 
data_37
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C33 H35 Cl N4 O8 Zr' 
_chemical_formula_sum 
 'C33 H35 Cl N4 O8 Zr' 
_chemical_formula_weight          742.32 
  
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' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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' 
 'Zr'  'Zr'  -2.9673   0.5597 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            15 
_space_group_name_H-M_alt         'I 2/a' 
_space_group_name_Hall            '-I 2ya' 
  
_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' 
 'x+1/2, y+1/2, z+1/2' 
 '-x+1, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y, z' 
 '-x+1/2, -y+1/2, -z+1/2' 
 'x, -y+1/2, z+1/2' 
  
_cell_length_a                    14.0287(2) 
_cell_length_b                    9.49643(13) 
_cell_length_c                    24.8679(3) 
_cell_angle_alpha                 90 
_cell_angle_beta                  92.3238(13) 
_cell_angle_gamma                 90 
_cell_volume                      3310.24(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     21534 
_cell_measurement_theta_min       2.9810 
_cell_measurement_theta_max       28.2430 
  
_exptl_crystal_description        'tabular needles' 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.489 
_exptl_crystal_F_000              1528 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.574 
_exptl_crystal_size_mid           0.168 
_exptl_crystal_size_min           0.104 
_exptl_absorpt_coefficient_mu     0.470 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.820 
_exptl_absorpt_correction_T_max   0.956 
_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             61094 
_diffrn_reflns_av_unetI/netI      0.0153 
_diffrn_reflns_av_R_equivalents   0.0331 
_diffrn_reflns_limit_h_min        -18 
_diffrn_reflns_limit_h_max        18 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -31 
_diffrn_reflns_limit_l_max        33 
_diffrn_reflns_theta_min          2.906 
_diffrn_reflns_theta_max          28.325 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.946 
_diffrn_measured_fraction_theta_full  0.999 
_diffrn_reflns_Laue_measured_fraction_max    0.946 
_diffrn_reflns_Laue_measured_fraction_full   0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.946 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              3917 
_reflns_number_gt                 3583 
_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)+(0.0219P)²+4.3362P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          3917 
_refine_ls_number_parameters      242 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0344 
_refine_ls_R_factor_gt            0.0292 
_refine_ls_wR_factor_ref          0.0707 
_refine_ls_wR_factor_gt           0.0682 
_refine_ls_goodness_of_fit_ref    1.161 
_refine_ls_restrained_S_all       1.161 
_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 
Zr1 Zr 0.250000 0.23457(2) 0.500000 0.02645(8) Uani 1 2 d S T P . . 
Cl1 Cl 0.3774(3) 0.1243(5) 0.4455(2) 0.0434(8) Uani 0.5 1 d . . P A -1 
N1 N 0.07524(12) 0.60095(18) 0.37153(7) 0.0398(4) Uani 1 1 d . . . . . 
N2 N 0.10611(11) 0.46278(16) 0.37189(6) 0.0330(3) Uani 1 1 d . . . . . 
C3 C 0.13126(12) 0.41756(18) 0.42191(7) 0.0285(3) Uani 1 1 d . . . . . 
O3 O 0.16267(9) 0.29175(12) 0.43224(5) 0.0307(3) Uani 1 1 d . . . . . 
C4 C 0.11486(12) 0.53135(19) 0.45625(7) 0.0301(4) Uani 1 1 d . . . . . 
C5 C 0.08003(14) 0.6400(2) 0.42215(8) 0.0373(4) Uani 1 1 d . . . . . 
H5A H 0.062181 0.730692 0.434388 0.045 Uiso 1 1 calc R U . . . 
C6 C 0.11407(14) 0.3865(2) 0.32127(7) 0.0377(4) Uani 1 1 d . . . . . 
H6A H 0.059053 0.411191 0.296891 0.045 Uiso 1 1 calc R U . . . 
H6B H 0.111060 0.284132 0.328480 0.045 Uiso 1 1 calc R U . . . 
C7 C 0.20477(14) 0.4186(2) 0.29360(7) 0.0337(4) Uani 1 1 d . . . . . 
C8 C 0.20653(15) 0.5121(2) 0.25111(8) 0.0422(5) Uani 1 1 d . . . . . 
H8A H 0.149493 0.559602 0.239982 0.051 Uiso 1 1 calc R U . . . 
C9 C 0.28965(15) 0.5385(2) 0.22420(8) 0.0428(5) Uani 1 1 d . . . . . 
H9A H 0.289353 0.603144 0.195055 0.051 Uiso 1 1 calc R U . . . 
C10 C 0.37262(14) 0.4696(2) 0.24034(7) 0.0342(4) Uani 1 1 d . . . . . 
C11 C 0.37241(15) 0.3779(2) 0.28376(8) 0.0407(4) Uani 1 1 d . . . . . 
H11A H 0.429800 0.332389 0.295583 0.049 Uiso 1 1 calc R U . . . 
C12 C 0.28966(15) 0.3528(2) 0.30970(7) 0.0394(4) Uani 1 1 d . . . . . 
H12A H 0.290407 0.289214 0.339206 0.047 Uiso 1 1 calc R U . . . 
O13 O 0.45801(10) 0.48366(16) 0.21648(5) 0.0439(3) Uani 1 1 d . . . . . 
C14 C 0.46110(18) 0.5665(3) 0.16951(10) 0.0564(6) Uani 1 1 d . . . . . 
H14A H 0.418748 0.525652 0.141341 0.085 Uiso 1 1 calc R U . . . 
H14B H 0.526531 0.568860 0.157153 0.085 Uiso 1 1 calc R U . . . 
H14C H 0.440175 0.662469 0.177408 0.085 Uiso 1 1 calc R U . . . 
C15 C 0.13514(12) 0.52295(18) 0.51257(7) 0.0283(3) Uani 1 1 d . . . . . 
O15 O 0.17317(8) 0.41765(12) 0.53423(4) 0.0285(3) Uani 1 1 d . . . . . 
O16 O 0.11187(9) 0.63385(13) 0.54121(5) 0.0349(3) Uani 1 1 d . . . . . 
C17 C 0.13314(16) 0.6252(2) 0.59921(7) 0.0392(4) Uani 1 1 d . . . . . 
H17A H 0.202508 0.612697 0.606536 0.047 Uiso 1 1 calc R U . . . 
H17B H 0.099260 0.544415 0.614808 0.047 Uiso 1 1 calc R U . . . 
C18 C 0.10014(19) 0.7603(2) 0.62311(9) 0.0513(6) Uani 1 1 d . . . . . 
H18A H 0.032720 0.775346 0.612874 0.077 Uiso 1 1 calc R U . . . 
H18B H 0.138129 0.838427 0.609724 0.077 Uiso 1 1 calc R U . . . 
H18C H 0.107939 0.755511 0.662411 0.077 Uiso 1 1 calc R U . . . 
C21 C 0.1057(3) 0.0899(5) 0.5105(2) 0.0500(11) Uani 0.5 1 d . . P A -1 
H21A H 0.047818 0.120924 0.493197 0.060 Uiso 0.5 1 calc R U P A -1 
C22 C 0.1388(12) 0.127(2) 0.5632(9) 0.049(4) Uani 0.5 1 d . . P A -1 
H22A H 0.108477 0.188141 0.587629 0.058 Uiso 0.5 1 calc R U P A -1 
C23 C 0.2260(3) 0.0559(4) 0.57178(17) 0.0426(9) Uani 0.5 1 d . . P A -1 
H23A H 0.265034 0.060686 0.603858 0.051 Uiso 0.5 1 calc R U P A -1 
C24 C 0.2468(4) -0.0224(4) 0.5267(2) 0.0523(12) Uani 0.5 1 d . . P A -1 
H24A H 0.301285 -0.080271 0.522637 0.063 Uiso 0.5 1 calc R U P A -1 
C25 C 0.1723(4) -0.0005(5) 0.48801(19) 0.0569(13) Uani 0.5 1 d . . P A -1 
H25A H 0.167880 -0.039998 0.452893 0.068 Uiso 0.5 1 calc R U P A -1 
  
  
_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 
Zr1 O3 2.1136(12) 2_556 ? 
Zr1 O3 2.1136(12) . ? 
Zr1 O15 2.2323(12) 2_556 ? 
Zr1 O15 2.2323(12) . ? 
Zr1 C21 2.469(4) . ? 
Zr1 C22 2.478(18) . ? 
Zr1 C23 2.495(4) . ? 
Zr1 C25 2.497(4) . ? 
Zr1 Cl1 2.514(4) . ? 
Zr1 C24 2.530(4) . ? 
N1 C5 1.312(2) . ? 
N1 N2 1.382(2) . ? 
N2 C3 1.349(2) . ? 
N2 C6 1.461(2) . ? 
C3 O3 1.296(2) . ? 
C3 C4 1.402(2) . ? 
C4 C5 1.411(2) . ? 
C4 C15 1.420(2) . ? 
C6 C7 1.502(3) . ? 
C7 C8 1.381(3) . ? 
C7 C12 1.389(3) . ? 
C8 C9 1.390(3) . ? 
C9 C10 1.381(3) . ? 
C10 O13 1.365(2) . ? 
C10 C11 1.387(3) . ? 
C11 C12 1.372(3) . ? 
O13 C14 1.410(3) . ? 
C15 O15 1.246(2) . ? 
C15 O16 1.320(2) . ? 
O16 C17 1.463(2) . ? 
C17 C18 1.495(3) . ? 
C21 C25 1.401(8) . ? 
C21 C22 1.42(2) . ? 
C22 C23 1.408(18) . ? 
C23 C24 1.387(6) . ? 
C24 C25 1.407(7) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
O3 Zr1 O3 150.23(7) 2_556 . ? 
O3 Zr1 O15 80.25(4) 2_556 2_556 ? 
O3 Zr1 O15 76.65(5) . 2_556 ? 
O3 Zr1 O15 76.65(5) 2_556 . ? 
O3 Zr1 O15 80.25(4) . . ? 
O15 Zr1 O15 77.69(6) 2_556 . ? 
O3 Zr1 C21 120.67(13) 2_556 . ? 
O3 Zr1 C21 77.05(12) . . ? 
O15 Zr1 C21 152.16(11) 2_556 . ? 
O15 Zr1 C21 89.01(14) . . ? 
O3 Zr1 C22 87.7(5) 2_556 . ? 
O3 Zr1 C22 104.6(5) . . ? 
O15 Zr1 C22 152.6(5) 2_556 . ? 
O15 Zr1 C22 75.6(5) . . ? 
C21 Zr1 C22 33.3(5) . . ? 
O3 Zr1 C23 72.24(10) 2_556 . ? 
O3 Zr1 C23 130.87(10) . . ? 
O15 Zr1 C23 152.06(10) 2_556 . ? 
O15 Zr1 C23 100.11(11) . . ? 
C21 Zr1 C23 53.93(14) . . ? 
C22 Zr1 C23 32.9(4) . . ? 
O3 Zr1 C25 124.13(12) 2_556 . ? 
O3 Zr1 C25 84.16(13) . . ? 
O15 Zr1 C25 150.00(11) 2_556 . ? 
O15 Zr1 C25 121.78(14) . . ? 
C21 Zr1 C25 32.77(18) . . ? 
C22 Zr1 C25 54.9(6) . . ? 
C23 Zr1 C25 53.61(15) . . ? 
O3 Zr1 Cl1 97.76(13) 2_556 . ? 
O3 Zr1 Cl1 94.53(14) . . ? 
O15 Zr1 Cl1 75.77(11) 2_556 . ? 
O15 Zr1 Cl1 153.44(11) . . ? 
C21 Zr1 Cl1 115.38(17) . . ? 
C22 Zr1 Cl1 130.6(4) . . ? 
C23 Zr1 Cl1 102.82(15) . . ? 
C25 Zr1 Cl1 83.09(16) . . ? 
O3 Zr1 C24 93.14(13) 2_556 . ? 
O3 Zr1 C24 116.16(13) . . ? 
O15 Zr1 C24 149.92(12) 2_556 . ? 
O15 Zr1 C24 129.59(11) . . ? 
C21 Zr1 C24 53.99(17) . . ? 
C22 Zr1 C24 54.5(5) . . ? 
C23 Zr1 C24 32.03(15) . . ? 
C25 Zr1 C24 32.49(17) . . ? 
Cl1 Zr1 C24 76.13(15) . . ? 
C5 N1 N2 105.00(15) . . ? 
C3 N2 N1 112.23(15) . . ? 
C3 N2 C6 127.63(16) . . ? 
N1 N2 C6 120.01(15) . . ? 
O3 C3 N2 123.40(16) . . ? 
O3 C3 C4 130.76(15) . . ? 
N2 C3 C4 105.84(15) . . ? 
C3 O3 Zr1 125.21(10) . . ? 
C3 C4 C5 105.03(15) . . ? 
C3 C4 C15 121.75(16) . . ? 
C5 C4 C15 133.20(17) . . ? 
N1 C5 C4 111.89(17) . . ? 
N2 C6 C7 112.96(15) . . ? 
C8 C7 C12 117.89(18) . . ? 
C8 C7 C6 121.51(18) . . ? 
C12 C7 C6 120.59(17) . . ? 
C7 C8 C9 121.69(19) . . ? 
C10 C9 C8 119.23(18) . . ? 
O13 C10 C9 124.86(17) . . ? 
O13 C10 C11 115.45(17) . . ? 
C9 C10 C11 119.69(18) . . ? 
C12 C11 C10 120.26(18) . . ? 
C11 C12 C7 121.20(17) . . ? 
C10 O13 C14 118.15(16) . . ? 
O15 C15 O16 121.21(15) . . ? 
O15 C15 C4 122.46(16) . . ? 
O16 C15 C4 116.32(15) . . ? 
C15 O15 Zr1 131.71(11) . . ? 
C15 O16 C17 116.25(14) . . ? 
O16 C17 C18 106.85(16) . . ? 
C25 C21 C22 108.9(8) . . ? 
C25 C21 Zr1 74.7(2) . . ? 
C22 C21 Zr1 73.7(8) . . ? 
C23 C22 C21 105.6(14) . . ? 
C23 C22 Zr1 74.2(7) . . ? 
C21 C22 Zr1 73.0(8) . . ? 
C24 C23 C22 110.3(11) . . ? 
C24 C23 Zr1 75.4(2) . . ? 
C22 C23 Zr1 72.9(8) . . ? 
C23 C24 C25 107.4(4) . . ? 
C23 C24 Zr1 72.6(2) . . ? 
C25 C24 Zr1 72.5(2) . . ? 
C21 C25 C24 107.9(4) . . ? 
C21 C25 Zr1 72.5(2) . . ? 
C24 C25 Zr1 75.0(2) . . ? 
  
_refine_diff_density_max    0.305 
_refine_diff_density_min   -0.367 
_refine_diff_density_rms    0.051 
  
  
  
#===END

