# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1403819'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

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

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.6565(9)
_cell_length_b                   5.2736(4)
_cell_length_c                   13.0287(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.783(6)
_cell_angle_gamma                90
_cell_volume                     777.83(11)

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

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


_cell_formula_units_Z            2

# Given Formula = C16 H16 N1 O5 
# Dc =      1.29 Fooo =    316.00 Mu =      8.08 M =    302.31
# Found Formula = C17 H17 N1 O4 
# Dc =      1.28 FOOO =    316.00 Mu =      7.53 M =    299.33

_chemical_formula_sum            'C17 H17 N1 O4'
_chemical_formula_moiety         'C17 H17 N1 O4'
_chemical_compound_source        ?
_chemical_formula_weight         299.33


_cell_measurement_reflns_used    985
_cell_measurement_theta_min      3
_cell_measurement_theta_max      59
_cell_measurement_temperature    200

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_max          0.080

_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.753

# Sheldrick geometric approximatio 0.96 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.96
_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           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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      200
_diffrn_reflns_number            3892
_reflns_number_total             2106
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections without Friedels Law is 2106 
# Number of reflections with Friedels Law is 1239 
# Theoretical number of reflections is about 1123 


_diffrn_reflns_theta_min         3.493
_diffrn_reflns_theta_max         59.092
_diffrn_measured_fraction_theta_max 0.983

_diffrn_reflns_theta_full        59.092
_diffrn_measured_fraction_theta_full 0.983


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -5
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.76
_oxford_diffrn_Wilson_scale      9.24

_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         0.23


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_refine_ls_number_reflns         2103
_refine_ls_number_restraints     2
_refine_ls_number_parameters     203
_oxford_refine_ls_R_factor_ref   0.0652
_refine_ls_wR_factor_ref         0.1231
_refine_ls_goodness_of_fit_ref   0.9841
_refine_ls_shift/su_max          0.0021021
_refine_ls_shift/su_mean         0.0001733


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2103
_refine_ls_R_factor_all          0.0652
_refine_ls_wR_factor_all         0.1231

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1691
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_gt          0.1113

_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_abs_structure_details 'Flack (1983), 867 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 3.65 4.53 1.26 
;

# 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 0.6194(3) 0.5228(8) 0.2247(3) 0.0306 1.0000 Uani . . . . . .
C2 C 0.5000(3) 0.5822(7) 0.1571(3) 0.0282 1.0000 Uani . . . . . .
C3 C 0.4361(4) 0.7965(8) 0.1712(3) 0.0390 1.0000 Uani . . . . . .
C4 C 0.3239(4) 0.8349(9) 0.1081(4) 0.0464 1.0000 Uani . . . . . .
C5 C 0.2762(4) 0.6664(9) 0.0286(4) 0.0475 1.0000 Uani . . . . . .
C6 C 0.3394(4) 0.4554(8) 0.0138(3) 0.0436 1.0000 Uani . . . . . .
C7 C 0.4506(4) 0.4106(8) 0.0777(3) 0.0365 1.0000 Uani . . . . . .
C8 C 0.8073(4) 0.6881(8) 0.3260(3) 0.0346 1.0000 Uani . . . . . .
C9 C 0.8943(4) 0.7089(9) 0.2556(3) 0.0434 1.0000 Uani . . . . . .
C10 C 1.0585(7) 0.522(2) 0.2113(7) 0.1247 1.0000 Uani . . . . . .
C11 C 0.8365(3) 0.8862(7) 0.4135(3) 0.0318 1.0000 Uani . . . . . .
C12 C 0.7590(3) 0.8584(7) 0.4919(3) 0.0313 1.0000 Uani . . . . . .
C13 C 0.7772(5) 0.6543(9) 0.5613(4) 0.0529 1.0000 Uani . . . . . .
C14 C 0.7061(5) 0.6296(10) 0.6335(4) 0.0593 1.0000 Uani . . . . . .
C15 C 0.6208(5) 0.8033(10) 0.6370(4) 0.0535 1.0000 Uani . . . . . .
C16 C 0.6024(4) 1.0047(10) 0.5684(4) 0.0559 1.0000 Uani . . . . . .
C17 C 0.6721(4) 1.0312(9) 0.4948(4) 0.0463 1.0000 Uani . . . . . .
O1 O 0.6527(3) 0.3031(5) 0.2428(2) 0.0433 1.0000 Uani . . . . . .
O2 O 0.8913(3) 0.8705(8) 0.1921(3) 0.0727 1.0000 Uani . . . . . .
O3 O 0.9710(3) 0.5193(8) 0.2745(3) 0.0761 1.0000 Uani . . . . . .
O4 O 0.9589(2) 0.8536(6) 0.4623(2) 0.0384 1.0000 Uani D . . . . .
N1 N 0.6874(3) 0.7237(6) 0.2642(3) 0.0342 1.0000 Uani . . . . . .
H1 H 0.6600 0.8900 0.2428 0.064(4) 1.0000 Uiso . . . . . .
H4 H 0.988(5) 0.965(10) 0.487(4) 0.064(4) 1.0000 Uiso D . . . . .
H31 H 0.4715 0.9138 0.2257 0.064(4) 1.0000 Uiso . . . . . .
H41 H 0.2807 0.9818 0.1207 0.064(4) 1.0000 Uiso . . . . . .
H51 H 0.1999 0.6943 -0.0181 0.064(4) 1.0000 Uiso . . . . . .
H61 H 0.3072 0.3360 -0.0398 0.064(4) 1.0000 Uiso . . . . . .
H71 H 0.4939 0.2616 0.0667 0.064(4) 1.0000 Uiso . . . . . .
H81 H 0.8147 0.5147 0.3612 0.064(4) 1.0000 Uiso . . . . . .
H101 H 1.1259 0.4101 0.2426 0.064(4) 1.0000 Uiso . . . . . .
H102 H 1.0892 0.6952 0.2071 0.064(4) 1.0000 Uiso . . . . . .
H103 H 1.0231 0.4654 0.1392 0.064(4) 1.0000 Uiso . . . . . .
H111 H 0.8247 1.0574 0.3788 0.064(4) 1.0000 Uiso . . . . . .
H131 H 0.8368 0.5378 0.5607 0.064(4) 1.0000 Uiso . . . . . .
H141 H 0.7191 0.4867 0.6826 0.064(4) 1.0000 Uiso . . . . . .
H151 H 0.5726 0.7872 0.6878 0.064(4) 1.0000 Uiso . . . . . .
H161 H 0.5425 1.1268 0.5705 0.064(4) 1.0000 Uiso . . . . . .
H171 H 0.6580 1.1727 0.4458 0.064(4) 1.0000 Uiso . . . . . .
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 0.038(2) 0.026(2) 0.0270(19) -0.0005(18) 0.0064(17) -0.0006(19)
C2 0.031(2) 0.023(2) 0.028(2) 0.0014(16) 0.0007(17) -0.0039(15)
C3 0.038(2) 0.030(2) 0.044(2) -0.0024(19) 0.0004(19) -0.0013(19)
C4 0.041(2) 0.040(2) 0.056(3) -0.001(2) 0.007(2) 0.005(2)
C5 0.038(3) 0.052(3) 0.047(3) 0.005(2) -0.002(2) -0.003(2)
C6 0.053(3) 0.039(3) 0.033(2) -0.008(2) 0.000(2) -0.009(2)
C7 0.042(2) 0.034(2) 0.030(2) -0.0050(18) 0.0018(18) -0.0056(19)
C8 0.035(2) 0.036(2) 0.028(2) -0.0006(19) -0.0020(18) -0.0010(18)
C9 0.042(3) 0.048(3) 0.034(2) 0.002(2) -0.0014(19) 0.010(2)
C10 0.100(5) 0.163(9) 0.132(6) 0.011(7) 0.070(5) 0.061(6)
C11 0.032(2) 0.025(2) 0.034(2) 0.0005(17) -0.0027(16) 0.0022(17)
C12 0.036(2) 0.023(2) 0.033(2) -0.0016(17) 0.0030(17) -0.0006(17)
C13 0.063(3) 0.045(3) 0.057(3) 0.014(2) 0.026(3) 0.016(2)
C14 0.079(4) 0.042(3) 0.062(3) 0.014(3) 0.028(3) 0.010(3)
C15 0.068(3) 0.040(2) 0.060(3) 0.001(2) 0.031(3) 0.000(2)
C16 0.063(3) 0.045(3) 0.065(3) 0.004(3) 0.028(3) 0.013(3)
C17 0.061(3) 0.032(2) 0.046(2) 0.002(2) 0.014(2) 0.010(2)
O1 0.0476(17) 0.0243(17) 0.0498(18) 0.0013(14) -0.0048(14) 0.0005(13)
O2 0.068(2) 0.096(3) 0.059(2) 0.028(2) 0.0258(18) 0.023(2)
O3 0.069(2) 0.081(3) 0.085(3) 0.013(2) 0.033(2) 0.039(2)
O4 0.0298(15) 0.0369(18) 0.0415(17) -0.0043(15) -0.0052(12) -0.0037(13)
N1 0.036(2) 0.0241(18) 0.0375(19) -0.0020(15) -0.0017(16) 0.0025(15)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3715(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 . 1.493(5) yes
C1 . O1 . 1.226(5) yes
C1 . N1 . 1.349(5) yes
C2 . C3 . 1.389(6) yes
C2 . C7 . 1.391(5) yes
C3 . C4 . 1.384(6) yes
C3 . H31 . 0.958 no
C4 . C5 . 1.378(6) yes
C4 . H41 . 0.959 no
C5 . C6 . 1.373(7) yes
C5 . H51 . 0.962 no
C6 . C7 . 1.384(6) yes
C6 . H61 . 0.948 no
C7 . H71 . 0.964 no
C8 . C9 . 1.525(6) yes
C8 . C11 . 1.524(5) yes
C8 . N1 . 1.450(5) yes
C8 . H81 . 1.018 no
C9 . O2 . 1.182(6) yes
C9 . O3 . 1.324(6) yes
C10 . O3 . 1.455(7) yes
C10 . H101 . 0.990 no
C10 . H102 . 0.987 no
C10 . H103 . 0.978 no
C11 . C12 . 1.523(6) yes
C11 . O4 . 1.427(4) yes
C11 . H111 . 1.005 no
C12 . C13 . 1.389(6) yes
C12 . C17 . 1.370(6) yes
C13 . C14 . 1.400(7) yes
C13 . H131 . 0.929 no
C14 . C15 . 1.361(7) yes
C14 . H141 . 0.978 no
C15 . C16 . 1.372(7) yes
C15 . H151 . 0.968 no
C16 . C17 . 1.403(7) yes
C16 . H161 . 0.955 no
C17 . H171 . 0.971 no
O4 . H4 . 0.72(5) no
N1 . H1 . 0.952 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 . O1 . 121.3(3) yes
C2 . C1 . N1 . 116.1(3) yes
O1 . C1 . N1 . 122.6(4) yes
C1 . C2 . C3 . 123.1(3) yes
C1 . C2 . C7 . 117.7(3) yes
C3 . C2 . C7 . 119.2(4) yes
C2 . C3 . C4 . 120.1(4) yes
C2 . C3 . H31 . 118.3 no
C4 . C3 . H31 . 121.7 no
C3 . C4 . C5 . 120.5(4) yes
C3 . C4 . H41 . 118.5 no
C5 . C4 . H41 . 121.0 no
C4 . C5 . C6 . 119.6(4) yes
C4 . C5 . H51 . 121.6 no
C6 . C5 . H51 . 118.8 no
C5 . C6 . C7 . 120.7(4) yes
C5 . C6 . H61 . 120.7 no
C7 . C6 . H61 . 118.6 no
C2 . C7 . C6 . 119.9(4) yes
C2 . C7 . H71 . 120.2 no
C6 . C7 . H71 . 119.9 no
C9 . C8 . C11 . 109.8(3) yes
C9 . C8 . N1 . 110.4(3) yes
C11 . C8 . N1 . 109.9(3) yes
C9 . C8 . H81 . 109.8 no
C11 . C8 . H81 . 107.4 no
N1 . C8 . H81 . 109.5 no
C8 . C9 . O2 . 124.0(4) yes
C8 . C9 . O3 . 110.5(4) yes
O2 . C9 . O3 . 125.5(5) yes
O3 . C10 . H101 . 110.9 no
O3 . C10 . H102 . 110.7 no
H101 . C10 . H102 . 108.2 no
O3 . C10 . H103 . 110.3 no
H101 . C10 . H103 . 109.0 no
H102 . C10 . H103 . 107.7 no
C8 . C11 . C12 . 111.9(3) yes
C8 . C11 . O4 . 105.8(3) yes
C12 . C11 . O4 . 112.3(3) yes
C8 . C11 . H111 . 107.3 no
C12 . C11 . H111 . 110.4 no
O4 . C11 . H111 . 108.9 no
C11 . C12 . C13 . 119.2(4) yes
C11 . C12 . C17 . 121.0(3) yes
C13 . C12 . C17 . 119.7(4) yes
C12 . C13 . C14 . 119.1(4) yes
C12 . C13 . H131 . 120.4 no
C14 . C13 . H131 . 120.5 no
C13 . C14 . C15 . 121.0(5) yes
C13 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 119.8 no
C14 . C15 . C16 . 120.1(5) yes
C14 . C15 . H151 . 120.7 no
C16 . C15 . H151 . 119.2 no
C15 . C16 . C17 . 119.7(4) yes
C15 . C16 . H161 . 120.3 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . C12 . 120.4(4) yes
C16 . C17 . H171 . 119.4 no
C12 . C17 . H171 . 120.2 no
C10 . O3 . C9 . 114.9(5) yes
C11 . O4 . H4 . 115(5) no
C8 . N1 . C1 . 120.7(3) yes
C8 . N1 . H1 . 119.6 no
C1 . N1 . H1 . 119.1 no


