# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2085324'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;The University of Melbourne
Australia
;
_audit_update_record             
;
2021-05-23 deposited with the CCDC.	2022-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 Ca N2 O9'
_chemical_formula_weight         374.36
_chemical_oxdiff_usercomment     'kamran B-19-C'

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'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.9257(4)
_cell_length_b                   12.3615(3)
_cell_length_c                   7.6799(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.951(2)
_cell_angle_gamma                90
_cell_volume                     1605.91(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    8593
_cell_measurement_theta_min      2.4580
_cell_measurement_theta_max      37.0890

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.343
_exptl_absorpt_coefficient_mu    0.441
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.49729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.29a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.660
_oxdiff_exptl_absorpt_empirical_full_max 1.894
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12047
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.408
_diffrn_reflns_theta_max         37.199
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3740
_reflns_number_gt                3395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0528P)²+0.7860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     130
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_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 0.64274(4) 0.24026(6) 0.62457(9) 0.00934(12) Uani 1 1 d . . . . .
C2 C 0.70552(5) 0.26550(6) 0.73961(10) 0.01224(13) Uani 1 1 d . . . . .
H2 H 0.717737 0.217568 0.829910 0.015 Uiso 1 1 calc R U . . .
C3 C 0.73004(5) 0.42497(7) 0.59761(12) 0.01499(14) Uani 1 1 d . . . . .
H3 H 0.759488 0.488099 0.588302 0.018 Uiso 1 1 calc R U . . .
C4 C 0.66828(5) 0.40699(6) 0.47742(11) 0.01499(14) Uani 1 1 d . . . . .
H4 H 0.656525 0.457190 0.390139 0.018 Uiso 1 1 calc R U . . .
C5 C 0.62438(5) 0.31245(6) 0.49016(10) 0.01262(13) Uani 1 1 d . . . . .
H5 H 0.583348 0.297673 0.410065 0.015 Uiso 1 1 calc R U . . .
C6 C 0.59800(4) 0.13651(6) 0.64500(9) 0.00874(11) Uani 1 1 d . . . . .
N1 N 0.74921(4) 0.35557(6) 0.72648(10) 0.01452(12) Uani 1 1 d . . . . .
O1 O 0.55425(3) 0.10266(5) 0.52070(7) 0.01220(11) Uani 1 1 d . . . . .
O2 O 0.60513(4) 0.08644(5) 0.78823(7) 0.01242(11) Uani 1 1 d . . . . .
O3 O 0.60104(3) 0.15420(5) 0.12329(7) 0.01177(11) Uani 1 1 d D . . . .
O4 O 0.57610(6) 0.37722(7) 0.03790(15) 0.0340(2) Uani 1 1 d D . . . .
O5 O 0.500000 0.52622(10) 0.250000 0.0329(3) Uani 1 2 d DS T P . .
Ca1 Ca 0.500000 0.04578(2) 0.250000 0.00755(6) Uani 1 2 d S T P . .
H3A H 0.6050(11) 0.1344(14) 0.0214(14) 0.041(5) Uiso 1 1 d D . . . .
H3B H 0.6458(7) 0.1482(13) 0.170(2) 0.036(4) Uiso 1 1 d D . . . .
H4A H 0.5818(10) 0.3144(8) 0.063(2) 0.033(4) Uiso 1 1 d D . . . .
H4B H 0.556(2) 0.418(3) 0.106(5) 0.146(15) Uiso 1 1 d D . . . .
H5A H 0.5086(16) 0.5589(15) 0.3372(10) 0.20(2) Uiso 1 1 d D . . . .


_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 C5 1.3917(11) . ?
C1 C2 1.3940(10) . ?
C1 C6 1.5002(10) . ?
C2 N1 1.3423(10) . ?
C2 H2 0.9300 . ?
C3 N1 1.3413(12) . ?
C3 C4 1.3887(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.3901(11) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 O1 1.2596(8) . ?
C6 O2 1.2644(9) . ?
C6 Ca1 2.9275(7) 5_656 ?
O1 Ca1 2.3515(5) . ?
O1 Ca1 2.7242(6) 5_656 ?
O2 Ca1 2.4266(6) 5_656 ?
O3 Ca1 2.4043(6) . ?
O3 H3A 0.825(9) . ?
O3 H3B 0.832(9) . ?
O4 H4A 0.805(9) . ?
O4 H4B 0.809(10) . ?
O5 H5A 0.791(9) . ?
O5 H5A 0.791(9) 2_655 ?
Ca1 Ca1 4.00328(14) 5_655 ?
Ca1 Ca1 4.00328(14) 5_656 ?
Ca1 H3A 2.766(16) . ?

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
C5 C1 C2 118.21(7) . . ?
C5 C1 C6 121.67(6) . . ?
C2 C1 C6 120.11(6) . . ?
N1 C2 C1 123.23(7) . . ?
N1 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
N1 C3 C4 123.08(7) . . ?
N1 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C3 C4 C5 118.68(7) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C1 119.01(7) . . ?
C4 C5 H5 120.5 . . ?
C1 C5 H5 120.5 . . ?
O1 C6 O2 122.21(7) . . ?
O1 C6 C1 119.38(6) . . ?
O2 C6 C1 118.41(6) . . ?
O1 C6 Ca1 68.23(4) . 5_656 ?
O2 C6 Ca1 54.67(4) . 5_656 ?
C1 C6 Ca1 168.38(5) . 5_656 ?
C3 N1 C2 117.77(7) . . ?
C6 O1 Ca1 166.20(5) . . ?
C6 O1 Ca1 86.35(4) . 5_656 ?
Ca1 O1 Ca1 103.89(2) . 5_656 ?
C6 O2 Ca1 100.17(4) . 5_656 ?
Ca1 O3 H3A 107.5(13) . . ?
Ca1 O3 H3B 115.1(12) . . ?
H3A O3 H3B 106.5(18) . . ?
H4A O4 H4B 120(3) . . ?
H5A O5 H5A 119(2) . 2_655 ?
O1 Ca1 O1 145.20(3) 2_655 . ?
O1 Ca1 O3 85.96(2) 2_655 2_655 ?
O1 Ca1 O3 74.76(2) . 2_655 ?
O1 Ca1 O3 74.76(2) 2_655 . ?
O1 Ca1 O3 85.96(2) . . ?
O3 Ca1 O3 112.25(3) 2_655 . ?
O1 Ca1 O2 80.32(2) 2_655 5_656 ?
O1 Ca1 O2 124.82(2) . 5_656 ?
O3 Ca1 O2 84.01(2) 2_655 5_656 ?
O3 Ca1 O2 148.781(19) . 5_656 ?
O1 Ca1 O2 124.82(2) 2_655 6 ?
O1 Ca1 O2 80.32(2) . 6 ?
O3 Ca1 O2 148.78(2) 2_655 6 ?
O3 Ca1 O2 84.01(2) . 6 ?
O2 Ca1 O2 95.31(3) 5_656 6 ?
O1 Ca1 O1 76.11(2) 2_655 6 ?
O1 Ca1 O1 130.00(2) . 6 ?
O3 Ca1 O1 153.781(18) 2_655 6 ?
O3 Ca1 O1 81.593(19) . 6 ?
O2 Ca1 O1 74.33(2) 5_656 6 ?
O2 Ca1 O1 50.403(18) 6 6 ?
O1 Ca1 O1 130.00(2) 2_655 5_656 ?
O1 Ca1 O1 76.11(2) . 5_656 ?
O3 Ca1 O1 81.593(19) 2_655 5_656 ?
O3 Ca1 O1 153.781(18) . 5_656 ?
O2 Ca1 O1 50.403(18) 5_656 5_656 ?
O2 Ca1 O1 74.33(2) 6 5_656 ?
O1 Ca1 O1 95.31(3) 6 5_656 ?
O1 Ca1 C6 105.42(2) 2_655 5_656 ?
O1 Ca1 C6 101.21(2) . 5_656 ?
O3 Ca1 C6 84.27(2) 2_655 5_656 ?
O3 Ca1 C6 163.34(2) . 5_656 ?
O2 Ca1 C6 25.157(19) 5_656 5_656 ?
O2 Ca1 C6 82.43(2) 6 5_656 ?
O1 Ca1 C6 82.309(19) 6 5_656 ?
O1 Ca1 C6 25.429(17) 5_656 5_656 ?
O1 Ca1 C6 101.22(2) 2_655 6 ?
O1 Ca1 C6 105.42(2) . 6 ?
O3 Ca1 C6 163.33(2) 2_655 6 ?
O3 Ca1 C6 84.27(2) . 6 ?
O2 Ca1 C6 82.43(2) 5_656 6 ?
O2 Ca1 C6 25.157(19) 6 6 ?
O1 Ca1 C6 25.429(17) 6 6 ?
O1 Ca1 C6 82.309(19) 5_656 6 ?
C6 Ca1 C6 79.34(3) 5_656 6 ?
O1 Ca1 Ca1 41.346(15) 2_655 5_655 ?
O1 Ca1 Ca1 156.899(15) . 5_655 ?
O3 Ca1 Ca1 124.684(14) 2_655 5_655 ?
O3 Ca1 Ca1 75.293(14) . 5_655 ?
O2 Ca1 Ca1 73.587(14) 5_656 5_655 ?
O2 Ca1 Ca1 84.358(14) 6 5_655 ?
O1 Ca1 Ca1 34.766(12) 6 5_655 ?
O1 Ca1 Ca1 116.142(14) 5_656 5_655 ?
C6 Ca1 Ca1 93.732(15) 5_656 5_655 ?
C6 Ca1 Ca1 59.978(14) 6 5_655 ?
O1 Ca1 Ca1 156.899(15) 2_655 5_656 ?
O1 Ca1 Ca1 41.345(15) . 5_656 ?
O3 Ca1 Ca1 75.293(14) 2_655 5_656 ?
O3 Ca1 Ca1 124.684(14) . 5_656 ?
O2 Ca1 Ca1 84.358(14) 5_656 5_656 ?
O2 Ca1 Ca1 73.587(14) 6 5_656 ?
O1 Ca1 Ca1 116.143(14) 6 5_656 ?
O1 Ca1 Ca1 34.766(12) 5_656 5_656 ?
C6 Ca1 Ca1 59.978(14) 5_656 5_656 ?
C6 Ca1 Ca1 93.732(15) 6 5_656 ?
Ca1 Ca1 Ca1 147.154(10) 5_655 5_656 ?
O1 Ca1 H3A 63.9(4) 2_655 . ?
O1 Ca1 H3A 101.7(3) . . ?
O3 Ca1 H3A 121.1(4) 2_655 . ?
O3 Ca1 H3A 16.5(3) . . ?
O2 Ca1 H3A 132.4(3) 5_656 . ?
O2 Ca1 H3A 81.9(4) 6 . ?
O1 Ca1 H3A 67.6(3) 6 . ?
O1 Ca1 H3A 156.2(4) 5_656 . ?
C6 Ca1 H3A 149.5(3) 5_656 . ?
C6 Ca1 H3A 75.4(4) 6 . ?
Ca1 Ca1 H3A 58.8(3) 5_655 . ?
Ca1 Ca1 H3A 137.9(3) 5_656 . ?

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
C5 C1 C2 N1 -0.33(12) . . . . ?
C6 C1 C2 N1 178.39(7) . . . . ?
N1 C3 C4 C5 -0.37(13) . . . . ?
C3 C4 C5 C1 1.25(12) . . . . ?
C2 C1 C5 C4 -0.92(11) . . . . ?
C6 C1 C5 C4 -179.62(7) . . . . ?
C5 C1 C6 O1 14.74(11) . . . . ?
C2 C1 C6 O1 -163.94(7) . . . . ?
C5 C1 C6 O2 -164.61(7) . . . . ?
C2 C1 C6 O2 16.72(10) . . . . ?
C5 C1 C6 Ca1 -113.9(2) . . . 5_656 ?
C2 C1 C6 Ca1 67.5(3) . . . 5_656 ?
C4 C3 N1 C2 -0.85(13) . . . . ?
C1 C2 N1 C3 1.21(12) . . . . ?
O2 C6 O1 Ca1 -129.4(2) . . . . ?
C1 C6 O1 Ca1 51.3(3) . . . . ?
Ca1 C6 O1 Ca1 -138.5(2) 5_656 . . . ?
O2 C6 O1 Ca1 9.07(7) . . . 5_656 ?
C1 C6 O1 Ca1 -170.24(6) . . . 5_656 ?
O1 C6 O2 Ca1 -10.34(8) . . . 5_656 ?
C1 C6 O2 Ca1 168.98(5) . . . 5_656 ?

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
O3 H3A O2 0.825(9) 1.886(9) 2.7092(8) 175.3(19) 1_554
O3 H3B N1 0.832(9) 1.921(9) 2.7516(9) 176.0(16) 7_656
O4 H4A O3 0.805(9) 2.057(9) 2.8618(10) 177.8(18) .
O4 H4B O5 0.809(10) 1.997(11) 2.8013(13) 173(5) .
O5 H5A O4 0.791(9) 2.046(9) 2.7890(12) 156(3) 6_566
O3 H3A O2 0.825(9) 1.886(9) 2.7092(8) 175.3(19) 1_554
O3 H3B N1 0.832(9) 1.921(9) 2.7516(9) 176.0(16) 7_656
O4 H4A O3 0.805(9) 2.057(9) 2.8618(10) 177.8(18) .
O4 H4B O5 0.809(10) 1.997(11) 2.8013(13) 173(5) .
O5 H5A O4 0.791(9) 2.046(9) 2.7890(12) 156(3) 6_566

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2085325'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;The University of Melbourne
Australia
;
_audit_update_record             
;
2021-05-23 deposited with the CCDC.	2022-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Ca N2 O4'
_chemical_formula_weight         284.28
_chemical_oxdiff_usercomment     'kamran B-9 and B17-c'

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'
Ca Ca 0.2262 0.3064 '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                   8.9810(18)
_cell_length_b                   16.792(3)
_cell_length_c                   8.9860(18)
_cell_angle_alpha                90
_cell_angle_beta                 119.47(3)
_cell_angle_gamma                90
_cell_volume                     1179.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    3203
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      32.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.543
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.710918
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20353
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.426
_diffrn_reflns_theta_max         32.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.761
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.761
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.761
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             3231
_reflns_number_gt                3049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0738P)²+0.3524P] 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         3231
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_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 1.00206(17) 0.11431(7) 0.56294(18) 0.0215(2) Uani 1 1 d . . . . .
H1 H 1.006197 0.067026 0.511217 0.026 Uiso 1 1 calc R U . . .
C2 C 0.85549(16) 0.13086(7) 0.57143(17) 0.0198(2) Uani 1 1 d . . . . .
C3 C 0.84768(18) 0.20162(7) 0.64688(19) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.749954 0.215175 0.652102 0.029 Uiso 1 1 calc R U . . .
C4 C 0.98873(19) 0.25179(8) 0.7144(2) 0.0280(3) Uani 1 1 d . . . . .
H4 H 0.988180 0.299192 0.767689 0.034 Uiso 1 1 calc R U . . .
C5 C 1.13015(18) 0.22992(8) 0.7010(2) 0.0262(3) Uani 1 1 d . . . . .
H5 H 1.224485 0.263657 0.747027 0.031 Uiso 1 1 calc R U . . .
C6 C 0.70989(16) 0.07201(7) 0.50219(16) 0.0199(2) Uani 1 1 d . . . . .
C7 C 0.22371(18) 0.36375(7) 0.44456(18) 0.0226(2) Uani 1 1 d . . . . .
H7 H 0.202233 0.310118 0.416152 0.027 Uiso 1 1 calc R U . . .
C8 C 0.38043(17) 0.38474(7) 0.58123(18) 0.0210(2) Uani 1 1 d . . . . .
C9 C 0.41282(19) 0.46456(7) 0.62563(19) 0.0270(3) Uani 1 1 d . . . . .
H9 H 0.517315 0.480718 0.716167 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2856(2) 0.51971(8) 0.5318(2) 0.0327(3) Uani 1 1 d . . . . .
H10 H 0.302499 0.573520 0.559630 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1338(2) 0.49338(8) 0.3965(2) 0.0294(3) Uani 1 1 d . . . . .
H11 H 0.049797 0.530869 0.333708 0.035 Uiso 1 1 calc R U . . .
C12 C 0.51353(16) 0.32168(7) 0.67687(17) 0.0200(2) Uani 1 1 d . . . . .
N1 N 1.13829(15) 0.16258(6) 0.62503(16) 0.0228(2) Uani 1 1 d . . . . .
N2 N 0.10076(16) 0.41676(7) 0.35061(16) 0.0246(2) Uani 1 1 d . . . . .
O1 O 0.56858(12) 0.09591(5) 0.48047(13) 0.0228(2) Uani 1 1 d . . . . .
O2 O 0.74057(12) 0.00323(5) 0.46974(14) 0.0233(2) Uani 1 1 d . . . . .
O3 O 0.46766(13) 0.25055(5) 0.63959(14) 0.0239(2) Uani 1 1 d . . . . .
O4 O 0.65980(12) 0.34401(5) 0.78580(13) 0.0236(2) Uani 1 1 d . . . . .
Ca1 Ca 0.36858(3) 0.12421(2) 0.55589(3) 0.01869(10) Uani 1 1 d . . . . .


_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 N1 1.3392(17) . ?
C1 C2 1.3837(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.3868(17) . ?
C2 C6 1.5075(17) . ?
C3 C4 1.3879(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3833(19) . ?
C4 H4 0.9300 . ?
C5 N1 1.3413(16) . ?
C5 H5 0.9300 . ?
C6 O1 1.2514(15) . ?
C6 O2 1.2547(14) . ?
C7 N2 1.3443(17) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.3880(17) . ?
C8 C12 1.5092(18) . ?
C9 C10 1.388(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(2) . ?
C10 H10 0.9300 . ?
C11 N2 1.3390(17) . ?
C11 H11 0.9300 . ?
C12 O4 1.2486(17) . ?
C12 O3 1.2541(14) . ?
N1 Ca1 2.5186(12) 1_655 ?
N2 Ca1 2.5300(16) 4_565 ?
O1 Ca1 2.2604(10) . ?
O2 Ca1 2.3176(10) 3_656 ?
O3 Ca1 2.2802(10) . ?
O4 Ca1 2.2832(14) 4_666 ?

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
N1 C1 C2 123.67(12) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 118.51(12) . . ?
C1 C2 C6 120.08(11) . . ?
C3 C2 C6 121.41(11) . . ?
C2 C3 C4 118.63(12) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 118.70(12) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 123.40(12) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
O1 C6 O2 125.50(12) . . ?
O1 C6 C2 117.48(11) . . ?
O2 C6 C2 117.02(11) . . ?
N2 C7 C8 123.47(12) . . ?
N2 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 118.63(12) . . ?
C7 C8 C12 120.12(11) . . ?
C9 C8 C12 121.24(13) . . ?
C10 C9 C8 118.45(13) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 118.89(12) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N2 C11 C10 123.55(13) . . ?
N2 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
O4 C12 O3 125.17(12) . . ?
O4 C12 C8 117.95(11) . . ?
O3 C12 C8 116.88(12) . . ?
C1 N1 C5 117.06(11) . . ?
C1 N1 Ca1 115.80(8) . 1_655 ?
C5 N1 Ca1 126.74(9) . 1_655 ?
C11 N2 C7 116.99(13) . . ?
C11 N2 Ca1 121.82(10) . 4_565 ?
C7 N2 Ca1 118.46(9) . 4_565 ?
C6 O1 Ca1 156.23(9) . . ?
C6 O2 Ca1 137.95(8) . 3_656 ?
C12 O3 Ca1 176.19(10) . . ?
C12 O4 Ca1 154.23(9) . 4_666 ?
O1 Ca1 O3 93.20(4) . . ?
O1 Ca1 O4 95.08(4) . 4_565 ?
O3 Ca1 O4 96.68(4) . 4_565 ?
O1 Ca1 O2 97.80(3) . 3_656 ?
O3 Ca1 O2 165.73(4) . 3_656 ?
O4 Ca1 O2 91.39(4) 4_565 3_656 ?
O1 Ca1 N1 176.28(4) . 1_455 ?
O3 Ca1 N1 85.13(4) . 1_455 ?
O4 Ca1 N1 81.83(4) 4_565 1_455 ?
O2 Ca1 N1 84.39(4) 3_656 1_455 ?
O1 Ca1 N2 83.65(4) . 4_666 ?
O3 Ca1 N2 85.46(4) . 4_666 ?
O4 Ca1 N2 177.58(3) 4_565 4_666 ?
O2 Ca1 N2 86.75(4) 3_656 4_666 ?
N1 Ca1 N2 99.51(5) 1_455 4_666 ?

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
N1 C1 C2 C3 0.6(2) . . . . ?
N1 C1 C2 C6 -178.40(12) . . . . ?
C1 C2 C3 C4 -1.6(2) . . . . ?
C6 C2 C3 C4 177.39(13) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C3 C4 C5 N1 0.3(2) . . . . ?
C1 C2 C6 O1 -165.67(13) . . . . ?
C3 C2 C6 O1 15.34(19) . . . . ?
C1 C2 C6 O2 13.71(19) . . . . ?
C3 C2 C6 O2 -165.29(13) . . . . ?
N2 C7 C8 C9 0.7(2) . . . . ?
N2 C7 C8 C12 -178.19(12) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C12 C8 C9 C10 179.48(13) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C9 C10 C11 N2 0.6(3) . . . . ?
C7 C8 C12 O4 171.66(12) . . . . ?
C9 C8 C12 O4 -7.18(19) . . . . ?
C7 C8 C12 O3 -8.15(18) . . . . ?
C9 C8 C12 O3 173.01(13) . . . . ?
C2 C1 N1 C5 0.8(2) . . . . ?
C2 C1 N1 Ca1 -172.37(11) . . . 1_655 ?
C4 C5 N1 C1 -1.3(2) . . . . ?
C4 C5 N1 Ca1 171.05(12) . . . 1_655 ?
C10 C11 N2 C7 0.6(2) . . . . ?
C10 C11 N2 Ca1 -160.33(13) . . . 4_565 ?
C8 C7 N2 C11 -1.3(2) . . . . ?
C8 C7 N2 Ca1 160.33(11) . . . 4_565 ?
O2 C6 O1 Ca1 95.2(2) . . . . ?
C2 C6 O1 Ca1 -85.5(2) . . . . ?
O1 C6 O2 Ca1 -24.1(2) . . . 3_656 ?
C2 C6 O2 Ca1 156.57(10) . . . 3_656 ?
O3 C12 O4 Ca1 -86.4(2) . . . 4_666 ?
C8 C12 O4 Ca1 93.8(2) . . . 4_666 ?

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.076



