# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_20230822thc_4obncooh_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2349759'
loop_
_audit_author_name
_audit_author_address
'Tan Hao-Chong'
;Sourthern university of science and technology
China
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-10-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(1S,2S)-2-(4-(benzyloxy)phenyl)cyclopropane-1-carbonitrile
_chemical_formula_moiety         'C17 H15 N O'
_chemical_formula_sum            'C17 H15 N O'
_chemical_formula_weight         249.30
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.1916(8)
_cell_length_b                   7.5616(9)
_cell_length_c                   27.676(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1295.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9815
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      73.05
_cell_measurement_theta_min      5.28
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1489 before and 0.0920 after correction.
The Ratio of minimum to maximum transmission is 0.8433.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            25804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         73.265
_diffrn_reflns_theta_min         5.276
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON III area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   'microfocus Metaljet'
_diffrn_source_current           3.57
_diffrn_source_power             0.24947159999999996
_diffrn_source_type              'Incoatec Metaljet'
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3778
_reflns_number_total             3919
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1522 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3919
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.4121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1119
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C3(H3a,H3b)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C13(H13), C11(H11), C14(H14), C16(H16), C17(H17), C6(H6), C7(H7),
 C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19897(19) 0.53230(16) 0.75126(4) 0.0215(2) Uani 1 1 d . . . . .
N1 N 1.1607(3) 0.5770(2) 0.50965(6) 0.0323(4) Uani 1 1 d . . . . .
C18 C -0.2179(3) 0.5581(2) 0.90643(6) 0.0239(3) Uani 1 1 d . . . . .
H18 H -0.320900 0.580363 0.931140 0.029 Uiso 1 1 calc R U . . .
C13 C -0.2598(3) 0.6099(2) 0.85917(6) 0.0230(3) Uani 1 1 d . . . . .
H13 H -0.390036 0.670558 0.851807 0.028 Uiso 1 1 calc R U . . .
C11 C -0.1118(3) 0.5734(2) 0.82241(6) 0.0205(3) Uani 1 1 d . . . . .
H11 H -0.142765 0.607130 0.790084 0.025 Uiso 1 1 calc R U . . .
C15 C 0.0810(3) 0.4876(2) 0.83316(6) 0.0182(3) Uani 1 1 d . . . . .
C10 C 0.2479(3) 0.4432(2) 0.79534(6) 0.0214(3) Uani 1 1 d . . . . .
H10A H 0.392745 0.479319 0.806819 0.026 Uiso 1 1 calc R U . . .
H10B H 0.249858 0.313830 0.789771 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3485(3) 0.5135(2) 0.71476(6) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.2912(3) 0.5850(2) 0.67009(6) 0.0223(3) Uani 1 1 d . . . . .
H14 H 0.158665 0.647054 0.666572 0.027 Uiso 1 1 calc R U . . .
C16 C 0.4288(3) 0.5652(2) 0.63071(6) 0.0229(3) Uani 1 1 d . . . . .
H16 H 0.388262 0.612638 0.600249 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6271(3) 0.4760(2) 0.63532(6) 0.0211(3) Uani 1 1 d . . . . .
C4 C 0.7690(3) 0.4293(2) 0.59355(6) 0.0220(3) Uani 1 1 d . . . . .
H4 H 0.908775 0.372455 0.602836 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7818(3) 0.5449(2) 0.54845(6) 0.0233(3) Uani 1 1 d . . . . .
H2 H 0.683867 0.649931 0.547131 0.028 Uiso 1 1 calc R U . . .
C5 C 0.9927(3) 0.5640(3) 0.52656(6) 0.0269(4) Uani 1 1 d . . . . .
C17 C 0.5478(3) 0.4305(2) 0.72036(6) 0.0203(3) Uani 1 1 d . . . . .
H17 H 0.589773 0.385220 0.750965 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6854(3) 0.4145(2) 0.68067(6) 0.0212(3) Uani 1 1 d . . . . .
H6 H 0.822428 0.360107 0.684826 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6758(3) 0.3636(2) 0.54681(6) 0.0265(4) Uani 1 1 d . . . . .
H3A H 0.516556 0.358815 0.543905 0.032 Uiso 1 1 calc R U . . .
H3B H 0.753668 0.267574 0.529827 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1251(3) 0.4398(2) 0.88091(6) 0.0214(3) Uani 1 1 d . . . . .
H7 H 0.258284 0.383992 0.888529 0.026 Uiso 1 1 calc R U . . .
C1 C -0.0239(3) 0.4732(2) 0.91744(6) 0.0238(3) Uani 1 1 d . . . . .
H1 H 0.006316 0.438384 0.949721 0.029 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
O1 C10 1.4264(19) . ?
O1 C12 1.3774(18) . ?
N1 C5 1.145(3) . ?
C18 H18 0.9500 . ?
C18 C13 1.390(2) . ?
C18 C1 1.396(2) . ?
C13 H13 0.9500 . ?
C13 C11 1.397(2) . ?
C11 H11 0.9500 . ?
C11 C15 1.390(2) . ?
C15 C10 1.509(2) . ?
C15 C7 1.397(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C14 1.395(2) . ?
C12 C17 1.393(2) . ?
C14 H14 0.9500 . ?
C14 C16 1.392(2) . ?
C16 H16 0.9500 . ?
C16 C8 1.406(2) . ?
C8 C4 1.494(2) . ?
C8 C6 1.386(2) . ?
C4 H4 1.0000 . ?
C4 C2 1.526(2) . ?
C4 C3 1.501(2) . ?
C2 H2 1.0000 . ?
C2 C5 1.447(3) . ?
C2 C3 1.521(2) . ?
C17 H17 0.9500 . ?
C17 C6 1.395(2) . ?
C6 H6 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C1 1.392(2) . ?
C1 H1 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
C12 O1 C10 115.82(12) . . ?
C13 C18 H18 120.1 . . ?
C13 C18 C1 119.71(16) . . ?
C1 C18 H18 120.1 . . ?
C18 C13 H13 119.8 . . ?
C18 C13 C11 120.49(16) . . ?
C11 C13 H13 119.8 . . ?
C13 C11 H11 120.0 . . ?
C15 C11 C13 119.97(15) . . ?
C15 C11 H11 120.0 . . ?
C11 C15 C10 122.92(14) . . ?
C11 C15 C7 119.40(14) . . ?
C7 C15 C10 117.68(14) . . ?
O1 C10 C15 110.03(13) . . ?
O1 C10 H10A 109.7 . . ?
O1 C10 H10B 109.7 . . ?
C15 C10 H10A 109.7 . . ?
C15 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C12 C14 116.02(14) . . ?
O1 C12 C17 124.08(14) . . ?
C17 C12 C14 119.89(15) . . ?
C12 C14 H14 120.1 . . ?
C16 C14 C12 119.76(16) . . ?
C16 C14 H14 120.1 . . ?
C14 C16 H16 119.5 . . ?
C14 C16 C8 121.02(15) . . ?
C8 C16 H16 119.5 . . ?
C16 C8 C4 123.81(15) . . ?
C6 C8 C16 118.05(15) . . ?
C6 C8 C4 117.90(15) . . ?
C8 C4 H4 114.3 . . ?
C8 C4 C2 121.88(14) . . ?
C8 C4 C3 121.25(15) . . ?
C2 C4 H4 114.3 . . ?
C3 C4 H4 114.3 . . ?
C3 C4 C2 60.33(11) . . ?
C4 C2 H2 116.9 . . ?
C5 C2 C4 116.53(15) . . ?
C5 C2 H2 116.9 . . ?
C5 C2 C3 117.83(15) . . ?
C3 C2 C4 59.04(11) . . ?
C3 C2 H2 116.9 . . ?
N1 C5 C2 179.0(2) . . ?
C12 C17 H17 120.3 . . ?
C12 C17 C6 119.50(15) . . ?
C6 C17 H17 120.3 . . ?
C8 C6 C17 121.65(15) . . ?
C8 C6 H6 119.2 . . ?
C17 C6 H6 119.2 . . ?
C4 C3 C2 60.64(11) . . ?
C4 C3 H3A 117.7 . . ?
C4 C3 H3B 117.7 . . ?
C2 C3 H3A 117.7 . . ?
C2 C3 H3B 117.7 . . ?
H3A C3 H3B 114.8 . . ?
C15 C7 H7 119.7 . . ?
C1 C7 C15 120.70(15) . . ?
C1 C7 H7 119.7 . . ?
C18 C1 H1 120.1 . . ?
C7 C1 C18 119.70(15) . . ?
C7 C1 H1 120.1 . . ?

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
O1 C12 C14 C16 -177.25(14) . . . . ?
O1 C12 C17 C6 178.38(15) . . . . ?
C18 C13 C11 C15 -1.2(3) . . . . ?
C13 C18 C1 C7 -0.5(3) . . . . ?
C13 C11 C15 C10 179.73(16) . . . . ?
C13 C11 C15 C7 -0.5(2) . . . . ?
C11 C15 C10 O1 11.9(2) . . . . ?
C11 C15 C7 C1 1.6(2) . . . . ?
C15 C7 C1 C18 -1.1(3) . . . . ?
C10 O1 C12 C14 173.66(14) . . . . ?
C10 O1 C12 C17 -6.9(2) . . . . ?
C10 C15 C7 C1 -178.53(16) . . . . ?
C12 O1 C10 C15 175.26(13) . . . . ?
C12 C14 C16 C8 -0.9(3) . . . . ?
C12 C17 C6 C8 -1.3(2) . . . . ?
C14 C12 C17 C6 -2.2(2) . . . . ?
C14 C16 C8 C4 171.73(16) . . . . ?
C14 C16 C8 C6 -2.5(2) . . . . ?
C16 C8 C4 C2 32.2(2) . . . . ?
C16 C8 C4 C3 -40.1(2) . . . . ?
C16 C8 C6 C17 3.6(2) . . . . ?
C8 C4 C2 C5 141.59(17) . . . . ?
C8 C4 C2 C3 -110.41(18) . . . . ?
C8 C4 C3 C2 111.43(17) . . . . ?
C4 C8 C6 C17 -170.95(15) . . . . ?
C5 C2 C3 C4 105.80(17) . . . . ?
C17 C12 C14 C16 3.3(2) . . . . ?
C6 C8 C4 C2 -153.58(16) . . . . ?
C6 C8 C4 C3 134.15(17) . . . . ?
C3 C4 C2 C5 -108.00(17) . . . . ?
C7 C15 C10 O1 -167.97(14) . . . . ?
C1 C18 C13 C11 1.7(3) . . . . ?

_olex2_submission_original_sample_id 20230822thc_4OBnCN
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20231028thc_4no2cn_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2349760'
loop_
_audit_author_name
_audit_author_address
'Tan Hao-Chong'
;Sourthern university of science and technology
China
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-10-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(1S,2S)-2-(4-nitrophenyl)cyclopropane-1-carbonitrile
_chemical_formula_moiety         '2(C10 H8 N2 O2)'
_chemical_formula_sum            'C20 H16 N4 O4'
_chemical_formula_weight         376.37
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2102(14)
_cell_length_b                   6.6977(10)
_cell_length_c                   14.702(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.797(4)
_cell_angle_gamma                90
_cell_volume                     896.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9439
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      64.96
_cell_measurement_theta_min      4.23
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1665 before and 0.0797 after correction.
The Ratio of minimum to maximum transmission is 0.8658.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20517
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.562
_diffrn_reflns_theta_min         2.646
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON III area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   'microfocus Metaljet'
_diffrn_source_current           3.57
_diffrn_source_power             0.24947159999999996
_diffrn_source_type              'Incoatec Metaljet'
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3941
_reflns_number_total             3991
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 1752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3991
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.060
_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)+(0.0701P)²+0.1148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C10(H10), C16(H16), C17(H17), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47266(12) 0.5320(2) 0.40045(7) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.57079(12) 0.5377(2) 0.27600(8) 0.0261(3) Uani 1 1 d . . . . .
O3 O 0.99844(12) 0.5124(2) 0.88114(8) 0.0248(3) Uani 1 1 d . . . . .
O4 O 1.05060(12) 0.5215(2) 0.74263(9) 0.0261(3) Uani 1 1 d . . . . .
N1 N -0.42318(17) 0.8148(3) 0.01520(12) 0.0301(4) Uani 1 1 d . . . . .
N2 N 0.06181(19) 0.1855(3) 0.55762(12) 0.0335(4) Uani 1 1 d . . . . .
C1 C -0.33873(18) 0.7291(3) 0.06537(13) 0.0221(4) Uani 1 1 d . . . . .
C2 C -0.23508(18) 0.6204(3) 0.13127(12) 0.0195(3) Uani 1 1 d . . . . .
H2 H -0.213916 0.679405 0.194387 0.023 Uiso 1 1 calc R U . . .
C3 C -0.10699(16) 0.5139(3) 0.09736(11) 0.0211(3) Uani 1 1 d . . . . .
H3 H -0.105968 0.520861 0.029517 0.025 Uiso 1 1 calc R U . . .
C4 C 0.04013(16) 0.5190(3) 0.15604(10) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.05620(16) 0.5206(3) 0.25221(11) 0.0190(3) Uani 1 1 d . . . . .
H5 H -0.028704 0.518113 0.281643 0.023 Uiso 1 1 calc R U . . .
C6 C 0.19482(16) 0.5257(3) 0.30538(10) 0.0174(3) Uani 1 1 d . . . . .
H6 H 0.205689 0.527552 0.370676 0.021 Uiso 1 1 calc R U . . .
C7 C 0.31673(15) 0.5281(3) 0.26038(10) 0.0160(3) Uani 1 1 d . . . . .
N8 N 0.46364(13) 0.5323(2) 0.31593(9) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.16553(16) 0.5218(3) 0.11329(10) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.155440 0.520968 0.048012 0.024 Uiso 1 1 calc R U . . .
C10 C 0.30529(16) 0.5258(3) 0.16538(10) 0.0186(3) Uani 1 1 d . . . . .
H10 H 0.390666 0.526935 0.136396 0.022 Uiso 1 1 calc R U . . .
C11 C -0.2318(2) 0.3960(3) 0.12628(15) 0.0267(4) Uani 1 1 d . . . . .
H11A H -0.301261 0.330158 0.077396 0.032 Uiso 1 1 calc R U . . .
H11B H -0.212084 0.321306 0.184972 0.032 Uiso 1 1 calc R U . . .
C12 C 0.16206(19) 0.2890(3) 0.56188(12) 0.0230(4) Uani 1 1 d . . . . .
C13 C 0.29059(19) 0.4138(3) 0.56560(13) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.367706 0.363499 0.530303 0.023 Uiso 1 1 calc R U . . .
C14 C 0.34812(15) 0.5225(3) 0.65548(10) 0.0190(3) Uani 1 1 d . . . . .
H14 H 0.285002 0.508672 0.704749 0.023 Uiso 1 1 calc R U . . .
C15 C 0.50868(15) 0.5281(3) 0.68932(10) 0.0163(3) Uani 1 1 d . . . . .
C16 C 0.55525(15) 0.5308(3) 0.78427(10) 0.0182(3) Uani 1 1 d . . . . .
H16 H 0.484397 0.534027 0.824905 0.022 Uiso 1 1 calc R U . . .
C17 C 0.70395(16) 0.5288(3) 0.82012(10) 0.0179(3) Uani 1 1 d . . . . .
H17 H 0.735473 0.529719 0.884733 0.022 Uiso 1 1 calc R U . . .
C18 C 0.80495(14) 0.5256(3) 0.75948(10) 0.0157(3) Uani 1 1 d . . . . .
N19 N 0.96185(13) 0.5193(2) 0.79720(9) 0.0180(3) Uani 1 1 d . . . . .
C20 C 0.2787(2) 0.6378(3) 0.57154(14) 0.0254(4) Uani 1 1 d . . . . .
H20A H 0.179985 0.695619 0.572327 0.030 Uiso 1 1 calc R U . . .
H20B H 0.344193 0.719177 0.538849 0.030 Uiso 1 1 calc R U . . .
C21 C 0.61419(16) 0.5271(3) 0.62981(10) 0.0175(3) Uani 1 1 d . . . . .
H21 H 0.583392 0.527973 0.565121 0.021 Uiso 1 1 calc R U . . .
C22 C 0.76350(16) 0.5249(3) 0.66460(10) 0.0172(3) Uani 1 1 d . . . . .
H22 H 0.835155 0.522928 0.624495 0.021 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
O1 N8 1.2327(17) . ?
O2 N8 1.2235(18) . ?
O3 N19 1.2295(18) . ?
O4 N19 1.2299(18) . ?
N1 C1 1.141(2) . ?
N2 C12 1.149(3) . ?
C1 C2 1.448(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.526(2) . ?
C2 C11 1.505(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.4913(19) . ?
C3 C11 1.508(3) . ?
C4 C5 1.399(2) . ?
C4 C9 1.397(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3917(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(2) . ?
C7 N8 1.4700(17) . ?
C7 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.443(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.531(2) . ?
C13 C20 1.508(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.4869(19) . ?
C14 C20 1.512(2) . ?
C15 C16 1.396(2) . ?
C15 C21 1.404(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3903(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(2) . ?
C18 N19 1.4671(17) . ?
C18 C22 1.389(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 0.9500 . ?
C21 C22 1.3920(19) . ?
C22 H22 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
N1 C1 C2 178.0(2) . . ?
C1 C2 H2 115.9 . . ?
C1 C2 C3 118.68(15) . . ?
C1 C2 C11 119.05(17) . . ?
C3 C2 H2 115.9 . . ?
C11 C2 H2 115.9 . . ?
C11 C2 C3 59.66(13) . . ?
C2 C3 H3 115.4 . . ?
C4 C3 C2 118.66(14) . . ?
C4 C3 H3 115.4 . . ?
C4 C3 C11 120.87(15) . . ?
C11 C3 C2 59.48(11) . . ?
C11 C3 H3 115.4 . . ?
C5 C4 C3 122.08(14) . . ?
C9 C4 C3 118.73(13) . . ?
C9 C4 C5 119.19(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.93(14) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.9 . . ?
C7 C6 C5 118.17(13) . . ?
C7 C6 H6 120.9 . . ?
C6 C7 N8 118.59(13) . . ?
C10 C7 C6 122.58(13) . . ?
C10 C7 N8 118.83(13) . . ?
O1 N8 C7 118.32(13) . . ?
O2 N8 O1 123.29(12) . . ?
O2 N8 C7 118.39(12) . . ?
C4 C9 H9 119.6 . . ?
C10 C9 C4 120.71(14) . . ?
C10 C9 H9 119.6 . . ?
C7 C10 C9 118.42(14) . . ?
C7 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C2 C11 C3 60.86(12) . . ?
C2 C11 H11A 117.7 . . ?
C2 C11 H11B 117.7 . . ?
C3 C11 H11A 117.7 . . ?
C3 C11 H11B 117.7 . . ?
H11A C11 H11B 114.8 . . ?
N2 C12 C13 178.0(2) . . ?
C12 C13 H13 115.4 . . ?
C12 C13 C14 118.80(16) . . ?
C12 C13 C20 120.80(18) . . ?
C14 C13 H13 115.4 . . ?
C20 C13 H13 115.4 . . ?
C20 C13 C14 59.69(13) . . ?
C13 C14 H14 114.7 . . ?
C15 C14 C13 119.74(14) . . ?
C15 C14 H14 114.7 . . ?
C15 C14 C20 122.34(15) . . ?
C20 C14 C13 59.42(10) . . ?
C20 C14 H14 114.7 . . ?
C16 C15 C14 118.20(13) . . ?
C16 C15 C21 119.15(13) . . ?
C21 C15 C14 122.63(13) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.87(13) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.44(13) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 N19 118.51(13) . . ?
C17 C18 C22 122.59(12) . . ?
C22 C18 N19 118.89(13) . . ?
O3 N19 O4 123.21(12) . . ?
O3 N19 C18 118.91(13) . . ?
O4 N19 C18 117.88(12) . . ?
C13 C20 C14 60.90(13) . . ?
C13 C20 H20A 117.7 . . ?
C13 C20 H20B 117.7 . . ?
C14 C20 H20A 117.7 . . ?
C14 C20 H20B 117.7 . . ?
H20A C20 H20B 114.8 . . ?
C15 C21 H21 119.7 . . ?
C22 C21 C15 120.68(13) . . ?
C22 C21 H21 119.7 . . ?
C18 C22 C21 118.26(13) . . ?
C18 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?

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
C1 C2 C3 C4 140.39(17) . . . . ?
C1 C2 C3 C11 -108.7(2) . . . . ?
C1 C2 C11 C3 108.12(18) . . . . ?
C2 C3 C4 C5 33.4(3) . . . . ?
C2 C3 C4 C9 -146.78(19) . . . . ?
C3 C4 C5 C6 -179.88(16) . . . . ?
C3 C4 C9 C10 -179.75(17) . . . . ?
C4 C3 C11 C2 107.23(19) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C4 C9 C10 C7 -0.4(3) . . . . ?
C5 C4 C9 C10 0.1(3) . . . . ?
C5 C6 C7 N8 -179.61(16) . . . . ?
C5 C6 C7 C10 0.1(3) . . . . ?
C6 C7 N8 O1 0.5(2) . . . . ?
C6 C7 N8 O2 -178.81(18) . . . . ?
C6 C7 C10 C9 0.3(3) . . . . ?
N8 C7 C10 C9 179.97(16) . . . . ?
C9 C4 C5 C6 0.3(3) . . . . ?
C10 C7 N8 O1 -179.18(17) . . . . ?
C10 C7 N8 O2 1.5(2) . . . . ?
C11 C2 C3 C4 -110.89(19) . . . . ?
C11 C3 C4 C5 -36.3(3) . . . . ?
C11 C3 C4 C9 143.56(19) . . . . ?
C12 C13 C14 C15 136.97(17) . . . . ?
C12 C13 C14 C20 -110.8(2) . . . . ?
C12 C13 C20 C14 107.53(19) . . . . ?
C13 C14 C15 C16 -147.83(16) . . . . ?
C13 C14 C15 C21 31.0(3) . . . . ?
C14 C15 C16 C17 177.70(17) . . . . ?
C14 C15 C21 C22 -177.58(16) . . . . ?
C15 C14 C20 C13 107.93(18) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C15 C21 C22 C18 -0.6(3) . . . . ?
C16 C15 C21 C22 1.3(3) . . . . ?
C16 C17 C18 N19 -178.74(15) . . . . ?
C16 C17 C18 C22 0.2(3) . . . . ?
C17 C18 N19 O3 1.7(2) . . . . ?
C17 C18 N19 O4 -178.23(17) . . . . ?
C17 C18 C22 C21 -0.1(3) . . . . ?
N19 C18 C22 C21 178.81(15) . . . . ?
C20 C13 C14 C15 -112.21(19) . . . . ?
C20 C14 C15 C16 141.55(17) . . . . ?
C20 C14 C15 C21 -39.6(3) . . . . ?
C21 C15 C16 C17 -1.2(3) . . . . ?
C22 C18 N19 O3 -177.32(16) . . . . ?
C22 C18 N19 O4 2.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20230828thc_alphacf3_enantio2__a
_database_code_depnum_ccdc_archive 'CCDC 2351894'
loop_
_audit_author_name
_audit_author_address
'Tan Hao-Chong'
;Sourthern university of science and technology
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2024-04-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(1S,2R)-2-phenyl-2-(trifluoromethyl)cyclopropane-1-carbonitrile
_chemical_formula_moiety         'C11 H8 F3 N'
_chemical_formula_sum            'C11 H8 F3 N'
_chemical_formula_weight         211.18
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.1860(6)
_cell_length_b                   10.3981(8)
_cell_length_c                   12.9161(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     965.10(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9722
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      73.11
_cell_measurement_theta_min      4.75
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.5011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1558 before and 0.1118 after correction.
The Ratio of minimum to maximum transmission is 0.6649.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19415
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         73.328
_diffrn_reflns_theta_min         4.750
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON III area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   'microfocus Metaljet'
_diffrn_source_current           3.57
_diffrn_source_power             0.24947159999999996
_diffrn_source_type              'Incoatec Metaljet'
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2749
_reflns_number_total             2901
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0745P)²+0.0180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1077
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.82(17)
 0.18(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F1 F 0.65358(18) 0.32043(10) 0.53227(9) 0.0310(3) Uani 1 1 d . . . . .
F2 F 0.74611(17) 0.50698(11) 0.58417(7) 0.0261(2) Uani 1 1 d . . . . .
F3 F 0.90515(16) 0.40290(10) 0.46979(9) 0.0279(3) Uani 1 1 d . . . . .
N1 N 0.6235(2) 0.17075(15) 0.31242(12) 0.0283(3) Uani 1 1 d . . . . .
C1 C 0.5896(2) 0.27809(14) 0.32040(13) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.5512(2) 0.41389(14) 0.32615(11) 0.0183(3) Uani 1 1 d . . . . .
H2 H 0.546328 0.458648 0.257676 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6231(2) 0.49678(13) 0.41560(10) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.6954(2) 0.62794(14) 0.38873(11) 0.0155(3) Uani 1 1 d . . . . .
C5 C 0.8425(2) 0.64140(15) 0.31931(12) 0.0205(3) Uani 1 1 d . . . . .
H5 H 0.898918 0.567034 0.290288 0.025 Uiso 1 1 calc R U . . .
C6 C 0.9076(2) 0.76288(16) 0.29213(13) 0.0229(3) Uani 1 1 d . . . . .
H6 H 1.007703 0.771477 0.244557 0.028 Uiso 1 1 calc R U . . .
C7 C 0.8252(2) 0.87180(15) 0.33508(13) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.868765 0.954953 0.316599 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4185(2) 0.46708(15) 0.40710(13) 0.0206(3) Uani 1 1 d . . . . .
H8A H 0.334271 0.537726 0.386034 0.025 Uiso 1 1 calc R U . . .
H8B H 0.364736 0.405882 0.457630 0.025 Uiso 1 1 calc R U . . .
C9 C 0.7310(2) 0.43146(15) 0.50041(11) 0.0209(3) Uani 1 1 d . . . . .
C10 C 0.6794(2) 0.85888(14) 0.40492(12) 0.0192(3) Uani 1 1 d . . . . .
H10 H 0.623792 0.933265 0.434345 0.023 Uiso 1 1 calc R U . . .
C11 C 0.6145(2) 0.73737(14) 0.43190(11) 0.0174(3) Uani 1 1 d . . . . .
H11 H 0.514979 0.728950 0.479811 0.021 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
F1 C9 1.3459(18) . ?
F2 C9 1.3413(17) . ?
F3 C9 1.346(2) . ?
N1 C1 1.147(2) . ?
C1 C2 1.441(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.5312(19) . ?
C2 C8 1.519(2) . ?
C3 C4 1.5002(19) . ?
C3 C8 1.506(2) . ?
C3 C9 1.504(2) . ?
C4 C5 1.393(2) . ?
C4 C11 1.394(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(2) . ?
C7 H7 0.9500 . ?
C7 C10 1.389(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C11 1.391(2) . ?
C11 H11 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
N1 C1 C2 177.46(19) . . ?
C1 C2 H2 114.7 . . ?
C1 C2 C3 121.74(13) . . ?
C1 C2 C8 120.81(14) . . ?
C3 C2 H2 114.7 . . ?
C8 C2 H2 114.7 . . ?
C8 C2 C3 59.18(9) . . ?
C4 C3 C2 117.00(12) . . ?
C4 C3 C8 120.51(12) . . ?
C4 C3 C9 113.61(12) . . ?
C8 C3 C2 60.02(10) . . ?
C9 C3 C2 117.98(12) . . ?
C9 C3 C8 117.62(13) . . ?
C5 C4 C3 120.20(13) . . ?
C5 C4 C11 119.46(14) . . ?
C11 C4 C3 120.33(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.56(14) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.63(14) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.0 . . ?
C10 C7 C6 120.04(14) . . ?
C10 C7 H7 120.0 . . ?
C2 C8 H8A 117.7 . . ?
C2 C8 H8B 117.7 . . ?
C3 C8 C2 60.80(10) . . ?
C3 C8 H8A 117.7 . . ?
C3 C8 H8B 117.7 . . ?
H8A C8 H8B 114.8 . . ?
F1 C9 C3 113.40(13) . . ?
F2 C9 F1 106.80(12) . . ?
F2 C9 F3 106.91(13) . . ?
F2 C9 C3 111.39(13) . . ?
F3 C9 F1 106.55(13) . . ?
F3 C9 C3 111.41(13) . . ?
C7 C10 H10 119.9 . . ?
C7 C10 C11 120.22(14) . . ?
C11 C10 H10 119.9 . . ?
C4 C11 H11 120.0 . . ?
C10 C11 C4 120.09(13) . . ?
C10 C11 H11 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
C1 C2 C3 C4 139.25(15) . . . . ?
C1 C2 C3 C8 -109.41(17) . . . . ?
C1 C2 C3 C9 -2.0(2) . . . . ?
C1 C2 C8 C3 110.94(16) . . . . ?
C2 C3 C4 C5 -58.58(19) . . . . ?
C2 C3 C4 C11 120.58(15) . . . . ?
C2 C3 C9 F1 -44.53(19) . . . . ?
C2 C3 C9 F2 -165.04(13) . . . . ?
C2 C3 C9 F3 75.68(17) . . . . ?
C3 C4 C5 C6 178.50(14) . . . . ?
C3 C4 C11 C10 -178.55(14) . . . . ?
C4 C3 C8 C2 105.57(14) . . . . ?
C4 C3 C9 F1 172.98(13) . . . . ?
C4 C3 C9 F2 52.46(17) . . . . ?
C4 C3 C9 F3 -66.82(16) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C5 C4 C11 C10 0.6(2) . . . . ?
C5 C6 C7 C10 0.2(2) . . . . ?
C6 C7 C10 C11 -0.3(2) . . . . ?
C7 C10 C11 C4 -0.1(2) . . . . ?
C8 C2 C3 C4 -111.34(15) . . . . ?
C8 C2 C3 C9 107.43(15) . . . . ?
C8 C3 C4 C5 -128.05(16) . . . . ?
C8 C3 C4 C11 51.11(19) . . . . ?
C8 C3 C9 F1 24.33(19) . . . . ?
C8 C3 C9 F2 -96.18(16) . . . . ?
C8 C3 C9 F3 144.54(14) . . . . ?
C9 C3 C4 C5 84.31(17) . . . . ?
C9 C3 C4 C11 -96.53(16) . . . . ?
C9 C3 C8 C2 -108.03(14) . . . . ?
C11 C4 C5 C6 -0.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.82(17)
2 0.18(17)

####################################################################### 
# 
# 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_20230814thc_ferrocenecyclocn_0_a
_database_code_depnum_ccdc_archive 'CCDC 2349761'
loop_
_audit_author_name
_audit_author_address
'Tan Hao-Chong'
;Sourthern university of science and technology
China
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-08-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(1S,2S)-2-(Ferrocenyl)cyclopropane-1-carbonitrile
_chemical_formula_moiety         '2(C14 H13 Fe N)'
_chemical_formula_sum            'C28 H26 Fe2 N2'
_chemical_formula_weight         502.21
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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'
Fe Fe -0.2673 2.5550 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.4077(10)
_cell_length_b                   7.4147(8)
_cell_length_c                   14.8363(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.504(4)
_cell_angle_gamma                90
_cell_volume                     1143.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      73.03
_cell_measurement_theta_min      3.70
_shelx_estimated_absorpt_T_max   0.435
_shelx_estimated_absorpt_T_min   0.330
_exptl_absorpt_coefficient_mu    7.123
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.5502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1088 before and 0.0713 after correction.
The Ratio of minimum to maximum transmission is 0.7300.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25521
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         73.445
_diffrn_reflns_theta_min         2.593
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON III area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   'microfocus Metaljet'
_diffrn_source_current           3.57
_diffrn_source_power             0.24947159999999996
_diffrn_source_type              'Incoatec Metaljet'
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                5810
_reflns_number_total             6412
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.128(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         6412
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.083
_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)+(0.0362P)²+1.0065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.872(12)
 0.128(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C16(H16), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14),
 C15(H15), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.61266(5) 1.01305(5) 0.83053(4) 0.01768(17) Uani 1 1 d . . . . .
Fe2 Fe 0.88678(5) -0.01209(5) 0.17022(4) 0.01869(18) Uani 1 1 d . . . . .
C28 C 0.4876(5) 1.1366(9) 0.9119(4) 0.0491(17) Uani 1 1 d . . . . .
H28 H 0.472343 1.104839 0.972580 0.059 Uiso 1 1 calc R U . . .
C26 C 0.8204(4) 0.1646(8) 0.2611(3) 0.0332(11) Uani 1 1 d . . . . .
C27 C 0.7054(4) 0.0740(7) 0.1335(3) 0.0259(9) Uani 1 1 d . . . . .
H27 H 0.647(4) 0.000(7) 0.102(3) 0.031 Uiso 1 1 d . U . . .
C25 C 0.7185(4) 0.0553(7) 0.2275(3) 0.0264(10) Uani 1 1 d . . . . .
H25 H 0.673(4) -0.043(7) 0.263(3) 0.032 Uiso 1 1 d . U . . .
C9 C 0.9344(5) -0.2651(8) 0.2125(4) 0.0379(12) Uani 1 1 d . . . . .
H9 H 0.876(5) -0.313(8) 0.264(3) 0.046 Uiso 1 1 d . U . . .
C10 C 1.0363(5) -0.1449(9) 0.2325(4) 0.0444(14) Uani 1 1 d . . . . .
H10 H 1.066(5) -0.123(9) 0.284(4) 0.053 Uiso 1 1 d . U . . .
C20 C 1.0748(4) -0.0703(8) 0.1506(4) 0.0424(13) Uani 1 1 d . . . . .
H20 H 1.136(5) 0.043(8) 0.153(4) 0.051 Uiso 1 1 d . U . . .
C21 C 0.9102(4) -0.2649(8) 0.1190(4) 0.0355(11) Uani 1 1 d . . . . .
H21 H 0.837(5) -0.355(8) 0.092(3) 0.043 Uiso 1 1 d . U . . .
C1 C 0.6825(4) 0.8099(8) 0.7533(3) 0.0309(10) Uani 1 1 d . . . . .
C2 C 0.6394(4) 0.7404(7) 0.8349(4) 0.0340(11) Uani 1 1 d . . . . .
H2 H 0.574446 0.651606 0.840678 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7092(4) 0.8255(8) 0.9068(3) 0.0311(10) Uani 1 1 d . . . . .
H3 H 0.699042 0.803427 0.969174 0.037 Uiso 1 1 calc R U . . .
C4 C 0.7968(4) 0.9490(7) 0.8706(3) 0.0240(8) Uani 1 1 d . . . . .
H4 H 0.855688 1.023350 0.904255 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7815(3) 0.9425(7) 0.7753(3) 0.0253(9) Uani 1 1 d . . . . .
H5 H 0.827442 1.011950 0.733551 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6469(4) 0.7255(6) 0.6653(3) 0.0329(8) Uani 1 1 d . . . . .
H6 H 0.697170 0.615621 0.649953 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6185(5) 0.8517(7) 0.5899(3) 0.0434(10) Uani 1 1 d . . . . .
H7 H 0.615460 0.983162 0.604744 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6686(5) 0.8014(8) 0.5024(3) 0.0492(12) Uani 1 1 d . . . . .
N9 N 0.7144(6) 0.7571(10) 0.4342(3) 0.071(2) Uani 1 1 d . . . . .
C11 C 0.5146(4) 0.7360(9) 0.6239(4) 0.0432(13) Uani 1 1 d . . . . .
H11A H 0.447562 0.794429 0.659150 0.052 Uiso 1 1 calc R U . . .
H11B H 0.484070 0.633995 0.585589 0.052 Uiso 1 1 calc R U . . .
C12 C 0.4726(5) 1.1508(9) 0.7590(4) 0.0389(12) Uani 1 1 d . . . . .
H12 H 0.445561 1.130316 0.697831 0.047 Uiso 1 1 calc R U . . .
C13 C 0.4214(4) 1.0676(8) 0.8349(5) 0.0463(15) Uani 1 1 d . . . . .
H13 H 0.354373 0.980614 0.834133 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5812(5) 1.2618(8) 0.8839(4) 0.0403(13) Uani 1 1 d . . . . .
H14 H 0.639679 1.327633 0.922226 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5716(4) 1.2708(7) 0.7897(4) 0.0354(12) Uani 1 1 d . . . . .
H15 H 0.622396 1.344231 0.752772 0.042 Uiso 1 1 calc R U . . .
C16 C 0.8615(4) 0.1638(6) 0.3581(3) 0.0325(8) Uani 1 1 d . . . . .
H16 H 0.847879 0.048033 0.390839 0.039 Uiso 1 1 calc R U . . .
C17 C 0.9750(5) 0.2766(12) 0.3925(4) 0.0582(19) Uani 1 1 d . . . . .
H17A H 1.022032 0.346836 0.347730 0.070 Uiso 1 1 calc R U . . .
H17B H 1.029450 0.227556 0.443117 0.070 Uiso 1 1 calc R U . . .
C18 C 0.8395(4) 0.3379(7) 0.4127(3) 0.0391(10) Uani 1 1 d . . . . .
H18 H 0.805777 0.443844 0.377318 0.047 Uiso 1 1 calc R U . . .
C19 C 0.7926(5) 0.3187(8) 0.5027(3) 0.0442(11) Uani 1 1 d . . . . .
N21 N 0.7570(6) 0.2956(10) 0.5736(3) 0.0725(19) Uani 1 1 d . . . . .
C22 C 0.8708(4) 0.2568(7) 0.1851(4) 0.0324(11) Uani 1 1 d . . . . .
H22 H 0.939728 0.340836 0.187211 0.039 Uiso 1 1 calc R U . . .
C23 C 0.7991(4) 0.2000(7) 0.1057(3) 0.0315(10) Uani 1 1 d . . . . .
H23 H 0.811551 0.238959 0.045690 0.038 Uiso 1 1 calc R U . . .
C24 C 0.9955(5) -0.1428(9) 0.0797(3) 0.0385(12) Uani 1 1 d . . . . .
H24 H 0.998903 -0.114671 0.017409 0.046 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
Fe1 C28 2.032(4) . ?
Fe1 C1 2.046(5) . ?
Fe1 C2 2.041(5) . ?
Fe1 C3 2.031(5) . ?
Fe1 C4 2.038(4) . ?
Fe1 C5 2.040(4) . ?
Fe1 C12 2.040(5) . ?
Fe1 C13 2.035(4) . ?
Fe1 C14 2.039(5) . ?
Fe1 C15 2.044(5) . ?
Fe2 C26 2.023(5) . ?
Fe2 C27 2.044(4) . ?
Fe2 C25 2.042(4) . ?
Fe2 C9 2.033(5) . ?
Fe2 C10 2.030(5) . ?
Fe2 C20 2.038(4) . ?
Fe2 C21 2.041(6) . ?
Fe2 C22 2.013(5) . ?
Fe2 C23 2.036(5) . ?
Fe2 C24 2.038(5) . ?
C28 H28 0.9500 . ?
C28 C13 1.405(9) . ?
C28 C14 1.421(8) . ?
C26 C25 1.409(6) . ?
C26 C16 1.482(6) . ?
C26 C22 1.437(7) . ?
C27 H27 0.93(5) . ?
C27 C25 1.403(6) . ?
C27 C23 1.425(7) . ?
C25 H25 1.03(5) . ?
C9 H9 1.06(5) . ?
C9 C10 1.407(8) . ?
C9 C21 1.399(8) . ?
C10 H10 0.83(6) . ?
C10 C20 1.409(8) . ?
C20 H20 1.06(6) . ?
C20 C24 1.415(8) . ?
C21 H21 1.08(5) . ?
C21 C24 1.412(8) . ?
C1 C2 1.408(7) . ?
C1 C5 1.451(6) . ?
C1 C6 1.479(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.413(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.415(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.417(6) . ?
C5 H5 0.9500 . ?
C6 H6 1.0000 . ?
C6 C7 1.478(7) . ?
C6 C11 1.485(6) . ?
C7 H7 1.0000 . ?
C7 C8 1.469(7) . ?
C7 C11 1.486(7) . ?
C8 N9 1.183(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.409(8) . ?
C12 C15 1.422(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.397(8) . ?
C15 H15 0.9500 . ?
C16 H16 1.0000 . ?
C16 C17 1.518(7) . ?
C16 C18 1.546(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.524(7) . ?
C18 H18 1.0000 . ?
C18 C19 1.449(6) . ?
C19 N21 1.143(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.430(7) . ?
C23 H23 0.9500 . ?
C24 H24 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
C28 Fe1 C1 156.6(2) . . ?
C28 Fe1 C2 121.1(2) . . ?
C28 Fe1 C4 123.4(2) . . ?
C28 Fe1 C5 160.1(2) . . ?
C28 Fe1 C12 67.8(2) . . ?
C28 Fe1 C13 40.4(2) . . ?
C28 Fe1 C14 40.9(2) . . ?
C28 Fe1 C15 67.9(2) . . ?
C2 Fe1 C1 40.3(2) . . ?
C2 Fe1 C15 164.1(2) . . ?
C3 Fe1 C28 107.0(2) . . ?
C3 Fe1 C1 68.2(2) . . ?
C3 Fe1 C2 40.6(2) . . ?
C3 Fe1 C4 40.70(18) . . ?
C3 Fe1 C5 68.56(18) . . ?
C3 Fe1 C12 163.3(2) . . ?
C3 Fe1 C13 125.4(2) . . ?
C3 Fe1 C14 119.1(2) . . ?
C3 Fe1 C15 153.8(2) . . ?
C4 Fe1 C1 68.83(17) . . ?
C4 Fe1 C2 68.6(2) . . ?
C4 Fe1 C5 40.66(16) . . ?
C4 Fe1 C12 155.5(2) . . ?
C4 Fe1 C14 105.2(2) . . ?
C4 Fe1 C15 119.1(2) . . ?
C5 Fe1 C1 41.60(18) . . ?
C5 Fe1 C2 68.91(19) . . ?
C5 Fe1 C12 121.9(2) . . ?
C5 Fe1 C15 107.1(2) . . ?
C12 Fe1 C1 109.9(2) . . ?
C12 Fe1 C2 127.3(2) . . ?
C12 Fe1 C15 40.7(2) . . ?
C13 Fe1 C1 122.4(2) . . ?
C13 Fe1 C2 109.1(2) . . ?
C13 Fe1 C4 161.1(2) . . ?
C13 Fe1 C5 157.7(2) . . ?
C13 Fe1 C12 40.5(2) . . ?
C13 Fe1 C14 68.5(2) . . ?
C13 Fe1 C15 68.4(2) . . ?
C14 Fe1 C1 161.9(2) . . ?
C14 Fe1 C2 155.1(2) . . ?
C14 Fe1 C5 123.0(2) . . ?
C14 Fe1 C12 68.0(2) . . ?
C14 Fe1 C15 40.0(2) . . ?
C15 Fe1 C1 126.7(2) . . ?
C26 Fe2 C27 68.75(18) . . ?
C26 Fe2 C25 40.55(17) . . ?
C26 Fe2 C9 118.5(2) . . ?
C26 Fe2 C10 106.7(2) . . ?
C26 Fe2 C20 126.2(2) . . ?
C26 Fe2 C21 153.2(2) . . ?
C26 Fe2 C23 69.8(2) . . ?
C26 Fe2 C24 164.2(2) . . ?
C25 Fe2 C27 40.16(18) . . ?
C9 Fe2 C27 125.5(2) . . ?
C9 Fe2 C25 107.4(2) . . ?
C9 Fe2 C20 68.0(2) . . ?
C9 Fe2 C21 40.2(2) . . ?
C9 Fe2 C23 163.0(2) . . ?
C9 Fe2 C24 68.3(2) . . ?
C10 Fe2 C27 162.5(2) . . ?
C10 Fe2 C25 125.7(2) . . ?
C10 Fe2 C9 40.5(2) . . ?
C10 Fe2 C20 40.5(2) . . ?
C10 Fe2 C21 67.8(2) . . ?
C10 Fe2 C23 155.2(2) . . ?
C10 Fe2 C24 68.4(2) . . ?
C20 Fe2 C27 155.5(2) . . ?
C20 Fe2 C25 163.3(2) . . ?
C20 Fe2 C21 67.7(2) . . ?
C20 Fe2 C24 40.6(2) . . ?
C21 Fe2 C27 108.13(19) . . ?
C21 Fe2 C25 119.87(19) . . ?
C22 Fe2 C26 41.7(2) . . ?
C22 Fe2 C27 68.9(2) . . ?
C22 Fe2 C25 68.63(19) . . ?
C22 Fe2 C9 154.2(2) . . ?
C22 Fe2 C10 119.7(2) . . ?
C22 Fe2 C20 108.1(2) . . ?
C22 Fe2 C21 164.1(2) . . ?
C22 Fe2 C23 41.4(2) . . ?
C22 Fe2 C24 126.4(2) . . ?
C23 Fe2 C27 40.86(18) . . ?
C23 Fe2 C25 68.39(18) . . ?
C23 Fe2 C20 120.7(2) . . ?
C23 Fe2 C21 126.3(2) . . ?
C23 Fe2 C24 107.9(2) . . ?
C24 Fe2 C27 120.36(19) . . ?
C24 Fe2 C25 154.3(2) . . ?
C24 Fe2 C21 40.5(2) . . ?
Fe1 C28 H28 126.1 . . ?
C13 C28 Fe1 69.9(3) . . ?
C13 C28 H28 125.7 . . ?
C13 C28 C14 108.5(5) . . ?
C14 C28 Fe1 69.8(3) . . ?
C14 C28 H28 125.7 . . ?
C25 C26 Fe2 70.4(3) . . ?
C25 C26 C16 121.5(4) . . ?
C25 C26 C22 106.9(4) . . ?
C16 C26 Fe2 123.5(4) . . ?
C22 C26 Fe2 68.8(3) . . ?
C22 C26 C16 131.6(4) . . ?
Fe2 C27 H27 122(3) . . ?
C25 C27 Fe2 69.8(2) . . ?
C25 C27 H27 118(3) . . ?
C25 C27 C23 108.3(4) . . ?
C23 C27 Fe2 69.3(2) . . ?
C23 C27 H27 133(3) . . ?
Fe2 C25 H25 118(3) . . ?
C26 C25 Fe2 69.0(2) . . ?
C26 C25 H25 126(3) . . ?
C27 C25 Fe2 70.0(2) . . ?
C27 C25 C26 109.6(4) . . ?
C27 C25 H25 124(3) . . ?
Fe2 C9 H9 113(3) . . ?
C10 C9 Fe2 69.6(3) . . ?
C10 C9 H9 121(3) . . ?
C21 C9 Fe2 70.2(3) . . ?
C21 C9 H9 129(3) . . ?
C21 C9 C10 108.0(5) . . ?
Fe2 C10 H10 125(4) . . ?
C9 C10 Fe2 69.9(3) . . ?
C9 C10 H10 125(4) . . ?
C9 C10 C20 107.9(5) . . ?
C20 C10 Fe2 70.0(3) . . ?
C20 C10 H10 127(4) . . ?
Fe2 C20 H20 114(3) . . ?
C10 C20 Fe2 69.4(3) . . ?
C10 C20 H20 118(3) . . ?
C10 C20 C24 108.2(5) . . ?
C24 C20 Fe2 69.7(2) . . ?
C24 C20 H20 132(3) . . ?
Fe2 C21 H21 128(3) . . ?
C9 C21 Fe2 69.6(3) . . ?
C9 C21 H21 117(3) . . ?
C9 C21 C24 108.7(4) . . ?
C24 C21 Fe2 69.7(3) . . ?
C24 C21 H21 134(3) . . ?
C2 C1 Fe1 69.7(3) . . ?
C2 C1 C5 107.7(4) . . ?
C2 C1 C6 121.8(5) . . ?
C5 C1 Fe1 69.0(2) . . ?
C5 C1 C6 129.3(4) . . ?
C6 C1 Fe1 136.4(3) . . ?
Fe1 C2 H2 126.4 . . ?
C1 C2 Fe1 70.0(3) . . ?
C1 C2 H2 125.9 . . ?
C1 C2 C3 108.3(4) . . ?
C3 C2 Fe1 69.3(3) . . ?
C3 C2 H2 125.9 . . ?
Fe1 C3 H3 126.0 . . ?
C2 C3 Fe1 70.1(3) . . ?
C2 C3 H3 125.6 . . ?
C2 C3 C4 108.7(4) . . ?
C4 C3 Fe1 69.9(3) . . ?
C4 C3 H3 125.6 . . ?
Fe1 C4 H4 126.5 . . ?
C3 C4 Fe1 69.4(2) . . ?
C3 C4 H4 125.9 . . ?
C3 C4 C5 108.1(4) . . ?
C5 C4 Fe1 69.7(2) . . ?
C5 C4 H4 125.9 . . ?
Fe1 C5 H5 126.1 . . ?
C1 C5 Fe1 69.4(2) . . ?
C1 C5 H5 126.4 . . ?
C4 C5 Fe1 69.6(2) . . ?
C4 C5 C1 107.2(4) . . ?
C4 C5 H5 126.4 . . ?
C1 C6 H6 115.6 . . ?
C1 C6 C11 122.3(4) . . ?
C7 C6 C1 115.7(4) . . ?
C7 C6 H6 115.6 . . ?
C7 C6 C11 60.2(3) . . ?
C11 C6 H6 115.6 . . ?
C6 C7 H7 117.3 . . ?
C6 C7 C11 60.2(3) . . ?
C8 C7 C6 116.2(5) . . ?
C8 C7 H7 117.3 . . ?
C8 C7 C11 116.4(5) . . ?
C11 C7 H7 117.3 . . ?
N9 C8 C7 176.5(6) . . ?
C6 C11 C7 59.7(3) . . ?
C6 C11 H11A 117.8 . . ?
C6 C11 H11B 117.8 . . ?
C7 C11 H11A 117.8 . . ?
C7 C11 H11B 117.8 . . ?
H11A C11 H11B 114.9 . . ?
Fe1 C12 H12 126.3 . . ?
C13 C12 Fe1 69.6(3) . . ?
C13 C12 H12 125.9 . . ?
C13 C12 C15 108.1(5) . . ?
C15 C12 Fe1 69.8(3) . . ?
C15 C12 H12 125.9 . . ?
Fe1 C13 H13 125.7 . . ?
C28 C13 Fe1 69.7(3) . . ?
C28 C13 C12 107.6(5) . . ?
C28 C13 H13 126.2 . . ?
C12 C13 Fe1 70.0(3) . . ?
C12 C13 H13 126.2 . . ?
Fe1 C14 H14 126.0 . . ?
C28 C14 Fe1 69.3(3) . . ?
C28 C14 H14 126.2 . . ?
C15 C14 Fe1 70.2(3) . . ?
C15 C14 C28 107.7(5) . . ?
C15 C14 H14 126.2 . . ?
Fe1 C15 H15 126.3 . . ?
C12 C15 Fe1 69.5(3) . . ?
C12 C15 H15 126.0 . . ?
C14 C15 Fe1 69.8(3) . . ?
C14 C15 C12 108.1(5) . . ?
C14 C15 H15 126.0 . . ?
C26 C16 H16 115.7 . . ?
C26 C16 C17 120.8(4) . . ?
C26 C16 C18 117.5(4) . . ?
C17 C16 H16 115.7 . . ?
C17 C16 C18 59.7(4) . . ?
C18 C16 H16 115.7 . . ?
C16 C17 H17A 117.7 . . ?
C16 C17 H17B 117.7 . . ?
C16 C17 C18 61.1(3) . . ?
H17A C17 H17B 114.8 . . ?
C18 C17 H17A 117.7 . . ?
C18 C17 H17B 117.7 . . ?
C16 C18 H18 115.9 . . ?
C17 C18 C16 59.2(4) . . ?
C17 C18 H18 115.9 . . ?
C19 C18 C16 117.7(4) . . ?
C19 C18 C17 120.2(5) . . ?
C19 C18 H18 115.9 . . ?
N21 C19 C18 177.0(7) . . ?
Fe2 C22 H22 126.0 . . ?
C26 C22 Fe2 69.5(3) . . ?
C26 C22 H22 125.9 . . ?
C23 C22 Fe2 70.2(3) . . ?
C23 C22 C26 108.2(4) . . ?
C23 C22 H22 125.9 . . ?
Fe2 C23 H23 126.8 . . ?
C27 C23 Fe2 69.9(3) . . ?
C27 C23 C22 107.1(4) . . ?
C27 C23 H23 126.5 . . ?
C22 C23 Fe2 68.5(3) . . ?
C22 C23 H23 126.5 . . ?
Fe2 C24 H24 125.6 . . ?
C20 C24 Fe2 69.7(3) . . ?
C20 C24 H24 126.4 . . ?
C21 C24 Fe2 69.9(3) . . ?
C21 C24 C20 107.1(4) . . ?
C21 C24 H24 126.4 . . ?

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
Fe1 C28 C13 C12 -60.0(3) . . . . ?
Fe1 C28 C14 C15 59.9(3) . . . . ?
Fe1 C1 C2 C3 -59.0(3) . . . . ?
Fe1 C1 C5 C4 59.6(3) . . . . ?
Fe1 C1 C6 C7 47.4(6) . . . . ?
Fe1 C1 C6 C11 -22.2(8) . . . . ?
Fe1 C2 C3 C4 -59.4(3) . . . . ?
Fe1 C3 C4 C5 -59.2(3) . . . . ?
Fe1 C4 C5 C1 -59.5(3) . . . . ?
Fe1 C12 C13 C28 59.8(3) . . . . ?
Fe1 C12 C15 C14 -59.3(3) . . . . ?
Fe1 C14 C15 C12 59.1(4) . . . . ?
Fe2 C26 C25 C27 -58.4(3) . . . . ?
Fe2 C26 C16 C17 91.2(6) . . . . ?
Fe2 C26 C16 C18 160.6(3) . . . . ?
Fe2 C26 C22 C23 59.8(3) . . . . ?
Fe2 C27 C25 C26 57.8(3) . . . . ?
Fe2 C27 C23 C22 -58.5(3) . . . . ?
Fe2 C9 C10 C20 -59.9(4) . . . . ?
Fe2 C9 C21 C24 58.8(4) . . . . ?
Fe2 C10 C20 C24 -59.1(4) . . . . ?
Fe2 C20 C24 C21 -60.1(3) . . . . ?
Fe2 C21 C24 C20 60.0(4) . . . . ?
Fe2 C22 C23 C27 59.4(3) . . . . ?
C28 C14 C15 Fe1 -59.4(3) . . . . ?
C28 C14 C15 C12 -0.2(5) . . . . ?
C26 C16 C17 C18 106.0(5) . . . . ?
C26 C16 C18 C17 -111.3(5) . . . . ?
C26 C16 C18 C19 138.2(4) . . . . ?
C26 C22 C23 Fe2 -59.4(3) . . . . ?
C26 C22 C23 C27 0.1(5) . . . . ?
C25 C26 C16 C17 177.4(5) . . . . ?
C25 C26 C16 C18 -113.2(5) . . . . ?
C25 C26 C22 Fe2 -60.4(3) . . . . ?
C25 C26 C22 C23 -0.7(5) . . . . ?
C25 C27 C23 Fe2 59.1(3) . . . . ?
C25 C27 C23 C22 0.5(5) . . . . ?
C9 C10 C20 Fe2 59.8(4) . . . . ?
C9 C10 C20 C24 0.7(6) . . . . ?
C9 C21 C24 Fe2 -58.8(3) . . . . ?
C9 C21 C24 C20 1.2(6) . . . . ?
C10 C9 C21 Fe2 -59.6(4) . . . . ?
C10 C9 C21 C24 -0.8(6) . . . . ?
C10 C20 C24 Fe2 58.9(4) . . . . ?
C10 C20 C24 C21 -1.2(6) . . . . ?
C21 C9 C10 Fe2 60.0(3) . . . . ?
C21 C9 C10 C20 0.0(6) . . . . ?
C1 C2 C3 Fe1 59.4(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 C8 139.1(4) . . . . ?
C1 C6 C7 C11 -114.1(4) . . . . ?
C1 C6 C11 C7 103.3(5) . . . . ?
C2 C1 C5 Fe1 -59.1(3) . . . . ?
C2 C1 C5 C4 0.5(5) . . . . ?
C2 C1 C6 C7 140.8(5) . . . . ?
C2 C1 C6 C11 71.1(7) . . . . ?
C2 C3 C4 Fe1 59.5(3) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 Fe1 59.0(3) . . . . ?
C3 C4 C5 C1 -0.5(5) . . . . ?
C5 C1 C2 Fe1 58.7(3) . . . . ?
C5 C1 C2 C3 -0.3(5) . . . . ?
C5 C1 C6 C7 -53.3(6) . . . . ?
C5 C1 C6 C11 -122.9(5) . . . . ?
C6 C1 C2 Fe1 -132.7(4) . . . . ?
C6 C1 C2 C3 168.3(4) . . . . ?
C6 C1 C5 Fe1 133.4(5) . . . . ?
C6 C1 C5 C4 -166.9(5) . . . . ?
C8 C7 C11 C6 106.5(5) . . . . ?
C11 C6 C7 C8 -106.8(5) . . . . ?
C13 C28 C14 Fe1 -59.4(3) . . . . ?
C13 C28 C14 C15 0.5(5) . . . . ?
C13 C12 C15 Fe1 59.2(4) . . . . ?
C13 C12 C15 C14 -0.1(6) . . . . ?
C14 C28 C13 Fe1 59.4(3) . . . . ?
C14 C28 C13 C12 -0.6(6) . . . . ?
C15 C12 C13 Fe1 -59.3(3) . . . . ?
C15 C12 C13 C28 0.4(6) . . . . ?
C16 C26 C25 Fe2 -118.0(5) . . . . ?
C16 C26 C25 C27 -176.4(4) . . . . ?
C16 C26 C22 Fe2 116.5(6) . . . . ?
C16 C26 C22 C23 176.3(5) . . . . ?
C16 C17 C18 C19 106.2(5) . . . . ?
C17 C16 C18 C19 -110.4(6) . . . . ?
C22 C26 C25 Fe2 59.4(3) . . . . ?
C22 C26 C25 C27 1.0(5) . . . . ?
C22 C26 C16 C17 0.8(8) . . . . ?
C22 C26 C16 C18 70.2(6) . . . . ?
C23 C27 C25 Fe2 -58.7(3) . . . . ?
C23 C27 C25 C26 -1.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.872(12)
2 0.128(12)

####################################################################### 
# 
# 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_20230327alphabr_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2349764'
loop_
_audit_author_name
_audit_author_address
'Tan Hao-Chong'
;Sourthern university of science and technology
China
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2024-04-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(1R,2R)-2-bromo-2-phenylcyclopropane-1-carbonitrile
_chemical_formula_moiety         'C10 H8 Br N'
_chemical_formula_sum            'C10 H8 Br N'
_chemical_formula_weight         222.08
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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'
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.0173(4)
_cell_length_b                   9.8390(6)
_cell_length_c                   12.9563(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     894.54(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8683
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.73
_cell_measurement_theta_min      5.94
_shelx_estimated_absorpt_T_max   0.702
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    3.812
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6502
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1528 before and 0.0758 after correction.
The Ratio of minimum to maximum transmission is 0.8630.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20294
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         71.122
_diffrn_reflns_theta_min         4.910
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24947159999999996
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2285
_reflns_number_total             2614
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 
;
 Flack x determined using 872 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.120
_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)+(0.0154P)²+0.2469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0586
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br1 Br 0.71213(5) 0.53078(4) 0.67377(3) 0.01801(11) Uani 1 1 d . . . . .
N1 N 0.6446(5) 0.2936(4) 0.4474(3) 0.0271(8) Uani 1 1 d . . . . .
C1 C 0.6175(5) 0.2742(4) 0.5336(3) 0.0175(8) Uani 1 1 d . . . . .
C2 C 0.5764(5) 0.2495(4) 0.6411(3) 0.0176(8) Uani 1 1 d . . . . .
H2 H 0.466400 0.187312 0.654520 0.021 Uiso 1 1 calc R . . . .
C3 C 0.6075(5) 0.3587(4) 0.7217(3) 0.0138(7) Uani 1 1 d . . . . .
C4 C 0.4645(5) 0.3784(3) 0.8050(3) 0.0136(7) Uani 1 1 d . . . . .
C5 C 0.5215(5) 0.3881(4) 0.9075(3) 0.0195(8) Uani 1 1 d . . . . .
H5 H 0.652924 0.381459 0.924320 0.023 Uiso 1 1 calc R . . . .
C6 C 0.3893(6) 0.4074(4) 0.9850(3) 0.0225(9) Uani 1 1 d . . . . .
H6 H 0.429596 0.413342 1.054872 0.027 Uiso 1 1 calc R . . . .
C7 C 0.1971(7) 0.4182(4) 0.9606(3) 0.0208(8) Uani 1 1 d . . . . .
H7 H 0.105681 0.431770 1.013742 0.025 Uiso 1 1 calc R . . . .
C8 C 0.7394(6) 0.2398(4) 0.7189(3) 0.0205(9) Uani 1 1 d . . . . .
H8A H 0.728441 0.171548 0.774702 0.025 Uiso 1 1 calc R . . . .
H8B H 0.870609 0.255134 0.693267 0.025 Uiso 1 1 calc R . . . .
C9 C 0.2712(6) 0.3884(3) 0.7814(3) 0.0163(7) Uani 1 1 d . . . . .
H9 H 0.230042 0.380940 0.711798 0.020 Uiso 1 1 calc R . . . .
C10 C 0.1392(6) 0.4092(4) 0.8589(3) 0.0214(8) Uani 1 1 d . . . . .
H10 H 0.007879 0.417359 0.842198 0.026 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
Br1 C3 1.947(4) . ?
N1 C1 1.149(5) . ?
C1 C2 1.443(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.514(5) . ?
C2 C8 1.528(5) . ?
C3 C4 1.486(5) . ?
C3 C8 1.492(5) . ?
C4 C5 1.390(5) . ?
C4 C9 1.394(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(5) . ?
C7 H7 0.9500 . ?
C7 C10 1.382(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.381(5) . ?
C10 H10 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
N1 C1 C2 178.0(4) . . ?
C1 C2 H2 115.2 . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 C8 119.8(3) . . ?
C3 C2 H2 115.2 . . ?
C3 C2 C8 58.8(2) . . ?
C8 C2 H2 115.2 . . ?
C2 C3 Br1 116.9(3) . . ?
C4 C3 Br1 111.9(2) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 C8 122.6(3) . . ?
C8 C3 Br1 116.1(3) . . ?
C8 C3 C2 61.1(2) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 C9 119.0(3) . . ?
C9 C4 C3 120.5(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.8(4) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.1 . . ?
C10 C7 C6 119.8(4) . . ?
C10 C7 H7 120.1 . . ?
C2 C8 H8A 117.8 . . ?
C2 C8 H8B 117.8 . . ?
C3 C8 C2 60.2(2) . . ?
C3 C8 H8A 117.8 . . ?
C3 C8 H8B 117.8 . . ?
H8A C8 H8B 114.9 . . ?
C4 C9 H9 119.9 . . ?
C10 C9 C4 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C7 C10 H10 119.8 . . ?
C9 C10 C7 120.4(4) . . ?
C9 C10 H10 119.8 . . ?

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
Br1 C3 C4 C5 -86.1(4) . . . . ?
Br1 C3 C4 C9 93.3(4) . . . . ?
Br1 C3 C8 C2 -107.7(3) . . . . ?
C1 C2 C3 Br1 -1.8(5) . . . . ?
C1 C2 C3 C4 138.6(4) . . . . ?
C1 C2 C3 C8 -108.3(4) . . . . ?
C1 C2 C8 C3 110.4(4) . . . . ?
C2 C3 C4 C5 131.7(4) . . . . ?
C2 C3 C4 C9 -48.9(5) . . . . ?
C3 C4 C5 C6 179.5(4) . . . . ?
C3 C4 C9 C10 -178.8(3) . . . . ?
C4 C3 C8 C2 108.6(4) . . . . ?
C4 C5 C6 C7 -0.5(6) . . . . ?
C4 C9 C10 C7 -1.0(6) . . . . ?
C5 C4 C9 C10 0.7(5) . . . . ?
C5 C6 C7 C10 0.2(6) . . . . ?
C6 C7 C10 C9 0.5(6) . . . . ?
C8 C2 C3 Br1 106.5(3) . . . . ?
C8 C2 C3 C4 -113.1(4) . . . . ?
C8 C3 C4 C5 58.9(5) . . . . ?
C8 C3 C4 C9 -121.6(4) . . . . ?
C9 C4 C5 C6 0.0(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
