# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_nmala-nca
_database_code_depnum_ccdc_archive 'CCDC 1976455'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Institut of Organic Chemistry
Germany
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H7 N O3'
_chemical_formula_sum            'C5 H7 N O3'
_chemical_formula_weight         129.12

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   6.3429(9)
_cell_length_b                   6.9256(11)
_cell_length_c                   13.530(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.769(12)
_cell_angle_gamma                90
_cell_volume                     585.71(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2177
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      28.39

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9647
_exptl_absorpt_correction_T_max  0.9888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 1 0.1788
0 -1 0 0.1820
1 0 3 0.0982
-1 0 -3 0.0958
1 0 -2 0.0669
-1 0 2 0.0681

_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 154 frames, detector distance = 70 mm
;
_diffrn_reflns_number            9028
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.315
_diffrn_reflns_theta_max         28.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             9028
_reflns_number_gt                5288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
 refined using 3 twin components
 Twin law for transforming hkl(1) to hkl(2):   -0.99788  0.05155  0.00290
                                                0.06380  0.99848  0.00636
                                               -0.01179  0.00554 -1.00126
 Twin law for transforming hkl(1) to hkl(3):    0.99939  0.06235  0.00478
                                               -0.07796  0.99645 -0.01089
                                               -0.02485  0.01638  0.99721
 Twin law for transforming hkl(2) to hkl(3):   -0.99415  0.11381 -0.00693
                                                0.14125  0.99058  0.01758
                                                0.03795  0.01997 -0.99572
 BASF 1=0.423(6)
 BASF 2=0.269(4)
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SHELXT-2014
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 3-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1540P)²+0.2898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9028
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1750
_refine_ls_R_factor_gt           0.1170
_refine_ls_wR_factor_ref         0.3278
_refine_ls_wR_factor_gt          0.2821
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_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_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
C1 C 0.3890(7) 0.0933(7) 0.2817(3) 0.0296(10) Uani 1 1 d . . . . .
O2 O 0.2958(5) 0.0871(5) 0.3684(3) 0.0329(9) Uani 1 1 d . . . . .
C3 C 0.4066(7) 0.2091(7) 0.4381(4) 0.0312(10) Uani 1 1 d . . . . .
C4 C 0.5836(7) 0.3038(7) 0.3948(3) 0.0301(10) Uani 1 1 d . . . . .
H4 H 0.553391 0.444837 0.385062 0.036 Uiso 1 1 calc R U . . .
N5 N 0.5593(6) 0.2085(6) 0.2982(3) 0.0295(9) Uani 1 1 d . . . . .
O6 O 0.3167(6) -0.0001(5) 0.2088(3) 0.0391(10) Uani 1 1 d . . . . .
O7 O 0.3593(6) 0.2260(6) 0.5198(3) 0.0416(10) Uani 1 1 d . . . . .
C8 C 0.8017(8) 0.2753(8) 0.4600(4) 0.0358(11) Uani 1 1 d . . . . .
H8A H 0.830911 0.136878 0.469079 0.054 Uiso 1 1 calc R U . . .
H8B H 0.802272 0.335737 0.525573 0.054 Uiso 1 1 calc R U . . .
H8C H 0.912168 0.334873 0.427483 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6695(8) 0.2705(8) 0.2181(4) 0.0360(11) Uani 1 1 d . . . . .
H9A H 0.636616 0.181288 0.161339 0.054 Uiso 1 1 calc R U . . .
H9B H 0.824172 0.271120 0.242347 0.054 Uiso 1 1 calc R U . . .
H9C H 0.622327 0.400823 0.196519 0.054 Uiso 1 1 calc R U . . .

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
C1 0.033(2) 0.039(2) 0.019(2) 0.0017(17) 0.0076(17) 0.0009(18)
O2 0.0341(17) 0.0470(18) 0.0203(17) 0.0012(13) 0.0118(13) -0.0032(13)
C3 0.034(2) 0.043(2) 0.018(2) 0.0007(18) 0.0086(17) 0.0036(19)
C4 0.033(2) 0.041(2) 0.017(2) -0.0016(17) 0.0073(17) 0.0006(18)
N5 0.0301(18) 0.043(2) 0.0174(19) -0.0018(16) 0.0091(14) -0.0030(15)
O6 0.043(2) 0.051(2) 0.0234(19) -0.0064(15) 0.0058(14) -0.0075(15)
O7 0.046(2) 0.061(2) 0.0213(19) -0.0009(15) 0.0166(15) 0.0029(16)
C8 0.036(2) 0.050(3) 0.022(2) -0.0012(19) 0.0040(19) -0.002(2)
C9 0.040(2) 0.053(3) 0.019(2) 0.0004(19) 0.0141(19) -0.004(2)

_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
C1 O6 1.203(6) . ?
C1 N5 1.331(6) . ?
C1 O2 1.400(5) . ?
O2 C3 1.369(6) . ?
C3 O7 1.199(6) . ?
C3 C4 1.503(6) . ?
C4 N5 1.448(6) . ?
C4 C8 1.522(6) . ?
C4 H4 1.0000 . ?
N5 C9 1.450(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
O6 C1 N5 130.1(4) . . ?
O6 C1 O2 120.9(4) . . ?
N5 C1 O2 108.9(4) . . ?
C3 O2 C1 108.5(4) . . ?
O7 C3 O2 121.1(4) . . ?
O7 C3 C4 129.6(4) . . ?
O2 C3 C4 109.3(4) . . ?
N5 C4 C3 100.4(4) . . ?
N5 C4 C8 114.3(4) . . ?
C3 C4 C8 112.5(4) . . ?
N5 C4 H4 109.7 . . ?
C3 C4 H4 109.7 . . ?
C8 C4 H4 109.7 . . ?
C1 N5 C4 112.5(4) . . ?
C1 N5 C9 122.2(4) . . ?
C4 N5 C9 123.2(4) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O6 C1 O2 C3 -178.7(4) . . . . ?
N5 C1 O2 C3 2.9(5) . . . . ?
C1 O2 C3 O7 -178.6(4) . . . . ?
C1 O2 C3 C4 0.5(5) . . . . ?
O7 C3 C4 N5 175.7(5) . . . . ?
O2 C3 C4 N5 -3.3(5) . . . . ?
O7 C3 C4 C8 53.7(7) . . . . ?
O2 C3 C4 C8 -125.3(4) . . . . ?
O6 C1 N5 C4 176.5(5) . . . . ?
O2 C1 N5 C4 -5.3(5) . . . . ?
O6 C1 N5 C9 12.3(8) . . . . ?
O2 C1 N5 C9 -169.5(4) . . . . ?
C3 C4 N5 C1 5.2(5) . . . . ?
C8 C4 N5 C1 125.9(4) . . . . ?
C3 C4 N5 C9 169.2(4) . . . . ?
C8 C4 N5 C9 -70.1(6) . . . . ?

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.106

_shelx_res_file                  
;
TITL nmala in P21/n Trilling
    nmala.res
    created by SHELXL-2018/3 at 10:10:42 on 31-May-2019
CELL   0.71073      6.3429   6.9256  13.5295  90.000  99.769  90.000
ZERR         4      0.0009   0.0011   0.0023   0.000   0.012   0.000
REM Gitterkonstanten aus 2177 Reflexen mit 3.3-28.4 Grad V=585.71(16)
REM farblose Platte
LATT  1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC        C       H       N       O
UNIT 20 28 4 12
L.S.      4
FMAP      -2
PLAN     -5 .5 -.5
TEMP -153
SIZE 0.13 0.29 0.36
CONF
BOND $H
acta
WGHT    0.154000    0.289800
BASF   0.42279   0.26933
FVAR       1.13878   0.01952
C1    1    0.388963    0.093287    0.281728    11.00000    0.03252    0.03885 =
         0.01859    0.00167    0.00757    0.00092
O2    4    0.295786    0.087126    0.368368    11.00000    0.03406    0.04699 =
         0.02027    0.00121    0.01178   -0.00324
C3    1    0.406576    0.209120    0.438113    11.00000    0.03391    0.04265 =
         0.01843    0.00066    0.00864    0.00360
C4    1    0.583632    0.303765    0.394755    11.00000    0.03318    0.04135 =
         0.01675   -0.00163    0.00728    0.00058
AFIX  13
H4    2    0.553391    0.444837    0.385062    11.00000   -1.20000
AFIX   0
N5    3    0.559303    0.208527    0.298178    11.00000    0.03009    0.04269 =
         0.01741   -0.00181    0.00913   -0.00304
O6    4    0.316669   -0.000072    0.208811    11.00000    0.04291    0.05104 =
         0.02343   -0.00640    0.00581   -0.00751
O7    4    0.359254    0.226005    0.519780    11.00000    0.04585    0.06142 =
         0.02129   -0.00085    0.01656    0.00291
C8    1    0.801660    0.275276    0.460035    11.00000    0.03555    0.05008 =
         0.02158   -0.00115    0.00395   -0.00180
AFIX 137
H8A   2    0.830911    0.136878    0.469079    11.00000   -1.50000
H8B   2    0.802272    0.335737    0.525573    11.00000   -1.50000
H8C   2    0.912168    0.334873    0.427483    11.00000   -1.50000
AFIX   0
C9    1    0.669543    0.270461    0.218103    11.00000    0.03977    0.05266 =
         0.01888    0.00040    0.01414   -0.00375
AFIX 137
H9A   2    0.636616    0.181288    0.161339    11.00000   -1.50000
H9B   2    0.824172    0.271120    0.242347    11.00000   -1.50000
H9C   2    0.622327    0.400823    0.196519    11.00000   -1.50000
AFIX   0
HKLF     5




REM  nmala in P21/n Trilling
REM wR2 = 0.3278, GooF = S = 1.145, Restrained GooF = 1.145 for all data
REM R1 = 0.1170 for 5288 Fo > 4sig(Fo) and 0.1750 for all 9028 data
REM 87 parameters refined using 0 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.520,  deepest hole -0.453,  1-sigma level  0.106
Q1    1   0.2875  0.1208  0.4270  11.00000  0.05   -0.45
Q2    1   0.5606  0.0864  0.2979  11.00000  0.05    0.43
Q3    1   0.3189  0.0710  0.3134  11.00000  0.05   -0.42
Q4    1   0.5353  0.2244  0.4172  11.00000  0.05    0.42
Q5    1   0.7155  0.3293  0.2697  11.00000  0.05   -0.37
;
_shelx_res_checksum              94686
####################################################################### 
# 
# 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_cmlz9-nca
_database_code_depnum_ccdc_archive 'CCDC 1976456'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Institut of Organic Chemistry
Germany
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H11 N O3 S'
_chemical_formula_sum            'C7 H11 N O3 S'
_chemical_formula_weight         189.23

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   7.9782(10)
_cell_length_b                   5.9102(5)
_cell_length_c                   9.3714(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.168(11)
_cell_angle_gamma                90
_cell_volume                     434.95(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5273
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.339
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 211 frames, detector distance = 60 mm
;
_diffrn_reflns_number            3577
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.096
_diffrn_reflns_theta_max         27.983
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2055
_reflns_number_gt                1637
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.987

_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.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0783P)²+1.1204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2055
_refine_ls_number_parameters     111
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.1951
_refine_ls_wR_factor_gt          0.1762
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_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
C1 C 0.3591(9) 0.5055(12) 0.1791(8) 0.0299(15) Uani 1 1 d . . . . .
H1 H 0.434106 0.620523 0.143763 0.036 Uiso 1 1 calc R U . . .
C2 C 0.4730(10) 0.3211(13) 0.2568(9) 0.0333(15) Uani 1 1 d . . . . .
O3 O 0.4537(7) 0.1287(9) 0.1708(6) 0.0361(12) Uani 1 1 d . . . . .
C4 C 0.3304(10) 0.1708(12) 0.0498(8) 0.0326(16) Uani 1 1 d . . . . .
N5 N 0.2717(8) 0.3826(11) 0.0542(7) 0.0308(13) Uani 1 1 d . . . . .
O6 O 0.5715(7) 0.3281(10) 0.3671(6) 0.0387(13) Uani 1 1 d . . . . .
O7 O 0.2908(8) 0.0258(9) -0.0420(6) 0.0427(14) Uani 1 1 d . . . . .
C8 C 0.1559(11) 0.4847(14) -0.0643(9) 0.0377(17) Uani 1 1 d . . . . .
H8A H 0.212787 0.611013 -0.103920 0.057 Uiso 1 1 calc R U . . .
H8B H 0.055037 0.540584 -0.029064 0.057 Uiso 1 1 calc R U . . .
H8C H 0.121503 0.371611 -0.140333 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2486(9) 0.6276(12) 0.2700(8) 0.0310(14) Uani 1 1 d . . . . .
H9A H 0.206705 0.769489 0.219884 0.037 Uiso 1 1 calc R U . . .
H9B H 0.319929 0.669658 0.363730 0.037 Uiso 1 1 calc R U . . .
C10 C 0.0943(10) 0.4908(14) 0.3007(9) 0.0361(17) Uani 1 1 d . . . . .
H10A H 0.016168 0.463642 0.207874 0.043 Uiso 1 1 calc R U . . .
H10B H 0.032224 0.582738 0.362774 0.043 Uiso 1 1 calc R U . . .
S11 S 0.1488(2) 0.2210(3) 0.3887(2) 0.0366(5) Uani 1 1 d . . . . .
C12 C 0.2588(11) 0.3169(14) 0.5633(8) 0.0385(17) Uani 1 1 d . . . . .
H12A H 0.375941 0.358497 0.556171 0.058 Uiso 1 1 calc R U . . .
H12B H 0.260397 0.195239 0.634650 0.058 Uiso 1 1 calc R U . . .
H12C H 0.199805 0.448869 0.593954 0.058 Uiso 1 1 calc R U . . .

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
C1 0.033(4) 0.026(3) 0.030(4) -0.003(3) 0.005(3) 0.000(3)
C2 0.033(4) 0.025(3) 0.041(4) -0.003(3) 0.004(3) -0.001(3)
O3 0.035(3) 0.027(2) 0.045(3) -0.001(2) 0.004(2) 0.006(2)
C4 0.040(4) 0.028(4) 0.029(3) -0.001(3) 0.006(3) -0.003(3)
N5 0.034(3) 0.025(3) 0.030(3) -0.004(2) -0.001(2) 0.000(2)
O6 0.037(3) 0.036(3) 0.040(3) 0.001(2) -0.002(2) 0.003(2)
O7 0.053(3) 0.030(3) 0.045(3) -0.011(3) 0.009(3) -0.004(3)
C8 0.048(4) 0.030(4) 0.032(4) 0.003(3) -0.001(3) -0.001(3)
C9 0.037(3) 0.022(3) 0.032(3) -0.004(3) 0.000(3) 0.000(3)
C10 0.033(4) 0.042(4) 0.034(4) -0.002(3) 0.006(3) 0.002(3)
S11 0.0415(9) 0.0296(8) 0.0384(9) -0.0035(8) 0.0061(7) -0.0045(9)
C12 0.048(4) 0.033(4) 0.035(4) 0.001(3) 0.006(3) 0.004(4)

_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
C1 N5 1.447(9) . ?
C1 C9 1.513(9) . ?
C1 C2 1.520(10) . ?
C1 H1 1.0000 . ?
C2 O6 1.183(9) . ?
C2 O3 1.387(9) . ?
O3 C4 1.386(9) . ?
C4 O7 1.215(8) . ?
C4 N5 1.340(10) . ?
N5 C8 1.445(10) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.542(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 S11 1.813(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
S11 C12 1.806(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
N5 C1 C9 116.7(6) . . ?
N5 C1 C2 100.9(6) . . ?
C9 C1 C2 115.5(6) . . ?
N5 C1 H1 107.7 . . ?
C9 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
O6 C2 O3 121.7(7) . . ?
O6 C2 C1 130.0(7) . . ?
O3 C2 C1 108.3(6) . . ?
C4 O3 C2 108.6(5) . . ?
O7 C4 N5 129.2(7) . . ?
O7 C4 O3 120.7(7) . . ?
N5 C4 O3 110.1(6) . . ?
C4 N5 C8 123.1(7) . . ?
C4 N5 C1 111.9(6) . . ?
C8 N5 C1 124.3(7) . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C9 C10 114.7(6) . . ?
C1 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C1 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 S11 114.3(5) . . ?
C9 C10 H10A 108.7 . . ?
S11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
S11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 S11 C10 100.1(4) . . ?
S11 C12 H12A 109.5 . . ?
S11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N5 C1 C2 O6 -179.2(8) . . . . ?
C9 C1 C2 O6 -52.4(11) . . . . ?
N5 C1 C2 O3 4.6(8) . . . . ?
C9 C1 C2 O3 131.5(7) . . . . ?
O6 C2 O3 C4 -180.0(7) . . . . ?
C1 C2 O3 C4 -3.5(8) . . . . ?
C2 O3 C4 O7 -179.8(7) . . . . ?
C2 O3 C4 N5 0.7(8) . . . . ?
O7 C4 N5 C8 -6.4(13) . . . . ?
O3 C4 N5 C8 173.0(7) . . . . ?
O7 C4 N5 C1 -176.8(8) . . . . ?
O3 C4 N5 C1 2.6(9) . . . . ?
C9 C1 N5 C4 -130.4(7) . . . . ?
C2 C1 N5 C4 -4.4(8) . . . . ?
C9 C1 N5 C8 59.3(10) . . . . ?
C2 C1 N5 C8 -174.6(7) . . . . ?
N5 C1 C9 C10 43.7(9) . . . . ?
C2 C1 C9 C10 -74.7(8) . . . . ?
C1 C9 C10 S11 56.9(8) . . . . ?
C9 C10 S11 C12 67.5(6) . . . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.094

_shelx_res_file                  
;
TITL cmlz9 in P 21
    cmlz9.res
    created by SHELXL-2018/3 at 08:42:40 on 30-Oct-2018
CELL   0.71073      7.9782   5.9102   9.3714  90.000 100.168  90.000
ZERR         2      0.0010   0.0005   0.0013   0.000   0.011   0.000
REM Gitterkonstanten aus 5273 Reflexen mit 3.1-28.2 Grad V=434.95(9)
REM farbloser Block
LATT -1
SYMM -X,0.5+Y,-Z
SFAC        C       H       N       O       S
UNIT 14 22 2 6 2
OMIT 1 0 5
OMIT 0 0 2
L.S.      4
FMAP      -2
PLAN    -15 .5 -.5
TEMP -153
ACTA
CONF
BOND $H
SIZE 0.070  0.110  0.18
WGHT    0.078300    1.120400
FVAR       1.08303
C1    1    0.359128    0.505464    0.179116    11.00000    0.03340    0.02644 =
         0.02960   -0.00250    0.00469    0.00006
AFIX  13
H1    2    0.434106    0.620523    0.143763    11.00000   -1.20000
AFIX   0
C2    1    0.473050    0.321148    0.256825    11.00000    0.03268    0.02502 =
         0.04109   -0.00272    0.00388   -0.00106
O3    4    0.453695    0.128731    0.170779    11.00000    0.03522    0.02697 =
         0.04500   -0.00080    0.00433    0.00594
C4    1    0.330389    0.170788    0.049770    11.00000    0.03978    0.02838 =
         0.02937   -0.00056    0.00566   -0.00338
N5    3    0.271737    0.382624    0.054213    11.00000    0.03423    0.02534 =
         0.03020   -0.00431   -0.00112    0.00044
O6    4    0.571502    0.328146    0.367074    11.00000    0.03717    0.03580 =
         0.03999    0.00148   -0.00173    0.00271
O7    4    0.290792    0.025845   -0.041992    11.00000    0.05282    0.03013 =
         0.04538   -0.01134    0.00926   -0.00414
C8    1    0.155948    0.484670   -0.064314    11.00000    0.04751    0.03041 =
         0.03216    0.00325   -0.00133   -0.00121
AFIX 137
H8A   2    0.212787    0.611013   -0.103920    11.00000   -1.50000
H8B   2    0.055037    0.540584   -0.029064    11.00000   -1.50000
H8C   2    0.121503    0.371611   -0.140333    11.00000   -1.50000
AFIX   0
C9    1    0.248638    0.627630    0.270018    11.00000    0.03743    0.02165 =
         0.03166   -0.00362   -0.00032    0.00036
AFIX  23
H9A   2    0.206705    0.769489    0.219884    11.00000   -1.20000
H9B   2    0.319929    0.669658    0.363730    11.00000   -1.20000
AFIX   0
C10   1    0.094294    0.490803    0.300737    11.00000    0.03280    0.04160 =
         0.03403   -0.00168    0.00597    0.00193
AFIX  23
H10A  2    0.016168    0.463642    0.207874    11.00000   -1.20000
H10B  2    0.032224    0.582738    0.362774    11.00000   -1.20000
AFIX   0
S11   5    0.148821    0.220959    0.388725    11.00000    0.04154    0.02957 =
         0.03843   -0.00345    0.00605   -0.00452
C12   1    0.258820    0.316857    0.563343    11.00000    0.04773    0.03293 =
         0.03450    0.00056    0.00631    0.00376
AFIX 137
H12A  2    0.375941    0.358497    0.556171    11.00000   -1.50000
H12B  2    0.260397    0.195239    0.634650    11.00000   -1.50000
H12C  2    0.199805    0.448869    0.593954    11.00000   -1.50000
AFIX   0
HKLF      4




REM  cmlz9 in P 21
REM wR2 = 0.1951, GooF = S = 1.058, Restrained GooF = 1.058 for all data
REM R1 = 0.0756 for 1637 Fo > 4sig(Fo) and 0.0991 for all 2055 data
REM 111 parameters refined using 1 restraints

END

WGHT      0.0765      1.1758

REM Highest difference peak  0.400,  deepest hole -0.577,  1-sigma level  0.094
Q1    1   0.2061  0.1307  0.3425  11.00000  0.05   -0.58
Q2    1   0.0993  0.1316  0.4378  11.00000  0.05   -0.55
Q3    1   0.1969  0.3156  0.3433  11.00000  0.05   -0.54
Q4    1   0.1058  0.3106  0.4323  11.00000  0.05   -0.46
Q5    1   0.0410  0.2231  0.3613  11.00000  0.05   -0.44
Q6    1   0.2765  0.6904 -0.0163  11.00000  0.05    0.40
Q7    1   0.3744  0.3455  0.1673  11.00000  0.05    0.38
Q8    1  -0.0220  0.3001  0.3887  11.00000  0.05    0.37
Q9    1   0.3547  0.2574 -0.0003  11.00000  0.05   -0.37
Q10   1   0.7047  0.1843  0.4180  11.00000  0.05    0.36
Q11   1   0.3957  0.2751  0.3625  11.00000  0.05    0.35
Q12   1   0.3828  0.2457  0.2125  11.00000  0.05   -0.34
Q13   1   0.0609  0.2376  0.2847  11.00000  0.05    0.34
Q14   1   0.2255  0.1453  0.0035  11.00000  0.05   -0.33
Q15   1   0.5076  0.2394  0.1384  11.00000  0.05   -0.33
;
_shelx_res_checksum              88319
