# 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_1_350K
_database_code_depnum_ccdc_archive 'CCDC 1820505'
_audit_update_record             
;
2018-01-30 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2018-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(Cl O4), 1(C2 H7 N2)'
_chemical_formula_sum            'C2 H7 Cl N2 O4'
_chemical_formula_weight         158.57
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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      cubic
_space_group_IT_number           221
_space_group_name_H-M_alt        'P m -3 m'
_space_group_name_Hall           '-P 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x, -z, y'
'x, -y, -z'
'x, z, -y'
'z, y, -x'
'-x, y, -z'
'-z, y, x'
'z, x, y'
'y, z, x'
'-y, -z, x'
'z, -x, -y'
'-y, z, -x'
'-z, -x, y'
'-z, x, -y'
'y, -z, -x'
'y, x, -z'
'-y, -x, -z'
'-x, z, y'
'-x, -z, -y'
'z, -y, x'
'-z, -y, -x'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, z, -y'
'-x, y, z'
'-x, -z, y'
'-z, -y, x'
'x, -y, z'
'z, -y, -x'
'-z, -x, -y'
'-y, -z, -x'
'y, z, -x'
'-z, x, y'
'y, -z, x'
'z, x, -y'
'z, -x, y'
'-y, z, x'
'-y, -x, z'
'y, x, z'
'x, -z, -y'
'x, z, y'
'-z, y, -x'
'z, y, x'

_cell_length_a                   5.5893(4)
_cell_length_b                   5.5893(4)
_cell_length_c                   5.5893(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     174.61(4)
_cell_formula_units_Z            0.99984
_cell_measurement_reflns_used    308
_cell_measurement_temperature    350
_cell_measurement_theta_max      44.7290
_cell_measurement_theta_min      7.8910
_shelx_estimated_absorpt_T_max   0.461
_shelx_estimated_absorpt_T_min   0.341
_exptl_absorpt_coefficient_mu    4.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             82
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1046
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.228
_diffrn_reflns_theta_min         7.928
_diffrn_ambient_temperature      350
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                35
_reflns_number_total             59
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.082
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     40
_refine_ls_number_reflns         59
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      0.492
_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)+(0.1450P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1304
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-N2
 2.41 with sigma of 0.02
 N2-N1
 2.287 with sigma of 0.002
 C2-N1
 2.41 with sigma of 0.02
 C1-N2_$1
 1.42 with sigma of 0.02
 N2-C1
 1.32 with sigma of 0.02
 C2-C1
 1.48 with sigma of 0.02
 C1-N1_$1
 1.42 with sigma of 0.02
 N1-C1
 1.312 with sigma of 0.002
 O1-O2 \\sim O2-O3 \\sim O3-O4 \\sim O4-O1 \\sim O1-O3 \\sim O2-O4
 with sigma of 0.001
 Cl1-O1 \\sim Cl1-O2 \\sim Cl1-O3 \\sim Cl1-O4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.05 and sigma
for terminal atoms of 0.1
Uanis(O1) = Uanis(O2) = Uanis(O3) = Uanis(O4) = Uanis(Cl1)
Uanis(C1) = Uanis(N2) = Uanis(N1) = Uanis(C2)
4. Others
 Fixed Sof: Cl1(0.02083) O2(0.02083) O3(0.02083) O4(0.02083) O1(0.02083)
 C2(0.02083) H2A(0.02083) H2B(0.02083) H2C(0.02083) N2(0.02083) H2D(0.02083)
 H2E(0.02083) N1(0.02083) H1A(0.02083) H1B(0.02083) C1(0.02083)
5.a Riding coordinates:
 C2(H2A,H2B,H2C), N2(H2D,H2E), N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.475(6) 0.546(5) 0.487(6) 0.228(12) Uani 0.0208 1 d D . P A -1
O2 O 0.214(5) 0.559(6) 0.487(8) 0.228(12) Uani 0.0208 1 d D . P A -1
O3 O 0.564(8) 0.554(7) 0.734(5) 0.228(12) Uani 0.0208 1 d D . P A -1
O4 O 0.576(7) 0.745(5) 0.351(5) 0.228(12) Uani 0.0208 1 d D . P A -1
O1 O 0.551(7) 0.318(5) 0.377(8) 0.228(12) Uani 0.0208 1 d D . P A -1
C2 C 0.22(2) 1.05(2) -0.102(14) 0.20(2) Uani 0.0208 1 d D . P B -1
H2A H 0.203557 1.023422 -0.270838 0.297 Uiso 0.0208 1 d R . P B -1
H2B H 0.368707 0.976772 -0.049018 0.297 Uiso 0.0208 1 d R . P B -1
H2C H 0.226427 1.217592 -0.069698 0.297 Uiso 0.0208 1 d R . P B -1
N2 N -0.136(10) 0.810(16) -0.070(16) 0.20(2) Uani 0.0208 1 d D . P B -1
H2D H -0.230853 0.715794 0.006682 0.238 Uiso 0.0208 1 d R . P B -1
H2E H -0.135083 0.809584 -0.223668 0.238 Uiso 0.0208 1 d R . P B -1
N1 N 0.032(14) 0.956(13) 0.274(6) 0.20(2) Uani 0.0208 1 d D . P B -1
H1A H -0.062878 0.862372 0.350632 0.238 Uiso 0.0208 1 d R . P B -1
H1B H 0.126262 1.050142 0.350301 0.238 Uiso 0.0208 1 d R . P B -1
C1 C 0.019(7) 0.953(7) 0.039(6) 0.20(2) Uani 0.0208 1 d D . P B -1

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
Cl1 0.27(3) 0.18(3) 0.23(3) -0.042(14) 0.016(17) -0.02(2)
O2 0.27(3) 0.18(3) 0.23(3) -0.042(14) 0.016(17) -0.02(2)
O3 0.27(3) 0.18(3) 0.23(3) -0.042(14) 0.016(17) -0.02(2)
O4 0.27(3) 0.18(3) 0.23(3) -0.042(14) 0.016(17) -0.02(2)
O1 0.27(3) 0.18(3) 0.23(3) -0.042(14) 0.016(17) -0.02(2)
C2 0.23(5) 0.18(4) 0.188(17) -0.03(2) -0.04(3) 0.04(3)
N2 0.23(5) 0.18(4) 0.188(17) -0.03(2) -0.04(3) 0.04(3)
N1 0.23(5) 0.18(4) 0.188(17) -0.03(2) -0.04(3) 0.04(3)
C1 0.23(5) 0.18(4) 0.188(17) -0.03(2) -0.04(3) 0.04(3)

_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
Cl1 O2 1.46(3) . ?
Cl1 O3 1.47(3) . ?
Cl1 O4 1.46(3) . ?
Cl1 O1 1.48(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9599 . ?
C2 H2C 0.9601 . ?
C2 C1 1.48(3) . ?
N2 H2D 0.8597 . ?
N2 H2E 0.8602 . ?
N2 C1 1.33(3) . ?
N1 H1A 0.8601 . ?
N1 H1B 0.8600 . ?
N1 C1 1.312(4) . ?

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
O2 Cl1 O3 109.6(14) . . ?
O2 Cl1 O1 109.3(13) . . ?
O3 Cl1 O1 108.7(13) . . ?
O4 Cl1 O2 110.2(13) . . ?
O4 Cl1 O3 109.7(13) . . ?
O4 Cl1 O1 109.4(14) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C2 H2A 112.7 . . ?
C1 C2 H2B 109.6 . . ?
C1 C2 H2C 106.0 . . ?
H2D N2 H2E 120.0 . . ?
C1 N2 H2D 122.9 . . ?
C1 N2 H2E 117.1 . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 117.3 . . ?
C1 N1 H1B 122.7 . . ?
N2 C1 C2 118(2) . . ?
N1 C1 C2 119(3) . . ?
N1 C1 N2 120(2) . . ?

_iucr_refine_instructions_details 
;
TITL 1 in Pm-3m #221
    1.res
    created by SHELXL-2017/1 at 16:29:50 on 29-Jan-2018
REM reset to Pm-3m #221
CELL 1.54178 5.5893 5.5893 5.5893 90 90 90
ZERR 0.99984 0.0004 0.0004 0.0004 0 0 0
LATT 1
SYMM -Y,+X,+Z
SYMM -X,-Y,+Z
SYMM +Y,-X,+Z
SYMM +X,-Z,+Y
SYMM +X,-Y,-Z
SYMM +X,+Z,-Y
SYMM +Z,+Y,-X
SYMM -X,+Y,-Z
SYMM -Z,+Y,+X
SYMM +Z,+X,+Y
SYMM +Y,+Z,+X
SYMM -Y,-Z,+X
SYMM +Z,-X,-Y
SYMM -Y,+Z,-X
SYMM -Z,-X,+Y
SYMM -Z,+X,-Y
SYMM +Y,-Z,-X
SYMM +Y,+X,-Z
SYMM -Y,-X,-Z
SYMM -X,+Z,+Y
SYMM -X,-Z,-Y
SYMM +Z,-Y,+X
SYMM -Z,-Y,-X
SFAC C H Cl N O
UNIT 2 7 1 2 4
EQIV $1 +Z,1-X,1-Y
DFIX 2.41 C2 N2
DFIX 2.287 0.002 N2 N1
DFIX 2.41 C2 N1
DFIX 1.42 C1 N2_$1
DFIX 1.32 N2 C1
DFIX 1.48 C2 C1
DFIX 1.42 C1 N1_$1
DFIX 1.312 0.002 N1 C1
SADI 0.001 O1 O2 O2 O3 O3 O4 O4 O1 O1 O3 O2 O4
SADI Cl1 O1 Cl1 O2 Cl1 O3 Cl1 O4
ISOR 0.05 0.1
EADP O1 O2 O3 O4 Cl1
EADP C1 N2 N1 C2

L.S. 50
PLAN  40
SIZE 0.2 0.26 0.3
TEMP 76.85
BOND
MORE -1
BOND $H
CONF
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>

WGHT    0.145000
FVAR       1.27640
PART -1
CL1   3    0.475241    0.545816    0.486766    10.02083    0.27233    0.18031 =
         0.23062   -0.04184    0.01631   -0.01759
O2    5    0.214083    0.559008    0.487096    10.02083    0.27233    0.18031 =
         0.23062   -0.04184    0.01631   -0.01759
O3    5    0.564319    0.553661    0.734440    10.02083    0.27233    0.18031 =
         0.23062   -0.04184    0.01631   -0.01759
O4    5    0.575642    0.744979    0.350849    10.02083    0.27233    0.18031 =
         0.23062   -0.04184    0.01631   -0.01759
O1    5    0.550883    0.317669    0.376669    10.02083    0.27233    0.18031 =
         0.23062   -0.04184    0.01631   -0.01759

C2    1    0.222157    1.048942   -0.102018    10.02083    0.22935    0.17754 =
         0.18802   -0.02569   -0.04367    0.04081
AFIX   3
H2A   2    0.203557    1.023422   -0.270838    10.02083   -1.50000
H2B   2    0.368707    0.976772   -0.049018    10.02083   -1.50000
H2C   2    0.226427    1.217592   -0.069698    10.02083   -1.50000
AFIX   0
N2    4   -0.135943    0.809634   -0.069768    10.02083    0.22935    0.17754 =
         0.18802   -0.02569   -0.04367    0.04081
AFIX   3
H2D   2   -0.230853    0.715794    0.006682    10.02083   -1.20000
H2E   2   -0.135083    0.809584   -0.223668    10.02083   -1.20000
AFIX   0
N1    4    0.031822    0.956002    0.273531    10.02083    0.22935    0.17754 =
         0.18802   -0.02569   -0.04367    0.04081
AFIX   3
H1A   2   -0.062878    0.862372    0.350632    10.02083   -1.20000
H1B   2    0.126262    1.050142    0.350301    10.02083   -1.20000
AFIX   0
C1    1    0.019144    0.952651    0.039148    10.02083    0.22935    0.17754 =
         0.18802   -0.02569   -0.04367    0.04081
HKLF 4




REM  1 in Pm-3m #221
REM R1 =  0.0583 for      35 Fo > 4sig(Fo)  and  0.0623 for all      59 data
REM     40 parameters refined using     83 restraints

END  
     
WGHT      0.1039      0.0000 

REM Highest difference peak  0.082,  deepest hole -0.151,  1-sigma level  0.049
Q1    1   0.0000  0.5807  0.5000  10.25000  0.05    0.08
Q2    1   0.5000  1.0000  0.0000  10.06250  0.05    0.06

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0583 for 35 Fo > 4sig(Fo) and 0.0623 for all 1046 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.08, deepest hole -0.15
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0623
  REM R1_gt = 0.0583
  REM wR_ref = 0.1304
  REM GOOF = 1.041
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1046
  REM Reflections_gt = 35
  REM Parameters = n/a
  REM Hole = -0.15
  REM Peak = 0.08
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_180K
_database_code_depnum_ccdc_archive 'CCDC 1820506'
_audit_update_record             
;
2018-01-30 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2017-09-22
_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         'Cl O4, C2 H7 N2'
_chemical_formula_sum            'C2 H7 Cl N2 O4'
_chemical_formula_weight         158.55
_chemical_absolute_configuration ?
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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           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                   4.84640(10)
_cell_length_b                   10.8897(3)
_cell_length_c                   6.03420(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.671(2)
_cell_angle_gamma                90
_cell_volume                     317.807(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    180
_cell_measurement_theta_max      77.1150
_cell_measurement_theta_min      4.0390
_shelx_estimated_absorpt_T_max   0.433
_shelx_estimated_absorpt_T_min   0.314
_exptl_absorpt_coefficient_mu    5.026
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             164
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2230
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.958
_diffrn_reflns_theta_min         7.355
_diffrn_ambient_temperature      180
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                1188
_reflns_number_total             1192
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 
;
 Flack x determined using 518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       0.162(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.131
_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)+(0.0614P)²+0.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0834
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a X=CH2 refined with riding coordinates:
 N2(H2D,H2E), N1(H1A,H1B)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.41011(11) 0.60590(6) 0.90592(8) 0.0077(3) Uani 1 1 d . . . . .
C2 C 1.0177(9) 0.3021(4) 0.5814(6) 0.0170(7) Uani 1 1 d . . . . .
H2A H 1.1849 0.3303 0.6589 0.025 Uiso 1 1 calc GR . . . .
H2B H 1.0477 0.2221 0.5205 0.025 Uiso 1 1 calc GR . . . .
H2C H 0.8731 0.2977 0.6827 0.025 Uiso 1 1 calc GR . . . .
O2 O 0.1144(4) 0.5950(3) 0.8961(5) 0.0263(6) Uani 1 1 d . . . . .
C1 C 0.9360(7) 0.3891(4) 0.3986(5) 0.0087(7) Uani 1 1 d . . . . .
N2 N 0.7577(6) 0.4746(3) 0.4327(5) 0.0205(7) Uani 1 1 d . . . . .
H2D H 0.7107 0.5260 0.3289 0.025 Uiso 1 1 calc R . . . .
H2E H 0.6865 0.4800 0.5593 0.025 Uiso 1 1 calc R . . . .
O3 O 0.4924(6) 0.6805(2) 0.7261(5) 0.0229(6) Uani 1 1 d . . . . .
O4 O 0.5303(5) 0.4846(2) 0.8896(4) 0.0159(5) Uani 1 1 d . . . . .
N1 N 1.0503(6) 0.3777(3) 0.2069(4) 0.0176(6) Uani 1 1 d . . . . .
H1A H 1.0069 0.4278 0.1002 0.021 Uiso 1 1 calc R . . . .
H1B H 1.1681 0.3200 0.1887 0.021 Uiso 1 1 calc R . . . .
O1 O 0.5090(7) 0.6601(3) 1.1136(4) 0.0312(7) Uani 1 1 d . . . . .

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
Cl1 0.0063(4) 0.0041(4) 0.0126(4) 0.0026(2) -0.0012(2) 0.0003(2)
C2 0.0226(17) 0.0139(18) 0.0138(15) 0.0046(12) -0.0040(13) 0.0015(16)
O2 0.0060(11) 0.0237(14) 0.0490(15) 0.0186(13) 0.0012(9) 0.0001(11)
C1 0.0104(14) 0.0029(14) 0.0124(15) -0.0015(9) -0.0040(12) -0.0028(10)
N2 0.0291(16) 0.0161(13) 0.0156(13) -0.0033(11) -0.0040(11) 0.0116(13)
O3 0.0213(12) 0.0178(13) 0.0303(13) 0.0174(10) 0.0084(10) -0.0005(10)
O4 0.0201(12) 0.0039(10) 0.0237(12) -0.0013(8) 0.0010(9) 0.0053(9)
N1 0.0237(15) 0.0118(13) 0.0175(12) 0.0057(10) 0.0029(11) 0.0046(12)
O1 0.0478(19) 0.0211(14) 0.0224(14) -0.0137(10) -0.0158(12) 0.0091(15)

_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
Cl1 O2 1.435(2) . ?
Cl1 O3 1.433(2) . ?
Cl1 O4 1.449(2) . ?
Cl1 O1 1.439(2) . ?
C2 C1 1.489(4) . ?
C1 N2 1.296(5) . ?
C1 N1 1.320(4) . ?

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
O2 Cl1 O4 109.06(17) . . ?
O2 Cl1 O1 110.22(18) . . ?
O3 Cl1 O2 109.96(16) . . ?
O3 Cl1 O4 109.42(15) . . ?
O3 Cl1 O1 109.51(19) . . ?
O1 Cl1 O4 108.65(16) . . ?
N2 C1 C2 119.2(3) . . ?
N2 C1 N1 121.9(3) . . ?
N1 C1 C2 118.9(3) . . ?

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
N2 H2D O1 0.86 2.15 2.990(4) 166.5 1_554
N2 H2E O3 0.86 2.61 3.179(4) 125.1 .
N2 H2E O4 0.86 2.18 3.036(4) 175.8 .
N1 H1A O2 0.86 2.28 3.048(4) 149.2 1_654
N1 H1B O3 0.86 2.27 3.094(4) 159.3 2_746

_iucr_refine_instructions_details 
;

    1.res created by SHELXL-2014/7

TITL 1 in P21 #4
REM reset to P21 #4
CELL 1.54178 4.8464 10.8897 6.0342 90 93.671 90
ZERR 2 0.0001 0.0003 0.0001 0 0.002 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H Cl N O
UNIT 4 14 2 4 8
EQIV $1 +X,+Y,-1+Z
EQIV $2 1+X,+Y,-1+Z
EQIV $3 2-X,-0.5+Y,1-Z
 
L.S. 20
PLAN  2
SIZE 0.2 0.26 0.3
TEMP 24.85
HTAB N2 O3
HTAB N2 O4
HTAB N2 O1_$1
HTAB N1 O2_$2
HTAB N1 O3_$3
BOND
LIST 4
fmap 2 53
acta
OMIT -3 150
OMIT 0 2 0
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>
 
WGHT    0.061400    0.105800
EXTI    0.161582
FVAR       2.56716
CL1   3    0.410107    0.605900    0.905921    11.00000    0.00634    0.00412 =
         0.01255    0.00256   -0.00119    0.00032
C2    1    1.017674    0.302104    0.581416    11.00000    0.02264    0.01385 =
         0.01377    0.00462   -0.00398    0.00155
AFIX 137
H2A   2    1.184901    0.330340    0.658929    11.00000   -1.50000
H2B   2    1.047661    0.222124    0.520511    11.00000   -1.50000
H2C   2    0.873123    0.297733    0.682727    11.00000   -1.50000
AFIX   0
 
O2    5    0.114438    0.595010    0.896127    11.00000    0.00596    0.02369 =
         0.04904    0.01862    0.00122    0.00012
C1    1    0.936008    0.389122    0.398560    11.00000    0.01035    0.00285 =
         0.01242   -0.00152   -0.00397   -0.00278
N2    4    0.757733    0.474612    0.432747    11.00000    0.02909    0.01612 =
         0.01562   -0.00328   -0.00398    0.01161
AFIX  93
H2D   2    0.710663    0.525998    0.328890    11.00000   -1.20000
H2E   2    0.686466    0.479974    0.559296    11.00000   -1.20000
AFIX   0
 
O3    5    0.492440    0.680493    0.726058    11.00000    0.02131    0.01783 =
         0.03030    0.01744    0.00837   -0.00054
O4    5    0.530294    0.484640    0.889571    11.00000    0.02008    0.00387 =
         0.02371   -0.00133    0.00100    0.00528
N1    4    1.050270    0.377657    0.206900    11.00000    0.02374    0.01182 =
         0.01745    0.00567    0.00288    0.00456
AFIX  93
H1A   2    1.006931    0.427800    0.100188    11.00000   -1.20000
H1B   2    1.168067    0.320043    0.188720    11.00000   -1.20000
AFIX   0
 
O1    5    0.508963    0.660056    1.113602    11.00000    0.04777    0.02111 =
         0.02241   -0.01368   -0.01581    0.00909
HKLF 4
 
REM  1 in P21 #4
REM R1 =  0.0336 for    1188 Fo > 4sig(Fo)  and  0.0343 for all    1192 data
REM     84 parameters refined using      1 restraints
 
END  
     
WGHT      0.0614      0.1058 

REM Highest difference peak  0.328,  deepest hole -0.625,  1-sigma level  0.119
Q1    1   0.4554  0.4811  0.3991  11.00000  0.05    0.29
Q2    1   0.7846  0.1019  0.4483  11.00000  0.05    0.28

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0336 for 1188 Fo > 4sig(Fo) and 0.0343 for all 2259 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.33, deepest hole -0.63
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0343
  REM R1_gt = 0.0336
  REM wR_ref = 0.0834
  REM GOOF = 1.132
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 2259
  REM Reflections_gt = 1188
  REM Parameters = n/a
  REM Hole = -0.63
  REM Peak = 0.33
  REM Flack = 0.05(2)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
