
Cl2 Cl 0.25053(5) 0.26663(2) 0.22997(5) 0.0347 1.0000 Uani . . . . . .
H13 H 0.5216 -0.0583 0.3595 0.0662 1.0000 Uiso R . . . . .
H11 H 0.6554 -0.0930 0.3652 0.0652 1.0000 Uiso R . . . . .
H12 H 0.5638 -0.0918 0.4830 0.0663 1.0000 Uiso R . . . . .
H31 H 0.7251 -0.0484 0.6358 0.0453 1.0000 Uiso R . . . . .
H41 H 0.8416 0.0320 0.7118 0.0399 1.0000 Uiso R . . . . .
H61 H 0.7538 0.1162 0.3777 0.0332 1.0000 Uiso R . . . . .
H71 H 0.6344 0.0353 0.3054 0.0369 1.0000 Uiso R . . . . .
H101 H 0.8753 0.1876 0.4434 0.0275 1.0000 Uiso R . . . . .
H113 H 1.0934 0.1777 0.3761 0.0505 1.0000 Uiso R . . . . .
H111 H 1.1311 0.1463 0.5056 0.0509 1.0000 Uiso R . . . . .
H112 H 1.0384 0.1149 0.4048 0.0510 1.0000 Uiso R . . . . .
H131 H 1.0287 0.3157 0.5474 0.0444 1.0000 Uiso R . . . . .
H133 H 1.0794 0.2739 0.4389 0.0445 1.0000 Uiso R . . . . .
H132 H 0.9267 0.2899 0.4415 0.0451 1.0000 Uiso R . . . . .
H142 H 0.0247 0.5472 0.2763 0.0607 1.0000 Uiso R . . . . .
H141 H 0.1177 0.5949 0.3454 0.0600 1.0000 Uiso R . . . . .
H143 H -0.0033 0.5689 0.4181 0.0595 1.0000 Uiso R . . . . .
H161 H 0.2319 0.5586 0.5566 0.0453 1.0000 Uiso R . . . . .
H171 H 0.3686 0.4853 0.6458 0.0446 1.0000 Uiso R . . . . .
H191 H 0.2387 0.3752 0.3648 0.0340 1.0000 Uiso R . . . . .
H201 H 0.1002 0.4480 0.2823 0.0352 1.0000 Uiso R . . . . .
H231 H 0.3705 0.3112 0.4384 0.0303 1.0000 Uiso R . . . . .
H242 H 0.5781 0.3117 0.3461 0.0558 1.0000 Uiso R . . . . .
H241 H 0.6359 0.3515 0.4579 0.0550 1.0000 Uiso R . . . . .
H243 H 0.5311 0.3774 0.3560 0.0559 1.0000 Uiso R . . . . .
H262 H 0.5362 0.1909 0.5706 0.0457 1.0000 Uiso R . . . . .
H263 H 0.5924 0.2254 0.4525 0.0462 1.0000 Uiso R . . . . .
H261 H 0.4390 0.2089 0.4508 0.0465 1.0000 Uiso R . . . . .
H121 H 1.0548 0.2246 0.6296 0.0346 1.0000 Uiso R . . . . .
H122 H 0.9131 0.2428 0.6347 0.0353 1.0000 Uiso R . . . . .
H252 H 0.4179 0.2672 0.6303 0.0366 1.0000 Uiso R . . . . .
H251 H 0.5600 0.2887 0.6191 0.0366 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0479(15) 0.0364(12) 0.0775(19) -0.0176(12) 0.0173(14) -0.0124(11)
C2 0.0326(12) 0.0313(11) 0.0545(16) -0.0094(11) 0.0137(12) -0.0027(10)
C3 0.0458(14) 0.0281(11) 0.0618(18) 0.0087(11) 0.0084(13) -0.0007(10)
C4 0.0465(14) 0.0316(11) 0.0452(15) 0.0070(10) -0.0010(11) -0.0018(10)
C5 0.0321(12) 0.0293(11) 0.0316(13) 0.0003(9) 0.0025(10) 0.0002(9)
C6 0.0357(13) 0.0312(11) 0.0342(13) 0.0026(9) 0.0069(11) -0.0020(9)
C7 0.0331(12) 0.0407(12) 0.0397(14) -0.0088(10) 0.0040(11) -0.0042(10)
C8 0.0331(12) 0.0314(11) 0.0262(13) 0.0013(9) -0.0013(10) 0.0022(9)
O9 0.0696(11) 0.0445(9) 0.0307(9) 0.0070(7) -0.0100(8) -0.0119(8)
C10 0.0282(12) 0.0288(10) 0.0239(11) -0.0016(8) -0.0029(9) -0.0009(8)
C11 0.0439(14) 0.0378(12) 0.0463(15) -0.0130(10) 0.0122(12) -0.0019(10)
N12 0.0252(10) 0.0287(8) 0.0270(10) -0.0005(7) 0.0024(8) 0.0020(7)
C13 0.0418(14) 0.0289(12) 0.0329(13) 0.0033(9) 0.0072(11) -0.0009(9)
C14 0.0568(16) 0.0337(12) 0.0641(18) 0.0129(11) 0.0198(14) 0.0092(11)
C15 0.0398(13) 0.0295(11) 0.0451(15) 0.0047(10) 0.0149(12) -0.0021(10)
C16 0.0515(15) 0.0250(11) 0.0641(18) -0.0085(11) 0.0095(14) -0.0018(10)
C17 0.0505(15) 0.0373(13) 0.0489(16) -0.0129(11) -0.0028(12) -0.0019(11)
C18 0.0328(12) 0.0297(11) 0.0375(14) -0.0042(9) 0.0045(11) -0.0015(9)
C19 0.0354(13) 0.0297(11) 0.0347(13) -0.0045(9) 0.0027(10) 0.0002(9)
C20 0.0349(13) 0.0340(11) 0.0383(14) 0.0006(10) 0.0039(11) 0.0026(9)
C21 0.0350(13) 0.0366(12) 0.0315(13) -0.0071(9) -0.0023(11) -0.0034(9)
O22 0.0689(12) 0.0569(10) 0.0414(11) -0.0168(8) -0.0165(9) 0.0163(8)
C23 0.0277(12) 0.0292(10) 0.0291(12) 0.0003(9) -0.0015(9) 0.0003(8)
C24 0.0486(14) 0.0384(12) 0.0443(14) 0.0100(10) 0.0135(12) 0.0039(10)
N25 0.0236(10) 0.0331(9) 0.0296(10) -0.0012(7) 0.0019(8) -0.0041(7)
C26 0.0405(14) 0.0298(12) 0.0366(14) -0.0032(9) 0.0038(11) 0.0000(9)
Cl1 0.0231(3) 0.0510(3) 0.0271(3) -0.0087(2) -0.0007(2) 0.0027(2)
Cl2 0.0246(3) 0.0526(3) 0.0268(3) -0.0084(2) -0.0001(2) 0.0042(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.16404(6)
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
C1 . C2 . 1.504(3) yes
C1 . H13 . 0.948 no
C1 . H11 . 0.958 no
C1 . H12 . 0.961 no
C2 . C3 . 1.381(3) yes
C2 . C7 . 1.391(3) yes
C3 . C4 . 1.380(3) yes
C3 . H31 . 0.941 no
C4 . C5 . 1.399(2) yes
C4 . H41 . 0.954 no
C5 . C6 . 1.384(3) yes
C5 . C8 . 1.487(3) yes
C6 . C7 . 1.390(3) yes
C6 . H61 . 0.946 no
C7 . H71 . 0.943 no
C8 . O9 . 1.221(2) yes
C8 . C10 . 1.515(2) yes
C10 . C11 . 1.525(2) yes
C10 . N12 . 1.481(2) yes
C10 . H101 . 0.970 no
C11 . H113 . 0.958 no
C11 . H111 . 0.969 no
C11 . H112 . 0.947 no
N12 . C13 . 1.491(2) yes
N12 . H121 . 0.925 no
N12 . H122 . 0.942 no
C13 . H131 . 0.969 no
C13 . H133 . 0.971 no
C13 . H132 . 0.960 no
C14 . C15 . 1.502(3) yes
C14 . H142 . 0.974 no
C14 . H141 . 0.968 no
C14 . H143 . 0.972 no
C15 . C16 . 1.383(3) yes
C15 . C20 . 1.386(3) yes
C16 . C17 . 1.386(3) yes
C16 . H161 . 0.944 no
C17 . C18 . 1.401(3) yes
C17 . H171 . 0.959 no
C18 . C19 . 1.381(3) yes
C18 . C21 . 1.487(3) yes
C19 . C20 . 1.393(3) yes
C19 . H191 . 0.947 no
C20 . H201 . 0.940 no
C21 . O22 . 1.222(2) yes
C21 . C23 . 1.516(2) yes
C23 . C24 . 1.522(2) yes
C23 . N25 . 1.484(2) yes
C23 . H231 . 0.951 no
C24 . H242 . 0.970 no
C24 . H241 . 0.969 no
C24 . H243 . 0.959 no
N25 . C26 . 1.490(2) yes
N25 . H252 . 0.932 no
N25 . H251 . 0.920 no
C26 . H262 . 0.979 no
C26 . H263 . 0.971 no
C26 . H261 . 0.971 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
C2 . C1 . H13 . 111.0 no
C2 . C1 . H11 . 108.7 no
H13 . C1 . H11 . 110.2 no
C2 . C1 . H12 . 110.6 no
H13 . C1 . H12 . 108.0 no
H11 . C1 . H12 . 108.4 no
C1 . C2 . C3 . 121.0(2) yes
C1 . C2 . C7 . 121.2(2) yes
C3 . C2 . C7 . 117.8(2) yes
C2 . C3 . C4 . 122.0(2) yes
C2 . C3 . H31 . 120.0 no
C4 . C3 . H31 . 118.0 no
C3 . C4 . C5 . 120.0(2) yes
C3 . C4 . H41 . 120.6 no
C5 . C4 . H41 . 119.4 no
C4 . C5 . C6 . 118.71(19) yes
C4 . C5 . C8 . 118.6(2) yes
C6 . C5 . C8 . 122.70(18) yes
C5 . C6 . C7 . 120.45(19) yes
C5 . C6 . H61 . 120.4 no
C7 . C6 . H61 . 119.1 no
C2 . C7 . C6 . 121.1(2) yes
C2 . C7 . H71 . 119.2 no
C6 . C7 . H71 . 119.7 no
C5 . C8 . O9 . 122.04(18) yes
C5 . C8 . C10 . 118.55(18) yes
O9 . C8 . C10 . 119.35(17) yes
C8 . C10 . C11 . 109.86(15) yes
C8 . C10 . N12 . 109.49(15) yes
C11 . C10 . N12 . 110.63(15) yes
C8 . C10 . H101 . 111.6 no
C11 . C10 . H101 . 107.9 no
N12 . C10 . H101 . 107.3 no
C10 . C11 . H113 . 112.1 no
C10 . C11 . H111 . 106.8 no
H113 . C11 . H111 . 108.4 no
C10 . C11 . H112 . 109.6 no
H113 . C11 . H112 . 111.1 no
H111 . C11 . H112 . 108.7 no
C10 . N12 . C13 . 114.47(15) yes
C10 . N12 . H121 . 109.6 no
C13 . N12 . H121 . 108.7 no
C10 . N12 . H122 . 111.2 no
C13 . N12 . H122 . 106.8 no
H121 . N12 . H122 . 105.6 no
N12 . C13 . H131 . 108.4 no
N12 . C13 . H133 . 109.6 no
H131 . C13 . H133 . 108.7 no
N12 . C13 . H132 . 108.5 no
H131 . C13 . H132 . 111.7 no
H133 . C13 . H132 . 109.9 no
C15 . C14 . H142 . 109.2 no
C15 . C14 . H141 . 109.9 no
H142 . C14 . H141 . 110.3 no
C15 . C14 . H143 . 110.0 no
H142 . C14 . H143 . 109.6 no
H141 . C14 . H143 . 108.0 no
C14 . C15 . C16 . 120.4(2) yes
C14 . C15 . C20 . 121.7(2) yes
C16 . C15 . C20 . 117.9(2) yes
C15 . C16 . C17 . 121.8(2) yes
C15 . C16 . H161 . 117.7 no
C17 . C16 . H161 . 120.6 no
C16 . C17 . C18 . 120.0(2) yes
C16 . C17 . H171 . 119.7 no
C18 . C17 . H171 . 120.3 no
C17 . C18 . C19 . 118.57(19) yes
C17 . C18 . C21 . 118.8(2) yes
C19 . C18 . C21 . 122.63(17) yes
C18 . C19 . C20 . 120.59(18) yes
C18 . C19 . H191 . 118.4 no
C20 . C19 . H191 . 121.0 no
C19 . C20 . C15 . 121.2(2) yes
C19 . C20 . H201 . 117.8 no
C15 . C20 . H201 . 120.9 no
C18 . C21 . O22 . 121.82(18) yes
C18 . C21 . C23 . 118.71(19) yes
O22 . C21 . C23 . 119.42(19) yes
C21 . C23 . C24 . 110.03(15) yes
C21 . C23 . N25 . 108.88(16) yes
C24 . C23 . N25 . 110.79(15) yes
C21 . C23 . H231 . 109.9 no
C24 . C23 . H231 . 111.1 no
N25 . C23 . H231 . 106.1 no
C23 . C24 . H242 . 109.2 no
C23 . C24 . H241 . 109.1 no
H242 . C24 . H241 . 108.6 no
C23 . C24 . H243 . 108.9 no
H242 . C24 . H243 . 110.1 no
H241 . C24 . H243 . 110.9 no
C23 . N25 . C26 . 114.41(15) yes
C23 . N25 . H252 . 109.6 no
C26 . N25 . H252 . 106.7 no
C23 . N25 . H251 . 105.5 no
C26 . N25 . H251 . 110.5 no
H252 . N25 . H251 . 110.1 no
N25 . C26 . H262 . 106.8 no
N25 . C26 . H263 . 110.1 no
H262 . C26 . H263 . 108.2 no
N25 . C26 . H261 . 110.2 no
H262 . C26 . H261 . 111.7 no
H263 . C26 . H261 . 109.8 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/09/11 at 11:37:57
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE N   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 263,X'S) H   ( 261,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/09/11 at 11:37:57
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983742'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_I_180K
_oxford_structure_analysis_title '180K in P2(1)/n'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone Hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'



#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 

# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 



_cell_length_a                   7.1160(12)
_cell_length_b                   22.916(4)
_cell_length_c                   7.3818(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.415(2)
_cell_angle_gamma                90
_cell_volume                     1203.4(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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 = C11 H16 Cl1 N1 O1 
# Dc =      1.18 Fooo =    456.00 Mu =      2.88 M =    213.71
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.18 FOOO =    456.00 Mu =      2.88 M =    213.71

_chemical_formula_sum            'C11 H16 Cl1 N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    2113
_cell_measurement_theta_min      4
_cell_measurement_theta_max      26
_cell_measurement_temperature    180

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.288

# Sheldrick geometric approximatio 0.94 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# 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            7763
_reflns_number_total             2390
_diffrn_reflns_av_R_equivalents  0.041
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2390 
# Theoretical number of reflections is about 4924 


_diffrn_reflns_theta_min         3.839
_diffrn_reflns_theta_max         26.376
_diffrn_measured_fraction_theta_max 0.973

_diffrn_reflns_theta_full        25.057
_diffrn_measured_fraction_theta_full 0.975


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   4.96
_oxford_diffrn_Wilson_scale      89.86

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

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.33


# 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>-10.0\s(I)
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     0
_refine_ls_number_parameters     127
_oxford_refine_ls_R_factor_ref   0.0639
_refine_ls_wR_factor_ref         0.0989
_refine_ls_goodness_of_fit_ref   0.9037
_refine_ls_shift/su_max          0.0012811
_refine_ls_shift/su_mean         0.0000458


# The values computed from all data 
_oxford_reflns_number_all        2386
_refine_ls_R_factor_all          0.0639
_refine_ls_wR_factor_all         0.0989

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1655
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_gt          0.0951

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5270(4) 0.43632(9) 0.8017(3) 0.0713 1.0000 Uani . . . . . .
C2 C 0.3952(4) 0.48702(8) 0.7707(3) 0.0514 1.0000 Uani . . . . . .
C3 C 0.2068(4) 0.48250(9) 0.8128(3) 0.0610 1.0000 Uani . . . . . .
C4 C 0.0842(4) 0.52868(9) 0.7871(3) 0.0572 1.0000 Uani . . . . . .
C5 C 0.1472(3) 0.58120(8) 0.7147(3) 0.0409 1.0000 Uani . . . . . .
C6 C 0.3346(3) 0.58613(8) 0.6728(2) 0.0409 1.0000 Uani . . . . . .
C7 C 0.4581(3) 0.53974(8) 0.7015(3) 0.0472 1.0000 Uani . . . . . .
C8 C 0.0105(3) 0.62968(8) 0.6884(3) 0.0402 1.0000 Uani . . . . . .
O9 O -0.1387(2) 0.63122(6) 0.7665(2) 0.0652 1.0000 Uani . . . . . .
C10 C 0.0557(3) 0.67738(7) 0.5532(2) 0.0337 1.0000 Uani . . . . . .
C11 C 0.0190(3) 0.65515(9) 0.3601(3) 0.0538 1.0000 Uani . . . . . .
N12 N -0.0623(2) 0.72912(6) 0.59033(19) 0.0332 1.0000 Uani . . . . . .
C13 C -0.0108(3) 0.78203(8) 0.4857(2) 0.0428 1.0000 Uani . . . . . .
Cl1 Cl 0.01792(7) 0.77469(2) 0.97374(6) 0.0419 1.0000 Uani . . . . . .
H13 H 0.6612 0.4434 0.7710 0.1743 1.0000 Uiso R . . . . .
H11 H 0.5267 0.4206 0.9279 0.1738 1.0000 Uiso R . . . . .
H12 H 0.4897 0.4009 0.7275 0.1738 1.0000 Uiso R . . . . .
H31 H 0.1708 0.4421 0.8632 0.1185 1.0000 Uiso R . . . . .
H41 H -0.0373 0.5206 0.8227 0.1099 1.0000 Uiso R . . . . .
H61 H 0.3924 0.6192 0.6262 0.0794 1.0000 Uiso R . . . . .
H71 H 0.5923 0.5421 0.6745 0.0928 1.0000 Uiso R . . . . .
H101 H 0.1851 0.6880 0.5766 0.0647 1.0000 Uiso R . . . . .
H113 H 0.0572 0.6828 0.2820 0.1255 1.0000 Uiso R . . . . .
H111 H -0.1179 0.6451 0.3416 0.1257 1.0000 Uiso R . . . . .
H112 H 0.0819 0.6190 0.3492 0.1262 1.0000 Uiso R . . . . .
H131 H -0.0924 0.8157 0.5251 0.1028 1.0000 Uiso R . . . . .
H133 H 0.1147 0.7933 0.5125 0.1028 1.0000 Uiso R . . . . .
H132 H -0.0306 0.7772 0.3616 0.1028 1.0000 Uiso R . . . . .
H122 H -0.0592 0.7373 0.7188 0.0804 1.0000 Uiso R . . . . .
H121 H -0.1809 0.7197 0.5806 0.0804 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.114(2) 0.0404(12) 0.0583(14) -0.0055(10) -0.0135(14) 0.0314(14)
C2 0.0763(19) 0.0387(12) 0.0384(11) -0.0061(9) -0.0129(11) 0.0076(11)
C3 0.088(2) 0.0338(12) 0.0611(14) 0.0053(10) -0.0086(14) -0.0078(12)
C4 0.0651(18) 0.0405(12) 0.0661(15) 0.0090(10) 0.0027(12) -0.0121(11)
C5 0.0464(14) 0.0340(10) 0.0421(11) 0.0023(8) -0.0002(9) -0.0037(9)
C6 0.0481(14) 0.0365(11) 0.0381(11) 0.0019(8) 0.0002(9) 0.0001(9)
C7 0.0584(15) 0.0422(12) 0.0407(11) 0.0002(9) -0.0040(10) 0.0113(10)
C8 0.0358(13) 0.0387(11) 0.0463(12) 0.0025(9) 0.0041(9) -0.0074(9)
O9 0.0471(11) 0.0613(10) 0.0884(12) 0.0230(9) 0.0237(9) -0.0019(8)
C10 0.0311(11) 0.0349(10) 0.0352(10) -0.0011(7) 0.0004(8) 0.0027(8)
C11 0.0731(18) 0.0458(12) 0.0422(12) -0.0118(9) -0.0026(11) 0.0114(11)
N12 0.0315(9) 0.0363(8) 0.0317(8) -0.0029(6) 0.0015(6) -0.0014(7)
C13 0.0522(14) 0.0354(11) 0.0409(11) 0.0024(8) 0.0024(10) -0.0018(9)
Cl1 0.0294(3) 0.0642(3) 0.0319(2) -0.0107(2) -0.00176(17) 0.0052(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3312(5)
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
C1 . C2 . 1.507(3) yes
C1 . H13 . 1.000 no
C1 . H11 . 0.999 no
C1 . H12 . 1.010 no
C2 . C3 . 1.388(4) yes
C2 . C7 . 1.390(3) yes
C3 . C4 . 1.382(3) yes
C3 . H31 . 1.033 no
C4 . C5 . 1.395(3) yes
C4 . H41 . 0.928 no
C5 . C6 . 1.381(3) yes
C5 . C8 . 1.486(3) yes
C6 . C7 . 1.392(3) yes
C6 . H61 . 0.932 no
C7 . H71 . 0.982 no
C8 . O9 . 1.221(2) yes
C8 . C10 . 1.520(2) yes
C10 . C11 . 1.530(3) yes
C10 . N12 . 1.482(2) yes
C10 . H101 . 0.964 no
C11 . H113 . 0.903 no
C11 . H111 . 1.007 no
C11 . H112 . 0.947 no
N12 . C13 . 1.488(2) yes
N12 . H122 . 0.967 no
N12 . H121 . 0.873 no
C13 . H131 . 1.013 no
C13 . H133 . 0.946 no
C13 . H132 . 0.930 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
C2 . C1 . H13 . 115.8 no
C2 . C1 . H11 . 113.8 no
H13 . C1 . H11 . 107.1 no
C2 . C1 . H12 . 112.5 no
H13 . C1 . H12 . 104.3 no
H11 . C1 . H12 . 102.1 no
C1 . C2 . C3 . 120.6(2) yes
C1 . C2 . C7 . 121.4(3) yes
C3 . C2 . C7 . 118.0(2) yes
C2 . C3 . C4 . 121.5(2) yes
C2 . C3 . H31 . 113.4 no
C4 . C3 . H31 . 125.1 no
C3 . C4 . C5 . 120.4(2) yes
C3 . C4 . H41 . 113.4 no
C5 . C4 . H41 . 126.2 no
C4 . C5 . C6 . 118.52(19) yes
C4 . C5 . C8 . 118.6(2) yes
C6 . C5 . C8 . 122.83(17) yes
C5 . C6 . C7 . 120.86(19) yes
C5 . C6 . H61 . 125.9 no
C7 . C6 . H61 . 113.2 no
C6 . C7 . C2 . 120.8(2) yes
C6 . C7 . H71 . 122.7 no
C2 . C7 . H71 . 116.5 no
C5 . C8 . O9 . 122.26(18) yes
C5 . C8 . C10 . 118.38(18) yes
O9 . C8 . C10 . 119.31(18) yes
C8 . C10 . C11 . 109.78(15) yes
C8 . C10 . N12 . 108.90(15) yes
C11 . C10 . N12 . 110.76(15) yes
C8 . C10 . H101 . 106.3 no
C11 . C10 . H101 . 113.0 no
N12 . C10 . H101 . 107.9 no
C10 . C11 . H113 . 108.3 no
C10 . C11 . H111 . 110.2 no
H113 . C11 . H111 . 112.3 no
C10 . C11 . H112 . 107.5 no
H113 . C11 . H112 . 114.2 no
H111 . C11 . H112 . 104.2 no
C10 . N12 . C13 . 114.07(15) yes
C10 . N12 . H122 . 109.7 no
C13 . N12 . H122 . 110.5 no
C10 . N12 . H121 . 109.7 no
C13 . N12 . H121 . 114.2 no
H122 . N12 . H121 . 97.3 no
N12 . C13 . H131 . 108.7 no
N12 . C13 . H133 . 111.0 no
H131 . C13 . H133 . 106.1 no
N12 . C13 . H132 . 112.4 no
H131 . C13 . H132 . 107.4 no
H133 . C13 . H132 . 111.0 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/09/11 at 11:16:52
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/09/11 at 11:16:52
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983743'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_I_210K
_oxford_structure_analysis_title '210K in P2(1)/n'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone Hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'


#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 
# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 


_cell_length_a                   7.1234(14)
_cell_length_b                   22.966(4)
_cell_length_c                   7.3986(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.146(2)
_cell_angle_gamma                90
_cell_volume                     1210.1(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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 = C11 H16 Cl1 N1 O1 
# Dc =      1.17 Fooo =    456.00 Mu =      2.86 M =    213.71
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.17 FOOO =    456.00 Mu =      2.86 M =    213.71

_chemical_formula_sum            'C11 H16 Cl1 N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    518
_cell_measurement_theta_min      4
_cell_measurement_theta_max      24
_cell_measurement_temperature    210

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.286

# Sheldrick geometric approximatio 0.94 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# 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      210
_diffrn_reflns_number            7803
_reflns_number_total             2402
_diffrn_reflns_av_R_equivalents  0.032
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2402 
# Theoretical number of reflections is about 4958 


_diffrn_reflns_theta_min         3.830
_diffrn_reflns_theta_max         26.387
_diffrn_measured_fraction_theta_max 0.970

_diffrn_reflns_theta_full        25.596
_diffrn_measured_fraction_theta_full 0.974


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   4.96
_oxford_diffrn_Wilson_scale      89.86

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

_refine_diff_density_min         -0.30
_refine_diff_density_max         0.43


# 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>-10.0\s(I)
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_number_parameters     127
_oxford_refine_ls_R_factor_ref   0.0677
_refine_ls_wR_factor_ref         0.1072
_refine_ls_goodness_of_fit_ref   0.9846
_refine_ls_shift/su_max          0.0006256
_refine_ls_shift/su_mean         0.0000282


# The values computed from all data 
_oxford_reflns_number_all        2398
_refine_ls_R_factor_all          0.0677
_refine_ls_wR_factor_all         0.1072

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1663
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_gt          0.0909

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.58P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5225(5) 0.43673(11) 0.8010(4) 0.0806 1.0000 Uani . . . . . .
C2 C 0.3907(5) 0.48748(10) 0.7703(3) 0.0588 1.0000 Uani . . . . . .
C3 C 0.2027(5) 0.48295(11) 0.8114(4) 0.0700 1.0000 Uani . . . . . .
C4 C 0.0801(4) 0.52936(11) 0.7846(4) 0.0655 1.0000 Uani . . . . . .
C5 C 0.1447(3) 0.58163(9) 0.7132(3) 0.0456 1.0000 Uani . . . . . .
C6 C 0.3329(3) 0.58640(9) 0.6728(3) 0.0473 1.0000 Uani . . . . . .
C7 C 0.4551(4) 0.53977(10) 0.7016(3) 0.0538 1.0000 Uani . . . . . .
C8 C 0.0092(3) 0.63020(9) 0.6870(3) 0.0462 1.0000 Uani . . . . . .
O9 O -0.1405(3) 0.63173(8) 0.7642(3) 0.0730 1.0000 Uani . . . . . .
C10 C 0.0558(3) 0.67775(9) 0.5522(3) 0.0381 1.0000 Uani . . . . . .
C11 C 0.0215(4) 0.65573(11) 0.3598(3) 0.0605 1.0000 Uani . . . . . .
N12 N -0.0624(2) 0.72939(7) 0.5889(2) 0.0375 1.0000 Uani . . . . . .
C13 C -0.0104(3) 0.78216(9) 0.4844(3) 0.0483 1.0000 Uani . . . . . .
Cl1 Cl 0.01850(8) 0.77463(3) 0.97177(7) 0.0481 1.0000 Uani . . . . . .
H13 H 0.6567 0.4438 0.7703 0.1743 1.0000 Uiso R . . . . .
H11 H 0.5221 0.4210 0.9272 0.1738 1.0000 Uiso R . . . . .
H12 H 0.4851 0.4014 0.7268 0.1738 1.0000 Uiso R . . . . .
H31 H 0.1667 0.4425 0.8617 0.1185 1.0000 Uiso R . . . . .
H41 H -0.0413 0.5213 0.8202 0.1099 1.0000 Uiso R . . . . .
H61 H 0.3907 0.6195 0.6261 0.0794 1.0000 Uiso R . . . . .
H71 H 0.5893 0.5421 0.6746 0.0928 1.0000 Uiso R . . . . .
H101 H 0.1853 0.6884 0.5756 0.0647 1.0000 Uiso R . . . . .
H113 H 0.0596 0.6834 0.2817 0.1255 1.0000 Uiso R . . . . .
H111 H -0.1154 0.6456 0.3413 0.1257 1.0000 Uiso R . . . . .
H112 H 0.0844 0.6195 0.3489 0.1262 1.0000 Uiso R . . . . .
H131 H -0.0920 0.8158 0.5238 0.1028 1.0000 Uiso R . . . . .
H133 H 0.1152 0.7935 0.5112 0.1028 1.0000 Uiso R . . . . .
H132 H -0.0302 0.7774 0.3603 0.1028 1.0000 Uiso R . . . . .
H122 H -0.0593 0.7376 0.7174 0.0804 1.0000 Uiso R . . . . .
H121 H -0.1810 0.7199 0.5791 0.0804 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.131(3) 0.0467(15) 0.0635(17) -0.0049(13) -0.0159(17) 0.0312(17)
C2 0.090(2) 0.0418(14) 0.0444(14) -0.0054(10) -0.0104(13) 0.0090(13)
C3 0.100(3) 0.0383(14) 0.0718(18) 0.0075(12) -0.0063(17) -0.0089(14)
C4 0.0718(19) 0.0475(15) 0.0772(18) 0.0103(13) 0.0028(14) -0.0143(14)
C5 0.0514(15) 0.0378(12) 0.0476(13) 0.0018(9) 0.0018(10) -0.0047(10)
C6 0.0554(16) 0.0420(12) 0.0446(12) 0.0035(9) 0.0017(11) 0.0004(11)
C7 0.0630(17) 0.0497(14) 0.0483(13) -0.0003(11) -0.0029(12) 0.0129(12)
C8 0.0415(14) 0.0449(13) 0.0524(14) 0.0022(10) 0.0060(11) -0.0081(10)
O9 0.0530(12) 0.0680(12) 0.0990(15) 0.0245(10) 0.0272(10) -0.0004(9)
C10 0.0344(12) 0.0402(11) 0.0397(11) -0.0011(9) 0.0016(9) 0.0007(9)
C11 0.080(2) 0.0548(15) 0.0469(14) -0.0142(11) -0.0001(13) 0.0147(13)
N12 0.0354(10) 0.0403(10) 0.0370(9) -0.0032(7) 0.0010(7) -0.0019(8)
C13 0.0584(16) 0.0395(12) 0.0471(13) 0.0029(10) 0.0019(11) -0.0020(11)
Cl1 0.0333(3) 0.0738(4) 0.0369(3) -0.0119(3) -0.00264(19) 0.0060(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.20368(18)
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
C1 . C2 . 1.511(4) yes
C1 . H13 . 1.000 no
C1 . H11 . 1.001 no
C1 . H12 . 1.013 no
C2 . C3 . 1.384(4) yes
C2 . C7 . 1.386(4) yes
C3 . C4 . 1.389(4) yes
C3 . H31 . 1.035 no
C4 . C5 . 1.393(3) yes
C4 . H41 . 0.928 no
C5 . C6 . 1.384(3) yes
C5 . C8 . 1.485(3) yes
C6 . C7 . 1.394(3) yes
C6 . H61 . 0.934 no
C7 . H71 . 0.982 no
C8 . O9 . 1.221(3) yes
C8 . C10 . 1.520(3) yes
C10 . C11 . 1.526(3) yes
C10 . N12 . 1.483(3) yes
C10 . H101 . 0.966 no
C11 . H113 . 0.904 no
C11 . H111 . 1.009 no
C11 . H112 . 0.948 no
N12 . C13 . 1.488(3) yes
N12 . H122 . 0.969 no
N12 . H121 . 0.874 no
C13 . H131 . 1.014 no
C13 . H133 . 0.948 no
C13 . H132 . 0.933 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
C2 . C1 . H13 . 115.7 no
C2 . C1 . H11 . 113.9 no
H13 . C1 . H11 . 106.9 no
C2 . C1 . H12 . 112.5 no
H13 . C1 . H12 . 104.4 no
H11 . C1 . H12 . 102.2 no
C1 . C2 . C3 . 120.7(3) yes
C1 . C2 . C7 . 121.0(3) yes
C3 . C2 . C7 . 118.3(2) yes
C2 . C3 . C4 . 121.3(2) yes
C2 . C3 . H31 . 113.2 no
C4 . C3 . H31 . 125.5 no
C3 . C4 . C5 . 120.3(3) yes
C3 . C4 . H41 . 113.1 no
C5 . C4 . H41 . 126.6 no
C4 . C5 . C6 . 118.6(2) yes
C4 . C5 . C8 . 118.6(2) yes
C6 . C5 . C8 . 122.8(2) yes
C5 . C6 . C7 . 120.7(2) yes
C5 . C6 . H61 . 125.5 no
C7 . C6 . H61 . 113.8 no
C6 . C7 . C2 . 120.8(3) yes
C6 . C7 . H71 . 122.3 no
C2 . C7 . H71 . 116.9 no
C5 . C8 . O9 . 122.1(2) yes
C5 . C8 . C10 . 118.4(2) yes
O9 . C8 . C10 . 119.4(2) yes
C8 . C10 . C11 . 109.95(18) yes
C8 . C10 . N12 . 108.80(17) yes
C11 . C10 . N12 . 110.79(17) yes
C8 . C10 . H101 . 106.5 no
C11 . C10 . H101 . 112.7 no
N12 . C10 . H101 . 108.0 no
C10 . C11 . H113 . 108.6 no
C10 . C11 . H111 . 109.8 no
H113 . C11 . H111 . 112.1 no
C10 . C11 . H112 . 107.6 no
H113 . C11 . H112 . 114.4 no
H111 . C11 . H112 . 104.1 no
C10 . N12 . C13 . 114.09(17) yes
C10 . N12 . H122 . 109.5 no
C13 . N12 . H122 . 110.5 no
C10 . N12 . H121 . 109.8 no
C13 . N12 . H121 . 114.2 no
H122 . N12 . H121 . 97.6 no
N12 . C13 . H131 . 108.8 no
N12 . C13 . H133 . 111.0 no
H131 . C13 . H133 . 106.0 no
N12 . C13 . H132 . 112.4 no
H131 . C13 . H132 . 107.3 no
H133 . C13 . H132 . 111.2 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/09/11 at 09:57:59
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/09/11 at 09:57:59
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983744'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_I_230K
_oxford_structure_analysis_title '230K in P2(1)/n'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'

#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 
# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 


_cell_length_a                   7.1264(14)
_cell_length_b                   22.986(5)
_cell_length_c                   7.4072(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.974(2)
_cell_angle_gamma                90
_cell_volume                     1213.2(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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 = C11 H15 Cl1 N1 O1 
# Dc =      1.16 Fooo =    456.00 Mu =      2.86 M =    212.70
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.17 FOOO =    456.00 Mu =      2.86 M =    213.71

_chemical_formula_sum            'C11 H16 Cl1 N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    1865
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25
_cell_measurement_temperature    230

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.286

# Sheldrick geometric approximatio 0.94 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# 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      230
_diffrn_reflns_number            7848
_reflns_number_total             2415
_diffrn_reflns_av_R_equivalents  0.032
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2415 
# Theoretical number of reflections is about 4966 


_diffrn_reflns_theta_min         3.826
_diffrn_reflns_theta_max         26.379
_diffrn_measured_fraction_theta_max 0.973

_diffrn_reflns_theta_full        25.588
_diffrn_measured_fraction_theta_full 0.975


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   4.96
_oxford_diffrn_Wilson_scale      89.86

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

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.42


# 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>-10.0\s(I)
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     0
_refine_ls_number_parameters     127
_oxford_refine_ls_R_factor_ref   0.0714
_refine_ls_wR_factor_ref         0.1150
_refine_ls_goodness_of_fit_ref   0.9794
_refine_ls_shift/su_max          0.0003707
_refine_ls_shift/su_mean         0.0000305


# The values computed from all data 
_oxford_reflns_number_all        2411
_refine_ls_R_factor_all          0.0714
_refine_ls_wR_factor_all         0.1150

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1616
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_gt          0.0939

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.55P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5184(5) 0.43692(12) 0.8010(4) 0.0877 1.0000 Uani . . . . . .
C2 C 0.3887(5) 0.48774(11) 0.7695(3) 0.0654 1.0000 Uani . . . . . .
C3 C 0.2001(6) 0.48346(12) 0.8099(4) 0.0761 1.0000 Uani . . . . . .
C4 C 0.0779(5) 0.52973(11) 0.7833(4) 0.0723 1.0000 Uani . . . . . .
C5 C 0.1432(4) 0.58207(10) 0.7123(3) 0.0507 1.0000 Uani . . . . . .
C6 C 0.3320(4) 0.58658(10) 0.6726(3) 0.0513 1.0000 Uani . . . . . .
C7 C 0.4531(4) 0.54016(11) 0.7014(3) 0.0598 1.0000 Uani . . . . . .
C8 C 0.0083(3) 0.63047(10) 0.6855(3) 0.0509 1.0000 Uani . . . . . .
O9 O -0.1418(3) 0.63214(8) 0.7629(3) 0.0806 1.0000 Uani . . . . . .
C10 C 0.0557(3) 0.67798(9) 0.5516(3) 0.0424 1.0000 Uani . . . . . .
C11 C 0.0233(4) 0.65603(12) 0.3595(3) 0.0665 1.0000 Uani . . . . . .
N12 N -0.0623(2) 0.72966(7) 0.5878(2) 0.0413 1.0000 Uani . . . . . .
C13 C -0.0105(4) 0.78236(10) 0.4839(3) 0.0531 1.0000 Uani . . . . . .
Cl1 Cl 0.01904(8) 0.77461(3) 0.97032(7) 0.0532 1.0000 Uani . . . . . .
H13 H 0.6526 0.4440 0.7703 0.1743 1.0000 Uiso R . . . . .
H11 H 0.5180 0.4212 0.9272 0.1738 1.0000 Uiso R . . . . .
H12 H 0.4810 0.4015 0.7268 0.1738 1.0000 Uiso R . . . . .
H31 H 0.1641 0.4430 0.8603 0.1185 1.0000 Uiso R . . . . .
H41 H -0.0436 0.5216 0.8190 0.1099 1.0000 Uiso R . . . . .
H61 H 0.3898 0.6197 0.6260 0.0794 1.0000 Uiso R . . . . .
H71 H 0.5873 0.5425 0.6744 0.0928 1.0000 Uiso R . . . . .
H101 H 0.1851 0.6886 0.5750 0.0647 1.0000 Uiso R . . . . .
H113 H 0.0614 0.6837 0.2815 0.1255 1.0000 Uiso R . . . . .
H111 H -0.1136 0.6459 0.3410 0.1257 1.0000 Uiso R . . . . .
H112 H 0.0862 0.6198 0.3487 0.1262 1.0000 Uiso R . . . . .
H131 H -0.0922 0.8160 0.5233 0.1028 1.0000 Uiso R . . . . .
H133 H 0.1150 0.7937 0.5107 0.1028 1.0000 Uiso R . . . . .
H132 H -0.0304 0.7776 0.3598 0.1028 1.0000 Uiso R . . . . .
H122 H -0.0592 0.7379 0.7163 0.0804 1.0000 Uiso R . . . . .
H121 H -0.1810 0.7202 0.5780 0.0804 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.137(3) 0.0527(16) 0.0725(19) -0.0041(14) -0.0189(19) 0.0343(18)
C2 0.099(2) 0.0483(15) 0.0488(15) -0.0063(11) -0.0116(15) 0.0112(15)
C3 0.108(3) 0.0431(15) 0.077(2) 0.0070(13) -0.0053(18) -0.0088(16)
C4 0.079(2) 0.0506(16) 0.087(2) 0.0122(14) 0.0031(16) -0.0126(15)
C5 0.0565(16) 0.0430(13) 0.0525(14) 0.0014(10) 0.0007(11) -0.0062(11)
C6 0.0593(16) 0.0429(13) 0.0519(14) 0.0040(10) 0.0027(11) 0.0014(11)
C7 0.0716(19) 0.0534(15) 0.0543(15) 0.0008(11) -0.0022(13) 0.0117(13)
C8 0.0475(15) 0.0474(13) 0.0582(15) 0.0024(11) 0.0066(12) -0.0090(11)
O9 0.0596(13) 0.0744(13) 0.1088(16) 0.0265(11) 0.0311(11) 0.0004(10)
C10 0.0371(12) 0.0464(12) 0.0437(12) -0.0014(9) 0.0007(9) 0.0006(10)
C11 0.088(2) 0.0598(16) 0.0520(15) -0.0138(12) -0.0009(14) 0.0148(14)
N12 0.0370(10) 0.0455(10) 0.0413(9) -0.0032(8) 0.0007(7) -0.0019(8)
C13 0.0618(17) 0.0455(14) 0.0521(14) 0.0035(10) 0.0014(12) -0.0032(11)
Cl1 0.0373(3) 0.0808(4) 0.0415(3) -0.0132(3) -0.0028(2) 0.0068(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2052(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
C1 . C2 . 1.505(4) yes
C1 . H13 . 1.000 no
C1 . H11 . 1.002 no
C1 . H12 . 1.014 no
C2 . C3 . 1.385(4) yes
C2 . C7 . 1.387(4) yes
C3 . C4 . 1.386(4) yes
C3 . H31 . 1.035 no
C4 . C5 . 1.396(3) yes
C4 . H41 . 0.928 no
C5 . C6 . 1.386(3) yes
C5 . C8 . 1.481(3) yes
C6 . C7 . 1.387(3) yes
C6 . H61 . 0.934 no
C7 . H71 . 0.982 no
C8 . O9 . 1.223(3) yes
C8 . C10 . 1.517(3) yes
C10 . C11 . 1.523(3) yes
C10 . N12 . 1.482(3) yes
C10 . H101 . 0.967 no
C11 . H113 . 0.904 no
C11 . H111 . 1.010 no
C11 . H112 . 0.949 no
N12 . C13 . 1.485(3) yes
N12 . H122 . 0.970 no
N12 . H121 . 0.875 no
C13 . H131 . 1.014 no
C13 . H133 . 0.949 no
C13 . H132 . 0.935 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
C2 . C1 . H13 . 115.2 no
C2 . C1 . H11 . 114.4 no
H13 . C1 . H11 . 106.7 no
C2 . C1 . H12 . 112.5 no
H13 . C1 . H12 . 104.5 no
H11 . C1 . H12 . 102.2 no
C1 . C2 . C3 . 120.4(3) yes
C1 . C2 . C7 . 121.6(3) yes
C3 . C2 . C7 . 117.9(3) yes
C2 . C3 . C4 . 121.6(3) yes
C2 . C3 . H31 . 112.9 no
C4 . C3 . H31 . 125.5 no
C3 . C4 . C5 . 120.1(3) yes
C3 . C4 . H41 . 113.1 no
C5 . C4 . H41 . 126.7 no
C4 . C5 . C6 . 118.4(2) yes
C4 . C5 . C8 . 118.5(2) yes
C6 . C5 . C8 . 123.1(2) yes
C5 . C6 . C7 . 120.9(2) yes
C5 . C6 . H61 . 125.1 no
C7 . C6 . H61 . 114.0 no
C2 . C7 . C6 . 121.0(3) yes
C2 . C7 . H71 . 116.8 no
C6 . C7 . H71 . 122.1 no
C5 . C8 . O9 . 122.1(2) yes
C5 . C8 . C10 . 118.5(2) yes
O9 . C8 . C10 . 119.3(2) yes
C8 . C10 . C11 . 109.89(19) yes
C8 . C10 . N12 . 108.99(18) yes
C11 . C10 . N12 . 110.92(18) yes
C8 . C10 . H101 . 106.6 no
C11 . C10 . H101 . 112.3 no
N12 . C10 . H101 . 107.9 no
C10 . C11 . H113 . 108.8 no
C10 . C11 . H111 . 109.5 no
H113 . C11 . H111 . 112.0 no
C10 . C11 . H112 . 107.8 no
H113 . C11 . H112 . 114.5 no
H111 . C11 . H112 . 104.1 no
C10 . N12 . C13 . 114.40(18) yes
C10 . N12 . H122 . 109.2 no
C13 . N12 . H122 . 110.4 no
C10 . N12 . H121 . 109.7 no
C13 . N12 . H121 . 114.1 no
H122 . N12 . H121 . 97.8 no
N12 . C13 . H131 . 108.9 no
N12 . C13 . H133 . 110.9 no
H131 . C13 . H133 . 105.9 no
N12 . C13 . H132 . 112.3 no
H131 . C13 . H132 . 107.2 no
H133 . C13 . H132 . 111.4 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/09/11 at 09:34:45
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/09/11 at 09:34:45
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983745'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_I_250K
_oxford_structure_analysis_title '250K in P2(1)/n'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone Hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'


#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 

# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 



_cell_length_a                   7.1314(14)
_cell_length_b                   23.013(5)
_cell_length_c                   7.4180(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.803(2)
_cell_angle_gamma                90
_cell_volume                     1217.3(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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 = C11 H16 Cl1 N1 O1 
# Dc =      1.17 Fooo =    456.00 Mu =      2.85 M =    213.71
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.17 FOOO =    456.00 Mu =      2.85 M =    213.71

_chemical_formula_sum            'C11 H16 Cl1 N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    1736
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25
_cell_measurement_temperature    250

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.285

# Sheldrick geometric approximatio 0.94 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# 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      250
_diffrn_reflns_number            7889
_reflns_number_total             2425
_diffrn_reflns_av_R_equivalents  0.042
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2425 
# Theoretical number of reflections is about 4983 


_diffrn_reflns_theta_min         3.821
_diffrn_reflns_theta_max         26.379
_diffrn_measured_fraction_theta_max 0.973

_diffrn_reflns_theta_full        25.588
_diffrn_measured_fraction_theta_full 0.975


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   4.96
_oxford_diffrn_Wilson_scale      89.86

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

_refine_diff_density_min         -0.34
_refine_diff_density_max         0.31


# 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>-10.0\s(I)
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     0
_refine_ls_number_parameters     127
_oxford_refine_ls_R_factor_ref   0.0771
_refine_ls_wR_factor_ref         0.0900
_refine_ls_goodness_of_fit_ref   0.8468
_refine_ls_shift/su_max          0.0004794
_refine_ls_shift/su_mean         0.0000427


# The values computed from all data 
_oxford_reflns_number_all        2421
_refine_ls_R_factor_all          0.0771
_refine_ls_wR_factor_all         0.0900

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1443
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_gt          0.0857

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5155(4) 0.43690(9) 0.8013(3) 0.0977 1.0000 Uani . . . . . .
C2 C 0.3871(5) 0.48822(9) 0.7689(3) 0.0690 1.0000 Uani . . . . . .
C3 C 0.1981(5) 0.48385(10) 0.8084(3) 0.0842 1.0000 Uani . . . . . .
C4 C 0.0761(4) 0.53010(9) 0.7817(3) 0.0769 1.0000 Uani . . . . . .
C5 C 0.1416(3) 0.58223(8) 0.7115(3) 0.0537 1.0000 Uani . . . . . .
C6 C 0.3305(3) 0.58663(8) 0.6722(2) 0.0556 1.0000 Uani . . . . . .
C7 C 0.4510(3) 0.54027(9) 0.7016(3) 0.0639 1.0000 Uani . . . . . .
C8 C 0.0078(3) 0.63062(8) 0.6840(3) 0.0555 1.0000 Uani . . . . . .
O9 O -0.1425(2) 0.63254(7) 0.7607(2) 0.0879 1.0000 Uani . . . . . .
C10 C 0.0554(3) 0.67825(8) 0.5505(2) 0.0456 1.0000 Uani . . . . . .
C11 C 0.0240(3) 0.65648(9) 0.3585(3) 0.0711 1.0000 Uani . . . . . .
N12 N -0.0621(2) 0.72986(6) 0.58642(18) 0.0454 1.0000 Uani . . . . . .
C13 C -0.0096(3) 0.78257(8) 0.4828(2) 0.0576 1.0000 Uani . . . . . .
Cl1 Cl 0.01921(7) 0.77449(2) 0.96880(6) 0.0579 1.0000 Uani . . . . . .
H13 H 0.6444 0.4479 0.7693 0.1743 1.0000 Uiso R . . . . .
H11 H 0.5098 0.4251 0.9261 0.1738 1.0000 Uiso R . . . . .
H12 H 0.4728 0.4054 0.7258 0.1738 1.0000 Uiso R . . . . .
H31 H 0.1479 0.4488 0.8541 0.1185 1.0000 Uiso R . . . . .
H41 H -0.0519 0.5266 0.8130 0.1099 1.0000 Uiso R . . . . .
H61 H 0.3805 0.6217 0.6248 0.0794 1.0000 Uiso R . . . . .
H71 H 0.5798 0.5437 0.6753 0.0928 1.0000 Uiso R . . . . .
H101 H 0.1815 0.6906 0.5692 0.0647 1.0000 Uiso R . . . . .
H113 H 0.0667 0.6856 0.2776 0.1255 1.0000 Uiso R . . . . .
H111 H -0.1084 0.6479 0.3371 0.1257 1.0000 Uiso R . . . . .
H112 H 0.0914 0.6218 0.3448 0.1262 1.0000 Uiso R . . . . .
H131 H -0.0873 0.8146 0.5190 0.1028 1.0000 Uiso R . . . . .
H133 H 0.1199 0.7923 0.5064 0.1028 1.0000 Uiso R . . . . .
H132 H -0.0255 0.7762 0.3555 0.1028 1.0000 Uiso R . . . . .
H122 H -0.0617 0.7387 0.7078 0.0804 1.0000 Uiso R . . . . .
H121 H -0.1834 0.7210 0.5695 0.0804 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.153(3) 0.0596(14) 0.0796(16) -0.0058(13) -0.0172(17) 0.0393(17)
C2 0.103(2) 0.0512(14) 0.0522(13) -0.0062(10) -0.0128(13) 0.0075(14)
C3 0.121(3) 0.0450(14) 0.0861(17) 0.0087(12) -0.0052(17) -0.0128(15)
C4 0.0824(19) 0.0549(14) 0.0936(17) 0.0116(12) 0.0050(14) -0.0152(14)
C5 0.0590(15) 0.0448(11) 0.0572(12) 0.0019(9) 0.0042(10) -0.0058(10)
C6 0.0642(16) 0.0484(12) 0.0542(12) 0.0049(9) 0.0020(11) 0.0007(11)
C7 0.0742(17) 0.0555(13) 0.0621(13) 0.0014(10) -0.0047(11) 0.0128(12)
C8 0.0483(14) 0.0529(12) 0.0655(13) 0.0023(10) 0.0103(11) -0.0086(11)
O9 0.0633(12) 0.0826(11) 0.1187(13) 0.0302(10) 0.0333(10) 0.0001(9)
C10 0.0399(11) 0.0469(11) 0.0499(11) -0.0022(9) 0.0015(9) 0.0019(9)
C11 0.0910(19) 0.0647(13) 0.0575(13) -0.0178(10) -0.0006(12) 0.0176(12)
N12 0.0415(9) 0.0509(9) 0.0438(8) -0.0048(7) 0.0000(7) -0.0026(8)
C13 0.0665(15) 0.0483(12) 0.0581(12) 0.0037(10) 0.0025(11) -0.0031(11)
Cl1 0.0405(3) 0.0884(4) 0.0447(3) -0.0138(3) -0.00310(19) 0.0075(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3304(4)
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
C1 . C2 . 1.511(3) yes
C1 . H13 . 0.985 no
C1 . H11 . 0.966 no
C1 . H12 . 0.963 no
C2 . C3 . 1.387(4) yes
C2 . C7 . 1.377(3) yes
C3 . C4 . 1.387(3) yes
C3 . H31 . 0.947 no
C4 . C5 . 1.391(3) yes
C4 . H41 . 0.948 no
C5 . C6 . 1.385(3) yes
C5 . C8 . 1.479(3) yes
C6 . C7 . 1.385(3) yes
C6 . H61 . 0.952 no
C7 . H71 . 0.945 no
C8 . O9 . 1.222(2) yes
C8 . C10 . 1.519(2) yes
C10 . C11 . 1.523(3) yes
C10 . N12 . 1.480(2) yes
C10 . H101 . 0.952 no
C11 . H113 . 0.953 no
C11 . H111 . 0.975 no
C11 . H112 . 0.939 no
N12 . C13 . 1.487(2) yes
N12 . H122 . 0.923 no
N12 . H121 . 0.896 no
C13 . H131 . 0.963 no
C13 . H133 . 0.964 no
C13 . H132 . 0.961 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
C2 . C1 . H13 . 109.0 no
C2 . C1 . H11 . 109.8 no
H13 . C1 . H11 . 110.8 no
C2 . C1 . H12 . 108.0 no
H13 . C1 . H12 . 109.9 no
H11 . C1 . H12 . 109.2 no
C1 . C2 . C3 . 119.9(2) yes
C1 . C2 . C7 . 122.3(3) yes
C3 . C2 . C7 . 117.8(2) yes
C2 . C3 . C4 . 121.6(2) yes
C2 . C3 . H31 . 120.7 no
C4 . C3 . H31 . 117.7 no
C3 . C4 . C5 . 120.1(3) yes
C3 . C4 . H41 . 120.2 no
C5 . C4 . H41 . 119.7 no
C4 . C5 . C6 . 118.3(2) yes
C4 . C5 . C8 . 118.8(2) yes
C6 . C5 . C8 . 122.90(18) yes
C5 . C6 . C7 . 120.9(2) yes
C5 . C6 . H61 . 120.7 no
C7 . C6 . H61 . 118.4 no
C6 . C7 . C2 . 121.3(2) yes
C6 . C7 . H71 . 120.4 no
C2 . C7 . H71 . 118.4 no
C5 . C8 . O9 . 122.15(18) yes
C5 . C8 . C10 . 118.93(18) yes
O9 . C8 . C10 . 118.87(18) yes
C8 . C10 . C11 . 109.94(15) yes
C8 . C10 . N12 . 109.25(15) yes
C11 . C10 . N12 . 110.86(15) yes
C8 . C10 . H101 . 109.9 no
C11 . C10 . H101 . 111.1 no
N12 . C10 . H101 . 105.7 no
C10 . C11 . H113 . 108.3 no
C10 . C11 . H111 . 110.4 no
H113 . C11 . H111 . 110.9 no
C10 . C11 . H112 . 108.2 no
H113 . C11 . H112 . 111.2 no
H111 . C11 . H112 . 107.8 no
C10 . N12 . C13 . 114.48(15) yes
C10 . N12 . H122 . 111.0 no
C13 . N12 . H122 . 109.2 no
C10 . N12 . H121 . 109.9 no
C13 . N12 . H121 . 111.3 no
H122 . N12 . H121 . 100.2 no
N12 . C13 . H131 . 109.3 no
N12 . C13 . H133 . 110.0 no
H131 . C13 . H133 . 109.0 no
N12 . C13 . H132 . 110.9 no
H131 . C13 . H132 . 109.4 no
H133 . C13 . H132 . 108.3 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/09/11 at 11:05:05
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/09/11 at 11:05:05
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983746'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_I_275K
_oxford_structure_analysis_title '275K in P2(1)/n'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone Hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'

#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 
# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 


_cell_length_a                   7.1365(14)
_cell_length_b                   23.041(5)
_cell_length_c                   7.4304(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.628(2)
_cell_angle_gamma                90
_cell_volume                     1221.7(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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 = C11 H16 Cl1 N1 O1 
# Dc =      1.16 Fooo =    456.00 Mu =      2.84 M =    213.71
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.16 FOOO =    456.00 Mu =      2.84 M =    213.71

_chemical_formula_sum            'C11 H16 Cl1 N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    1643
_cell_measurement_theta_min      4
_cell_measurement_theta_max      22
_cell_measurement_temperature    275

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.284

# Sheldrick geometric approximatio 0.94 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# 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      275
_diffrn_reflns_number            7911
_reflns_number_total             2431
_diffrn_reflns_av_R_equivalents  0.046
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2431 
# Theoretical number of reflections is about 5001 


_diffrn_reflns_theta_min         3.816
_diffrn_reflns_theta_max         26.379
_diffrn_measured_fraction_theta_max 0.972

_diffrn_reflns_theta_full        25.588
_diffrn_measured_fraction_theta_full 0.975


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   4.96
_oxford_diffrn_Wilson_scale      89.86

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

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.37


# 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>-10.0\s(I)
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     0
_refine_ls_number_parameters     127
_oxford_refine_ls_R_factor_ref   0.0836
_refine_ls_wR_factor_ref         0.0892
_refine_ls_goodness_of_fit_ref   0.8112
_refine_ls_shift/su_max          0.0010839
_refine_ls_shift/su_mean         0.0000372


# The values computed from all data 
_oxford_reflns_number_all        2427
_refine_ls_R_factor_all          0.0836
_refine_ls_wR_factor_all         0.0892

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1378
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_gt          0.0841

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5132(4) 0.43733(9) 0.8011(3) 0.1066 1.0000 Uani . . . . . .
C2 C 0.3848(5) 0.48865(9) 0.7681(3) 0.0752 1.0000 Uani . . . . . .
C3 C 0.1958(5) 0.48434(10) 0.8070(3) 0.0924 1.0000 Uani . . . . . .
C4 C 0.0738(4) 0.53066(10) 0.7801(3) 0.0837 1.0000 Uani . . . . . .
C5 C 0.1399(3) 0.58259(8) 0.7101(3) 0.0594 1.0000 Uani . . . . . .
C6 C 0.3286(3) 0.58685(9) 0.6720(2) 0.0617 1.0000 Uani . . . . . .
C7 C 0.4485(3) 0.54036(9) 0.7016(3) 0.0703 1.0000 Uani . . . . . .
C8 C 0.0072(3) 0.63108(8) 0.6826(3) 0.0602 1.0000 Uani . . . . . .
O9 O -0.1439(2) 0.63288(7) 0.7588(2) 0.0959 1.0000 Uani . . . . . .
C10 C 0.0550(3) 0.67855(8) 0.5497(2) 0.0497 1.0000 Uani . . . . . .
C11 C 0.0250(4) 0.65697(9) 0.3581(3) 0.0779 1.0000 Uani . . . . . .
N12 N -0.0620(2) 0.73015(6) 0.58512(18) 0.0496 1.0000 Uani . . . . . .
C13 C -0.0099(3) 0.78278(8) 0.4819(2) 0.0624 1.0000 Uani . . . . . .
Cl1 Cl 0.01961(7) 0.77441(2) 0.96723(6) 0.0642 1.0000 Uani . . . . . .
H13 H 0.6421 0.4483 0.7691 0.1743 1.0000 Uiso R . . . . .
H11 H 0.5075 0.4255 0.9260 0.1738 1.0000 Uiso R . . . . .
H12 H 0.4705 0.4058 0.7256 0.1738 1.0000 Uiso R . . . . .
H31 H 0.1456 0.4493 0.8527 0.1185 1.0000 Uiso R . . . . .
H41 H -0.0543 0.5271 0.8114 0.1099 1.0000 Uiso R . . . . .
H61 H 0.3786 0.6219 0.6246 0.0794 1.0000 Uiso R . . . . .
H71 H 0.5773 0.5438 0.6753 0.0928 1.0000 Uiso R . . . . .
H101 H 0.1812 0.6909 0.5683 0.0647 1.0000 Uiso R . . . . .
H113 H 0.0677 0.6861 0.2772 0.1255 1.0000 Uiso R . . . . .
H111 H -0.1073 0.6484 0.3368 0.1257 1.0000 Uiso R . . . . .
H112 H 0.0925 0.6223 0.3444 0.1262 1.0000 Uiso R . . . . .
H131 H -0.0876 0.8148 0.5182 0.1028 1.0000 Uiso R . . . . .
H133 H 0.1196 0.7925 0.5055 0.1028 1.0000 Uiso R . . . . .
H132 H -0.0258 0.7764 0.3546 0.1028 1.0000 Uiso R . . . . .
H122 H -0.0616 0.7389 0.7065 0.0804 1.0000 Uiso R . . . . .
H121 H -0.1833 0.7213 0.5682 0.0804 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.166(3) 0.0663(15) 0.0872(17) -0.0038(13) -0.0201(17) 0.0416(18)
C2 0.113(2) 0.0561(15) 0.0565(13) -0.0050(11) -0.0123(14) 0.0070(15)
C3 0.135(3) 0.0488(15) 0.0935(18) 0.0103(12) -0.0047(18) -0.0146(17)
C4 0.088(2) 0.0591(14) 0.1042(18) 0.0139(13) 0.0049(15) -0.0138(14)
C5 0.0633(16) 0.0498(12) 0.0651(13) 0.0019(10) 0.0029(11) -0.0063(11)
C6 0.0691(17) 0.0529(13) 0.0630(12) 0.0063(10) 0.0006(11) -0.0003(12)
C7 0.0796(17) 0.0623(14) 0.0690(14) 0.0026(11) -0.0036(12) 0.0133(13)
C8 0.0501(14) 0.0597(13) 0.0710(14) 0.0010(11) 0.0104(11) -0.0103(11)
O9 0.0695(12) 0.0884(12) 0.1306(14) 0.0327(10) 0.0350(10) -0.0002(9)
C10 0.0418(12) 0.0535(12) 0.0539(11) -0.0019(9) 0.0030(9) 0.0014(9)
C11 0.0982(19) 0.0728(14) 0.0627(13) -0.0181(11) 0.0009(12) 0.0178(13)
N12 0.0436(9) 0.0569(10) 0.0483(8) -0.0044(7) 0.0005(7) -0.0031(8)
C13 0.0713(16) 0.0510(12) 0.0649(12) 0.0058(10) 0.0019(11) -0.0030(11)
Cl1 0.0448(3) 0.0976(4) 0.0502(3) -0.0152(3) -0.0038(2) 0.0082(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3316(4)
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
C1 . C2 . 1.514(3) yes
C1 . H13 . 0.985 no
C1 . H11 . 0.968 no
C1 . H12 . 0.965 no
C2 . C3 . 1.386(4) yes
C2 . C7 . 1.370(3) yes
C3 . C4 . 1.391(4) yes
C3 . H31 . 0.948 no
C4 . C5 . 1.389(3) yes
C4 . H41 . 0.949 no
C5 . C6 . 1.383(3) yes
C5 . C8 . 1.477(3) yes
C6 . C7 . 1.387(3) yes
C6 . H61 . 0.952 no
C7 . H71 . 0.945 no
C8 . O9 . 1.224(2) yes
C8 . C10 . 1.515(2) yes
C10 . C11 . 1.520(3) yes
C10 . N12 . 1.478(2) yes
C10 . H101 . 0.953 no
C11 . H113 . 0.953 no
C11 . H111 . 0.976 no
C11 . H112 . 0.939 no
N12 . C13 . 1.484(2) yes
N12 . H122 . 0.924 no
N12 . H121 . 0.897 no
C13 . H131 . 0.964 no
C13 . H133 . 0.965 no
C13 . H132 . 0.963 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
C2 . C1 . H13 . 109.0 no
C2 . C1 . H11 . 110.1 no
H13 . C1 . H11 . 110.7 no
C2 . C1 . H12 . 107.8 no
H13 . C1 . H12 . 110.0 no
H11 . C1 . H12 . 109.3 no
C1 . C2 . C3 . 119.9(3) yes
C1 . C2 . C7 . 122.3(3) yes
C3 . C2 . C7 . 117.7(2) yes
C2 . C3 . C4 . 121.6(2) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 117.8 no
C3 . C4 . C5 . 120.0(3) yes
C3 . C4 . H41 . 120.2 no
C5 . C4 . H41 . 119.8 no
C4 . C5 . C6 . 118.2(2) yes
C4 . C5 . C8 . 118.9(2) yes
C6 . C5 . C8 . 122.84(18) yes
C5 . C6 . C7 . 120.9(2) yes
C5 . C6 . H61 . 120.4 no
C7 . C6 . H61 . 118.7 no
C6 . C7 . C2 . 121.5(2) yes
C6 . C7 . H71 . 120.1 no
C2 . C7 . H71 . 118.4 no
C5 . C8 . O9 . 121.90(19) yes
C5 . C8 . C10 . 119.16(19) yes
O9 . C8 . C10 . 118.88(19) yes
C8 . C10 . C11 . 110.11(16) yes
C8 . C10 . N12 . 109.42(15) yes
C11 . C10 . N12 . 110.84(15) yes
C8 . C10 . H101 . 109.9 no
C11 . C10 . H101 . 110.9 no
N12 . C10 . H101 . 105.6 no
C10 . C11 . H113 . 108.5 no
C10 . C11 . H111 . 110.2 no
H113 . C11 . H111 . 110.8 no
C10 . C11 . H112 . 108.3 no
H113 . C11 . H112 . 111.3 no
H111 . C11 . H112 . 107.8 no
C10 . N12 . C13 . 114.81(15) yes
C10 . N12 . H122 . 110.8 no
C13 . N12 . H122 . 109.1 no
C10 . N12 . H121 . 109.8 no
C13 . N12 . H121 . 111.1 no
H122 . N12 . H121 . 100.3 no
N12 . C13 . H131 . 109.5 no
N12 . C13 . H133 . 109.9 no
H131 . C13 . H133 . 108.9 no
N12 . C13 . H132 . 110.8 no
H131 . C13 . H132 . 109.3 no
H133 . C13 . H132 . 108.4 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/09/11 at 10:36:59
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/09/11 at 10:36:59
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983747'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a_I_293K
_oxford_structure_analysis_title 'mebr12_0m in P2(1)/n'
_chemical_name_systematic        
"(+-)-4'-methylmethcathinone Hydrochloride, Mephedrone"
_chemical_melting_point          '524 K'

#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 

# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 



_cell_length_a                   7.1345(7)
_cell_length_b                   23.048(3)
_cell_length_c                   7.4330(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.449(6)
_cell_angle_gamma                90
_cell_volume                     1222.2(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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 = C11 H14 Cl1 N1 O1 
# Dc =      1.15 Fooo =    456.00 Mu =      2.83 M =    211.69
# Found Formula = C11 H16 Cl1 N1 O1 
# Dc =      1.16 FOOO =    456.00 Mu =      2.84 M =    213.71

_chemical_formula_sum            'C11 H16 Cl N O'
_chemical_formula_moiety         'C11 H16 N O, Cl'
_chemical_compound_source        ?
_chemical_formula_weight         213.71


_cell_measurement_reflns_used    2732
_cell_measurement_theta_min      3
_cell_measurement_theta_max      22
_cell_measurement_temperature    293

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.284

# Sheldrick geometric approximatio 0.94 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# 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      293
_diffrn_reflns_number            13589
_reflns_number_total             2311
_diffrn_reflns_av_R_equivalents  0.037
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2311 
# Theoretical number of reflections is about 4648 


_diffrn_reflns_theta_min         1.767
_diffrn_reflns_theta_max         25.691
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        25.178
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   4.96
_oxford_diffrn_Wilson_scale      89.86

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

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.29


# 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>-10.0\s(I)
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_number_parameters     127
_oxford_refine_ls_R_factor_ref   0.0810
_refine_ls_wR_factor_ref         0.1403
_refine_ls_goodness_of_fit_ref   1.0185
_refine_ls_shift/su_max          0.0006943
_refine_ls_shift/su_mean         0.0000201


# The values computed from all data 
_oxford_reflns_number_all        2299
_refine_ls_R_factor_all          0.0810
_refine_ls_wR_factor_all         0.1403

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1388
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_gt          0.1109

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.82P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5089(7) 0.43791(17) 0.8017(6) 0.1162 1.0000 Uani . . . . . .
C2 C 0.3819(7) 0.48903(15) 0.7675(5) 0.0815 1.0000 Uani . . . . . .
C3 C 0.1930(8) 0.48492(16) 0.8057(6) 0.0995 1.0000 Uani . . . . . .
C4 C 0.0715(6) 0.53127(16) 0.7786(6) 0.0912 1.0000 Uani . . . . . .
C5 C 0.1383(4) 0.58303(13) 0.7085(4) 0.0657 1.0000 Uani . . . . . .
C6 C 0.3277(4) 0.58721(14) 0.6708(4) 0.0674 1.0000 Uani . . . . . .
C7 C 0.4466(5) 0.54060(15) 0.7011(5) 0.0770 1.0000 Uani . . . . . .
C8 C 0.0059(4) 0.63160(13) 0.6814(4) 0.0658 1.0000 Uani . . . . . .
O9 O -0.1458(4) 0.63324(11) 0.7576(4) 0.1036 1.0000 Uani . . . . . .
C10 C 0.0539(4) 0.67892(12) 0.5489(4) 0.0544 1.0000 Uani . . . . . .
C11 C 0.0264(5) 0.65734(15) 0.3578(5) 0.0841 1.0000 Uani . . . . . .
N12 N -0.0623(3) 0.73030(9) 0.5842(3) 0.0532 1.0000 Uani . . . . . .
C13 C -0.0096(4) 0.78285(13) 0.4809(4) 0.0686 1.0000 Uani . . . . . .
Cl1 Cl 0.01986(10) 0.77430(4) 0.96557(10) 0.0708 1.0000 Uani . . . . . .
H13 H 0.6377 0.4489 0.7697 0.1743 1.0000 Uiso R . . . . .
H11 H 0.5032 0.4261 0.9266 0.1738 1.0000 Uiso R . . . . .
H12 H 0.4662 0.4064 0.7262 0.1738 1.0000 Uiso R . . . . .
H31 H 0.1428 0.4499 0.8513 0.1185 1.0000 Uiso R . . . . .
H41 H -0.0565 0.5277 0.8099 0.1099 1.0000 Uiso R . . . . .
H61 H 0.3777 0.6223 0.6234 0.0794 1.0000 Uiso R . . . . .
H71 H 0.5754 0.5440 0.6747 0.0928 1.0000 Uiso R . . . . .
H101 H 0.1800 0.6913 0.5676 0.0647 1.0000 Uiso R . . . . .
H113 H 0.0691 0.6865 0.2769 0.1255 1.0000 Uiso R . . . . .
H111 H -0.1060 0.6487 0.3364 0.1257 1.0000 Uiso R . . . . .
H112 H 0.0938 0.6226 0.3441 0.1262 1.0000 Uiso R . . . . .
H131 H -0.0873 0.8149 0.5172 0.1028 1.0000 Uiso R . . . . .
H133 H 0.1199 0.7925 0.5045 0.1028 1.0000 Uiso R . . . . .
H132 H -0.0255 0.7764 0.3536 0.1028 1.0000 Uiso R . . . . .
H122 H -0.0619 0.7391 0.7056 0.0804 1.0000 Uiso R . . . . .
H121 H -0.1836 0.7215 0.5673 0.0804 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.183(5) 0.073(3) 0.093(3) -0.003(2) -0.020(3) 0.044(3)
C2 0.112(3) 0.061(2) 0.072(2) -0.0069(17) -0.008(2) 0.010(2)
C3 0.144(4) 0.053(2) 0.101(3) 0.011(2) -0.004(3) -0.014(2)
C4 0.092(3) 0.066(2) 0.115(3) 0.016(2) 0.005(2) -0.018(2)
C5 0.0690(19) 0.0551(18) 0.073(2) 0.0035(15) 0.0066(16) -0.0080(16)
C6 0.072(2) 0.0580(19) 0.072(2) 0.0068(15) 0.0043(16) -0.0014(16)
C7 0.086(2) 0.070(2) 0.075(2) 0.0056(18) -0.0008(18) 0.0129(19)
C8 0.0563(18) 0.0633(19) 0.078(2) 0.0016(16) 0.0118(16) -0.0105(15)
O9 0.0755(16) 0.0948(19) 0.141(2) 0.0350(17) 0.0401(16) 0.0014(14)
C10 0.0444(14) 0.0584(18) 0.0604(17) -0.0017(14) 0.0051(12) -0.0011(13)
C11 0.103(3) 0.077(2) 0.073(2) -0.0173(18) 0.003(2) 0.020(2)
N12 0.0448(12) 0.0605(15) 0.0543(13) -0.0030(11) 0.0016(10) -0.0035(11)
C13 0.074(2) 0.060(2) 0.072(2) 0.0038(16) 0.0038(16) -0.0040(16)
Cl1 0.0476(4) 0.1061(7) 0.0586(5) -0.0152(4) -0.0017(3) 0.0087(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2147(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
C1 . C2 . 1.507(5) yes
C1 . H13 . 0.985 no
C1 . H11 . 0.968 no
C1 . H12 . 0.965 no
C2 . C3 . 1.383(6) yes
C2 . C7 . 1.368(5) yes
C3 . C4 . 1.389(6) yes
C3 . H31 . 0.947 no
C4 . C5 . 1.388(4) yes
C4 . H41 . 0.948 no
C5 . C6 . 1.386(4) yes
C5 . C8 . 1.477(4) yes
C6 . C7 . 1.386(4) yes
C6 . H61 . 0.952 no
C7 . H71 . 0.945 no
C8 . O9 . 1.226(3) yes
C8 . C10 . 1.511(4) yes
C10 . C11 . 1.516(4) yes
C10 . N12 . 1.470(3) yes
C10 . H101 . 0.953 no
C11 . H113 . 0.953 no
C11 . H111 . 0.977 no
C11 . H112 . 0.940 no
N12 . C13 . 1.484(4) yes
N12 . H122 . 0.924 no
N12 . H121 . 0.897 no
C13 . H131 . 0.963 no
C13 . H133 . 0.965 no
C13 . H132 . 0.963 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
C2 . C1 . H13 . 108.6 no
C2 . C1 . H11 . 110.6 no
H13 . C1 . H11 . 110.5 no
C2 . C1 . H12 . 107.6 no
H13 . C1 . H12 . 110.1 no
H11 . C1 . H12 . 109.3 no
C1 . C2 . C3 . 119.8(4) yes
C1 . C2 . C7 . 122.4(4) yes
C3 . C2 . C7 . 117.7(3) yes
C2 . C3 . C4 . 121.7(4) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 118.0 no
C3 . C4 . C5 . 120.0(4) yes
C3 . C4 . H41 . 120.0 no
C5 . C4 . H41 . 120.0 no
C4 . C5 . C6 . 118.3(3) yes
C4 . C5 . C8 . 118.8(3) yes
C6 . C5 . C8 . 122.9(3) yes
C5 . C6 . C7 . 120.7(3) yes
C5 . C6 . H61 . 120.2 no
C7 . C6 . H61 . 119.1 no
C6 . C7 . C2 . 121.6(3) yes
C6 . C7 . H71 . 119.8 no
C2 . C7 . H71 . 118.6 no
C5 . C8 . O9 . 121.8(3) yes
C5 . C8 . C10 . 119.2(3) yes
O9 . C8 . C10 . 119.0(3) yes
C8 . C10 . C11 . 110.2(3) yes
C8 . C10 . N12 . 109.5(2) yes
C11 . C10 . N12 . 111.2(2) yes
C8 . C10 . H101 . 109.9 no
C11 . C10 . H101 . 110.5 no
N12 . C10 . H101 . 105.5 no
C10 . C11 . H113 . 108.7 no
C10 . C11 . H111 . 109.7 no
H113 . C11 . H111 . 110.7 no
C10 . C11 . H112 . 108.6 no
H113 . C11 . H112 . 111.4 no
H111 . C11 . H112 . 107.7 no
C10 . N12 . C13 . 114.8(2) yes
C10 . N12 . H122 . 110.7 no
C13 . N12 . H122 . 109.1 no
C10 . N12 . H121 . 109.7 no
C13 . N12 . H121 . 111.2 no
H122 . N12 . H121 . 100.5 no
N12 . C13 . H131 . 109.4 no
N12 . C13 . H133 . 109.9 no
H131 . C13 . H133 . 108.9 no
N12 . C13 . H132 . 110.8 no
H131 . C13 . H132 . 109.2 no
H133 . C13 . H132 . 108.6 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/09/11 at 11:23:47
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/09/11 at 11:23:47
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983748'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1b_I
_oxford_structure_analysis_title 'MBR1_020412_0m in P2(1)/c'
_chemical_name_systematic        "(+-)-4'-methylmethcathinone Hydrobromide"
_chemical_melting_point          '486 K'


#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 

# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 

#
# of FCF Reflections Below Th(Min) .....          1
# FCF Refl Between THmin & STh/L=  0.600         11


#===============================================================================
#===============================================================================
#-------------------------------------------------------------------------------


#          2
# of FCF Reflections Above STh/L=  0.600         14


#





_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                   5.7804(4)
_cell_length_b                   19.7971(14)
_cell_length_c                   10.5967(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.841(3)
_cell_angle_gamma                90
_cell_volume                     1190.99(14)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C11 H15 Br1 N1 O1 
# Dc =      1.43 Fooo =    528.00 Mu =     34.22 M =    257.15
# Found Formula = C11 H16 Br1 N1 O1 
# Dc =      1.44 FOOO =    528.00 Mu =     34.22 M =    258.16

_chemical_formula_sum            'C11 H16 Br1 N1 O1'
_chemical_formula_moiety         'C11 H16 N O, Br'
_chemical_compound_source        ?
_chemical_formula_weight         258.16


_cell_measurement_reflns_used    5090
_cell_measurement_theta_min      2
_cell_measurement_theta_max      28
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.400

_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    3.422

# Sheldrick geometric approximatio 0.36 0.71 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_T_max  0.71
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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      123
_diffrn_reflns_number            9953
_reflns_number_total             2944
_diffrn_reflns_av_R_equivalents  0.029
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2944 
# Theoretical number of reflections is about 5916 


_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         28.288
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        25.459
_diffrn_measured_fraction_theta_full 0.994


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              26
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   1.89
_oxford_diffrn_Wilson_scale      41.26

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

_refine_diff_density_min         -0.52
_refine_diff_density_max         0.54


# 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>-10.0\s(I)
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_number_parameters     127
_oxford_refine_ls_R_factor_ref   0.0333
_refine_ls_wR_factor_ref         0.0706
_refine_ls_goodness_of_fit_ref   0.9801
_refine_ls_shift/su_max          0.0016962
_refine_ls_shift/su_mean         0.0000374


# The values computed from all data 
_oxford_reflns_number_all        2938
_refine_ls_R_factor_all          0.0333
_refine_ls_wR_factor_all         0.0706

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2500
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_gt          0.0668

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.83P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.6997(4) 0.45288(12) 0.4133(2) 0.0362 1.0000 Uani . . . . . .
C2 C 0.5663(4) 0.49931(11) 0.3126(2) 0.0273 1.0000 Uani . . . . . .
C3 C 0.3371(4) 0.48389(11) 0.2519(2) 0.0271 1.0000 Uani . . . . . .
C4 C 0.2142(4) 0.52694(10) 0.16042(19) 0.0248 1.0000 Uani . . . . . .
C5 C 0.3178(3) 0.58594(10) 0.12508(17) 0.0209 1.0000 Uani . . . . . .
C6 C 0.5485(3) 0.60090(11) 0.1840(2) 0.0257 1.0000 Uani . . . . . .
C7 C 0.6690(4) 0.55806(11) 0.2773(2) 0.0298 1.0000 Uani . . . . . .
C8 C 0.1742(3) 0.63080(10) 0.02824(19) 0.0217 1.0000 Uani . . . . . .
O9 O -0.0352(2) 0.62097(8) -0.00998(17) 0.0354 1.0000 Uani . . . . . .
C10 C 0.2926(3) 0.68892(10) -0.02812(18) 0.0205 1.0000 Uani . . . . . .
C11 C 0.4273(4) 0.66222(14) -0.1276(2) 0.0378 1.0000 Uani . . . . . .
N12 N 0.1051(3) 0.73684(8) -0.08797(15) 0.0207 1.0000 Uani . . . . . .
C13 C 0.1972(4) 0.80026(11) -0.1345(2) 0.0345 1.0000 Uani . . . . . .
Br1 Br -0.18830(3) 0.797321(10) 0.120604(17) 0.0247 1.0000 Uani . . . . . .
H13 H 0.8656 0.4530 0.4101 0.0571 1.0000 Uiso R . . . . .
H11 H 0.6800 0.4669 0.4982 0.0566 1.0000 Uiso R . . . . .
H12 H 0.6403 0.4074 0.3989 0.0567 1.0000 Uiso R . . . . .
H31 H 0.2656 0.4443 0.2727 0.0351 1.0000 Uiso R . . . . .
H41 H 0.0617 0.5167 0.1215 0.0299 1.0000 Uiso R . . . . .
H61 H 0.6241 0.6395 0.1631 0.0320 1.0000 Uiso R . . . . .
H71 H 0.8229 0.5687 0.3164 0.0357 1.0000 Uiso R . . . . .
H101 H 0.3970 0.7129 0.0377 0.0249 1.0000 Uiso R . . . . .
H113 H 0.5151 0.6983 -0.1552 0.0591 1.0000 Uiso R . . . . .
H111 H 0.3200 0.6440 -0.1983 0.0591 1.0000 Uiso R . . . . .
H112 H 0.5326 0.6272 -0.0902 0.0587 1.0000 Uiso R . . . . .
H131 H 0.0708 0.8311 -0.1607 0.0522 1.0000 Uiso R . . . . .
H133 H 0.3089 0.8203 -0.0655 0.0519 1.0000 Uiso R . . . . .
H132 H 0.2727 0.7905 -0.2055 0.0522 1.0000 Uiso R . . . . .
H122 H 0.0102 0.7164 -0.1525 0.0328 1.0000 Uiso R . . . . .
H121 H 0.0156 0.7473 -0.0312 0.0328 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0381(13) 0.0328(13) 0.0338(11) 0.0080(9) -0.0032(9) 0.0041(10)
C2 0.0300(10) 0.0251(11) 0.0255(10) -0.0002(8) 0.0022(8) 0.0064(8)
C3 0.0298(10) 0.0201(10) 0.0304(10) -0.0002(8) 0.0033(8) -0.0015(8)
C4 0.0223(9) 0.0219(10) 0.0288(10) -0.0033(8) 0.0015(8) -0.0013(8)
C5 0.0194(9) 0.0203(9) 0.0221(9) -0.0027(7) 0.0016(7) 0.0021(7)
C6 0.0204(9) 0.0249(11) 0.0307(10) 0.0015(8) 0.0015(8) -0.0019(8)
C7 0.0198(9) 0.0347(12) 0.0316(11) 0.0014(9) -0.0032(8) 0.0013(8)
C8 0.0195(9) 0.0182(9) 0.0266(9) -0.0024(7) 0.0025(7) 0.0020(7)
O9 0.0172(7) 0.0287(9) 0.0558(10) 0.0104(7) -0.0046(6) -0.0040(6)
C10 0.0154(8) 0.0265(10) 0.0187(8) -0.0007(7) 0.0004(7) -0.0003(7)
C11 0.0245(10) 0.0645(17) 0.0254(10) 0.0014(10) 0.0074(8) 0.0155(11)
N12 0.0208(7) 0.0207(8) 0.0202(7) 0.0001(6) 0.0029(6) -0.0005(6)
C13 0.0396(13) 0.0263(12) 0.0355(12) 0.0054(9) 0.0016(10) -0.0080(9)
Br1 0.02096(11) 0.03112(13) 0.02070(11) -0.00562(7) 0.00059(7) 0.00272(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.15822(7)
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
C1 . C2 . 1.507(3) yes
C1 . H13 . 0.966 no
C1 . H11 . 0.969 no
C1 . H12 . 0.965 no
C2 . C3 . 1.393(3) yes
C2 . C7 . 1.389(3) yes
C3 . C4 . 1.382(3) yes
C3 . H31 . 0.932 no
C4 . C5 . 1.396(3) yes
C4 . H41 . 0.923 no
C5 . C6 . 1.394(3) yes
C5 . C8 . 1.487(3) yes
C6 . C7 . 1.387(3) yes
C6 . H61 . 0.927 no
C7 . H71 . 0.932 no
C8 . O9 . 1.218(2) yes
C8 . C10 . 1.518(3) yes
C10 . C11 . 1.518(3) yes
C10 . N12 . 1.489(2) yes
C10 . H101 . 0.958 no
C11 . H113 . 0.954 no
C11 . H111 . 0.949 no
C11 . H112 . 0.958 no
N12 . C13 . 1.484(3) yes
N12 . H122 . 0.890 no
N12 . H121 . 0.889 no
C13 . H131 . 0.952 no
C13 . H133 . 0.965 no
C13 . H132 . 0.958 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
C2 . C1 . H13 . 110.7 no
C2 . C1 . H11 . 110.4 no
H13 . C1 . H11 . 108.9 no
C2 . C1 . H12 . 109.7 no
H13 . C1 . H12 . 108.8 no
H11 . C1 . H12 . 108.3 no
C1 . C2 . C3 . 120.6(2) yes
C1 . C2 . C7 . 120.91(19) yes
C3 . C2 . C7 . 118.48(19) yes
C2 . C3 . C4 . 120.5(2) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 119.5 no
C3 . C4 . C5 . 120.94(18) yes
C3 . C4 . H41 . 120.0 no
C5 . C4 . H41 . 119.0 no
C4 . C5 . C6 . 118.71(18) yes
C4 . C5 . C8 . 118.23(17) yes
C6 . C5 . C8 . 123.04(18) yes
C5 . C6 . C7 . 119.95(19) yes
C5 . C6 . H61 . 121.5 no
C7 . C6 . H61 . 118.6 no
C2 . C7 . C6 . 121.41(19) yes
C2 . C7 . H71 . 119.3 no
C6 . C7 . H71 . 119.2 no
C5 . C8 . O9 . 121.69(18) yes
C5 . C8 . C10 . 119.33(16) yes
O9 . C8 . C10 . 118.95(17) yes
C8 . C10 . C11 . 109.71(18) yes
C8 . C10 . N12 . 107.73(15) yes
C11 . C10 . N12 . 110.67(16) yes
C8 . C10 . H101 . 111.0 no
C11 . C10 . H101 . 110.1 no
N12 . C10 . H101 . 107.6 no
C10 . C11 . H113 . 108.9 no
C10 . C11 . H111 . 109.6 no
H113 . C11 . H111 . 110.5 no
C10 . C11 . H112 . 109.5 no
H113 . C11 . H112 . 109.6 no
H111 . C11 . H112 . 108.8 no
C10 . N12 . C13 . 113.75(16) yes
C10 . N12 . H122 . 109.3 no
C13 . N12 . H122 . 109.8 no
C10 . N12 . H121 . 109.2 no
C13 . N12 . H121 . 108.6 no
H122 . N12 . H121 . 105.8 no
N12 . C13 . H131 . 109.6 no
N12 . C13 . H133 . 109.1 no
H131 . C13 . H133 . 109.0 no
N12 . C13 . H132 . 109.6 no
H131 . C13 . H132 . 109.8 no
H133 . C13 . H132 . 109.8 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
C11 . H112 . O9 1_655 134.20(7) 0.958 2.486 3.228(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 03/04/12 at 09:59:02
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 03/04/12 at 09:59:02
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983749'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1b_II
_oxford_structure_analysis_title 'Mebr2_020412_0m in P2(1)/c'
_chemical_name_systematic        "(+-)-4'-methylmethcathinone Hydrobromide"
_chemical_melting_point          '486 K'

#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 

# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 

#





# of FCF Reflections Above STh/L=  0.600         14


#





_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                   10.8355(19)
_cell_length_b                   10.2030(17)
_cell_length_c                   11.5425(19)
_cell_angle_alpha                90
_cell_angle_beta                 111.839(8)
_cell_angle_gamma                90
_cell_volume                     1184.5(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C11 H14 Br1 N1 O1 
# Dc =      1.44 Fooo =    528.00 Mu =     34.40 M =    256.14
# Found Formula = C11 H16 Br1 N1 O1 
# Dc =      1.45 FOOO =    528.00 Mu =     34.41 M =    258.16

_chemical_formula_sum            'C11 H16 Br1 N1 O1'
_chemical_formula_moiety         'C11 H16 N O, Br'
_chemical_compound_source        ?
_chemical_formula_weight         258.16


_cell_measurement_reflns_used    6653
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    123

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    3.441

# Sheldrick geometric approximatio 0.81 0.84 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.84
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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      123
_diffrn_reflns_number            14238
_reflns_number_total             2426
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2426 
# Theoretical number of reflections is about 4872 


_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         26.426
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        25.897
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -13
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   1.57
_oxford_diffrn_Wilson_scale      6.44

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

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.40


# 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>-10.0\s(I)
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     0
_refine_ls_number_parameters     127
_oxford_refine_ls_R_factor_ref   0.0257
_refine_ls_wR_factor_ref         0.0476
_refine_ls_goodness_of_fit_ref   0.9980
_refine_ls_shift/su_max          0.0007645
_refine_ls_shift/su_mean         0.0000433


# The values computed from all data 
_oxford_reflns_number_all        2417
_refine_ls_R_factor_all          0.0257
_refine_ls_wR_factor_all         0.0476

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2105
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_gt          0.0446

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 0.58P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.3274(2) 0.7580(2) 0.3586(2) 0.0420 1.0000 Uani . . . . . .
C2 C 0.43532(19) 0.73267(19) 0.48483(17) 0.0278 1.0000 Uani . . . . . .
C3 C 0.43048(19) 0.62381(19) 0.55574(18) 0.0324 1.0000 Uani . . . . . .
C4 C 0.53067(19) 0.59784(18) 0.66931(17) 0.0277 1.0000 Uani . . . . . .
C5 C 0.64015(17) 0.68107(16) 0.71644(16) 0.0215 1.0000 Uani . . . . . .
C6 C 0.64497(18) 0.79193(17) 0.64668(17) 0.0243 1.0000 Uani . . . . . .
C7 C 0.54356(18) 0.81632(18) 0.53262(17) 0.0266 1.0000 Uani . . . . . .
C8 C 0.74953(17) 0.64662(16) 0.83611(16) 0.0205 1.0000 Uani . . . . . .
O9 O 0.75133(13) 0.54474(12) 0.89183(12) 0.0276 1.0000 Uani . . . . . .
C10 C 0.86214(18) 0.74522(15) 0.89060(16) 0.0191 1.0000 Uani . . . . . .
C11 C 0.81855(19) 0.85693(17) 0.95440(17) 0.0273 1.0000 Uani . . . . . .
N12 N 0.97942(14) 0.67461(13) 0.98015(12) 0.0195 1.0000 Uani . . . . . .
C13 C 1.09916(19) 0.75726(16) 1.04027(17) 0.0257 1.0000 Uani . . . . . .
Br1 Br 1.015410(18) 0.487032(15) 0.768028(15) 0.0221 1.0000 Uani . . . . . .
H13 H 0.3620 0.7737 0.2958 0.0645 1.0000 Uiso R . . . . .
H11 H 0.2762 0.8332 0.3642 0.0641 1.0000 Uiso R . . . . .
H12 H 0.2656 0.6870 0.3323 0.0619 1.0000 Uiso R . . . . .
H31 H 0.3574 0.5652 0.5241 0.0393 1.0000 Uiso R . . . . .
H41 H 0.5287 0.5218 0.7138 0.0349 1.0000 Uiso R . . . . .
H61 H 0.7182 0.8496 0.6767 0.0299 1.0000 Uiso R . . . . .
H71 H 0.5504 0.8901 0.4872 0.0333 1.0000 Uiso R . . . . .
H101 H 0.8904 0.7790 0.8266 0.0213 1.0000 Uiso R . . . . .
H113 H 0.8855 0.9219 0.9800 0.0399 1.0000 Uiso R . . . . .
H111 H 0.8007 0.8247 1.0247 0.0398 1.0000 Uiso R . . . . .
H112 H 0.7395 0.8931 0.8970 0.0411 1.0000 Uiso R . . . . .
H131 H 1.1724 0.6992 1.0757 0.0375 1.0000 Uiso R . . . . .
H133 H 1.0852 0.8144 1.1011 0.0355 1.0000 Uiso R . . . . .
H132 H 1.1138 0.8073 0.9775 0.0352 1.0000 Uiso R . . . . .
H122 H 0.9997 0.6149 0.9364 0.0283 1.0000 Uiso R . . . . .
H121 H 0.9594 0.6347 1.0381 0.0306 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0271(12) 0.0615(15) 0.0331(12) 0.0102(10) 0.0062(10) -0.0039(10)
C2 0.0206(10) 0.0383(11) 0.0256(10) 0.0022(8) 0.0097(8) 0.0025(8)
C3 0.0265(11) 0.0380(11) 0.0333(11) -0.0020(8) 0.0120(9) -0.0094(9)
C4 0.0306(11) 0.0267(10) 0.0275(10) 0.0018(7) 0.0128(9) -0.0045(8)
C5 0.0247(10) 0.0214(9) 0.0221(9) -0.0025(7) 0.0129(8) 0.0005(7)
C6 0.0246(10) 0.0217(9) 0.0266(10) -0.0006(7) 0.0097(8) -0.0006(8)
C7 0.0268(10) 0.0257(10) 0.0294(10) 0.0044(7) 0.0129(8) 0.0032(8)
C8 0.0272(10) 0.0182(9) 0.0211(9) -0.0033(7) 0.0149(8) 0.0004(7)
O9 0.0358(8) 0.0204(6) 0.0274(7) 0.0037(5) 0.0127(6) -0.0034(5)
C10 0.0251(10) 0.0153(8) 0.0174(8) 0.0012(6) 0.0084(7) 0.0004(7)
C11 0.0333(11) 0.0193(9) 0.0293(10) -0.0059(7) 0.0118(9) 0.0016(8)
N12 0.0292(9) 0.0152(7) 0.0157(8) 0.0004(5) 0.0100(7) 0.0013(6)
C13 0.0294(11) 0.0212(9) 0.0225(9) -0.0002(7) 0.0052(8) -0.0002(7)
Br1 0.03229(11) 0.01867(10) 0.01680(10) 0.00065(6) 0.01092(7) 0.00410(7)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.13444(4)
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
C1 . C2 . 1.513(3) yes
C1 . H13 . 0.945 no
C1 . H11 . 0.963 no
C1 . H12 . 0.956 no
C2 . C3 . 1.392(3) yes
C2 . C7 . 1.388(3) yes
C3 . C4 . 1.382(3) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.394(2) yes
C4 . H41 . 0.935 no
C5 . C6 . 1.401(2) yes
C5 . C8 . 1.489(2) yes
C6 . C7 . 1.388(3) yes
C6 . H61 . 0.944 no
C7 . H71 . 0.935 no
C8 . O9 . 1.219(2) yes
C8 . C10 . 1.525(2) yes
C10 . C11 . 1.524(2) yes
C10 . N12 . 1.492(2) yes
C10 . H101 . 0.962 no
C11 . H113 . 0.945 no
C11 . H111 . 0.959 no
C11 . H112 . 0.941 no
N12 . C13 . 1.485(2) yes
N12 . H122 . 0.870 no
N12 . H121 . 0.876 no
C13 . H131 . 0.952 no
C13 . H133 . 0.967 no
C13 . H132 . 0.947 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
C2 . C1 . H13 . 112.4 no
C2 . C1 . H11 . 109.3 no
H13 . C1 . H11 . 108.6 no
C2 . C1 . H12 . 112.1 no
H13 . C1 . H12 . 108.4 no
H11 . C1 . H12 . 105.8 no
C1 . C2 . C3 . 121.16(18) yes
C1 . C2 . C7 . 120.92(18) yes
C3 . C2 . C7 . 117.90(17) yes
C2 . C3 . C4 . 121.51(18) yes
C2 . C3 . H31 . 119.0 no
C4 . C3 . H31 . 119.5 no
C3 . C4 . C5 . 120.51(17) yes
C3 . C4 . H41 . 120.6 no
C5 . C4 . H41 . 118.8 no
C4 . C5 . C6 . 118.41(16) yes
C4 . C5 . C8 . 119.08(15) yes
C6 . C5 . C8 . 122.47(16) yes
C5 . C6 . C7 . 120.30(17) yes
C5 . C6 . H61 . 119.9 no
C7 . C6 . H61 . 119.8 no
C2 . C7 . C6 . 121.36(17) yes
C2 . C7 . H71 . 120.2 no
C6 . C7 . H71 . 118.4 no
C5 . C8 . O9 . 122.80(16) yes
C5 . C8 . C10 . 117.73(14) yes
O9 . C8 . C10 . 119.46(16) yes
C8 . C10 . C11 . 110.39(15) yes
C8 . C10 . N12 . 108.17(13) yes
C11 . C10 . N12 . 111.32(14) yes
C8 . C10 . H101 . 110.7 no
C11 . C10 . H101 . 110.3 no
N12 . C10 . H101 . 105.8 no
C10 . C11 . H113 . 109.6 no
C10 . C11 . H111 . 110.4 no
H113 . C11 . H111 . 110.4 no
C10 . C11 . H112 . 108.5 no
H113 . C11 . H112 . 109.7 no
H111 . C11 . H112 . 108.2 no
C10 . N12 . C13 . 114.87(13) yes
C10 . N12 . H122 . 105.7 no
C13 . N12 . H122 . 107.7 no
C10 . N12 . H121 . 111.4 no
C13 . N12 . H121 . 109.1 no
H122 . N12 . H121 . 107.8 no
N12 . C13 . H131 . 106.9 no
N12 . C13 . H133 . 109.6 no
H131 . C13 . H133 . 113.2 no
N12 . C13 . H132 . 108.3 no
H131 . C13 . H132 . 108.3 no
H133 . C13 . H132 . 110.3 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 06/07/12 at 09:37:51
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 06/07/12 at 09:37:51
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983750'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1c_3070
_oxford_structure_analysis_title 'adio1 in P2(1)/c'
_chemical_name_systematic        
"30:70 (+-)-4'-methylmethcathinone hydrochloride hydrobromide salt solution"
_chemical_melting_point          '493 K'

#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 




_cell_length_a                   10.2017(6)
_cell_length_b                   22.3376(13)
_cell_length_c                   10.5639(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.157(3)
_cell_angle_gamma                90
_cell_volume                     2407.3(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C9 H18 Br1 Cl1 N1 O1 
# Dc =      1.50 Fooo =   1015.46 Mu =     36.04 M =    543.21
# Found Formula = C11 H16 Br0.72 Cl0.28 N1 O1 
# Dc =      1.36 FOOO =   1015.46 Mu =     25.14 M =    491.29

_chemical_formula_sum            'C11 H16 Br0.72 Cl0.28 N O'
_chemical_formula_moiety         'C11 H16 N O,  0.72(Br),  0.28(Cl)'
_chemical_compound_source        ?
_chemical_formula_weight         245.64


_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    123

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1015.460
_exptl_absorpt_coefficient_mu    2.514

# Sheldrick geometric approximatio 0.90 0.93 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.93
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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    'USER DEFINED STRUCTURE SOLUTION'
_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      123
_diffrn_reflns_number            4964
_reflns_number_total             4964
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4964 
# Theoretical number of reflections is about 9963 


_diffrn_reflns_theta_min         1.996
_diffrn_reflns_theta_max         26.484
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        26.484
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.03
_oxford_diffrn_Wilson_scale      229.13

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

_refine_diff_density_min         -0.50
_refine_diff_density_max         0.59


# 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>-10.0\s(I)
_refine_ls_number_reflns         4948
_refine_ls_number_restraints     0
_refine_ls_number_parameters     263
_oxford_refine_ls_R_factor_ref   0.0399
_refine_ls_wR_factor_ref         0.0701
_refine_ls_goodness_of_fit_ref   1.0075
_refine_ls_shift/su_max          0.0030110
_refine_ls_shift/su_mean         0.0001997


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4948
_refine_ls_R_factor_all          0.0399
_refine_ls_wR_factor_all         0.0701

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4051
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_gt          0.0628

# 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 1.88P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.5985(2) -0.08191(11) 0.4703(3) 0.0437 1.0000 Uani . . . . . .
C2 C 0.6672(2) -0.02473(10) 0.5066(2) 0.0320 1.0000 Uani . . . . . .
C3 C 0.7033(2) -0.01399(10) 0.6321(2) 0.0346 1.0000 Uani . . . . . .
C4 C 0.7679(2) 0.0381(1) 0.6650(2) 0.0307 1.0000 Uani . . . . . .
C5 C 0.79883(19) 0.08087(9) 0.5746(2) 0.0250 1.0000 Uani . . . . . .
C6 C 0.7608(2) 0.07069(10) 0.4485(2) 0.0291 1.0000 Uani . . . . . .
C7 C 0.6952(2) 0.01866(10) 0.4168(2) 0.0333 1.0000 Uani . . . . . .
C8 C 0.87248(19) 0.13493(9) 0.61449(19) 0.0245 1.0000 Uani . . . . . .
O9 O 0.88742(16) 0.14770(7) 0.72630(14) 0.0349 1.0000 Uani . . . . . .
C10 C 0.93783(19) 0.17336(9) 0.51412(19) 0.0238 1.0000 Uani . . . . . .
C11 C 1.0611(2) 0.14280(10) 0.4669(2) 0.0348 1.0000 Uani . . . . . .
N12 N 0.97031(16) 0.23273(7) 0.57027(16) 0.0237 1.0000 Uani . . . . . .
C13 C 0.9929(2) 0.28033(10) 0.4746(2) 0.0327 1.0000 Uani . . . . . .
C14 C 0.0203(2) 0.55713(10) 0.3294(2) 0.0328 1.0000 Uani . . . . . .
C15 C 0.1217(2) 0.51349(9) 0.37594(19) 0.0262 1.0000 Uani . . . . . .
C16 C 0.2176(2) 0.53176(10) 0.4619(2) 0.0322 1.0000 Uani . . . . . .
C17 C 0.3083(2) 0.49166(10) 0.5087(2) 0.0317 1.0000 Uani . . . . . .
C18 C 0.30858(19) 0.43224(9) 0.4688(2) 0.0260 1.0000 Uani . . . . . .
C19 C 0.2153(2) 0.41393(9) 0.3797(2) 0.0278 1.0000 Uani . . . . . .
C20 C 0.1225(2) 0.45440(10) 0.3358(2) 0.0296 1.0000 Uani . . . . . .
C21 C 0.4034(2) 0.39018(9) 0.5272(2) 0.0286 1.0000 Uani . . . . . .
O22 O 0.45525(17) 0.40076(7) 0.62901(16) 0.0440 1.0000 Uani . . . . . .
C23 C 0.4416(2) 0.33366(9) 0.4553(2) 0.0264 1.0000 Uani . . . . . .
C24 C 0.5482(2) 0.34842(11) 0.3600(2) 0.0362 1.0000 Uani . . . . . .
N25 N 0.48732(17) 0.28875(7) 0.54969(17) 0.0270 1.0000 Uani . . . . . .
C26 C 0.5228(2) 0.22981(10) 0.4941(2) 0.0353 1.0000 Uani . . . . . .
Cl20 Cl 0.247310(10) 0.251263(10) 0.219979(10) 0.2605 0.275(4) Uani . . P . . .
Br21 Br 0.246028(10) 0.251160(10) 0.218257(10) 0.0268 0.725(4) Uani . . P . . .
Cl10 Cl 0.742480(11) 0.299018(11) 0.715047(11) 0.2064 0.288(4) Uani . . P . . .
Br11 Br 0.745392(11) 0.301046(11) 0.717231(11) 0.0213 0.712(4) Uani . . P . . .
H13 H 0.5194 -0.0725 0.4269 0.0643 1.0000 Uiso R . . . . .
H11 H 0.6534 -0.1060 0.4159 0.0636 1.0000 Uiso R . . . . .
H12 H 0.5795 -0.1032 0.5465 0.0647 1.0000 Uiso R . . . . .
H31 H 0.6829 -0.0424 0.6950 0.0399 1.0000 Uiso R . . . . .
H41 H 0.7893 0.0448 0.7518 0.0349 1.0000 Uiso R . . . . .
H61 H 0.7797 0.1007 0.3850 0.0346 1.0000 Uiso R . . . . .
H71 H 0.6684 0.0106 0.3304 0.0379 1.0000 Uiso R . . . . .
H101 H 0.8773 0.1796 0.4430 0.0273 1.0000 Uiso R . . . . .
H113 H 1.1007 0.1650 0.3980 0.0496 1.0000 Uiso R . . . . .
H111 H 1.1225 0.1408 0.5347 0.0502 1.0000 Uiso R . . . . .
H112 H 1.0418 0.1026 0.4409 0.0496 1.0000 Uiso R . . . . .
H131 H 1.0103 0.3178 0.5170 0.0473 1.0000 Uiso R . . . . .
H133 H 1.0657 0.2702 0.4210 0.0476 1.0000 Uiso R . . . . .
H132 H 0.9162 0.2832 0.4245 0.0483 1.0000 Uiso R . . . . .
H142 H -0.0176 0.5428 0.2510 0.0479 1.0000 Uiso R . . . . .
H141 H 0.0593 0.5963 0.3150 0.0483 1.0000 Uiso R . . . . .
H143 H -0.0488 0.5606 0.3902 0.0479 1.0000 Uiso R . . . . .
H161 H 0.2198 0.5731 0.4892 0.0377 1.0000 Uiso R . . . . .
H171 H 0.3719 0.5041 0.5680 0.0371 1.0000 Uiso R . . . . .
H191 H 0.2140 0.3732 0.3513 0.0316 1.0000 Uiso R . . . . .
H201 H 0.0569 0.4418 0.2772 0.0335 1.0000 Uiso R . . . . .
H231 H 0.3651 0.3175 0.4125 0.0304 1.0000 Uiso R . . . . .
H242 H 0.5666 0.3137 0.3096 0.0524 1.0000 Uiso R . . . . .
H241 H 0.6273 0.3609 0.4030 0.0536 1.0000 Uiso R . . . . .
H243 H 0.5166 0.3805 0.3067 0.0531 1.0000 Uiso R . . . . .
H262 H 0.5431 0.2015 0.5611 0.0526 1.0000 Uiso R . . . . .
H263 H 0.5985 0.2345 0.4408 0.0524 1.0000 Uiso R . . . . .
H261 H 0.4478 0.2159 0.4438 0.0531 1.0000 Uiso R . . . . .
H122 H 0.9048 0.2445 0.6200 0.0332 1.0000 Uiso R . . . . .
H252 H 0.4213 0.2814 0.6047 0.0391 1.0000 Uiso R . . . . .
H121 H 1.0424 0.2287 0.6180 0.0342 1.0000 Uiso R . . . . .
H251 H 0.5549 0.3036 0.5940 0.0385 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0386(13) 0.0327(13) 0.0597(18) -0.0097(12) 0.0014(12) -0.0059(11)
C2 0.0261(11) 0.0283(12) 0.0416(13) -0.0064(10) 0.0043(9) -0.0001(9)
C3 0.0371(13) 0.0270(11) 0.0395(13) 0.0061(10) -0.0001(10) -0.0025(10)
C4 0.0355(12) 0.0278(11) 0.0287(12) 0.0037(9) -0.0032(9) -0.0017(9)
C5 0.0258(10) 0.0248(11) 0.0245(11) -0.0015(9) 0.0011(8) 0.0005(8)
C6 0.0309(11) 0.0336(12) 0.0229(11) -0.0022(9) 0.0022(9) -0.0049(9)
C7 0.0302(11) 0.0413(13) 0.0285(12) -0.0098(10) 0.0055(9) -0.0069(10)
C8 0.0263(10) 0.0246(10) 0.0224(11) 0.0008(8) -0.0024(8) 0.0030(8)
O9 0.0576(10) 0.0273(8) 0.0198(8) 0.0003(6) -0.0033(7) -0.0058(7)
C10 0.0260(10) 0.0265(11) 0.0188(10) -0.0032(8) -0.0041(8) -0.0016(8)
C11 0.0318(12) 0.0349(13) 0.0378(13) -0.0115(10) 0.0068(10) -0.0027(10)
N12 0.0247(9) 0.0250(9) 0.0215(9) 0.0001(7) -0.0010(7) 0.0003(7)
C13 0.0419(13) 0.0286(11) 0.0277(12) 0.0063(10) 0.0068(10) -0.0018(10)
C14 0.0354(12) 0.0283(12) 0.0347(13) 0.0047(10) 0.0004(10) -0.0006(9)
C15 0.0286(11) 0.0259(11) 0.0242(11) 0.0035(9) 0.0046(8) -0.0024(9)
C16 0.0345(12) 0.0241(11) 0.0379(13) -0.0043(10) -0.0011(10) -0.0020(9)
C17 0.0310(12) 0.0284(11) 0.0358(13) -0.0063(10) -0.0063(9) -0.0024(9)
C18 0.0251(10) 0.0266(11) 0.0263(11) -0.0033(9) 0.0034(8) -0.0017(8)
C19 0.0311(11) 0.0232(11) 0.0289(12) -0.0028(9) 0.0004(9) -0.0040(9)
C20 0.0302(11) 0.0308(11) 0.0279(12) -0.0009(9) -0.0036(9) -0.0017(9)
C21 0.0291(11) 0.0273(11) 0.0292(12) -0.0059(9) -0.0005(9) -0.0023(9)
O22 0.0542(11) 0.0410(10) 0.0368(10) -0.0155(8) -0.0185(8) 0.0132(8)
C23 0.0287(11) 0.0249(11) 0.0256(11) -0.0030(9) -0.0054(8) 0.0000(8)
C24 0.0445(13) 0.0330(12) 0.0310(12) 0.0015(10) 0.0067(10) 0.0041(10)
N25 0.0282(9) 0.0262(9) 0.0266(10) -0.0019(7) 0.0000(7) -0.0002(7)
C26 0.0452(14) 0.0259(12) 0.0346(13) -0.0024(10) -0.0004(10) 0.0059(10)
Cl20 0.34(3) 0.210(13) 0.233(17) -0.008(7) -0.222(19) 0.009(8)
Br21 0.0169(2) 0.0424(3) 0.0210(2) -0.00703(16) 0.00058(16) 0.00320(14)
Cl10 0.253(18) 0.179(11) 0.187(13) -0.018(6) -0.173(13) -0.012(6)
Br11 0.0170(2) 0.0273(3) 0.0196(2) -0.00392(16) -0.00048(17) 0.00151(14)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.08900(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
C1 . C2 . 1.506(3) yes
C1 . H13 . 0.951 no
C1 . H11 . 0.968 no
C1 . H12 . 0.955 no
C2 . C3 . 1.396(3) yes
C2 . C7 . 1.386(3) yes
C3 . C4 . 1.381(3) yes
C3 . H31 . 0.942 no
C4 . C5 . 1.388(3) yes
C4 . H41 . 0.954 no
C5 . C6 . 1.405(3) yes
C5 . C8 . 1.483(3) yes
C6 . C7 . 1.382(3) yes
C6 . H61 . 0.968 no
C7 . H71 . 0.969 no
C8 . O9 . 1.224(2) yes
C8 . C10 . 1.520(3) yes
C10 . C11 . 1.516(3) yes
C10 . N12 . 1.490(2) yes
C10 . H101 . 0.981 no
C11 . H113 . 0.969 no
C11 . H111 . 0.951 no
C11 . H112 . 0.960 no
N12 . C13 . 1.485(3) yes
N12 . H122 . 0.891 no
N12 . H121 . 0.896 no
C13 . H131 . 0.966 no
C13 . H133 . 0.962 no
C13 . H132 . 0.946 no
C14 . C15 . 1.503(3) yes
C14 . H142 . 0.967 no
C14 . H141 . 0.972 no
C14 . H143 . 0.958 no
C15 . C16 . 1.394(3) yes
C15 . C20 . 1.386(3) yes
C16 . C17 . 1.378(3) yes
C16 . H161 . 0.967 no
C17 . C18 . 1.393(3) yes
C17 . H171 . 0.943 no
C18 . C19 . 1.398(3) yes
C18 . C21 . 1.482(3) yes
C19 . C20 . 1.388(3) yes
C19 . H191 . 0.958 no
C20 . H201 . 0.954 no
C21 . O22 . 1.221(3) yes
C21 . C23 . 1.524(3) yes
C23 . C24 . 1.520(3) yes
C23 . N25 . 1.488(3) yes
C23 . H231 . 0.970 no
C24 . H242 . 0.960 no
C24 . H241 . 0.966 no
C24 . H243 . 0.965 no
N25 . C26 . 1.487(3) yes
N25 . H252 . 0.906 no
N25 . H251 . 0.896 no
C26 . H262 . 0.970 no
C26 . H263 . 0.963 no
C26 . H261 . 0.981 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
C2 . C1 . H13 . 109.3 no
C2 . C1 . H11 . 110.7 no
H13 . C1 . H11 . 109.2 no
C2 . C1 . H12 . 107.7 no
H13 . C1 . H12 . 110.0 no
H11 . C1 . H12 . 110.0 no
C1 . C2 . C3 . 120.6(2) yes
C1 . C2 . C7 . 121.0(2) yes
C3 . C2 . C7 . 118.4(2) yes
C2 . C3 . C4 . 120.5(2) yes
C2 . C3 . H31 . 119.8 no
C4 . C3 . H31 . 119.7 no
C3 . C4 . C5 . 121.1(2) yes
C3 . C4 . H41 . 118.8 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 118.56(19) yes
C4 . C5 . C8 . 118.80(19) yes
C6 . C5 . C8 . 122.63(19) yes
C5 . C6 . C7 . 119.9(2) yes
C5 . C6 . H61 . 119.4 no
C7 . C6 . H61 . 120.8 no
C2 . C7 . C6 . 121.5(2) yes
C2 . C7 . H71 . 117.1 no
C6 . C7 . H71 . 121.3 no
C5 . C8 . O9 . 121.69(19) yes
C5 . C8 . C10 . 119.01(17) yes
O9 . C8 . C10 . 119.20(18) yes
C8 . C10 . C11 . 109.94(17) yes
C8 . C10 . N12 . 108.82(16) yes
C11 . C10 . N12 . 110.38(16) yes
C8 . C10 . H101 . 109.7 no
C11 . C10 . H101 . 109.4 no
N12 . C10 . H101 . 108.5 no
C10 . C11 . H113 . 111.4 no
C10 . C11 . H111 . 108.5 no
H113 . C11 . H111 . 108.3 no
C10 . C11 . H112 . 110.2 no
H113 . C11 . H112 . 110.4 no
H111 . C11 . H112 . 107.8 no
C10 . N12 . C13 . 113.66(16) yes
C10 . N12 . H122 . 109.4 no
C13 . N12 . H122 . 107.9 no
C10 . N12 . H121 . 108.4 no
C13 . N12 . H121 . 109.1 no
H122 . N12 . H121 . 108.3 no
N12 . C13 . H131 . 109.5 no
N12 . C13 . H133 . 110.7 no
H131 . C13 . H133 . 109.7 no
N12 . C13 . H132 . 107.4 no
H131 . C13 . H132 . 110.6 no
H133 . C13 . H132 . 109.0 no
C15 . C14 . H142 . 109.8 no
C15 . C14 . H141 . 110.6 no
H142 . C14 . H141 . 109.0 no
C15 . C14 . H143 . 109.9 no
H142 . C14 . H143 . 108.0 no
H141 . C14 . H143 . 109.5 no
C14 . C15 . C16 . 120.29(19) yes
C14 . C15 . C20 . 121.47(19) yes
C16 . C15 . C20 . 118.2(2) yes
C15 . C16 . C17 . 120.8(2) yes
C15 . C16 . H161 . 119.3 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . C18 . 120.9(2) yes
C16 . C17 . H171 . 120.4 no
C18 . C17 . H171 . 118.8 no
C17 . C18 . C19 . 118.74(19) yes
C17 . C18 . C21 . 118.71(19) yes
C19 . C18 . C21 . 122.48(19) yes
C18 . C19 . C20 . 119.77(19) yes
C18 . C19 . H191 . 119.8 no
C20 . C19 . H191 . 120.4 no
C19 . C20 . C15 . 121.5(2) yes
C19 . C20 . H201 . 120.1 no
C15 . C20 . H201 . 118.4 no
C18 . C21 . O22 . 121.67(19) yes
C18 . C21 . C23 . 119.05(18) yes
O22 . C21 . C23 . 119.22(19) yes
C21 . C23 . C24 . 109.55(17) yes
C21 . C23 . N25 . 107.75(17) yes
C24 . C23 . N25 . 111.49(17) yes
C21 . C23 . H231 . 109.5 no
C24 . C23 . H231 . 110.4 no
N25 . C23 . H231 . 108.2 no
C23 . C24 . H242 . 109.5 no
C23 . C24 . H241 . 110.4 no
H242 . C24 . H241 . 109.2 no
C23 . C24 . H243 . 107.9 no
H242 . C24 . H243 . 110.0 no
H241 . C24 . H243 . 109.8 no
C23 . N25 . C26 . 114.12(17) yes
C23 . N25 . H252 . 108.6 no
C26 . N25 . H252 . 106.0 no
C23 . N25 . H251 . 109.9 no
C26 . N25 . H251 . 110.3 no
H252 . N25 . H251 . 107.7 no
N25 . C26 . H262 . 109.9 no
N25 . C26 . H263 . 109.3 no
H262 . C26 . H263 . 109.1 no
N25 . C26 . H261 . 107.7 no
H262 . C26 . H261 . 110.7 no
H263 . C26 . H261 . 110.1 no


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 21/01/14 at 19:44:24
#
#LIST     12                                                                    
BLOCK SCALE X'S U'S 
EQUIV CL(10, X'S) BR(11, X'S) 
EQUIV CL(20, X'S) BR(21, X'S) 
EQUIV CL(10, OCC) BR(11, OCC) 
WEIGHT -1 BR(11,OCC) 
EQUIV CL(20, OCC) BR(21, OCC) 
WEIGHT -1 BR(21,OCC) 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE N   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 263,X'S) H   ( 261,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 21/01/14 at 19:44:24
#
#LIST     16                                                                    
NO 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983751'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1c_6040
_oxford_structure_analysis_title 'mo_123k_0m in P2(1)/c'
_chemical_name_systematic        
"60:40 (+-)-4'-methylmethcathinone hydrochloride hydrobromide salt solution"
_chemical_melting_point          '494 K'

#looking for refcif 



# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 





#

_cell_length_a                   10.1409(11)
_cell_length_b                   22.488(3)
_cell_length_c                   10.4979(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.359(8)
_cell_angle_gamma                90
_cell_volume                     2394.0(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C7.33 H10.67 Br0.67 Cl0.67 N0.67 O0.67 
# Dc =      1.63 Fooo =    970.11 Mu =     36.31 M =    587.22
# Found Formula = C7.33 H10.67 Br0.27 Cl0.40 N0.67 O0.67 
# Dc =      1.29 FOOO =    970.11 Mu =     15.47 M =    463.29

_chemical_formula_sum            'C11 H16 Br0.40 Cl0.60 N O'
_chemical_formula_moiety         'C11 H16 N O,  0.4(Br),  0.6(Cl)'
_chemical_compound_source        ?
_chemical_formula_weight         231.63


_cell_measurement_reflns_used    5093
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    123

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.010
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_max          0.100

_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             970.105
_exptl_absorpt_coefficient_mu    1.547

# Sheldrick geometric approximatio 0.93 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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    'USER DEFINED STRUCTURE SOLUTION'
_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      123
_diffrn_reflns_number            15233
_reflns_number_total             4353
_diffrn_reflns_av_R_equivalents  0.072
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4353 
# Theoretical number of reflections is about 9275 


_diffrn_reflns_theta_min         1.811
_diffrn_reflns_theta_max         25.864
_diffrn_measured_fraction_theta_max 0.938

_diffrn_reflns_theta_full        25.088
_diffrn_measured_fraction_theta_full 0.950


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   2.03
_oxford_diffrn_Wilson_scale      229.13

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

_refine_diff_density_min         -4.75
_refine_diff_density_max         4.08


# 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>-10.0\s(I)
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     14
_refine_ls_number_parameters     263
_oxford_refine_ls_R_factor_ref   0.1608
_refine_ls_wR_factor_ref         0.4127
_refine_ls_goodness_of_fit_ref   1.5578
_refine_ls_shift/su_max          0.0051076
_refine_ls_shift/su_mean         0.0000928


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4333
_refine_ls_R_factor_all          0.1608
_refine_ls_wR_factor_all         0.4127

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2731
_refine_ls_R_factor_gt           0.1186
_refine_ls_wR_factor_gt          0.3897

# 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.20P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.6010(12) -0.0789(5) 0.4544(14) 0.0544 1.0000 Uani . . . . . .
C2 C 0.6666(10) -0.0233(4) 0.4948(11) 0.0364 1.0000 Uani . . . . . .
C3 C 0.7114(11) -0.0141(5) 0.6192(12) 0.0448 1.0000 Uani . . . . . .
C4 C 0.7766(10) 0.0364(4) 0.6567(11) 0.0374 1.0000 Uani . . . . . .
C5 C 0.7996(10) 0.0817(4) 0.5689(10) 0.0324 1.0000 Uani . . . . . .
C6 C 0.7560(10) 0.0753(4) 0.4461(10) 0.0352 1.0000 Uani . . . . . .
C7 C 0.6909(11) 0.0237(5) 0.4082(11) 0.0407 1.0000 Uani . . . . . .
C8 C 0.8747(10) 0.1354(4) 0.6134(9) 0.0302 1.0000 Uani . . . . . .
O9 O 0.8921(8) 0.1459(3) 0.7269(7) 0.0426 1.0000 Uani . . . . . .
C10 C 0.9364(9) 0.1750(4) 0.5118(9) 0.0295 1.0000 Uani . . . . . .
C11 C 1.0614(10) 0.1447(5) 0.4606(11) 0.0417 1.0000 Uani . . . . . .
N12 N 0.9721(8) 0.2327(3) 0.5731(8) 0.0305 1.0000 Uani . . . . . .
C13 C 0.9961(11) 0.2812(4) 0.4800(10) 0.0394 1.0000 Uani . . . . . .
C14 C 0.0304(10) 0.5574(4) 0.3301(11) 0.0410 1.0000 Uani . . . . . .
C15 C 0.1290(10) 0.5124(4) 0.3826(10) 0.0365 1.0000 Uani . . . . . .
C16 C 0.2218(11) 0.5293(5) 0.4756(12) 0.0480 1.0000 Uani . . . . . .
C17 C 0.3105(12) 0.4880(4) 0.5213(11) 0.0427 1.0000 Uani . . . . . .
C18 C 0.3111(9) 0.4292(4) 0.4766(9) 0.0322 1.0000 Uani . . . . . .
C19 C 0.2204(9) 0.4137(4) 0.3816(10) 0.0337 1.0000 Uani . . . . . .
C20 C 0.1297(11) 0.4546(5) 0.3372(10) 0.0391 1.0000 Uani . . . . . .
C21 C 0.4042(10) 0.3868(5) 0.5388(10) 0.0357 1.0000 Uani . . . . . .
O22 O 0.4537(8) 0.3959(4) 0.6427(8) 0.0594 1.0000 Uani . . . . . .
C23 C 0.4412(9) 0.3310(4) 0.4630(10) 0.0334 1.0000 Uani . . . . . .
C24 C 0.5498(11) 0.3466(5) 0.3674(10) 0.0393 1.0000 Uani . . . . . .
N25 N 0.4861(9) 0.2862(3) 0.5554(8) 0.0337 1.0000 Uani . . . . . .
C26 C 0.5191(11) 0.2275(4) 0.4980(11) 0.0418 1.0000 Uani . . . . . .
Cl20 Cl 0.24966(7) 0.25361(7) 0.22233(7) 0.0457 0.594(13) Uani . U P . . .
Br21 Br 0.24838(7) 0.25351(7) 0.22060(7) 0.0340 0.406(13) Uani . U P . . .
Cl10 Cl 0.74132(7) 0.29786(7) 0.71389(7) 0.0363 0.599(13) Uani . U P . . .
Br11 Br 0.74423(7) 0.29989(7) 0.71607(7) 0.0348 0.401(13) Uani . U P . . .
H13 H 0.5219 -0.0696 0.4109 0.0643 1.0000 Uiso R . . . . .
H11 H 0.6559 -0.1031 0.4000 0.0636 1.0000 Uiso R . . . . .
H12 H 0.5820 -0.1002 0.5305 0.0647 1.0000 Uiso R . . . . .
H31 H 0.6911 -0.0425 0.6821 0.0399 1.0000 Uiso R . . . . .
H41 H 0.7979 0.0431 0.7435 0.0349 1.0000 Uiso R . . . . .
H61 H 0.7749 0.1053 0.3826 0.0346 1.0000 Uiso R . . . . .
H71 H 0.6642 0.0156 0.3218 0.0379 1.0000 Uiso R . . . . .
H101 H 0.8759 0.1812 0.4407 0.0273 1.0000 Uiso R . . . . .
H113 H 1.1010 0.1669 0.3917 0.0496 1.0000 Uiso R . . . . .
H111 H 1.1227 0.1427 0.5284 0.0502 1.0000 Uiso R . . . . .
H112 H 1.0420 0.1045 0.4346 0.0496 1.0000 Uiso R . . . . .
H131 H 1.0134 0.3186 0.5224 0.0473 1.0000 Uiso R . . . . .
H133 H 1.0689 0.2710 0.4264 0.0476 1.0000 Uiso R . . . . .
H132 H 0.9193 0.2840 0.4299 0.0483 1.0000 Uiso R . . . . .
H142 H -0.0075 0.5431 0.2517 0.0479 1.0000 Uiso R . . . . .
H141 H 0.0694 0.5965 0.3157 0.0483 1.0000 Uiso R . . . . .
H143 H -0.0387 0.5609 0.3909 0.0479 1.0000 Uiso R . . . . .
H161 H 0.2240 0.5706 0.5029 0.0377 1.0000 Uiso R . . . . .
H171 H 0.3740 0.5005 0.5807 0.0371 1.0000 Uiso R . . . . .
H191 H 0.2191 0.3730 0.3532 0.0316 1.0000 Uiso R . . . . .
H201 H 0.0640 0.4419 0.2786 0.0335 1.0000 Uiso R . . . . .
H231 H 0.3648 0.3149 0.4202 0.0304 1.0000 Uiso R . . . . .
H242 H 0.5682 0.3119 0.3170 0.0524 1.0000 Uiso R . . . . .
H241 H 0.6289 0.3590 0.4104 0.0536 1.0000 Uiso R . . . . .
H243 H 0.5182 0.3786 0.3142 0.0531 1.0000 Uiso R . . . . .
H262 H 0.5394 0.1992 0.5649 0.0526 1.0000 Uiso R . . . . .
H263 H 0.5948 0.2322 0.4447 0.0524 1.0000 Uiso R . . . . .
H261 H 0.4441 0.2136 0.4477 0.0531 1.0000 Uiso R . . . . .
H122 H 0.9066 0.2445 0.6228 0.0332 1.0000 Uiso R . . . . .
H252 H 0.4201 0.2789 0.6104 0.0391 1.0000 Uiso R . . . . .
H121 H 1.0443 0.2286 0.6209 0.0342 1.0000 Uiso R . . . . .
H251 H 0.5537 0.3010 0.5997 0.0385 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.048(7) 0.040(7) 0.075(10) -0.017(6) 0.005(7) -0.007(5)
C2 0.023(5) 0.043(6) 0.042(7) -0.001(5) 0.004(5) -0.002(4)
C3 0.051(7) 0.032(6) 0.052(8) 0.006(5) 0.002(6) 0.000(5)
C4 0.037(6) 0.037(6) 0.038(6) 0.007(5) 0.000(5) -0.006(5)
C5 0.029(5) 0.034(6) 0.034(6) 0.006(5) 0.006(5) 0.004(4)
C6 0.038(6) 0.036(6) 0.032(6) 0.005(5) 0.013(5) -0.003(4)
C7 0.041(6) 0.050(7) 0.031(6) -0.015(5) 0.000(5) -0.008(5)
C8 0.036(6) 0.030(5) 0.025(6) 0.007(4) 0.007(5) 0.007(4)
O9 0.065(5) 0.041(4) 0.022(4) 0.004(3) 0.007(4) -0.005(4)
C10 0.026(5) 0.040(6) 0.023(5) -0.008(4) 0.007(4) -0.004(4)
C11 0.033(6) 0.049(7) 0.043(7) -0.016(5) 0.006(5) -0.006(5)
N12 0.024(4) 0.040(5) 0.027(5) -0.002(4) 0.006(4) -0.001(3)
C13 0.045(6) 0.034(6) 0.039(7) 0.003(5) 0.016(6) 0.003(5)
C14 0.046(7) 0.040(6) 0.037(7) 0.004(5) 0.006(6) 0.004(5)
C15 0.029(6) 0.039(6) 0.041(7) 0.010(5) 0.005(5) -0.001(4)
C16 0.041(7) 0.035(6) 0.068(9) -0.010(6) 0.013(7) -0.011(5)
C17 0.048(7) 0.034(6) 0.046(7) -0.004(5) 0.001(6) -0.008(5)
C18 0.030(5) 0.039(6) 0.028(6) -0.003(5) 0.007(5) 0.002(4)
C19 0.030(5) 0.034(5) 0.037(6) -0.002(5) 0.007(5) -0.005(4)
C20 0.047(7) 0.041(6) 0.030(6) -0.006(5) -0.001(5) -0.009(5)
C21 0.034(6) 0.041(6) 0.032(6) -0.007(5) -0.002(5) -0.001(4)
O22 0.063(6) 0.069(6) 0.045(5) -0.024(4) -0.019(5) 0.015(4)
C23 0.025(5) 0.034(5) 0.041(6) -0.006(5) -0.001(5) 0.003(4)
C24 0.048(6) 0.037(6) 0.033(6) 0.002(5) 0.010(5) 0.005(5)
N25 0.033(5) 0.038(5) 0.030(5) 0.000(4) 0.005(4) 0.000(4)
C26 0.048(7) 0.031(6) 0.047(7) -0.003(5) 0.000(6) 0.002(5)
Cl20 0.036(6) 0.065(6) 0.036(6) -0.013(6) 0.010(6) -0.006(6)
Br21 0.014(3) 0.064(4) 0.024(3) -0.003(3) -0.005(3) 0.005(3)
Cl10 0.041(5) 0.015(3) 0.054(6) 0.000(3) 0.022(4) 0.003(3)
Br11 0.014(2) 0.078(4) 0.013(2) -0.013(2) -0.011(2) -0.002(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.0942(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
C1 . C2 . 1.478(14) yes
C1 . H13 . 0.945 no
C1 . H11 . 0.967 no
C1 . H12 . 0.952 no
C2 . C3 . 1.395(16) yes
C2 . C7 . 1.417(15) yes
C3 . C4 . 1.370(14) yes
C3 . H31 . 0.942 no
C4 . C5 . 1.394(14) yes
C4 . H41 . 0.947 no
C5 . C6 . 1.368(14) yes
C5 . C8 . 1.500(14) yes
C6 . C7 . 1.392(14) yes
C6 . H61 . 0.969 no
C7 . H71 . 0.962 no
C8 . O9 . 1.227(12) yes
C8 . C10 . 1.527(13) yes
C10 . C11 . 1.538(13) yes
C10 . N12 . 1.493(12) yes
C10 . H101 . 0.973 no
C11 . H113 . 0.967 no
C11 . H111 . 0.944 no
C11 . H112 . 0.965 no
N12 . C13 . 1.484(12) yes
N12 . H122 . 0.888 no
N12 . H121 . 0.889 no
C13 . H131 . 0.969 no
C13 . H133 . 0.959 no
C13 . H132 . 0.939 no
C14 . C15 . 1.524(14) yes
C14 . H142 . 0.961 no
C14 . H141 . 0.977 no
C14 . H143 . 0.954 no
C15 . C16 . 1.403(16) yes
C15 . C20 . 1.385(14) yes
C16 . C17 . 1.376(16) yes
C16 . H161 . 0.972 no
C17 . C18 . 1.404(13) yes
C17 . H171 . 0.937 no
C18 . C19 . 1.396(15) yes
C18 . C21 . 1.489(14) yes
C19 . C20 . 1.379(14) yes
C19 . H191 . 0.963 no
C20 . H201 . 0.948 no
C21 . O22 . 1.215(13) yes
C21 . C23 . 1.534(14) yes
C23 . C24 . 1.535(13) yes
C23 . N25 . 1.469(13) yes
C23 . H231 . 0.965 no
C24 . H242 . 0.962 no
C24 . H241 . 0.959 no
C24 . H243 . 0.966 no
N25 . C26 . 1.491(12) yes
N25 . H252 . 0.902 no
N25 . H251 . 0.891 no
C26 . H262 . 0.969 no
C26 . H263 . 0.959 no
C26 . H261 . 0.975 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
C2 . C1 . H13 . 109.3 no
C2 . C1 . H11 . 112.6 no
H13 . C1 . H11 . 109.3 no
C2 . C1 . H12 . 106.1 no
H13 . C1 . H12 . 110.0 no
H11 . C1 . H12 . 109.5 no
C1 . C2 . C3 . 122.6(10) yes
C1 . C2 . C7 . 121.8(11) yes
C3 . C2 . C7 . 115.6(10) yes
C2 . C3 . C4 . 123.1(10) yes
C2 . C3 . H31 . 118.9 no
C4 . C3 . H31 . 117.9 no
C3 . C4 . C5 . 119.8(11) yes
C3 . C4 . H41 . 121.0 no
C5 . C4 . H41 . 118.8 no
C4 . C5 . C6 . 119.5(10) yes
C4 . C5 . C8 . 118.0(10) yes
C6 . C5 . C8 . 122.5(9) yes
C5 . C6 . C7 . 120.4(10) yes
C5 . C6 . H61 . 120.8 no
C7 . C6 . H61 . 118.7 no
C2 . C7 . C6 . 121.5(10) yes
C2 . C7 . H71 . 114.5 no
C6 . C7 . H71 . 123.9 no
C5 . C8 . O9 . 121.9(8) yes
C5 . C8 . C10 . 117.5(8) yes
O9 . C8 . C10 . 120.5(9) yes
C8 . C10 . C11 . 109.2(8) yes
C8 . C10 . N12 . 107.8(7) yes
C11 . C10 . N12 . 109.7(8) yes
C8 . C10 . H101 . 111.1 no
C11 . C10 . H101 . 108.2 no
N12 . C10 . H101 . 110.8 no
C10 . C11 . H113 . 112.4 no
C10 . C11 . H111 . 107.3 no
H113 . C11 . H111 . 108.2 no
C10 . C11 . H112 . 110.3 no
H113 . C11 . H112 . 110.9 no
H111 . C11 . H112 . 107.5 no
C10 . N12 . C13 . 113.3(8) yes
C10 . N12 . H122 . 109.4 no
C13 . N12 . H122 . 107.1 no
C10 . N12 . H121 . 110.5 no
C13 . N12 . H121 . 108.0 no
H122 . N12 . H121 . 108.3 no
N12 . C13 . H131 . 111.5 no
N12 . C13 . H133 . 110.0 no
H131 . C13 . H133 . 109.8 no
N12 . C13 . H132 . 106.3 no
H131 . C13 . H132 . 110.2 no
H133 . C13 . H132 . 109.0 no
C15 . C14 . H142 . 110.2 no
C15 . C14 . H141 . 112.9 no
H142 . C14 . H141 . 109.2 no
C15 . C14 . H143 . 107.2 no
H142 . C14 . H143 . 108.0 no
H141 . C14 . H143 . 109.2 no
C14 . C15 . C16 . 120.5(10) yes
C14 . C15 . C20 . 120.2(11) yes
C16 . C15 . C20 . 119.3(10) yes
C15 . C16 . C17 . 119.6(10) yes
C15 . C16 . H161 . 118.5 no
C17 . C16 . H161 . 121.8 no
C16 . C17 . C18 . 121.5(12) yes
C16 . C17 . H171 . 118.4 no
C18 . C17 . H171 . 120.0 no
C17 . C18 . C19 . 118.0(10) yes
C17 . C18 . C21 . 117.4(10) yes
C19 . C18 . C21 . 124.5(9) yes
C18 . C19 . C20 . 120.7(9) yes
C18 . C19 . H191 . 117.7 no
C20 . C19 . H191 . 121.4 no
C15 . C20 . C19 . 120.9(10) yes
C15 . C20 . H201 . 120.0 no
C19 . C20 . H201 . 119.0 no
C18 . C21 . O22 . 122.9(9) yes
C18 . C21 . C23 . 116.9(9) yes
O22 . C21 . C23 . 120.1(10) yes
C21 . C23 . C24 . 109.4(8) yes
C21 . C23 . N25 . 107.2(9) yes
C24 . C23 . N25 . 111.6(8) yes
C21 . C23 . H231 . 110.5 no
C24 . C23 . H231 . 111.0 no
N25 . C23 . H231 . 107.1 no
C23 . C24 . H242 . 108.5 no
C23 . C24 . H241 . 111.1 no
H242 . C24 . H241 . 109.4 no
C23 . C24 . H243 . 108.2 no
H242 . C24 . H243 . 110.6 no
H241 . C24 . H243 . 109.2 no
C23 . N25 . C26 . 114.2(9) yes
C23 . N25 . H252 . 108.7 no
C26 . N25 . H252 . 105.5 no
C23 . N25 . H251 . 108.8 no
C26 . N25 . H251 . 111.7 no
H252 . N25 . H251 . 107.8 no
N25 . C26 . H262 . 109.6 no
N25 . C26 . H263 . 108.7 no
H262 . C26 . H263 . 109.2 no
N25 . C26 . H261 . 109.0 no
H262 . C26 . H261 . 110.1 no
H263 . C26 . H261 . 110.1 no


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 24/01/14 at 15:51:58
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
EQUIV CL(10, X'S) BR(11, X'S) 
EQUIV CL(20, X'S) BR(21, X'S) 
EQUIV CL(10, OCC) BR(11, OCC) 
WEIGHT -1 BR(11, OCC) 
EQUIV CL(20, OCC) BR(21, OCC) 
WEIGHT -1 BR(21, OCC) 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE N   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 263,X'S) H   ( 261,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 24/01/14 at 15:51:58
#
#LIST     16                                                                    
VIBRATION 0.0, 0.020000 = CL(20) TO BR(21) 
U(IJ)'S  0.0, 0.010000 = CL(20) TO BR(21) 
VIBRATION 0.0, 0.020000 = CL(10) TO BR(11) 
U(IJ)'S  0.0, 0.010000 = CL(10) TO BR(11) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 983752'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1c_7030
_oxford_structure_analysis_title '7030 in P2(1)/c'
_chemical_name_systematic        
"70:30 (+-)-4'-methylmethcathinone hydrochloride hydrobromide salt solution"
_chemical_melting_point          '507 K'

#looking for refcif 


# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 

_cell_length_a                   10.1012(5)
_cell_length_b                   22.5506(12)
_cell_length_c                   10.4737(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.441(3)
_cell_angle_gamma                90
_cell_volume                     2385.7(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C9 H14 Br1 Cl1 N1 O1 
# Dc =      1.49 Fooo =    955.57 Mu =     36.36 M =    535.15
# Found Formula = C11 H16 Br0.30 Cl0.70 N1 O1 
# Dc =      1.26 FOOO =    955.57 Mu =     12.36 M =    454.31

_chemical_formula_sum            'C11 H16 Br0.30 Cl0.70 N1 O1'
_chemical_formula_moiety         'C11 H16 Br0.30 Cl0.70 N1 O1'
_chemical_compound_source        ?
_chemical_formula_weight         227.16


_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.110
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.900

_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             955.566
_exptl_absorpt_coefficient_mu    1.236

# Sheldrick geometric approximatio 0.69 0.87 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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    'USER DEFINED STRUCTURE SOLUTION'
_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      123
_diffrn_reflns_number            30693
_reflns_number_total             4888
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4888 
# Theoretical number of reflections is about 9792 


_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_max         26.405
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        26.405
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.13
_oxford_diffrn_Wilson_scale      100.45

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

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.30


# 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>-10.0\s(I)
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     0
_refine_ls_number_parameters     263
_oxford_refine_ls_R_factor_ref   0.0374
_refine_ls_wR_factor_ref         0.0753
_refine_ls_goodness_of_fit_ref   1.0369
_refine_ls_shift/su_max          0.0003601
_refine_ls_shift/su_mean         0.0000463


# The values computed from all data 
_oxford_reflns_number_all        4871
_refine_ls_R_factor_all          0.0374
_refine_ls_wR_factor_all         0.0753

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4403
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_gt          0.0698

# 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    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 2.26P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C1 C 0.6006(2) -0.07742(10) 0.4491(2) 0.0428 1.0000 Uani . . . . . .
C2 C 0.66923(19) -0.02121(9) 0.4909(2) 0.0327 1.0000 Uani . . . . . .
C3 C 0.7149(2) -0.01480(9) 0.6157(2) 0.0360 1.0000 Uani . . . . . .
C4 C 0.7798(2) 0.03637(9) 0.65397(19) 0.0331 1.0000 Uani . . . . . .
C5 C 0.80201(18) 0.08225(8) 0.56754(17) 0.0258 1.0000 Uani . . . . . .
C6 C 0.75451(18) 0.07633(9) 0.44269(18) 0.0288 1.0000 Uani . . . . . .
C7 C 0.68805(19) 0.02515(9) 0.40584(19) 0.0324 1.0000 Uani . . . . . .
C8 C 0.87677(18) 0.13527(8) 0.61257(17) 0.0251 1.0000 Uani . . . . . .
O9 O 0.89562(15) 0.14532(6) 0.72540(12) 0.0368 1.0000 Uani . . . . . .
C10 C 0.93836(17) 0.17556(8) 0.51270(17) 0.0239 1.0000 Uani . . . . . .
C11 C 1.0617(2) 0.14654(9) 0.4585(2) 0.0363 1.0000 Uani . . . . . .
N12 N 0.97325(15) 0.23322(6) 0.57411(14) 0.0239 1.0000 Uani . . . . . .
C13 C 0.9973(2) 0.28170(9) 0.48130(19) 0.0329 1.0000 Uani . . . . . .
C14 C 0.0345(2) 0.55731(9) 0.3337(2) 0.0359 1.0000 Uani . . . . . .
C15 C 0.13194(19) 0.51253(8) 0.38420(18) 0.0285 1.0000 Uani . . . . . .
C16 C 0.2227(2) 0.52782(9) 0.4788(2) 0.0359 1.0000 Uani . . . . . .
C17 C 0.3113(2) 0.48707(9) 0.5279(2) 0.0352 1.0000 Uani . . . . . .
C18 C 0.31189(18) 0.42862(8) 0.48190(18) 0.0281 1.0000 Uani . . . . . .
C19 C 0.22323(19) 0.41314(8) 0.38557(18) 0.0284 1.0000 Uani . . . . . .
C20 C 0.1343(2) 0.45473(9) 0.33828(18) 0.0309 1.0000 Uani . . . . . .
C21 C 0.4038(2) 0.38528(9) 0.54285(19) 0.0326 1.0000 Uani . . . . . .
O22 O 0.45141(17) 0.39336(7) 0.64790(15) 0.0517 1.0000 Uani . . . . . .
C23 C 0.44196(18) 0.33005(8) 0.46716(18) 0.0275 1.0000 Uani . . . . . .
C24 C 0.5513(2) 0.34545(9) 0.3734(2) 0.0373 1.0000 Uani . . . . . .
N25 N 0.48624(16) 0.28415(7) 0.55952(15) 0.0282 1.0000 Uani . . . . . .
C26 C 0.5199(2) 0.22625(9) 0.5001(2) 0.0339 1.0000 Uani . . . . . .
H13 H 0.5264 -0.0665 0.3961 0.0662 1.0000 Uiso R . . . . .
H11 H 0.6601 -0.1013 0.4018 0.0652 1.0000 Uiso R . . . . .
H12 H 0.5686 -0.1000 0.5196 0.0663 1.0000 Uiso R . . . . .
H31 H 0.7070 -0.0472 0.6705 0.0453 1.0000 Uiso R . . . . .
H41 H 0.8191 0.0362 0.7386 0.0399 1.0000 Uiso R . . . . .
H61 H 0.7603 0.1095 0.3890 0.0332 1.0000 Uiso R . . . . .
H71 H 0.6455 0.0260 0.3239 0.0369 1.0000 Uiso R . . . . .
H101 H 0.8715 0.1860 0.4476 0.0275 1.0000 Uiso R . . . . .
H113 H 1.0938 0.1725 0.3942 0.0505 1.0000 Uiso R . . . . .
H111 H 1.1315 0.1410 0.5236 0.0509 1.0000 Uiso R . . . . .
H112 H 1.0388 0.1097 0.4228 0.0510 1.0000 Uiso R . . . . .
H131 H 1.0207 0.3149 0.5352 0.0444 1.0000 Uiso R . . . . .
H133 H 1.0714 0.2731 0.4267 0.0445 1.0000 Uiso R . . . . .
H132 H 0.9186 0.2891 0.4293 0.0451 1.0000 Uiso R . . . . .
H142 H -0.0064 0.5447 0.2524 0.0607 1.0000 Uiso R . . . . .
H141 H 0.0866 0.5923 0.3215 0.0600 1.0000 Uiso R . . . . .
H143 H -0.0344 0.5664 0.3942 0.0595 1.0000 Uiso R . . . . .
H161 H 0.2210 0.5653 0.5169 0.0453 1.0000 Uiso R . . . . .
H171 H 0.3656 0.4949 0.6032 0.0446 1.0000 Uiso R . . . . .
H191 H 0.2244 0.3757 0.3469 0.0340 1.0000 Uiso R . . . . .
H201 H 0.0784 0.4458 0.2670 0.0352 1.0000 Uiso R . . . . .
H231 H 0.3680 0.3163 0.4167 0.0303 1.0000 Uiso R . . . . .
H242 H 0.5716 0.3137 0.3153 0.0558 1.0000 Uiso R . . . . .
H241 H 0.6294 0.3535 0.4272 0.0550 1.0000 Uiso R . . . . .
H243 H 0.5245 0.3794 0.3253 0.0559 1.0000 Uiso R . . . . .
H262 H 0.5411 0.1968 0.5659 0.0457 1.0000 Uiso R . . . . .
H263 H 0.5974 0.2313 0.4478 0.0462 1.0000 Uiso R . . . . .
H261 H 0.4440 0.2147 0.4461 0.0465 1.0000 Uiso R . . . . .
H121 H 1.0483 0.2265 0.6255 0.0346 1.0000 Uiso R . . . . .
H122 H 0.9066 0.2446 0.6306 0.0353 1.0000 Uiso R . . . . .
H252 H 0.4185 0.2757 0.6158 0.0366 1.0000 Uiso R . . . . .
H251 H 0.5605 0.2953 0.6064 0.0366 1.0000 Uiso R . . . . .
Cl20 Cl 0.248128(16) 0.255222(16) 0.222379(16) 0.0477 0.698(3) Uani . . P . . .
Br21 Br 0.247018(16) 0.256521(16) 0.223415(16) 0.0199 0.302(3) Uani . . P . . .
Cl10 Cl 0.746842(12) 0.295490(12) 0.721378(12) 0.0469 0.697(3) Uani . . P . . .
Br11 Br 0.746247(12) 0.295889(12) 0.720457(12) 0.0146 0.303(3) Uani . . P . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0371(12) 0.0321(12) 0.0592(15) -0.0110(10) 0.0054(10) -0.0054(9)
C2 0.0262(9) 0.0283(10) 0.0437(12) -0.0087(9) 0.0060(9) -0.0009(8)
C3 0.0387(11) 0.0261(10) 0.0433(12) 0.0058(9) 0.0008(9) -0.0020(9)
C4 0.0378(11) 0.0311(11) 0.0303(10) 0.0042(8) -0.0031(8) -0.0016(9)
C5 0.0270(9) 0.0243(9) 0.0262(9) -0.0006(7) 0.0018(7) 0.0006(7)
C6 0.0302(10) 0.0309(10) 0.0254(9) -0.0020(8) 0.0051(8) -0.0033(8)
C7 0.0301(10) 0.0381(11) 0.0289(10) -0.0067(8) 0.0046(8) -0.0049(8)
C8 0.0280(9) 0.0250(9) 0.0222(9) -0.0004(7) -0.0005(7) 0.0038(7)
O9 0.0583(10) 0.0300(8) 0.0220(7) 0.0013(6) -0.0034(6) -0.0073(7)
C10 0.0251(9) 0.0258(10) 0.0209(9) -0.0028(7) -0.0018(7) -0.0009(7)
C11 0.0324(11) 0.0355(12) 0.0412(12) -0.0113(9) 0.0071(9) -0.0008(9)
N12 0.0264(8) 0.0247(8) 0.0207(7) -0.0006(6) 0.0017(6) -0.0006(6)
C13 0.0420(11) 0.0276(10) 0.0291(10) 0.0043(8) 0.0064(9) -0.0012(9)
C14 0.0410(12) 0.0294(11) 0.0373(11) 0.0047(9) 0.0057(9) 0.0012(9)
C15 0.0303(10) 0.0271(10) 0.0281(10) 0.0033(8) 0.0089(8) -0.0015(8)
C16 0.0379(11) 0.0241(10) 0.0457(12) -0.0078(9) 0.0039(9) -0.0027(8)
C17 0.0344(11) 0.0322(11) 0.0390(11) -0.0116(9) -0.0024(9) -0.0012(9)
C18 0.0272(9) 0.0274(10) 0.0297(10) -0.0051(8) 0.0043(8) 0.0003(8)
C19 0.0336(10) 0.0223(9) 0.0295(10) -0.0041(7) 0.0051(8) -0.0016(8)
C20 0.0338(10) 0.0308(10) 0.0280(10) -0.0011(8) -0.0002(8) -0.0018(8)
C21 0.0324(10) 0.0333(11) 0.0322(11) -0.0078(8) -0.0008(8) 0.0007(8)
O22 0.0634(11) 0.0500(10) 0.0415(9) -0.0211(8) -0.0200(8) 0.0199(8)
C23 0.0282(9) 0.0266(10) 0.0278(10) -0.0036(8) -0.0030(8) 0.0008(8)
C24 0.0442(12) 0.0320(11) 0.0359(11) -0.0001(9) 0.0076(9) 0.0013(9)
N25 0.0280(8) 0.0308(9) 0.0257(8) -0.0041(7) 0.0002(6) 0.0006(7)
C26 0.0419(12) 0.0266(10) 0.0333(10) -0.0020(8) 0.0009(9) 0.0046(9)
Cl20 0.030(3) 0.073(3) 0.040(2) -0.0083(18) 0.0002(17) 0.0029(18)
Br21 0.0139(15) 0.0345(13) 0.0114(12) -0.0056(10) 0.0006(10) 0.0018(10)
Cl10 0.033(3) 0.060(3) 0.048(2) -0.0074(16) -0.0007(15) 0.0018(18)
Br11 0.0120(14) 0.0244(12) 0.0074(9) -0.0061(8) -0.0003(8) 0.0006(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.09924(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
C1 . C2 . 1.508(3) yes
C1 . H13 . 0.961 no
C1 . H11 . 0.949 no
C1 . H12 . 0.956 no
C2 . C3 . 1.390(3) yes
C2 . C7 . 1.388(3) yes
C3 . C4 . 1.385(3) yes
C3 . H31 . 0.934 no
C4 . C5 . 1.394(3) yes
C4 . H41 . 0.969 no
C5 . C6 . 1.396(3) yes
C5 . C8 . 1.489(3) yes
C6 . C7 . 1.388(3) yes
C6 . H61 . 0.939 no
C7 . H71 . 0.957 no
C8 . O9 . 1.217(2) yes
C8 . C10 . 1.522(2) yes
C10 . C11 . 1.521(3) yes
C10 . N12 . 1.492(2) yes
C10 . H101 . 0.985 no
C11 . H113 . 0.951 no
C11 . H111 . 0.985 no
C11 . H112 . 0.940 no
N12 . C13 . 1.484(2) yes
N12 . H121 . 0.939 no
N12 . H122 . 0.936 no
C13 . H131 . 0.966 no
C13 . H133 . 0.965 no
C13 . H132 . 0.974 no
C14 . C15 . 1.503(3) yes
C14 . H142 . 0.986 no
C14 . H141 . 0.959 no
C14 . H143 . 0.966 no
C15 . C16 . 1.388(3) yes
C15 . C20 . 1.390(3) yes
C16 . C17 . 1.379(3) yes
C16 . H161 . 0.934 no
C17 . C18 . 1.404(3) yes
C17 . H171 . 0.974 no
C18 . C19 . 1.388(3) yes
C18 . C21 . 1.488(3) yes
C19 . C20 . 1.387(3) yes
C19 . H191 . 0.937 no
C20 . H201 . 0.954 no
C21 . O22 . 1.211(2) yes
C21 . C23 . 1.528(3) yes
C23 . C24 . 1.524(3) yes
C23 . N25 . 1.483(2) yes
C23 . H231 . 0.963 no
C24 . H242 . 0.962 no
C24 . H241 . 0.983 no
C24 . H243 . 0.955 no
N25 . C26 . 1.487(2) yes
N25 . H252 . 0.926 no
N25 . H251 . 0.928 no
C26 . H262 . 0.979 no
C26 . H263 . 0.965 no
C26 . H261 . 0.985 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
C2 . C1 . H13 . 107.9 no
C2 . C1 . H11 . 109.6 no
H13 . C1 . H11 . 109.7 no
C2 . C1 . H12 . 112.5 no
H13 . C1 . H12 . 108.4 no
H11 . C1 . H12 . 108.7 no
C1 . C2 . C3 . 120.6(2) yes
C1 . C2 . C7 . 120.76(19) yes
C3 . C2 . C7 . 118.63(18) yes
C2 . C3 . C4 . 120.79(19) yes
C2 . C3 . H31 . 117.8 no
C4 . C3 . H31 . 121.2 no
C3 . C4 . C5 . 120.57(19) yes
C3 . C4 . H41 . 116.9 no
C5 . C4 . H41 . 122.0 no
C4 . C5 . C6 . 118.78(17) yes
C4 . C5 . C8 . 118.31(17) yes
C6 . C5 . C8 . 122.91(17) yes
C5 . C6 . C7 . 120.12(18) yes
C5 . C6 . H61 . 117.6 no
C7 . C6 . H61 . 121.9 no
C6 . C7 . C2 . 121.06(19) yes
C6 . C7 . H71 . 116.4 no
C2 . C7 . H71 . 121.9 no
C5 . C8 . O9 . 122.16(17) yes
C5 . C8 . C10 . 118.07(15) yes
O9 . C8 . C10 . 119.64(16) yes
C8 . C10 . C11 . 109.88(16) yes
C8 . C10 . N12 . 108.69(14) yes
C11 . C10 . N12 . 110.15(15) yes
C8 . C10 . H101 . 109.7 no
C11 . C10 . H101 . 113.8 no
N12 . C10 . H101 . 104.4 no
C10 . C11 . H113 . 106.6 no
C10 . C11 . H111 . 112.3 no
H113 . C11 . H111 . 108.7 no
C10 . C11 . H112 . 109.2 no
H113 . C11 . H112 . 110.2 no
H111 . C11 . H112 . 109.7 no
C10 . N12 . C13 . 113.52(14) yes
C10 . N12 . H121 . 107.0 no
C13 . N12 . H121 . 111.1 no
C10 . N12 . H122 . 110.1 no
C13 . N12 . H122 . 109.5 no
H121 . N12 . H122 . 105.3 no
N12 . C13 . H131 . 103.2 no
N12 . C13 . H133 . 111.8 no
H131 . C13 . H133 . 108.3 no
N12 . C13 . H132 . 110.8 no
H131 . C13 . H132 . 112.9 no
H133 . C13 . H132 . 109.7 no
C15 . C14 . H142 . 112.3 no
C15 . C14 . H141 . 104.0 no
H142 . C14 . H141 . 110.4 no
C15 . C14 . H143 . 112.6 no
H142 . C14 . H143 . 109.2 no
H141 . C14 . H143 . 108.2 no
C14 . C15 . C16 . 120.75(18) yes
C14 . C15 . C20 . 121.41(18) yes
C16 . C15 . C20 . 117.84(18) yes
C15 . C16 . C17 . 121.57(18) yes
C15 . C16 . H161 . 121.0 no
C17 . C16 . H161 . 117.2 no
C16 . C17 . C18 . 120.17(19) yes
C16 . C17 . H171 . 122.8 no
C18 . C17 . H171 . 116.4 no
C17 . C18 . C19 . 118.74(18) yes
C17 . C18 . C21 . 118.29(17) yes
C19 . C18 . C21 . 122.91(17) yes
C18 . C19 . C20 . 120.12(18) yes
C18 . C19 . H191 . 122.0 no
C20 . C19 . H191 . 117.7 no
C15 . C20 . C19 . 121.55(18) yes
C15 . C20 . H201 . 117.3 no
C19 . C20 . H201 . 120.9 no
C18 . C21 . O22 . 122.20(18) yes
C18 . C21 . C23 . 118.17(16) yes
O22 . C21 . C23 . 119.59(18) yes
C21 . C23 . C24 . 109.63(16) yes
C21 . C23 . N25 . 107.85(15) yes
C24 . C23 . N25 . 111.29(16) yes
C21 . C23 . H231 . 110.5 no
C24 . C23 . H231 . 106.4 no
N25 . C23 . H231 . 111.2 no
C23 . C24 . H242 . 113.4 no
C23 . C24 . H241 . 104.8 no
H242 . C24 . H241 . 109.0 no
C23 . C24 . H243 . 108.6 no
H242 . C24 . H243 . 108.9 no
H241 . C24 . H243 . 112.1 no
C23 . N25 . C26 . 114.12(15) yes
C23 . N25 . H252 . 109.8 no
C26 . N25 . H252 . 105.0 no
C23 . N25 . H251 . 113.2 no
C26 . N25 . H251 . 105.9 no
H252 . N25 . H251 . 108.5 no
N25 . C26 . H262 . 110.5 no
N25 . C26 . H263 . 108.9 no
H262 . C26 . H263 . 107.8 no
N25 . C26 . H261 . 107.0 no
H262 . C26 . H261 . 113.0 no
H263 . C26 . H261 . 109.6 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 21/01/14 at 17:51:46
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
EQUIV CL(10, X'S) BR(11, X'S) 
EQUIV CL(20, X'S) BR(21, X'S) 
EQUIV CL(10, OCC) BR(11, OCC) 
WEIGHT -1 BR(11, OCC) 
EQUIV CL(20, OCC) BR(21, OCC) 
WEIGHT -1 BR(21, OCC) 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE N   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 263,X'S) H   ( 261,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 21/01/14 at 17:51:46
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
#END
_database_code_depnum_ccdc_archive 'CCDC 983753'
