# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 1439072'
_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(1,2-dimethyl-3-methylenecyclopropyl)(6-nitrobenzo[d][1,3]dioxol-5-yl)methanol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O5'
_chemical_formula_sum            'C14 H15 N O5'
_chemical_formula_weight         277.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5866(4)
_cell_length_b                   19.5978(6)
_cell_length_c                   7.6285(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.316(5)
_cell_angle_gamma                90.00
_cell_volume                     1335.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5568
_cell_measurement_theta_min      4.7370
_cell_measurement_theta_max      31.7110

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            26741
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.16
_diffrn_reflns_theta_max         30.51
_reflns_number_total             4061
_reflns_number_gt                3152
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0621P)²+0.2066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C5 C -0.05969(12) 0.16628(5) 0.16986(15) 0.0202(2) Uani 1 1 d . . .
O5 O -0.24491(10) 0.20427(4) -0.12769(12) 0.02597(19) Uani 1 1 d . . .
C3 C 0.19694(13) 0.18092(6) 0.20945(17) 0.0250(2) Uani 1 1 d . . .
N1 N -0.11690(11) 0.14947(5) 0.46035(13) 0.0246(2) Uani 1 1 d . . .
C8 C -0.22251(12) 0.16412(6) 0.03726(15) 0.0215(2) Uani 1 1 d . . .
H8 H -0.2831(9) 0.1856(3) 0.1049(10) 0.026 Uiso 1 1 calc R . .
O4 O -0.24377(10) 0.12962(5) 0.36987(13) 0.0320(2) Uani 1 1 d . . .
O2 O 0.39397(10) 0.17956(5) 0.48394(13) 0.0364(2) Uani 1 1 d . . .
O3 O -0.07357(12) 0.16088(5) 0.63143(12) 0.0370(2) Uani 1 1 d . . .
C12 C -0.19861(14) 0.03158(6) 0.07658(18) 0.0289(3) Uani 1 1 d . . .
C6 C -0.01067(12) 0.15961(6) 0.36649(15) 0.0211(2) Uani 1 1 d . . .
C7 C 0.14001(13) 0.16413(6) 0.48702(16) 0.0254(2) Uani 1 1 d . . .
H7 H 0.1699(5) 0.15998(9) 0.622(2) 0.031 Uiso 1 1 calc R . .
O1 O 0.31926(10) 0.19026(5) 0.16101(14) 0.0357(2) Uani 1 1 d . . .
C4 C 0.05016(13) 0.17784(6) 0.09182(16) 0.0231(2) Uani 1 1 d . . .
H4 H 0.0219(5) 0.18364(11) -0.046(2) 0.028 Uiso 1 1 calc R . .
C11 C -0.19622(17) 0.04687(6) -0.11025(19) 0.0333(3) Uani 1 1 d . . .
H11 H -0.1006(16) 0.0676(4) -0.10776(19) 0.040 Uiso 1 1 calc R . .
C2 C 0.24168(13) 0.17471(6) 0.40303(17) 0.0257(2) Uani 1 1 d . . .
C9 C -0.28376(13) 0.09206(6) -0.01776(16) 0.0247(2) Uani 1 1 d . . .
C13 C -0.16314(17) -0.01072(7) 0.2194(2) 0.0397(3) Uani 1 1 d . . .
H13A H -0.1113(7) -0.0529(6) 0.2163(2) 0.048 Uiso 1 1 calc R . .
H13B H -0.1887(4) 0.00023(15) 0.3280(14) 0.048 Uiso 1 1 calc R . .
C10 C -0.45295(15) 0.08895(8) -0.0908(2) 0.0384(3) Uani 1 1 d . . .
H10A H -0.4948(5) 0.1200(5) -0.2017(16) 0.058 Uiso 1 1 calc R . .
H10B H -0.4895(4) 0.1037(6) 0.0107(12) 0.058 Uiso 1 1 calc R . .
H10C H -0.4865(4) 0.0411(5) -0.1296(15) 0.058 Uiso 1 1 calc R . .
C1 C 0.44138(16) 0.19975(11) 0.3362(2) 0.0529(5) Uani 1 1 d . . .
H1A H 0.5278(13) 0.1720(4) 0.3386(2) 0.063 Uiso 1 1 calc R . .
H1B H 0.4720(5) 0.2480(7) 0.3515(3) 0.063 Uiso 1 1 calc R . .
C14 C -0.2721(2) 0.00252(8) -0.2798(2) 0.0557(5) Uani 1 1 d . . .
H14A H -0.3075(15) 0.0309(4) -0.3928(15) 0.084 Uiso 1 1 calc R . .
H14B H -0.3570(14) -0.0209(6) -0.2648(9) 0.084 Uiso 1 1 calc R . .
H14C H -0.2008(10) -0.0312(6) -0.2916(12) 0.084 Uiso 1 1 calc R . .
H5 H -0.222(2) 0.1789(10) -0.204(3) 0.045(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C5 C4 1.4037(15) . ?
C5 C6 1.4055(15) . ?
C5 C8 1.5211(15) . ?
O5 C8 1.4325(13) . ?
O5 H5 0.851(19) . ?
C3 O1 1.3638(14) . ?
C3 C4 1.3678(16) . ?
C3 C2 1.3853(17) . ?
N1 O4 1.2235(13) . ?
N1 O3 1.2376(13) . ?
N1 C6 1.4558(14) . ?
C8 C9 1.5283(16) . ?
C8 H8 0.9990 . ?
O2 C2 1.3661(14) . ?
O2 C1 1.4160(19) . ?
C12 C13 1.3115(18) . ?
C12 C11 1.4647(18) . ?
C12 C9 1.4705(17) . ?
C6 C7 1.4051(16) . ?
C7 C2 1.3630(17) . ?
C7 H7 0.9663 . ?
O1 C1 1.4332(19) . ?
C4 H4 0.9900 . ?
C11 C14 1.508(2) . ?
C11 C9 1.5546(17) . ?
C11 H11 0.9962 . ?
C9 C10 1.5126(17) . ?
C13 H13A 0.9696 . ?
C13 H13B 0.9696 . ?
C10 H10A 1.0008 . ?
C10 H10B 1.0008 . ?
C10 H10C 1.0008 . ?
C1 H1A 0.9850 . ?
C1 H1B 0.9850 . ?
C14 H14A 0.9773 . ?
C14 H14B 0.9773 . ?
C14 H14C 0.9773 . ?

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
C4 C5 C6 117.15(10) . . ?
C4 C5 C8 117.98(9) . . ?
C6 C5 C8 124.84(10) . . ?
C8 O5 H5 106.5(12) . . ?
O1 C3 C4 127.51(11) . . ?
O1 C3 C2 109.70(10) . . ?
C4 C3 C2 122.79(11) . . ?
O4 N1 O3 122.42(10) . . ?
O4 N1 C6 119.71(9) . . ?
O3 N1 C6 117.87(10) . . ?
O5 C8 C5 111.03(9) . . ?
O5 C8 C9 110.27(9) . . ?
C5 C8 C9 114.03(9) . . ?
O5 C8 H8 107.0 . . ?
C5 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
C2 O2 C1 105.03(10) . . ?
C13 C12 C11 147.83(13) . . ?
C13 C12 C9 147.80(13) . . ?
C11 C12 C9 63.96(9) . . ?
C7 C6 C5 123.91(10) . . ?
C7 C6 N1 115.04(10) . . ?
C5 C6 N1 121.02(10) . . ?
C2 C7 C6 116.28(10) . . ?
C2 C7 H7 121.9 . . ?
C6 C7 H7 121.9 . . ?
C3 O1 C1 104.83(10) . . ?
C3 C4 C5 118.71(10) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C12 C11 C14 122.91(12) . . ?
C12 C11 C9 58.20(8) . . ?
C14 C11 C9 123.10(14) . . ?
C12 C11 H11 113.9 . . ?
C14 C11 H11 113.9 . . ?
C9 C11 H11 113.9 . . ?
C7 C2 O2 128.87(11) . . ?
C7 C2 C3 121.15(11) . . ?
O2 C2 C3 109.97(10) . . ?
C12 C9 C10 118.55(10) . . ?
C12 C9 C8 121.40(10) . . ?
C10 C9 C8 113.07(10) . . ?
C12 C9 C11 57.84(8) . . ?
C10 C9 C11 119.57(11) . . ?
C8 C9 C11 115.73(10) . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C1 O1 108.44(11) . . ?
O2 C1 H1A 110.0 . . ?
O1 C1 H1A 110.0 . . ?
O2 C1 H1B 110.0 . . ?
O1 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C5 C8 O5 -27.15(14) . . . . ?
C6 C5 C8 O5 150.80(10) . . . . ?
C4 C5 C8 C9 98.13(12) . . . . ?
C6 C5 C8 C9 -83.91(13) . . . . ?
C4 C5 C6 C7 0.28(16) . . . . ?
C8 C5 C6 C7 -177.68(10) . . . . ?
C4 C5 C6 N1 178.24(10) . . . . ?
C8 C5 C6 N1 0.27(17) . . . . ?
O4 N1 C6 C7 -163.42(11) . . . . ?
O3 N1 C6 C7 15.86(15) . . . . ?
O4 N1 C6 C5 18.45(16) . . . . ?
O3 N1 C6 C5 -162.26(10) . . . . ?
C5 C6 C7 C2 -0.93(17) . . . . ?
N1 C6 C7 C2 -179.00(10) . . . . ?
C4 C3 O1 C1 171.55(14) . . . . ?
C2 C3 O1 C1 -8.34(15) . . . . ?
O1 C3 C4 C5 178.58(11) . . . . ?
C2 C3 C4 C5 -1.55(18) . . . . ?
C6 C5 C4 C3 0.94(16) . . . . ?
C8 C5 C4 C3 179.06(10) . . . . ?
C13 C12 C11 C14 61.5(3) . . . . ?
C9 C12 C11 C14 -111.36(17) . . . . ?
C13 C12 C11 C9 172.8(3) . . . . ?
C6 C7 C2 O2 -178.35(11) . . . . ?
C6 C7 C2 C3 0.36(17) . . . . ?
C1 O2 C2 C7 -172.28(14) . . . . ?
C1 O2 C2 C3 8.90(15) . . . . ?
O1 C3 C2 C7 -179.22(11) . . . . ?
C4 C3 C2 C7 0.88(19) . . . . ?
O1 C3 C2 O2 -0.29(14) . . . . ?
C4 C3 C2 O2 179.81(11) . . . . ?
C13 C12 C9 C10 -64.1(3) . . . . ?
C11 C12 C9 C10 108.75(13) . . . . ?
C13 C12 C9 C8 84.6(3) . . . . ?
C11 C12 C9 C8 -102.54(12) . . . . ?
C13 C12 C9 C11 -172.9(3) . . . . ?
O5 C8 C9 C12 135.55(11) . . . . ?
C5 C8 C9 C12 9.85(15) . . . . ?
O5 C8 C9 C10 -74.18(12) . . . . ?
C5 C8 C9 C10 160.13(10) . . . . ?
O5 C8 C9 C11 69.01(13) . . . . ?
C5 C8 C9 C11 -56.68(13) . . . . ?
C14 C11 C9 C12 111.03(15) . . . . ?
C12 C11 C9 C10 -107.00(12) . . . . ?
C14 C11 C9 C10 4.03(18) . . . . ?
C12 C11 C9 C8 112.34(11) . . . . ?
C14 C11 C9 C8 -136.63(13) . . . . ?
C2 O2 C1 O1 -14.03(17) . . . . ?
C3 O1 C1 O2 13.87(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048

