# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_47
_database_code_depnum_ccdc_archive 'CCDC 1548777'
_audit_update_record             
;
2017-05-09 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             16-06-02
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6570
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   6.3866(1)
_cell_length_b                   10.6043(2)
_cell_length_c                   19.7027(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1334.37(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-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 0.0181 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            4

# Given Formula = C13 H19 N1 O5 
# Dc =      1.34 Fooo =    576.00 Mu =      8.62 M =    269.30
# Found Formula = C13 H19 N1 O5 
# Dc =      1.34 FOOO =    576.00 Mu =      8.62 M =    269.30

_chemical_formula_sum            'C13 H19 N1 O5'
_chemical_formula_moiety         'C13 H19 N1 O5'
_chemical_compound_source        .
_chemical_formula_weight         269.30


_cell_measurement_reflns_used    8811
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_max          0.11

_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.862

# Sheldrick geometric approximatio 0.93 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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            17603
_reflns_number_total             2769
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0468
# Number of reflections without Friedels Law is 2769 
# Number of reflections with Friedels Law is 1627 
# Theoretical number of reflections is about 1395 


_diffrn_reflns_theta_min         4.488
_diffrn_reflns_theta_max         76.120
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        76.120
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -7
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   2.07
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.26


# 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         2758
_refine_ls_number_restraints     0
_refine_ls_number_parameters     173
_oxford_refine_ls_R_factor_ref   0.0280
_refine_ls_wR_factor_ref         0.0669
_refine_ls_goodness_of_fit_ref   1.0034
_refine_ls_shift/su_max          0.0005614
_refine_ls_shift/su_mean         0.0000487


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2758
_refine_ls_R_factor_all          0.0280
_refine_ls_wR_factor_all         0.0669

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2645
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_gt          0.0655

_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_abs_structure_details 'Flack (1983), 1142 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    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) + ( 0.04P)² + 0.20P] 
 ,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
O1 O 0.79129(14) 0.53334(8) 0.62388(5) 0.0265 1.0000 Uani . . . . . .
C2 C 0.58841(19) 0.58686(11) 0.61910(6) 0.0215 1.0000 Uani . . . . . .
N3 N 0.50594(15) 0.53268(9) 0.55486(5) 0.0186 1.0000 Uani . . . . . .
C4 C 0.67098(16) 0.46035(10) 0.52029(6) 0.0186 1.0000 Uani . . . . . .
C5 C 0.86602(19) 0.50922(11) 0.55682(7) 0.0233 1.0000 Uani . . . . . .
C6 C 0.38645(17) 0.59763(10) 0.50886(6) 0.0181 1.0000 Uani . . . . . .
C7 C 0.41217(18) 0.53150(10) 0.44082(6) 0.0202 1.0000 Uani . . . . . .
C8 C 0.64205(18) 0.48611(10) 0.44367(6) 0.0196 1.0000 Uani . . . . . .
C9 C 0.6772(2) 0.35772(11) 0.41036(6) 0.0246 1.0000 Uani . . . . . .
O10 O 0.64565(14) 0.26451(8) 0.46333(5) 0.0265 1.0000 Uani . . . . . .
C11 C 0.65005(18) 0.31680(10) 0.52577(6) 0.0210 1.0000 Uani . . . . . .
O12 O 0.27784(13) 0.69002(8) 0.52100(5) 0.0228 1.0000 Uani . . . . . .
C13 C 0.3527(2) 0.60763(12) 0.37839(6) 0.0283 1.0000 Uani . . . . . .
O14 O 0.78619(14) 0.57098(8) 0.41492(4) 0.0248 1.0000 Uani . . . . . .
O15 O 0.64478(15) 0.25268(8) 0.57589(5) 0.0285 1.0000 Uani . . . . . .
C16 C 0.4640(2) 0.55779(12) 0.68396(6) 0.0257 1.0000 Uani . . . . . .
C17 C 0.2707(2) 0.64310(13) 0.68620(7) 0.0323 1.0000 Uani . . . . . .
C18 C 0.3972(3) 0.41982(13) 0.68680(7) 0.0380 1.0000 Uani . . . . . .
C19 C 0.6049(3) 0.58830(15) 0.74488(7) 0.0381 1.0000 Uani . . . . . .
H21 H 0.5964 0.6801 0.6127 0.0262 1.0000 Uiso R . . . . .
H52 H 0.9129 0.5871 0.5348 0.0266 1.0000 Uiso R . . . . .
H51 H 0.9785 0.4458 0.5585 0.0285 1.0000 Uiso R . . . . .
H71 H 0.3231 0.4571 0.4425 0.0245 1.0000 Uiso R . . . . .
H91 H 0.8210 0.3490 0.3934 0.0279 1.0000 Uiso R . . . . .
H92 H 0.5784 0.3406 0.3743 0.0290 1.0000 Uiso R . . . . .
H132 H 0.3968 0.5618 0.3384 0.0411 1.0000 Uiso R . . . . .
H133 H 0.4175 0.6916 0.3782 0.0408 1.0000 Uiso R . . . . .
H131 H 0.2025 0.6181 0.3761 0.0407 1.0000 Uiso R . . . . .
H171 H 0.1887 0.6263 0.7266 0.0478 1.0000 Uiso R . . . . .
H172 H 0.3089 0.7332 0.6854 0.0480 1.0000 Uiso R . . . . .
H173 H 0.1826 0.6253 0.6484 0.0472 1.0000 Uiso R . . . . .
H181 H 0.3244 0.4044 0.7293 0.0568 1.0000 Uiso R . . . . .
H182 H 0.5168 0.3649 0.6834 0.0564 1.0000 Uiso R . . . . .
H183 H 0.3001 0.4005 0.6484 0.0560 1.0000 Uiso R . . . . .
H191 H 0.5233 0.5788 0.7868 0.0571 1.0000 Uiso R . . . . .
H192 H 0.6571 0.6756 0.7426 0.0563 1.0000 Uiso R . . . . .
H193 H 0.7229 0.5308 0.7461 0.0551 1.0000 Uiso R . . . . .
H141 H 0.7689 0.6403 0.4318 0.0372 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.62(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.4177(15) yes
O1 . C5 . 1.4280(15) yes
C2 . N3 . 1.4865(15) yes
C2 . C16 . 1.5361(16) yes
C2 . H21 . 0.998 no
N3 . C4 . 1.4707(14) yes
N3 . C6 . 1.3705(15) yes
C4 . C5 . 1.5291(16) yes
C4 . C8 . 1.5454(16) yes
C4 . C11 . 1.5319(14) yes
C5 . H52 . 0.980 no
C5 . H51 . 0.984 no
C6 . C7 . 1.5217(15) yes
C6 . O12 . 1.2240(14) yes
C7 . C8 . 1.5461(16) yes
C7 . C13 . 1.5194(16) yes
C7 . H71 . 0.973 no
C8 . C9 . 1.5279(15) yes
C8 . O14 . 1.4065(14) yes
C9 . O10 . 1.4514(15) yes
C9 . H91 . 0.982 no
C9 . H92 . 0.967 no
O10 . C11 . 1.3498(16) yes
C11 . O15 . 1.1994(15) yes
C13 . H132 . 0.968 no
C13 . H133 . 0.982 no
C13 . H131 . 0.967 no
O14 . H141 . 0.814 no
C16 . C17 . 1.5311(19) yes
C16 . C18 . 1.5249(17) yes
C16 . C19 . 1.5349(18) yes
C17 . H171 . 0.970 no
C17 . H172 . 0.987 no
C17 . H173 . 0.953 no
C18 . H181 . 0.972 no
C18 . H182 . 0.963 no
C18 . H183 . 0.999 no
C19 . H191 . 0.982 no
C19 . H192 . 0.985 no
C19 . H193 . 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 . O1 . C5 . 108.41(9) yes
O1 . C2 . N3 . 103.04(9) yes
O1 . C2 . C16 . 109.71(10) yes
N3 . C2 . C16 . 116.58(9) yes
O1 . C2 . H21 . 111.0 no
N3 . C2 . H21 . 107.1 no
C16 . C2 . H21 . 109.3 no
C2 . N3 . C4 . 110.00(9) yes
C2 . N3 . C6 . 124.49(9) yes
C4 . N3 . C6 . 110.79(9) yes
N3 . C4 . C5 . 100.90(9) yes
N3 . C4 . C8 . 105.93(9) yes
C5 . C4 . C8 . 119.82(10) yes
N3 . C4 . C11 . 115.03(9) yes
C5 . C4 . C11 . 112.01(9) yes
C8 . C4 . C11 . 103.53(9) yes
C4 . C5 . O1 . 102.94(9) yes
C4 . C5 . H52 . 109.0 no
O1 . C5 . H52 . 111.2 no
C4 . C5 . H51 . 112.3 no
O1 . C5 . H51 . 109.5 no
H52 . C5 . H51 . 111.6 no
N3 . C6 . C7 . 106.91(9) yes
N3 . C6 . O12 . 126.05(11) yes
C7 . C6 . O12 . 127.03(10) yes
C6 . C7 . C8 . 102.36(9) yes
C6 . C7 . C13 . 116.19(9) yes
C8 . C7 . C13 . 115.59(10) yes
C6 . C7 . H71 . 106.3 no
C8 . C7 . H71 . 107.6 no
C13 . C7 . H71 . 108.2 no
C4 . C8 . C7 . 101.77(9) yes
C4 . C8 . C9 . 104.15(9) yes
C7 . C8 . C9 . 113.66(10) yes
C4 . C8 . O14 . 115.35(10) yes
C7 . C8 . O14 . 114.06(9) yes
C9 . C8 . O14 . 107.52(9) yes
C8 . C9 . O10 . 106.12(9) yes
C8 . C9 . H91 . 111.5 no
O10 . C9 . H91 . 108.1 no
C8 . C9 . H92 . 112.7 no
O10 . C9 . H92 . 108.1 no
H91 . C9 . H92 . 110.1 no
C9 . O10 . C11 . 111.88(9) yes
C4 . C11 . O10 . 110.23(10) yes
C4 . C11 . O15 . 128.59(12) yes
O10 . C11 . O15 . 121.13(10) yes
C7 . C13 . H132 . 108.7 no
C7 . C13 . H133 . 112.3 no
H132 . C13 . H133 . 109.2 no
C7 . C13 . H131 . 110.3 no
H132 . C13 . H131 . 107.9 no
H133 . C13 . H131 . 108.3 no
C8 . O14 . H141 . 108.9 no
C2 . C16 . C17 . 108.82(10) yes
C2 . C16 . C18 . 111.57(10) yes
C17 . C16 . C18 . 109.91(12) yes
C2 . C16 . C19 . 107.74(11) yes
C17 . C16 . C19 . 109.01(11) yes
C18 . C16 . C19 . 109.72(12) yes
C16 . C17 . H171 . 110.5 no
C16 . C17 . H172 . 111.9 no
H171 . C17 . H172 . 109.0 no
C16 . C17 . H173 . 109.7 no
H171 . C17 . H173 . 106.7 no
H172 . C17 . H173 . 109.0 no
C16 . C18 . H181 . 109.1 no
C16 . C18 . H182 . 110.9 no
H181 . C18 . H182 . 109.7 no
C16 . C18 . H183 . 110.0 no
H181 . C18 . H183 . 108.7 no
H182 . C18 . H183 . 108.4 no
C16 . C19 . H191 . 109.0 no
C16 . C19 . H192 . 111.2 no
H191 . C19 . H192 . 108.3 no
C16 . C19 . H193 . 110.1 no
H191 . C19 . H193 . 109.1 no
H192 . C19 . H193 . 109.2 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
C5 . H52 . O12 1_655 132.59 0.980 2.588 3.3303(18) yes
C5 . H51 . O10 3_556 155.68 0.984 2.510 3.4311(18) yes
C7 . H71 . O15 3_456 166.61 0.973 2.526 3.4794(18) yes
C9 . H91 . O15 3_556 139.40 0.982 2.409 3.2190(18) yes
C18 . H182 . O15 . 126.24 0.963 2.564 3.2274(18) yes
O14 . H141 . O12 3_566 170.15 0.814 2.026 2.8320(18) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 02/06/16 at 14:59:18
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 133,X'S) H   ( 131,X'S) 
RIDE O   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 02/06/16 at 14:59:18
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
