# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2224489'
loop_
_audit_author_name
_audit_author_address
'Dongyan Jiang'
;Jilin university
China
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-01-10
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.01.06 svn.r734b3b31 for OlexSys, GUI svn.r6444)
;
_chemical_formula_moiety         'C10 H12 F N O'
_chemical_formula_sum            'C10 H12 F N O'
_chemical_formula_weight         181.211
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.8800(7)
_cell_length_b                   10.1316(7)
_cell_length_c                   10.6588(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.843(2)
_cell_angle_gamma                90
_cell_volume                     883.75(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.727
_cell_measurement_theta_min      2.889
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             384.282
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21899
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9984
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1740
_reflns_number_total             1869
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.0800
_refine_diff_density_min         -0.1078
_refine_diff_density_rms         0.0232
_refine_ls_d_res_high            0.7898
_refine_ls_d_res_low             7.0524
_refine_ls_goodness_of_fit_ref   1.2253
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0153
_refine_ls_R_factor_gt           0.0130
_refine_ls_restrained_S_all      1.2253
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0064P)²+0.0362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0284
_refine_ls_wR_factor_ref         0.0299
_olex2_refinement_description    
;
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2023-01-10_12-18-06
;
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
F001 F 0.97084(3) 0.63638(3) 0.93364(3) 0.02376(8) Uani 1.000000 .
O002 O 0.50172(4) 0.40303(3) 0.12878(3) 0.02063(8) Uani 1.000000 .
N003 N 0.70718(4) 0.52057(3) 0.38063(3) 0.01318(8) Uani 1.000000 .
C004 C 0.75424(5) 0.67257(4) 0.56916(4) 0.01406(9) Uani 1.000000 .
H004 H 0.6862(8) 0.7474(6) 0.4971(6) 0.0332(16) Uani 1.000000 .
C005 C 0.81738(5) 0.70209(4) 0.70746(4) 0.01503(9) Uani 1.000000 .
H005 H 0.7991(8) 0.7968(6) 0.7459(6) 0.0337(16) Uani 1.000000 .
C006 C 0.86725(5) 0.45283(4) 0.61844(4) 0.01459(9) Uani 1.000000 .
H006 H 0.8889(8) 0.3556(6) 0.5877(6) 0.0332(16) Uani 1.000000 .
C007 C 0.90617(5) 0.60613(4) 0.79896(4) 0.01566(9) Uani 1.000000 .
C008 C 0.77668(5) 0.54697(4) 0.52245(4) 0.01201(9) Uani 1.000000 .
C009 C 0.93251(5) 0.48235(4) 0.75768(4) 0.01616(9) Uani 1.000000 .
H009 H 1.0010(8) 0.4086(6) 0.8327(6) 0.0365(17) Uani 1.000000 .
C00A C 0.74309(6) 0.39098(5) 0.33888(5) 0.01660(10) Uani 1.000000 .
H00a H 0.8767(7) 0.3760(6) 0.3782(6) 0.0325(16) Uani 1.000000 .
H00b H 0.6885(8) 0.3116(6) 0.3778(6) 0.0370(16) Uani 1.000000 .
C00B C 0.53037(5) 0.54749(5) 0.31824(4) 0.01704(10) Uani 1.000000 .
H00c H 0.4645(7) 0.4784(7) 0.3602(6) 0.0378(17) Uani 1.000000 .
H00d H 0.5070(7) 0.6499(6) 0.3406(6) 0.0361(17) Uani 1.000000 .
C00C C 0.46606(6) 0.53113(5) 0.16499(5) 0.01894(10) Uani 1.000000 .
H00e H 0.5216(7) 0.6051(6) 0.1203(6) 0.0329(15) Uani 1.000000 .
H00f H 0.3329(8) 0.5409(7) 0.1212(6) 0.0398(17) Uani 1.000000 .
C00D C 0.67364(6) 0.38319(5) 0.18440(5) 0.02001(10) Uani 1.000000 .
H00g H 0.6936(8) 0.2840(7) 0.1500(6) 0.0430(18) Uani 1.000000 .
H00h H 0.7307(8) 0.4583(6) 0.1430(6) 0.0374(16) 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
F001 C007 1.3581(5) . ?
O002 C00C 1.4242(6) . ?
O002 C00D 1.4212(6) . ?
N003 C008 1.4188(5) . ?
N003 C00A 1.4608(5) . ?
N003 C00B 1.4735(6) . ?
C004 H004 1.082(6) . ?
C004 C005 1.3911(6) . ?
C004 C008 1.4085(6) . ?
C005 H005 1.080(6) . ?
C005 C007 1.3861(6) . ?
C006 H006 1.079(6) . ?
C006 C008 1.4016(6) . ?
C006 C009 1.4001(6) . ?
C007 C009 1.3787(6) . ?
C009 H009 1.091(6) . ?
C00A H00a 1.105(6) . ?
C00A H00b 1.100(6) . ?
C00A C00D 1.5196(6) . ?
C00B H00c 1.111(6) . ?
C00B H00d 1.102(6) . ?
C00B C00C 1.5157(6) . ?
C00C H00e 1.102(6) . ?
C00C H00f 1.094(6) . ?
C00D H00g 1.107(6) . ?
C00D H00h 1.098(6) . ?

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
C00D O002 C00C 109.37(3) . . ?
C00A N003 C008 115.97(3) . . ?
C00B N003 C008 113.11(3) . . ?
C00B N003 C00A 110.44(3) . . ?
C005 C004 H004 119.1(3) . . ?
C008 C004 H004 119.9(3) . . ?
C008 C004 C005 120.98(4) . . ?
H005 C005 C004 122.3(3) . . ?
C007 C005 C004 118.69(4) . . ?
C007 C005 H005 119.0(3) . . ?
C008 C006 H006 121.3(3) . . ?
C009 C006 H006 117.9(3) . . ?
C009 C006 C008 120.83(4) . . ?
C005 C007 F001 118.49(4) . . ?
C009 C007 F001 119.22(4) . . ?
C009 C007 C005 122.28(4) . . ?
C004 C008 N003 118.95(4) . . ?
C006 C008 N003 122.58(4) . . ?
C006 C008 C004 118.46(4) . . ?
C007 C009 C006 118.75(4) . . ?
H009 C009 C006 120.9(3) . . ?
H009 C009 C007 120.3(3) . . ?
H00a C00A N003 109.7(3) . . ?
H00b C00A N003 111.2(3) . . ?
H00b C00A H00a 108.8(5) . . ?
C00D C00A N003 109.39(4) . . ?
C00D C00A H00a 109.2(3) . . ?
C00D C00A H00b 108.5(3) . . ?
H00c C00B N003 109.7(3) . . ?
H00d C00B N003 109.5(3) . . ?
H00d C00B H00c 109.5(5) . . ?
C00C C00B N003 110.84(4) . . ?
C00C C00B H00c 109.1(3) . . ?
C00C C00B H00d 108.2(3) . . ?
C00B C00C O002 111.18(4) . . ?
H00e C00C O002 108.5(3) . . ?
H00e C00C C00B 110.3(3) . . ?
H00f C00C O002 106.5(3) . . ?
H00f C00C C00B 110.0(3) . . ?
H00f C00C H00e 110.2(5) . . ?
C00A C00D O002 111.29(4) . . ?
H00g C00D O002 105.9(3) . . ?
H00g C00D C00A 110.8(3) . . ?
H00h C00D O002 108.9(3) . . ?
H00h C00D C00A 110.1(3) . . ?
H00h C00D H00g 109.7(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C004 H004 O002 1.082(6) 2.309(6) 3.3684(6) 165.8(5) 2_655
C005 H005 N003 1.080(6) 2.658(6) 3.6963(6) 161.1(5) 4_576
C006 H006 F001 1.079(6) 2.599(6) 3.6434(6) 162.7(5) 2_746
C009 H009 F001 1.091(6) 2.448(6) 3.2888(6) 132.9(4) 3_767
C00B H00d O002 1.102(6) 2.590(6) 3.6744(6) 167.6(5) 2_655
C00C H00e O002 1.102(6) 2.582(6) 3.3208(6) 123.5(4) 3_665

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
F001 C007 C005 C004 178.48(4) . . . . ?
F001 C007 C009 C006 -179.10(4) . . . . ?
O002 C00C C00B N003 56.19(4) . . . . ?
O002 C00D C00A N003 -59.44(4) . . . . ?
N003 C008 C004 C005 178.73(4) . . . . ?
N003 C008 C006 C009 -179.37(4) . . . . ?
C004 C005 C007 C009 -0.65(5) . . . . ?
C004 C008 C006 C009 0.67(5) . . . . ?
C005 C007 C009 C006 0.03(5) . . . . ?


_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_3
_database_code_depnum_ccdc_archive 'CCDC 2224504'
loop_
_audit_author_name
_audit_author_address
'Dongyan Jiang'
;Jilin university
China
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 I N O'
_chemical_formula_sum            'C10 H12 I N O'
_chemical_formula_weight         289.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0417(7)
_cell_length_b                   8.8995(11)
_cell_length_c                   11.5534(14)
_cell_angle_alpha                77.659(5)
_cell_angle_beta                 83.631(5)
_cell_angle_gamma                89.288(5)
_cell_volume                     503.25(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4198
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      21.015
_cell_measurement_theta_min      4.670
_shelx_estimated_absorpt_T_max   0.744
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    3.141
_exptl_absorpt_correction_T_max  0.746742
_exptl_absorpt_correction_T_min  0.584358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0957 before and 0.0791 after correction.
 The Ratio of minimum to maximum transmission is 0.78.

Final HKLF 4 output contains 62289 reflections, Rint = 0.2079
 (10066 with I > 3sig(I), Rint = 0.0821)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1715
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.640
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1491
_reflns_number_total             1715
_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       'Bruker D8 Venture diffractrometer'
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.558
_refine_diff_density_min         -1.196
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         1715
_refine_ls_number_restraints     282
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.010
_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)+(0.0447P)²+5.2342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_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. Uiso/Uaniso restraints and constraints
N1 \\sim O1 \\sim C9 \\sim C7 \\sim C8 \\sim C10 \\sim N1A \\sim C7A \\sim C8A
\\sim O1A \\sim C9A \\sim C10A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C2A) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C7, O1, C9, N1, C8, C10, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C10A, O1A, C8A, N1A, C9A, C7A, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=1-
 FVAR(1)
 Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=FVAR(1)
 Sof(N1A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(O1A)=
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=1-FVAR(2)
 Sof(N1)=Sof(O1)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C7A(H7AA,H7AB),
 C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10C,H10D)
5.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C2(H2), C6A(H6A), C3(H3), C5(H5), C6(H6), C2A(H2A), C3A(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 1.04189(12) 0.25440(6) 0.18077(4) 0.0321(2) Uani 1 1 d . . . . .
N1 N 0.598(4) 0.248(3) 0.7218(16) 0.021(3) Uani 0.501(10) 1 d . U P A 1
O1 O 0.357(3) 0.2142(17) 0.9464(12) 0.026(2) Uani 0.501(10) 1 d . U P A 1
C1 C 0.8783(15) 0.2549(8) 0.3565(6) 0.0209(16) Uani 1 1 d . . . . .
C4 C 0.6730(14) 0.2542(9) 0.5920(7) 0.0241(16) Uani 1 1 d . . . . .
C9 C 0.450(4) 0.381(2) 0.8810(17) 0.025(3) Uani 0.501(10) 1 d . U P A 1
H9A H 0.309361 0.454665 0.897175 0.030 Uiso 0.501(10) 1 calc R U P A 1
H9B H 0.613448 0.408137 0.912488 0.030 Uiso 0.501(10) 1 calc R U P A 1
C7 C 0.344(4) 0.141(2) 0.7585(16) 0.024(3) Uani 0.501(10) 1 d . U P A 1
H7A H 0.362734 0.044089 0.729560 0.029 Uiso 0.501(10) 1 calc R U P A 1
H7B H 0.177198 0.193730 0.735720 0.029 Uiso 0.501(10) 1 calc R U P A 1
C8 C 0.378(3) 0.1159(19) 0.9150(13) 0.025(2) Uani 0.501(10) 1 d . U P A 1
H8A H 0.242096 0.040010 0.960520 0.030 Uiso 0.501(10) 1 calc R U P A 1
H8B H 0.555742 0.072599 0.929755 0.030 Uiso 0.501(10) 1 calc R U P A 1
C10 C 0.505(3) 0.3931(17) 0.7505(13) 0.023(2) Uani 0.501(10) 1 d . U P A 1
H10A H 0.339933 0.423875 0.712813 0.028 Uiso 0.501(10) 1 calc R U P A 1
H10B H 0.641730 0.474276 0.717294 0.028 Uiso 0.501(10) 1 calc R U P A 1
C5A C 0.712(3) 0.3866(18) 0.5144(14) 0.029(4) Uani 0.515(10) 1 d . . P A 2
H5A H 0.675829 0.480686 0.538972 0.035 Uiso 0.515(10) 1 calc R U P A 2
C2 C 0.625(3) 0.2133(17) 0.3913(14) 0.023(4) Uani 0.485(10) 1 d . U P A 1
H2 H 0.520090 0.182849 0.336534 0.028 Uiso 0.485(10) 1 calc R U P A 1
C6A C 0.808(3) 0.3874(18) 0.3965(13) 0.030(4) Uani 0.515(10) 1 d . . P A 2
H6A H 0.825904 0.483230 0.341016 0.035 Uiso 0.515(10) 1 calc R U P A 2
C3 C 0.516(3) 0.2134(17) 0.5004(13) 0.019(3) Uani 0.485(10) 1 d . . P A 1
H3 H 0.331957 0.186826 0.521501 0.023 Uiso 0.485(10) 1 calc R U P A 1
C5 C 0.922(3) 0.2977(17) 0.5481(13) 0.021(4) Uani 0.485(10) 1 d . . P A 1
H5 H 1.028662 0.331263 0.600645 0.025 Uiso 0.485(10) 1 calc R U P A 1
C6 C 1.045(3) 0.2996(16) 0.4311(14) 0.023(4) Uani 0.485(10) 1 d . . P A 1
H6 H 1.226128 0.328975 0.406070 0.027 Uiso 0.485(10) 1 calc R U P A 1
C2A C 0.839(3) 0.1131(16) 0.4432(14) 0.026(4) Uani 0.515(10) 1 d . U P A 2
H2A H 0.872441 0.018316 0.419246 0.031 Uiso 0.515(10) 1 calc R U P A 2
C3A C 0.752(3) 0.1125(18) 0.5613(14) 0.027(4) Uani 0.515(10) 1 d . . P A 2
H3A H 0.746032 0.019747 0.620281 0.033 Uiso 0.515(10) 1 calc R U P A 2
N1A N 0.535(4) 0.263(2) 0.6989(16) 0.020(3) Uani 0.499(10) 1 d . U P A 2
C7A C 0.699(3) 0.2996(17) 0.7836(13) 0.023(2) Uani 0.499(10) 1 d . U P A 2
H7AA H 0.816671 0.388259 0.744438 0.027 Uiso 0.499(10) 1 calc R U P A 2
H7AB H 0.813020 0.210667 0.810748 0.027 Uiso 0.499(10) 1 calc R U P A 2
C8A C 0.530(4) 0.338(2) 0.8910(17) 0.024(3) Uani 0.499(10) 1 d . U P A 2
H8AA H 0.496396 0.450327 0.871828 0.029 Uiso 0.499(10) 1 calc R U P A 2
H8AB H 0.641008 0.319196 0.958078 0.029 Uiso 0.499(10) 1 calc R U P A 2
O1A O 0.261(3) 0.2574(16) 0.9367(12) 0.028(2) Uani 0.499(10) 1 d . U P A 2
C9A C 0.186(3) 0.1866(18) 0.8674(13) 0.025(2) Uani 0.499(10) 1 d . U P A 2
H9AA H 0.078491 0.256089 0.812666 0.030 Uiso 0.499(10) 1 calc R U P A 2
H9AB H 0.067656 0.101621 0.913202 0.030 Uiso 0.499(10) 1 calc R U P A 2
C10A C 0.427(4) 0.112(2) 0.7855(16) 0.024(3) Uani 0.499(10) 1 d . U P A 2
H10C H 0.565533 0.060730 0.834156 0.029 Uiso 0.499(10) 1 calc R U P A 2
H10D H 0.354997 0.039430 0.742662 0.029 Uiso 0.499(10) 1 calc R U P A 2


_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
I1 C1 2.106(7) . ?
N1 C4 1.49(2) . ?
N1 C7 1.57(3) . ?
N1 C10 1.46(3) . ?
O1 C9 1.57(2) . ?
O1 C8 1.02(2) . ?
C1 C2 1.330(17) . ?
C1 C6A 1.384(18) . ?
C1 C6 1.386(18) . ?
C1 C2A 1.434(15) . ?
C4 C5A 1.321(17) . ?
C4 C3 1.496(16) . ?
C4 C5 1.329(17) . ?
C4 C3A 1.423(17) . ?
C4 N1A 1.37(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.48(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.80(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.39(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.32(2) . ?
C6A H6A 0.9500 . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.42(2) . ?
C6 H6 0.9500 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.38(2) . ?
C3A H3A 0.9500 . ?
N1A C7A 1.44(2) . ?
N1A C10A 1.56(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.52(2) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A O1A 1.53(2) . ?
O1A C9A 1.21(2) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.67(2) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?

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 N1 C7 105.6(15) . . ?
C10 N1 C4 115.0(14) . . ?
C10 N1 C7 103.1(15) . . ?
C8 O1 C9 128.0(16) . . ?
C2 C1 I1 119.7(8) . . ?
C2 C1 C6 123.0(10) . . ?
C6A C1 I1 123.6(7) . . ?
C6A C1 C2A 116.1(10) . . ?
C6 C1 I1 117.3(7) . . ?
C2A C1 I1 120.3(8) . . ?
N1 C4 C3 130.7(11) . . ?
C5A C4 C3A 121.4(11) . . ?
C5A C4 N1A 115.1(13) . . ?
C5 C4 N1 116.8(11) . . ?
C5 C4 C3 112.5(10) . . ?
N1A C4 C3A 123.3(12) . . ?
O1 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 O1 111.2(15) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N1 C7 H7A 113.2 . . ?
N1 C7 H7B 113.2 . . ?
N1 C7 C8 92.5(13) . . ?
H7A C7 H7B 110.6 . . ?
C8 C7 H7A 113.2 . . ?
C8 C7 H7B 113.2 . . ?
O1 C8 C7 114.2(15) . . ?
O1 C8 H8A 108.7 . . ?
O1 C8 H8B 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N1 C10 C9 111.9(14) . . ?
N1 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C4 C5A H5A 120.2 . . ?
C4 C5A C6A 119.7(15) . . ?
C6A C5A H5A 120.2 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(14) . . ?
C3 C2 H2 119.4 . . ?
C1 C6A C5A 123.0(13) . . ?
C1 C6A H6A 118.5 . . ?
C5A C6A H6A 118.5 . . ?
C4 C3 H3 119.1 . . ?
C2 C3 C4 121.8(13) . . ?
C2 C3 H3 119.1 . . ?
C4 C5 H5 116.5 . . ?
C4 C5 C6 127.0(13) . . ?
C6 C5 H5 116.5 . . ?
C1 C6 C5 114.4(12) . . ?
C1 C6 H6 122.8 . . ?
C5 C6 H6 122.8 . . ?
C1 C2A H2A 119.6 . . ?
C3A C2A C1 120.9(13) . . ?
C3A C2A H2A 119.6 . . ?
C4 C3A H3A 120.8 . . ?
C2A C3A C4 118.3(13) . . ?
C2A C3A H3A 120.8 . . ?
C4 N1A C7A 113.9(14) . . ?
C4 N1A C10A 118.7(18) . . ?
C7A N1A C10A 92.5(14) . . ?
N1A C7A H7AA 109.3 . . ?
N1A C7A H7AB 109.3 . . ?
N1A C7A C8A 111.4(14) . . ?
H7AA C7A H7AB 108.0 . . ?
C8A C7A H7AA 109.3 . . ?
C8A C7A H7AB 109.3 . . ?
C7A C8A H8AA 107.3 . . ?
C7A C8A H8AB 107.3 . . ?
C7A C8A O1A 120.2(16) . . ?
H8AA C8A H8AB 106.9 . . ?
O1A C8A H8AA 107.3 . . ?
O1A C8A H8AB 107.3 . . ?
C9A O1A C8A 112.5(15) . . ?
O1A C9A H9AA 108.3 . . ?
O1A C9A H9AB 108.3 . . ?
O1A C9A C10A 115.8(14) . . ?
H9AA C9A H9AB 107.4 . . ?
C10A C9A H9AA 108.3 . . ?
C10A C9A H9AB 108.3 . . ?
N1A C10A C9A 98.9(15) . . ?
N1A C10A H10C 112.0 . . ?
N1A C10A H10D 112.0 . . ?
C9A C10A H10C 112.0 . . ?
C9A C10A H10D 112.0 . . ?
H10C C10A H10D 109.7 . . ?

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
I1 C1 C2 C3 -179.5(11) . . . . ?
I1 C1 C6A C5A -176.7(11) . . . . ?
I1 C1 C6 C5 179.8(10) . . . . ?
I1 C1 C2A C3A 174.6(11) . . . . ?
N1 C4 C3 C2 -173.9(15) . . . . ?
N1 C4 C5 C6 174.3(15) . . . . ?
N1 C7 C8 O1 63.9(19) . . . . ?
O1 C9 C10 N1 -31(2) . . . . ?
C1 C2 C3 C4 -2(2) . . . . ?
C1 C2A C3A C4 7(2) . . . . ?
C4 N1 C7 C8 163.8(11) . . . . ?
C4 N1 C10 C9 -176.6(14) . . . . ?
C4 C5A C6A C1 -3(2) . . . . ?
C4 C5 C6 C1 2(2) . . . . ?
C4 N1A C7A C8A 169.2(15) . . . . ?
C4 N1A C10A C9A -158.5(13) . . . . ?
C9 O1 C8 C7 -36(3) . . . . ?
C7 N1 C4 C3 17(2) . . . . ?
C7 N1 C4 C5 -160.2(13) . . . . ?
C7 N1 C10 C9 69.0(17) . . . . ?
C8 O1 C9 C10 17(3) . . . . ?
C10 N1 C4 C3 -95.6(19) . . . . ?
C10 N1 C4 C5 86.8(16) . . . . ?
C10 N1 C7 C8 -75.1(14) . . . . ?
C5A C4 C3A C2A -8.8(19) . . . . ?
C5A C4 N1A C7A -85.3(17) . . . . ?
C5A C4 N1A C10A 167.5(14) . . . . ?
C2 C1 C6 C5 -0.2(18) . . . . ?
C6A C1 C2A C3A -4.2(18) . . . . ?
C3 C4 C5 C6 -4(2) . . . . ?
C5 C4 C3 C2 3.9(18) . . . . ?
C6 C1 C2 C3 1(2) . . . . ?
C2A C1 C6A C5A 2.0(19) . . . . ?
C3A C4 C5A C6A 7(2) . . . . ?
C3A C4 N1A C7A 99.5(18) . . . . ?
C3A C4 N1A C10A -8(2) . . . . ?
N1A C4 C5A C6A -168.6(14) . . . . ?
N1A C4 C3A C2A 166.2(14) . . . . ?
N1A C7A C8A O1A 34(2) . . . . ?
C7A N1A C10A C9A 82.5(14) . . . . ?
C7A C8A O1A C9A -12(2) . . . . ?
C8A O1A C9A C10A 32(2) . . . . ?
O1A C9A C10A N1A -72.9(18) . . . . ?
C10A N1A C7A C8A -67.8(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT881_3                   
;
PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do !
RESPONSE: Heavily disordered twinned structure.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2224534'
loop_
_audit_author_name
_audit_author_address
'Dongyan Jiang'
;Jilin university
China
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 Br N O'
_chemical_formula_sum            'C10 H12 Br N O'
_chemical_formula_weight         242.12
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   9.9421(7)
_cell_length_b                   10.1035(8)
_cell_length_c                   10.6866(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.715(3)
_cell_angle_gamma                90
_cell_volume                     1010.54(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9751
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.689
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    4.027
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0858 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.6824.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23834
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.857
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                3582
_reflns_number_total             4317
_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 V8.40A (?, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     53
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.024
_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)+(0.0080P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0479
_refine_ls_wR_factor_ref         0.0511
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-C10A \\sim N1-C7 \\sim N1-C7A \\sim N1-C10
 with sigma of 0.02
 O1A-C9A \\sim O1-C8 \\sim O1A-C8A \\sim O1-C9
 with sigma of 0.02
 C9A-C10A \\sim C8-C7 \\sim C8A-C7A \\sim C9-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O1)
Uanis(C10A) = Uanis(C7) = Uanis(C9A) = Uanis(C8) = Uanis(C9) = Uanis(C8A) =
Uanis(C10) = Uanis(C7A)
4. Same fragment restrains
{N2, C20, C19, O2, C18, C17} sigma for 1-2: 0.02, 1-3: 0.02
as
{N1, C10, C9, O1, C8, C7}
5. Others
 Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(O1A)=Sof(C8A)=
 Sof(H8AA)=Sof(H8AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=1-FVAR(1)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(O1)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(C7)=Sof(H7A)=Sof(H7B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B), C7(H7A,H7B), C17(H17A,H17B),
 C19(H19A,H19B), C20(H20A,H20B), C18(H18A,H18B), C10A(H10C,H10D), C9A(H9AA,
 H9AB), C8A(H8AA,H8AB), C7A(H7AA,H7AB)
6.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C13(H13), C5(H5), C2(H2), C3(H3), C15(H15), C6(H6)
;
_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
Br2 Br 0.46589(3) 0.38982(4) 0.20037(3) 0.05904(13) Uani 1 1 d . . . . .
Br1 Br -0.22691(4) 0.12196(5) 0.03549(4) 0.06947(18) Uani 1 1 d . . . . .
N2 N 0.9908(3) 0.3983(3) 0.7057(3) 0.0432(7) Uani 1 1 d D . . . .
C12 C 0.6480(4) 0.4927(4) 0.4491(4) 0.0527(9) Uani 1 1 d . . . . .
H12 H 0.580679 0.560080 0.433646 0.063 Uiso 1 1 calc R . . . .
C16 C 0.7281(4) 0.2920(4) 0.3807(4) 0.0547(9) Uani 1 1 d . . . . .
H16 H 0.715903 0.224473 0.318657 0.066 Uiso 1 1 calc R . . . .
O2 O 1.1980(3) 0.3470(3) 0.9589(3) 0.0695(8) Uani 1 1 d D . . . .
C13 C 0.7658(4) 0.4937(4) 0.5631(4) 0.0500(9) Uani 1 1 d . . . . .
H13 H 0.777714 0.562834 0.623313 0.060 Uiso 1 1 calc R . . . .
N1 N 0.3171(4) 0.1094(3) 0.5204(4) 0.0646(10) Uani 1 1 d D . . . .
C10 C 0.4012(9) 0.2260(9) 0.5505(11) 0.0717(13) Uani 0.691(16) 1 d D . P A 1
H10A H 0.353965 0.291463 0.587585 0.086 Uiso 0.691(16) 1 calc R . P A 1
H10B H 0.409362 0.261990 0.469248 0.086 Uiso 0.691(16) 1 calc R . P A 1
C9 C 0.5469(9) 0.1999(9) 0.6469(9) 0.0717(13) Uani 0.691(16) 1 d D . P A 1
H9A H 0.601289 0.149828 0.602936 0.086 Uiso 0.691(16) 1 calc R . P A 1
H9B H 0.595452 0.283538 0.675457 0.086 Uiso 0.691(16) 1 calc R . P A 1
O1 O 0.5429(14) 0.1293(10) 0.7589(12) 0.111(4) Uani 0.691(16) 1 d D . P A 1
C8 C 0.4759(10) 0.0056(9) 0.7162(10) 0.0717(13) Uani 0.691(16) 1 d D . P A 1
H8A H 0.478706 -0.046187 0.793508 0.086 Uiso 0.691(16) 1 calc R . P A 1
H8B H 0.529091 -0.042225 0.669477 0.086 Uiso 0.691(16) 1 calc R . P A 1
C7 C 0.3223(8) 0.0196(9) 0.6259(8) 0.0717(13) Uani 0.691(16) 1 d D . P A 1
H7A H 0.284784 -0.065987 0.589447 0.086 Uiso 0.691(16) 1 calc R . P A 1
H7B H 0.264285 0.053263 0.675895 0.086 Uiso 0.691(16) 1 calc R . P A 1
C5 C 0.1755(4) 0.1979(4) 0.3045(4) 0.0600(10) Uani 1 1 d . . . . .
H5 H 0.251430 0.252744 0.306647 0.072 Uiso 1 1 calc R . . . .
C2 C -0.0522(4) 0.0388(3) 0.2941(4) 0.0549(9) Uani 1 1 d . . . . .
H2 H -0.129360 -0.014804 0.290725 0.066 Uiso 1 1 calc R . . . .
C4 C 0.1882(4) 0.1150(3) 0.4113(4) 0.0456(8) Uani 1 1 d . . . . .
C17 C 0.9654(5) 0.4294(5) 0.8290(4) 0.0630(10) Uani 1 1 d D . . . .
H17A H 0.917058 0.355720 0.853730 0.076 Uiso 1 1 calc R . . . .
H17B H 0.903894 0.506441 0.815690 0.076 Uiso 1 1 calc R . . . .
C19 C 1.2261(5) 0.3221(5) 0.8402(4) 0.0720(12) Uani 1 1 d D . . . .
H19A H 1.291948 0.248367 0.854203 0.086 Uiso 1 1 calc R . . . .
H19B H 1.271869 0.399178 0.818206 0.086 Uiso 1 1 calc R . . . .
C3 C 0.0706(4) 0.0353(4) 0.4044(4) 0.0544(9) Uani 1 1 d . . . . .
H3 H 0.075212 -0.020542 0.474895 0.065 Uiso 1 1 calc R . . . .
C20 C 1.0932(4) 0.2909(4) 0.7255(4) 0.0564(9) Uani 1 1 d D . . . .
H20A H 1.117202 0.278451 0.645550 0.068 Uiso 1 1 calc R . . . .
H20B H 1.051329 0.209373 0.743289 0.068 Uiso 1 1 calc R . . . .
C15 C 0.8456(4) 0.2912(3) 0.4961(4) 0.0493(8) Uani 1 1 d . . . . .
H15 H 0.910811 0.221888 0.511409 0.059 Uiso 1 1 calc R . . . .
C6 C 0.0524(5) 0.2004(4) 0.1951(4) 0.0639(10) Uani 1 1 d . . . . .
H6 H 0.046155 0.256629 0.124462 0.077 Uiso 1 1 calc R . . . .
C18 C 1.1031(5) 0.4564(4) 0.9385(4) 0.0680(11) Uani 1 1 d D . . . .
H18A H 1.147886 0.534112 0.916389 0.082 Uiso 1 1 calc R . . . .
H18B H 1.083929 0.474751 1.019933 0.082 Uiso 1 1 calc R . . . .
C1 C -0.0608(4) 0.1207(4) 0.1899(4) 0.0529(10) Uani 1 1 d . . . . .
C11 C 0.6296(4) 0.3921(4) 0.3575(3) 0.0477(8) Uani 1 1 d . . . . .
C14 C 0.8684(4) 0.3925(3) 0.5902(4) 0.0427(7) Uani 1 1 d . . . . .
C10A C 0.358(2) 0.0010(17) 0.6083(16) 0.0717(13) Uani 0.309(16) 1 d D . P A 2
H10C H 0.402088 -0.062945 0.566305 0.086 Uiso 0.309(16) 1 calc R . P A 2
H10D H 0.270681 -0.039136 0.611121 0.086 Uiso 0.309(16) 1 calc R . P A 2
C9A C 0.455(2) 0.013(2) 0.7495(17) 0.0717(13) Uani 0.309(16) 1 d D . P A 2
H9AA H 0.408654 0.060490 0.802442 0.086 Uiso 0.309(16) 1 calc R . P A 2
H9AB H 0.484323 -0.073313 0.788513 0.086 Uiso 0.309(16) 1 calc R . P A 2
O1A O 0.575(3) 0.086(2) 0.742(3) 0.111(4) Uani 0.309(16) 1 d D . P A 2
C8A C 0.537(2) 0.215(2) 0.688(2) 0.0717(13) Uani 0.309(16) 1 d D . P A 2
H8AA H 0.622387 0.260989 0.685302 0.086 Uiso 0.309(16) 1 calc R . P A 2
H8AB H 0.497707 0.265604 0.744389 0.086 Uiso 0.309(16) 1 calc R . P A 2
C7A C 0.4287(19) 0.208(2) 0.548(2) 0.0717(13) Uani 0.309(16) 1 d D . P A 2
H7AA H 0.383078 0.294143 0.527203 0.086 Uiso 0.309(16) 1 calc R . P A 2
H7AB H 0.480576 0.193749 0.486931 0.086 Uiso 0.309(16) 1 calc R . P A 2


_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
Br2 C11 1.904(4) . ?
Br1 C1 1.901(4) . ?
N2 C17 1.457(5) . ?
N2 C20 1.454(4) . ?
N2 C14 1.412(5) . ?
C12 C13 1.376(5) . ?
C12 C11 1.379(5) . ?
C16 C15 1.384(5) . ?
C16 C11 1.371(5) . ?
O2 C19 1.410(5) . ?
O2 C18 1.421(5) . ?
C13 C14 1.403(5) . ?
N1 C10 1.417(9) . ?
N1 C7 1.434(8) . ?
N1 C4 1.413(6) . ?
N1 C10A 1.410(14) . ?
N1 C7A 1.447(16) . ?
C10 C9 1.490(10) . ?
C9 O1 1.405(12) . ?
O1 C8 1.417(11) . ?
C8 C7 1.513(10) . ?
C5 C4 1.387(5) . ?
C5 C6 1.378(6) . ?
C2 C3 1.383(5) . ?
C2 C1 1.366(5) . ?
C4 C3 1.401(5) . ?
C17 C18 1.496(6) . ?
C19 C20 1.501(5) . ?
C15 C14 1.400(5) . ?
C6 C1 1.370(5) . ?
C10A C9A 1.497(17) . ?
C9A O1A 1.423(19) . ?
O1A C8A 1.430(19) . ?
C8A C7A 1.521(18) . ?

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
C20 N2 C17 110.9(3) . . ?
C14 N2 C17 115.9(3) . . ?
C14 N2 C20 116.8(3) . . ?
C13 C12 C11 120.2(3) . . ?
C11 C16 C15 120.2(3) . . ?
C19 O2 C18 108.8(3) . . ?
C12 C13 C14 121.3(3) . . ?
C10 N1 C7 119.0(6) . . ?
C4 N1 C10 117.1(4) . . ?
C4 N1 C7 117.1(4) . . ?
C4 N1 C7A 124.0(9) . . ?
C10A N1 C4 124.0(8) . . ?
C10A N1 C7A 111.7(12) . . ?
N1 C10 C9 111.8(7) . . ?
O1 C9 C10 112.2(10) . . ?
C9 O1 C8 108.6(12) . . ?
O1 C8 C7 112.7(10) . . ?
N1 C7 C8 108.7(7) . . ?
C6 C5 C4 121.1(4) . . ?
C1 C2 C3 120.3(4) . . ?
C5 C4 N1 120.6(3) . . ?
C5 C4 C3 117.5(4) . . ?
C3 C4 N1 121.9(3) . . ?
N2 C17 C18 110.7(3) . . ?
O2 C19 C20 112.6(4) . . ?
C2 C3 C4 120.8(3) . . ?
N2 C20 C19 110.0(3) . . ?
C16 C15 C14 121.3(3) . . ?
C1 C6 C5 120.4(4) . . ?
O2 C18 C17 111.3(4) . . ?
C2 C1 Br1 120.6(3) . . ?
C2 C1 C6 119.9(4) . . ?
C6 C1 Br1 119.5(3) . . ?
C12 C11 Br2 120.3(3) . . ?
C16 C11 Br2 119.8(3) . . ?
C16 C11 C12 120.0(3) . . ?
C13 C14 N2 120.2(3) . . ?
C15 C14 N2 122.7(3) . . ?
C15 C14 C13 117.0(3) . . ?
N1 C10A C9A 123.4(16) . . ?
O1A C9A C10A 105(2) . . ?
C9A O1A C8A 113(2) . . ?
O1A C8A C7A 111(2) . . ?
N1 C7A C8A 118.4(17) . . ?

_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_1_CCDC1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2224503'
loop_
_audit_author_name
_audit_author_address
'Dongyan Jiang'
;Jilin university
China
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-01-10
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.01.06 svn.r734b3b31 for OlexSys, GUI svn.r6444)
;
_chemical_formula_moiety         'C10 H12 Cl N O'
_chemical_formula_sum            'C10 H12 Cl N O'
_chemical_formula_weight         197.665
_chemical_absolute_configuration unk
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
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 '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'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 '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'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 '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 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 '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 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 '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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           ' P -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x,-y,z+1/2

_symmetry_Int_Tables_number      7
_cell_length_a                   9.885(3)
_cell_length_b                   10.023(4)
_cell_length_c                   10.661(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.207(10)
_cell_angle_gamma                90
_cell_volume                     991.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9046
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.88
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             416.808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.9972
_diffrn_reflns_Laue_measured_fraction_max 0.9972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20705
_diffrn_reflns_point_group_measured_fraction_full 0.9676
_diffrn_reflns_point_group_measured_fraction_max 0.9619
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.76
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.926
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              -13
_reflns_number_gt                3371
_reflns_number_total             4067
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.1132
_refine_diff_density_min         -0.1176
_refine_diff_density_rms         0.0273
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.014(15)
_refine_ls_d_res_high            0.7894
_refine_ls_d_res_low             7.0809
_refine_ls_goodness_of_fit_ref   1.0830
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    53
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.0722
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+0.0740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0759
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N00G-C00I \\sim N00G-C1
 with sigma of 0.02
 N00G-C00J \\sim N00G-C2
 with sigma of 0.02
 C00I-C3 \\sim C1-C3a
 with sigma of 0.02
 C00J-C00O \\sim C2-C4
 with sigma of 0.02
 O00M-C00O \\sim O00n-C4
 with sigma of 0.02
 O00M-C3 \\sim O00n-C3a
 with sigma of 0.02
 N00G-C00O \\sim N00G-C4
 with sigma of 0.04
 N00G-C3 \\sim N00G-C3a
 with sigma of 0.04
 C00I-O00M \\sim C1-O00n
 with sigma of 0.04
 C00J-O00M \\sim C2-O00n
 with sigma of 0.04
 C00O-C3 \\sim C4-C3a
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq, Uanis(C3a) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 C1, C2, O00n, C4, C3a
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00I, C3, C00O, C00J, O00M
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1)=Sof(C2)=Sof(O00n)=Sof(C4)=Sof(C3a)=Sof(H1a)=Sof(H1b)=Sof(H2a)=
 Sof(H2b)=Sof(H4a)=Sof(H4b)=Sof(H3aa)=Sof(H3ab)=Sof(H1a)=Sof(H1b)=Sof(H2a)=
 Sof(H2b)=Sof(H00l)=Sof(H00m)=Sof(H4a)=Sof(H4b)=Sof(H3aa)=Sof(H3ab)=1-FVAR(1)
 Sof(C00I)=Sof(C00J)=Sof(O00M)=Sof(C00O)=Sof(C3)=Sof(H00I)=Sof(H00a)=Sof(H00c)=
 Sof(H00O)=Sof(H3a)=Sof(H3b)=Sof(H00a)=Sof(H00c)=Sof(H00e)=Sof(H00f)=Sof(H00g)=
 Sof(H00h)=Sof(H00g)=Sof(H00h)=Sof(H3a)=Sof(H3b)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C007(H00i,H00j), C00C(H00l,H00m), C00I(H00a,H00c), C00J(H00e,H00f), C00O(H00g,
 H00h), C3(H3a,H3b), C1(H1a,H1b), C2(H2a,H2b), C4(H4a,H4b), C3a(H3aa,H3ab),
 C00P(H00r,H00s), C00N(H00p,H00q)
6.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00E(H00n), C00H(H00o), C005(H005), C00B(H00B), C00K(H00K),
 C00D(H00D), C008(H008)
;
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
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Cl01 Cl 1.04494(6) 0.60114(6) 0.26703(6) 0.07646(17) Uani 1.000000 . . .
Cl02 Cl 0.74096(7) 0.87846(6) 0.43621(6) 0.0866(2) Uani 1.000000 . . .
N003 N 0.52409(15) 0.60055(13) -0.22582(15) 0.0491(3) Uani 1.000000 . . .
C004 C 0.64929(18) 0.60435(15) -0.11016(16) 0.0462(4) Uani 1.000000 . . .
C005 C 0.79397(19) 0.70202(19) 0.10122(18) 0.0612(5) Uani 1.000000 . . .
O006 O 0.31515(16) 0.65767(17) -0.48022(14) 0.0762(4) Uani 1.000000 . . .
C007 C 0.4229(2) 0.71006(19) -0.24464(18) 0.0621(5) Uani 1.000000 . . .
C008 C 0.5757(2) 0.95996(19) 0.1880(2) 0.0613(5) Uani 1.000000 . . .
C009 C 0.87107(19) 0.5008(2) 0.02927(19) 0.0623(5) Uani 1.000000 . . .
C00A C 0.3311(2) 0.88468(16) 0.0730(2) 0.0514(4) Uani 1.000000 . . .
C00B C 0.4712(2) 0.8003(2) 0.2922(2) 0.0705(5) Uani 1.000000 . . .
C00C C 0.5469(2) 0.5689(2) -0.35097(19) 0.0718(6) Uani 1.000000 . . .
C00D C 0.4507(2) 0.96242(18) 0.0779(2) 0.0608(5) Uani 1.000000 . . .
C00E C 0.7507(2) 0.50175(18) -0.08536(18) 0.0580(4) Uani 1.000000 . . .
C00F C 0.89181(19) 0.60053(19) 0.12176(18) 0.0576(5) Uani 1.000000 . . .
N00G N 0.20183(18) 0.89114(16) -0.0351(2) 0.0733(5) Uani 1.000000 D . .
C00H C 0.67390(19) 0.70430(17) -0.01418(17) 0.0561(4) Uani 1.000000 . . .
C00I C 0.0825(9) 0.7943(19) -0.0580(9) 0.088(4) Uani 0.366(8) D U 1
C00J C 0.1600(9) 1.0067(14) -0.1175(9) 0.093(4) Uani 0.366(8) D U 1
C00K C 0.3462(2) 0.80319(19) 0.18301(19) 0.0656(5) Uani 1.000000 . . .
C00L C 0.5855(2) 0.87932(19) 0.2944(2) 0.0614(5) Uani 1.000000 . . .
O00M O -0.0677(6) 0.9141(10) -0.2505(6) 0.103(3) Uani 0.366(8) D U 1
C00N C 0.4061(2) 0.5460(2) -0.4612(2) 0.0763(6) Uani 1.000000 . . .
C00O C 0.0461(8) 0.9791(12) -0.2627(8) 0.086(3) Uani 0.366(8) D U 1
C00P C 0.2874(2) 0.6822(3) -0.3610(2) 0.0819(7) Uani 1.000000 . . .
C3 C -0.0209(8) 0.7771(11) -0.1921(8) 0.084(3) Uani 0.366(8) D U 1
H009 H 0.93965(19) 0.4309(2) 0.04401(19) 0.0748(6) Uiso 1.000000 R . .
H00n H 0.7367(2) 0.43147(18) -0.14839(18) 0.0696(5) Uiso 1.000000 R . .
H00o H 0.60688(19) 0.77553(17) -0.02821(17) 0.0674(5) Uiso 1.000000 R . .
H005 H 0.80844(19) 0.77069(19) 0.16597(18) 0.0734(6) Uiso 1.000000 R . .
H00B H 0.4785(2) 0.7439(2) 0.3659(2) 0.0846(6) Uiso 1.000000 R . .
H00K H 0.2678(2) 0.74808(19) 0.18248(19) 0.0788(6) Uiso 1.000000 R . .
H00D H 0.4455(2) 1.01780(18) 0.0041(2) 0.0729(6) Uiso 1.000000 R . .
H008 H 0.6551(2) 1.01434(19) 0.1900(2) 0.0736(6) Uiso 1.000000 R . .
H00i H 0.3990(2) 0.72226(19) -0.16254(18) 0.0745(6) Uiso 1.000000 R . .
H00j H 0.4676(2) 0.79353(19) -0.26117(18) 0.0745(6) Uiso 1.000000 R . .
H00l H 0.5987(2) 0.6434(2) -0.37546(19) 0.0861(7) Uiso 1.000000 R . .
H00m H 0.6074(2) 0.4879(2) -0.33866(19) 0.0861(7) Uiso 1.000000 R . .
C1 C 0.1923(5) 0.9804(6) -0.1407(5) 0.0662(14) Uani 0.634(8) D U 2
C2 C 0.1175(6) 0.7756(8) -0.0676(5) 0.0626(13) Uani 0.634(8) D U 2
O00n O -0.0315(4) 0.8761(6) -0.2747(4) 0.1057(16) Uani 0.634(8) D U 2
C4 C -0.0366(6) 0.8107(7) -0.1603(6) 0.0903(17) Uani 0.634(8) D U 2
C3a C 0.0400(6) 1.0061(7) -0.2250(6) 0.0861(18) Uani 0.634(8) D U 2
H00a H 0.1261(9) 0.7061(19) -0.0269(9) 0.105(5) Uiso 0.366(8) R . 1
H00c H 0.0279(9) 0.8203(19) 0.0006(9) 0.105(5) Uiso 0.366(8) R . 1
H00e H 0.1184(9) 1.0726(14) -0.0718(9) 0.112(4) Uiso 0.366(8) R . 1
H00f H 0.2473(9) 1.0473(14) -0.1271(9) 0.112(4) Uiso 0.366(8) R . 1
H00g H 0.0143(8) 1.0646(12) -0.3103(8) 0.103(3) Uiso 0.366(8) R . 1
H00h H 0.0911(8) 0.9246(12) -0.3152(8) 0.103(3) Uiso 0.366(8) R . 1
H3a H 0.0238(8) 0.7275(11) -0.2480(8) 0.101(3) Uiso 0.366(8) R . 1
H3b H -0.1053(8) 0.7258(11) -0.1890(8) 0.101(3) Uiso 0.366(8) R . 1
H1a H 0.2393(5) 1.0657(6) -0.1031(5) 0.0794(17) Uiso 0.634(8) R . 2
H1b H 0.2443(5) 0.9423(6) -0.1968(5) 0.0794(17) Uiso 0.634(8) R . 2
H2a H 0.1612(6) 0.7114(8) -0.1130(5) 0.0751(15) Uiso 0.634(8) R . 2
H2b H 0.1139(6) 0.7332(8) 0.0150(5) 0.0751(15) Uiso 0.634(8) R . 2
H4a H -0.0946(6) 0.7282(7) -0.1865(6) 0.108(2) Uiso 0.634(8) R . 2
H4b H -0.0833(6) 0.8691(7) -0.1123(6) 0.108(2) Uiso 0.634(8) R . 2
H3aa H -0.0105(6) 1.0523(7) -0.1718(6) 0.103(2) Uiso 0.634(8) R . 2
H3ab H 0.0363(6) 1.0639(7) -0.3014(6) 0.103(2) Uiso 0.634(8) R . 2
H00r H 0.2216(2) 0.7596(3) -0.3745(2) 0.0983(8) Uiso 1.000000 R . .
H00s H 0.2382(2) 0.6037(3) -0.3400(2) 0.0983(8) Uiso 1.000000 R . .
H00p H 0.3578(2) 0.4674(2) -0.4395(2) 0.0916(7) Uiso 1.000000 R . .
H00q H 0.4241(2) 0.5267(2) -0.5452(2) 0.0916(7) Uiso 1.000000 R . .


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
Cl01 C00F 1.7522(19) . ?
Cl02 C00L 1.744(2) . ?
N003 C004 1.414(2) . ?
N003 C007 1.451(2) . ?
N003 C00C 1.463(2) . ?
C004 C00E 1.396(2) . ?
C004 C00H 1.392(2) . ?
C005 C00F 1.368(3) . ?
C005 C00H 1.384(2) . ?
C005 H005 0.9500 . ?
O006 C00N 1.406(3) . ?
O006 C00P 1.412(3) . ?
C007 C00P 1.505(3) . ?
C007 H00i 0.9900 . ?
C007 H00j 0.9900 . ?
C008 C00D 1.380(3) . ?
C008 C00L 1.369(3) . ?
C008 H008 0.9500 . ?
C009 C00E 1.380(2) . ?
C009 C00F 1.369(3) . ?
C009 H009 0.9500 . ?
C00A C00D 1.402(3) . ?
C00A N00G 1.396(3) . ?
C00A C00K 1.394(3) . ?
C00B C00K 1.375(3) . ?
C00B C00L 1.373(3) . ?
C00B H00B 0.9500 . ?
C00C C00N 1.497(3) . ?
C00C H00l 0.9900 . ?
C00C H00m 0.9900 . ?
C00D H00D 0.9500 . ?
C00E H00n 0.9500 . ?
N00G C00I 1.481(14) . ?
N00G C00J 1.426(13) . ?
N00G C1 1.416(6) . ?
N00G C2 1.398(7) . ?
C00H H00o 0.9500 . ?
C00I C3 1.452(11) . ?
C00I H00a 0.9900 . ?
C00I H00c 0.9900 . ?
C00J C00O 1.593(11) . ?
C00J H00e 0.9900 . ?
C00J H00f 0.9900 . ?
C00K H00K 0.9500 . ?
O00M C00O 1.345(13) . ?
O00M C3 1.513(15) . ?
C00N H00p 0.9900 . ?
C00N H00q 0.9900 . ?
C00O H00g 0.9900 . ?
C00O H00h 0.9900 . ?
C00P H00r 0.9900 . ?
C00P H00s 0.9900 . ?
C3 H3a 0.9900 . ?
C3 H3b 0.9900 . ?
C1 C3a 1.485(7) . ?
C1 H1a 0.9900 . ?
C1 H1b 0.9900 . ?
C2 C4 1.543(7) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
O00n C4 1.401(8) . ?
O00n C3a 1.490(8) . ?
C4 H4a 0.9900 . ?
C4 H4b 0.9900 . ?
C3a H3aa 0.9900 . ?
C3a H3ab 0.9900 . ?

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
C007 N003 C004 116.99(14) . . ?
C00C N003 C004 115.90(13) . . ?
C00C N003 C007 110.74(14) . . ?
C00E C004 N003 120.02(14) . . ?
C00H C004 N003 122.58(15) . . ?
C00H C004 C00E 117.33(16) . . ?
C00H C005 C00F 119.77(17) . . ?
H005 C005 C00F 120.12(11) . . ?
H005 C005 C00H 120.12(10) . . ?
C00P O006 C00N 108.84(16) . . ?
C00P C007 N003 110.41(16) . . ?
H00i C007 N003 109.57(10) . . ?
H00i C007 C00P 109.57(11) . . ?
H00j C007 N003 109.57(10) . . ?
H00j C007 C00P 109.57(13) . . ?
H00j C007 H00i 108.1 . . ?
C00L C008 C00D 120.12(18) . . ?
H008 C008 C00D 119.94(11) . . ?
H008 C008 C00L 119.94(12) . . ?
C00F C009 C00E 120.13(17) . . ?
H009 C009 C00E 119.94(11) . . ?
H009 C009 C00F 119.94(11) . . ?
N00G C00A C00D 121.66(17) . . ?
C00K C00A C00D 116.78(18) . . ?
C00K C00A N00G 121.54(17) . . ?
C00L C00B C00K 119.73(19) . . ?
H00B C00B C00K 120.13(12) . . ?
H00B C00B C00L 120.13(12) . . ?
C00N C00C N003 110.77(17) . . ?
H00l C00C N003 109.49(11) . . ?
H00l C00C C00N 109.49(13) . . ?
H00m C00C N003 109.49(10) . . ?
H00m C00C C00N 109.49(12) . . ?
H00m C00C H00l 108.1 . . ?
C00A C00D C008 121.20(18) . . ?
H00D C00D C008 119.40(11) . . ?
H00D C00D C00A 119.40(12) . . ?
C009 C00E C004 121.04(17) . . ?
H00n C00E C004 119.48(10) . . ?
H00n C00E C009 119.48(11) . . ?
C005 C00F Cl01 119.08(15) . . ?
C009 C00F Cl01 120.53(15) . . ?
C009 C00F C005 120.39(16) . . ?
C00I N00G C00A 123.8(5) . . ?
C00J N00G C00A 122.3(4) . . ?
C00J N00G C00I 112.7(6) . . ?
C1 N00G C00A 118.5(2) . . ?
C1 N00G C00I 116.9(5) . . ?
C1 N00G C00J 21.7(5) . . ?
C2 N00G C00A 117.6(2) . . ?
C2 N00G C00I 17.1(7) . . ?
C2 N00G C00J 119.9(4) . . ?
C2 N00G C1 117.1(3) . . ?
C005 C00H C004 121.34(16) . . ?
H00o C00H C004 119.33(10) . . ?
H00o C00H C005 119.33(10) . . ?
C3 C00I N00G 119.3(10) . . ?
H00a C00I N00G 107.5(6) . . ?
H00a C00I C3 107.5(9) . . ?
H00c C00I N00G 107.5(5) . . ?
H00c C00I C3 107.5(6) . . ?
H00c C00I H00a 107.0 . . ?
C00O C00J N00G 114.5(10) . . ?
H00e C00J N00G 108.6(4) . . ?
H00e C00J C00O 108.6(6) . . ?
H00f C00J N00G 108.6(4) . . ?
H00f C00J C00O 108.6(6) . . ?
H00f C00J H00e 107.584602591(15) . . ?
C00B C00K C00A 121.88(18) . . ?
H00K C00K C00A 119.06(12) . . ?
H00K C00K C00B 119.06(12) . . ?
C008 C00L Cl02 120.68(16) . . ?
C00B C00L Cl02 119.02(16) . . ?
C00B C00L C008 120.27(19) . . ?
C3 O00M C00O 109.4(7) . . ?
C00C C00N O006 111.48(17) . . ?
H00p C00N O006 109.33(12) . . ?
H00p C00N C00C 109.33(13) . . ?
H00q C00N O006 109.33(11) . . ?
H00q C00N C00C 109.33(12) . . ?
H00q C00N H00p 108.0 . . ?
O00M C00O C00J 108.9(8) . . ?
H00g C00O C00J 109.9(7) . . ?
H00g C00O O00M 109.9(6) . . ?
H00h C00O C00J 109.9(6) . . ?
H00h C00O O00M 109.9(6) . . ?
H00h C00O H00g 108.3 . . ?
C007 C00P O006 112.33(17) . . ?
H00r C00P O006 109.14(11) . . ?
H00r C00P C007 109.14(11) . . ?
H00s C00P O006 109.14(14) . . ?
H00s C00P C007 109.14(13) . . ?
H00s C00P H00r 107.9 . . ?
O00M C3 C00I 108.0(10) . . ?
H3a C3 C00I 110.1(6) . . ?
H3a C3 O00M 110.1(4) . . ?
H3b C3 C00I 110.1(7) . . ?
H3b C3 O00M 110.1(4) . . ?
H3b C3 H3a 108.4 . . ?
C3a C1 N00G 111.5(5) . . ?
H1a C1 N00G 109.3(2) . . ?
H1a C1 C3a 109.3(4) . . ?
H1b C1 N00G 109.3(3) . . ?
H1b C1 C3a 109.3(4) . . ?
H1b C1 H1a 108.0 . . ?
C4 C2 N00G 110.0(5) . . ?
H2a C2 N00G 109.7(3) . . ?
H2a C2 C4 109.7(4) . . ?
H2b C2 N00G 109.7(2) . . ?
H2b C2 C4 109.7(4) . . ?
H2b C2 H2a 108.2 . . ?
C3a O00n C4 104.8(5) . . ?
O00n C4 C2 109.9(5) . . ?
H4a C4 C2 109.7(4) . . ?
H4a C4 O00n 109.7(3) . . ?
H4b C4 C2 109.7(4) . . ?
H4b C4 O00n 109.7(4) . . ?
H4b C4 H4a 108.2 . . ?
O00n C3a C1 108.7(5) . . ?
H3aa C3a C1 109.9(4) . . ?
H3aa C3a O00n 109.9(4) . . ?
H3ab C3a C1 109.9(3) . . ?
H3ab C3a O00n 109.9(3) . . ?
H3ab C3a H3aa 108.3 . . ?

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
Cl01 C00F C005 C00H 178.79(13) . . . . ?
Cl01 C00F C009 C00E -179.48(15) . . . . ?
Cl02 C00L C008 C00D -178.23(15) . . . . ?
Cl02 C00L C00B C00K 177.85(16) . . . . ?
N003 C004 C00E C009 -177.61(16) . . . . ?
N003 C004 C00H C005 176.81(17) . . . . ?
N003 C007 C00P O006 -56.46(18) . . . . ?
N003 C00C C00N O006 57.78(19) . . . . ?
C004 C00E C009 C00F 0.8(2) . . . . ?
C004 C00H C005 C00F 0.6(2) . . . . ?
C005 C00F C009 C00E -0.3(2) . . . . ?
C008 C00D C00A N00G 176.92(18) . . . . ?
C008 C00D C00A C00K -1.4(2) . . . . ?
C008 C00L C00B C00K -0.5(2) . . . . ?
C00A N00G C00I C3 -157.1(9) . . . . ?
C00A N00G C00J C00O 157.6(7) . . . . ?
C00A N00G C1 C3a -162.6(5) . . . . ?
C00A N00G C2 C4 164.1(4) . . . . ?
C00A C00K C00B C00L -0.1(2) . . . . ?
N00G C00I C3 O00M -47.0(11) . . . . ?
N00G C00J C00O O00M 53.4(8) . . . . ?
N00G C1 C3a O00n -55.9(5) . . . . ?
N00G C2 C4 O00n 56.7(5) . . . . ?
C00I C3 O00M C00O 64.0(8) . . . . ?
C00J C00O O00M C3 -66.0(9) . . . . ?
C1 C3a O00n C4 67.1(5) . . . . ?
C2 C4 O00n C3a -66.9(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
N00G C00I 1 1
N00G C00J 1 2
N00G C00O 1 7
N00G C3 1 8
N00G C1 1 1
N00G C2 1 2
N00G C4 1 7
N00G C3a 1 8
C00I O00M 1 9
C00I C3 1 3
C00J O00M 1 10
C00J C00O 1 4
O00M C00O 1 5
O00M C3 1 6
C00O C3 1 11
C1 O00n 1 9
C1 C3a 1 3
C2 O00n 1 10
C2 C4 1 4
O00n C4 1 5
O00n C3a 1 6
C4 C3a 1 11

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.4484 0.0328 0.0328
2 0.0200 1.4124 0.0141 0.0141
3 0.0200 1.4684 0.0162 0.0162
4 0.0200 1.5680 0.0248 0.0248
5 0.0200 1.3728 0.0279 0.0279
6 0.0200 1.5013 0.0117 0.0117
7 0.0400 2.4760 0.0650 0.0650
8 0.0400 2.4646 0.0674 0.0674
9 0.0400 2.4079 0.0092 0.0092
10 0.0400 2.4028 0.0080 0.0080
11 0.0400 2.3126 0.0224 0.0224

loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
C00I O00M 0.004000 -0.016069 0.013912 0.002220
C00I C3 0.004000 0.000117 0.004002 0.000105
C00J O00M 0.004000 -0.014297 -0.001713 -0.001826
C00J C00O 0.004000 -0.002338 -0.008588 0.005389
O00M C00O 0.004000 -0.013054 0.004654 0.006263
O00M C3 0.004000 -0.004084 -0.012020 0.017211
C00O C3 0.004000 -0.032741 -0.017727 -0.001719
C1 O00n 0.004000 -0.005674 -0.020559 0.002992
C1 C3a 0.004000 0.004660 -0.004214 -0.008346
C2 O00n 0.004000 0.016947 0.013636 -0.002755
C2 C4 0.004000 0.004055 0.004543 -0.018670
O00n C4 0.004000 -0.014589 -0.023525 -0.005765
O00n C3a 0.004000 -0.033693 0.005269 0.012171
C4 C3a 0.004000 -0.016938 0.014232 -0.003682

loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C4 0.0050
C3a 0.0050

