# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_mr2
_database_code_depnum_ccdc_archive 'CCDC 1838655'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_audit_creation_date             2018-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H11 N O4'
_chemical_formula_sum            'C7 H11 N O4'
_chemical_formula_weight         173.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7222(3)
_cell_length_b                   7.91107(17)
_cell_length_c                   11.6743(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.086(3)
_cell_angle_gamma                90
_cell_volume                     878.00(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3668
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.2920
_cell_measurement_theta_min      3.8760
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.687
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.334
_diffrn_reflns_theta_min         6.655
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00  40.00   1.00    2.25    --  -42.21   0.00 -30.00  158
  2  ω     -3.00  75.00   1.00    2.25    --   42.21 -99.00 120.00   78
  3  ω     18.00  63.00   1.00    2.25    --   42.21  57.00 120.00   45
  4  ω     55.00 111.00   1.00    2.25    --   42.21  57.00 -90.00   56
  5  ω     33.00  86.00   1.00    2.25    --   42.21-125.00 -90.00   53
  6  ω     87.00 112.00   1.00    2.25    --   42.21  57.00 120.00   25
  7  ω    101.00 131.00   1.00    9.00    --  114.00 111.00 -60.00   30
  8  ω     43.00 105.00   1.00    9.00    --  114.00 -61.00 -90.00   62
  9  ω     90.00 172.00   1.00    9.00    --  114.00  30.00 -90.00   82
 10  ω    135.00 166.00   1.00    9.00    --  114.00 -15.00 -30.00   31
 11  ω    111.00 144.00   1.00    9.00    --  114.00 111.00  60.00   33
 12  ω     41.00 139.00   1.00    9.00    --  114.00 -45.00  90.00   98
 13  ω     54.00 116.00   1.00    9.00    --  114.00-111.00 -90.00   62
 14  ω     59.00 119.00   1.00    9.00    --  114.00 178.00 120.00   60
 15  ω     32.00 106.00   1.00    9.00    --  114.00 -95.00 120.00   74
 16  ω    101.00 159.00   1.00    9.00    --  114.00 111.00  30.00   58
 17  ω    116.00 142.00   1.00    9.00    --  114.00 178.00 -60.00   26
 18  ω     89.00 114.00   1.00    9.00    --  114.00  77.00-150.00   25
 19  ω    118.00 167.00   1.00    9.00    --  114.00  77.00-150.00   49
 20  ω     74.00 108.00   1.00    9.00    --  114.00 -95.00   0.00   34
 21  ω     49.00  84.00   1.00    9.00    --  114.00-102.00  73.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1184105000
_diffrn_orient_matrix_UB_12      0.1062756000
_diffrn_orient_matrix_UB_13      -0.0336372000
_diffrn_orient_matrix_UB_21      0.0440176000
_diffrn_orient_matrix_UB_22      -0.1526208000
_diffrn_orient_matrix_UB_23      -0.0659728000
_diffrn_orient_matrix_UB_31      -0.1015467000
_diffrn_orient_matrix_UB_32      0.0576600000
_diffrn_orient_matrix_UB_33      -0.1127893000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1716
_reflns_number_total             1844
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1844
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+0.1427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
The OH was located in a difference map but placed at a calculated position for refinement.
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C), C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.90180(9) 0.64256(10) 0.24010(7) 0.0352(2) Uani 1 1 d . . . . .
O7 O 0.45236(9) 0.86048(10) 0.17486(8) 0.0385(2) Uani 1 1 d . . . . .
H7 H 0.4921 0.9530 0.1960 0.058 Uiso 1 1 calc GR . . . .
O2 O 0.66683(11) 0.66154(10) 0.06182(7) 0.0399(2) Uani 1 1 d . . . . .
O6 O 0.52091(9) 0.77498(12) 0.41927(8) 0.0416(2) Uani 1 1 d . . . . .
N3 N 0.67274(11) 0.72929(12) 0.17344(8) 0.0330(2) Uani 1 1 d . . . . .
C4 C 0.78789(12) 0.68802(13) 0.25959(10) 0.0295(3) Uani 1 1 d . . . . .
C6 C 0.60812(12) 0.74107(14) 0.34917(10) 0.0310(3) Uani 1 1 d . . . . .
C7 C 0.54238(12) 0.72749(14) 0.21909(10) 0.0318(3) Uani 1 1 d . . . . .
C5 C 0.74767(12) 0.71524(14) 0.37160(10) 0.0306(3) Uani 1 1 d . . . . .
H5 H 0.8089 0.7148 0.4466 0.037 Uiso 1 1 calc R . . . .
C8 C 0.46063(13) 0.56367(15) 0.19043(11) 0.0401(3) Uani 1 1 d . . . . .
H8A H 0.3790 0.5642 0.2275 0.060 Uiso 1 1 calc GR . . . .
H8B H 0.5215 0.4677 0.2200 0.060 Uiso 1 1 calc GR . . . .
H8C H 0.4287 0.5535 0.1053 0.060 Uiso 1 1 calc GR . . . .
C1 C 0.68712(16) 0.79541(16) -0.01591(11) 0.0418(3) Uani 1 1 d . . . . .
H1A H 0.6841 0.7491 -0.0943 0.063 Uiso 1 1 calc GR . . . .
H1B H 0.7787 0.8488 0.0133 0.063 Uiso 1 1 calc GR . . . .
H1C H 0.6124 0.8797 -0.0199 0.063 Uiso 1 1 calc GR . . . .
C9 C 0.58851(17) 0.8005(2) 0.54050(12) 0.0557(4) Uani 1 1 d . . . . .
H9A H 0.6557 0.8941 0.5463 0.084 Uiso 1 1 calc GR . . . .
H9B H 0.6384 0.6972 0.5715 0.084 Uiso 1 1 calc GR . . . .
H9C H 0.5173 0.8276 0.5860 0.084 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C4 1.2302(14) . ?
O7 H7 0.8400 . ?
O7 C7 1.3965(13) . ?
O2 N3 1.3991(12) . ?
O2 C1 1.4349(14) . ?
O6 C6 1.3233(14) . ?
O6 C9 1.4444(17) . ?
N3 C4 1.3783(15) . ?
N3 C7 1.4742(15) . ?
C4 C5 1.4571(15) . ?
C6 C7 1.5231(15) . ?
C6 C5 1.3425(17) . ?
C7 C8 1.5205(16) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O7 H7 109.5 . . ?
N3 O2 C1 108.78(9) . . ?
C6 O6 C9 114.54(10) . . ?
O2 N3 C7 117.53(9) . . ?
C4 N3 O2 117.23(9) . . ?
C4 N3 C7 111.24(9) . . ?
O4 C4 N3 124.01(10) . . ?
O4 C4 C5 129.08(11) . . ?
N3 C4 C5 106.88(9) . . ?
O6 C6 C7 116.20(10) . . ?
O6 C6 C5 131.49(11) . . ?
C5 C6 C7 112.32(10) . . ?
O7 C7 N3 112.26(9) . . ?
O7 C7 C6 114.53(9) . . ?
O7 C7 C8 107.61(9) . . ?
N3 C7 C6 98.44(9) . . ?
N3 C7 C8 112.21(9) . . ?
C8 C7 C6 111.74(10) . . ?
C4 C5 H5 126.3 . . ?
C6 C5 C4 107.31(10) . . ?
C6 C5 H5 126.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O4 0.84 1.88 2.7178(12) 171.9 2_655

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.758
