# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_mo_201127_lsr_c_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2241047'
loop_
_audit_author_name
_audit_author_address
'Shuangrong Liu'
;Zhejiang University
China
;
_audit_update_record             
;
2023-02-10 deposited with the CCDC.	2023-05-28 downloaded from the CCDC.
;
_audit_creation_date             2020-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H10 N2 O4'
_chemical_formula_sum            'C7 H10 N2 O4'
_chemical_formula_weight         186.17
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.300(2)
_cell_length_b                   5.2776(15)
_cell_length_c                   11.714(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.493(14)
_cell_angle_gamma                90
_cell_volume                     430.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1127 before and 0.0319 after correction.
The Ratio of minimum to maximum transmission is 0.9241.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4860
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.067
_diffrn_reflns_theta_min         2.926
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.795
_reflns_number_gt                1688
_reflns_number_total             1719
_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       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.154
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 657 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1719
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+0.0540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0619
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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
O1 O 0.00597(17) 0.7460(2) 0.12083(9) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.00920(14) 0.3151(2) 0.35998(8) 0.0231(2) Uani 1 1 d . . . . .
O3 O 0.48151(16) 0.7662(3) 0.62468(9) 0.0328(3) Uani 1 1 d . . . . .
O4 O 0.38345(14) 0.4106(2) 0.69606(9) 0.0234(2) Uani 1 1 d . . . . .
N1 N 0.00573(18) 0.3159(3) 0.12941(10) 0.0250(3) Uani 1 1 d . . . . .
H1A H -0.000154 0.299032 0.053647 0.030 Uiso 1 1 calc R . . . .
H1B H 0.008888 0.180747 0.173927 0.030 Uiso 1 1 calc R . . . .
N2 N 0.13570(16) 0.3162(2) 0.47867(9) 0.0203(2) Uani 1 1 d . . . . .
C1 C 0.00984(18) 0.5448(3) 0.17641(11) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.01425(19) 0.5652(3) 0.30691(12) 0.0198(3) Uani 1 1 d . . . . .
H2 H -0.099777 0.664926 0.311502 0.024 Uiso 1 1 calc R . . . .
C3 C 0.1976(2) 0.6913(3) 0.38741(11) 0.0210(3) Uani 1 1 d . . . . .
H3A H 0.303752 0.686229 0.351090 0.025 Uiso 1 1 calc R . . . .
H3B H 0.174511 0.868532 0.407145 0.025 Uiso 1 1 calc R . . . .
C4 C 0.23456(18) 0.5207(3) 0.49401(11) 0.0174(3) Uani 1 1 d . . . . .
C5 C 0.37998(19) 0.5819(3) 0.61118(12) 0.0201(3) Uani 1 1 d . . . . .
C6 C 0.5197(2) 0.4612(3) 0.81358(13) 0.0272(3) Uani 1 1 d . . . . .
H6A H 0.480290 0.613677 0.849551 0.033 Uiso 1 1 calc R . . . .
H6B H 0.649744 0.490309 0.806453 0.033 Uiso 1 1 calc R . . . .
C7 C 0.5194(2) 0.2323(4) 0.88992(14) 0.0384(4) Uani 1 1 d . . . . .
H7A H 0.549494 0.081079 0.850443 0.058 Uiso 1 1 calc GR . . . .
H7B H 0.392334 0.212978 0.901048 0.058 Uiso 1 1 calc GR . . . .
H7C H 0.616168 0.253710 0.968028 0.058 Uiso 1 1 calc GR . . . .

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
O1 0.0434(6) 0.0214(6) 0.0191(5) 0.0027(4) 0.0110(4) 0.0017(5)
O2 0.0291(5) 0.0235(6) 0.0151(4) 0.0022(4) 0.0044(4) -0.0058(4)
O3 0.0384(6) 0.0289(7) 0.0277(6) 0.0018(4) 0.0050(4) -0.0144(5)
O4 0.0263(5) 0.0241(6) 0.0171(5) 0.0027(4) 0.0023(4) -0.0056(4)
N1 0.0383(7) 0.0213(7) 0.0159(5) 0.0002(5) 0.0086(5) 0.0016(6)
N2 0.0247(5) 0.0211(6) 0.0148(5) 0.0002(5) 0.0057(4) -0.0011(5)
C1 0.0205(6) 0.0227(8) 0.0161(6) 0.0016(5) 0.0054(5) 0.0025(5)
C2 0.0243(6) 0.0183(7) 0.0175(6) 0.0017(5) 0.0074(5) 0.0030(6)
C3 0.0314(7) 0.0147(7) 0.0171(6) 0.0017(5) 0.0075(5) -0.0008(5)
C4 0.0219(6) 0.0162(7) 0.0164(6) 0.0015(5) 0.0090(5) 0.0018(5)
C5 0.0218(6) 0.0207(8) 0.0188(6) -0.0004(5) 0.0074(5) -0.0001(5)
C6 0.0301(7) 0.0302(9) 0.0175(7) -0.0018(6) 0.0014(5) -0.0038(6)
C7 0.0396(9) 0.0458(13) 0.0235(7) 0.0091(8) 0.0001(6) -0.0067(8)

_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
O1 C1 1.242(2) . ?
O2 N2 1.4192(14) . ?
O2 C2 1.4641(18) . ?
O3 C5 1.2041(19) . ?
O4 C5 1.3383(17) . ?
O4 C6 1.4602(17) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.324(2) . ?
N2 C4 1.2806(19) . ?
C1 C2 1.5231(18) . ?
C2 H2 1.0000 . ?
C2 C3 1.538(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.4968(19) . ?
C4 C5 1.4964(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.503(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
N2 O2 C2 108.67(10) . . ?
C5 O4 C6 115.61(11) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C4 N2 O2 108.32(11) . . ?
O1 C1 N1 124.62(12) . . ?
O1 C1 C2 117.15(13) . . ?
N1 C1 C2 118.20(13) . . ?
O2 C2 C1 111.53(12) . . ?
O2 C2 H2 108.9 . . ?
O2 C2 C3 104.97(10) . . ?
C1 C2 H2 108.9 . . ?
C1 C2 C3 113.44(11) . . ?
C3 C2 H2 108.9 . . ?
C2 C3 H3A 112.0 . . ?
C2 C3 H3B 112.0 . . ?
H3A C3 H3B 109.7 . . ?
C4 C3 C2 99.00(11) . . ?
C4 C3 H3A 112.0 . . ?
C4 C3 H3B 112.0 . . ?
N2 C4 C3 115.94(12) . . ?
N2 C4 C5 121.67(12) . . ?
C5 C4 C3 122.39(13) . . ?
O3 C5 O4 125.07(13) . . ?
O3 C5 C4 122.26(13) . . ?
O4 C5 C4 112.67(12) . . ?
O4 C6 H6A 110.3 . . ?
O4 C6 H6B 110.3 . . ?
O4 C6 C7 106.94(13) . . ?
H6A C6 H6B 108.6 . . ?
C7 C6 H6A 110.3 . . ?
C7 C6 H6B 110.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_shelx_res_file                  
;
TITL mo_201127_lsr_c_1_0m_a.res in P2(1)
    mo_201127_lsr_c_1_0m.res
    created by SHELXL-2018/3 at 15:59:22 on 27-Nov-2020
REM Old TITL mo_201127_LSR_C_1_0m in P2(1)
REM SHELXT solution in P2(1): R1 0.091, Rweak 0.025, Alpha 0.003
REM <I/s> 3.312 for 3 systematic absences, Orientation as input
REM Flack x = 0.479 ( 0.258 ) from 626 Parsons' quotients
REM Formula found by SHELXT: C7 N2 O4
CELL 0.71073 7.3001 5.2776 11.7137 90 107.493 90
ZERR 2 0.0024 0.0015 0.0033 0 0.014 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 14 20 4 8

L.S. 4 0 0
PLAN  20
SIZE 0.2 0.23 0.36
TEMP -103.15
BOND $h
htab
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\mo_201127_LSR_C_1_0m.hkl">
REM </olex2.extras>

WGHT    0.034400    0.054000
FVAR       1.49077
O1    4    0.005973    0.746050    0.120831    11.00000    0.04337    0.02138 =
         0.01910    0.00273    0.01096    0.00169
O2    4    0.009204    0.315064    0.359978    11.00000    0.02910    0.02352 =
         0.01509    0.00223    0.00437   -0.00577
O3    4    0.481510    0.766165    0.624676    11.00000    0.03844    0.02893 =
         0.02773    0.00180    0.00502   -0.01435
O4    4    0.383452    0.410605    0.696061    11.00000    0.02628    0.02412 =
         0.01710    0.00269    0.00229   -0.00560
N1    3    0.005733    0.315947    0.129406    11.00000    0.03833    0.02126 =
         0.01586    0.00023    0.00860    0.00163
AFIX  93
H1A   2   -0.000154    0.299032    0.053647    11.00000   -1.20000
H1B   2    0.008888    0.180747    0.173927    11.00000   -1.20000
AFIX   0
N2    3    0.135705    0.316192    0.478672    11.00000    0.02474    0.02110 =
         0.01483    0.00024    0.00568   -0.00110
C1    1    0.009844    0.544828    0.176409    11.00000    0.02054    0.02272 =
         0.01609    0.00157    0.00545    0.00248
C2    1    0.014254    0.565155    0.306912    11.00000    0.02428    0.01831 =
         0.01745    0.00170    0.00741    0.00305
AFIX  13
H2    2   -0.099777    0.664926    0.311502    11.00000   -1.20000
AFIX   0
C3    1    0.197622    0.691317    0.387408    11.00000    0.03137    0.01472 =
         0.01706    0.00171    0.00754   -0.00080
AFIX  23
H3A   2    0.303752    0.686229    0.351090    11.00000   -1.20000
H3B   2    0.174511    0.868532    0.407145    11.00000   -1.20000
AFIX   0
C4    1    0.234563    0.520694    0.494008    11.00000    0.02189    0.01617 =
         0.01636    0.00149    0.00904    0.00183
C5    1    0.379985    0.581870    0.611180    11.00000    0.02180    0.02067 =
         0.01876   -0.00039    0.00738   -0.00007
C6    1    0.519651    0.461240    0.813581    11.00000    0.03008    0.03021 =
         0.01752   -0.00181    0.00139   -0.00381
AFIX  23
H6A   2    0.480290    0.613677    0.849551    11.00000   -1.20000
H6B   2    0.649744    0.490309    0.806453    11.00000   -1.20000
AFIX   0
C7    1    0.519389    0.232329    0.889919    11.00000    0.03960    0.04584 =
         0.02348    0.00913    0.00008   -0.00668
AFIX 137
H7A   2    0.549494    0.081079    0.850443    11.00000   -1.50000
H7B   2    0.392334    0.212978    0.901048    11.00000   -1.50000
H7C   2    0.616168    0.253710    0.968028    11.00000   -1.50000
AFIX   0
HKLF 4




REM  mo_201127_lsr_c_1_0m_a.res in P2(1)
REM wR2 = 0.0619, GooF = S = 1.075, Restrained GooF = 1.075 for all data
REM R1 = 0.0237 for 1688 Fo > 4sig(Fo) and 0.0242 for all 1719 data
REM 119 parameters refined using 1 restraints

END

WGHT      0.0335      0.0562

REM Instructions for potential hydrogen bonds
EQIV $1 -x, y-1/2, -z
HTAB N1 O1_$1
EQIV $2 x, y-1, z
HTAB N1 O1_$2
EQIV $3 -x, y+1/2, -z+1
HTAB C2 O4_$3
HTAB C2 N2_$3
EQIV $4 x, y+1, z
HTAB C3 O2_$4
HTAB C3 N2_$4

REM Highest difference peak  0.154,  deepest hole -0.179,  1-sigma level  0.039
Q1    1   0.3020  0.5468  0.5447  11.00000  0.05    0.15
Q2    1   0.0193  0.5491  0.2449  11.00000  0.05    0.15
Q3    1  -0.0283  0.0629  0.2398  11.00000  0.05    0.11
Q4    1   0.1033  0.6570  0.3376  11.00000  0.05    0.11
Q5    1   0.1531  0.1570  0.5061  11.00000  0.05    0.10
Q6    1   0.0940  0.2109  0.5248  11.00000  0.05    0.10
Q7    1   0.2284  1.0176  0.4949  11.00000  0.05    0.10
Q8    1   0.1849  0.5562  0.7371  11.00000  0.05    0.10
Q9    1   0.4060  0.0912  0.6768  11.00000  0.05    0.10
Q10   1   0.0244  1.0031  0.3191  11.00000  0.05    0.10
Q11   1   0.3388  0.9690  0.4663  11.00000  0.05    0.09
Q12   1   0.2325  0.5749  0.4419  11.00000  0.05    0.09
Q13   1   0.2062  0.4351  0.6877  11.00000  0.05    0.09
Q14   1  -0.1253  0.8211  0.2464  11.00000  0.05    0.09
Q15   1   0.4227  0.8327  0.5377  11.00000  0.05    0.08
Q16   1   0.7298  0.0071  1.0237  11.00000  0.05    0.08
Q17   1   0.4595  0.6798  0.3179  11.00000  0.05    0.08
Q18   1   0.0724  0.2322  0.3042  11.00000  0.05    0.08
Q19   1   0.5191  0.2367  0.6753  11.00000  0.05    0.08
Q20   1   0.5978 -0.1105  0.8172  11.00000  0.05    0.08
;
_shelx_res_checksum              48397
_olex2_submission_special_instructions 'No special instructions were received'
