# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_rgst20140902_0m
_database_code_depnum_ccdc_archive 'CCDC 1042338'
_audit_update_record             
;
2015-01-07 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;
_audit_creation_date             2014-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 Zr'
_chemical_formula_sum            'C24 H24 Zr'
_chemical_formula_weight         403.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   8.3971(3)
_cell_length_b                   12.4057(4)
_cell_length_c                   17.9270(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1867.49(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.57
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0405 before and 0.0353 after correction.
The Ratio of minimum to maximum transmission is 0.9207.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.172
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0075
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            39344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.929
_diffrn_ambient_temperature      100.11
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2024
_reflns_number_total             2255
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0187
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+1.4561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0493
_refine_ls_wR_factor_ref         0.0521
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C6(H6), C12(H12), C3(H3), C10(H10), C9(H9), C11(H11), C7(H7)
2.b Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zr1 Zr 0.0000 0.47928(2) 0.2500 0.00966(6) Uani 1 2 d S T P . .
C2 C 0.02861(15) 0.68914(11) 0.15596(7) 0.0147(2) Uani 1 1 d . . . . .
H2 H -0.0648 0.6988 0.1851 0.018 Uiso 1 1 calc R . . . .
C1 C 0.11700(14) 0.59422(10) 0.16539(7) 0.0136(2) Uani 1 1 d . . . . .
C8 C 0.28453(15) 0.41650(12) 0.26416(7) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.3560 0.4265 0.2237 0.023 Uiso 1 1 calc R . . . .
C6 C 0.29465(16) 0.66512(11) 0.06877(7) 0.0198(3) Uani 1 1 d . . . . .
H6 H 0.3864 0.6551 0.0385 0.024 Uiso 1 1 calc R . . . .
C12 C 0.18661(16) 0.32664(11) 0.27557(8) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.1799 0.2650 0.2442 0.024 Uiso 1 1 calc R . . . .
C4 C 0.20504(16) 0.75884(10) 0.06073(7) 0.0166(2) Uani 1 1 d . . . . .
C3 C 0.07138(15) 0.77007(10) 0.10584(7) 0.0157(2) Uani 1 1 d . . . . .
H3 H 0.0085 0.8336 0.1025 0.019 Uiso 1 1 calc R . . . .
C5 C 0.25073(19) 0.84345(11) 0.00430(7) 0.0224(3) Uani 1 1 d . . . . .
H5A H 0.2462 0.8124 -0.0459 0.034 Uiso 1 1 calc GR . . . .
H5B H 0.3591 0.8687 0.0145 0.034 Uiso 1 1 calc GR . . . .
H5C H 0.1765 0.9042 0.0076 0.034 Uiso 1 1 calc GR . . . .
C10 C 0.14606(16) 0.44415(11) 0.37192(7) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.1081 0.4754 0.4169 0.023 Uiso 1 1 calc R . . . .
C9 C 0.25881(16) 0.48979(11) 0.32326(8) 0.0194(3) Uani 1 1 d . . . . .
H9 H 0.3089 0.5579 0.3291 0.023 Uiso 1 1 calc R . . . .
C11 C 0.09926(16) 0.34388(11) 0.34215(8) 0.0195(3) Uani 1 1 d . . . . .
H11 H 0.0227 0.2963 0.3630 0.023 Uiso 1 1 calc R . . . .
C7 C 0.25286(16) 0.58581(10) 0.12008(7) 0.0179(2) Uani 1 1 d . . . . .
H7 H 0.3186 0.5238 0.1246 0.021 Uiso 1 1 calc R . . . .


_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 C1 2.3020(12) . ?
Zr1 C1 2.3020(12) 4 ?
Zr1 C8 2.5257(13) 4 ?
Zr1 C8 2.5257(13) . ?
Zr1 C12 2.5003(13) . ?
Zr1 C12 2.5003(13) 4 ?
Zr1 C10 2.5439(12) . ?
Zr1 C10 2.5439(12) 4 ?
Zr1 C9 2.5426(13) 4 ?
Zr1 C9 2.5426(13) . ?
Zr1 C11 2.4991(13) . ?
Zr1 C11 2.4990(13) 4 ?
C2 H2 0.9500 . ?
C2 C1 1.4022(17) . ?
C2 C3 1.3944(18) . ?
C1 C7 1.4044(17) . ?
C8 H8 0.9500 . ?
C8 C12 1.400(2) . ?
C8 C9 1.413(2) . ?
C6 H6 0.9500 . ?
C6 C4 1.3924(19) . ?
C6 C7 1.3920(18) . ?
C12 H12 0.9500 . ?
C12 C11 1.417(2) . ?
C4 C3 1.3903(18) . ?
C4 C5 1.5074(17) . ?
C3 H3 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C9 1.4064(19) . ?
C10 C11 1.4095(19) . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C7 H7 0.9500 . ?

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
C1 Zr1 C1 103.45(6) . 4 ?
C1 Zr1 C8 121.90(4) . 4 ?
C1 Zr1 C8 81.58(4) 4 4 ?
C1 Zr1 C8 81.58(4) . . ?
C1 Zr1 C8 121.90(4) 4 . ?
C1 Zr1 C12 108.81(5) . . ?
C1 Zr1 C12 108.82(5) 4 4 ?
C1 Zr1 C12 128.01(4) 4 . ?
C1 Zr1 C12 128.01(4) . 4 ?
C1 Zr1 C10 117.81(4) 4 4 ?
C1 Zr1 C10 75.27(4) 4 . ?
C1 Zr1 C10 75.27(4) . 4 ?
C1 Zr1 C10 117.81(4) . . ?
C1 Zr1 C9 89.58(4) 4 . ?
C1 Zr1 C9 89.58(4) . 4 ?
C1 Zr1 C9 86.78(4) . . ?
C1 Zr1 C9 86.78(4) 4 4 ?
C1 Zr1 C11 135.20(5) 4 4 ?
C1 Zr1 C11 97.07(4) . 4 ?
C1 Zr1 C11 97.07(5) 4 . ?
C1 Zr1 C11 135.20(4) . . ?
C8 Zr1 C8 144.08(7) 4 . ?
C8 Zr1 C10 53.47(4) . . ?
C8 Zr1 C10 119.32(4) . 4 ?
C8 Zr1 C10 53.47(4) 4 4 ?
C8 Zr1 C10 119.32(4) 4 . ?
C8 Zr1 C9 32.37(4) . . ?
C8 Zr1 C9 151.20(4) . 4 ?
C8 Zr1 C9 151.20(4) 4 . ?
C8 Zr1 C9 32.37(4) 4 4 ?
C12 Zr1 C8 112.19(5) . 4 ?
C12 Zr1 C8 32.35(5) 4 4 ?
C12 Zr1 C8 112.19(5) 4 . ?
C12 Zr1 C8 32.35(5) . . ?
C12 Zr1 C12 81.53(7) . 4 ?
C12 Zr1 C10 109.27(5) 4 . ?
C12 Zr1 C10 109.27(5) . 4 ?
C12 Zr1 C10 53.88(4) . . ?
C12 Zr1 C10 53.88(4) 4 4 ?
C12 Zr1 C9 53.74(4) 4 4 ?
C12 Zr1 C9 53.73(4) . . ?
C12 Zr1 C9 132.01(4) 4 . ?
C12 Zr1 C9 132.01(5) . 4 ?
C10 Zr1 C10 160.27(6) 4 . ?
C9 Zr1 C10 149.85(4) . 4 ?
C9 Zr1 C10 32.10(4) 4 4 ?
C9 Zr1 C10 149.84(4) 4 . ?
C9 Zr1 C10 32.10(4) . . ?
C9 Zr1 C9 174.12(6) 4 . ?
C11 Zr1 C8 53.90(4) . . ?
C11 Zr1 C8 100.06(5) 4 . ?
C11 Zr1 C8 53.90(4) 4 4 ?
C11 Zr1 C8 100.06(5) . 4 ?
C11 Zr1 C12 79.70(5) . 4 ?
C11 Zr1 C12 32.93(5) 4 4 ?
C11 Zr1 C12 32.94(5) . . ?
C11 Zr1 C12 79.70(4) 4 . ?
C11 Zr1 C10 32.45(4) 4 4 ?
C11 Zr1 C10 32.45(4) . . ?
C11 Zr1 C10 127.85(5) . 4 ?
C11 Zr1 C10 127.85(5) 4 . ?
C11 Zr1 C9 53.70(4) 4 4 ?
C11 Zr1 C9 131.38(5) 4 . ?
C11 Zr1 C9 131.38(5) . 4 ?
C11 Zr1 C9 53.70(4) . . ?
C11 Zr1 C11 95.53(7) 4 . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C3 C2 C1 123.09(12) . . ?
C2 C1 Zr1 111.95(8) . . ?
C2 C1 C7 115.00(11) . . ?
C7 C1 Zr1 132.98(9) . . ?
Zr1 C8 H8 118.7 . . ?
C12 C8 Zr1 72.82(7) . . ?
C12 C8 H8 125.9 . . ?
C12 C8 C9 108.25(12) . . ?
C9 C8 Zr1 74.47(7) . . ?
C9 C8 H8 125.9 . . ?
C4 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C4 121.49(12) . . ?
Zr1 C12 H12 117.6 . . ?
C8 C12 Zr1 74.83(8) . . ?
C8 C12 H12 126.1 . . ?
C8 C12 C11 107.86(12) . . ?
C11 C12 Zr1 73.49(7) . . ?
C11 C12 H12 126.1 . . ?
C6 C4 C5 120.88(12) . . ?
C3 C4 C6 117.37(12) . . ?
C3 C4 C5 121.74(12) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.70(12) . . ?
C4 C3 H3 119.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Zr1 C10 H10 119.9 . . ?
C9 C10 Zr1 73.90(7) . . ?
C9 C10 H10 126.0 . . ?
C9 C10 C11 107.95(12) . . ?
C11 C10 Zr1 72.03(7) . . ?
C11 C10 H10 126.0 . . ?
Zr1 C9 H9 118.7 . . ?
C8 C9 Zr1 73.16(7) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 Zr1 74.00(7) . . ?
C10 C9 C8 108.00(12) . . ?
C10 C9 H9 126.0 . . ?
Zr1 C11 H11 116.9 . . ?
C12 C11 Zr1 73.58(7) . . ?
C12 C11 H11 126.0 . . ?
C10 C11 Zr1 75.53(7) . . ?
C10 C11 C12 107.93(12) . . ?
C10 C11 H11 126.0 . . ?
C1 C7 H7 118.8 . . ?
C6 C7 C1 122.31(12) . . ?
C6 C7 H7 118.8 . . ?

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
Zr1 C1 C7 C6 175.64(10) . . . . ?
Zr1 C8 C12 C11 -66.62(9) . . . . ?
Zr1 C8 C9 C10 66.35(9) . . . . ?
Zr1 C12 C11 C10 -68.34(9) . . . . ?
Zr1 C10 C9 C8 -65.79(9) . . . . ?
Zr1 C10 C11 C12 67.02(9) . . . . ?
C2 C1 C7 C6 -1.09(19) . . . . ?
C1 C2 C3 C4 1.43(19) . . . . ?
C8 C12 C11 Zr1 67.52(9) . . . . ?
C8 C12 C11 C10 -0.82(15) . . . . ?
C6 C4 C3 C2 -1.10(19) . . . . ?
C12 C8 C9 Zr1 -65.52(9) . . . . ?
C12 C8 C9 C10 0.83(15) . . . . ?
C4 C6 C7 C1 1.4(2) . . . . ?
C3 C2 C1 Zr1 -177.73(10) . . . . ?
C3 C2 C1 C7 -0.31(18) . . . . ?
C5 C4 C3 C2 177.92(12) . . . . ?
C9 C8 C12 Zr1 66.61(9) . . . . ?
C9 C8 C12 C11 0.00(15) . . . . ?
C9 C10 C11 Zr1 -65.70(9) . . . . ?
C9 C10 C11 C12 1.33(14) . . . . ?
C11 C10 C9 Zr1 64.46(9) . . . . ?
C11 C10 C9 C8 -1.33(15) . . . . ?
C7 C6 C4 C3 -0.3(2) . . . . ?
C7 C6 C4 C5 -179.30(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
