# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ls_20190819_CaETI
_database_code_depnum_ccdc_archive 'CCDC 2025075'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_ls_20190819_CaETI   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A resolution cut-off of 0.96 A was imposed during refinement,
beyond which the crystal diffracted poorly. Attempts to grow better 
diffracting crystals were unsuccessful, as well as tests using Cu 
radiation in combination with low temperature measurements.
;
_vrf_PLAT029_ls_20190819_CaETI   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.958 Why?  
RESPONSE: Data were collected on a mar345 image plate with a single axis
of rotation, additional images were measured after changing manually the 
crystal orientation to increase the completeness and improve data 
statistics. The statistics of the second dataset were however much worse,
perhaps due to the twinning detected by platon, the additional images 
were therfore not used. 
;
_vrf_PLAT341_ls_20190819_CaETI   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01946 Ang.  
RESPONSE: A direct result of the diffraction quality of the crystal.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'CaCl2 (RS)-2-(2-Oxopyrrolidin-1-yl)butanamide pyridine-4-carboxamide'
_chemical_name_common            'CaCl2 etiracetam  Isonicotinamide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H36 Ca N6 O6, 2(Cl)'
_chemical_formula_sum            'C22 H36 Ca Cl2 N6 O6'
_chemical_formula_weight         591.55

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.968(2)
_cell_length_b                   12.170(4)
_cell_length_c                   15.304(4)
_cell_angle_alpha                87.17(2)
_cell_angle_beta                 86.30(2)
_cell_angle_gamma                74.76(2)
_cell_volume                     1428.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    784
_cell_measurement_theta_min      3.1230
_cell_measurement_theta_max      20.8700

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.453
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.98896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '120 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3208
_diffrn_reflns_av_unetI/netI     0.1081
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.033
_diffrn_reflns_theta_max         21.726
_diffrn_reflns_theta_full        21.726
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             3208
_reflns_number_gt                2033
_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.
;

_computing_data_collection       MAR
_computing_cell_refinement       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;



_refine_special_details          'Refined as a 2-component twin.,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)+(0.0610P)²+11.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     363
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.1544
_refine_ls_R_factor_gt           0.0989
_refine_ls_wR_factor_ref         0.2391
_refine_ls_wR_factor_gt          0.2139
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.092
_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
Ca1 Ca -0.1198(3) 0.2848(2) 0.25156(17) 0.0294(7) Uani 1 1 d . . . . .
Cl2 Cl 0.2762(5) 0.9694(3) 0.3419(3) 0.0644(12) Uani 1 1 d . . . . .
Cl3 Cl 0.7530(5) 0.9350(3) 0.1672(3) 0.0719(13) Uani 1 1 d . . . . .
O4 O -0.0664(11) 0.0863(7) 0.2596(6) 0.053(3) Uani 1 1 d . . . . .
H4A H 0.0309 0.0432 0.2513 0.080 Uiso 1 1 d R U . . .
H4B H -0.1312 0.0570 0.2349 0.080 Uiso 1 1 d R U . . .
O11 O 0.0450(12) 0.2836(7) 0.3691(6) 0.052(3) Uani 1 1 d . . . . .
C12 C 0.1101(17) 0.2296(10) 0.4357(9) 0.042(3) Uani 1 1 d . . . . .
C13 C 0.0229(17) 0.1620(12) 0.4963(10) 0.062(4) Uani 1 1 d . . . . .
H13A H -0.0234 0.1103 0.4648 0.075 Uiso 1 1 calc R U . . .
H13B H -0.0714 0.2110 0.5307 0.075 Uiso 1 1 calc R U . . .
C14 C 0.164(2) 0.0977(16) 0.5535(10) 0.084(6) Uani 1 1 d . . . . .
H14A H 0.2131 0.0209 0.5334 0.101 Uiso 1 1 calc R U . . .
H14B H 0.1197 0.0933 0.6138 0.101 Uiso 1 1 calc R U . . .
C15 C 0.3003(19) 0.1645(13) 0.5462(8) 0.061(4) Uani 1 1 d . . . . .
H15A H 0.2881 0.2139 0.5953 0.074 Uiso 1 1 calc R U . . .
H15B H 0.4171 0.1141 0.5434 0.074 Uiso 1 1 calc R U . . .
N16 N 0.2616(11) 0.2321(9) 0.4623(6) 0.037(3) Uani 1 1 d . . . . .
C17 C 0.3697(16) 0.2994(11) 0.4216(8) 0.045(4) Uani 1 1 d D U . . .
H17 H 0.2956 0.3407 0.3755 0.054 Uiso 1 1 calc R U . A 1
C18 C 0.5211(16) 0.2392(12) 0.3701(7) 0.034(3) Uani 1 1 d . . . . .
O19 O 0.6415(11) 0.2873(8) 0.3446(6) 0.057(3) Uani 1 1 d . . . . .
N20 N 0.5356(14) 0.1347(11) 0.3486(8) 0.061(4) Uani 1 1 d . . . . .
H20A H 0.6253 0.0987 0.3177 0.073 Uiso 1 1 calc R U . . .
H20B H 0.4554 0.1017 0.3655 0.073 Uiso 1 1 calc R U . . .
C21 C 0.391(4) 0.400(3) 0.475(3) 0.038(11) Uani 0.49(7) 1 d D U P B 1
H21A H 0.4642 0.3692 0.5234 0.045 Uiso 0.49(7) 1 calc R U P B 1
H21B H 0.4505 0.4461 0.4377 0.045 Uiso 0.49(7) 1 calc R U P B 1
C22 C 0.218(5) 0.477(4) 0.512(3) 0.061(13) Uani 0.49(7) 1 d D U P B 1
H22A H 0.1389 0.5001 0.4657 0.091 Uiso 0.49(7) 1 calc R U P B 1
H22B H 0.2392 0.5430 0.5361 0.091 Uiso 0.49(7) 1 calc R U P B 1
H22C H 0.1680 0.4356 0.5569 0.091 Uiso 0.49(7) 1 calc R U P B 1
C21B C 0.432(4) 0.356(4) 0.4977(19) 0.043(11) Uani 0.51(7) 1 d D U P B 2
H21C H 0.4867 0.2981 0.5400 0.052 Uiso 0.51(7) 1 calc R U P B 2
H21D H 0.5179 0.3953 0.4747 0.052 Uiso 0.51(7) 1 calc R U P B 2
C22B C 0.278(7) 0.442(4) 0.543(3) 0.069(15) Uani 0.51(7) 1 d D U P B 2
H22D H 0.2413 0.5085 0.5057 0.104 Uiso 0.51(7) 1 calc R U P B 2
H22E H 0.3145 0.4636 0.5972 0.104 Uiso 0.51(7) 1 calc R U P B 2
H22F H 0.1836 0.4077 0.5556 0.104 Uiso 0.51(7) 1 calc R U P B 2
O31 O 0.6994(11) 0.2853(7) 0.1384(6) 0.046(2) Uani 1 1 d . . . . .
C32 C 0.6928(16) 0.2307(11) 0.0706(8) 0.040(3) Uani 1 1 d . . . . .
C33 C 0.8456(18) 0.1696(14) 0.0149(10) 0.070(5) Uani 1 1 d . . . . .
H33A H 0.9333 0.1195 0.0501 0.084 Uiso 1 1 calc R U . . .
H33B H 0.8977 0.2227 -0.0192 0.084 Uiso 1 1 calc R U . . .
C34 C 0.7640(17) 0.1010(15) -0.0447(10) 0.074(5) Uani 1 1 d . . . . .
H34A H 0.8111 0.1042 -0.1046 0.089 Uiso 1 1 calc R U . . .
H34B H 0.7883 0.0219 -0.0245 0.089 Uiso 1 1 calc R U . . .
C35 C 0.5709(18) 0.1551(13) -0.0398(8) 0.057(4) Uani 1 1 d . . . . .
H35A H 0.5360 0.2050 -0.0905 0.069 Uiso 1 1 calc R U . . .
H35B H 0.5057 0.0979 -0.0355 0.069 Uiso 1 1 calc R U . . .
N36 N 0.5449(12) 0.2208(9) 0.0417(6) 0.041(3) Uani 1 1 d . . . . .
C37 C 0.3748(14) 0.2823(11) 0.0758(7) 0.038(3) Uani 1 1 d D . . . .
H37 H 0.3973 0.3397 0.1129 0.046 Uiso 1 1 calc R U . C 3
C38 C 0.2845(16) 0.2146(11) 0.1353(8) 0.036(3) Uani 1 1 d . . . . .
O39 O 0.1292(11) 0.2566(7) 0.1635(6) 0.051(3) Uani 1 1 d . . . . .
N40 N 0.3664(14) 0.1100(10) 0.1585(7) 0.053(3) Uani 1 1 d . . . . .
H40A H 0.3144 0.0699 0.1930 0.063 Uiso 1 1 calc R U . . .
H40B H 0.4720 0.0815 0.1393 0.063 Uiso 1 1 calc R U . . .
C41 C 0.252(4) 0.3520(14) 0.0063(15) 0.055(5) Uani 0.89(2) 1 d D U P D 3
H41A H 0.2444 0.3023 -0.0401 0.066 Uiso 0.89(2) 1 calc R U P D 3
H41B H 0.1365 0.3805 0.0334 0.066 Uiso 0.89(2) 1 calc R U P D 3
C42 C 0.315(3) 0.4488(16) -0.0320(12) 0.084(7) Uani 0.89(2) 1 d D U P D 3
H42A H 0.2357 0.4895 -0.0745 0.126 Uiso 0.89(2) 1 calc R U P D 3
H42B H 0.3206 0.4989 0.0135 0.126 Uiso 0.89(2) 1 calc R U P D 3
H42C H 0.4285 0.4208 -0.0599 0.126 Uiso 0.89(2) 1 calc R U P D 3
C41B C 0.26(3) 0.327(11) -0.001(11) 0.055(5) Uani 0.11(2) 1 d D . P D 4
H41C H 0.1688 0.2838 -0.0026 0.066 Uiso 0.11(2) 1 calc R U P D 4
H41D H 0.3240 0.3169 -0.0565 0.066 Uiso 0.11(2) 1 calc R U P D 4
C42B C 0.17(2) 0.449(10) 0.009(10) 0.084(7) Uani 0.11(2) 1 d D . P D 4
H42D H 0.0930 0.4759 -0.0393 0.126 Uiso 0.11(2) 1 calc R U P D 4
H42E H 0.0974 0.4586 0.0628 0.126 Uiso 0.11(2) 1 calc R U P D 4
H42F H 0.2523 0.4916 0.0091 0.126 Uiso 0.11(2) 1 calc R U P D 4
O51 O -0.1582(11) 0.4792(7) 0.2435(6) 0.048(2) Uani 1 1 d . . . . .
C52 C -0.1413(18) 0.5800(13) 0.2419(8) 0.045(3) Uani 1 1 d . . . . .
N53 N -0.2694(14) 0.6685(9) 0.2393(7) 0.046(3) Uani 1 1 d . . . . .
H53A H -0.3739 0.6616 0.2385 0.055 Uiso 1 1 calc R U . . .
H53B H -0.2512 0.7352 0.2383 0.055 Uiso 1 1 calc R U . . .
C54 C 0.0440(17) 0.5991(11) 0.2420(8) 0.042(3) Uani 1 1 d . . . . .
C55 C 0.1854(16) 0.5099(12) 0.2369(10) 0.054(4) Uani 1 1 d . . . . .
H55 H 0.1713 0.4367 0.2338 0.065 Uiso 1 1 calc R U . . .
C56 C 0.349(2) 0.5250(12) 0.2361(10) 0.062(4) Uani 1 1 d . . . . .
H56 H 0.4440 0.4625 0.2264 0.075 Uiso 1 1 calc R U . . .
N57 N 0.3803(17) 0.6269(11) 0.2489(8) 0.064(3) Uani 1 1 d . . . . .
C58 C 0.2386(18) 0.7137(12) 0.2570(11) 0.071(5) Uani 1 1 d . . . . .
H58 H 0.2532 0.7859 0.2644 0.085 Uiso 1 1 calc R U . . .
C59 C 0.0707(17) 0.7021(11) 0.2550(11) 0.062(4) Uani 1 1 d . . . . .
H59 H -0.0239 0.7652 0.2627 0.074 Uiso 1 1 calc R U . . .


_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 O39 2.283(9) . ?
Ca1 O11 2.292(9) . ?
Ca1 O19 2.295(9) 1_455 ?
Ca1 O51 2.302(9) . ?
Ca1 O31 2.321(9) 1_455 ?
Ca1 O4 2.339(8) . ?
O4 H4A 0.8200 . ?
O4 H4B 0.8200 . ?
O11 C12 1.249(15) . ?
C12 N16 1.306(15) . ?
C12 C13 1.471(17) . ?
C13 C14 1.50(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.51(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N16 1.495(15) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N16 C17 1.433(14) . ?
C17 C18 1.443(16) . ?
C17 C21B 1.554(14) . ?
C17 C21 1.556(14) . ?
C17 H17 0.9800 . ?
C18 O19 1.280(13) . ?
C18 N20 1.303(15) . ?
O19 Ca1 2.295(9) 1_655 ?
N20 H20A 0.8600 . ?
N20 H20B 0.8600 . ?
C21 C22 1.54(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21B C22B 1.54(2) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
O31 C32 1.272(14) . ?
O31 Ca1 2.321(9) 1_655 ?
C32 N36 1.321(15) . ?
C32 C33 1.488(17) . ?
C33 C34 1.546(19) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.504(18) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 N36 1.489(15) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
N36 C37 1.443(14) . ?
C37 C38 1.476(16) . ?
C37 C41 1.554(13) . ?
C37 C41B 1.554(15) . ?
C37 H37 0.9800 . ?
C38 O39 1.265(13) . ?
C38 N40 1.312(15) . ?
N40 H40A 0.8600 . ?
N40 H40B 0.8600 . ?
C41 C42 1.48(3) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C41B C42B 1.48(3) . ?
C41B H41C 0.9700 . ?
C41B H41D 0.9700 . ?
C42B H42D 0.9600 . ?
C42B H42E 0.9600 . ?
C42B H42F 0.9600 . ?
O51 C52 1.268(14) . ?
C52 N53 1.276(16) . ?
C52 C54 1.553(18) . ?
N53 H53A 0.8600 . ?
N53 H53B 0.8600 . ?
C54 C55 1.345(16) . ?
C54 C59 1.352(17) . ?
C55 C56 1.367(18) . ?
C55 H55 0.9300 . ?
C56 N57 1.351(17) . ?
C56 H56 0.9300 . ?
N57 C58 1.332(16) . ?
C58 C59 1.384(18) . ?
C58 H58 0.9300 . ?
C59 H59 0.9300 . ?

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
O39 Ca1 O11 88.4(3) . . ?
O39 Ca1 O19 172.3(3) . 1_455 ?
O11 Ca1 O19 90.2(3) . 1_455 ?
O39 Ca1 O51 91.5(3) . . ?
O11 Ca1 O51 86.5(3) . . ?
O19 Ca1 O51 96.0(3) 1_455 . ?
O39 Ca1 O31 95.0(3) . 1_455 ?
O11 Ca1 O31 176.5(4) . 1_455 ?
O19 Ca1 O31 86.3(3) 1_455 1_455 ?
O51 Ca1 O31 94.1(3) . 1_455 ?
O39 Ca1 O4 86.3(3) . . ?
O11 Ca1 O4 91.9(3) . . ?
O19 Ca1 O4 86.2(3) 1_455 . ?
O51 Ca1 O4 177.3(3) . . ?
O31 Ca1 O4 87.7(3) 1_455 . ?
Ca1 O4 H4A 123.1 . . ?
Ca1 O4 H4B 118.4 . . ?
H4A O4 H4B 104.5 . . ?
C12 O11 Ca1 146.3(8) . . ?
O11 C12 N16 123.4(11) . . ?
O11 C12 C13 124.7(12) . . ?
N16 C12 C13 111.8(13) . . ?
C12 C13 C14 103.9(12) . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
C14 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C13 C14 C15 105.2(12) . . ?
C13 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
N16 C15 C14 102.9(11) . . ?
N16 C15 H15A 111.2 . . ?
C14 C15 H15A 111.2 . . ?
N16 C15 H15B 111.2 . . ?
C14 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C12 N16 C17 124.8(11) . . ?
C12 N16 C15 111.2(10) . . ?
C17 N16 C15 123.8(10) . . ?
N16 C17 C18 116.5(11) . . ?
N16 C17 C21B 105.8(16) . . ?
C18 C17 C21B 108.4(15) . . ?
N16 C17 C21 116.3(16) . . ?
C18 C17 C21 116.6(13) . . ?
N16 C17 H17 101.0 . . ?
C18 C17 H17 101.0 . . ?
C21 C17 H17 101.0 . . ?
O19 C18 N20 119.3(11) . . ?
O19 C18 C17 120.9(12) . . ?
N20 C18 C17 119.8(11) . . ?
C18 O19 Ca1 147.3(9) . 1_655 ?
C18 N20 H20A 120.0 . . ?
C18 N20 H20B 120.0 . . ?
H20A N20 H20B 120.0 . . ?
C22 C21 C17 114(2) . . ?
C22 C21 H21A 108.7 . . ?
C17 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C17 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C22B C21B C17 111(2) . . ?
C22B C21B H21C 109.4 . . ?
C17 C21B H21C 109.4 . . ?
C22B C21B H21D 109.4 . . ?
C17 C21B H21D 109.4 . . ?
H21C C21B H21D 108.0 . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C32 O31 Ca1 140.6(8) . 1_655 ?
O31 C32 N36 122.8(11) . . ?
O31 C32 C33 125.6(12) . . ?
N36 C32 C33 111.7(12) . . ?
C32 C33 C34 102.5(11) . . ?
C32 C33 H33A 111.3 . . ?
C34 C33 H33A 111.3 . . ?
C32 C33 H33B 111.3 . . ?
C34 C33 H33B 111.3 . . ?
H33A C33 H33B 109.2 . . ?
C35 C34 C33 106.5(12) . . ?
C35 C34 H34A 110.4 . . ?
C33 C34 H34A 110.4 . . ?
C35 C34 H34B 110.4 . . ?
C33 C34 H34B 110.4 . . ?
H34A C34 H34B 108.6 . . ?
N36 C35 C34 102.9(11) . . ?
N36 C35 H35A 111.2 . . ?
C34 C35 H35A 111.2 . . ?
N36 C35 H35B 111.2 . . ?
C34 C35 H35B 111.2 . . ?
H35A C35 H35B 109.1 . . ?
C32 N36 C37 124.0(11) . . ?
C32 N36 C35 112.7(11) . . ?
C37 N36 C35 122.5(10) . . ?
N36 C37 C38 114.8(11) . . ?
N36 C37 C41 115.1(14) . . ?
C38 C37 C41 111.5(15) . . ?
N36 C37 C41B 109(9) . . ?
C38 C37 C41B 107(10) . . ?
N36 C37 H37 104.7 . . ?
C38 C37 H37 104.7 . . ?
C41 C37 H37 104.7 . . ?
O39 C38 N40 120.0(11) . . ?
O39 C38 C37 120.5(12) . . ?
N40 C38 C37 119.5(11) . . ?
C38 O39 Ca1 160.0(8) . . ?
C38 N40 H40A 120.0 . . ?
C38 N40 H40B 120.0 . . ?
H40A N40 H40B 120.0 . . ?
C42 C41 C37 112.1(17) . . ?
C42 C41 H41A 109.2 . . ?
C37 C41 H41A 109.2 . . ?
C42 C41 H41B 109.2 . . ?
C37 C41 H41B 109.2 . . ?
H41A C41 H41B 107.9 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C37 C41B C42B 110(8) . . ?
C37 C41B H41C 109.7 . . ?
C42B C41B H41C 109.7 . . ?
C37 C41B H41D 109.7 . . ?
C42B C41B H41D 109.7 . . ?
H41C C41B H41D 108.2 . . ?
C41B C42B H42D 109.5 . . ?
C41B C42B H42E 109.5 . . ?
H42D C42B H42E 109.5 . . ?
C41B C42B H42F 109.5 . . ?
H42D C42B H42F 109.5 . . ?
H42E C42B H42F 109.5 . . ?
C52 O51 Ca1 166.5(9) . . ?
O51 C52 N53 123.5(13) . . ?
O51 C52 C54 119.3(12) . . ?
N53 C52 C54 117.2(12) . . ?
C52 N53 H53A 120.0 . . ?
C52 N53 H53B 120.0 . . ?
H53A N53 H53B 120.0 . . ?
C55 C54 C59 117.1(13) . . ?
C55 C54 C52 120.2(12) . . ?
C59 C54 C52 122.4(12) . . ?
C54 C55 C56 121.0(13) . . ?
C54 C55 H55 119.5 . . ?
C56 C55 H55 119.5 . . ?
N57 C56 C55 122.9(13) . . ?
N57 C56 H56 118.5 . . ?
C55 C56 H56 118.5 . . ?
C58 N57 C56 115.1(13) . . ?
N57 C58 C59 123.5(13) . . ?
N57 C58 H58 118.3 . . ?
C59 C58 H58 118.3 . . ?
C54 C59 C58 120.1(13) . . ?
C54 C59 H59 120.0 . . ?
C58 C59 H59 120.0 . . ?

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 O11 C12 N16 144.4(12) . . . . ?
Ca1 O11 C12 C13 -40(2) . . . . ?
O11 C12 C13 C14 169.5(14) . . . . ?
N16 C12 C13 C14 -14.1(16) . . . . ?
C12 C13 C14 C15 21.5(17) . . . . ?
C13 C14 C15 N16 -21.1(17) . . . . ?
O11 C12 N16 C17 3(2) . . . . ?
C13 C12 N16 C17 -173.9(12) . . . . ?
O11 C12 N16 C15 176.8(12) . . . . ?
C13 C12 N16 C15 0.4(15) . . . . ?
C14 C15 N16 C12 13.3(16) . . . . ?
C14 C15 N16 C17 -172.4(13) . . . . ?
C12 N16 C17 C18 -105.3(15) . . . . ?
C15 N16 C17 C18 81.2(15) . . . . ?
C12 N16 C17 C21B 134(2) . . . . ?
C15 N16 C17 C21B -39(2) . . . . ?
C12 N16 C17 C21 111(2) . . . . ?
C15 N16 C17 C21 -62(3) . . . . ?
N16 C17 C18 O19 -167.2(11) . . . . ?
C21B C17 C18 O19 -48(2) . . . . ?
C21 C17 C18 O19 -24(3) . . . . ?
N16 C17 C18 N20 13.1(17) . . . . ?
C21B C17 C18 N20 132(2) . . . . ?
C21 C17 C18 N20 156(2) . . . . ?
N20 C18 O19 Ca1 16(2) . . . 1_655 ?
C17 C18 O19 Ca1 -163.7(11) . . . 1_655 ?
N16 C17 C21 C22 -49(3) . . . . ?
C18 C17 C21 C22 167(2) . . . . ?
N16 C17 C21B C22B -66(3) . . . . ?
C18 C17 C21B C22B 168(2) . . . . ?
Ca1 O31 C32 N36 149.2(9) 1_655 . . . ?
Ca1 O31 C32 C33 -30(2) 1_655 . . . ?
O31 C32 C33 C34 169.2(13) . . . . ?
N36 C32 C33 C34 -10.1(16) . . . . ?
C32 C33 C34 C35 17.9(17) . . . . ?
C33 C34 C35 N36 -18.8(16) . . . . ?
O31 C32 N36 C37 8.6(18) . . . . ?
C33 C32 N36 C37 -172.1(11) . . . . ?
O31 C32 N36 C35 178.7(11) . . . . ?
C33 C32 N36 C35 -1.9(15) . . . . ?
C34 C35 N36 C32 13.4(16) . . . . ?
C34 C35 N36 C37 -176.3(12) . . . . ?
C32 N36 C37 C38 -102.9(14) . . . . ?
C35 N36 C37 C38 87.9(14) . . . . ?
C32 N36 C37 C41 125.6(14) . . . . ?
C35 N36 C37 C41 -43.6(18) . . . . ?
C32 N36 C37 C41B 137(8) . . . . ?
C35 N36 C37 C41B -32(8) . . . . ?
N36 C37 C38 O39 -174.2(11) . . . . ?
C41 C37 C38 O39 -41.0(18) . . . . ?
C41B C37 C38 O39 -53(6) . . . . ?
N36 C37 C38 N40 5.5(17) . . . . ?
C41 C37 C38 N40 138.7(14) . . . . ?
C41B C37 C38 N40 127(6) . . . . ?
N40 C38 O39 Ca1 24(3) . . . . ?
C37 C38 O39 Ca1 -156.5(18) . . . . ?
N36 C37 C41 C42 -68(2) . . . . ?
C38 C37 C41 C42 159.4(18) . . . . ?
N36 C37 C41B C42B -131(15) . . . . ?
C38 C37 C41B C42B 104(16) . . . . ?
Ca1 O51 C52 N53 -173(3) . . . . ?
Ca1 O51 C52 C54 8(4) . . . . ?
O51 C52 C54 C55 5.2(18) . . . . ?
N53 C52 C54 C55 -174.2(13) . . . . ?
O51 C52 C54 C59 -168.7(13) . . . . ?
N53 C52 C54 C59 12.0(19) . . . . ?
C59 C54 C55 C56 -6(2) . . . . ?
C52 C54 C55 C56 179.5(13) . . . . ?
C54 C55 C56 N57 7(2) . . . . ?
C55 C56 N57 C58 -4(2) . . . . ?
C56 N57 C58 C59 2(2) . . . . ?
C55 C54 C59 C58 4(2) . . . . ?
C52 C54 C59 C58 178.1(14) . . . . ?
N57 C58 C59 C54 -2(3) . . . . ?

_refine_diff_density_max         0.751
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.101


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_ls_R2B6CaCl2
_database_code_depnum_ccdc_archive 'CCDC 2025077'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'CaCl2 (S)-2-(2-oxopyrrolidin-1-yl)butanamide pyridine-3-carboxamide'
_chemical_name_common            'CaCl2 Levetiracetam Nicotinamide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H36 Ca N6 O6, 2(Cl)'
_chemical_formula_sum            'C22 H36 Ca Cl2 N6 O6'
_chemical_formula_weight         591.55

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'
Cl Cl 0.1484 0.1585 '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                   11.9243(5)
_cell_length_b                   8.0669(3)
_cell_length_c                   15.4348(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.338(4)
_cell_angle_gamma                90
_cell_volume                     1483.46(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4820
_cell_measurement_theta_min      3.0430
_cell_measurement_theta_max      25.6090

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.436
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.62749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '100 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11004
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_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         3.050
_diffrn_reflns_theta_max         25.691
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5624
_reflns_number_gt                4624
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.992

_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       MAR
_computing_cell_refinement       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;



_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)+(0.0394P)²+0.1892P] 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_abs_structure_details 
;
 Flack x determined using 1707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5624
_refine_ls_number_parameters     349
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_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
Ca1 Ca 0.26773(6) 0.49650(10) 0.74852(6) 0.0344(2) Uani 1 1 d . . . . .
Cl2 Cl 0.96509(10) 0.77222(16) 0.64855(9) 0.0612(4) Uani 1 1 d . . . . .
Cl3 Cl 0.93897(10) 0.22523(16) 0.83021(10) 0.0643(4) Uani 1 1 d . . . . .
O4 O 0.2746(3) 0.3331(4) 0.8700(2) 0.0599(10) Uani 1 1 d . . . . .
C5 C 0.2251(4) 0.2733(6) 0.9309(3) 0.0427(10) Uani 1 1 d . . . . .
C6 C 0.1598(5) 0.3643(7) 0.9961(4) 0.0708(17) Uani 1 1 d . . . . .
H6A H 0.2093 0.4291 1.0342 0.085 Uiso 1 1 calc R U . . .
H6B H 0.1056 0.4380 0.9677 0.085 Uiso 1 1 calc R U . . .
C7 C 0.1019(5) 0.2339(9) 1.0457(4) 0.0797(18) Uani 1 1 d . . . . .
H7A H 0.0236 0.2256 1.0266 0.096 Uiso 1 1 calc R U . . .
H7B H 0.1061 0.2586 1.1073 0.096 Uiso 1 1 calc R U . . .
C8 C 0.1640(5) 0.0730(7) 1.0272(3) 0.0581(14) Uani 1 1 d . . . . .
H8A H 0.2157 0.0440 1.0750 0.070 Uiso 1 1 calc R U . . .
H8B H 0.1119 -0.0178 1.0169 0.070 Uiso 1 1 calc R U . . .
N9 N 0.2242(3) 0.1119(4) 0.9493(2) 0.0360(8) Uani 1 1 d . . . . .
C10 C 0.2896(3) -0.0099(6) 0.9034(3) 0.0361(8) Uani 1 1 d . . . . .
H10 H 0.3339 0.0519 0.8621 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2162(4) -0.1294(5) 0.8504(3) 0.0370(10) Uani 1 1 d . . . . .
O12 O 0.2596(3) -0.2569(4) 0.8228(2) 0.0577(9) Uani 1 1 d . . . . .
N13 N 0.1109(3) -0.0911(5) 0.8320(2) 0.0475(10) Uani 1 1 d . . . . .
H13A H 0.0699 -0.1557 0.7997 0.057 Uiso 1 1 calc R U . . .
H13B H 0.0830 -0.0014 0.8522 0.057 Uiso 1 1 calc R U . . .
C14 C 0.3727(4) -0.1001(7) 0.9639(4) 0.0625(14) Uani 1 1 d . . . . .
H14A H 0.4106 -0.1850 0.9315 0.075 Uiso 1 1 calc R U . . .
H14B H 0.3322 -0.1545 1.0091 0.075 Uiso 1 1 calc R U . . .
C15 C 0.4603(5) 0.0168(10) 1.0055(4) 0.088(2) Uani 1 1 d . . . . .
H15A H 0.5019 0.0688 0.9610 0.132 Uiso 1 1 calc R U . . .
H15B H 0.5106 -0.0452 1.0433 0.132 Uiso 1 1 calc R U . . .
H15C H 0.4233 0.1002 1.0383 0.132 Uiso 1 1 calc R U . . .
O16 O 0.2747(3) 0.6572(4) 0.6265(2) 0.0532(9) Uani 1 1 d . . . . .
C17 C 0.2311(3) 0.7230(5) 0.5618(3) 0.0379(10) Uani 1 1 d . . . . .
C18 C 0.1668(5) 0.6380(7) 0.4893(4) 0.0659(16) Uani 1 1 d . . . . .
H18A H 0.1086 0.5674 0.5114 0.079 Uiso 1 1 calc R U . . .
H18B H 0.2161 0.5716 0.4549 0.079 Uiso 1 1 calc R U . . .
C19 C 0.1166(6) 0.7793(9) 0.4367(4) 0.086(2) Uani 1 1 d . . . . .
H19A H 0.1210 0.7568 0.3752 0.104 Uiso 1 1 calc R U . . .
H19B H 0.0385 0.7950 0.4499 0.104 Uiso 1 1 calc R U . . .
C20 C 0.1835(5) 0.9290(7) 0.4612(3) 0.0655(15) Uani 1 1 d . . . . .
H20A H 0.2392 0.9520 0.4187 0.079 Uiso 1 1 calc R U . . .
H20B H 0.1355 1.0252 0.4664 0.079 Uiso 1 1 calc R U . . .
N21 N 0.2368(3) 0.8848(4) 0.5449(2) 0.0366(8) Uani 1 1 d . . . . .
C22 C 0.3037(3) 1.0004(6) 0.5976(3) 0.0429(10) Uani 1 1 d . . . . .
H22 H 0.3412 0.9347 0.6437 0.052 Uiso 1 1 calc R U . . .
C23 C 0.2342(4) 1.1288(5) 0.6423(3) 0.0425(11) Uani 1 1 d . . . . .
O24 O 0.2804(3) 1.2549(4) 0.6704(3) 0.0656(10) Uani 1 1 d . . . . .
N25 N 0.1269(3) 1.0982(5) 0.6511(3) 0.0577(11) Uani 1 1 d . . . . .
H25A H 0.0859 1.1682 0.6776 0.069 Uiso 1 1 calc R U . . .
H25B H 0.0977 1.0083 0.6305 0.069 Uiso 1 1 calc R U . . .
C26 C 0.3965(5) 1.0812(7) 0.5470(5) 0.0790(19) Uani 1 1 d . . . . .
H26A H 0.3626 1.1446 0.4994 0.095 Uiso 1 1 calc R U . . .
H26B H 0.4377 1.1579 0.5849 0.095 Uiso 1 1 calc R U . . .
C27 C 0.4777(6) 0.9583(9) 0.5113(6) 0.105(3) Uani 1 1 d . . . . .
H27A H 0.5164 0.9015 0.5583 0.158 Uiso 1 1 calc R U . . .
H27B H 0.5312 1.0156 0.4773 0.158 Uiso 1 1 calc R U . . .
H27C H 0.4374 0.8793 0.4754 0.158 Uiso 1 1 calc R U . . .
N28 N 0.4753(3) 0.5279(4) 0.7537(2) 0.0439(9) Uani 1 1 d . . . A 1
C29 C 0.5517(4) 0.4084(6) 0.7541(3) 0.0503(12) Uani 1 1 d . . . A 1
H29 H 0.5267 0.2992 0.7552 0.060 Uiso 1 1 calc R U . A 1
C30 C 0.6647(4) 0.4354(6) 0.7532(3) 0.0533(13) Uani 1 1 d . . . A 1
H30 H 0.7146 0.3467 0.7532 0.064 Uiso 1 1 calc R U . A 1
C31 C 0.7040(4) 0.5976(6) 0.7523(3) 0.0468(11) Uani 1 1 d . . . A 1
H31 H 0.7803 0.6199 0.7502 0.056 Uiso 1 1 calc R U . A 1
C32 C 0.6269(3) 0.7239(5) 0.7544(3) 0.0395(10) Uani 1 1 d D . . A 1
C33 C 0.5144(4) 0.6846(6) 0.7549(3) 0.0455(11) Uani 1 1 d . . . A 1
H33 H 0.4628 0.7709 0.7561 0.055 Uiso 1 1 calc R U . A 1
C34 C 0.6571(8) 0.9057(7) 0.7654(10) 0.057(2) Uani 0.90(5) 1 d D . P A 1
O35 O 0.5875(6) 1.0018(10) 0.7912(16) 0.100(4) Uani 0.90(5) 1 d D . P A 1
N36 N 0.7613(5) 0.9484(11) 0.7500(14) 0.063(3) Uani 0.90(5) 1 d D . P A 1
H36A H 0.7831 1.0491 0.7582 0.076 Uiso 0.90(5) 1 calc R U P A 1
H36B H 0.8075 0.8756 0.7317 0.076 Uiso 0.90(5) 1 calc R U P A 1
C34B C 0.664(7) 0.904(3) 0.750(10) 0.057(2) Uani 0.10(5) 1 d DG . P A 2
O35B O 0.589(6) 1.006(10) 0.751(10) 0.100(4) Uani 0.10(5) 1 d DG . P A 2
N36B N 0.762(5) 0.932(11) 0.716(8) 0.063(3) Uani 0.10(5) 1 d DG . P A 2
H36C H 0.7755 1.0262 0.6933 0.076 Uiso 0.10(5) 1 calc R U P A 2
H36D H 0.8119 0.8549 0.7171 0.076 Uiso 0.10(5) 1 calc R U P A 2
O37 O 0.0746(3) 0.4768(7) 0.7381(4) 0.0923(17) Uani 1 1 d . . . . .
H37A H 0.043(7) 0.417(12) 0.768(6) 0.138 Uiso 1 1 d . U . . .
H37B H 0.039(7) 0.558(11) 0.721(6) 0.138 Uiso 1 1 d . U . . .


_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 O4 2.290(4) . ?
Ca1 O16 2.291(3) . ?
Ca1 O24 2.300(3) 1_545 ?
Ca1 O12 2.300(3) 1_565 ?
Ca1 O37 2.308(4) . ?
Ca1 N28 2.486(3) . ?
Ca1 H37A 2.78(9) . ?
Ca1 H37B 2.79(8) . ?
O4 C5 1.229(6) . ?
C5 N9 1.333(6) . ?
C5 C6 1.492(7) . ?
C6 C7 1.487(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.527(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N9 1.460(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N9 C10 1.456(5) . ?
C10 C14 1.519(6) . ?
C10 C11 1.519(6) . ?
C10 H10 0.9800 . ?
C11 O12 1.236(5) . ?
C11 N13 1.312(6) . ?
O12 Ca1 2.300(3) 1_545 ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
C14 C15 1.528(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O16 C17 1.227(5) . ?
C17 N21 1.333(6) . ?
C17 C18 1.496(6) . ?
C18 C19 1.508(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.487(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N21 1.461(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
N21 C22 1.454(5) . ?
C22 C23 1.511(6) . ?
C22 C26 1.527(7) . ?
C22 H22 0.9800 . ?
C23 O24 1.228(5) . ?
C23 N25 1.315(6) . ?
O24 Ca1 2.300(3) 1_565 ?
N25 H25A 0.8600 . ?
N25 H25B 0.8600 . ?
C26 C27 1.506(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N28 C29 1.326(6) . ?
N28 C33 1.348(6) . ?
C29 C30 1.366(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.390(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.373(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.379(6) . ?
C32 C34 1.518(7) . ?
C33 H33 0.9300 . ?
C34 O35 1.214(7) . ?
C34 N36 1.320(7) . ?
N36 H36A 0.8600 . ?
N36 H36B 0.8600 . ?
C34B O35B 1.2088 . ?
C34B N36B 1.3199 . ?
N36B H36C 0.8600 . ?
N36B H36D 0.8600 . ?
O37 H37A 0.78(9) . ?
O37 H37B 0.82(9) . ?

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
O4 Ca1 O16 175.80(13) . . ?
O4 Ca1 O24 86.59(14) . 1_545 ?
O16 Ca1 O24 92.48(14) . 1_545 ?
O4 Ca1 O12 95.19(14) . 1_565 ?
O16 Ca1 O12 85.65(13) . 1_565 ?
O24 Ca1 O12 177.73(15) 1_545 1_565 ?
O4 Ca1 O37 91.14(16) . . ?
O16 Ca1 O37 92.94(15) . . ?
O24 Ca1 O37 89.55(19) 1_545 . ?
O12 Ca1 O37 91.83(18) 1_565 . ?
O4 Ca1 N28 91.71(13) . . ?
O16 Ca1 N28 84.21(12) . . ?
O24 Ca1 N28 90.93(12) 1_545 . ?
O12 Ca1 N28 87.61(12) 1_565 . ?
O37 Ca1 N28 177.13(16) . . ?
O4 Ca1 H37A 77.4(19) . . ?
O16 Ca1 H37A 106.7(19) . . ?
O24 Ca1 H37A 86.9(19) 1_545 . ?
O12 Ca1 H37A 94.9(19) 1_565 . ?
O37 Ca1 H37A 13.9(19) . . ?
N28 Ca1 H37A 169.0(19) . . ?
O4 Ca1 H37B 103.3(18) . . ?
O16 Ca1 H37B 80.9(18) . . ?
O24 Ca1 H37B 99.0(19) 1_545 . ?
O12 Ca1 H37B 82.0(19) 1_565 . ?
O37 Ca1 H37B 15.1(19) . . ?
N28 Ca1 H37B 162.4(19) . . ?
H37A Ca1 H37B 28(2) . . ?
C5 O4 Ca1 148.2(3) . . ?
O4 C5 N9 123.7(4) . . ?
O4 C5 C6 127.1(5) . . ?
N9 C5 C6 109.1(5) . . ?
C7 C6 C5 105.4(4) . . ?
C7 C6 H6A 110.7 . . ?
C5 C6 H6A 110.7 . . ?
C7 C6 H6B 110.7 . . ?
C5 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C6 C7 C8 105.4(4) . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
N9 C8 C7 103.3(4) . . ?
N9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
N9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C5 N9 C10 123.1(4) . . ?
C5 N9 C8 113.2(4) . . ?
C10 N9 C8 123.2(4) . . ?
N9 C10 C14 111.9(3) . . ?
N9 C10 C11 112.4(3) . . ?
C14 C10 C11 112.0(4) . . ?
N9 C10 H10 106.7 . . ?
C14 C10 H10 106.7 . . ?
C11 C10 H10 106.7 . . ?
O12 C11 N13 122.1(4) . . ?
O12 C11 C10 118.3(4) . . ?
N13 C11 C10 119.5(4) . . ?
C11 O12 Ca1 156.8(3) . 1_545 ?
C11 N13 H13A 120.0 . . ?
C11 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C10 C14 C15 112.3(5) . . ?
C10 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C10 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 O16 Ca1 152.2(3) . . ?
O16 C17 N21 124.0(4) . . ?
O16 C17 C18 126.7(4) . . ?
N21 C17 C18 109.3(4) . . ?
C17 C18 C19 103.7(4) . . ?
C17 C18 H18A 111.0 . . ?
C19 C18 H18A 111.0 . . ?
C17 C18 H18B 111.0 . . ?
C19 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C20 C19 C18 106.3(4) . . ?
C20 C19 H19A 110.5 . . ?
C18 C19 H19A 110.5 . . ?
C20 C19 H19B 110.5 . . ?
C18 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
N21 C20 C19 103.6(4) . . ?
N21 C20 H20A 111.0 . . ?
C19 C20 H20A 111.0 . . ?
N21 C20 H20B 111.0 . . ?
C19 C20 H20B 111.0 . . ?
H20A C20 H20B 109.0 . . ?
C17 N21 C22 123.4(4) . . ?
C17 N21 C20 112.8(4) . . ?
C22 N21 C20 123.2(4) . . ?
N21 C22 C23 113.4(3) . . ?
N21 C22 C26 112.4(4) . . ?
C23 C22 C26 111.3(4) . . ?
N21 C22 H22 106.4 . . ?
C23 C22 H22 106.4 . . ?
C26 C22 H22 106.4 . . ?
O24 C23 N25 122.9(4) . . ?
O24 C23 C22 118.9(4) . . ?
N25 C23 C22 118.2(4) . . ?
C23 O24 Ca1 148.1(3) . 1_565 ?
C23 N25 H25A 120.0 . . ?
C23 N25 H25B 120.0 . . ?
H25A N25 H25B 120.0 . . ?
C27 C26 C22 113.4(5) . . ?
C27 C26 H26A 108.9 . . ?
C22 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C22 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 N28 C33 116.4(4) . . ?
C29 N28 Ca1 127.5(3) . . ?
C33 N28 Ca1 116.1(3) . . ?
N28 C29 C30 124.2(5) . . ?
N28 C29 H29 117.9 . . ?
C30 C29 H29 117.9 . . ?
C29 C30 C31 118.9(4) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C32 C31 C30 118.2(4) . . ?
C32 C31 H31 120.9 . . ?
C30 C31 H31 120.9 . . ?
C31 C32 C33 118.7(4) . . ?
C31 C32 C34 124.3(5) . . ?
C33 C32 C34 116.6(5) . . ?
N28 C33 C32 123.6(4) . . ?
N28 C33 H33 118.2 . . ?
C32 C33 H33 118.2 . . ?
O35 C34 N36 123.6(8) . . ?
O35 C34 C32 119.4(7) . . ?
N36 C34 C32 116.9(6) . . ?
C34 N36 H36A 120.0 . . ?
C34 N36 H36B 120.0 . . ?
H36A N36 H36B 120.0 . . ?
O35B C34B N36B 123.7 . . ?
C34B N36B H36C 120.0 . . ?
C34B N36B H36D 120.0 . . ?
H36C N36B H36D 120.0 . . ?
Ca1 O37 H37A 121(7) . . ?
Ca1 O37 H37B 118(6) . . ?
H37A O37 H37B 115(8) . . ?

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 O4 C5 N9 127.1(5) . . . . ?
Ca1 O4 C5 C6 -54.3(9) . . . . ?
O4 C5 C6 C7 170.8(5) . . . . ?
N9 C5 C6 C7 -10.4(6) . . . . ?
C5 C6 C7 C8 17.5(6) . . . . ?
C6 C7 C8 N9 -18.1(6) . . . . ?
O4 C5 N9 C10 5.2(7) . . . . ?
C6 C5 N9 C10 -173.6(4) . . . . ?
O4 C5 N9 C8 177.2(4) . . . . ?
C6 C5 N9 C8 -1.7(6) . . . . ?
C7 C8 N9 C5 12.6(6) . . . . ?
C7 C8 N9 C10 -175.5(4) . . . . ?
C5 N9 C10 C14 119.6(5) . . . . ?
C8 N9 C10 C14 -51.5(6) . . . . ?
C5 N9 C10 C11 -113.3(5) . . . . ?
C8 N9 C10 C11 75.5(5) . . . . ?
N9 C10 C11 O12 -165.8(4) . . . . ?
C14 C10 C11 O12 -38.8(6) . . . . ?
N9 C10 C11 N13 17.3(6) . . . . ?
C14 C10 C11 N13 144.4(4) . . . . ?
N13 C11 O12 Ca1 -0.9(11) . . . 1_545 ?
C10 C11 O12 Ca1 -177.6(6) . . . 1_545 ?
N9 C10 C14 C15 -62.8(6) . . . . ?
C11 C10 C14 C15 169.9(4) . . . . ?
Ca1 O16 C17 N21 125.5(6) . . . . ?
Ca1 O16 C17 C18 -56.2(9) . . . . ?
O16 C17 C18 C19 170.6(5) . . . . ?
N21 C17 C18 C19 -10.9(6) . . . . ?
C17 C18 C19 C20 19.2(6) . . . . ?
C18 C19 C20 N21 -20.3(6) . . . . ?
O16 C17 N21 C22 5.4(7) . . . . ?
C18 C17 N21 C22 -173.1(4) . . . . ?
O16 C17 N21 C20 176.5(4) . . . . ?
C18 C17 N21 C20 -2.1(5) . . . . ?
C19 C20 N21 C17 14.3(6) . . . . ?
C19 C20 N21 C22 -174.6(4) . . . . ?
C17 N21 C22 C23 -115.5(5) . . . . ?
C20 N21 C22 C23 74.3(5) . . . . ?
C17 N21 C22 C26 117.2(5) . . . . ?
C20 N21 C22 C26 -53.0(6) . . . . ?
N21 C22 C23 O24 -162.3(4) . . . . ?
C26 C22 C23 O24 -34.4(6) . . . . ?
N21 C22 C23 N25 19.3(6) . . . . ?
C26 C22 C23 N25 147.2(5) . . . . ?
N25 C23 O24 Ca1 4.8(10) . . . 1_565 ?
C22 C23 O24 Ca1 -173.5(4) . . . 1_565 ?
N21 C22 C26 C27 -59.4(7) . . . . ?
C23 C22 C26 C27 172.2(6) . . . . ?
C33 N28 C29 C30 -2.0(7) . . . . ?
Ca1 N28 C29 C30 177.0(4) . . . . ?
N28 C29 C30 C31 0.4(8) . . . . ?
C29 C30 C31 C32 1.6(7) . . . . ?
C30 C31 C32 C33 -1.8(7) . . . . ?
C30 C31 C32 C34 171.7(8) . . . . ?
C29 N28 C33 C32 1.6(7) . . . . ?
Ca1 N28 C33 C32 -177.4(3) . . . . ?
C31 C32 C33 N28 0.3(7) . . . . ?
C34 C32 C33 N28 -173.8(7) . . . . ?
C31 C32 C34 O35 -158.9(13) . . . . ?
C33 C32 C34 O35 14.8(16) . . . . ?
C31 C32 C34 N36 17.8(14) . . . . ?
C33 C32 C34 N36 -168.5(10) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_ls_R2B4CaCl
_database_code_depnum_ccdc_archive 'CCDC 2025076'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'CaCl2 (S)-2-(2-oxopyrrolidin-1-yl)butanamide pyridine-4-carboxamide'
_chemical_name_common            'CaCl2 Levetiracetam Isonicotinamide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H36 Ca N6 O6, 2(Cl)'
_chemical_formula_sum            'C22 H36 Ca Cl2 N6 O6'
_chemical_formula_weight         591.55

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.93030(11)
_cell_length_b                   15.1768(2)
_cell_length_c                   23.7226(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2855.17(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11133
_cell_measurement_theta_min      2.8070
_cell_measurement_theta_max      25.6360

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.453
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.2° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19720
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.818
_diffrn_reflns_theta_max         25.690
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5423
_reflns_number_gt                5133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;




_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)+(0.0348P)²+0.4850P] 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_abs_structure_details 
;
 Flack x determined using 2098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(19)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5423
_refine_ls_number_parameters     342
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Ca1 Ca 0.63439(5) 0.48358(3) 0.35405(2) 0.02409(12) Uani 1 1 d . . . . .
Cl2 Cl 0.34765(10) 0.39803(5) 0.50789(3) 0.04399(18) Uani 1 1 d . . . . .
Cl3 Cl 0.90567(10) 0.58016(6) 0.53125(3) 0.0467(2) Uani 1 1 d . . . . .
O4 O 0.6642(3) 0.47626(18) 0.45324(9) 0.0524(6) Uani 1 1 d D . . . .
H4A H 0.719(5) 0.505(3) 0.4753(16) 0.079 Uiso 1 1 d D U . . .
H4B H 0.583(4) 0.456(3) 0.4694(17) 0.079 Uiso 1 1 d D U . . .
O11 O -0.1657(2) 0.59527(13) 0.35965(8) 0.0407(5) Uani 1 1 d . . . . .
C12 C -0.1339(3) 0.66347(17) 0.38596(10) 0.0312(5) Uani 1 1 d . . . . .
C13 C -0.2556(4) 0.7192(2) 0.41832(15) 0.0494(8) Uani 1 1 d . . . . .
H13A H -0.3215 0.6834 0.4441 0.059 Uiso 1 1 calc R U . . .
H13B H -0.3316 0.7499 0.3930 0.059 Uiso 1 1 calc R U . . .
C14 C -0.1464(5) 0.7837(2) 0.45026(16) 0.0592(9) Uani 1 1 d . . . . .
H14A H -0.1928 0.8426 0.4477 0.071 Uiso 1 1 calc R U . . .
H14B H -0.1393 0.7671 0.4897 0.071 Uiso 1 1 calc R U . . .
C15 C 0.0253(4) 0.7802(2) 0.42321(16) 0.0517(8) Uani 1 1 d . . . . .
H15A H 0.0446 0.8317 0.3998 0.062 Uiso 1 1 calc R U . . .
H15B H 0.1134 0.7767 0.4515 0.062 Uiso 1 1 calc R U . . .
N16 N 0.0199(3) 0.69960(14) 0.38892(9) 0.0292(5) Uani 1 1 d . . . . .
C17 C 0.1634(3) 0.66634(16) 0.35713(11) 0.0292(5) Uani 1 1 d . . . . .
H17 H 0.1165 0.6336 0.3251 0.035 Uiso 1 1 calc R U . . .
C18 C 0.2715(3) 0.60107(17) 0.39003(11) 0.0295(5) Uani 1 1 d . . . . .
O19 O 0.4011(2) 0.57250(15) 0.36749(9) 0.0442(5) Uani 1 1 d . . . . .
N20 N 0.2218(3) 0.57642(17) 0.44044(10) 0.0398(6) Uani 1 1 d . . . . .
H20A H 0.2802 0.5388 0.4593 0.048 Uiso 1 1 calc R U . . .
H20B H 0.1308 0.5979 0.4546 0.048 Uiso 1 1 calc R U . . .
C21 C 0.2656(4) 0.7431(2) 0.33177(16) 0.0479(8) Uani 1 1 d . . . . .
H21A H 0.1873 0.7885 0.3198 0.058 Uiso 1 1 calc R U . . .
H21B H 0.3355 0.7681 0.3613 0.058 Uiso 1 1 calc R U . . .
C22 C 0.3777(5) 0.7201(3) 0.28233(18) 0.0737(12) Uani 1 1 d . . . . .
H22A H 0.4702 0.6845 0.2951 0.111 Uiso 1 1 calc R U . . .
H22B H 0.4205 0.7733 0.2657 0.111 Uiso 1 1 calc R U . . .
H22C H 0.3137 0.6880 0.2548 0.111 Uiso 1 1 calc R U . . .
O31 O 0.4541(2) 0.36494(13) 0.35327(9) 0.0398(5) Uani 1 1 d . . . . .
C32 C 0.4072(3) 0.29875(17) 0.37933(11) 0.0299(6) Uani 1 1 d . . . . .
C33 C 0.5144(4) 0.2373(2) 0.41306(15) 0.0497(8) Uani 1 1 d . . . . .
H33A H 0.5862 0.2696 0.4389 0.060 Uiso 1 1 calc R U . . .
H33B H 0.5845 0.2014 0.3887 0.060 Uiso 1 1 calc R U . . .
C34 C 0.3889(5) 0.1810(2) 0.44479(14) 0.0550(9) Uani 1 1 d . . . . .
H34A H 0.3748 0.2023 0.4830 0.066 Uiso 1 1 calc R U . . .
H34B H 0.4263 0.1202 0.4461 0.066 Uiso 1 1 calc R U . . .
C35 C 0.2255(4) 0.18873(19) 0.41224(14) 0.0455(7) Uani 1 1 d . . . . .
H35A H 0.2095 0.1386 0.3875 0.055 Uiso 1 1 calc R U . . .
H35B H 0.1297 0.1932 0.4375 0.055 Uiso 1 1 calc R U . . .
N36 N 0.2480(3) 0.27027(14) 0.37986(10) 0.0278(5) Uani 1 1 d . . . . .
C37 C 0.1188(3) 0.30861(17) 0.34412(11) 0.0299(5) Uani 1 1 d . . . . .
H37 H 0.1776 0.3495 0.3189 0.036 Uiso 1 1 calc R U . . .
C38 C -0.0111(3) 0.36334(18) 0.37532(11) 0.0301(6) Uani 1 1 d . . . . .
O39 O -0.1391(2) 0.38722(14) 0.34942(9) 0.0420(5) Uani 1 1 d . . . . .
N40 N 0.0192(3) 0.38563(18) 0.42785(10) 0.0446(6) Uani 1 1 d . . . . .
H40A H -0.0512 0.4182 0.4458 0.054 Uiso 1 1 calc R U . . .
H40B H 0.1096 0.3676 0.4442 0.054 Uiso 1 1 calc R U . . .
C41 C 0.0358(4) 0.2400(2) 0.30610(15) 0.0520(9) Uani 1 1 d . . . . .
H41A H -0.0131 0.1938 0.3292 0.062 Uiso 1 1 calc R U . . .
H41B H -0.0545 0.2675 0.2848 0.062 Uiso 1 1 calc R U . . .
C42 C 0.1632(6) 0.1997(3) 0.26539(17) 0.0780(13) Uani 1 1 d . . . . .
H42A H 0.2012 0.2440 0.2394 0.117 Uiso 1 1 calc R U . . .
H42B H 0.1109 0.1525 0.2449 0.117 Uiso 1 1 calc R U . . .
H42C H 0.2577 0.1773 0.2862 0.117 Uiso 1 1 calc R U . . .
C51 C 0.2551(3) 0.4789(2) 0.24147(12) 0.0409(7) Uani 1 1 d . . . . .
H51 H 0.2966 0.4739 0.2780 0.049 Uiso 1 1 calc R U . . .
C52 C 0.0835(4) 0.4787(3) 0.23159(12) 0.0471(8) Uani 1 1 d . . . . .
H52 H 0.0110 0.4734 0.2622 0.057 Uiso 1 1 calc R U . . .
N53 N 0.0168(3) 0.48583(19) 0.18022(10) 0.0423(6) Uani 1 1 d . . . . .
C54 C 0.1227(3) 0.4957(2) 0.13756(11) 0.0416(7) Uani 1 1 d . . . . .
H54 H 0.0776 0.5025 0.1016 0.050 Uiso 1 1 calc R U . . .
C55 C 0.2960(3) 0.4965(2) 0.14312(11) 0.0365(6) Uani 1 1 d . . . . .
H55 H 0.3651 0.5037 0.1118 0.044 Uiso 1 1 calc R U . . .
C56 C 0.3646(3) 0.48650(17) 0.19634(10) 0.0273(5) Uani 1 1 d . . . . .
C57 C 0.5516(3) 0.48584(17) 0.20765(10) 0.0266(5) Uani 1 1 d . . . . .
O58 O 0.6046(2) 0.49358(14) 0.25667(7) 0.0367(4) Uani 1 1 d . . . . .
N59 N 0.6529(3) 0.47706(17) 0.16435(9) 0.0355(5) Uani 1 1 d . . . . .
H59A H 0.7603 0.4765 0.1693 0.043 Uiso 1 1 calc R U . . .
H59B H 0.6120 0.4719 0.1309 0.043 Uiso 1 1 calc R U . . .


_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 O31 2.2991(19) . ?
Ca1 O19 2.3121(19) . ?
Ca1 O39 2.3187(18) 1_655 ?
Ca1 O11 2.3249(19) 1_655 ?
Ca1 O58 2.3272(17) . ?
Ca1 O4 2.367(2) . ?
O4 H4A 0.81(3) . ?
O4 H4B 0.81(3) . ?
O11 C12 1.235(3) . ?
O11 Ca1 2.3249(19) 1_455 ?
C12 N16 1.339(3) . ?
C12 C13 1.495(4) . ?
C13 C14 1.511(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.506(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N16 1.470(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N16 C17 1.456(3) . ?
C17 C18 1.525(4) . ?
C17 C21 1.542(4) . ?
C17 H17 0.9800 . ?
C18 O19 1.237(3) . ?
C18 N20 1.313(3) . ?
N20 H20A 0.8600 . ?
N20 H20B 0.8600 . ?
C21 C22 1.513(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O31 C32 1.237(3) . ?
C32 N36 1.335(3) . ?
C32 C33 1.494(4) . ?
C33 C34 1.513(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.513(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 N36 1.467(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
N36 C37 1.451(3) . ?
C37 C38 1.516(4) . ?
C37 C41 1.527(4) . ?
C37 H37 0.9800 . ?
C38 O39 1.241(3) . ?
C38 N40 1.314(4) . ?
O39 Ca1 2.3187(18) 1_455 ?
N40 H40A 0.8600 . ?
N40 H40B 0.8600 . ?
C41 C42 1.526(5) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C51 C52 1.381(4) . ?
C51 C56 1.383(4) . ?
C51 H51 0.9300 . ?
C52 N53 1.333(4) . ?
C52 H52 0.9300 . ?
N53 C54 1.323(4) . ?
C54 C55 1.381(4) . ?
C54 H54 0.9300 . ?
C55 C56 1.383(3) . ?
C55 H55 0.9300 . ?
C56 C57 1.507(3) . ?
C57 O58 1.242(3) . ?
C57 N59 1.311(3) . ?
N59 H59A 0.8600 . ?
N59 H59B 0.8600 . ?

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
O31 Ca1 O19 87.75(8) . . ?
O31 Ca1 O39 89.27(7) . 1_655 ?
O19 Ca1 O39 173.97(8) . 1_655 ?
O31 Ca1 O11 174.57(8) . 1_655 ?
O19 Ca1 O11 96.45(8) . 1_655 ?
O39 Ca1 O11 86.23(7) 1_655 1_655 ?
O31 Ca1 O58 88.85(7) . . ?
O19 Ca1 O58 91.01(7) . . ?
O39 Ca1 O58 94.17(7) 1_655 . ?
O11 Ca1 O58 94.50(7) 1_655 . ?
O31 Ca1 O4 91.91(8) . . ?
O19 Ca1 O4 88.30(8) . . ?
O39 Ca1 O4 86.57(8) 1_655 . ?
O11 Ca1 O4 84.79(8) 1_655 . ?
O58 Ca1 O4 178.95(9) . . ?
Ca1 O4 H4A 132(3) . . ?
Ca1 O4 H4B 114(3) . . ?
H4A O4 H4B 109(4) . . ?
C12 O11 Ca1 141.18(18) . 1_455 ?
O11 C12 N16 123.7(2) . . ?
O11 C12 C13 127.0(3) . . ?
N16 C12 C13 109.2(2) . . ?
C12 C13 C14 104.7(2) . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
C14 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
C15 C14 C13 106.4(3) . . ?
C15 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.6 . . ?
N16 C15 C14 103.8(3) . . ?
N16 C15 H15A 111.0 . . ?
C14 C15 H15A 111.0 . . ?
N16 C15 H15B 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C12 N16 C17 122.9(2) . . ?
C12 N16 C15 113.4(2) . . ?
C17 N16 C15 123.5(2) . . ?
N16 C17 C18 113.6(2) . . ?
N16 C17 C21 110.6(2) . . ?
C18 C17 C21 113.3(2) . . ?
N16 C17 H17 106.3 . . ?
C18 C17 H17 106.3 . . ?
C21 C17 H17 106.3 . . ?
O19 C18 N20 122.9(3) . . ?
O19 C18 C17 118.3(2) . . ?
N20 C18 C17 118.8(2) . . ?
C18 O19 Ca1 158.28(19) . . ?
C18 N20 H20A 120.0 . . ?
C18 N20 H20B 120.0 . . ?
H20A N20 H20B 120.0 . . ?
C22 C21 C17 115.9(3) . . ?
C22 C21 H21A 108.3 . . ?
C17 C21 H21A 108.3 . . ?
C22 C21 H21B 108.3 . . ?
C17 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C32 O31 Ca1 145.00(18) . . ?
O31 C32 N36 123.5(2) . . ?
O31 C32 C33 127.1(2) . . ?
N36 C32 C33 109.3(2) . . ?
C32 C33 C34 104.2(3) . . ?
C32 C33 H33A 110.9 . . ?
C34 C33 H33A 110.9 . . ?
C32 C33 H33B 110.9 . . ?
C34 C33 H33B 110.9 . . ?
H33A C33 H33B 108.9 . . ?
C33 C34 C35 105.4(2) . . ?
C33 C34 H34A 110.7 . . ?
C35 C34 H34A 110.7 . . ?
C33 C34 H34B 110.7 . . ?
C35 C34 H34B 110.7 . . ?
H34A C34 H34B 108.8 . . ?
N36 C35 C34 103.2(2) . . ?
N36 C35 H35A 111.1 . . ?
C34 C35 H35A 111.1 . . ?
N36 C35 H35B 111.1 . . ?
C34 C35 H35B 111.1 . . ?
H35A C35 H35B 109.1 . . ?
C32 N36 C37 122.2(2) . . ?
C32 N36 C35 113.1(2) . . ?
C37 N36 C35 123.9(2) . . ?
N36 C37 C38 114.5(2) . . ?
N36 C37 C41 112.1(2) . . ?
C38 C37 C41 111.6(2) . . ?
N36 C37 H37 106.0 . . ?
C38 C37 H37 106.0 . . ?
C41 C37 H37 106.0 . . ?
O39 C38 N40 123.0(3) . . ?
O39 C38 C37 118.3(2) . . ?
N40 C38 C37 118.6(2) . . ?
C38 O39 Ca1 142.61(19) . 1_455 ?
C38 N40 H40A 120.0 . . ?
C38 N40 H40B 120.0 . . ?
H40A N40 H40B 120.0 . . ?
C42 C41 C37 111.2(3) . . ?
C42 C41 H41A 109.4 . . ?
C37 C41 H41A 109.4 . . ?
C42 C41 H41B 109.4 . . ?
C37 C41 H41B 109.4 . . ?
H41A C41 H41B 108.0 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C52 C51 C56 119.2(2) . . ?
C52 C51 H51 120.4 . . ?
C56 C51 H51 120.4 . . ?
N53 C52 C51 123.1(3) . . ?
N53 C52 H52 118.5 . . ?
C51 C52 H52 118.5 . . ?
C54 N53 C52 117.2(2) . . ?
N53 C54 C55 124.0(2) . . ?
N53 C54 H54 118.0 . . ?
C55 C54 H54 118.0 . . ?
C54 C55 C56 118.5(2) . . ?
C54 C55 H55 120.7 . . ?
C56 C55 H55 120.7 . . ?
C51 C56 C55 117.9(2) . . ?
C51 C56 C57 118.6(2) . . ?
C55 C56 C57 123.4(2) . . ?
O58 C57 N59 122.4(2) . . ?
O58 C57 C56 119.9(2) . . ?
N59 C57 C56 117.7(2) . . ?
C57 O58 Ca1 163.25(17) . . ?
C57 N59 H59A 120.0 . . ?
C57 N59 H59B 120.0 . . ?
H59A N59 H59B 120.0 . . ?

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 O11 C12 N16 160.0(2) 1_455 . . . ?
Ca1 O11 C12 C13 -20.8(5) 1_455 . . . ?
O11 C12 C13 C14 170.1(3) . . . . ?
N16 C12 C13 C14 -10.7(4) . . . . ?
C12 C13 C14 C15 15.6(4) . . . . ?
C13 C14 C15 N16 -14.8(4) . . . . ?
O11 C12 N16 C17 5.7(4) . . . . ?
C13 C12 N16 C17 -173.6(2) . . . . ?
O11 C12 N16 C15 -179.5(3) . . . . ?
C13 C12 N16 C15 1.2(3) . . . . ?
C14 C15 N16 C12 8.7(4) . . . . ?
C14 C15 N16 C17 -176.5(3) . . . . ?
C12 N16 C17 C18 -94.2(3) . . . . ?
C15 N16 C17 C18 91.5(3) . . . . ?
C12 N16 C17 C21 137.2(3) . . . . ?
C15 N16 C17 C21 -37.1(4) . . . . ?
N16 C17 C18 O19 -176.5(2) . . . . ?
C21 C17 C18 O19 -49.3(3) . . . . ?
N16 C17 C18 N20 4.7(3) . . . . ?
C21 C17 C18 N20 131.9(3) . . . . ?
N20 C18 O19 Ca1 11.0(7) . . . . ?
C17 C18 O19 Ca1 -167.8(4) . . . . ?
N16 C17 C21 C22 -159.3(3) . . . . ?
C18 C17 C21 C22 71.9(4) . . . . ?
Ca1 O31 C32 N36 144.5(2) . . . . ?
Ca1 O31 C32 C33 -37.4(5) . . . . ?
O31 C32 C33 C34 168.6(3) . . . . ?
N36 C32 C33 C34 -13.0(3) . . . . ?
C32 C33 C34 C35 20.7(4) . . . . ?
C33 C34 C35 N36 -20.7(3) . . . . ?
O31 C32 N36 C37 7.7(4) . . . . ?
C33 C32 N36 C37 -170.7(2) . . . . ?
O31 C32 N36 C35 178.0(3) . . . . ?
C33 C32 N36 C35 -0.4(3) . . . . ?
C34 C35 N36 C32 13.6(3) . . . . ?
C34 C35 N36 C37 -176.3(3) . . . . ?
C32 N36 C37 C38 -108.9(3) . . . . ?
C35 N36 C37 C38 81.8(3) . . . . ?
C32 N36 C37 C41 122.6(3) . . . . ?
C35 N36 C37 C41 -46.6(4) . . . . ?
N36 C37 C38 O39 -169.3(2) . . . . ?
C41 C37 C38 O39 -40.6(3) . . . . ?
N36 C37 C38 N40 12.8(3) . . . . ?
C41 C37 C38 N40 141.5(3) . . . . ?
N40 C38 O39 Ca1 12.0(5) . . . 1_455 ?
C37 C38 O39 Ca1 -165.7(2) . . . 1_455 ?
N36 C37 C41 C42 -62.8(4) . . . . ?
C38 C37 C41 C42 167.2(3) . . . . ?
C56 C51 C52 N53 -0.2(6) . . . . ?
C51 C52 N53 C54 -1.8(5) . . . . ?
C52 N53 C54 C55 1.8(5) . . . . ?
N53 C54 C55 C56 0.0(5) . . . . ?
C52 C51 C56 C55 2.0(5) . . . . ?
C52 C51 C56 C57 -179.5(3) . . . . ?
C54 C55 C56 C51 -2.0(4) . . . . ?
C54 C55 C56 C57 179.7(3) . . . . ?
C51 C56 C57 O58 -12.2(4) . . . . ?
C55 C56 C57 O58 166.2(3) . . . . ?
C51 C56 C57 N59 167.9(3) . . . . ?
C55 C56 C57 N59 -13.7(4) . . . . ?
N59 C57 O58 Ca1 -143.6(5) . . . . ?
C56 C57 O58 Ca1 36.5(8) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
