# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2047539'
loop_
_audit_author_name
_audit_author_address
'Dandan Han'
;Tianjin University
China
;
_audit_update_record             
;
2020-12-01 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_audit_creation_date             2020-12-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H40 Ca N2 O12, 2(C H4 O), H2 O'
_chemical_formula_sum            'C22 H50 Ca N2 O15'
_chemical_formula_weight         622.72
_chemical_absolute_configuration rm
_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'
Ca Ca 0.2262 0.3064 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   12.428(3)
_cell_length_b                   13.933(3)
_cell_length_c                   18.288(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3166.7(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    30411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.484
_cell_measurement_theta_min      3.128
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9615
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'whiteish white'
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.1853
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30411
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.128
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'rigaku r-axis rapid'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4650
_reflns_number_total             7216
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7216
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0777
_refine_ls_restrained_S_all      1.032
_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)+(0.0922P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O4-H4
 0.9 with sigma of 0.02
 H8B-C8
 0.96 with sigma of 0.02
 H8C-C8
 0.96 with sigma of 0.02
 HW1A-O1
 2.2 with sigma of 0.02
3.a Free rotating group:
 OW1(HW1A,HW1B)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C20(H20A,H20B,
 H20C), C19(H19A,H19B,H19C)
3.c Idealised tetrahedral OH refined as rotating group:
 O13(H13), O14(H14A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Ca1 Ca 1.00450(8) 1.00399(7) 1.03541(6) 0.0373(3) Uani 1 1 d . . . . .
N1 N 1.0044(4) 0.6802(3) 1.0390(3) 0.0425(11) Uani 1 1 d . . . . .
H1 H 1.011(5) 0.642(4) 1.007(3) 0.033(15) Uiso 1 1 d . . . . .
C1 C 0.8083(5) 0.6239(5) 1.1210(3) 0.0461(14) Uani 1 1 d . . . . .
C2 C 0.9074(5) 0.6663(5) 1.1563(4) 0.0465(15) Uani 1 1 d . . . . .
H2A H 0.908(4) 0.647(4) 1.207(3) 0.039(15) Uiso 1 1 d . . . . .
H2B H 0.899(6) 0.726(5) 1.166(3) 0.06(2) Uiso 1 1 d . . . . .
C3 C 1.0102(5) 0.6474(5) 1.1138(3) 0.0477(14) Uani 1 1 d . . . . .
H3A H 1.067(5) 0.685(4) 1.139(3) 0.040(15) Uiso 1 1 d . . . . .
H3B H 1.025(6) 0.589(5) 1.114(4) 0.07(2) Uiso 1 1 d . . . . .
C4 C 0.9994(5) 0.7732(4) 1.0219(3) 0.0415(12) Uani 1 1 d . . . . .
C5 C 0.9879(5) 0.8011(4) 0.9414(3) 0.0403(13) Uani 1 1 d . . . . .
H5 H 1.019(5) 0.751(4) 0.912(3) 0.039(15) Uiso 1 1 d . . . . .
C6 C 0.8683(5) 0.8082(4) 0.9167(3) 0.0444(14) Uani 1 1 d . . . . .
C7 C 0.8201(7) 0.7063(5) 0.9129(5) 0.064(2) Uani 1 1 d . . . . .
H7A H 0.822(6) 0.675(5) 0.963(4) 0.07(2) Uiso 1 1 d . . . . .
H7B H 0.870(5) 0.665(4) 0.875(3) 0.050(17) Uiso 1 1 d . . . . .
H7C H 0.745(6) 0.704(5) 0.901(4) 0.07(2) Uiso 1 1 d . . . . .
C8 C 0.8660(8) 0.8520(7) 0.8406(4) 0.065(2) Uani 1 1 d D . . . .
H8A H 0.885(5) 0.908(4) 0.839(3) 0.033(17) Uiso 1 1 d . . . . .
H8B H 0.793(4) 0.849(10) 0.822(7) 0.23(6) Uiso 1 1 d D . . . .
H8C H 0.908(6) 0.811(5) 0.808(4) 0.11(3) Uiso 1 1 d D . . . .
C9 C 0.8001(5) 0.8656(4) 0.9698(4) 0.0439(14) Uani 1 1 d . . . . .
H9A H 0.734(6) 0.866(5) 0.954(3) 0.06(2) Uiso 1 1 d . . . . .
H9B H 0.793(5) 0.837(4) 1.018(3) 0.047(16) Uiso 1 1 d . . . . .
C10 C 1.2159(5) 1.3602(5) 1.1356(3) 0.0495(15) Uani 1 1 d . . . . .
C11 C 1.1205(6) 1.3187(5) 1.1754(4) 0.0509(16) Uani 1 1 d . . . . .
H11A H 1.120(4) 1.338(4) 1.225(3) 0.043(15) Uiso 1 1 d . . . . .
H11B H 1.133(6) 1.251(5) 1.183(3) 0.07(2) Uiso 1 1 d . . . . .
C12 C 1.0145(5) 1.3458(5) 1.1407(3) 0.0497(15) Uani 1 1 d . . . . .
H12A H 0.958(4) 1.309(3) 1.163(2) 0.022(12) Uiso 1 1 d . . . . .
H12B H 1.000(5) 1.409(4) 1.147(3) 0.041(15) Uiso 1 1 d . . . . .
C13 C 1.0138(4) 1.2333(4) 1.0380(3) 0.0413(13) Uani 1 1 d . . . . .
C14 C 1.0168(5) 1.2171(4) 0.9562(3) 0.0417(13) Uani 1 1 d . . . . .
H14 H 0.977(5) 1.273(4) 0.934(3) 0.043(15) Uiso 1 1 d . . . . .
C15 C 1.1333(5) 1.2149(4) 0.9255(3) 0.0467(14) Uani 1 1 d . . . . .
C16 C 1.1798(7) 1.3175(5) 0.9250(5) 0.0633(19) Uani 1 1 d . . . . .
H16A H 1.184(5) 1.348(4) 0.976(4) 0.056(17) Uiso 1 1 d . . . . .
H16B H 1.129(6) 1.342(5) 0.890(4) 0.07(2) Uiso 1 1 d . . . . .
H16C H 1.260(6) 1.320(5) 0.908(4) 0.07(2) Uiso 1 1 d . . . . .
C17 C 1.2072(5) 1.1537(4) 0.9721(4) 0.0465(14) Uani 1 1 d . . . . .
H17A H 1.272(5) 1.152(4) 0.949(3) 0.044(16) Uiso 1 1 d . . . . .
H17B H 1.216(4) 1.181(4) 1.018(3) 0.040(15) Uiso 1 1 d . . . . .
C18 C 1.1276(7) 1.1741(6) 0.8474(3) 0.071(2) Uani 1 1 d . . . . .
H18A H 1.107060 1.107757 0.849321 0.107 Uiso 1 1 calc R U . . .
H18B H 1.196841 1.179756 0.824488 0.107 Uiso 1 1 calc R U . . .
H18C H 1.075382 1.209436 0.819592 0.107 Uiso 1 1 calc R U . . .
C22 C 0.8832(8) 0.3970(7) 0.7913(4) 0.093(3) Uani 1 1 d . . . . .
H22A H 0.838235 0.392681 0.748773 0.139 Uiso 1 1 calc R U . . .
H22B H 0.937133 0.347796 0.789540 0.139 Uiso 1 1 calc R U . . .
H22C H 0.917253 0.458830 0.792646 0.139 Uiso 1 1 calc R U . . .
C21 C 0.1261(7) 0.6065(7) 0.8078(5) 0.095(3) Uani 1 1 d . . . . .
H21A H 0.141445 0.569638 0.764752 0.142 Uiso 1 1 calc R U . . .
H21B H 0.084867 0.662202 0.794694 0.142 Uiso 1 1 calc R U . . .
H21C H 0.085649 0.568048 0.841621 0.142 Uiso 1 1 calc R U . . .
C20 C 1.1372(6) 0.9413(5) 1.2003(3) 0.0595(17) Uani 1 1 d . . . . .
H20A H 1.086219 0.889675 1.197262 0.089 Uiso 1 1 calc R U . . .
H20B H 1.116968 0.983963 1.239111 0.089 Uiso 1 1 calc R U . . .
H20C H 1.207531 0.915717 1.209836 0.089 Uiso 1 1 calc R U . . .
C19 C 0.8736(6) 1.0555(5) 1.2037(3) 0.0605(18) Uani 1 1 d . . . . .
H19A H 0.929225 1.103319 1.203952 0.091 Uiso 1 1 calc R U . . .
H19B H 0.881283 1.014989 1.245881 0.091 Uiso 1 1 calc R U . . .
H19C H 0.804553 1.086245 1.204869 0.091 Uiso 1 1 calc R U . . .
N2 N 1.0111(4) 1.3229(3) 1.0626(3) 0.0447(11) Uani 1 1 d . . . . .
H2 H 0.999(5) 1.367(4) 1.034(3) 0.044(16) Uiso 1 1 d . . . . .
O1 O 0.8164(4) 0.5431(3) 1.0920(3) 0.0612(12) Uani 1 1 d D . . . .
OW1 O 0.9407(4) 0.4858(3) 0.9716(3) 0.0698(13) Uani 1 1 d G . . . .
HW1A H 0.885605 0.515925 0.986762 0.105 Uiso 1 1 d DG U . . .
HW1B H 0.916419 0.447148 0.939675 0.105 Uiso 1 1 d G U . . .
O2 O 0.7236(4) 0.6730(3) 1.1228(3) 0.0650(13) Uani 1 1 d . . . . .
O3 O 1.0045(4) 0.8355(2) 1.06888(19) 0.0487(10) Uani 1 1 d . . . . .
O4 O 1.0413(3) 0.8898(3) 0.9332(2) 0.0462(10) Uani 1 1 d D . . . .
H4 H 1.105(4) 0.886(7) 0.914(5) 0.14(4) Uiso 1 1 d D . . . .
O5 O 0.8359(4) 0.9606(3) 0.9812(3) 0.0473(11) Uani 1 1 d . . . . .
H5A H 0.815(5) 0.987(5) 0.958(3) 0.03(2) Uiso 1 1 d . . . . .
O6 O 1.2968(4) 1.3070(3) 1.1268(3) 0.0680(13) Uani 1 1 d . . . . .
O7 O 1.2093(4) 1.4436(3) 1.1119(3) 0.0674(13) Uani 1 1 d . . . . .
O8 O 1.0124(4) 1.1645(2) 1.08075(19) 0.0476(10) Uani 1 1 d . . . . .
O9 O 0.9638(4) 1.1282(3) 0.9443(3) 0.0514(12) Uani 1 1 d . . . . .
H9 H 0.926(5) 1.135(4) 0.922(3) 0.026(18) Uiso 1 1 d . . . . .
O10 O 1.1718(4) 1.0580(3) 0.9827(3) 0.0487(11) Uani 1 1 d . . . . .
H10 H 1.194(4) 1.029(4) 0.957(2) 0.010(14) Uiso 1 1 d . . . . .
O13 O 0.2208(5) 0.6347(4) 0.8399(4) 0.0920(18) Uani 1 1 d . . . . .
H13 H 0.216146 0.691052 0.852506 0.138 Uiso 1 1 calc R U . . .
O14 O 0.8205(4) 0.3851(4) 0.8539(3) 0.0696(13) Uani 1 1 d . . . . .
H14A H 0.801050 0.329003 0.856861 0.104 Uiso 1 1 calc R U . . .
O11 O 0.8821(4) 1.0002(4) 1.1407(2) 0.0631(13) Uani 1 1 d . . . . .
O12 O 1.1385(4) 0.9909(4) 1.1349(3) 0.0643(14) Uani 1 1 d . . . . .
H12 H 1.181(5) 1.031(5) 1.130(3) 0.05(2) Uiso 1 1 d . . . . .
H11 H 0.835(6) 0.965(6) 1.132(4) 0.07(3) Uiso 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
Ca1 C4 3.226(5) . ?
Ca1 C13 3.197(5) . ?
Ca1 O3 2.426(4) . ?
Ca1 O4 2.497(4) . ?
Ca1 O5 2.395(5) . ?
Ca1 H5A 2.76(6) . ?
Ca1 O8 2.387(4) . ?
Ca1 O9 2.455(5) . ?
Ca1 O10 2.412(5) . ?
Ca1 H10 2.78(5) . ?
Ca1 O11 2.454(4) . ?
Ca1 O12 2.473(5) . ?
N1 H1 0.80(5) . ?
N1 C3 1.445(8) . ?
N1 C4 1.334(7) . ?
C1 C2 1.511(9) . ?
C1 O1 1.249(7) . ?
C1 O2 1.256(7) . ?
C2 H2A 0.96(5) . ?
C2 H2B 0.86(7) . ?
C2 C3 1.518(9) . ?
C3 H3A 0.99(6) . ?
C3 H3B 0.83(7) . ?
C4 C5 1.529(8) . ?
C4 O3 1.224(6) . ?
C5 H5 0.96(6) . ?
C5 C6 1.557(8) . ?
C5 O4 1.411(7) . ?
C6 C7 1.542(9) . ?
C6 C8 1.520(9) . ?
C6 C9 1.518(8) . ?
C7 H7A 1.02(7) . ?
C7 H7B 1.09(6) . ?
C7 H7C 0.96(8) . ?
C8 H8A 0.82(5) . ?
C8 H8B 0.97(3) . ?
C8 H8C 0.97(3) . ?
C9 H9A 0.87(7) . ?
C9 H9B 0.97(6) . ?
C9 O5 1.412(7) . ?
C10 C11 1.507(9) . ?
C10 O6 1.259(8) . ?
C10 O7 1.243(8) . ?
C11 H11A 0.94(5) . ?
C11 H11B 0.96(7) . ?
C11 C12 1.510(10) . ?
C12 H12A 0.96(5) . ?
C12 H12B 0.91(6) . ?
C12 N2 1.465(8) . ?
C13 C14 1.514(8) . ?
C13 N2 1.328(7) . ?
C13 O8 1.237(6) . ?
C14 H14 1.01(6) . ?
C14 C15 1.554(8) . ?
C14 O9 1.419(7) . ?
C15 C16 1.542(10) . ?
C15 C17 1.515(9) . ?
C15 C18 1.540(8) . ?
C16 H16A 1.03(6) . ?
C16 H16B 0.96(8) . ?
C16 H16C 1.04(8) . ?
C17 H17A 0.91(6) . ?
C17 H17B 0.93(6) . ?
C17 O10 1.418(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 O14 1.393(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 O13 1.373(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 O12 1.381(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 O11 1.391(8) . ?
N2 H2 0.83(6) . ?
OW1 HW1A 0.8501 . ?
OW1 HW1B 0.8501 . ?
O4 H4 0.87(3) . ?
O5 H5A 0.63(6) . ?
O9 H9 0.62(5) . ?
O10 H10 0.68(5) . ?
O13 H13 0.8200 . ?
O14 H14A 0.8200 . ?
O11 H11 0.78(8) . ?
O12 H12 0.78(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 Ca1 H5A 82.0(13) . . ?
C4 Ca1 H10 95.9(10) . . ?
C13 Ca1 C4 176.32(15) . . ?
C13 Ca1 H5A 97.0(13) . . ?
C13 Ca1 H10 81.4(10) . . ?
O3 Ca1 C4 19.05(12) . . ?
O3 Ca1 C13 164.40(14) . . ?
O3 Ca1 O4 64.68(13) . . ?
O3 Ca1 H5A 92.8(13) . . ?
O3 Ca1 O9 148.61(14) . . ?
O3 Ca1 H10 104.7(10) . . ?
O3 Ca1 O11 77.38(17) . . ?
O3 Ca1 O12 75.11(16) . . ?
O4 Ca1 C4 46.44(14) . . ?
O4 Ca1 C13 129.88(14) . . ?
O4 Ca1 H5A 73.6(13) . . ?
O4 Ca1 H10 62.5(10) . . ?
O5 Ca1 C4 72.51(16) . . ?
O5 Ca1 C13 106.85(16) . . ?
O5 Ca1 O3 81.97(16) . . ?
O5 Ca1 O4 71.92(15) . . ?
O5 Ca1 H5A 11.4(13) . . ?
O5 Ca1 O9 73.56(18) . . ?
O5 Ca1 O10 131.88(19) . . ?
O5 Ca1 H10 123.9(10) . . ?
O5 Ca1 O11 77.12(17) . . ?
O5 Ca1 O12 151.02(18) . . ?
H5A Ca1 H10 117.7(16) . . ?
O8 Ca1 C4 164.02(13) . . ?
O8 Ca1 C13 19.49(12) . . ?
O8 Ca1 O3 144.97(13) . . ?
O8 Ca1 O4 148.15(13) . . ?
O8 Ca1 O5 114.61(16) . . ?
O8 Ca1 H5A 107.0(13) . . ?
O8 Ca1 O9 65.39(14) . . ?
O8 Ca1 O10 79.10(16) . . ?
O8 Ca1 H10 91.5(10) . . ?
O8 Ca1 O11 76.88(16) . . ?
O8 Ca1 O12 77.61(17) . . ?
O9 Ca1 C4 130.31(15) . . ?
O9 Ca1 C13 46.59(15) . . ?
O9 Ca1 O4 88.81(17) . . ?
O9 Ca1 H5A 62.2(13) . . ?
O9 Ca1 H10 74.5(10) . . ?
O9 Ca1 O12 133.61(18) . . ?
O10 Ca1 C4 107.29(16) . . ?
O10 Ca1 C13 70.31(15) . . ?
O10 Ca1 O3 113.73(15) . . ?
O10 Ca1 O4 75.04(15) . . ?
O10 Ca1 H5A 123.8(13) . . ?
O10 Ca1 O9 71.75(16) . . ?
O10 Ca1 H10 12.7(10) . . ?
O10 Ca1 O11 148.68(18) . . ?
O10 Ca1 O12 74.71(16) . . ?
O11 Ca1 C4 91.53(17) . . ?
O11 Ca1 C13 91.84(17) . . ?
O11 Ca1 O4 133.41(17) . . ?
O11 Ca1 H5A 82.7(13) . . ?
O11 Ca1 O9 114.81(19) . . ?
O11 Ca1 H10 159.0(10) . . ?
O11 Ca1 O12 80.71(19) . . ?
O12 Ca1 C4 89.79(17) . . ?
O12 Ca1 C13 92.20(17) . . ?
O12 Ca1 O4 112.37(16) . . ?
O12 Ca1 H5A 161.3(13) . . ?
O12 Ca1 H10 79.7(10) . . ?
C3 N1 H1 119(4) . . ?
C4 N1 H1 119(4) . . ?
C4 N1 C3 122.1(5) . . ?
O1 C1 C2 117.9(6) . . ?
O1 C1 O2 124.7(6) . . ?
O2 C1 C2 117.4(6) . . ?
C1 C2 H2A 108(3) . . ?
C1 C2 H2B 111(5) . . ?
C1 C2 C3 113.6(5) . . ?
H2A C2 H2B 94(5) . . ?
C3 C2 H2A 116(3) . . ?
C3 C2 H2B 113(5) . . ?
N1 C3 C2 112.8(5) . . ?
N1 C3 H3A 108(3) . . ?
N1 C3 H3B 109(5) . . ?
C2 C3 H3A 105(3) . . ?
C2 C3 H3B 110(5) . . ?
H3A C3 H3B 111(6) . . ?
N1 C4 Ca1 161.6(4) . . ?
N1 C4 C5 118.5(5) . . ?
C5 C4 Ca1 79.7(3) . . ?
O3 C4 Ca1 40.3(2) . . ?
O3 C4 N1 121.5(5) . . ?
O3 C4 C5 120.0(5) . . ?
C4 C5 H5 108(3) . . ?
C4 C5 C6 112.6(5) . . ?
C6 C5 H5 106(3) . . ?
O4 C5 C4 106.3(4) . . ?
O4 C5 H5 113(3) . . ?
O4 C5 C6 111.3(4) . . ?
C7 C6 C5 109.0(5) . . ?
C8 C6 C5 108.0(6) . . ?
C8 C6 C7 108.8(6) . . ?
C9 C6 C5 112.4(5) . . ?
C9 C6 C7 107.3(6) . . ?
C9 C6 C8 111.3(6) . . ?
C6 C7 H7A 110(4) . . ?
C6 C7 H7B 107(3) . . ?
C6 C7 H7C 115(4) . . ?
H7A C7 H7B 109(5) . . ?
H7A C7 H7C 103(6) . . ?
H7B C7 H7C 113(5) . . ?
C6 C8 H8A 114(4) . . ?
C6 C8 H8B 109(8) . . ?
C6 C8 H8C 108(5) . . ?
H8A C8 H8B 108(9) . . ?
H8A C8 H8C 112(7) . . ?
H8B C8 H8C 106(9) . . ?
C6 C9 H9A 108(4) . . ?
C6 C9 H9B 115(3) . . ?
H9A C9 H9B 103(5) . . ?
O5 C9 C6 114.3(5) . . ?
O5 C9 H9A 110(4) . . ?
O5 C9 H9B 106(3) . . ?
O6 C10 C11 117.6(6) . . ?
O7 C10 C11 118.4(6) . . ?
O7 C10 O6 124.0(6) . . ?
C10 C11 H11A 110(3) . . ?
C10 C11 H11B 108(4) . . ?
C10 C11 C12 112.8(5) . . ?
H11A C11 H11B 99(5) . . ?
C12 C11 H11A 109(3) . . ?
C12 C11 H11B 116(4) . . ?
C11 C12 H12A 110(3) . . ?
C11 C12 H12B 111(4) . . ?
H12A C12 H12B 109(5) . . ?
N2 C12 C11 112.4(5) . . ?
N2 C12 H12A 106(3) . . ?
N2 C12 H12B 109(3) . . ?
C14 C13 Ca1 80.7(3) . . ?
N2 C13 Ca1 160.7(4) . . ?
N2 C13 C14 118.4(5) . . ?
O8 C13 Ca1 40.1(2) . . ?
O8 C13 C14 120.7(5) . . ?
O8 C13 N2 121.0(5) . . ?
C13 C14 H14 106(3) . . ?
C13 C14 C15 112.5(5) . . ?
C15 C14 H14 109(3) . . ?
O9 C14 C13 105.6(5) . . ?
O9 C14 H14 113(3) . . ?
O9 C14 C15 111.1(5) . . ?
C16 C15 C14 109.5(5) . . ?
C17 C15 C14 112.0(5) . . ?
C17 C15 C16 107.3(6) . . ?
C17 C15 C18 110.0(5) . . ?
C18 C15 C14 107.4(5) . . ?
C18 C15 C16 110.7(6) . . ?
C15 C16 H16A 113(4) . . ?
C15 C16 H16B 95(5) . . ?
C15 C16 H16C 113(4) . . ?
H16A C16 H16B 119(6) . . ?
H16A C16 H16C 103(5) . . ?
H16B C16 H16C 115(6) . . ?
C15 C17 H17A 107(4) . . ?
C15 C17 H17B 110(3) . . ?
H17A C17 H17B 109(5) . . ?
O10 C17 C15 114.8(5) . . ?
O10 C17 H17A 109(4) . . ?
O10 C17 H17B 108(3) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O14 C22 H22A 109.5 . . ?
O14 C22 H22B 109.5 . . ?
O14 C22 H22C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O13 C21 H21A 109.5 . . ?
O13 C21 H21B 109.5 . . ?
O13 C21 H21C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O12 C20 H20A 109.5 . . ?
O12 C20 H20B 109.5 . . ?
O12 C20 H20C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O11 C19 H19A 109.5 . . ?
O11 C19 H19B 109.5 . . ?
O11 C19 H19C 109.5 . . ?
C12 N2 H2 118(4) . . ?
C13 N2 C12 122.3(5) . . ?
C13 N2 H2 119(4) . . ?
HW1A OW1 HW1B 104.5 . . ?
C4 O3 Ca1 120.6(3) . . ?
Ca1 O4 H4 121(7) . . ?
C5 O4 Ca1 113.1(3) . . ?
C5 O4 H4 115(7) . . ?
Ca1 O5 H5A 120(6) . . ?
C9 O5 Ca1 125.0(4) . . ?
C9 O5 H5A 109(6) . . ?
C13 O8 Ca1 120.5(3) . . ?
Ca1 O9 H9 134(6) . . ?
C14 O9 Ca1 114.6(3) . . ?
C14 O9 H9 108(6) . . ?
Ca1 O10 H10 116(4) . . ?
C17 O10 Ca1 128.0(4) . . ?
C17 O10 H10 109(4) . . ?
C21 O13 H13 109.5 . . ?
C22 O14 H14A 109.5 . . ?
Ca1 O11 H11 108(6) . . ?
C19 O11 Ca1 133.3(5) . . ?
C19 O11 H11 118(6) . . ?
Ca1 O12 H12 108(5) . . ?
C20 O12 Ca1 131.7(5) . . ?
C20 O12 H12 118(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
Ca1 C4 C5 C6 -92.9(4) . . . . ?
Ca1 C4 C5 O4 29.2(3) . . . . ?
Ca1 C13 C14 C15 -94.5(4) . . . . ?
Ca1 C13 C14 O9 26.9(4) . . . . ?
Ca1 C13 N2 C12 13.4(16) . . . . ?
N1 C4 C5 C6 89.3(6) . . . . ?
N1 C4 C5 O4 -148.6(5) . . . . ?
N1 C4 O3 Ca1 176.9(4) . . . . ?
C1 C2 C3 N1 55.6(7) . . . . ?
C3 N1 C4 Ca1 9.8(16) . . . . ?
C3 N1 C4 C5 -177.1(6) . . . . ?
C3 N1 C4 O3 3.4(9) . . . . ?
C4 N1 C3 C2 68.0(7) . . . . ?
C4 C5 C6 C7 -71.3(6) . . . . ?
C4 C5 C6 C8 170.7(5) . . . . ?
C4 C5 C6 C9 47.5(6) . . . . ?
C4 C5 O4 Ca1 -42.4(5) . . . . ?
C5 C4 O3 Ca1 -2.7(7) . . . . ?
C5 C6 C9 O5 58.3(7) . . . . ?
C6 C5 O4 Ca1 80.6(4) . . . . ?
C6 C9 O5 Ca1 -64.0(7) . . . . ?
C7 C6 C9 O5 178.2(6) . . . . ?
C8 C6 C9 O5 -63.0(7) . . . . ?
C10 C11 C12 N2 53.1(7) . . . . ?
C11 C12 N2 C13 65.9(8) . . . . ?
C13 C14 C15 C16 -73.3(6) . . . . ?
C13 C14 C15 C17 45.6(7) . . . . ?
C13 C14 C15 C18 166.4(5) . . . . ?
C13 C14 O9 Ca1 -39.8(5) . . . . ?
C14 C13 N2 C12 -176.3(5) . . . . ?
C14 C13 O8 Ca1 -3.4(7) . . . . ?
C14 C15 C17 O10 55.5(7) . . . . ?
C15 C14 O9 Ca1 82.4(5) . . . . ?
C15 C17 O10 Ca1 -57.8(7) . . . . ?
C16 C15 C17 O10 175.7(6) . . . . ?
C18 C15 C17 O10 -63.8(7) . . . . ?
N2 C13 C14 C15 88.8(6) . . . . ?
N2 C13 C14 O9 -149.8(5) . . . . ?
N2 C13 O8 Ca1 175.5(4) . . . . ?
O1 C1 C2 C3 39.1(8) . . . . ?
O2 C1 C2 C3 -140.6(6) . . . . ?
O3 C4 C5 C6 -91.2(6) . . . . ?
O3 C4 C5 O4 31.0(7) . . . . ?
O4 C5 C6 C7 169.4(5) . . . . ?
O4 C5 C6 C8 51.4(6) . . . . ?
O4 C5 C6 C9 -71.8(6) . . . . ?
O6 C10 C11 C12 -138.3(6) . . . . ?
O7 C10 C11 C12 39.8(8) . . . . ?
O8 C13 C14 C15 -92.2(6) . . . . ?
O8 C13 C14 O9 29.2(7) . . . . ?
O8 C13 N2 C12 4.7(9) . . . . ?
O9 C14 C15 C16 168.5(5) . . . . ?
O9 C14 C15 C17 -72.6(6) . . . . ?
O9 C14 C15 C18 48.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
