 
data_19
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C32 H42 Ca N4 O10' 
_chemical_formula_sum 
 'C32 H42 Ca N4 O10' 
_chemical_formula_weight          682.77 
  
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' 
  
_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                    8.3922(2) 
_cell_length_b                    10.6222(4) 
_cell_length_c                    11.4899(5) 
_cell_angle_alpha                 65.671(4) 
_cell_angle_beta                  89.753(3) 
_cell_angle_gamma                 69.888(3) 
_cell_volume                      865.01(6) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     4930 
_cell_measurement_theta_min       2.8360 
_cell_measurement_theta_max       27.1870 
  
_exptl_crystal_description        tablets 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.311 
_exptl_crystal_F_000              362 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.511 
_exptl_crystal_size_mid           0.157 
_exptl_crystal_size_min           0.064 
_exptl_absorpt_coefficient_mu     0.241 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.932 
_exptl_absorpt_correction_T_max   0.986 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             20138 
_diffrn_reflns_av_unetI/netI      0.0331 
_diffrn_reflns_av_R_equivalents   0.0384 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          2.619 
_diffrn_reflns_theta_max          28.317 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.901 
_diffrn_measured_fraction_theta_full  0.999 
_diffrn_reflns_Laue_measured_fraction_max    0.901 
_diffrn_reflns_Laue_measured_fraction_full   0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.901 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              3874 
_reflns_number_gt                 2972 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_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)+(0.0396P)²+0.3390P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          3874 
_refine_ls_number_parameters      221 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0631 
_refine_ls_R_factor_gt            0.0424 
_refine_ls_wR_factor_ref          0.1027 
_refine_ls_wR_factor_gt           0.0928 
_refine_ls_goodness_of_fit_ref    1.031 
_refine_ls_restrained_S_all       1.031 
_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 0.500000 0.500000 0.000000 0.02962(14) Uani 1 2 d S . P . . 
N1 N -0.10262(17) 0.53685(17) 0.19100(14) 0.0340(3) Uani 1 1 d . . . . . 
N2 N 0.05161(17) 0.42762(16) 0.19736(13) 0.0303(3) Uani 1 1 d . . . . . 
C3 C 0.1581(2) 0.48561(19) 0.12030(15) 0.0273(4) Uani 1 1 d . . . . . 
O3 O 0.30629(14) 0.40623(13) 0.11265(11) 0.0329(3) Uani 1 1 d . . . . . 
C4 C 0.0625(2) 0.64177(19) 0.05957(15) 0.0287(4) Uani 1 1 d . . . . . 
C5 C -0.0939(2) 0.6626(2) 0.10819(16) 0.0326(4) Uani 1 1 d . . . . . 
H5A H -0.183124 0.757313 0.083692 0.039 Uiso 1 1 calc R U . . . 
C6 C 0.0898(2) 0.27419(19) 0.28527(17) 0.0348(4) Uani 1 1 d . . . . . 
H6A H 0.165695 0.210266 0.248627 0.042 Uiso 1 1 calc R U . . . 
H6B H -0.018628 0.255864 0.292026 0.042 Uiso 1 1 calc R U . . . 
C7 C 0.1755(2) 0.22811(19) 0.41987(17) 0.0315(4) Uani 1 1 d . . . . . 
C8 C 0.1589(2) 0.33033(19) 0.46951(17) 0.0345(4) Uani 1 1 d . . . . . 
H8A H 0.092011 0.432804 0.417902 0.041 Uiso 1 1 calc R U . . . 
C9 C 0.2381(2) 0.2854(2) 0.59251(18) 0.0370(4) Uani 1 1 d . . . . . 
H9A H 0.224492 0.356739 0.625140 0.044 Uiso 1 1 calc R U . . . 
C10 C 0.3374(2) 0.1365(2) 0.66877(18) 0.0373(4) Uani 1 1 d . . . . . 
C11 C 0.3543(3) 0.0332(2) 0.62143(19) 0.0437(5) Uani 1 1 d . . . . . 
H11A H 0.420995 -0.069281 0.673036 0.052 Uiso 1 1 calc R U . . . 
C12 C 0.2730(3) 0.0804(2) 0.49813(19) 0.0413(5) Uani 1 1 d . . . . . 
H12A H 0.284712 0.008689 0.466275 0.050 Uiso 1 1 calc R U . . . 
O13 O 0.41266(17) 0.10256(16) 0.78905(13) 0.0511(4) Uani 1 1 d . . . . . 
C14 C 0.5266(3) -0.0483(3) 0.8655(2) 0.0721(8) Uani 1 1 d . . . . . 
H14A H 0.582587 -0.056055 0.944139 0.108 Uiso 1 1 calc R U . . . 
H14B H 0.614061 -0.078801 0.815464 0.108 Uiso 1 1 calc R U . . . 
H14C H 0.461080 -0.113505 0.889224 0.108 Uiso 1 1 calc R U . . . 
C15 C 0.1153(2) 0.75074(19) -0.03384(16) 0.0306(4) Uani 1 1 d . . . . . 
O15 O 0.25748(14) 0.72644(13) -0.06995(12) 0.0366(3) Uani 1 1 d . . . . . 
O16 O -0.00705(15) 0.88814(13) -0.08373(12) 0.0385(3) Uani 1 1 d . . . . . 
C17 C 0.0342(3) 1.0077(2) -0.1799(2) 0.0467(5) Uani 1 1 d . . . . . 
H17A H 0.087020 0.978089 -0.246447 0.056 Uiso 1 1 calc R U . . . 
H17B H 0.116562 1.031011 -0.138710 0.056 Uiso 1 1 calc R U . . . 
C18 C -0.1296(3) 1.1408(2) -0.2404(2) 0.0591(6) Uani 1 1 d . . . . . 
H18A H -0.104728 1.225736 -0.301819 0.089 Uiso 1 1 calc R U . . . 
H18B H -0.184567 1.165055 -0.172873 0.089 Uiso 1 1 calc R U . . . 
H18C H -0.206993 1.118731 -0.286036 0.089 Uiso 1 1 calc R U . . . 
O20 O 0.57953(15) 0.52421(15) 0.18140(12) 0.0411(3) Uani 1 1 d D . . . . 
H20 H 0.6869(3) 0.5216(8) 0.1924(15) 0.074(8) Uiso 1 1 d D . . . . 
C21 C 0.5108(2) 0.5036(2) 0.29864(19) 0.0433(5) Uani 1 1 d . . . . . 
H21A H 0.389991 0.513425 0.284333 0.052 Uiso 1 1 calc R U . . . 
H21B H 0.511321 0.582622 0.323009 0.052 Uiso 1 1 calc R U . . . 
C22 C 0.6100(4) 0.3560(3) 0.4061(2) 0.0758(8) Uani 1 1 d . . . . . 
H22A H 0.555675 0.344719 0.483534 0.114 Uiso 1 1 calc R U . . . 
H22B H 0.727884 0.348227 0.424289 0.114 Uiso 1 1 calc R U . . . 
H22C H 0.612164 0.277393 0.381572 0.114 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 O3 2.3116(11) . ? 
Ca1 O3 2.3117(11) 2_665 ? 
Ca1 O20 2.3296(12) 2_665 ? 
Ca1 O20 2.3297(12) . ? 
Ca1 O15 2.3724(11) 2_665 ? 
Ca1 O15 2.3724(11) . ? 
N1 C5 1.309(2) . ? 
N1 N2 1.3875(19) . ? 
N2 C3 1.372(2) . ? 
N2 C6 1.438(2) . ? 
C3 O3 1.2669(19) . ? 
C3 C4 1.420(2) . ? 
C4 C5 1.407(2) . ? 
C4 C15 1.419(2) . ? 
C6 C7 1.514(2) . ? 
C7 C12 1.378(3) . ? 
C7 C8 1.389(2) . ? 
C8 C9 1.379(2) . ? 
C9 C10 1.386(3) . ? 
C10 O13 1.371(2) . ? 
C10 C11 1.380(3) . ? 
C11 C12 1.382(3) . ? 
O13 C14 1.431(2) . ? 
C15 O15 1.2385(19) . ? 
C15 O16 1.341(2) . ? 
O16 C17 1.448(2) . ? 
C17 C18 1.494(3) . ? 
O20 C21 1.426(2) . ? 
C21 C22 1.480(3) . ? 
  
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 
O3 Ca1 O3 180.0 . 2_665 ? 
O3 Ca1 O20 92.72(4) . 2_665 ? 
O3 Ca1 O20 87.28(4) 2_665 2_665 ? 
O3 Ca1 O20 87.28(4) . . ? 
O3 Ca1 O20 92.72(4) 2_665 . ? 
O20 Ca1 O20 180.0 2_665 . ? 
O3 Ca1 O15 98.72(4) . 2_665 ? 
O3 Ca1 O15 81.28(4) 2_665 2_665 ? 
O20 Ca1 O15 90.86(4) 2_665 2_665 ? 
O20 Ca1 O15 89.14(4) . 2_665 ? 
O3 Ca1 O15 81.28(4) . . ? 
O3 Ca1 O15 98.72(4) 2_665 . ? 
O20 Ca1 O15 89.14(4) 2_665 . ? 
O20 Ca1 O15 90.86(4) . . ? 
O15 Ca1 O15 180.0 2_665 . ? 
C5 N1 N2 104.97(13) . . ? 
C3 N2 N1 112.60(13) . . ? 
C3 N2 C6 127.16(14) . . ? 
N1 N2 C6 120.09(13) . . ? 
O3 C3 N2 123.29(15) . . ? 
O3 C3 C4 132.40(15) . . ? 
N2 C3 C4 104.30(13) . . ? 
C3 O3 Ca1 124.46(10) . . ? 
C5 C4 C15 128.32(16) . . ? 
C5 C4 C3 105.67(15) . . ? 
C15 C4 C3 125.97(15) . . ? 
N1 C5 C4 112.44(15) . . ? 
N2 C6 C7 114.31(14) . . ? 
C12 C7 C8 117.66(17) . . ? 
C12 C7 C6 120.17(16) . . ? 
C8 C7 C6 122.18(16) . . ? 
C9 C8 C7 121.02(17) . . ? 
C8 C9 C10 120.29(17) . . ? 
O13 C10 C11 124.34(17) . . ? 
O13 C10 C9 116.18(16) . . ? 
C11 C10 C9 119.48(17) . . ? 
C10 C11 C12 119.33(18) . . ? 
C7 C12 C11 122.21(17) . . ? 
C10 O13 C14 117.12(16) . . ? 
O15 C15 O16 121.34(16) . . ? 
O15 C15 C4 125.50(16) . . ? 
O16 C15 C4 113.15(14) . . ? 
C15 O15 Ca1 129.63(11) . . ? 
C15 O16 C17 117.50(14) . . ? 
O16 C17 C18 107.58(17) . . ? 
C21 O20 Ca1 131.90(10) . . ? 
O20 C21 C22 112.14(17) . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag 
O20 H20 N1  0.9000(1) 1.828(3) 2.7215(18) 171.9(13) 1_655 yes 
  
_refine_diff_density_max    0.252 
_refine_diff_density_min   -0.237 
_refine_diff_density_rms    0.044 
  
  
  
#===END

