# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_str1708
_database_code_depnum_ccdc_archive 'CCDC 1455126'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;
_audit_creation_date             2014-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_systematic        2-methyl-2-nitro-3-phenyloxirane
_chemical_formula_moiety         'C9 H9 N O3'
_chemical_formula_sum            'C9 H9 N O3'
_chemical_formula_weight         179.18
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   5.4300(2)
_cell_length_b                   7.8748(5)
_cell_length_c                   20.6997(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     885.13(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    200
_cell_measurement_theta_max      70.1890
_cell_measurement_theta_min      4.2320
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3445
_exptl_crystal_description       needle
_exptl_crystal_F_000             377.3919
_exptl_crystal_size_max          0.2772
_exptl_crystal_size_mid          0.1307
_exptl_crystal_size_min          0.0815
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7633
_diffrn_reflns_theta_full        71.8224
_diffrn_reflns_theta_max         71.82
_diffrn_reflns_theta_min         4.27
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9891
_diffrn_measured_fraction_theta_max 0.9891
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   41.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2932   37.0000    0.0000 150

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00   41.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2932   57.0000   60.0000 185

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00  129.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.2932  178.0000 -120.0000 120

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00  129.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.2932  178.0000  -30.0000 120

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   89.60   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000  -60.0000 106

#__ type_ start__ end____ width___ exp.time_
  6 omega   28.00   97.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000    0.0000 115

#__ type_ start__ end____ width___ exp.time_
  7 omega  100.00  178.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000   90.0000 130

#__ type_ start__ end____ width___ exp.time_
  8 omega   57.00  150.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  178.0000   90.0000 155

#__ type_ start__ end____ width___ exp.time_
  9 omega   26.00   89.60   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000  120.0000 106

#__ type_ start__ end____ width___ exp.time_
 10 omega   28.00   97.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000   30.0000 115

#__ type_ start__ end____ width___ exp.time_
 11 omega   28.00   97.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000   60.0000 115

#__ type_ start__ end____ width___ exp.time_
 12 omega   26.00   89.60   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000 -150.0000 106

#__ type_ start__ end____ width___ exp.time_
 13 omega -115.00   -5.80   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2932  -57.0000 -150.0000 182

#__ type_ start__ end____ width___ exp.time_
 14 omega -115.00   -5.80   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2932  -57.0000   90.0000 182

#__ type_ start__ end____ width___ exp.time_
 15 omega -115.00   -5.80   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2932  -57.0000  -30.0000 182

#__ type_ start__ end____ width___ exp.time_
 16 omega   69.00  177.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   30.0000  120.0000 180

#__ type_ start__ end____ width___ exp.time_
 17 omega   69.00  177.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   30.0000   30.0000 180

#__ type_ start__ end____ width___ exp.time_
 18 omega   20.00  108.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000 -180.0000 147

#__ type_ start__ end____ width___ exp.time_
 19 omega   71.00  165.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000  150.0000 157

#__ type_ start__ end____ width___ exp.time_
 20 omega   26.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   15.0000  -60.0000 252
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2754449000
_diffrn_orient_matrix_UB_12      0.0415690000
_diffrn_orient_matrix_UB_13      0.0079828000
_diffrn_orient_matrix_UB_21      0.0521614000
_diffrn_orient_matrix_UB_22      -0.0757808000
_diffrn_orient_matrix_UB_23      -0.0672229000
_diffrn_orient_matrix_UB_31      -0.0427629000
_diffrn_orient_matrix_UB_32      0.1756420000
_diffrn_orient_matrix_UB_33      -0.0308917000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.983
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              25
_reflns_limit_l_min              -25
_reflns_number_gt                1542
_reflns_number_total             1720
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_refine_diff_density_max         0.1688
_refine_diff_density_min         -0.1871
_refine_diff_density_rms         0.0416
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_d_res_high            0.8114
_refine_ls_d_res_low             10.3499
_refine_ls_goodness_of_fit_ref   1.0944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.0944
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0776P)²+0.0322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1189
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c)
;
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_refinement_flags_posn
C5 C -0.0570(3) -0.2100(3) -0.24616(8) 0.0461(4) Uani 1.000000 .
H5 H 0.0848(3) -0.2666(3) -0.23315(8) 0.0553(5) Uiso 1.000000 R
C6 C -0.1238(3) -0.2085(2) -0.31086(8) 0.0433(4) Uani 1.000000 .
H6 H -0.0271(3) -0.2648(2) -0.34112(8) 0.0519(5) Uiso 1.000000 R
C2 C -0.4788(3) -0.0408(2) -0.28504(9) 0.0475(4) Uani 1.000000 .
H2 H -0.6203(3) 0.0164(2) -0.29798(9) 0.0570(5) Uiso 1.000000 R
N10 N -0.3218(4) -0.0373(3) -0.51369(7) 0.0606(5) Uani 1.000000 .
C3 C -0.4132(4) -0.0432(2) -0.22039(8) 0.0504(4) Uani 1.000000 .
H3 H -0.5111(4) 0.0116(2) -0.19000(8) 0.0605(5) Uiso 1.000000 R
C8 C -0.4060(4) -0.1270(3) -0.39976(9) 0.0481(4) Uani 1.000000 .
H8 H -0.4106(4) -0.2398(3) -0.41976(9) 0.0577(5) Uiso 1.000000 R
C1 C -0.3344(3) -0.1232(2) -0.33055(8) 0.0406(4) Uani 1.000000 .
C4 C -0.2016(4) -0.1272(2) -0.20099(8) 0.0461(4) Uani 1.000000 .
H4 H -0.1568(4) -0.1280(2) -0.15763(8) 0.0553(5) Uiso 1.000000 R
O12 O -0.1464(4) 0.0178(3) -0.54252(7) 0.0810(5) Uani 1.000000 .
O7 O -0.5903(3) -0.0093(2) -0.42178(7) 0.0617(4) Uani 1.000000 .
O11 O -0.4738(4) -0.1339(3) -0.53645(8) 0.0952(7) Uani 1.000000 .
C13 C -0.2128(4) 0.1711(3) -0.42680(9) 0.0586(5) Uani 1.000000 .
H13a H -0.262(2) 0.2615(6) -0.4551(5) 0.0703(6) Uiso 1.000000 GR
H13b H -0.248(2) 0.2023(11) -0.3829(3) 0.0703(6) Uiso 1.000000 GR
H13c H -0.0395(5) 0.1506(6) -0.4316(7) 0.0703(6) Uiso 1.000000 GR
C9 C -0.3515(4) 0.0144(3) -0.44353(8) 0.0480(4) Uani 1.000000 .


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
C5 C6 1.388(2) . ?
C5 C4 1.384(3) . ?
C6 C1 1.387(2) . ?
C2 C3 1.385(3) . ?
C2 C1 1.387(2) . ?
N10 O12 1.205(3) . ?
N10 O11 1.217(3) . ?
N10 C9 1.517(2) . ?
C3 C4 1.385(3) . ?
C8 C1 1.485(2) . ?
C8 O7 1.438(2) . ?
C8 C9 1.466(3) . ?
O7 C9 1.385(3) . ?
C13 C9 1.486(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 C6 119.99(17) . . ?
C1 C6 C5 120.21(16) . . ?
C1 C2 C3 120.29(16) . . ?
O11 N10 O12 124.70(18) . . ?
C9 N10 O12 117.48(18) . . ?
C9 N10 O11 117.80(19) . . ?
C4 C3 C2 120.01(16) . . ?
O7 C8 C1 118.35(16) . . ?
C9 C8 C1 121.86(15) . . ?
C9 C8 O7 56.98(12) . . ?
C2 C1 C6 119.53(15) . . ?
C8 C1 C6 119.31(16) . . ?
C8 C1 C2 121.12(16) . . ?
C3 C4 C5 119.97(16) . . ?
C9 O7 C8 62.52(13) . . ?
C8 C9 N10 114.14(16) . . ?
O7 C9 N10 111.98(15) . . ?
O7 C9 C8 60.50(13) . . ?
C13 C9 N10 113.09(17) . . ?
C13 C9 C8 126.09(15) . . ?
C13 C9 O7 120.70(17) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 5 6 0.0412 -0.0050 5.0070 5.9744 0.2545 -0.7813 0.6951
1 -4 8 0.1012 1.0072 -3.9850 8.0163 0.1758 -0.1844 -0.9906
0 -5 -3 0.0687 0.0056 -5.0022 -2.9752 -0.2301 0.5794 -0.7869
-1 5 -6 0.0929 -1.0081 4.9876 -6.0216 -0.1184 -0.0258 1.1052
-3 -1 0 0.0332 -3.0002 -1.0008 0.0074 -0.8679 -0.0812 -0.0477
3 1 0 0.0484 3.0002 1.0008 -0.0074 0.8679 0.0812 0.0477
3 -2 4 0.0677 3.0049 -1.9914 4.0060 0.7769 0.0384 -0.6020
0 -5 5 0.0887 0.0074 -4.9896 5.0227 -0.1653 0.0409 -1.0319
3 -1 -5 0.0587 3.0017 -1.0061 -4.9964 0.7451 0.5687 -0.1507
-3 -2 8 0.0914 -2.9973 -1.9877 8.0101 -0.8443 -0.5442 -0.4684
1 -1 -12 0.0997 0.9992 -1.0180 -11.9929 0.1372 0.9355 0.1490
-3 -3 -5 0.0600 -2.9988 -3.0077 -4.9817 -0.9908 0.4064 -0.2461
-3 2 3 0.0438 -3.0034 2.0024 2.9922 -0.7201 -0.5095 0.3877
3 0 6 0.0715 3.0028 0.0107 5.9958 0.8754 -0.2472 -0.3117

_olex2_submission_original_sample_id Str1708
_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_str1709
_database_code_depnum_ccdc_archive 'CCDC 1455127'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;
_audit_creation_date             2014-09-30
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        (2S,3R)-2-nitro-2,3-diphenyloxirane
_chemical_formula_moiety         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H11 N O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.6028(3)
_cell_length_b                   6.2292(3)
_cell_length_c                   11.4861(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.415(3)
_cell_angle_gamma                90.00
_cell_volume                     613.70(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4210
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      71.1810
_cell_measurement_theta_min      3.8500
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.5590
_exptl_crystal_size_mid          0.1000
_exptl_crystal_size_min          0.0726
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9996
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.00
_diffrn_reflns_theta_min         3.86
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9552
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -130.00  -35.80   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307 -178.0000   90.0000 157

#__ type_ start__ end____ width___ exp.time_
  2 omega -116.00   -5.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000  -30.0000 185

#__ type_ start__ end____ width___ exp.time_
  3 omega -122.00   19.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -19.0000   60.0000 235

#__ type_ start__ end____ width___ exp.time_
  4 omega -122.00   -2.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -77.0000  -90.0000 200

#__ type_ start__ end____ width___ exp.time_
  5 omega  -40.00   69.20   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307  -57.0000 -120.0000 182

#__ type_ start__ end____ width___ exp.time_
  6 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000  -30.0000 177

#__ type_ start__ end____ width___ exp.time_
  7 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000  -60.0000 177

#__ type_ start__ end____ width___ exp.time_
  8 omega   76.00  178.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  -60.0000 170

#__ type_ start__ end____ width___ exp.time_
  9 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -60.0000 172

#__ type_ start__ end____ width___ exp.time_
 10 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000 -120.0000 172

#__ type_ start__ end____ width___ exp.time_
 11 omega   76.00  178.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000   30.0000 170

#__ type_ start__ end____ width___ exp.time_
 12 omega   28.00   97.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000   30.0000 115

#__ type_ start__ end____ width___ exp.time_
 13 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -30.0000 172

#__ type_ start__ end____ width___ exp.time_
 14 omega   20.00  108.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000 -120.0000 147

#__ type_ start__ end____ width___ exp.time_
 15 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000  -90.0000 177

#__ type_ start__ end____ width___ exp.time_
 16 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000 -120.0000 177

#__ type_ start__ end____ width___ exp.time_
 17 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -90.0000 172

#__ type_ start__ end____ width___ exp.time_
 18 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000    0.0000 172

#__ type_ start__ end____ width___ exp.time_
 19 omega   76.00  178.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  -30.0000 170

#__ type_ start__ end____ width___ exp.time_
 20 omega   26.00   89.60   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
 21 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000    0.0000 177

#__ type_ start__ end____ width___ exp.time_
 22 omega   25.00  115.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524 -111.0000   60.0000 150

#__ type_ start__ end____ width___ exp.time_
 23 omega -116.00   -5.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000 -120.0000 185

#__ type_ start__ end____ width___ exp.time_
 24 omega -122.00   -2.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -77.0000   90.0000 200

#__ type_ start__ end____ width___ exp.time_
 25 omega  -49.00   41.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307   37.0000  150.0000 150

#__ type_ start__ end____ width___ exp.time_
 26 omega -116.00   -5.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000  150.0000 185

#__ type_ start__ end____ width___ exp.time_
 27 omega  -49.00   41.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307   37.0000    0.0000 150

#__ type_ start__ end____ width___ exp.time_
 28 omega   57.00  129.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307  178.0000  150.0000 120

#__ type_ start__ end____ width___ exp.time_
 29 omega    2.00  122.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307   77.0000 -180.0000 200

#__ type_ start__ end____ width___ exp.time_
 30 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000 -180.0000 177

#__ type_ start__ end____ width___ exp.time_
 31 omega   28.00   97.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000 -120.0000 115

#__ type_ start__ end____ width___ exp.time_
 32 omega   71.00  122.60   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   65.0000   61.8081 86

#__ type_ start__ end____ width___ exp.time_
 33 omega   26.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   15.0000 -180.0000 252
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0211234000
_diffrn_orient_matrix_UB_12      0.0730286000
_diffrn_orient_matrix_UB_13      -0.1259404000
_diffrn_orient_matrix_UB_21      -0.1709302000
_diffrn_orient_matrix_UB_22      -0.0591214000
_diffrn_orient_matrix_UB_23      -0.0357228000
_diffrn_orient_matrix_UB_31      -0.0509226000
_diffrn_orient_matrix_UB_32      0.2287035000
_diffrn_orient_matrix_UB_33      0.0311436000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1941
_reflns_number_total             2130
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1023P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1369
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O9 O -0.94886(19) -0.4701(3) -0.78273(16) 0.0417(5) Uani 1 1 d . . .
O18 O -0.84012(19) -0.5662(4) -1.06363(13) 0.0447(4) Uani 1 1 d . . .
O17 O -1.06991(18) -0.5621(4) -0.99943(16) 0.0487(5) Uani 1 1 d . . .
N16 N -0.9281(2) -0.5648(4) -0.98430(15) 0.0360(4) Uani 1 1 d . . .
C15 C -0.6280(3) -0.3294(5) -0.81490(19) 0.0400(5) Uani 1 1 d . . .
H15 H -0.6984 -0.2193 -0.7963 0.048 Uiso 1 1 calc R . .
C7 C -0.9423(3) -0.7029(4) -0.7802(2) 0.0368(5) Uani 1 1 d . . .
C10 C -0.6839(2) -0.5298(4) -0.85075(18) 0.0344(6) Uani 1 1 d . . .
C1 C -0.8712(3) -0.8135(5) -0.67362(19) 0.0419(6) Uani 1 1 d . . .
C14 C -0.4690(3) -0.2910(5) -0.8065(2) 0.0473(6) Uani 1 1 d . . .
H14 H -0.4302 -0.1541 -0.7821 0.057 Uiso 1 1 calc R . .
C13 C -0.3665(3) -0.4513(6) -0.8334(2) 0.0502(7) Uani 1 1 d . . .
H13 H -0.2574 -0.4245 -0.8270 0.060 Uiso 1 1 calc R . .
C11 C -0.5811(3) -0.6901(5) -0.8782(2) 0.0424(6) Uani 1 1 d . . .
H11 H -0.6190 -0.8272 -0.9030 0.051 Uiso 1 1 calc R . .
C8 C -0.8537(2) -0.5714(5) -0.85874(17) 0.0337(5) Uani 1 1 d . . .
C2 C -0.9275(4) -1.0135(5) -0.6487(2) 0.0494(7) Uani 1 1 d . . .
H2 H -1.0081 -1.0761 -0.6987 0.059 Uiso 1 1 calc R . .
C12 C -0.4217(3) -0.6481(5) -0.8690(2) 0.0495(7) Uani 1 1 d . . .
H12 H -0.3507 -0.7573 -0.8877 0.059 Uiso 1 1 calc R . .
C6 C -0.7532(4) -0.7210(6) -0.6007(2) 0.0561(8) Uani 1 1 d . . .
H6 H -0.7144 -0.5824 -0.6174 0.067 Uiso 1 1 calc R . .
C3 C -0.8667(4) -1.1246(6) -0.5503(3) 0.0649(9) Uani 1 1 d . . .
H3 H -0.9064 -1.2621 -0.5326 0.078 Uiso 1 1 calc R . .
C5 C -0.6926(4) -0.8342(8) -0.5030(3) 0.0748(11) Uani 1 1 d . . .
H5 H -0.6118 -0.7728 -0.4527 0.090 Uiso 1 1 calc R . .
C4 C -0.7492(5) -1.0346(8) -0.4789(3) 0.0751(11) Uani 1 1 d . . .
H4 H -0.7066 -1.1112 -0.4124 0.090 Uiso 1 1 calc R . .
H7 H -1.044(3) -0.765(4) -0.8180(19) 0.024(5) Uiso 1 1 d . . .


_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
O9 C7 1.451(3) . ?
O9 C8 1.393(3) . ?
O18 N16 1.228(2) . ?
O17 N16 1.219(2) . ?
N16 C8 1.533(3) . ?
C15 C10 1.389(4) . ?
C15 C14 1.385(3) . ?
C7 C1 1.494(4) . ?
C7 C8 1.474(3) . ?
C10 C11 1.386(4) . ?
C10 C8 1.479(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.390(4) . ?
C14 C13 1.383(4) . ?
C13 C12 1.366(5) . ?
C11 C12 1.392(4) . ?
C2 C3 1.392(4) . ?
C6 C5 1.392(5) . ?
C3 C4 1.371(6) . ?
C5 C4 1.376(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O9 C7 62.38(17) . . ?
O18 N16 C8 117.48(17) . . ?
O17 N16 O18 124.14(17) . . ?
O17 N16 C8 118.37(16) . . ?
C14 C15 C10 119.6(2) . . ?
O9 C7 C1 119.4(2) . . ?
O9 C7 C8 56.87(16) . . ?
C8 C7 C1 124.04(19) . . ?
C15 C10 C8 119.5(2) . . ?
C11 C10 C15 120.2(2) . . ?
C11 C10 C8 120.3(2) . . ?
C2 C1 C7 117.4(2) . . ?
C2 C1 C6 120.2(3) . . ?
C6 C1 C7 122.4(3) . . ?
C13 C14 C15 120.2(3) . . ?
C12 C13 C14 120.1(2) . . ?
C10 C11 C12 119.3(3) . . ?
O9 C8 N16 110.79(17) . . ?
O9 C8 C7 60.76(15) . . ?
O9 C8 C10 120.47(19) . . ?
C7 C8 N16 113.14(19) . . ?
C7 C8 C10 127.86(19) . . ?
C10 C8 N16 113.11(16) . . ?
C1 C2 C3 120.2(3) . . ?
C13 C12 C11 120.6(3) . . ?
C1 C6 C5 119.1(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C5 C6 120.4(3) . . ?
C3 C4 C5 120.4(3) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5 0 2 0.0517 5.0011 -0.0037 1.9936 -0.1457 -0.9258 -0.1934
-5 0 -2 0.0483 -5.0011 0.0037 -1.9936 0.1457 0.9258 0.1934
-4 -2 -3 0.1127 -4.0039 -1.9977 -2.9927 0.1464 0.9094 -0.3462
5 1 -2 0.0524 5.0035 0.9965 -2.0042 0.4309 -0.8426 -0.0893
-5 0 3 0.0462 -5.0021 0.0039 3.0029 -0.4836 0.7475 0.3491
-5 -2 2 0.1099 -5.0052 -1.9968 2.0048 -0.5040 0.9020 -0.1394
5 -1 -3 0.1479 5.0005 -1.0042 -3.0023 0.4104 -0.6881 -0.5778
2 1 -7 0.0472 2.0036 0.9985 -6.9978 0.9965 -0.1515 -0.0916
2 -1 -7 0.1137 2.0004 -1.0021 -6.9965 0.8502 -0.0327 -0.5489
-2 -1 7 0.0254 -2.0036 -0.9985 6.9978 -0.9965 0.1515 0.0916
-2 0 7 0.0349 -2.0020 0.0018 6.9972 -0.9234 0.0921 0.3203
2 1 7 0.0511 2.0008 0.9991 6.9925 -0.7654 -0.6509 0.3444
-3 0 -6 0.0581 -2.9997 0.0020 -5.9928 0.6915 0.7267 -0.0334

