# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
#==============================================================================

############################################################# 
# ***oxford university chemical crystallography group*** 
# 
# this structure was solved by Russell W. Driver on 01/02/2014
# 
#############################################################

_audit_creation_date             2014-02-01
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 016RWD12
_chemical_name_systematic        .
_chemical_melting_point          'see SI'

_cell_length_a                   12.5878(2)
_cell_length_b                   9.3875(2)
_cell_length_c                   14.5609(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.3672(8)
_cell_angle_gamma                90
_cell_volume                     1702.32(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_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 = C18 H17 N2 O2 
# Dc =      1.14 Fooo =    728.00 Mu =      0.76 M =    293.35
# Found Formula = C18 H19 Cl1 N2 O3 
# Dc =      1.35 FOOO =    728.00 Mu =      2.43 M =    346.81

_chemical_formula_sum            'C18 H19 Cl1 N2 O3'
_chemical_formula_moiety         'C18 H19 Cl1 N2 O3'
_chemical_compound_source        syn
_chemical_formula_weight         346.81


_cell_measurement_reflns_used    7088
_cell_measurement_theta_min      1
_cell_measurement_theta_max      1
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.243

# Sheldrick geometric approximatio 0.91 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.91
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            29097
_reflns_number_total             3898
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections without Friedels Law is 12589 
# Number of reflections with Friedels Law is 3898 
# Theoretical number of reflections is about 3904 


_diffrn_reflns_theta_min         2.000
_diffrn_reflns_theta_max         27.483
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        27.483
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.22
_oxford_diffrn_Wilson_scale      1.67

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

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.34


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_number_parameters     217
_oxford_refine_ls_R_factor_ref   0.0572
_refine_ls_wR_factor_ref         0.1104
_refine_ls_goodness_of_fit_ref   0.9508
_refine_ls_shift/su_max          0.0003402
_refine_ls_shift/su_mean         0.0000371


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3888
_refine_ls_R_factor_all          0.0572
_refine_ls_wR_factor_all         0.1104

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3029
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_gt          0.0945

# 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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 47.6 77.7 46.4 18.9 3.99 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.15004(4) 0.14829(6) 0.68162(3) 0.0424 1.0000 Uani . . . . . .
C2 C 0.27377(13) 0.2080(2) 0.65720(11) 0.0301 1.0000 Uani . . . . . .
C3 C 0.28796(14) 0.3510(2) 0.63998(12) 0.0324 1.0000 Uani . . . . . .
C4 C 0.38762(14) 0.39788(18) 0.62218(11) 0.0288 1.0000 Uani . . . . . .
C5 C 0.47233(13) 0.30396(17) 0.62134(10) 0.0238 1.0000 Uani . . . . . .
C6 C 0.58186(12) 0.35721(16) 0.60594(10) 0.0218 1.0000 Uani . . . . . .
N7 N 0.62078(11) 0.27687(15) 0.53196(9) 0.0248 1.0000 Uani . . . . . .
C8 C 0.72433(13) 0.29786(16) 0.51568(11) 0.0231 1.0000 Uani . . . . . .
C9 C 0.80307(13) 0.35332(17) 0.58496(11) 0.0253 1.0000 Uani . . . . . .
C10 C 0.77592(13) 0.38630(17) 0.67666(11) 0.0253 1.0000 Uani . . . . . .
C11 C 0.66441(12) 0.34094(16) 0.69452(10) 0.0233 1.0000 Uani . . . . . .
C12 C 0.63270(14) 0.42965(17) 0.77366(11) 0.0270 1.0000 Uani . . . . . .
O13 O 0.58966(13) 0.54683(14) 0.75615(9) 0.0462 1.0000 Uani . . . . . .
N14 N 0.65224(11) 0.37883(14) 0.85997(9) 0.0253 1.0000 Uani . . . . . .
C15 C 0.62421(17) 0.4667(2) 0.93561(12) 0.0368 1.0000 Uani . . . . . .
C16 C 0.71511(18) 0.2526(2) 0.88827(13) 0.0392 1.0000 Uani . . . . . .
O17 O 0.83836(10) 0.44364(13) 0.73824(8) 0.0335 1.0000 Uani . . . . . .
C18 C 0.90902(14) 0.36904(19) 0.56725(13) 0.0326 1.0000 Uani . . . . . .
C19 C 0.93718(15) 0.3316(2) 0.48291(14) 0.0373 1.0000 Uani . . . . . .
C20 C 0.85846(15) 0.2777(2) 0.41371(13) 0.0341 1.0000 Uani . . . . . .
C21 C 0.75409(14) 0.26120(18) 0.42885(11) 0.0286 1.0000 Uani . . . . . .
C22 C 0.45569(14) 0.15986(19) 0.63783(13) 0.0333 1.0000 Uani . . . . . .
C23 C 0.35655(15) 0.1118(2) 0.65587(14) 0.0361 1.0000 Uani . . . . . .
H31 H 0.2310 0.4172 0.6416 0.0399 1.0000 Uiso R . . . . .
H41 H 0.3983 0.4953 0.6111 0.0351 1.0000 Uiso R . . . . .
H61 H 0.5773 0.4589 0.5887 0.0257 1.0000 Uiso R . . . . .
H111 H 0.6702 0.2405 0.7107 0.0278 1.0000 Uiso R . . . . .
H153 H 0.5894 0.4094 0.9775 0.0559 1.0000 Uiso R . . . . .
H151 H 0.6891 0.5038 0.9708 0.0569 1.0000 Uiso R . . . . .
H152 H 0.5803 0.5441 0.9134 0.0565 1.0000 Uiso R . . . . .
H161 H 0.6756 0.1835 0.9150 0.0608 1.0000 Uiso R . . . . .
H163 H 0.7755 0.2798 0.9366 0.0617 1.0000 Uiso R . . . . .
H162 H 0.7482 0.2111 0.8398 0.0593 1.0000 Uiso R . . . . .
H181 H 0.9619 0.4053 0.6143 0.0395 1.0000 Uiso R . . . . .
H191 H 1.0081 0.3406 0.4709 0.0442 1.0000 Uiso R . . . . .
H201 H 0.8769 0.2530 0.3556 0.0411 1.0000 Uiso R . . . . .
H211 H 0.7022 0.2267 0.3821 0.0347 1.0000 Uiso R . . . . .
H221 H 0.5128 0.0940 0.6364 0.0410 1.0000 Uiso R . . . . .
H231 H 0.3457 0.0155 0.6668 0.0431 1.0000 Uiso R . . . . .
H71 H 0.5756 0.2608 0.4836 0.0298 1.0000 Uiso R . . . . .
O1 O 0.01012(11) 0.72994(15) 0.14523(9) 0.0402 1.0000 Uani . . . . . .
H1 H 0.0484 0.6657 0.1724 0.0608 1.0000 Uiso R . . . . .
H2 H 0.0314 0.8015 0.1750 0.0602 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.6339(15)
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
Cl1 . C2 . 1.7399(18) yes
C2 . C3 . 1.382(3) yes
C2 . C23 . 1.381(3) yes
C3 . C4 . 1.389(2) yes
C3 . H31 . 0.952 no
C4 . C5 . 1.385(2) yes
C4 . H41 . 0.942 no
C5 . C6 . 1.514(2) yes
C5 . C22 . 1.395(2) yes
C6 . N7 . 1.4570(19) yes
C6 . C11 . 1.5416(19) yes
C6 . H61 . 0.986 no
N7 . C8 . 1.373(2) yes
N7 . H71 . 0.851 no
C8 . C9 . 1.407(2) yes
C8 . C21 . 1.413(2) yes
C9 . C10 . 1.459(2) yes
C9 . C18 . 1.403(2) yes
C10 . C11 . 1.525(2) yes
C10 . O17 . 1.2273(19) yes
C11 . C12 . 1.521(2) yes
C11 . H111 . 0.972 no
C12 . O13 . 1.236(2) yes
C12 . N14 . 1.333(2) yes
N14 . C15 . 1.460(2) yes
N14 . C16 . 1.451(2) yes
C15 . H153 . 0.965 no
C15 . H151 . 0.964 no
C15 . H152 . 0.941 no
C16 . H161 . 0.936 no
C16 . H163 . 0.992 no
C16 . H162 . 0.953 no
C18 . C19 . 1.373(3) yes
C18 . H181 . 0.946 no
C19 . C20 . 1.401(3) yes
C19 . H191 . 0.937 no
C20 . C21 . 1.372(2) yes
C20 . H201 . 0.938 no
C21 . H211 . 0.930 no
C22 . C23 . 1.388(3) yes
C22 . H221 . 0.951 no
C23 . H231 . 0.932 no
O1 . H1 . 0.835 no
O1 . H2 . 0.823 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
Cl1 . C2 . C3 . 119.55(14) yes
Cl1 . C2 . C23 . 119.47(15) yes
C3 . C2 . C23 . 120.98(16) yes
C2 . C3 . C4 . 119.07(16) yes
C2 . C3 . H31 . 120.8 no
C4 . C3 . H31 . 120.1 no
C3 . C4 . C5 . 121.15(16) yes
C3 . C4 . H41 . 119.7 no
C5 . C4 . H41 . 119.1 no
C4 . C5 . C6 . 120.67(14) yes
C4 . C5 . C22 . 118.73(16) yes
C6 . C5 . C22 . 120.57(15) yes
C5 . C6 . N7 . 110.49(12) yes
C5 . C6 . C11 . 111.16(12) yes
N7 . C6 . C11 . 108.00(12) yes
C5 . C6 . H61 . 109.7 no
N7 . C6 . H61 . 109.0 no
C11 . C6 . H61 . 108.5 no
C6 . N7 . C8 . 118.90(13) yes
C6 . N7 . H71 . 116.5 no
C8 . N7 . H71 . 114.8 no
N7 . C8 . C9 . 121.12(14) yes
N7 . C8 . C21 . 120.12(14) yes
C9 . C8 . C21 . 118.74(15) yes
C8 . C9 . C10 . 120.01(15) yes
C8 . C9 . C18 . 119.78(16) yes
C10 . C9 . C18 . 120.11(15) yes
C9 . C10 . C11 . 116.16(13) yes
C9 . C10 . O17 . 123.45(16) yes
C11 . C10 . O17 . 120.36(15) yes
C6 . C11 . C10 . 110.78(12) yes
C6 . C11 . C12 . 111.11(12) yes
C10 . C11 . C12 . 109.01(13) yes
C6 . C11 . H111 . 108.4 no
C10 . C11 . H111 . 105.8 no
C12 . C11 . H111 . 111.5 no
C11 . C12 . O13 . 119.10(14) yes
C11 . C12 . N14 . 119.04(14) yes
O13 . C12 . N14 . 121.86(15) yes
C12 . N14 . C15 . 118.52(14) yes
C12 . N14 . C16 . 125.32(14) yes
C15 . N14 . C16 . 115.40(14) yes
N14 . C15 . H153 . 110.1 no
N14 . C15 . H151 . 109.1 no
H153 . C15 . H151 . 107.0 no
N14 . C15 . H152 . 111.8 no
H153 . C15 . H152 . 110.4 no
H151 . C15 . H152 . 108.3 no
N14 . C16 . H161 . 112.5 no
N14 . C16 . H163 . 108.8 no
H161 . C16 . H163 . 106.4 no
N14 . C16 . H162 . 113.8 no
H161 . C16 . H162 . 109.9 no
H163 . C16 . H162 . 105.0 no
C9 . C18 . C19 . 120.92(17) yes
C9 . C18 . H181 . 119.5 no
C19 . C18 . H181 . 119.6 no
C18 . C19 . C20 . 119.23(17) yes
C18 . C19 . H191 . 121.3 no
C20 . C19 . H191 . 119.4 no
C19 . C20 . C21 . 121.25(17) yes
C19 . C20 . H201 . 119.8 no
C21 . C20 . H201 . 119.0 no
C8 . C21 . C20 . 120.08(16) yes
C8 . C21 . H211 . 119.3 no
C20 . C21 . H211 . 120.6 no
C5 . C22 . C23 . 120.63(16) yes
C5 . C22 . H221 . 119.6 no
C23 . C22 . H221 . 119.8 no
C22 . C23 . C2 . 119.43(17) yes
C22 . C23 . H231 . 120.4 no
C2 . C23 . H231 . 120.2 no
H1 . O1 . H2 . 102.6 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
N7 . H71 . O1 4_545 169.59(6) 0.851 2.045 2.886(2) yes
O1 . H1 . O17 2_666 163.41(5) 0.835 2.059 2.869(2) yes
O1 . H2 . O13 3_464 172.97(6) 0.823 1.925 2.744(2) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 01/02/14 at 00:26:17
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'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 N   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  15,X'S) H   ( 153,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 163,X'S) H   ( 162,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE O   (   1,X'S) H   (   1,X'S) H   (   2,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 01/02/14 at 00:26:17
#
#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 984645'
