# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_ROD94
_audit_block_doi                 10.5517/ccdc.csd.cc24fyxg
_database_code_depnum_ccdc_archive 'CCDC 1979626'
loop_
_audit_author_name
_audit_author_address
'Yonghong Xiao'
;Shantou University
China
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-05-28 downloaded from the CCDC.
;
_audit_creation_date             2020-01-22
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ROD-94
_chemical_name_systematic        ?
_chemical_formula_moiety         'Ca C20 H20 N4 O10'
_chemical_formula_sum            'Ca C20 H20 N4 O10'
_chemical_formula_weight         516.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Ca'
_chemical_oxdiff_usercomment     33-513
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'
Ca Ca 0.3641 1.2855 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   12.9400(3)
_cell_length_b                   13.0550(2)
_cell_length_c                   27.6303(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.917(2)
_cell_angle_gamma                90
_cell_volume                     4642.77(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7598
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.8030
_cell_measurement_theta_min      3.2290
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.594
_exptl_absorpt_coefficient_mu    2.902
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12371
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.102
_diffrn_reflns_theta_min         3.216
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -38.00   0.50    0.50    --    0.00 -38.00   0.00  100
  2  ω     40.00  88.00   0.50    0.50    --    0.00  57.00-150.00   96
  3  ω    -16.00  15.00   0.50    0.50    --    0.00  38.00-180.00   62
  4  ω    -32.00  -7.00   0.50    0.50    --    0.00 -38.00   0.00   50
  5  ω    147.00 184.00   0.50    1.25    --   95.80  30.00  30.00   74
  6  ω     43.00 119.00   0.50    1.25    --   95.80 -61.00   0.00  152
  7  ω     72.00 159.00   0.50    1.25    --   95.80  15.00 -30.00  174
  8  ω     79.00 140.00   0.50    1.25    --   95.80  30.00  30.00  122
  9  ω     28.00 109.00   0.50    1.25    --   95.80 -30.00-150.00  162
 10  ω     29.00  97.00   0.50    1.25    --   95.80 -30.00  30.00  136
 11  ω     82.00 108.00   0.50    1.25    --   95.80 -45.00  30.00   52
 12  ω     28.00 103.00   0.50    1.25    --   95.80 -45.00   0.00  150
 13  ω     11.00  55.00   0.50    1.25    --   95.80 -15.00   0.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1042726000
_diffrn_orient_matrix_UB_12      -0.0161631000
_diffrn_orient_matrix_UB_13      -0.0212163000
_diffrn_orient_matrix_UB_21      -0.0407088000
_diffrn_orient_matrix_UB_22      0.0617936000
_diffrn_orient_matrix_UB_23      -0.0455319000
_diffrn_orient_matrix_UB_31      0.0423085000
_diffrn_orient_matrix_UB_32      0.0992636000
_diffrn_orient_matrix_UB_33      0.0248733000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4280
_reflns_number_total             4570
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.00020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4570
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+38.0696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N5-C22
 1.45 with sigma of 0.02
 N5-C23
 1.45 with sigma of 0.02
 N5-C21
 1.45 with sigma of 0.02
3. Rigid bond restraints
 N5, C21, C22, C23
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N4, C18, C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N5 \\sim C21 \\sim C22 \\sim C23: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
N4 \\sim C18 \\sim C19 \\sim C20: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
5. Others
 Fixed Sof: N4(0.8) N5(0.2) C18(0.8) H18(0.8) C19(0.8) H19A(0.8) H19B(0.8)
 H19C(0.8) C20(0.8) H20A(0.8) H20B(0.8) H20C(0.8) C21(0.2) H21(0.2) C22(0.2)
 H22A(0.2) H22B(0.2) H22C(0.2) C23(0.2) H23A(0.2) H23B(0.2) H23C(0.2)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C12(H12), C15(H15), C21(H21)
6.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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 0.41911(6) 0.65997(6) 0.50668(2) 0.0238(2) Uani 1 1 d . . . . .
O1 O 0.8843(2) 0.7152(2) 0.94563(10) 0.0347(7) Uani 1 1 d . . . . .
O2 O 0.7390(2) 0.6401(2) 0.96420(9) 0.0299(6) Uani 1 1 d . . . . .
O3 O 0.8940(3) 0.7870(3) 0.76646(14) 0.0553(9) Uani 1 1 d . . . . .
O4 O 0.8911(3) 0.6420(3) 0.72745(11) 0.0522(9) Uani 1 1 d . . . . .
O5 O 0.8168(3) 0.4045(3) 0.77307(11) 0.0562(10) Uani 1 1 d . . . . .
O6 O 0.8460(2) 0.3460(2) 0.70334(11) 0.0404(7) Uani 1 1 d . . . . .
O7 O 0.5048(2) 0.5534(2) 0.56284(9) 0.0319(6) Uani 1 1 d . . . . .
O8 O 0.6397(2) 0.4489(2) 0.55656(9) 0.0330(6) Uani 1 1 d . . . . .
O9 O 0.4502(2) 0.7907(2) 0.56599(10) 0.0337(7) Uani 1 1 d . . . . .
O10 O 0.5841(2) 0.6727(2) 0.47767(12) 0.0384(7) Uani 1 1 d . . . . .
N1 N 0.8691(3) 0.6958(3) 0.76160(13) 0.0407(9) Uani 1 1 d . . . . .
N2 N 0.8023(3) 0.4055(3) 0.72877(11) 0.0327(8) Uani 1 1 d . . . . .
N3 N 0.4403(3) 0.9504(3) 0.59741(13) 0.0358(8) Uani 1 1 d . . . . .
N4 N 0.6920(4) 0.6756(4) 0.41900(18) 0.0374(10) Uani 0.8 1 d . U P A 1
N5 N 0.7507(18) 0.642(2) 0.4487(11) 0.041(6) Uani 0.2 1 d D U P B 2
C1 C 0.8012(3) 0.6682(3) 0.93467(13) 0.0258(8) Uani 1 1 d . . . . .
C2 C 0.7740(3) 0.6406(3) 0.88167(13) 0.0258(8) Uani 1 1 d . . . . .
C3 C 0.8327(3) 0.6786(3) 0.84642(14) 0.0287(8) Uani 1 1 d . . . . .
H3 H 0.888070 0.722738 0.854944 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6896(3) 0.5783(3) 0.86726(14) 0.0310(9) Uani 1 1 d . . . . .
H4 H 0.648648 0.553589 0.890460 0.037 Uiso 1 1 calc R U . . .
C5 C 0.8077(3) 0.6499(3) 0.79816(14) 0.0290(8) Uani 1 1 d . . . . .
C6 C 0.6651(3) 0.5520(3) 0.81844(14) 0.0332(9) Uani 1 1 d . . . . .
H6 H 0.607298 0.511295 0.809495 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7259(3) 0.5860(3) 0.78300(13) 0.0272(8) Uani 1 1 d . . . . .
C8 C 0.6932(3) 0.5628(3) 0.73056(13) 0.0270(8) Uani 1 1 d . . . . .
C9 C 0.7278(3) 0.4790(3) 0.70489(13) 0.0278(8) Uani 1 1 d . . . . .
C10 C 0.6226(3) 0.6288(3) 0.70544(13) 0.0277(8) Uani 1 1 d . . . . .
H10 H 0.598727 0.685510 0.721341 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5871(3) 0.6116(3) 0.65706(13) 0.0264(8) Uani 1 1 d . . . . .
H11 H 0.538295 0.655562 0.641142 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6961(3) 0.4627(3) 0.65647(13) 0.0270(8) Uani 1 1 d . . . . .
H12 H 0.722551 0.407914 0.640102 0.032 Uiso 1 1 calc R U . . .
C13 C 0.6241(3) 0.5288(3) 0.63219(12) 0.0240(7) Uani 1 1 d . . . . .
C14 C 0.5868(3) 0.5094(3) 0.57937(13) 0.0259(8) Uani 1 1 d . . . . .
C15 C 0.4124(3) 0.8777(3) 0.56537(16) 0.0354(9) Uani 1 1 d . . . . .
H15 H 0.360462 0.893072 0.540606 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5188(4) 0.9323(4) 0.63805(16) 0.0419(11) Uani 1 1 d . . . . .
H16A H 0.531530 0.860036 0.641390 0.063 Uiso 1 1 calc R U . . .
H16B H 0.494818 0.958289 0.667394 0.063 Uiso 1 1 calc R U . . .
H16C H 0.582026 0.966499 0.632187 0.063 Uiso 1 1 calc R U . . .
C17 C 0.3984(4) 1.0535(4) 0.5920(2) 0.0522(13) Uani 1 1 d . . . . .
H17A H 0.451315 1.099147 0.582902 0.078 Uiso 1 1 calc R U . . .
H17B H 0.375531 1.075582 0.622242 0.078 Uiso 1 1 calc R U . . .
H17C H 0.340729 1.053888 0.567165 0.078 Uiso 1 1 calc R U . . .
C18 C 0.6000(4) 0.6836(4) 0.4361(2) 0.0298(10) Uani 0.8 1 d . U P A 1
H18 H 0.553(5) 0.701(4) 0.414(2) 0.029(15) Uiso 0.8 1 d . . P C 1
C19 C 0.7844(7) 0.6467(11) 0.4527(5) 0.065(3) Uani 0.8 1 d . U P A 1
H19A H 0.834876 0.700765 0.453795 0.098 Uiso 0.8 1 calc R U P A 1
H19B H 0.814182 0.584891 0.441449 0.098 Uiso 0.8 1 calc R U P A 1
H19C H 0.763807 0.635806 0.484731 0.098 Uiso 0.8 1 calc R U P A 1
C20 C 0.7047(6) 0.6971(5) 0.3680(3) 0.0534(17) Uani 0.8 1 d . U P A 1
H20A H 0.637651 0.704837 0.350026 0.080 Uiso 0.8 1 calc R U P A 1
H20B H 0.741022 0.641336 0.354646 0.080 Uiso 0.8 1 calc R U P A 1
H20C H 0.743857 0.759071 0.365869 0.080 Uiso 0.8 1 calc R U P A 1
C21 C 0.6635(17) 0.633(2) 0.4766(9) 0.048(5) Uani 0.2 1 d D U P B 2
H21 H 0.673828 0.582106 0.500030 0.058 Uiso 0.2 1 calc R U P B 2
C22 C 0.842(2) 0.582(2) 0.4637(12) 0.064(8) Uani 0.2 1 d D U P B 2
H22A H 0.831111 0.542897 0.492081 0.097 Uiso 0.2 1 calc R U P B 2
H22B H 0.900647 0.626992 0.471125 0.097 Uiso 0.2 1 calc R U P B 2
H22C H 0.856264 0.536626 0.437860 0.097 Uiso 0.2 1 calc R U P B 2
C23 C 0.762(2) 0.7230(19) 0.4148(13) 0.070(9) Uani 0.2 1 d D U P B 2
H23A H 0.696160 0.755334 0.406448 0.105 Uiso 0.2 1 calc R U P B 2
H23B H 0.787237 0.695355 0.386026 0.105 Uiso 0.2 1 calc R U P B 2
H23C H 0.810879 0.772470 0.429242 0.105 Uiso 0.2 1 calc R U P B 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
Ca1 O1 2.355(3) 8_465 ?
Ca1 O2 2.289(3) 2_656 ?
Ca1 O7 2.284(3) . ?
Ca1 O8 2.319(3) 5_666 ?
Ca1 O9 2.371(3) . ?
Ca1 O10 2.363(3) . ?
Ca1 C18 3.213(5) . ?
O1 C1 1.248(5) . ?
O2 C1 1.258(5) . ?
O3 N1 1.236(5) . ?
O4 N1 1.233(5) . ?
O5 N2 1.219(4) . ?
O6 N2 1.224(4) . ?
O7 C14 1.251(5) . ?
O8 C14 1.256(5) . ?
O9 C15 1.236(5) . ?
O10 C18 1.197(6) . ?
O10 C21 1.15(2) . ?
N1 C5 1.476(5) . ?
N2 C9 1.469(5) . ?
N3 C15 1.323(5) . ?
N3 C16 1.454(6) . ?
N3 C17 1.453(6) . ?
N4 C18 1.329(7) . ?
N4 C19 1.487(10) . ?
N4 C20 1.462(8) . ?
N5 C21 1.435(18) . ?
N5 C22 1.446(18) . ?
N5 C23 1.429(19) . ?
C1 C2 1.514(5) . ?
C2 C3 1.388(5) . ?
C2 C4 1.387(6) . ?
C3 H3 0.9300 . ?
C3 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C4 C6 1.396(5) . ?
C5 C7 1.378(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(5) . ?
C7 C8 1.498(5) . ?
C8 C9 1.401(5) . ?
C8 C10 1.389(6) . ?
C9 C12 1.375(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(5) . ?
C11 H11 0.9300 . ?
C11 C13 1.392(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(5) . ?
C13 C14 1.511(5) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 0.84(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
O1 Ca1 O9 90.19(11) 8_465 . ?
O1 Ca1 O10 79.71(11) 8_465 . ?
O1 Ca1 C18 66.18(12) 8_465 . ?
O2 Ca1 O1 102.59(10) 2_656 8_465 ?
O2 Ca1 O8 87.70(10) 2_656 5_666 ?
O2 Ca1 O9 86.14(10) 2_656 . ?
O2 Ca1 O10 177.40(11) 2_656 . ?
O2 Ca1 C18 163.30(12) 2_656 . ?
O7 Ca1 O1 162.09(11) . 8_465 ?
O7 Ca1 O2 94.66(10) . 2_656 ?
O7 Ca1 O8 103.72(11) . 5_666 ?
O7 Ca1 O9 86.16(10) . . ?
O7 Ca1 O10 83.16(11) . . ?
O7 Ca1 C18 97.93(12) . . ?
O8 Ca1 O1 81.99(11) 5_666 8_465 ?
O8 Ca1 O9 168.77(10) 5_666 . ?
O8 Ca1 O10 91.43(11) 5_666 . ?
O8 Ca1 C18 78.70(12) 5_666 . ?
O9 Ca1 C18 105.56(12) . . ?
O10 Ca1 O9 95.11(11) . . ?
O10 Ca1 C18 17.59(13) . . ?
C1 O1 Ca1 127.6(2) . 8_566 ?
C1 O2 Ca1 148.2(3) . 2_656 ?
C14 O7 Ca1 149.5(3) . . ?
C14 O8 Ca1 127.6(2) . 5_666 ?
C15 O9 Ca1 127.8(3) . . ?
C18 O10 Ca1 125.8(3) . . ?
C21 O10 Ca1 144.8(13) . . ?
O3 N1 C5 118.0(4) . . ?
O4 N1 O3 123.6(4) . . ?
O4 N1 C5 118.4(4) . . ?
O5 N2 O6 122.5(4) . . ?
O5 N2 C9 118.9(3) . . ?
O6 N2 C9 118.5(3) . . ?
C15 N3 C16 121.4(4) . . ?
C15 N3 C17 121.5(4) . . ?
C17 N3 C16 117.0(4) . . ?
C18 N4 C19 119.3(6) . . ?
C18 N4 C20 121.4(5) . . ?
C20 N4 C19 119.3(6) . . ?
C21 N5 C22 118(2) . . ?
C23 N5 C21 124(2) . . ?
C23 N5 C22 117(2) . . ?
O1 C1 O2 125.4(3) . . ?
O1 C1 C2 117.4(3) . . ?
O2 C1 C2 117.2(3) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C2 C1 121.0(3) . . ?
C4 C2 C3 118.7(3) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C5 119.0(4) . . ?
C5 C3 H3 120.5 . . ?
C2 C4 H4 119.5 . . ?
C2 C4 C6 121.0(4) . . ?
C6 C4 H4 119.5 . . ?
C3 C5 N1 117.2(4) . . ?
C7 C5 N1 119.3(3) . . ?
C7 C5 C3 123.4(4) . . ?
C4 C6 H6 119.5 . . ?
C7 C6 C4 120.9(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C7 C6 116.8(3) . . ?
C5 C7 C8 123.2(3) . . ?
C6 C7 C8 119.5(3) . . ?
C9 C8 C7 125.1(4) . . ?
C10 C8 C7 117.6(3) . . ?
C10 C8 C9 117.3(3) . . ?
C8 C9 N2 120.8(3) . . ?
C12 C9 N2 116.9(3) . . ?
C12 C9 C8 122.3(4) . . ?
C8 C10 H10 119.4 . . ?
C11 C10 C8 121.1(4) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C13 120.3(4) . . ?
C13 C11 H11 119.8 . . ?
C9 C12 H12 120.3 . . ?
C9 C12 C13 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C13 C14 121.0(3) . . ?
C12 C13 C11 119.4(3) . . ?
C12 C13 C14 119.6(3) . . ?
O7 C14 O8 126.2(3) . . ?
O7 C14 C13 116.8(3) . . ?
O8 C14 C13 117.0(3) . . ?
O9 C15 N3 124.7(4) . . ?
O9 C15 H15 117.6 . . ?
N3 C15 H15 117.6 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Ca1 C18 H18 87(4) . . ?
O10 C18 Ca1 36.6(2) . . ?
O10 C18 N4 125.5(5) . . ?
O10 C18 H18 122(4) . . ?
N4 C18 Ca1 160.6(4) . . ?
N4 C18 H18 112(4) . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O10 C21 N5 137(3) . . ?
O10 C21 H21 111.5 . . ?
N5 C21 H21 111.5 . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
N5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N5 C23 H23A 109.5 . . ?
N5 C23 H23B 109.5 . . ?
N5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Ca1 O1 C1 O2 -35.1(6) 8_566 . . . ?
Ca1 O1 C1 C2 146.3(3) 8_566 . . . ?
Ca1 O2 C1 O1 109.9(5) 2_656 . . . ?
Ca1 O2 C1 C2 -71.5(6) 2_656 . . . ?
Ca1 O7 C14 O8 -58.3(7) . . . . ?
Ca1 O7 C14 C13 123.6(4) . . . . ?
Ca1 O8 C14 O7 -29.8(6) 5_666 . . . ?
Ca1 O8 C14 C13 148.4(3) 5_666 . . . ?
Ca1 O9 C15 N3 -173.3(3) . . . . ?
Ca1 O10 C18 N4 -169.4(4) . . . . ?
Ca1 O10 C21 N5 164(2) . . . . ?
O1 C1 C2 C3 -8.4(5) . . . . ?
O1 C1 C2 C4 172.5(4) . . . . ?
O2 C1 C2 C3 172.8(4) . . . . ?
O2 C1 C2 C4 -6.3(5) . . . . ?
O3 N1 C5 C3 -38.9(6) . . . . ?
O3 N1 C5 C7 137.7(4) . . . . ?
O4 N1 C5 C3 142.5(4) . . . . ?
O4 N1 C5 C7 -41.0(6) . . . . ?
O5 N2 C9 C8 15.8(6) . . . . ?
O5 N2 C9 C12 -165.6(4) . . . . ?
O6 N2 C9 C8 -165.7(4) . . . . ?
O6 N2 C9 C12 12.9(6) . . . . ?
N1 C5 C7 C6 -174.5(4) . . . . ?
N1 C5 C7 C8 -2.0(6) . . . . ?
N2 C9 C12 C13 178.8(3) . . . . ?
C1 C2 C3 C5 178.3(4) . . . . ?
C1 C2 C4 C6 -179.4(4) . . . . ?
C2 C3 C5 N1 177.3(4) . . . . ?
C2 C3 C5 C7 0.9(6) . . . . ?
C2 C4 C6 C7 1.3(7) . . . . ?
C3 C2 C4 C6 1.5(6) . . . . ?
C3 C5 C7 C6 1.8(6) . . . . ?
C3 C5 C7 C8 174.3(4) . . . . ?
C4 C2 C3 C5 -2.5(6) . . . . ?
C4 C6 C7 C5 -2.9(6) . . . . ?
C4 C6 C7 C8 -175.6(4) . . . . ?
C5 C7 C8 C9 93.1(5) . . . . ?
C5 C7 C8 C10 -87.5(5) . . . . ?
C6 C7 C8 C9 -94.7(5) . . . . ?
C6 C7 C8 C10 84.8(5) . . . . ?
C7 C8 C9 N2 -0.4(6) . . . . ?
C7 C8 C9 C12 -179.0(4) . . . . ?
C7 C8 C10 C11 -178.8(4) . . . . ?
C8 C9 C12 C13 -2.6(6) . . . . ?
C8 C10 C11 C13 -1.8(6) . . . . ?
C9 C8 C10 C11 0.7(6) . . . . ?
C9 C12 C13 C11 1.4(6) . . . . ?
C9 C12 C13 C14 -178.3(4) . . . . ?
C10 C8 C9 N2 -179.9(4) . . . . ?
C10 C8 C9 C12 1.6(6) . . . . ?
C10 C11 C13 C12 0.8(6) . . . . ?
C10 C11 C13 C14 -179.5(3) . . . . ?
C11 C13 C14 O7 -17.4(5) . . . . ?
C11 C13 C14 O8 164.3(4) . . . . ?
C12 C13 C14 O7 162.3(4) . . . . ?
C12 C13 C14 O8 -16.1(5) . . . . ?
C16 N3 C15 O9 -1.6(7) . . . . ?
C17 N3 C15 O9 174.8(4) . . . . ?
C19 N4 C18 Ca1 -16.7(15) . . . . ?
C19 N4 C18 O10 2.6(10) . . . . ?
C20 N4 C18 Ca1 164.9(9) . . . . ?
C20 N4 C18 O10 -175.9(5) . . . . ?
C22 N5 C21 O10 173(3) . . . . ?
C23 N5 C21 O10 9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.801
_exptl_crystal_recrystallization_method Solvothermal
