# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_GSF-II-100K-XOu
_database_code_depnum_ccdc_archive 'CCDC 1918290'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;School of pharmaceutical Science, Sun Yat sen University
China
;
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            griseofulvin
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 Cl O6'
_chemical_formula_sum            'C17 H17 Cl O6'
_chemical_formula_weight         352.76
_chemical_absolute_configuration ad
_chemical_melting_point          488k
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.6345(2)
_cell_length_b                   12.0011(3)
_cell_length_c                   23.8695(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3332.82(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28350
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.0370
_cell_measurement_theta_min      3.7030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourles
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.197
_diffrn_reflns_theta_min         3.704
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  61.00   0.50    0.07    --   46.62 -35.00-105.00  176
  2  ω   -173.00 -81.00   0.50    0.42    -- -100.00 -93.00  62.00  184
  3  ω     85.00 178.00   0.50    0.42    --  107.00 108.00 -97.00  186
  4  ω     33.00 122.00   0.50    0.42    --  107.00 -35.00-105.00  178
  5  ω   -120.00 -32.00   0.50    0.07    --  -46.62 -38.00-180.00  176
  6  ω   -119.00 -71.00   0.50    0.07    --  -46.62-125.00 -30.00   96
  7  ω   -119.00 -71.00   0.50    0.07    --  -46.62-125.00-120.00   96
  8  ω   -119.00 -71.00   0.50    0.07    --  -46.62-125.00 -90.00   96
  9  ω     34.00 109.00   0.50    0.42    --  107.00 -94.00 -30.00  150
 10  ω     89.00 178.00   0.50    0.42    --  107.00  15.00 150.00  178
 11  ω     93.00 178.00   0.50    0.42    --  107.00  45.00  90.00  170
 12  ω     83.00 178.00   0.50    0.42    --  107.00  77.00-150.00  190
 13  ω     31.00 125.00   0.50    0.42    --  107.00 -15.00 120.00  188
 14  ω     34.00 125.00   0.50    0.42    --  107.00 -61.00  60.00  182
 15  ω     34.00 131.00   0.50    0.42    --  107.00 -77.00 150.00  194
 16  ω     34.00 125.00   0.50    0.42    --  107.00 -61.00 150.00  182
 17  ω   -119.00 -23.00   0.50    0.07    --  -46.62 -77.00   0.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0591749000
_diffrn_orient_matrix_UB_12      0.0507000000
_diffrn_orient_matrix_UB_13      0.0518285000
_diffrn_orient_matrix_UB_21      -0.1071653000
_diffrn_orient_matrix_UB_22      -0.0262328000
_diffrn_orient_matrix_UB_23      0.0355439000
_diffrn_orient_matrix_UB_31      0.0505420000
_diffrn_orient_matrix_UB_32      -0.1149746000
_diffrn_orient_matrix_UB_33      0.0146797000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                6785
_reflns_number_total             6937
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.176
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6937
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.044
_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)+(0.0404P)²+0.7341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0726
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00W(H00W), C014(H014)
2.b Secondary CH2 refined with riding coordinates:
 C00Z(H00D,H00E), C019(H01P,H01Q)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00Y(H00Y), C010(H010)
2.d Idealised Me refined as rotating group:
 C00R(H00A,H00B,H00C), C013(H01A,H01B,H01C), C015(H01J,H01K,H01L), C017(H01D,
 H01E,H01F), C018(H01M,H01N,H01O), C01A(H01R,H01S,H01T), C01B(H01G,H01H,H01I),
 C01C(H01U,H01V,H01W)
;
_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
Cl01 Cl 0.34795(4) 0.44348(4) 0.70662(2) 0.02497(11) Uani 1 1 d . . . . .
Cl02 Cl 0.37842(5) 0.70225(5) 0.27002(2) 0.03304(13) Uani 1 1 d . . . . .
O003 O 0.52375(12) 0.27873(11) 0.66344(6) 0.0197(3) Uani 1 1 d . . . . .
O004 O 0.76466(12) 0.53067(12) 0.57235(6) 0.0226(3) Uani 1 1 d . . . . .
O005 O 0.53632(12) 0.54576(11) 0.33673(6) 0.0210(3) Uani 1 1 d . . . . .
O006 O 0.41974(13) 0.65967(12) 0.66628(7) 0.0266(3) Uani 1 1 d . . . . .
O007 O 0.73821(12) 0.48333(12) 0.29648(6) 0.0227(3) Uani 1 1 d . . . . .
O008 O 0.78514(13) 0.27568(12) 0.58630(6) 0.0254(3) Uani 1 1 d . . . . .
O009 O 0.48589(13) 0.19711(13) 0.56290(6) 0.0267(3) Uani 1 1 d . . . . .
O00A O 0.76085(13) 0.56671(12) 0.43715(6) 0.0248(3) Uani 1 1 d . . . . .
O00B O 0.73187(14) 0.81604(12) 0.43752(6) 0.0277(3) Uani 1 1 d . . . . .
O00C O 0.43286(16) 0.92212(14) 0.30674(7) 0.0342(4) Uani 1 1 d . . . . .
O00D O 0.70378(16) -0.12029(14) 0.61298(9) 0.0399(4) Uani 1 1 d . . . . .
O00E O 0.7229(3) 0.17116(17) 0.41763(10) 0.0685(8) Uani 1 1 d . . . . .
C00F C 0.66683(17) 0.51679(17) 0.60161(8) 0.0196(4) Uani 1 1 d . . . . .
C00G C 0.59317(17) 0.60319(17) 0.61708(8) 0.0215(4) Uani 1 1 d . . . . .
H00G H 0.609721 0.675994 0.606450 0.026 Uiso 1 1 calc R . . . .
C00H C 0.73895(19) 0.32165(17) 0.35576(9) 0.0244(4) Uani 1 1 d . . . . .
H00H H 0.793099 0.285440 0.333626 0.029 Uiso 1 1 calc R . . . .
C00I C 0.70150(16) 0.42272(16) 0.34026(8) 0.0182(4) Uani 1 1 d . . . . .
C00J C 0.64995(19) 0.79738(16) 0.39887(8) 0.0220(4) Uani 1 1 d . . . . .
C00K C 0.53944(17) 0.38714(16) 0.64873(8) 0.0190(4) Uani 1 1 d . . . . .
C00L C 0.54688(17) 0.65720(16) 0.34566(8) 0.0200(4) Uani 1 1 d . . . . .
C00M C 0.49380(17) 0.58041(17) 0.64877(8) 0.0215(4) Uani 1 1 d . . . . .
C00N C 0.63877(17) 0.40696(17) 0.61741(8) 0.0200(4) Uani 1 1 d . . . . .
C00O C 0.69502(17) 0.30036(17) 0.60913(8) 0.0197(4) Uani 1 1 d . . . . .
C00P C 0.61587(16) 0.48889(16) 0.37417(8) 0.0184(4) Uani 1 1 d . . . . .
C00Q C 0.46621(17) 0.47134(17) 0.66503(8) 0.0206(4) Uani 1 1 d . . . . .
C00R C 0.79695(19) 0.64343(17) 0.55864(9) 0.0249(4) Uani 1 1 d . . . . .
H00A H 0.740212 0.675388 0.534255 0.037 Uiso 1 1 calc GR . . . .
H00B H 0.870245 0.643234 0.540165 0.037 Uiso 1 1 calc GR . . . .
H00C H 0.801891 0.686736 0.592367 0.037 Uiso 1 1 calc GR . . . .
C00S C 0.56040(17) 0.13913(18) 0.59401(8) 0.0216(4) Uani 1 1 d . . . . .
C00T C 0.68183(17) 0.58324(15) 0.40478(8) 0.0191(4) Uani 1 1 d . . . . .
C00U C 0.50134(19) 0.84864(18) 0.33316(9) 0.0256(4) Uani 1 1 d . . . . .
C00V C 0.61532(16) 0.21312(16) 0.63793(8) 0.0190(4) Uani 1 1 d . . . . .
C00W C 0.67398(16) 0.14605(16) 0.68427(8) 0.0195(4) Uani 1 1 d . . . . .
H00W H 0.613279 0.111935 0.706986 0.023 Uiso 1 1 calc R . . . .
C00X C 0.63026(17) 0.68540(16) 0.38524(8) 0.0206(4) Uani 1 1 d . . . . .
C00Y C 0.58503(19) 0.87980(17) 0.37244(9) 0.0248(4) Uani 1 1 d . . . . .
H00Y H 0.597119 0.954586 0.380782 0.030 Uiso 1 1 calc R . . . .
C00Z C 0.74541(17) 0.05171(18) 0.65929(9) 0.0249(4) Uani 1 1 d . . . . .
H00D H 0.810200 0.083495 0.639324 0.030 Uiso 1 1 calc R . . . .
H00E H 0.775660 0.006346 0.689521 0.030 Uiso 1 1 calc R . . . .
C010 C 0.58764(19) 0.03051(18) 0.58747(9) 0.0271(4) Uani 1 1 d . . . . .
H010 H 0.547003 -0.011886 0.561559 0.033 Uiso 1 1 calc R . . . .
C011 C 0.67855(19) -0.02197(18) 0.61973(10) 0.0275(4) Uani 1 1 d . . . . .
C012 C 0.48149(18) 0.73690(18) 0.31891(8) 0.0239(4) Uani 1 1 d . . . . .
C013 C 0.74661(19) 0.21845(18) 0.72329(9) 0.0256(4) Uani 1 1 d . . . . .
H01A H 0.815298 0.241310 0.704200 0.038 Uiso 1 1 calc GR . . . .
H01B H 0.766794 0.176438 0.756072 0.038 Uiso 1 1 calc GR . . . .
H01C H 0.703347 0.283081 0.734113 0.038 Uiso 1 1 calc GR . . . .
C014 C 0.54490(17) 0.41476(17) 0.41351(9) 0.0235(4) Uani 1 1 d . . . . .
H014 H 0.493988 0.369225 0.390151 0.028 Uiso 1 1 calc R . . . .
C015 C 0.4692(2) 0.4816(2) 0.45356(10) 0.0302(5) Uani 1 1 d . . . . .
H01J H 0.516824 0.521040 0.479732 0.045 Uiso 1 1 calc GR . . . .
H01K H 0.419229 0.431824 0.473529 0.045 Uiso 1 1 calc GR . . . .
H01L H 0.423930 0.533878 0.432597 0.045 Uiso 1 1 calc GR . . . .
C016 C 0.6971(2) 0.26690(19) 0.40640(11) 0.0350(5) Uani 1 1 d . . . . .
C017 C 0.4307(2) 0.1388(2) 0.51736(9) 0.0346(5) Uani 1 1 d . . . . .
H01D H 0.487764 0.114031 0.491134 0.052 Uiso 1 1 calc GR . . . .
H01E H 0.377854 0.188021 0.498850 0.052 Uiso 1 1 calc GR . . . .
H01F H 0.389681 0.075625 0.531816 0.052 Uiso 1 1 calc GR . . . .
C018 C 0.82721(19) 0.43575(19) 0.26229(9) 0.0295(4) Uani 1 1 d . . . . .
H01M H 0.844835 0.485624 0.232038 0.044 Uiso 1 1 calc GR . . . .
H01N H 0.801465 0.365773 0.247382 0.044 Uiso 1 1 calc GR . . . .
H01O H 0.894800 0.424062 0.284596 0.044 Uiso 1 1 calc GR . . . .
C019 C 0.6238(2) 0.33563(18) 0.44536(9) 0.0294(5) Uani 1 1 d . . . . .
H01P H 0.673143 0.378454 0.470024 0.035 Uiso 1 1 calc R . . . .
H01Q H 0.577571 0.286320 0.468380 0.035 Uiso 1 1 calc R . . . .
C01A C 0.7561(2) 0.92981(19) 0.45157(11) 0.0376(5) Uani 1 1 d . . . . .
H01R H 0.781141 0.968873 0.418673 0.056 Uiso 1 1 calc GR . . . .
H01S H 0.815432 0.932318 0.479470 0.056 Uiso 1 1 calc GR . . . .
H01T H 0.687786 0.964414 0.465979 0.056 Uiso 1 1 calc GR . . . .
C01B C 0.4422(2) 0.77376(18) 0.65097(11) 0.0329(5) Uani 1 1 d . . . . .
H01G H 0.444755 0.780076 0.610893 0.049 Uiso 1 1 calc GR . . . .
H01H H 0.514687 0.796600 0.666414 0.049 Uiso 1 1 calc GR . . . .
H01I H 0.382253 0.820596 0.665393 0.049 Uiso 1 1 calc GR . . . .
C01C C 0.4454(2) 1.0382(2) 0.31944(12) 0.0391(6) Uani 1 1 d . . . . .
H01U H 0.396890 1.081150 0.295095 0.059 Uiso 1 1 calc GR . . . .
H01V H 0.524041 1.060018 0.314056 0.059 Uiso 1 1 calc GR . . . .
H01W H 0.423725 1.051329 0.357685 0.059 Uiso 1 1 calc GR . . . .


_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
Cl01 C00Q 1.729(2) . ?
Cl02 C012 1.724(2) . ?
O003 C00K 1.360(2) . ?
O003 C00V 1.458(2) . ?
O004 C00F 1.346(2) . ?
O004 C00R 1.442(2) . ?
O005 C00L 1.360(2) . ?
O005 C00P 1.456(2) . ?
O006 C00M 1.350(3) . ?
O006 C01B 1.441(3) . ?
O007 C00I 1.343(2) . ?
O007 C018 1.437(2) . ?
O008 C00O 1.218(3) . ?
O009 C00S 1.337(3) . ?
O009 C017 1.443(3) . ?
O00A C00T 1.217(2) . ?
O00B C00J 1.345(3) . ?
O00B C01A 1.434(3) . ?
O00C C00U 1.345(3) . ?
O00C C01C 1.434(3) . ?
O00D C011 1.226(3) . ?
O00E C016 1.218(3) . ?
C00F C00G 1.395(3) . ?
C00F C00N 1.409(3) . ?
C00G H00G 0.9300 . ?
C00G C00M 1.408(3) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.341(3) . ?
C00H C016 1.459(3) . ?
C00I C00P 1.509(3) . ?
C00J C00X 1.402(3) . ?
C00J C00Y 1.395(3) . ?
C00K C00N 1.397(3) . ?
C00K C00Q 1.378(3) . ?
C00L C00X 1.396(3) . ?
C00L C012 1.379(3) . ?
C00M C00Q 1.402(3) . ?
C00N C00O 1.451(3) . ?
C00O C00V 1.558(3) . ?
C00P C00T 1.551(3) . ?
C00P C014 1.535(3) . ?
C00R H00A 0.9600 . ?
C00R H00B 0.9600 . ?
C00R H00C 0.9600 . ?
C00S C00V 1.515(3) . ?
C00S C010 1.351(3) . ?
C00T C00X 1.443(3) . ?
C00U C00Y 1.403(3) . ?
C00U C012 1.403(3) . ?
C00V C00W 1.529(3) . ?
C00W H00W 0.9800 . ?
C00W C00Z 1.526(3) . ?
C00W C013 1.529(3) . ?
C00Y H00Y 0.9300 . ?
C00Z H00D 0.9700 . ?
C00Z H00E 0.9700 . ?
C00Z C011 1.510(3) . ?
C010 H010 0.9300 . ?
C010 C011 1.452(3) . ?
C013 H01A 0.9600 . ?
C013 H01B 0.9600 . ?
C013 H01C 0.9600 . ?
C014 H014 0.9800 . ?
C014 C015 1.527(3) . ?
C014 C019 1.524(3) . ?
C015 H01J 0.9600 . ?
C015 H01K 0.9600 . ?
C015 H01L 0.9600 . ?
C016 C019 1.508(3) . ?
C017 H01D 0.9600 . ?
C017 H01E 0.9600 . ?
C017 H01F 0.9600 . ?
C018 H01M 0.9600 . ?
C018 H01N 0.9600 . ?
C018 H01O 0.9600 . ?
C019 H01P 0.9700 . ?
C019 H01Q 0.9700 . ?
C01A H01R 0.9600 . ?
C01A H01S 0.9600 . ?
C01A H01T 0.9600 . ?
C01B H01G 0.9600 . ?
C01B H01H 0.9600 . ?
C01B H01I 0.9600 . ?
C01C H01U 0.9600 . ?
C01C H01V 0.9600 . ?
C01C H01W 0.9600 . ?

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
C00K O003 C00V 108.11(14) . . ?
C00F O004 C00R 117.02(16) . . ?
C00L O005 C00P 107.89(14) . . ?
C00M O006 C01B 118.37(17) . . ?
C00I O007 C018 117.13(16) . . ?
C00S O009 C017 117.04(18) . . ?
C00J O00B C01A 117.26(17) . . ?
C00U O00C C01C 118.5(2) . . ?
O004 C00F C00G 124.40(18) . . ?
O004 C00F C00N 116.78(17) . . ?
C00G C00F C00N 118.82(18) . . ?
C00F C00G H00G 119.9 . . ?
C00F C00G C00M 120.14(19) . . ?
C00M C00G H00G 119.9 . . ?
C00I C00H H00H 119.1 . . ?
C00I C00H C016 121.82(19) . . ?
C016 C00H H00H 119.1 . . ?
O007 C00I C00P 110.02(16) . . ?
C00H C00I O007 126.96(18) . . ?
C00H C00I C00P 122.85(18) . . ?
O00B C00J C00X 115.76(17) . . ?
O00B C00J C00Y 125.14(18) . . ?
C00Y C00J C00X 119.10(19) . . ?
O003 C00K C00N 114.34(17) . . ?
O003 C00K C00Q 123.08(18) . . ?
C00Q C00K C00N 122.54(18) . . ?
O005 C00L C00X 114.04(17) . . ?
O005 C00L C012 124.04(18) . . ?
C012 C00L C00X 121.92(19) . . ?
O006 C00M C00G 123.61(18) . . ?
O006 C00M C00Q 115.21(18) . . ?
C00Q C00M C00G 121.18(19) . . ?
C00F C00N C00O 133.15(18) . . ?
C00K C00N C00F 119.61(18) . . ?
C00K C00N C00O 107.22(17) . . ?
O008 C00O C00N 131.58(19) . . ?
O008 C00O C00V 123.10(18) . . ?
C00N C00O C00V 105.31(16) . . ?
O005 C00P C00I 109.69(15) . . ?
O005 C00P C00T 105.15(14) . . ?
O005 C00P C014 107.77(15) . . ?
C00I C00P C00T 108.08(15) . . ?
C00I C00P C014 112.23(16) . . ?
C014 C00P C00T 113.65(16) . . ?
C00K C00Q Cl01 120.81(16) . . ?
C00K C00Q C00M 117.70(18) . . ?
C00M C00Q Cl01 121.43(16) . . ?
O004 C00R H00A 109.5 . . ?
O004 C00R H00B 109.5 . . ?
O004 C00R H00C 109.5 . . ?
H00A C00R H00B 109.5 . . ?
H00A C00R H00C 109.5 . . ?
H00B C00R H00C 109.5 . . ?
O009 C00S C00V 110.65(17) . . ?
O009 C00S C010 126.18(19) . . ?
C010 C00S C00V 123.14(19) . . ?
O00A C00T C00P 123.63(17) . . ?
O00A C00T C00X 131.14(18) . . ?
C00X C00T C00P 105.22(16) . . ?
O00C C00U C00Y 123.3(2) . . ?
O00C C00U C012 114.5(2) . . ?
C012 C00U C00Y 122.10(19) . . ?
O003 C00V C00O 104.85(15) . . ?
O003 C00V C00S 107.29(15) . . ?
O003 C00V C00W 107.96(14) . . ?
C00S C00V C00O 109.85(15) . . ?
C00S C00V C00W 112.35(16) . . ?
C00W C00V C00O 114.03(16) . . ?
C00V C00W H00W 107.4 . . ?
C00Z C00W C00V 110.56(16) . . ?
C00Z C00W H00W 107.4 . . ?
C00Z C00W C013 111.02(16) . . ?
C013 C00W C00V 112.86(16) . . ?
C013 C00W H00W 107.4 . . ?
C00J C00X C00T 132.22(18) . . ?
C00L C00X C00J 120.22(18) . . ?
C00L C00X C00T 107.57(17) . . ?
C00J C00Y C00U 119.28(19) . . ?
C00J C00Y H00Y 120.4 . . ?
C00U C00Y H00Y 120.4 . . ?
C00W C00Z H00D 108.9 . . ?
C00W C00Z H00E 108.9 . . ?
H00D C00Z H00E 107.7 . . ?
C011 C00Z C00W 113.48(17) . . ?
C011 C00Z H00D 108.9 . . ?
C011 C00Z H00E 108.9 . . ?
C00S C010 H010 119.1 . . ?
C00S C010 C011 121.89(19) . . ?
C011 C010 H010 119.1 . . ?
O00D C011 C00Z 121.5(2) . . ?
O00D C011 C010 121.5(2) . . ?
C010 C011 C00Z 116.94(19) . . ?
C00L C012 Cl02 121.99(17) . . ?
C00L C012 C00U 117.39(19) . . ?
C00U C012 Cl02 120.62(16) . . ?
C00W C013 H01A 109.5 . . ?
C00W C013 H01B 109.5 . . ?
C00W C013 H01C 109.5 . . ?
H01A C013 H01B 109.5 . . ?
H01A C013 H01C 109.5 . . ?
H01B C013 H01C 109.5 . . ?
C00P C014 H014 107.5 . . ?
C015 C014 C00P 112.89(17) . . ?
C015 C014 H014 107.5 . . ?
C019 C014 C00P 110.04(16) . . ?
C019 C014 H014 107.5 . . ?
C019 C014 C015 111.24(18) . . ?
C014 C015 H01J 109.5 . . ?
C014 C015 H01K 109.5 . . ?
C014 C015 H01L 109.5 . . ?
H01J C015 H01K 109.5 . . ?
H01J C015 H01L 109.5 . . ?
H01K C015 H01L 109.5 . . ?
O00E C016 C00H 121.6(2) . . ?
O00E C016 C019 121.3(2) . . ?
C00H C016 C019 116.97(18) . . ?
O009 C017 H01D 109.5 . . ?
O009 C017 H01E 109.5 . . ?
O009 C017 H01F 109.5 . . ?
H01D C017 H01E 109.5 . . ?
H01D C017 H01F 109.5 . . ?
H01E C017 H01F 109.5 . . ?
O007 C018 H01M 109.5 . . ?
O007 C018 H01N 109.5 . . ?
O007 C018 H01O 109.5 . . ?
H01M C018 H01N 109.5 . . ?
H01M C018 H01O 109.5 . . ?
H01N C018 H01O 109.5 . . ?
C014 C019 H01P 109.2 . . ?
C014 C019 H01Q 109.2 . . ?
C016 C019 C014 111.96(19) . . ?
C016 C019 H01P 109.2 . . ?
C016 C019 H01Q 109.2 . . ?
H01P C019 H01Q 107.9 . . ?
O00B C01A H01R 109.5 . . ?
O00B C01A H01S 109.5 . . ?
O00B C01A H01T 109.5 . . ?
H01R C01A H01S 109.5 . . ?
H01R C01A H01T 109.5 . . ?
H01S C01A H01T 109.5 . . ?
O006 C01B H01G 109.5 . . ?
O006 C01B H01H 109.5 . . ?
O006 C01B H01I 109.5 . . ?
H01G C01B H01H 109.5 . . ?
H01G C01B H01I 109.5 . . ?
H01H C01B H01I 109.5 . . ?
O00C C01C H01U 109.5 . . ?
O00C C01C H01V 109.5 . . ?
O00C C01C H01W 109.5 . . ?
H01U C01C H01V 109.5 . . ?
H01U C01C H01W 109.5 . . ?
H01V C01C H01W 109.5 . . ?

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
O003 C00K C00N C00F -177.45(17) . . . . ?
O003 C00K C00N C00O 1.2(2) . . . . ?
O003 C00K C00Q Cl01 0.6(3) . . . . ?
O003 C00K C00Q C00M 177.85(17) . . . . ?
O003 C00V C00W C00Z 163.42(15) . . . . ?
O003 C00V C00W C013 -71.6(2) . . . . ?
O004 C00F C00G C00M -178.68(18) . . . . ?
O004 C00F C00N C00K 178.84(17) . . . . ?
O004 C00F C00N C00O 0.6(3) . . . . ?
O005 C00L C00X C00J -179.62(18) . . . . ?
O005 C00L C00X C00T 0.4(2) . . . . ?
O005 C00L C012 Cl02 -0.5(3) . . . . ?
O005 C00L C012 C00U 179.13(19) . . . . ?
O005 C00P C00T O00A -175.43(18) . . . . ?
O005 C00P C00T C00X 3.49(19) . . . . ?
O005 C00P C014 C015 -66.7(2) . . . . ?
O005 C00P C014 C019 168.39(16) . . . . ?
O006 C00M C00Q Cl01 -2.2(3) . . . . ?
O006 C00M C00Q C00K -179.43(17) . . . . ?
O007 C00I C00P O005 43.2(2) . . . . ?
O007 C00I C00P C00T -70.89(19) . . . . ?
O007 C00I C00P C014 163.00(16) . . . . ?
O008 C00O C00V O003 175.37(17) . . . . ?
O008 C00O C00V C00S -69.6(2) . . . . ?
O008 C00O C00V C00W 57.5(2) . . . . ?
O009 C00S C00V O003 45.4(2) . . . . ?
O009 C00S C00V C00O -68.1(2) . . . . ?
O009 C00S C00V C00W 163.86(15) . . . . ?
O009 C00S C010 C011 173.45(19) . . . . ?
O00A C00T C00X C00J -3.6(4) . . . . ?
O00A C00T C00X C00L 176.4(2) . . . . ?
O00B C00J C00X C00L 179.89(18) . . . . ?
O00B C00J C00X C00T -0.2(3) . . . . ?
O00B C00J C00Y C00U -179.42(19) . . . . ?
O00C C00U C00Y C00J 178.2(2) . . . . ?
O00C C00U C012 Cl02 1.3(3) . . . . ?
O00C C00U C012 C00L -178.35(19) . . . . ?
O00E C016 C019 C014 -145.4(3) . . . . ?
C00F C00G C00M O006 178.60(18) . . . . ?
C00F C00G C00M C00Q -0.5(3) . . . . ?
C00F C00N C00O O008 1.2(4) . . . . ?
C00F C00N C00O C00V 180.0(2) . . . . ?
C00G C00F C00N C00K -1.0(3) . . . . ?
C00G C00F C00N C00O -179.2(2) . . . . ?
C00G C00M C00Q Cl01 177.01(15) . . . . ?
C00G C00M C00Q C00K -0.3(3) . . . . ?
C00H C00I C00P O005 -141.26(19) . . . . ?
C00H C00I C00P C00T 104.6(2) . . . . ?
C00H C00I C00P C014 -21.5(3) . . . . ?
C00H C016 C019 C014 36.7(3) . . . . ?
C00I C00H C016 O00E 173.0(3) . . . . ?
C00I C00H C016 C019 -9.2(4) . . . . ?
C00I C00P C00T O00A -58.3(2) . . . . ?
C00I C00P C00T C00X 120.59(17) . . . . ?
C00I C00P C014 C015 172.44(17) . . . . ?
C00I C00P C014 C019 47.5(2) . . . . ?
C00K O003 C00V C00O 4.33(18) . . . . ?
C00K O003 C00V C00S -112.44(16) . . . . ?
C00K O003 C00V C00W 126.26(16) . . . . ?
C00K C00N C00O O008 -177.2(2) . . . . ?
C00K C00N C00O C00V 1.6(2) . . . . ?
C00L O005 C00P C00I -119.29(17) . . . . ?
C00L O005 C00P C00T -3.29(19) . . . . ?
C00L O005 C00P C014 118.26(17) . . . . ?
C00N C00F C00G C00M 1.1(3) . . . . ?
C00N C00K C00Q Cl01 -176.88(15) . . . . ?
C00N C00K C00Q C00M 0.4(3) . . . . ?
C00N C00O C00V O003 -3.58(19) . . . . ?
C00N C00O C00V C00S 111.42(18) . . . . ?
C00N C00O C00V C00W -121.45(17) . . . . ?
C00O C00V C00W C00Z -80.5(2) . . . . ?
C00O C00V C00W C013 44.5(2) . . . . ?
C00P O005 C00L C00X 1.9(2) . . . . ?
C00P O005 C00L C012 -177.55(19) . . . . ?
C00P C00T C00X C00J 177.6(2) . . . . ?
C00P C00T C00X C00L -2.4(2) . . . . ?
C00P C014 C019 C016 -55.6(2) . . . . ?
C00Q C00K C00N C00F 0.2(3) . . . . ?
C00Q C00K C00N C00O 178.87(18) . . . . ?
C00R O004 C00F C00G 3.0(3) . . . . ?
C00R O004 C00F C00N -176.80(17) . . . . ?
C00S C00V C00W C00Z 45.3(2) . . . . ?
C00S C00V C00W C013 170.33(16) . . . . ?
C00S C010 C011 O00D -179.0(2) . . . . ?
C00S C010 C011 C00Z -2.7(3) . . . . ?
C00T C00P C014 C015 49.4(2) . . . . ?
C00T C00P C014 C019 -75.5(2) . . . . ?
C00V O003 C00K C00N -3.7(2) . . . . ?
C00V O003 C00K C00Q 178.69(17) . . . . ?
C00V C00S C010 C011 -4.6(3) . . . . ?
C00V C00W C00Z C011 -53.2(2) . . . . ?
C00W C00Z C011 O00D -151.5(2) . . . . ?
C00W C00Z C011 C010 32.2(3) . . . . ?
C00X C00J C00Y C00U 0.3(3) . . . . ?
C00X C00L C012 Cl02 -179.98(16) . . . . ?
C00X C00L C012 C00U -0.3(3) . . . . ?
C00Y C00J C00X C00L 0.1(3) . . . . ?
C00Y C00J C00X C00T -180.0(2) . . . . ?
C00Y C00U C012 Cl02 -179.54(16) . . . . ?
C00Y C00U C012 C00L 0.8(3) . . . . ?
C010 C00S C00V O003 -136.35(19) . . . . ?
C010 C00S C00V C00O 110.2(2) . . . . ?
C010 C00S C00V C00W -17.8(3) . . . . ?
C012 C00L C00X C00J -0.1(3) . . . . ?
C012 C00L C00X C00T 179.93(19) . . . . ?
C012 C00U C00Y C00J -0.8(3) . . . . ?
C013 C00W C00Z C011 -179.28(17) . . . . ?
C014 C00P C00T O00A 66.9(2) . . . . ?
C014 C00P C00T C00X -114.14(18) . . . . ?
C015 C014 C019 C016 178.58(19) . . . . ?
C016 C00H C00I O007 176.1(2) . . . . ?
C016 C00H C00I C00P 1.4(3) . . . . ?
C017 O009 C00S C00V 177.08(16) . . . . ?
C017 O009 C00S C010 -1.1(3) . . . . ?
C018 O007 C00I C00H -0.1(3) . . . . ?
C018 O007 C00I C00P 175.20(16) . . . . ?
C01A O00B C00J C00X 178.7(2) . . . . ?
C01A O00B C00J C00Y -1.6(3) . . . . ?
C01B O006 C00M C00G 1.1(3) . . . . ?
C01B O006 C00M C00Q -179.74(19) . . . . ?
C01C O00C C00U C00Y -0.3(3) . . . . ?
C01C O00C C00U C012 178.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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__Lorlatinib-298k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987322'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2020-06-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Lorlatinib
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 F N6 O2'
_chemical_formula_sum            'C21 H19 F N6 O2'
_chemical_formula_weight         406.42
_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 0.0181 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'
O O 0.0492 0.0322 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.16690(10)
_cell_length_b                   15.49550(10)
_cell_length_c                   18.85980(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3847.92(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17053
_cell_measurement_temperature    297.99(15)
_cell_measurement_theta_max      76.7220
_cell_measurement_theta_min      4.6850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36896
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.997
_diffrn_reflns_theta_min         4.689
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.99(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  61.00   0.50    3.94    --   46.62 -38.00 120.00  176
  2  ω     89.00 178.00   0.50   15.76    --  107.00  15.00  20.00  178
  3  ω     89.00 178.00   0.50   15.76    --  107.00  15.00  90.00  178
  4  ω     83.00 178.00   0.50   15.76    --  107.00  77.00-120.00  190
  5  ω     62.00 120.00   0.50    3.94    --   46.62 145.00-109.00  116
  6  ω     34.00 112.00   0.50   15.76    --  107.00-112.00  88.00  156
  7  ω     34.00 131.00   0.50   15.76    --  107.00 -77.00 120.00  194
  8  ω     34.00 125.00   0.50   15.76    --  107.00 -61.00 -90.00  182
  9  ω     34.00 109.00   0.50   15.76    --  107.00 -94.00  90.00  150
 10  ω     34.00 117.00   0.50   15.76    --  107.00-125.00  90.00  166
 11  ω     34.00 131.00   0.50   15.76    --  107.00 -77.00 150.00  194
 12  ω    -28.00  64.00   0.50    3.94    --   46.62 -15.00-149.00  184
 13  ω     32.00 123.00   0.50   15.76    --  107.00 -30.00-150.00  182
 14  ω     23.00 120.00   0.50    3.94    --   46.62  77.00-150.00  194
 15  ω   -119.00 -71.00   0.50    3.94    --  -46.62-125.00 120.00   96
 16  ω   -119.00 -71.00   0.50    3.94    --  -46.62-125.00-150.00   96
 17  ω   -130.00 -27.00   0.50   15.76    -- -100.00 145.00-109.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0842203000
_diffrn_orient_matrix_UB_12      0.0685322000
_diffrn_orient_matrix_UB_13      -0.0068296000
_diffrn_orient_matrix_UB_21      -0.0808305000
_diffrn_orient_matrix_UB_22      -0.0695423000
_diffrn_orient_matrix_UB_23      0.0150619000
_diffrn_orient_matrix_UB_31      0.0079794000
_diffrn_orient_matrix_UB_32      0.0188981000
_diffrn_orient_matrix_UB_33      0.0799679000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3345
_reflns_number_total             4036
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.061
_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)+(0.0668P)²+0.9995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N007(H00A,H00B)
2.b Ternary CH refined with riding coordinates:
 C00J(H00J)
2.c Secondary CH2 refined with riding coordinates:
 C00K(H00D,H00E)
2.d Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00M(H00M), C00O(H00O), C00Q(H00Q), C00R(H00R)
2.e Idealised Me refined as rotating group:
 C00S(H00F,H00G,H00H), C00T(H00I,H00K,H00L), C00U(H00N,H00P,H00S)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.31373(9) 0.64426(7) 0.31732(6) 0.0542(3) Uani 1 1 d . . . . .
O002 O 0.25279(9) 0.36346(8) 0.28268(7) 0.0603(3) Uani 1 1 d . . . . .
F003 F 0.43521(13) 0.62422(9) 0.05861(7) 0.0962(5) Uani 1 1 d . . . . .
N004 N 0.41933(10) 0.35533(8) 0.31140(7) 0.0485(3) Uani 1 1 d . . . . .
N005 N 0.64810(11) 0.33188(9) 0.38995(8) 0.0541(3) Uani 1 1 d . . . . .
N006 N 0.69818(11) 0.36499(9) 0.44493(8) 0.0543(3) Uani 1 1 d . . . . .
N007 N 0.38961(12) 0.78417(9) 0.38347(9) 0.0625(4) Uani 1 1 d . . . . .
H00A H 0.325706 0.775265 0.376128 0.075 Uiso 1 1 d R U . . .
H00B H 0.396695 0.811814 0.422949 0.075 Uiso 1 1 d R U . . .
C008 C 0.54259(11) 0.55292(9) 0.40208(8) 0.0432(3) Uani 1 1 d . . . . .
C009 C 0.40218(11) 0.63348(10) 0.35442(8) 0.0430(3) Uani 1 1 d . . . . .
C00A C 0.59677(11) 0.47031(10) 0.40829(8) 0.0438(3) Uani 1 1 d . . . . .
N00B N 0.52529(12) 0.70493(10) 0.42535(11) 0.0715(5) Uani 1 1 d . . . . .
C00C C 0.45229(11) 0.55712(10) 0.36320(8) 0.0450(3) Uani 1 1 d . . . . .
H00C H 0.425975 0.507127 0.343028 0.054 Uiso 1 1 calc R U . . .
C00D C 0.34099(12) 0.38618(10) 0.27240(8) 0.0468(3) Uani 1 1 d . . . . .
C00E C 0.33293(12) 0.53754(10) 0.22200(8) 0.0474(3) Uani 1 1 d . . . . .
C00F C 0.58645(12) 0.39468(10) 0.36657(8) 0.0461(3) Uani 1 1 d . . . . .
C00G C 0.36444(12) 0.45175(10) 0.21539(8) 0.0467(3) Uani 1 1 d . . . . .
C00H C 0.67090(12) 0.44813(11) 0.45744(8) 0.0482(4) Uani 1 1 d . . . . .
C00I C 0.43993(12) 0.70782(10) 0.38832(9) 0.0487(4) Uani 1 1 d . . . . .
C00J C 0.27047(12) 0.56795(11) 0.28465(9) 0.0504(4) Uani 1 1 d . . . . .
H00J H 0.267049 0.521625 0.319938 0.060 Uiso 1 1 calc R U . . .
C00K C 0.52706(13) 0.37610(10) 0.30009(9) 0.0492(4) Uani 1 1 d . . . . .
H00D H 0.531328 0.426017 0.269190 0.059 Uiso 1 1 calc R U . . .
H00E H 0.558874 0.328102 0.275665 0.059 Uiso 1 1 calc R U . . .
N00L N 0.76497(15) 0.53635(14) 0.55180(9) 0.0792(5) Uani 1 1 d . . . . .
C00M C 0.41526(15) 0.42508(12) 0.15486(9) 0.0578(4) Uani 1 1 d . . . . .
H00M H 0.433957 0.367480 0.150219 0.069 Uiso 1 1 calc R U . . .
C00N C 0.72114(13) 0.49733(13) 0.51049(9) 0.0566(4) Uani 1 1 d . . . . .
C00O C 0.35780(15) 0.59571(11) 0.16814(9) 0.0582(4) Uani 1 1 d . . . . .
H00O H 0.338900 0.653384 0.171628 0.070 Uiso 1 1 calc R U . . .
C00P C 0.41045(17) 0.56677(13) 0.11001(10) 0.0649(5) Uani 1 1 d . . . . .
C00Q C 0.43852(17) 0.48242(14) 0.10148(10) 0.0671(5) Uani 1 1 d . . . . .
H00Q H 0.472330 0.464311 0.060819 0.080 Uiso 1 1 calc R U . . .
C00R C 0.57494(15) 0.62923(12) 0.43085(12) 0.0662(5) Uani 1 1 d . . . . .
H00R H 0.635656 0.628773 0.456043 0.079 Uiso 1 1 calc R U . . .
C00S C 0.39776(16) 0.29083(12) 0.36609(11) 0.0664(5) Uani 1 1 d . . . . .
H00F H 0.391972 0.318793 0.411329 0.100 Uiso 1 1 calc R U . . .
H00G H 0.451971 0.249445 0.367646 0.100 Uiso 1 1 calc R U . . .
H00H H 0.335187 0.261949 0.355148 0.100 Uiso 1 1 calc R U . . .
C00T C 0.77039(16) 0.31276(14) 0.48454(12) 0.0717(5) Uani 1 1 d . . . . .
H00I H 0.737583 0.261044 0.500704 0.108 Uiso 1 1 calc R U . . .
H00K H 0.794712 0.344904 0.524604 0.108 Uiso 1 1 calc R U . . .
H00L H 0.826518 0.297853 0.454448 0.108 Uiso 1 1 calc R U . . .
C00U C 0.16357(15) 0.59310(14) 0.26323(12) 0.0715(5) Uani 1 1 d . . . . .
H00N H 0.124348 0.605580 0.304894 0.107 Uiso 1 1 calc R U . . .
H00P H 0.132641 0.546336 0.237764 0.107 Uiso 1 1 calc R U . . .
H00S H 0.166004 0.643311 0.233461 0.107 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.3689(18) . ?
O001 C00J 1.4499(19) . ?
O002 C00D 1.2289(19) . ?
F003 C00P 1.356(2) . ?
N004 C00D 1.354(2) . ?
N004 C00K 1.470(2) . ?
N004 C00S 1.464(2) . ?
N005 N006 1.332(2) . ?
N005 C00F 1.342(2) . ?
N006 C00H 1.358(2) . ?
N006 C00T 1.455(2) . ?
N007 H00A 0.8638 . ?
N007 H00B 0.8640 . ?
N007 C00I 1.359(2) . ?
C008 C00A 1.470(2) . ?
C008 C00C 1.398(2) . ?
C008 C00R 1.369(2) . ?
C009 C00C 1.365(2) . ?
C009 C00I 1.408(2) . ?
C00A C00F 1.418(2) . ?
C00A C00H 1.389(2) . ?
N00B C00I 1.324(2) . ?
N00B C00R 1.347(2) . ?
C00C H00C 0.9300 . ?
C00D C00G 1.511(2) . ?
C00E C00G 1.398(2) . ?
C00E C00J 1.515(2) . ?
C00E C00O 1.397(2) . ?
C00F C00K 1.505(2) . ?
C00G C00M 1.386(2) . ?
C00H C00N 1.421(2) . ?
C00J H00J 0.9800 . ?
C00J C00U 1.515(2) . ?
C00K H00D 0.9700 . ?
C00K H00E 0.9700 . ?
N00L C00N 1.143(2) . ?
C00M H00M 0.9300 . ?
C00M C00Q 1.377(3) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.372(3) . ?
C00P C00Q 1.368(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00F 0.9600 . ?
C00S H00G 0.9600 . ?
C00S H00H 0.9600 . ?
C00T H00I 0.9600 . ?
C00T H00K 0.9600 . ?
C00T H00L 0.9600 . ?
C00U H00N 0.9600 . ?
C00U H00P 0.9600 . ?
C00U H00S 0.9600 . ?

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
C009 O001 C00J 116.88(12) . . ?
C00D N004 C00K 125.36(13) . . ?
C00D N004 C00S 118.42(14) . . ?
C00S N004 C00K 116.04(14) . . ?
N006 N005 C00F 106.02(13) . . ?
N005 N006 C00H 111.71(13) . . ?
N005 N006 C00T 120.59(16) . . ?
C00H N006 C00T 127.69(16) . . ?
H00A N007 H00B 108.8 . . ?
C00I N007 H00A 110.3 . . ?
C00I N007 H00B 108.7 . . ?
C00C C008 C00A 119.66(13) . . ?
C00R C008 C00A 124.72(14) . . ?
C00R C008 C00C 115.60(14) . . ?
O001 C009 C00I 115.64(13) . . ?
C00C C009 O001 125.38(13) . . ?
C00C C009 C00I 118.91(14) . . ?
C00F C00A C008 128.97(14) . . ?
C00H C00A C008 127.55(14) . . ?
C00H C00A C00F 103.48(13) . . ?
C00I N00B C00R 118.82(15) . . ?
C008 C00C H00C 119.5 . . ?
C009 C00C C008 121.00(14) . . ?
C009 C00C H00C 119.5 . . ?
O002 C00D N004 122.20(15) . . ?
O002 C00D C00G 119.87(15) . . ?
N004 C00D C00G 117.92(14) . . ?
C00G C00E C00J 121.76(14) . . ?
C00O C00E C00G 118.63(15) . . ?
C00O C00E C00J 119.59(15) . . ?
N005 C00F C00A 111.04(14) . . ?
N005 C00F C00K 116.70(14) . . ?
C00A C00F C00K 132.06(14) . . ?
C00E C00G C00D 121.02(14) . . ?
C00M C00G C00D 118.95(14) . . ?
C00M C00G C00E 120.00(15) . . ?
N006 C00H C00A 107.74(14) . . ?
N006 C00H C00N 120.53(15) . . ?
C00A C00H C00N 131.61(16) . . ?
N007 C00I C009 120.63(14) . . ?
N00B C00I N007 118.60(14) . . ?
N00B C00I C009 120.77(15) . . ?
O001 C00J C00E 111.83(13) . . ?
O001 C00J H00J 109.1 . . ?
O001 C00J C00U 105.58(13) . . ?
C00E C00J H00J 109.1 . . ?
C00E C00J C00U 112.11(15) . . ?
C00U C00J H00J 109.1 . . ?
N004 C00K C00F 114.97(13) . . ?
N004 C00K H00D 108.5 . . ?
N004 C00K H00E 108.5 . . ?
C00F C00K H00D 108.5 . . ?
C00F C00K H00E 108.5 . . ?
H00D C00K H00E 107.5 . . ?
C00G C00M H00M 119.4 . . ?
C00Q C00M C00G 121.13(17) . . ?
C00Q C00M H00M 119.4 . . ?
N00L C00N C00H 177.4(2) . . ?
C00E C00O H00O 120.4 . . ?
C00P C00O C00E 119.23(17) . . ?
C00P C00O H00O 120.4 . . ?
F003 C00P C00O 118.55(19) . . ?
F003 C00P C00Q 118.58(18) . . ?
C00Q C00P C00O 122.87(17) . . ?
C00M C00Q H00Q 121.0 . . ?
C00P C00Q C00M 118.06(17) . . ?
C00P C00Q H00Q 121.0 . . ?
C008 C00R H00R 117.6 . . ?
N00B C00R C008 124.80(16) . . ?
N00B C00R H00R 117.6 . . ?
N004 C00S H00F 109.5 . . ?
N004 C00S H00G 109.5 . . ?
N004 C00S H00H 109.5 . . ?
H00F C00S H00G 109.5 . . ?
H00F C00S H00H 109.5 . . ?
H00G C00S H00H 109.5 . . ?
N006 C00T H00I 109.5 . . ?
N006 C00T H00K 109.5 . . ?
N006 C00T H00L 109.5 . . ?
H00I C00T H00K 109.5 . . ?
H00I C00T H00L 109.5 . . ?
H00K C00T H00L 109.5 . . ?
C00J C00U H00N 109.5 . . ?
C00J C00U H00P 109.5 . . ?
C00J C00U H00S 109.5 . . ?
H00N C00U H00P 109.5 . . ?
H00N C00U H00S 109.5 . . ?
H00P C00U H00S 109.5 . . ?

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
O001 C009 C00C C008 179.85(14) . . . . ?
O001 C009 C00I N007 0.1(2) . . . . ?
O001 C009 C00I N00B -179.61(16) . . . . ?
O002 C00D C00G C00E 68.0(2) . . . . ?
O002 C00D C00G C00M -110.00(19) . . . . ?
F003 C00P C00Q C00M 178.37(18) . . . . ?
N004 C00D C00G C00E -111.05(18) . . . . ?
N004 C00D C00G C00M 71.0(2) . . . . ?
N005 N006 C00H C00A 1.19(18) . . . . ?
N005 N006 C00H C00N -175.21(15) . . . . ?
N005 C00F C00K N004 103.39(16) . . . . ?
N006 N005 C00F C00A -0.48(18) . . . . ?
N006 N005 C00F C00K 174.98(13) . . . . ?
C008 C00A C00F N005 -178.67(14) . . . . ?
C008 C00A C00F C00K 6.8(3) . . . . ?
C008 C00A C00H N006 178.47(14) . . . . ?
C008 C00A C00H C00N -5.7(3) . . . . ?
C009 O001 C00J C00E -71.03(18) . . . . ?
C009 O001 C00J C00U 166.79(15) . . . . ?
C00A C008 C00C C009 -177.69(14) . . . . ?
C00A C008 C00R N00B -179.84(19) . . . . ?
C00A C00F C00K N004 -82.3(2) . . . . ?
C00C C008 C00A C00F 17.3(2) . . . . ?
C00C C008 C00A C00H -162.51(15) . . . . ?
C00C C008 C00R N00B 1.5(3) . . . . ?
C00C C009 C00I N007 -177.01(16) . . . . ?
C00C C009 C00I N00B 3.2(3) . . . . ?
C00D N004 C00K C00F 136.50(15) . . . . ?
C00D C00G C00M C00Q -179.88(17) . . . . ?
C00E C00G C00M C00Q 2.1(3) . . . . ?
C00E C00O C00P F003 -179.14(17) . . . . ?
C00E C00O C00P C00Q 1.2(3) . . . . ?
C00F N005 N006 C00H -0.44(18) . . . . ?
C00F N005 N006 C00T 178.35(16) . . . . ?
C00F C00A C00H N006 -1.36(16) . . . . ?
C00F C00A C00H C00N 174.48(17) . . . . ?
C00G C00E C00J O001 129.39(16) . . . . ?
C00G C00E C00J C00U -112.25(18) . . . . ?
C00G C00E C00O C00P 1.2(3) . . . . ?
C00G C00M C00Q C00P 0.3(3) . . . . ?
C00H C00A C00F N005 1.16(17) . . . . ?
C00H C00A C00F C00K -173.38(16) . . . . ?
C00I C009 C00C C008 -3.3(2) . . . . ?
C00I N00B C00R C008 -1.6(4) . . . . ?
C00J O001 C009 C00C -0.2(2) . . . . ?
C00J O001 C009 C00I -177.16(14) . . . . ?
C00J C00E C00G C00D -2.6(2) . . . . ?
C00J C00E C00G C00M 175.39(15) . . . . ?
C00J C00E C00O C00P -177.06(16) . . . . ?
C00K N004 C00D O002 176.86(15) . . . . ?
C00K N004 C00D C00G -4.1(2) . . . . ?
C00O C00E C00G C00D 179.18(14) . . . . ?
C00O C00E C00G C00M -2.9(2) . . . . ?
C00O C00E C00J O001 -52.4(2) . . . . ?
C00O C00E C00J C00U 66.0(2) . . . . ?
C00O C00P C00Q C00M -2.0(3) . . . . ?
C00R C008 C00A C00F -161.32(18) . . . . ?
C00R C008 C00A C00H 18.9(3) . . . . ?
C00R C008 C00C C009 1.0(2) . . . . ?
C00R N00B C00I N007 179.4(2) . . . . ?
C00R N00B C00I C009 -0.8(3) . . . . ?
C00S N004 C00D O002 1.9(2) . . . . ?
C00S N004 C00D C00G -179.11(14) . . . . ?
C00S N004 C00K C00F -48.41(19) . . . . ?
C00T N006 C00H C00A -177.49(17) . . . . ?
C00T N006 C00H C00N 6.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.787
####################################################################### 
# 
# 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_Gefitinib-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987320'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-25
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Gefitinib
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl F N4 O3'
_chemical_formula_sum            'C22 H24 Cl F N4 O3'
_chemical_formula_weight         446.90
_chemical_melting_point          468.5
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'
O O 0.0492 0.0322 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   8.81100(10)
_cell_length_b                   9.6610(2)
_cell_length_c                   12.4893(2)
_cell_angle_alpha                93.6600(10)
_cell_angle_beta                 97.5860(10)
_cell_angle_gamma                101.8710(10)
_cell_volume                     1026.74(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    26680
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9180
_cell_measurement_theta_min      3.5890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.013
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40850
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.110
_diffrn_reflns_theta_min         3.586
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00  -9.00   0.50    0.09    --  -46.62 123.00 -63.00  170
  2  ω   -119.00 -55.00   0.50    0.09    --  -46.62-149.00  52.00  128
  3  ω   -109.00 -23.00   0.50    0.09    --  -46.62 149.00  99.00  172
  4  ω   -119.00 -73.00   0.50    0.09    --  -46.62-123.00-143.00   92
  5  ω     14.00  94.00   0.50    0.09    --   46.62-123.00-143.00  160
  6  ω     28.00 110.00   0.50    0.09    --   46.62-149.00  52.00  164
  7  ω     59.00 120.00   0.50    0.09    --   46.62 149.00  99.00  122
  8  ω   -171.00 -55.00   0.50    0.37    -- -100.00-149.00  52.00  232
  9  ω   -115.00 -27.00   0.50    0.37    -- -100.00 123.00 -63.00  176
 10  ω   -173.00 -73.00   0.50    0.37    -- -100.00-123.00-143.00  200
 11  ω     34.00 115.00   0.50    0.37    --  107.00-123.00-143.00  162
 12  ω     59.00 172.00   0.50    0.37    --  107.00 149.00  99.00  226
 13  ω     34.00 133.00   0.50    0.37    --  107.00-149.00  52.00  198
 14  ω     77.00 178.00   0.50    0.37    --  107.00 123.00 -63.00  202
 15  ω    -22.00   4.00   0.50    0.09    --   16.00 106.00 165.43   52
 16  ω      9.00  43.00   0.50    0.09    --   40.00  92.00 -77.20   68
 17  ω     14.00  44.00   0.50    0.09    --   44.00  91.00  28.95   60
 18  ω     14.00  45.00   0.50    0.09    --   44.00  90.00 -16.87   62
 19  ω   -119.00 -30.00   0.50    0.09    --  -46.62 -57.00-180.00  178
 20  ω   -119.00 -23.00   0.50    0.09    --  -46.62 -77.00-120.00  192
 21  ω     32.00 120.00   0.50    0.09    --   46.62  38.00 -60.00  176
 22  ω     32.00 120.00   0.50    0.09    --   46.62  38.00  30.00  176
 23  ω     24.00 121.00   0.50    0.09    --   48.00  78.00-168.92  194
 24  ω     18.00  43.00   0.50    0.09    --   48.00  90.00  88.79   50
 25  ω     25.00  77.00   0.50    0.09    --   48.00  80.00-144.97  104
 26  ω     73.00  99.00   0.50    0.09    --   52.00  82.00-107.92   52
 27  ω     26.00  52.00   0.50    0.09    --   52.00  82.00-107.92   52
 28  ω     32.00  67.00   0.50    0.09    --   56.00  78.00  22.19   70
 29  ω     36.00  79.00   0.50    0.09    --   56.00  72.00 153.70   86
 30  ω    -71.00 -45.00   0.50    0.09    --  -60.00 -70.00-106.85   52
 31  ω   -118.00 -92.00   0.50    0.09    --  -60.00 -70.00-106.85   52
 32  ω    -62.00 -36.00   0.50    0.09    --  -60.00 -79.00  65.89   52
 33  ω   -119.00 -93.00   0.50    0.09    --  -60.00 -79.00  65.89   52
 34  ω     37.00  65.00   0.50    0.09    --   60.00  75.00  58.58   56
 35  ω     40.00  73.00   0.50    0.09    --   64.00  78.00 111.23   66
 36  ω    -81.00 -46.00   0.50    0.09    --  -68.00 -73.00  12.68   70
 37  ω    -74.00 -43.00   0.50    0.09    --  -68.00 -83.00  61.40   62
 38  ω    -67.00 -42.00   0.50    0.09    --  -68.00 -81.00-167.34   50
 39  ω    -78.00 -45.00   0.50    0.09    --  -68.00 -75.00 -66.47   66
 40  ω    -73.00 -41.00   0.50    0.09    --  -68.00 -83.00-176.25   64
 41  ω    -86.00 -44.00   0.50    0.09    --  -68.00 -78.00 -28.19   84
 42  ω     42.00  68.00   0.50    0.09    --   68.00  83.00 151.63   52
 43  ω    -77.00 -47.00   0.50    0.09    --  -72.00 -80.00-108.11   60
 44  ω    -70.00 -45.00   0.50    0.09    --  -72.00 -83.00 111.37   50
 45  ω    -79.00 -51.00   0.50    0.09    --  -72.00 -69.00 -86.03   56
 46  ω     49.00  75.00   0.50    0.09    --   72.00  76.00  32.28   52
 47  ω    -80.00 -54.00   0.50    0.37    --  -80.00 -83.00-118.62   52
 48  ω    -83.00 -57.00   0.50    0.37    --  -80.00 -74.00  73.58   52
 49  ω    -79.00 -53.00   0.50    0.37    --  -80.00 -83.00  24.29   52
 50  ω    -85.00 -59.00   0.50    0.37    --  -80.00 -73.00  38.92   52
 51  ω    -90.00 -63.00   0.50    0.37    --  -84.00 -69.00-107.37   54
 52  ω    -96.00 -70.00   0.50    0.37    --  -88.00 -62.00-158.57   52
 53  ω    -97.00 -65.00   0.50    0.37    --  -88.00 -76.00 164.50   64
 54  ω    -90.00 -65.00   0.50    0.37    --  -88.00 -75.00 173.46   50
 55  ω    -91.00 -65.00   0.50    0.37    --  -88.00 -74.00 -55.23   52
 56  ω   -100.00 -72.00   0.50    0.37    --  -92.00 -68.00 -33.46   56
 57  ω    -99.00 -73.00   0.50    0.37    --  -92.00 -65.00 -53.65   52
 58  ω    -98.00 -72.00   0.50    0.37    --  -92.00 -74.00  23.23   52
 59  ω    -99.00 -73.00   0.50    0.37    --  -96.00 -76.00  -2.50   52
 60  ω   -104.00 -76.00   0.50    0.37    --  -96.00 -68.00 152.52   56
 61  ω   -143.00 -76.00   0.50    0.37    --  -96.00 -74.00  67.07  134
 62  ω   -158.00-132.00   0.50    0.37    --  -96.00 -76.00  -2.50   52
 63  ω   -139.00-114.00   0.50    0.37    --  -96.00 -68.00 152.52   50
 64  ω    -95.00 -70.00   0.50    0.37    --  -96.00 -81.00 -62.86   50
 65  ω   -160.00-134.00   0.50    0.37    --  -96.00 -81.00 -62.86   52
 66  ω    -99.00 -73.00   0.50    0.37    --  -96.00 -76.00-118.01   52
 67  ω   -137.00 -78.00   0.50    0.37    -- -100.00 -74.00-178.12  118
 68  ω   -173.00-142.00   0.50    0.37    -- -100.00 -74.00-178.12   62
 69  ω   -122.00 -76.00   0.50    0.37    -- -100.00 -77.00  60.00   92
 70  ω   -131.00 -79.00   0.50    0.37    -- -100.00 -70.00   7.54  104
 71  ω   -103.00 -74.00   0.50    0.37    -- -100.00 -83.00  58.28   58
 72  ω   -171.00 -82.00   0.50    0.37    -- -100.00 -61.00 120.00  178
 73  ω   -103.00 -76.00   0.50    0.37    -- -100.00 -78.00-151.07   54
 74  ω   -164.00-138.00   0.50    0.37    -- -100.00 -78.00-151.07   52
 75  ω   -162.00-126.00   0.50    0.37    -- -100.00 -83.00  58.28   72
 76  ω   -110.00 -74.00   0.50    0.37    -- -100.00 -81.00  87.95   72
 77  ω   -105.00 -76.00   0.50    0.37    -- -100.00 -79.00  13.55   58
 78  ω   -102.00 -76.00   0.50    0.37    -- -100.00 -76.00 125.30   52
 79  ω   -101.00 -76.00   0.50    0.37    -- -100.00 -77.00  30.00   50
 80  ω   -102.00 -76.00   0.50    0.37    -- -100.00 -77.00-120.00   52
 81  ω   -147.00-121.00   0.50    0.37    -- -100.00 -77.00-120.00   52
 82  ω   -115.00 -79.00   0.50    0.37    -- -100.00 -74.00 -11.82   72
 83  ω   -163.00-120.00   0.50    0.37    -- -100.00 -74.00 -11.82   86
 84  ω   -113.00 -79.00   0.50    0.37    -- -100.00 -72.00  93.48   68
 85  ω   -106.00 -80.00   0.50    0.37    -- -100.00 -67.00 -56.69   52
 86  ω   -101.00 -76.00   0.50    0.37    -- -100.00 -76.00 159.92   50
 87  ω   -170.00 -76.00   0.50    0.37    -- -100.00 -77.00  90.00  188
 88  ω   -102.00 -76.00   0.50    0.37    -- -100.00 -77.00 -90.00   52
 89  ω   -144.00-118.00   0.50    0.37    -- -100.00 -76.00 159.92   52
 90  ω   -172.00-106.00   0.50    0.37    -- -100.00 -94.00-120.00  132
 91  ω   -164.00-139.00   0.50    0.37    -- -100.00 -77.00 -90.00   50
 92  ω   -106.00 -80.00   0.50    0.37    -- -100.00 -73.00-164.61   52
 93  ω   -124.00 -98.00   0.50    0.37    -- -100.00 -62.00 -94.97   52
 94  ω   -173.00-109.00   0.50    0.37    -- -100.00 -73.00-164.61  128
 95  ω   -172.00 -79.00   0.50    0.37    -- -100.00 -70.00 142.79  186
 96  ω   -173.00-130.00   0.50    0.37    -- -100.00 -62.00 -94.97   86
 97  ω   -111.00 -81.00   0.50    0.37    -- -100.00 -65.00-115.70   60
 98  ω   -102.00 -77.00   0.50    0.37    -- -100.00 -75.00 -37.77   50
 99  ω   -167.00-106.00   0.50    0.37    -- -100.00 -75.00 -37.77  122
100  ω   -104.00 -79.00   0.50    0.37    -- -100.00 149.00  99.00   50
101  ω   -103.00 -77.00   0.50    0.37    -- -100.00 -78.00 115.15   52
102  ω     90.00 177.00   0.50    0.37    --  107.00  61.00-120.00  174
103  ω     34.00  82.00   0.50    0.37    --  107.00 -94.00  30.00   96
104  ω    114.00 145.00   0.50    0.37    --  107.00  30.00  90.00   62
105  ω     34.00  94.00   0.50    0.37    --  107.00 -61.00-150.00  120
106  ω     83.00 108.00   0.50    0.37    --  107.00 -94.00  90.00   50
107  ω     34.00  79.00   0.50    0.37    --  107.00 -94.00  90.00   90
108  ω     84.00 177.00   0.50    0.37    --  107.00  77.00 -30.00  186
109  ω     84.00 117.00   0.50    0.37    --  107.00-125.00 -30.00   66
110  ω     37.00  79.00   0.50    0.37    --  107.00-125.00 -30.00   84
111  ω    106.00 131.00   0.50    0.37    --  107.00 -77.00 120.00   50
112  ω     35.00  92.00   0.50    0.37    --  107.00 -77.00 120.00  114
113  ω    121.00 166.00   0.50    0.37    --  107.00  77.00-150.00   90
114  ω     83.00 112.00   0.50    0.37    --  107.00  77.00-150.00   58
115  ω     90.00 116.00   0.50    0.37    --  107.00-125.00 -60.00   52
116  ω     38.00  64.00   0.50    0.37    --  107.00-125.00 -60.00   52
117  ω     75.00 101.00   0.50    0.37    --  107.00 -94.00 120.00   52
118  ω     34.00  98.00   0.50    0.37    --  107.00 -61.00 -60.00  128
119  ω     38.00  69.00   0.50    0.37    --  107.00 -94.00 120.00   62
120  ω     85.00 162.00   0.50    0.37    --  107.00  77.00   0.00  154
121  ω     71.00 108.00   0.50    0.37    --  107.00 -94.00  60.00   74
122  ω    140.00 170.00   0.50    0.37    --  107.00  77.00 -90.00   60
123  ω     84.00 125.00   0.50    0.37    --  107.00  77.00 -90.00   82
124  ω     37.00  65.00   0.50    0.37    --  107.00 -94.00  60.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1674044000
_diffrn_orient_matrix_UB_12      0.0915689000
_diffrn_orient_matrix_UB_13      0.0299380000
_diffrn_orient_matrix_UB_21      -0.0198104000
_diffrn_orient_matrix_UB_22      0.0059289000
_diffrn_orient_matrix_UB_23      0.1208206000
_diffrn_orient_matrix_UB_31      0.0650083000
_diffrn_orient_matrix_UB_32      -0.1355260000
_diffrn_orient_matrix_UB_33      0.0113544000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3892
_reflns_number_total             4234
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.089
_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)+(0.0484P)²+0.3245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00N(H00C,H00D), C00O(H00E,H00G), C00Q(H00I,H00J), C00S(H00Q,
 H00R), C00T(H00S,H00T), C00V(H00V,H00W)
2.b Aromatic/amide H refined with riding coordinates:
 N008(H008), C00F(H00F), C00H(H00H), C00K(H00K), C00M(H00M), C00P(H00P),
 C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00R(H00L,H00N,H00O)
;
_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
Cl01 Cl 1.13709(4) 0.15973(4) 0.07212(3) 0.03055(11) Uani 1 1 d . . . . .
F002 F 1.11133(10) -0.08770(8) 0.19894(6) 0.02813(19) Uani 1 1 d . . . . .
O003 O 0.63881(10) 0.80126(9) 0.34035(7) 0.01893(19) Uani 1 1 d . . . . .
O004 O 0.24157(10) 0.54545(9) -0.15146(7) 0.02016(19) Uani 1 1 d . . . . .
O005 O 0.56911(11) 0.85899(9) 0.52750(7) 0.0215(2) Uani 1 1 d . . . . .
N006 N 0.40192(12) 0.71103(11) 0.04373(8) 0.0175(2) Uani 1 1 d . . . . .
N007 N 0.84901(12) 0.30341(11) 0.54646(8) 0.0198(2) Uani 1 1 d . . . . .
N008 N 0.87282(12) 0.35127(11) 0.36780(8) 0.0179(2) Uani 1 1 d . . . . .
H008 H 0.860798 0.410499 0.320474 0.022 Uiso 1 1 calc R U . . .
N009 N 0.73979(12) 0.45113(11) 0.66427(8) 0.0204(2) Uani 1 1 d . . . . .
C00A C 0.76164(13) 0.50626(12) 0.47851(9) 0.0165(2) Uani 1 1 d . . . . .
C00B C 0.62864(13) 0.74097(13) 0.51919(10) 0.0174(2) Uani 1 1 d . . . . .
C00C C 0.71783(13) 0.53500(13) 0.58075(9) 0.0171(2) Uani 1 1 d . . . . .
C00D C 0.82861(13) 0.38440(12) 0.46609(9) 0.0164(2) Uani 1 1 d . . . . .
C00E C 0.67008(13) 0.70981(12) 0.41462(9) 0.0167(2) Uani 1 1 d . . . . .
C00F C 0.99789(14) 0.25017(13) 0.23521(10) 0.0186(2) Uani 1 1 d . . . . .
H00F H 1.000434 0.332813 0.200532 0.022 Uiso 1 1 calc R U . . .
C00G C 0.67172(14) 0.77043(13) 0.23271(9) 0.0181(2) Uani 1 1 d . . . . .
H00A H 0.617992 0.674608 0.204200 0.022 Uiso 1 1 calc R U . . .
H00B H 0.783476 0.778941 0.233380 0.022 Uiso 1 1 calc R U . . .
C00H C 0.73603(13) 0.59621(13) 0.39555(9) 0.0170(2) Uani 1 1 d . . . . .
H00H H 0.764327 0.577689 0.327797 0.020 Uiso 1 1 calc R U . . .
C00I C 0.93437(13) 0.23659(13) 0.33203(9) 0.0172(2) Uani 1 1 d . . . . .
C00J C 1.05668(14) 0.14132(13) 0.19114(10) 0.0200(2) Uani 1 1 d . . . . .
C00K C 0.93221(14) 0.11233(13) 0.38393(10) 0.0194(2) Uani 1 1 d . . . . .
H00K H 0.889376 0.101708 0.447873 0.023 Uiso 1 1 calc R U . . .
C00L C 1.05449(14) 0.01902(13) 0.24350(10) 0.0203(2) Uani 1 1 d . . . . .
C00M C 0.65123(13) 0.65397(13) 0.59971(9) 0.0179(2) Uani 1 1 d . . . . .
H00M H 0.622563 0.673323 0.667204 0.022 Uiso 1 1 calc R U . . .
C00N C 0.43677(14) 0.83185(13) 0.12702(10) 0.0200(2) Uani 1 1 d . . . . .
H00C H 0.384419 0.805231 0.188617 0.024 Uiso 1 1 calc R U . . .
H00D H 0.397584 0.910613 0.097890 0.024 Uiso 1 1 calc R U . . .
C00O C 0.61348(14) 0.87768(13) 0.16395(9) 0.0190(2) Uani 1 1 d . . . . .
H00E H 0.667205 0.886815 0.100957 0.023 Uiso 1 1 calc R U . . .
H00G H 0.637165 0.969711 0.205630 0.023 Uiso 1 1 calc R U . . .
C00P C 0.99445(15) 0.00483(13) 0.33939(10) 0.0208(3) Uani 1 1 d . . . . .
H00P H 0.995524 -0.077043 0.374548 0.025 Uiso 1 1 calc R U . . .
C00Q C 0.39644(14) 0.63059(14) -0.14531(10) 0.0216(3) Uani 1 1 d . . . . .
H00I H 0.412027 0.662067 -0.216047 0.026 Uiso 1 1 calc R U . . .
H00J H 0.472785 0.574109 -0.124485 0.026 Uiso 1 1 calc R U . . .
C00R C 0.52295(15) 0.89760(14) 0.62885(10) 0.0218(3) Uani 1 1 d . . . . .
H00L H 0.486901 0.984641 0.624832 0.033 Uiso 1 1 calc R U . . .
H00N H 0.611000 0.910354 0.685456 0.033 Uiso 1 1 calc R U . . .
H00O H 0.439954 0.823717 0.644310 0.033 Uiso 1 1 calc R U . . .
C00S C 0.42119(15) 0.75832(13) -0.06344(9) 0.0205(3) Uani 1 1 d . . . . .
H00Q H 0.525684 0.816196 -0.061298 0.025 Uiso 1 1 calc R U . . .
H00R H 0.345843 0.815685 -0.084489 0.025 Uiso 1 1 calc R U . . .
C00T C 0.24350(14) 0.62458(14) 0.03833(10) 0.0222(3) Uani 1 1 d . . . . .
H00S H 0.167031 0.681792 0.019918 0.027 Uiso 1 1 calc R U . . .
H00T H 0.229455 0.590390 0.108489 0.027 Uiso 1 1 calc R U . . .
C00U C 0.80277(15) 0.34342(13) 0.64068(10) 0.0214(3) Uani 1 1 d . . . . .
H00U H 0.817841 0.286367 0.696649 0.026 Uiso 1 1 calc R U . . .
C00V C 0.21821(15) 0.49956(14) -0.04673(10) 0.0224(3) Uani 1 1 d . . . . .
H00V H 0.290581 0.439517 -0.025456 0.027 Uiso 1 1 calc R U . . .
H00W H 0.112398 0.443548 -0.050838 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00J 1.7330(12) . ?
F002 C00L 1.3552(14) . ?
O003 C00E 1.3617(14) . ?
O003 C00G 1.4379(14) . ?
O004 C00Q 1.4307(14) . ?
O004 C00V 1.4344(14) . ?
O005 C00B 1.3533(15) . ?
O005 C00R 1.4300(14) . ?
N006 C00N 1.4670(15) . ?
N006 C00S 1.4612(15) . ?
N006 C00T 1.4625(15) . ?
N007 C00D 1.3276(15) . ?
N007 C00U 1.3541(16) . ?
N008 H008 0.8600 . ?
N008 C00D 1.3742(15) . ?
N008 C00I 1.4033(16) . ?
N009 C00C 1.3788(15) . ?
N009 C00U 1.3111(17) . ?
C00A C00C 1.4091(16) . ?
C00A C00D 1.4300(17) . ?
C00A C00H 1.4190(16) . ?
C00B C00E 1.4319(16) . ?
C00B C00M 1.3716(17) . ?
C00C C00M 1.4146(17) . ?
C00E C00H 1.3654(17) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.4004(17) . ?
C00F C00J 1.3794(17) . ?
C00G H00A 0.9700 . ?
C00G H00B 0.9700 . ?
C00G C00O 1.5134(16) . ?
C00H H00H 0.9300 . ?
C00I C00K 1.3982(17) . ?
C00J C00L 1.3844(18) . ?
C00K H00K 0.9300 . ?
C00K C00P 1.3892(18) . ?
C00L C00P 1.3752(18) . ?
C00M H00M 0.9300 . ?
C00N H00C 0.9700 . ?
C00N H00D 0.9700 . ?
C00N C00O 1.5276(17) . ?
C00O H00E 0.9700 . ?
C00O H00G 0.9700 . ?
C00P H00P 0.9300 . ?
C00Q H00I 0.9700 . ?
C00Q H00J 0.9700 . ?
C00Q C00S 1.5117(17) . ?
C00R H00L 0.9600 . ?
C00R H00N 0.9600 . ?
C00R H00O 0.9600 . ?
C00S H00Q 0.9700 . ?
C00S H00R 0.9700 . ?
C00T H00S 0.9700 . ?
C00T H00T 0.9700 . ?
C00T C00V 1.5165(18) . ?
C00U H00U 0.9300 . ?
C00V H00V 0.9700 . ?
C00V H00W 0.9700 . ?

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
C00E O003 C00G 116.68(9) . . ?
C00Q O004 C00V 109.53(9) . . ?
C00B O005 C00R 117.86(9) . . ?
C00S N006 C00N 111.23(9) . . ?
C00S N006 C00T 108.62(9) . . ?
C00T N006 C00N 112.79(9) . . ?
C00D N007 C00U 115.92(11) . . ?
C00D N008 H008 114.7 . . ?
C00D N008 C00I 130.55(10) . . ?
C00I N008 H008 114.7 . . ?
C00U N009 C00C 114.94(10) . . ?
C00C C00A C00D 116.16(11) . . ?
C00C C00A C00H 119.35(11) . . ?
C00H C00A C00D 124.48(11) . . ?
O005 C00B C00E 113.96(10) . . ?
O005 C00B C00M 126.21(11) . . ?
C00M C00B C00E 119.83(11) . . ?
N009 C00C C00A 121.84(11) . . ?
N009 C00C C00M 118.51(11) . . ?
C00A C00C C00M 119.64(11) . . ?
N007 C00D N008 119.58(11) . . ?
N007 C00D C00A 121.90(11) . . ?
N008 C00D C00A 118.53(10) . . ?
O003 C00E C00B 114.69(10) . . ?
O003 C00E C00H 124.97(11) . . ?
C00H C00E C00B 120.34(11) . . ?
C00I C00F H00F 119.9 . . ?
C00J C00F H00F 119.9 . . ?
C00J C00F C00I 120.19(11) . . ?
O003 C00G H00A 110.4 . . ?
O003 C00G H00B 110.4 . . ?
O003 C00G C00O 106.50(9) . . ?
H00A C00G H00B 108.6 . . ?
C00O C00G H00A 110.4 . . ?
C00O C00G H00B 110.4 . . ?
C00A C00H H00H 119.8 . . ?
C00E C00H C00A 120.38(11) . . ?
C00E C00H H00H 119.8 . . ?
C00F C00I N008 115.60(11) . . ?
C00K C00I N008 124.94(11) . . ?
C00K C00I C00F 119.44(11) . . ?
C00F C00J Cl01 119.91(10) . . ?
C00F C00J C00L 119.85(11) . . ?
C00L C00J Cl01 120.22(10) . . ?
C00I C00K H00K 120.2 . . ?
C00P C00K C00I 119.59(11) . . ?
C00P C00K H00K 120.2 . . ?
F002 C00L C00J 119.32(11) . . ?
F002 C00L C00P 120.02(11) . . ?
C00P C00L C00J 120.66(12) . . ?
C00B C00M C00C 120.43(11) . . ?
C00B C00M H00M 119.8 . . ?
C00C C00M H00M 119.8 . . ?
N006 C00N H00C 109.6 . . ?
N006 C00N H00D 109.6 . . ?
N006 C00N C00O 110.28(10) . . ?
H00C C00N H00D 108.1 . . ?
C00O C00N H00C 109.6 . . ?
C00O C00N H00D 109.6 . . ?
C00G C00O C00N 110.77(10) . . ?
C00G C00O H00E 109.5 . . ?
C00G C00O H00G 109.5 . . ?
C00N C00O H00E 109.5 . . ?
C00N C00O H00G 109.5 . . ?
H00E C00O H00G 108.1 . . ?
C00K C00P H00P 119.9 . . ?
C00L C00P C00K 120.25(11) . . ?
C00L C00P H00P 119.9 . . ?
O004 C00Q H00I 109.5 . . ?
O004 C00Q H00J 109.5 . . ?
O004 C00Q C00S 110.62(10) . . ?
H00I C00Q H00J 108.1 . . ?
C00S C00Q H00I 109.5 . . ?
C00S C00Q H00J 109.5 . . ?
O005 C00R H00L 109.5 . . ?
O005 C00R H00N 109.5 . . ?
O005 C00R H00O 109.5 . . ?
H00L C00R H00N 109.5 . . ?
H00L C00R H00O 109.5 . . ?
H00N C00R H00O 109.5 . . ?
N006 C00S C00Q 109.58(10) . . ?
N006 C00S H00Q 109.8 . . ?
N006 C00S H00R 109.8 . . ?
C00Q C00S H00Q 109.8 . . ?
C00Q C00S H00R 109.8 . . ?
H00Q C00S H00R 108.2 . . ?
N006 C00T H00S 109.7 . . ?
N006 C00T H00T 109.7 . . ?
N006 C00T C00V 109.68(10) . . ?
H00S C00T H00T 108.2 . . ?
C00V C00T H00S 109.7 . . ?
C00V C00T H00T 109.7 . . ?
N007 C00U H00U 115.4 . . ?
N009 C00U N007 129.24(11) . . ?
N009 C00U H00U 115.4 . . ?
O004 C00V C00T 111.56(10) . . ?
O004 C00V H00V 109.3 . . ?
O004 C00V H00W 109.3 . . ?
C00T C00V H00V 109.3 . . ?
C00T C00V H00W 109.3 . . ?
H00V C00V H00W 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl01 C00J C00L F002 -2.05(16) . . . . ?
Cl01 C00J C00L C00P 178.39(9) . . . . ?
F002 C00L C00P C00K -178.28(11) . . . . ?
O003 C00E C00H C00A -179.13(10) . . . . ?
O003 C00G C00O C00N -81.38(11) . . . . ?
O004 C00Q C00S N006 60.71(13) . . . . ?
O005 C00B C00E O003 -1.75(15) . . . . ?
O005 C00B C00E C00H 178.00(10) . . . . ?
O005 C00B C00M C00C -178.69(11) . . . . ?
N006 C00N C00O C00G -72.37(12) . . . . ?
N006 C00T C00V O004 -58.01(14) . . . . ?
N008 C00I C00K C00P 178.80(11) . . . . ?
N009 C00C C00M C00B 179.41(10) . . . . ?
C00A C00C C00M C00B 0.22(17) . . . . ?
C00B C00E C00H C00A 1.15(17) . . . . ?
C00C N009 C00U N007 0.0(2) . . . . ?
C00C C00A C00D N007 -0.30(16) . . . . ?
C00C C00A C00D N008 179.75(10) . . . . ?
C00C C00A C00H C00E 0.22(17) . . . . ?
C00D N007 C00U N009 0.3(2) . . . . ?
C00D N008 C00I C00F -166.92(11) . . . . ?
C00D N008 C00I C00K 14.87(19) . . . . ?
C00D C00A C00C N009 0.61(16) . . . . ?
C00D C00A C00C C00M 179.77(10) . . . . ?
C00D C00A C00H C00E 179.47(11) . . . . ?
C00E O003 C00G C00O 174.79(9) . . . . ?
C00E C00B C00M C00C 1.14(17) . . . . ?
C00F C00I C00K C00P 0.65(17) . . . . ?
C00F C00J C00L F002 179.43(11) . . . . ?
C00F C00J C00L C00P -0.12(19) . . . . ?
C00G O003 C00E C00B -177.21(9) . . . . ?
C00G O003 C00E C00H 3.05(16) . . . . ?
C00H C00A C00C N009 179.93(10) . . . . ?
C00H C00A C00C C00M -0.91(17) . . . . ?
C00H C00A C00D N007 -179.58(11) . . . . ?
C00H C00A C00D N008 0.47(17) . . . . ?
C00I N008 C00D N007 3.04(19) . . . . ?
C00I N008 C00D C00A -177.01(11) . . . . ?
C00I C00F C00J Cl01 -179.27(9) . . . . ?
C00I C00F C00J C00L -0.75(18) . . . . ?
C00I C00K C00P C00L -1.53(18) . . . . ?
C00J C00F C00I N008 -177.83(10) . . . . ?
C00J C00F C00I C00K 0.49(17) . . . . ?
C00J C00L C00P C00K 1.27(19) . . . . ?
C00M C00B C00E O003 178.40(10) . . . . ?
C00M C00B C00E C00H -1.85(17) . . . . ?
C00N N006 C00S C00Q 175.69(10) . . . . ?
C00N N006 C00T C00V -178.16(10) . . . . ?
C00Q O004 C00V C00T 57.80(13) . . . . ?
C00R O005 C00B C00E 179.39(10) . . . . ?
C00R O005 C00B C00M -0.77(17) . . . . ?
C00S N006 C00N C00O -82.44(12) . . . . ?
C00S N006 C00T C00V 58.07(13) . . . . ?
C00T N006 C00N C00O 155.23(10) . . . . ?
C00T N006 C00S C00Q -59.61(13) . . . . ?
C00U N007 C00D N008 179.85(11) . . . . ?
C00U N007 C00D C00A -0.10(17) . . . . ?
C00U N009 C00C C00A -0.49(17) . . . . ?
C00U N009 C00C C00M -179.66(11) . . . . ?
C00V O004 C00Q C00S -58.86(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.155
_oxdiff_exptl_absorpt_empirical_full_min 0.536
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Crizotinib-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1945591'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Crizotinib
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 Cl2 F N5 O'
_chemical_formula_sum            'C21 H22 Cl2 F N5 O'
_chemical_formula_weight         450.33
_chemical_absolute_configuration ad
_chemical_melting_point          478k
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'
O O 0.0492 0.0322 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   15.2412(4)
_cell_length_b                   10.1051(3)
_cell_length_c                   14.0138(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.491(3)
_cell_angle_gamma                90
_cell_volume                     2122.24(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5985
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6810
_cell_measurement_theta_min      3.1950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15504
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.036
_diffrn_reflns_theta_min         3.207
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  86.00   0.50    0.55    --   46.12-108.00 -50.00  168
  2  ω     34.00 111.00   0.50    6.50    --  107.00-108.00 -50.00  154
  3  ω     34.00 109.00   0.50    6.50    --  107.00 -94.00-180.00  150
  4  ω     34.00 117.00   0.50    6.50    --  107.00-125.00-180.00  166
  5  ω     34.00 109.00   0.50    6.50    --  107.00 -94.00 -30.00  150
  6  ω     34.00 117.00   0.50    6.50    --  107.00-125.00 150.00  166
  7  ω     85.00 178.00   0.50    6.50    --  107.00 108.00  46.00  186
  8  ω     76.00 168.00   0.50    6.50    --  107.00 125.00  90.00  184
  9  ω     93.00 178.00   0.50    6.50    --  107.00  45.00-180.00  170
 10  ω    -85.00   2.00   0.50    0.55    --  -46.12 108.00  46.00  174
 11  ω   -110.00 -27.00   0.50    6.50    -- -100.00 108.00  46.00  166
 12  ω   -115.00 -25.00   0.50    6.50    -- -100.00  30.00  90.00  180
 13  ω   -114.00 -27.00   0.50    6.50    -- -100.00  45.00 -90.00  174
 14  ω   -118.00 -71.00   0.50    0.55    --  -46.12-125.00  60.00   94
 15  ω   -118.00 -71.00   0.50    0.55    --  -46.12-125.00 -30.00   94
 16  ω   -118.00 -71.00   0.50    0.55    --  -46.12-125.00   0.00   94
 17  ω   -118.00 -71.00   0.50    0.55    --  -46.12-125.00  90.00   94
 18  ω   -173.00 -80.00   0.50    6.50    -- -100.00-108.00 -50.00  186
 19  ω   -118.00 -71.00   0.50    0.55    --  -46.12-125.00-150.00   94
 20  ω   -172.00 -85.00   0.50    6.50    -- -100.00 -45.00 150.00  174
 21  ω     46.00 116.00   0.50    0.50    --   46.62  77.00  90.00  140
 22  ω     33.00  62.00   0.50    0.50    --   46.62 -57.00 -30.00   58
 23  ω     26.00  52.00   0.50    0.50    --   46.62-125.00-180.00   52
 24  ω    -24.00   5.00   0.50    0.50    --   46.62 -57.00 -30.00   58
 25  ω   -107.00 -79.00   0.50    0.05    -- -100.00  15.00  30.00   56
 26  ω    -56.00 -30.00   0.50    0.05    -- -100.00  15.00  30.00   52
 27  ω     90.00 117.00   0.50    0.05    --  107.00  15.00 120.00   54
 28  ω     45.00  71.00   0.50    0.05    --  107.00 -45.00  30.00   52
 29  ω     88.00 114.00   0.50    0.05    --  107.00 -77.00 150.00   52
 30  ω    139.00 165.00   0.50    0.05    --  107.00  77.00 -60.00   52
 31  ω     36.00  80.00   0.50    0.05    --  107.00 -77.00 150.00   88
 32  ω     85.00 114.00   0.50    0.05    --  107.00  77.00 -60.00   58
 33  ω     48.00  74.00   0.50    0.05    --  107.00 -94.00-120.00   52
 34  ω     85.00 111.00   0.50    0.05    --  107.00 -45.00  30.00   52
 35  ω     60.00  86.00   0.50    0.05    --  107.00 -94.00   0.00   52
 36  ω    129.00 178.00   0.50    0.05    --  107.00  15.00 120.00   98
 37  ω     57.00 110.00   0.50    0.05    --  107.00 -45.00 -60.00  106
 38  ω     90.00 116.00   0.50    0.05    --  107.00-125.00  90.00   52
 39  ω    142.00 175.00   0.50    0.05    --  107.00  30.00 -60.00   66
 40  ω     20.00  45.00   0.50    0.50    --   46.62-108.00 -51.00   50
 41  ω     20.00  45.00   0.50    0.50    --   46.62-108.00 -51.00   50
 42  ω     20.00  45.00   0.50    0.50    --   46.62-108.00 -51.00   50
 43  ω    -66.00 -41.00   0.50    0.50    --  -46.62 108.00  46.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0242325000
_diffrn_orient_matrix_UB_12      -0.1479053000
_diffrn_orient_matrix_UB_13      0.0094450000
_diffrn_orient_matrix_UB_21      0.0341983000
_diffrn_orient_matrix_UB_22      0.0062600000
_diffrn_orient_matrix_UB_23      -0.0968361000
_diffrn_orient_matrix_UB_31      0.0938659000
_diffrn_orient_matrix_UB_32      0.0362446000
_diffrn_orient_matrix_UB_33      0.0551322000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                3816
_reflns_number_total             4263
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.668
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 1501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.061
_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)+(0.1050P)²+2.4487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N008(H008)
2.b Rotating group:
 N006(H00A,H00B)
2.c Ternary CH refined with riding coordinates:
 C00D(H00D), C00I(H00I)
2.d Secondary CH2 refined with riding coordinates:
 C00M(H00E,H00F), C00O(H00H,H00J), C00Q(H00P,H00Q), C00S(H00R,H00S)
2.e Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00G(H00G), C00K(H00K), C00N(H00N), C00T(H00T), C00U(H00U)
2.f Idealised Me refined as rotating group:
 C00P(H00L,H00M,H00O)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl01 Cl 0.53800(11) 0.69216(18) 0.63982(10) 0.0592(4) Uani 1 1 d . . . . .
Cl02 Cl 0.62450(13) 0.36793(15) 0.95627(11) 0.0647(5) Uani 1 1 d . . . . .
O003 O 0.7189(2) 0.6055(4) 0.9057(2) 0.0397(8) Uani 1 1 d . . . . .
F004 F 0.4421(3) 0.4574(5) 0.5616(3) 0.0725(12) Uani 1 1 d . . . . .
N005 N 0.9332(3) 0.4875(4) 0.8717(3) 0.0389(9) Uani 1 1 d . . . . .
N006 N 0.8759(3) 0.5232(5) 1.0113(3) 0.0416(9) Uani 1 1 d . . . . .
H00A H 0.929050 0.548805 1.037804 0.050 Uiso 1 1 d GR . . . .
H00B H 0.837500 0.575495 1.030424 0.050 Uiso 1 1 d GR . . . .
N007 N 0.7938(3) 0.5384(5) 0.4477(3) 0.0440(10) Uani 1 1 d . . . . .
N008 N 0.7311(3) 0.5777(5) 0.1437(3) 0.0482(11) Uani 1 1 d . . . . .
H008 H 0.713163 0.586341 0.082136 0.058 Uiso 1 1 d R . . . .
C009 C 0.8654(3) 0.5266(5) 0.9125(3) 0.0368(10) Uani 1 1 d . . . . .
C00A C 0.7835(3) 0.5682(5) 0.8545(4) 0.0359(10) Uani 1 1 d . . . . .
C00B C 0.7749(3) 0.5680(5) 0.7551(4) 0.0366(10) Uani 1 1 d . . . . .
H00C H 0.721970 0.596029 0.716563 0.044 Uiso 1 1 calc R . . . .
N00C N 0.8806(3) 0.5075(7) 0.4585(3) 0.0569(14) Uani 1 1 d . . . . .
C00D C 0.7414(3) 0.5568(6) 0.3497(4) 0.0447(12) Uani 1 1 d . . . . .
H00D H 0.678694 0.566484 0.355772 0.054 Uiso 1 1 calc R . . . .
C00E C 0.8464(3) 0.5253(5) 0.7117(3) 0.0369(10) Uani 1 1 d . . . . .
C00F C 0.5825(3) 0.5255(6) 0.7958(4) 0.0430(11) Uani 1 1 d . . . . .
C00G C 0.9232(3) 0.4858(5) 0.7743(4) 0.0390(10) Uani 1 1 d . . . . .
H00G H 0.970866 0.456046 0.747134 0.047 Uiso 1 1 calc R . . . .
C00H C 0.8404(3) 0.5241(6) 0.6060(4) 0.0401(10) Uani 1 1 d . . . . .
C00I C 0.6324(3) 0.6419(5) 0.8508(4) 0.0392(10) Uani 1 1 d . . . . .
H00I H 0.640670 0.710711 0.803898 0.047 Uiso 1 1 calc R . . . .
C00J C 0.5371(3) 0.5426(6) 0.7007(4) 0.0470(12) Uani 1 1 d . . . . .
C00K C 0.7674(3) 0.5493(6) 0.5343(4) 0.0433(12) Uani 1 1 d . . . . .
H00K H 0.710205 0.570183 0.543917 0.052 Uiso 1 1 calc R . . . .
C00L C 0.5753(4) 0.4010(6) 0.8365(4) 0.0512(14) Uani 1 1 d . . . . .
C00M C 0.7689(4) 0.6815(7) 0.3033(4) 0.0554(14) Uani 1 1 d . . . . .
H00E H 0.832343 0.678659 0.302040 0.066 Uiso 1 1 calc R . . . .
H00F H 0.757431 0.758027 0.340921 0.066 Uiso 1 1 calc R . . . .
C00N C 0.9074(4) 0.4989(8) 0.5532(4) 0.0552(15) Uani 1 1 d . . . . .
H00N H 0.965651 0.477930 0.581950 0.066 Uiso 1 1 calc R . . . .
C00O C 0.7161(4) 0.6934(7) 0.1994(4) 0.0558(14) Uani 1 1 d . . . . .
H00H H 0.652987 0.701640 0.200993 0.067 Uiso 1 1 calc R . . . .
H00J H 0.734818 0.772098 0.168919 0.067 Uiso 1 1 calc R . . . .
C00P C 0.5798(4) 0.6995(7) 0.9224(4) 0.0489(12) Uani 1 1 d . . . . .
H00L H 0.562756 0.629883 0.961884 0.073 Uiso 1 1 calc GR . . . .
H00M H 0.527344 0.742443 0.887847 0.073 Uiso 1 1 calc GR . . . .
H00O H 0.615995 0.762776 0.962947 0.073 Uiso 1 1 calc GR . . . .
C00Q C 0.7485(6) 0.4381(7) 0.2873(4) 0.0609(16) Uani 1 1 d . . . . .
H00P H 0.724195 0.361485 0.315112 0.073 Uiso 1 1 calc R . . . .
H00Q H 0.810903 0.420551 0.286189 0.073 Uiso 1 1 calc R . . . .
C00R C 0.4878(4) 0.4380(8) 0.6508(4) 0.0547(15) Uani 1 1 d . . . . .
C00S C 0.6984(6) 0.4589(7) 0.1836(5) 0.0640(17) Uani 1 1 d . . . . .
H00R H 0.707365 0.383186 0.143902 0.077 Uiso 1 1 calc R . . . .
H00S H 0.635035 0.467466 0.183463 0.077 Uiso 1 1 calc R . . . .
C00T C 0.5277(5) 0.2981(7) 0.7864(6) 0.0638(17) Uani 1 1 d . . . . .
H00T H 0.525312 0.216262 0.816089 0.077 Uiso 1 1 calc R . . . .
C00U C 0.4841(4) 0.3171(8) 0.6929(5) 0.0636(17) Uani 1 1 d . . . . .
H00U H 0.452437 0.248169 0.658542 0.076 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00J 1.737(7) . ?
Cl02 C00L 1.742(6) . ?
O003 C00A 1.372(6) . ?
O003 C00I 1.448(6) . ?
F004 C00R 1.329(7) . ?
N005 C009 1.328(6) . ?
N005 C00G 1.346(6) . ?
N006 H00A 0.8666 . ?
N006 H00B 0.8667 . ?
N006 C009 1.366(6) . ?
N007 N00C 1.340(6) . ?
N007 C00D 1.468(6) . ?
N007 C00K 1.352(7) . ?
N008 H008 0.8602 . ?
N008 C00O 1.448(9) . ?
N008 C00S 1.449(9) . ?
C009 C00A 1.423(7) . ?
C00A C00B 1.376(7) . ?
C00B H00C 0.9300 . ?
C00B C00E 1.408(7) . ?
N00C C00N 1.318(7) . ?
C00D H00D 0.9800 . ?
C00D C00M 1.513(9) . ?
C00D C00Q 1.500(9) . ?
C00E C00G 1.387(7) . ?
C00E C00H 1.468(7) . ?
C00F C00I 1.530(8) . ?
C00F C00J 1.396(7) . ?
C00F C00L 1.394(9) . ?
C00G H00G 0.9300 . ?
C00H C00K 1.380(7) . ?
C00H C00N 1.389(7) . ?
C00I H00I 0.9800 . ?
C00I C00P 1.510(7) . ?
C00J C00R 1.408(9) . ?
C00K H00K 0.9300 . ?
C00L C00T 1.384(9) . ?
C00M H00E 0.9700 . ?
C00M H00F 0.9700 . ?
C00M C00O 1.534(8) . ?
C00N H00N 0.9300 . ?
C00O H00H 0.9700 . ?
C00O H00J 0.9700 . ?
C00P H00L 0.9600 . ?
C00P H00M 0.9600 . ?
C00P H00O 0.9600 . ?
C00Q H00P 0.9700 . ?
C00Q H00Q 0.9700 . ?
C00Q C00S 1.529(8) . ?
C00R C00U 1.363(11) . ?
C00S H00R 0.9700 . ?
C00S H00S 0.9700 . ?
C00T H00T 0.9300 . ?
C00T C00U 1.370(11) . ?
C00U H00U 0.9300 . ?

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
C00A O003 C00I 117.6(4) . . ?
C009 N005 C00G 119.1(4) . . ?
H00A N006 H00B 108.5 . . ?
C009 N006 H00A 110.7 . . ?
C009 N006 H00B 109.7 . . ?
N00C N007 C00D 119.5(4) . . ?
N00C N007 C00K 111.5(4) . . ?
C00K N007 C00D 129.0(4) . . ?
C00O N008 H008 113.9 . . ?
C00O N008 C00S 111.2(5) . . ?
C00S N008 H008 113.7 . . ?
N005 C009 N006 118.2(4) . . ?
N005 C009 C00A 120.8(4) . . ?
N006 C009 C00A 121.0(4) . . ?
O003 C00A C009 114.9(4) . . ?
O003 C00A C00B 125.8(4) . . ?
C00B C00A C009 119.3(4) . . ?
C00A C00B H00C 120.0 . . ?
C00A C00B C00E 119.9(4) . . ?
C00E C00B H00C 120.0 . . ?
C00N N00C N007 104.4(4) . . ?
N007 C00D H00D 107.8 . . ?
N007 C00D C00M 111.2(5) . . ?
N007 C00D C00Q 111.0(5) . . ?
C00M C00D H00D 107.8 . . ?
C00Q C00D H00D 107.8 . . ?
C00Q C00D C00M 111.1(5) . . ?
C00B C00E C00H 121.8(4) . . ?
C00G C00E C00B 116.4(4) . . ?
C00G C00E C00H 121.7(4) . . ?
C00J C00F C00I 120.0(5) . . ?
C00L C00F C00I 123.9(5) . . ?
C00L C00F C00J 116.1(5) . . ?
N005 C00G C00E 124.4(5) . . ?
N005 C00G H00G 117.8 . . ?
C00E C00G H00G 117.8 . . ?
C00K C00H C00E 128.8(5) . . ?
C00K C00H C00N 102.7(4) . . ?
C00N C00H C00E 128.5(5) . . ?
O003 C00I C00F 113.1(4) . . ?
O003 C00I H00I 108.7 . . ?
O003 C00I C00P 106.6(4) . . ?
C00F C00I H00I 108.7 . . ?
C00P C00I C00F 110.8(4) . . ?
C00P C00I H00I 108.7 . . ?
C00F C00J Cl01 122.0(5) . . ?
C00F C00J C00R 120.6(6) . . ?
C00R C00J Cl01 117.4(4) . . ?
N007 C00K C00H 107.8(4) . . ?
N007 C00K H00K 126.1 . . ?
C00H C00K H00K 126.1 . . ?
C00F C00L Cl02 121.0(4) . . ?
C00T C00L Cl02 116.0(5) . . ?
C00T C00L C00F 122.9(6) . . ?
C00D C00M H00E 109.8 . . ?
C00D C00M H00F 109.8 . . ?
C00D C00M C00O 109.6(5) . . ?
H00E C00M H00F 108.2 . . ?
C00O C00M H00E 109.8 . . ?
C00O C00M H00F 109.8 . . ?
N00C C00N C00H 113.6(5) . . ?
N00C C00N H00N 123.2 . . ?
C00H C00N H00N 123.2 . . ?
N008 C00O C00M 110.0(5) . . ?
N008 C00O H00H 109.7 . . ?
N008 C00O H00J 109.7 . . ?
C00M C00O H00H 109.7 . . ?
C00M C00O H00J 109.7 . . ?
H00H C00O H00J 108.2 . . ?
C00I C00P H00L 109.5 . . ?
C00I C00P H00M 109.5 . . ?
C00I C00P H00O 109.5 . . ?
H00L C00P H00M 109.5 . . ?
H00L C00P H00O 109.5 . . ?
H00M C00P H00O 109.5 . . ?
C00D C00Q H00P 109.3 . . ?
C00D C00Q H00Q 109.3 . . ?
C00D C00Q C00S 111.6(5) . . ?
H00P C00Q H00Q 108.0 . . ?
C00S C00Q H00P 109.3 . . ?
C00S C00Q H00Q 109.3 . . ?
F004 C00R C00J 119.9(6) . . ?
F004 C00R C00U 118.9(6) . . ?
C00U C00R C00J 121.2(6) . . ?
N008 C00S C00Q 109.5(6) . . ?
N008 C00S H00R 109.8 . . ?
N008 C00S H00S 109.8 . . ?
C00Q C00S H00R 109.8 . . ?
C00Q C00S H00S 109.8 . . ?
H00R C00S H00S 108.2 . . ?
C00L C00T H00T 120.0 . . ?
C00U C00T C00L 119.9(7) . . ?
C00U C00T H00T 120.0 . . ?
C00R C00U C00T 119.2(6) . . ?
C00R C00U H00U 120.4 . . ?
C00T C00U H00U 120.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.889
_oxdiff_exptl_absorpt_empirical_full_min 0.294
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Nitrendipine-100k-HWRong
_database_code_depnum_ccdc_archive 'CCDC 1987339'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Nitrendipine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N2 O6'
_chemical_formula_sum            'C18 H20 N2 O6'
_chemical_formula_weight         360.36
_chemical_melting_point          434K
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'
O O 0.0492 0.0322 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.82590(10)
_cell_length_b                   15.2013(2)
_cell_length_c                   12.94740(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.7770(10)
_cell_angle_gamma                90
_cell_volume                     1733.32(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16420
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.8790
_cell_measurement_theta_min      4.4520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Strip
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34313
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.897
_diffrn_reflns_theta_min         4.492
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  29.00   0.50    0.52    --  -46.37  19.00 -60.00  182
  2  ω     69.00 118.00   0.50    0.52    --   46.37 135.00  46.00   98
  3  ω     69.00 178.00   0.50    2.10    --  107.00 135.00  46.00  218
  4  ω    128.00 178.00   0.50    2.10    --  107.00  15.00-120.00  100
  5  ω    103.00 129.00   0.50    2.10    --  107.00 125.00-180.00   52
  6  ω    147.00 177.00   0.50    2.10    --  107.00 125.00-180.00   60
  7  ω     90.00 123.00   0.50    2.10    --  107.00  15.00-120.00   66
  8  ω     63.00 122.00   0.50    2.10    --  107.00 -45.00 -60.00  118
  9  ω     86.00 113.00   0.50    2.10    --  107.00-125.00 -60.00   54
 10  ω     57.00  82.00   0.50    2.10    --  107.00-125.00 -60.00   50
 11  ω     34.00 124.00   0.50    2.10    --  107.00-135.00 -19.00  180
 12  ω     65.00 125.00   0.50    2.10    --  107.00 -61.00 120.00  120
 13  ω     90.00 178.00   0.50    2.10    --  107.00  15.00  60.00  176
 14  ω     70.00 178.00   0.50    2.10    --  107.00 134.00-132.00  216
 15  ω     70.00 118.00   0.50    0.52    --   46.37 134.00-132.00   96
 16  ω     32.00 124.00   0.50    2.10    --  107.00 -15.00-180.00  184
 17  ω     35.00 115.00   0.50    2.10    --  107.00 -61.00-120.00  160
 18  ω     36.00 107.00   0.50    2.10    --  107.00 -94.00   0.00  142
 19  ω     37.00 130.00   0.50    2.10    --  107.00 -77.00 120.00  186
 20  ω     35.00 108.00   0.50    2.10    --  107.00 -94.00 -30.00  146
 21  ω     34.00 117.00   0.50    2.10    --  107.00-125.00-150.00  166
 22  ω     21.00 101.00   0.50    0.52    --   46.37-135.00 -19.00  160
 23  ω     35.00  90.00   0.50    2.10    --  107.00 -45.00  60.00  110
 24  ω     35.00 122.00   0.50    2.10    --  107.00 -30.00  90.00  174
 25  ω     34.00 124.00   0.50    2.10    --  107.00-134.00 160.00  180
 26  ω     20.00 100.00   0.50    0.52    --   46.37-134.00 160.00  160
 27  ω    -25.00  63.00   0.50    0.52    --   46.37 -57.00-150.00  176
 28  ω    -62.00  29.00   0.50    0.52    --  -46.37  19.00 120.00  182
 29  ω   -100.00 -16.00   0.50    0.52    --  -46.37 134.00-132.00  168
 30  ω   -100.00 -16.00   0.50    0.52    --  -46.37 135.00  46.00  168
 31  ω   -102.00 -26.00   0.50    2.10    -- -100.00  30.00  90.00  152
 32  ω   -115.00 -25.00   0.50    2.10    -- -100.00  30.00 -90.00  180
 33  ω   -114.00 -28.00   0.50    2.10    -- -100.00  61.00  90.00  172
 34  ω   -124.00 -27.00   0.50    2.10    -- -100.00 135.00  46.00  194
 35  ω   -124.00 -27.00   0.50    2.10    -- -100.00 134.00-132.00  194
 36  ω   -173.00 -82.00   0.50    2.10    -- -100.00 -61.00-120.00  182
 37  ω   -118.00 -65.00   0.50    0.52    --  -46.37-135.00 -19.00  106
 38  ω   -118.00 -71.00   0.50    0.52    --  -46.37-125.00  30.00   94
 39  ω   -118.00 -66.00   0.50    0.52    --  -46.37-134.00 160.00  104
 40  ω   -118.00 -71.00   0.50    0.52    --  -46.37-125.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0343610000
_diffrn_orient_matrix_UB_12      -0.0984087000
_diffrn_orient_matrix_UB_13      0.0179248000
_diffrn_orient_matrix_UB_21      -0.1389318000
_diffrn_orient_matrix_UB_22      -0.0243183000
_diffrn_orient_matrix_UB_23      -0.0727558000
_diffrn_orient_matrix_UB_31      0.1006713000
_diffrn_orient_matrix_UB_32      -0.0000826000
_diffrn_orient_matrix_UB_33      -0.0926919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3257
_reflns_number_total             3602
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.054
_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)+(0.1027P)²+2.2389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00L,H00M)
2.c Aromatic/amide H refined with riding coordinates:
 N006(H006), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J)
2.d Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C), C00N(H00D,H00H,H00K), C00P(H00N,H00O,H00P), C00Q(H00Q,
 H00R,H00S)
;
_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
O001 O 0.7292(2) 0.64237(12) 0.43200(13) 0.0406(5) Uani 1 1 d . . . . .
O002 O 0.8879(2) 0.62537(12) 0.30609(16) 0.0409(5) Uani 1 1 d . . . . .
O003 O 0.3519(3) 0.87039(14) 0.67119(15) 0.0480(5) Uani 1 1 d . . . . .
O004 O 0.5208(3) 0.95567(14) 0.74795(15) 0.0543(6) Uani 1 1 d . . . . .
O005 O 0.2607(2) 0.79038(18) 0.36511(18) 0.0575(7) Uani 1 1 d . . . . .
N006 N 0.6512(3) 0.82800(14) 0.14189(16) 0.0353(5) Uani 1 1 d . . . . .
H006 H 0.689557 0.857487 0.093291 0.042 Uiso 1 1 calc R U . . .
N007 N 0.4725(3) 0.91102(15) 0.67376(16) 0.0409(6) Uani 1 1 d . . . . .
O008 O 0.1926(3) 0.86673(17) 0.2223(3) 0.0714(8) Uani 1 1 d . . . . .
C009 C 0.7713(3) 0.66432(15) 0.34775(18) 0.0298(5) Uani 1 1 d . . . . .
C00A C 0.6965(3) 0.73479(15) 0.28582(17) 0.0279(5) Uani 1 1 d . . . . .
C00B C 0.7415(3) 0.76633(15) 0.19472(18) 0.0302(5) Uani 1 1 d . . . . .
C00C C 0.5630(3) 0.90659(16) 0.58307(18) 0.0340(6) Uani 1 1 d . . . . .
C00D C 0.6035(3) 0.84044(15) 0.41911(18) 0.0303(5) Uani 1 1 d . . . . .
C00E C 0.5587(3) 0.77353(16) 0.33405(18) 0.0307(5) Uani 1 1 d . . . . .
H00E H 0.504395 0.725278 0.365622 0.037 Uiso 1 1 calc R U . . .
C00F C 0.5243(3) 0.84375(16) 0.50794(19) 0.0317(5) Uani 1 1 d . . . . .
H00F H 0.445882 0.804255 0.517205 0.038 Uiso 1 1 calc R U . . .
C00G C 0.6812(3) 0.96580(16) 0.5738(2) 0.0377(6) Uani 1 1 d . . . . .
H00G H 0.707625 1.005978 0.626115 0.045 Uiso 1 1 calc R U . . .
C00H C 0.4507(3) 0.81600(17) 0.2521(2) 0.0357(6) Uani 1 1 d . . . . .
C00I C 0.7578(3) 0.96307(17) 0.4850(2) 0.0364(6) Uani 1 1 d . . . . .
H00I H 0.836114 1.002748 0.476223 0.044 Uiso 1 1 calc R U . . .
C00J C 0.7197(3) 0.90160(16) 0.40767(19) 0.0317(5) Uani 1 1 d . . . . .
H00J H 0.772211 0.901245 0.347711 0.038 Uiso 1 1 calc R U . . .
C00K C 0.8797(3) 0.74288(18) 0.13922(19) 0.0356(6) Uani 1 1 d . . . . .
H00A H 0.856869 0.694142 0.093671 0.053 Uiso 1 1 calc R U . . .
H00B H 0.960743 0.726953 0.188803 0.053 Uiso 1 1 calc R U . . .
H00C H 0.910060 0.792511 0.099651 0.053 Uiso 1 1 calc R U . . .
C00L C 0.5024(3) 0.84476(17) 0.1631(2) 0.0372(6) Uani 1 1 d . . . . .
C00M C 0.2909(3) 0.8273(2) 0.2751(3) 0.0493(8) Uani 1 1 d . . . . .
C00N C 0.4134(4) 0.8937(2) 0.0777(2) 0.0510(8) Uani 1 1 d . . . . .
H00D H 0.384322 0.950328 0.102673 0.076 Uiso 1 1 calc R U . . .
H00H H 0.324035 0.860743 0.056194 0.076 Uiso 1 1 calc R U . . .
H00K H 0.475106 0.901203 0.020028 0.076 Uiso 1 1 calc R U . . .
C00O C 0.9634(4) 0.5574(2) 0.3703(3) 0.0555(9) Uani 1 1 d . . . . .
H00L H 0.993227 0.580863 0.438349 0.067 Uiso 1 1 calc R U . . .
H00M H 0.895127 0.508294 0.378613 0.067 Uiso 1 1 calc R U . . .
C00P C 0.1101(4) 0.8045(3) 0.4022(4) 0.0825(15) Uani 1 1 d . . . . .
H00N H 0.037199 0.769462 0.362221 0.124 Uiso 1 1 calc R U . . .
H00O H 0.083425 0.865545 0.395049 0.124 Uiso 1 1 calc R U . . .
H00P H 0.110450 0.787850 0.473731 0.124 Uiso 1 1 calc R U . . .
C00Q C 1.0936(6) 0.5291(4) 0.3207(5) 0.114(2) Uani 1 1 d . . . . .
H00Q H 1.063540 0.508996 0.252085 0.171 Uiso 1 1 calc R U . . .
H00R H 1.141745 0.481829 0.359584 0.171 Uiso 1 1 calc R U . . .
H00S H 1.163388 0.577192 0.316877 0.171 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.222(3) . ?
O002 C009 1.331(3) . ?
O002 C00O 1.460(3) . ?
O003 N007 1.230(3) . ?
O004 N007 1.229(3) . ?
O005 C00M 1.336(4) . ?
O005 C00P 1.459(4) . ?
N006 H006 0.8600 . ?
N006 C00B 1.382(3) . ?
N006 C00L 1.383(4) . ?
N007 C00C 1.464(4) . ?
O008 C00M 1.225(4) . ?
C009 C00A 1.469(3) . ?
C00A C00B 1.357(3) . ?
C00A C00E 1.522(3) . ?
C00B C00K 1.499(4) . ?
C00C C00F 1.390(3) . ?
C00C C00G 1.389(4) . ?
C00D C00E 1.532(3) . ?
C00D C00F 1.386(4) . ?
C00D C00J 1.399(4) . ?
C00E H00E 0.9800 . ?
C00E C00H 1.522(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00I 1.373(4) . ?
C00H C00L 1.341(4) . ?
C00H C00M 1.470(4) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.394(3) . ?
C00J H00J 0.9300 . ?
C00K H00A 0.9600 . ?
C00K H00B 0.9600 . ?
C00K H00C 0.9600 . ?
C00L C00N 1.509(4) . ?
C00N H00D 0.9600 . ?
C00N H00H 0.9600 . ?
C00N H00K 0.9600 . ?
C00O H00L 0.9700 . ?
C00O H00M 0.9700 . ?
C00O C00Q 1.419(6) . ?
C00P H00N 0.9600 . ?
C00P H00O 0.9600 . ?
C00P H00P 0.9600 . ?
C00Q H00Q 0.9600 . ?
C00Q H00R 0.9600 . ?
C00Q H00S 0.9600 . ?

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
C009 O002 C00O 114.8(2) . . ?
C00M O005 C00P 117.6(3) . . ?
C00B N006 H006 118.3 . . ?
C00B N006 C00L 123.4(2) . . ?
C00L N006 H006 118.3 . . ?
O003 N007 C00C 118.2(2) . . ?
O004 N007 O003 123.6(3) . . ?
O004 N007 C00C 118.2(3) . . ?
O001 C009 O002 121.9(2) . . ?
O001 C009 C00A 122.3(2) . . ?
O002 C009 C00A 115.8(2) . . ?
C009 C00A C00E 113.7(2) . . ?
C00B C00A C009 125.8(2) . . ?
C00B C00A C00E 120.5(2) . . ?
N006 C00B C00K 112.6(2) . . ?
C00A C00B N006 118.5(2) . . ?
C00A C00B C00K 128.8(2) . . ?
C00F C00C N007 118.1(3) . . ?
C00G C00C N007 119.4(2) . . ?
C00G C00C C00F 122.4(2) . . ?
C00F C00D C00E 120.0(2) . . ?
C00F C00D C00J 118.5(2) . . ?
C00J C00D C00E 121.4(2) . . ?
C00A C00E C00D 112.10(19) . . ?
C00A C00E H00E 107.9 . . ?
C00A C00E C00H 111.0(2) . . ?
C00D C00E H00E 107.9 . . ?
C00H C00E C00D 109.86(19) . . ?
C00H C00E H00E 107.9 . . ?
C00C C00F H00F 120.3 . . ?
C00D C00F C00C 119.5(2) . . ?
C00D C00F H00F 120.3 . . ?
C00C C00G H00G 121.1 . . ?
C00I C00G C00C 117.8(2) . . ?
C00I C00G H00G 121.1 . . ?
C00L C00H C00E 120.3(2) . . ?
C00L C00H C00M 121.4(3) . . ?
C00M C00H C00E 118.3(3) . . ?
C00G C00I H00I 119.6 . . ?
C00G C00I C00J 120.9(3) . . ?
C00J C00I H00I 119.6 . . ?
C00D C00J H00J 119.6 . . ?
C00I C00J C00D 120.9(2) . . ?
C00I C00J H00J 119.6 . . ?
C00B C00K H00A 109.5 . . ?
C00B C00K H00B 109.5 . . ?
C00B C00K H00C 109.5 . . ?
H00A C00K H00B 109.5 . . ?
H00A C00K H00C 109.5 . . ?
H00B C00K H00C 109.5 . . ?
N006 C00L C00N 113.6(3) . . ?
C00H C00L N006 119.5(2) . . ?
C00H C00L C00N 126.9(3) . . ?
O005 C00M C00H 112.1(3) . . ?
O008 C00M O005 121.2(3) . . ?
O008 C00M C00H 126.7(4) . . ?
C00L C00N H00D 109.5 . . ?
C00L C00N H00H 109.5 . . ?
C00L C00N H00K 109.5 . . ?
H00D C00N H00H 109.5 . . ?
H00D C00N H00K 109.5 . . ?
H00H C00N H00K 109.5 . . ?
O002 C00O H00L 110.1 . . ?
O002 C00O H00M 110.1 . . ?
H00L C00O H00M 108.4 . . ?
C00Q C00O O002 108.0(3) . . ?
C00Q C00O H00L 110.1 . . ?
C00Q C00O H00M 110.1 . . ?
O005 C00P H00N 109.5 . . ?
O005 C00P H00O 109.5 . . ?
O005 C00P H00P 109.5 . . ?
H00N C00P H00O 109.5 . . ?
H00N C00P H00P 109.5 . . ?
H00O C00P H00P 109.5 . . ?
C00O C00Q H00Q 109.5 . . ?
C00O C00Q H00R 109.5 . . ?
C00O C00Q H00S 109.5 . . ?
H00Q C00Q H00R 109.5 . . ?
H00Q C00Q H00S 109.5 . . ?
H00R C00Q H00S 109.5 . . ?

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
O001 C009 C00A C00B 176.0(2) . . . . ?
O001 C009 C00A C00E -2.9(3) . . . . ?
O002 C009 C00A C00B -4.3(3) . . . . ?
O002 C009 C00A C00E 176.71(19) . . . . ?
O003 N007 C00C C00F -12.5(3) . . . . ?
O003 N007 C00C C00G 166.1(2) . . . . ?
O004 N007 C00C C00F 168.0(2) . . . . ?
O004 N007 C00C C00G -13.4(3) . . . . ?
N007 C00C C00F C00D 177.2(2) . . . . ?
N007 C00C C00G C00I -176.2(2) . . . . ?
C009 O002 C00O C00Q -173.9(4) . . . . ?
C009 C00A C00B N006 174.8(2) . . . . ?
C009 C00A C00B C00K -4.5(4) . . . . ?
C009 C00A C00E C00D 80.2(2) . . . . ?
C009 C00A C00E C00H -156.5(2) . . . . ?
C00A C00E C00H C00L -24.4(3) . . . . ?
C00A C00E C00H C00M 157.8(2) . . . . ?
C00B N006 C00L C00H 15.5(4) . . . . ?
C00B N006 C00L C00N -163.1(2) . . . . ?
C00B C00A C00E C00D -98.9(3) . . . . ?
C00B C00A C00E C00H 24.4(3) . . . . ?
C00C C00G C00I C00J -1.2(4) . . . . ?
C00D C00E C00H C00L 100.2(3) . . . . ?
C00D C00E C00H C00M -77.6(3) . . . . ?
C00E C00A C00B N006 -6.3(3) . . . . ?
C00E C00A C00B C00K 174.4(2) . . . . ?
C00E C00D C00F C00C -178.0(2) . . . . ?
C00E C00D C00J C00I 179.0(2) . . . . ?
C00E C00H C00L N006 6.2(4) . . . . ?
C00E C00H C00L C00N -175.4(2) . . . . ?
C00E C00H C00M O005 -5.3(3) . . . . ?
C00E C00H C00M O008 173.1(3) . . . . ?
C00F C00C C00G C00I 2.3(4) . . . . ?
C00F C00D C00E C00A -141.4(2) . . . . ?
C00F C00D C00E C00H 94.7(3) . . . . ?
C00F C00D C00J C00I 1.7(3) . . . . ?
C00G C00C C00F C00D -1.4(4) . . . . ?
C00G C00I C00J C00D -0.7(4) . . . . ?
C00J C00D C00E C00A 41.3(3) . . . . ?
C00J C00D C00E C00H -82.6(3) . . . . ?
C00J C00D C00F C00C -0.6(3) . . . . ?
C00L N006 C00B C00A -15.4(3) . . . . ?
C00L N006 C00B C00K 164.0(2) . . . . ?
C00L C00H C00M O005 176.9(2) . . . . ?
C00L C00H C00M O008 -4.6(4) . . . . ?
C00M C00H C00L N006 -176.0(2) . . . . ?
C00M C00H C00L C00N 2.3(4) . . . . ?
C00O O002 C009 O001 -2.1(3) . . . . ?
C00O O002 C009 C00A 178.2(2) . . . . ?
C00P O005 C00M O008 -4.7(4) . . . . ?
C00P O005 C00M C00H 173.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.086
_oxdiff_exptl_absorpt_empirical_full_min 0.438
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Axitinib-100k-HWRong
_database_code_depnum_ccdc_archive 'CCDC 1987321'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Axitinib
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H18 N4 O S)'
_chemical_formula_sum            'C44 H36 N8 O2 S2'
_chemical_formula_weight         772.93
_chemical_melting_point          495K
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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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                   11.8120(2)
_cell_length_b                   12.3827(2)
_cell_length_c                   14.7603(2)
_cell_angle_alpha                80.868(2)
_cell_angle_beta                 81.207(2)
_cell_angle_gamma                65.701(2)
_cell_volume                     1933.49(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21795
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      73.2960
_cell_measurement_theta_min      3.0510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            68140
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.149
_diffrn_reflns_theta_min         3.047
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 121.00   0.50    0.78    --   48.00  79.00 -61.83  196
  2  ω     83.00 178.00   0.50    3.10    --  105.44 113.00  70.00  190
  3  ω     36.00 132.00   0.50    0.78    --   60.00  77.00   9.46  192
  4  ω     39.00 137.00   0.50    0.78    --   64.00  79.00-149.93  196
  5  ω     39.00 137.00   0.50    0.78    --   64.00  79.00-118.74  196
  6  ω     35.00  85.00   0.50    3.10    --  105.44 -45.00  30.00  100
  7  ω     47.00  85.00   0.50    3.10    --  105.44 -94.00   0.00   76
  8  ω     33.00 112.00   0.50    3.10    --  105.44-113.00 -21.00  158
  9  ω     45.00  86.00   0.50    3.10    --  105.44 -94.00-180.00   82
 10  ω     33.00 113.00   0.50    3.10    --  105.44-125.00 -60.00  160
 11  ω     34.00  92.00   0.50    3.10    --  105.44 -94.00 -30.00  116
 12  ω     37.00 105.00   0.50    3.10    --  105.44 -94.00  30.00  136
 13  ω     34.00 106.00   0.50    3.10    --  105.44 -94.00 120.00  144
 14  ω      6.00  89.00   0.50    0.78    --   46.37-113.00 -21.00  166
 15  ω     15.00  95.00   0.50    0.78    --   46.37-125.00-120.00  160
 16  ω     23.00 118.00   0.50    0.78    --   46.37  77.00-150.00  190
 17  ω     27.00 125.00   0.50    0.78    --   52.00  81.00 -63.62  196
 18  ω     30.00 129.00   0.50    0.78    --   56.00  83.00 111.51  198
 19  ω     23.00 121.00   0.50    0.78    --   48.00  79.00 171.87  196
 20  ω     19.00  45.00   0.50    0.78    --   48.00  88.00  32.61   52
 21  ω     17.00  43.00   0.50    0.78    --   48.00  92.00 -21.66   52
 22  ω      3.00  31.00   0.50    0.78    --   36.00  96.00 -24.01   56
 23  ω      9.00  36.00   0.50    0.78    --   40.00  93.00  58.80   54
 24  ω     19.00  45.00   0.50    0.78    --   48.00  88.00 104.93   52
 25  ω    -15.00  20.00   0.50    0.78    --   20.00 101.00   2.15   70
 26  ω    -42.00 -16.00   0.50    0.78    --   12.00 134.00  -4.94   52
 27  ω     14.00  45.00   0.50    0.78    --   44.00  90.00-118.39   62
 28  ω    -62.00  27.00   0.50    0.78    --  -46.37  57.00  30.00  178
 29  ω    -73.00  17.00   0.50    0.78    --    0.00 -59.00-103.83  180
 30  ω    -72.00 -46.00   0.50    0.78    --  -68.00 -73.00 -17.74   52
 31  ω    -73.00 -48.00   0.50    0.78    --  -72.00 -76.00 -34.78   50
 32  ω    -80.00 -46.00   0.50    0.78    --  -68.00 -73.00  34.91   68
 33  ω    -74.00 -49.00   0.50    0.78    --  -72.00 -74.00  67.22   50
 34  ω    -79.00 -53.00   0.50    0.78    --  -72.00 -69.00  86.76   52
 35  ω    -88.00 -62.00   0.50    3.10    --  -84.00 -73.00  30.40   52
 36  ω    -87.00 -54.00   0.50    3.10    --  -80.00 -83.00 -29.04   66
 37  ω    -82.00 -57.00   0.50    3.10    --  -84.00 -83.00 -51.94   50
 38  ω    -88.00 -62.00   0.50    3.10    --  -84.00 -75.00  -4.43   52
 39  ω    -86.00 -60.00   0.50    3.10    --  -84.00 -76.00  16.38   52
 40  ω    -85.00 -59.00   0.50    3.10    --  -84.00 -83.00  63.30   52
 41  ω    -86.00 -61.00   0.50    3.10    --  -84.00 -75.00 127.72   50
 42  ω    -90.00 -65.00   0.50    3.10    --  -88.00 -74.00 152.13   50
 43  ω   -102.00 -69.00   0.50    3.10    --  -88.00 -72.00 105.33   66
 44  ω    -97.00 -65.00   0.50    3.10    --  -92.00 -83.00  43.64   64
 45  ω    -90.00 -64.00   0.50    3.10    --  -88.00 -80.00 -67.42   52
 46  ω    -76.00 -50.00   0.50    0.78    --  -72.00 -77.00-117.06   52
 47  ω    -72.00 -46.00   0.50    0.78    --  -72.00 -82.00-150.68   52
 48  ω    -81.00 -54.00   0.50    3.10    --  -80.00 -82.00-160.71   54
 49  ω    -83.00 -57.00   0.50    3.10    --  -84.00 -83.00-176.72   52
 50  ω   -100.00 -66.00   0.50    3.10    --  -88.00 -74.00-132.24   68
 51  ω    -97.00 -67.00   0.50    3.10    --  -88.00 -74.00-159.12   60
 52  ω    -98.00 -68.00   0.50    3.10    --  -88.00 -67.00-120.16   60
 53  ω    -98.00 -65.00   0.50    3.10    --  -88.00 -75.00-149.10   66
 54  ω   -120.00 -51.00   0.50    0.78    --  -72.00 -71.00-112.61  138
 55  ω   -106.00 -80.00   0.50    3.10    -- -100.00 -68.00 -49.90   52
 56  ω   -132.00 -35.00   0.50    0.78    --  -60.00 -79.00 -54.00  194
 57  ω   -110.00 -84.00   0.50    3.10    --  -92.00 -57.00  71.73   52
 58  ω   -113.00 -69.00   0.50    3.10    --  -92.00 -75.00  63.72   88
 59  ω   -116.00 -73.00   0.50    3.10    --  -96.00 -75.00 125.27   86
 60  ω   -130.00 -75.00   0.50    3.10    --  -96.00 -69.00 165.17  110
 61  ω   -132.00 -35.00   0.50    0.78    --  -60.00 -80.00 158.79  194
 62  ω   -137.00 -38.00   0.50    0.78    --  -64.00 -81.00 131.16  198
 63  ω   -131.00 -78.00   0.50    3.10    -- -100.00 -72.00  64.54  106
 64  ω   -131.00 -77.00   0.50    3.10    -- -100.00 -76.00  14.91  108
 65  ω   -140.00 -43.00   0.50    0.78    --  -68.00 -79.00 -84.52  194
 66  ω   -140.00 -44.00   0.50    0.78    --  -68.00 -77.00 -72.61  192
 67  ω   -140.00 -46.00   0.50    0.78    --  -68.00 -72.00   7.06  188
 68  ω   -141.00 -63.00   0.50    3.10    --  -88.00 -80.00  91.84  156
 69  ω   -146.00-113.00   0.50    3.10    -- -100.00 -68.00 -49.90   66
 70  ω   -154.00 -76.00   0.50    3.10    -- -100.00 -77.00  30.00  156
 71  ω   -155.00-129.00   0.50    3.10    --  -88.00 -74.00 152.13   52
 72  ω   -157.00-129.00   0.50    3.10    --  -96.00 -75.00 125.27   56
 73  ω   -161.00-102.00   0.50    3.10    --  -92.00 -83.00  43.64  118
 74  ω   -163.00-137.00   0.50    3.10    --  -92.00 -57.00  71.73   52
 75  ω   -165.00-139.00   0.50    3.10    --  -92.00 -75.00  63.72   52
 76  ω   -173.00 -79.00   0.50    3.10    -- -100.00-113.00 -21.00  188
 77  ω   -142.00-113.00   0.50    3.10    --  -88.00 -75.00-149.10   58
 78  ω   -156.00-111.00   0.50    3.10    --  -84.00 -83.00-176.72   90
 79  ω   -156.00-121.00   0.50    3.10    --  -88.00 -74.00-159.12   70
 80  ω   -167.00 -72.00   0.50    3.10    --  -96.00 -77.00 -82.65  190
 81  ω   -167.00 -72.00   0.50    3.10    --  -96.00 -78.00  -4.74  190
 82  ω   -164.00 -73.00   0.50    3.10    --  -96.00 -76.00 -54.47  182
 83  ω   -168.00 -80.00   0.50    3.10    -- -100.00 -68.00 -97.59  176
 84  ω   -173.00 -78.00   0.50    3.10    -- -100.00 -74.00-162.21  190
 85  ω   -169.00 -79.00   0.50    3.10    -- -100.00 -75.00-114.38  180
 86  ω   -173.00-138.00   0.50    3.10    -- -100.00 -76.00  14.91   70
 87  ω   -172.00 -76.00   0.50    3.10    -- -100.00 -76.00 152.02  192
 88  ω    -89.00  -2.00   0.50    0.78    --  -46.37 113.00  70.00  174
 89  ω   -111.00 -27.00   0.50    3.10    -- -100.00 113.00  70.00  168
 90  ω   -117.00 -27.00   0.50    3.10    -- -100.00 125.00-180.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0500989000
_diffrn_orient_matrix_UB_12      0.0492016000
_diffrn_orient_matrix_UB_13      -0.0949971000
_diffrn_orient_matrix_UB_21      0.1064177000
_diffrn_orient_matrix_UB_22      -0.1062011000
_diffrn_orient_matrix_UB_23      -0.0430237000
_diffrn_orient_matrix_UB_31      -0.0826959000
_diffrn_orient_matrix_UB_32      -0.0717440000
_diffrn_orient_matrix_UB_33      0.0201562000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7063
_reflns_number_total             7707
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.108
_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)+(0.0822P)²+0.9839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1460
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N005(H005), N007(H007), N00A(H00A), N00B(H00B), C00G(H00G), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00Q(H00Q), C00S(H00S), C00V(H00V),
 C00X(H00X), C00Z(H00Z), C010(H010), C012(H012), C013(H013), C014(H014),
 C016(H016), C017(H017), C018(H018), C01A(H01D), C01B(H01E), C01C(H01F),
 C01D(H01G), C01E(H01H), C01F(H01I), C01H(H01J), C01I(H01K), C01J(H01L)
2.b Idealised Me refined as rotating group:
 C01G(H01A,H01B,H01C), C01K(H01M,H01N,H01O)
;
_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
S001 S 0.14029(5) 1.09803(4) 0.55641(4) 0.02927(14) Uani 1 1 d . . . . .
S002 S 1.05467(5) 0.16573(5) -0.05740(4) 0.03144(15) Uani 1 1 d . . . . .
O003 O -0.01675(13) 1.30425(13) 0.63644(10) 0.0309(3) Uani 1 1 d . . . . .
O004 O 1.28184(15) 0.04141(14) -0.14405(11) 0.0383(4) Uani 1 1 d . . . . .
N005 N 0.24047(15) 0.71267(15) 0.40585(12) 0.0278(4) Uani 1 1 d . . . . .
H005 H 0.166443 0.720421 0.398891 0.033 Uiso 1 1 calc R U . . .
N006 N 0.34565(16) 0.61655(15) 0.38413(12) 0.0285(4) Uani 1 1 d . . . . .
N007 N 0.08326(17) 1.41166(16) 0.66876(12) 0.0305(4) Uani 1 1 d . . . . .
H007 H 0.140172 1.439065 0.651601 0.037 Uiso 1 1 calc R U . . .
N008 N 0.82825(16) 0.39361(15) 0.36069(12) 0.0295(4) Uani 1 1 d . . . . .
N009 N 0.53628(17) 0.29308(17) 0.17264(13) 0.0334(4) Uani 1 1 d . . . . .
N00A N 0.64209(16) 0.20264(17) 0.14382(13) 0.0327(4) Uani 1 1 d . . . . .
H00A H 0.655491 0.128442 0.156793 0.039 Uiso 1 1 calc R U . . .
N00B N 1.43222(18) 0.11277(18) -0.17121(14) 0.0383(4) Uani 1 1 d . . . . .
H00B H 1.465250 0.155474 -0.153957 0.046 Uiso 1 1 calc R U . . .
N00C N 0.36782(17) 0.82447(17) 0.13250(15) 0.0388(5) Uani 1 1 d . . . . .
C00D C 0.39608(18) 0.74849(18) 0.44271(14) 0.0261(4) Uani 1 1 d . . . . .
C00E C 0.06445(18) 1.34531(17) 0.61471(14) 0.0269(4) Uani 1 1 d . . . . .
C00F C 0.14778(18) 1.32103(18) 0.52634(14) 0.0267(4) Uani 1 1 d . . . . .
C00G C 0.26564(18) 1.18905(18) 0.40984(15) 0.0282(4) Uani 1 1 d . . . . .
H00G H 0.293126 1.115712 0.386997 0.034 Uiso 1 1 calc R U . . .
C00H C 0.18822(18) 1.20922(18) 0.49277(14) 0.0267(4) Uani 1 1 d . . . . .
C00I C 0.26581(18) 0.79474(17) 0.43969(14) 0.0256(4) Uani 1 1 d . . . . .
C00J C 0.44042(18) 0.63700(18) 0.40578(14) 0.0270(4) Uani 1 1 d . . . . .
C00K C 0.18721(18) 0.90684(18) 0.46846(14) 0.0273(4) Uani 1 1 d . . . . .
H00K H 0.101959 0.939109 0.462751 0.033 Uiso 1 1 calc R U . . .
C00L C 0.57015(19) 0.55268(18) 0.39154(14) 0.0287(4) Uani 1 1 d . . . . .
H00L H 0.631590 0.572786 0.407591 0.034 Uiso 1 1 calc R U . . .
C00M C 0.18490(19) 1.40804(18) 0.47608(15) 0.0288(4) Uani 1 1 d . . . . .
H00M H 0.157406 1.482057 0.497811 0.035 Uiso 1 1 calc R U . . .
C00N C 0.30160(19) 1.27653(19) 0.36167(15) 0.0297(4) Uani 1 1 d . . . . .
H00N H 0.352955 1.261531 0.306719 0.036 Uiso 1 1 calc R U . . .
C00O C 0.24160(19) 0.96676(18) 0.50538(14) 0.0278(4) Uani 1 1 d . . . . .
C00P C 1.15893(19) 0.19471(18) 0.00052(15) 0.0300(4) Uani 1 1 d . . . . .
C00Q C 0.2620(2) 1.38667(19) 0.39425(15) 0.0308(4) Uani 1 1 d . . . . .
H00Q H 0.286823 1.445315 0.361735 0.037 Uiso 1 1 calc R U . . .
C00R C 0.73612(18) 0.36317(18) 0.34431(14) 0.0268(4) Uani 1 1 d . . . . .
C00S C 0.44954(19) 0.81126(18) 0.48035(14) 0.0289(4) Uani 1 1 d . . . . .
H00S H 0.535295 0.781022 0.483451 0.035 Uiso 1 1 calc R U . . .
C00T C 0.7242(2) 0.24343(19) 0.09206(15) 0.0303(4) Uani 1 1 d . . . . .
C00U C 1.2845(2) 0.16336(19) -0.03582(15) 0.0318(5) Uani 1 1 d . . . . .
C00V C 0.60649(19) 0.44915(18) 0.35721(14) 0.0288(4) Uani 1 1 d . . . . .
H00V H 0.545014 0.429918 0.340136 0.035 Uiso 1 1 calc R U . . .
C00W C 0.54971(19) 0.3935(2) 0.13917(15) 0.0311(5) Uani 1 1 d . . . . .
C00X C 1.1190(2) 0.24664(19) 0.08346(15) 0.0325(5) Uani 1 1 d . . . . .
H00X H 1.036509 0.267210 0.108181 0.039 Uiso 1 1 calc R U . . .
C00Y C 0.66926(19) 0.36873(19) 0.08695(15) 0.0300(4) Uani 1 1 d . . . . .
C00Z C 0.7615(2) 0.25240(19) 0.31701(14) 0.0300(4) Uani 1 1 d . . . . .
H00Z H 0.696683 0.233983 0.305210 0.036 Uiso 1 1 calc R U . . .
C010 C 0.84437(19) 0.17966(19) 0.05065(15) 0.0309(5) Uani 1 1 d . . . . .
H010 H 0.879321 0.096814 0.055716 0.037 Uiso 1 1 calc R U . . .
C011 C 0.9073(2) 0.24511(19) 0.00264(15) 0.0313(5) Uani 1 1 d . . . . .
C012 C 0.1277(2) 0.8481(2) 0.20204(15) 0.0330(5) Uani 1 1 d . . . . .
H012 H 0.047957 0.855569 0.227117 0.040 Uiso 1 1 calc R U . . .
C013 C 0.8839(2) 0.16941(19) 0.30743(15) 0.0313(5) Uani 1 1 d . . . . .
H013 H 0.902206 0.095262 0.288713 0.038 Uiso 1 1 calc R U . . .
C014 C 0.9456(2) 0.3116(2) 0.35179(15) 0.0325(5) Uani 1 1 d . . . . .
H014 H 1.009285 0.331688 0.363533 0.039 Uiso 1 1 calc R U . . .
C015 C 0.3416(2) 0.7273(2) 0.15478(15) 0.0316(5) Uani 1 1 d . . . . .
C016 C 0.4466(2) 0.5058(2) 0.15890(15) 0.0329(5) Uani 1 1 d . . . . .
H016 H 0.373635 0.501286 0.189662 0.039 Uiso 1 1 calc R U . . .
C017 C 0.37262(19) 0.91868(19) 0.51271(15) 0.0294(4) Uani 1 1 d . . . . .
H017 H 0.406452 0.960256 0.539600 0.035 Uiso 1 1 calc R U . . .
C018 C 0.9780(2) 0.19895(19) 0.32618(15) 0.0317(5) Uani 1 1 d . . . . .
H018 H 1.060736 0.144745 0.321757 0.038 Uiso 1 1 calc R U . . .
C019 C 1.3325(2) 0.10149(19) -0.12143(16) 0.0330(5) Uani 1 1 d . . . . .
C01A C 0.4470(2) 0.6136(2) 0.13723(16) 0.0346(5) Uani 1 1 d . . . . .
H01D H 0.520759 0.618087 0.108155 0.042 Uiso 1 1 calc R U . . .
C01B C 0.1538(2) 0.9471(2) 0.17557(16) 0.0349(5) Uani 1 1 d . . . . .
H01E H 0.091563 1.023103 0.179611 0.042 Uiso 1 1 calc R U . . .
C01C C 1.1999(2) 0.2677(2) 0.12898(16) 0.0368(5) Uani 1 1 d . . . . .
H01F H 1.171543 0.302411 0.183981 0.044 Uiso 1 1 calc R U . . .
C01D C 0.7358(2) 0.4335(2) 0.03650(15) 0.0331(5) Uani 1 1 d . . . . .
H01G H 0.701499 0.516360 0.031256 0.040 Uiso 1 1 calc R U . . .
C01E C 0.8533(2) 0.3718(2) -0.00520(15) 0.0333(5) Uani 1 1 d . . . . .
H01H H 0.898116 0.413864 -0.039101 0.040 Uiso 1 1 calc R U . . .
C01F C 0.2220(2) 0.7363(2) 0.19091(15) 0.0321(5) Uani 1 1 d . . . . .
H01I H 0.205657 0.668049 0.207376 0.039 Uiso 1 1 calc R U . . .
C01G C 0.0083(2) 1.4382(2) 0.75660(16) 0.0361(5) Uani 1 1 d . . . . .
H01A H -0.077791 1.482366 0.746066 0.054 Uiso 1 1 calc R U . . .
H01B H 0.035905 1.484592 0.787181 0.054 Uiso 1 1 calc R U . . .
H01C H 0.017433 1.365067 0.794500 0.054 Uiso 1 1 calc R U . . .
C01H C 1.3240(2) 0.2376(2) 0.09347(17) 0.0391(5) Uani 1 1 d . . . . .
H01J H 1.378553 0.252064 0.124288 0.047 Uiso 1 1 calc R U . . .
C01I C 1.3648(2) 0.1860(2) 0.01169(17) 0.0372(5) Uani 1 1 d . . . . .
H01K H 1.447533 0.165829 -0.012268 0.045 Uiso 1 1 calc R U . . .
C01J C 0.2751(2) 0.9312(2) 0.14264(18) 0.0395(5) Uani 1 1 d . . . . .
H01L H 0.293248 0.998471 0.126653 0.047 Uiso 1 1 calc R U . . .
C01K C 1.4854(3) 0.0531(2) -0.25456(18) 0.0472(6) Uani 1 1 d . . . . .
H01M H 1.420490 0.070945 -0.293497 0.071 Uiso 1 1 calc R U . . .
H01N H 1.523467 -0.031392 -0.238226 0.071 Uiso 1 1 calc R U . . .
H01O H 1.547152 0.080573 -0.286854 0.071 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C00H 1.780(2) . ?
S001 C00O 1.776(2) . ?
S002 C00P 1.777(2) . ?
S002 C011 1.782(2) . ?
O003 C00E 1.240(3) . ?
O004 C019 1.237(3) . ?
N005 H005 0.8600 . ?
N005 N006 1.358(2) . ?
N005 C00I 1.352(3) . ?
N006 C00J 1.337(3) . ?
N007 H007 0.8600 . ?
N007 C00E 1.332(3) . ?
N007 C01G 1.455(3) . ?
N008 C00R 1.353(3) . ?
N008 C014 1.341(3) . ?
N009 N00A 1.354(2) . ?
N009 C00W 1.326(3) . ?
N00A H00A 0.8600 . ?
N00A C00T 1.354(3) . ?
N00B H00B 0.8600 . ?
N00B C019 1.336(3) . ?
N00B C01K 1.457(3) . ?
N00C C015 1.343(3) . ?
N00C C01J 1.338(3) . ?
C00D C00I 1.409(3) . ?
C00D C00J 1.426(3) . ?
C00D C00S 1.400(3) . ?
C00E C00F 1.500(3) . ?
C00F C00H 1.411(3) . ?
C00F C00M 1.392(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.401(3) . ?
C00G C00N 1.379(3) . ?
C00I C00K 1.405(3) . ?
C00J C00L 1.462(3) . ?
C00K H00K 0.9300 . ?
C00K C00O 1.374(3) . ?
C00L H00L 0.9300 . ?
C00L C00V 1.331(3) . ?
C00M H00M 0.9300 . ?
C00M C00Q 1.388(3) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.387(3) . ?
C00O C017 1.426(3) . ?
C00P C00U 1.409(3) . ?
C00P C00X 1.399(3) . ?
C00Q H00Q 0.9300 . ?
C00R C00V 1.466(3) . ?
C00R C00Z 1.391(3) . ?
C00S H00S 0.9300 . ?
C00S C017 1.377(3) . ?
C00T C00Y 1.408(3) . ?
C00T C010 1.406(3) . ?
C00U C019 1.495(3) . ?
C00U C01I 1.398(3) . ?
C00V H00V 0.9300 . ?
C00W C00Y 1.438(3) . ?
C00W C016 1.459(3) . ?
C00X H00X 0.9300 . ?
C00X C01C 1.375(3) . ?
C00Y C01D 1.402(3) . ?
C00Z H00Z 0.9300 . ?
C00Z C013 1.389(3) . ?
C010 H010 0.9300 . ?
C010 C011 1.366(3) . ?
C011 C01E 1.422(3) . ?
C012 H012 0.9300 . ?
C012 C01B 1.368(3) . ?
C012 C01F 1.391(3) . ?
C013 H013 0.9300 . ?
C013 C018 1.380(3) . ?
C014 H014 0.9300 . ?
C014 C018 1.386(3) . ?
C015 C01A 1.474(3) . ?
C015 C01F 1.397(3) . ?
C016 H016 0.9300 . ?
C016 C01A 1.324(3) . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C01A H01D 0.9300 . ?
C01B H01E 0.9300 . ?
C01B C01J 1.384(3) . ?
C01C H01F 0.9300 . ?
C01C C01H 1.392(3) . ?
C01D H01G 0.9300 . ?
C01D C01E 1.380(3) . ?
C01E H01H 0.9300 . ?
C01F H01I 0.9300 . ?
C01G H01A 0.9600 . ?
C01G H01B 0.9600 . ?
C01G H01C 0.9600 . ?
C01H H01J 0.9300 . ?
C01H C01I 1.383(3) . ?
C01I H01K 0.9300 . ?
C01J H01L 0.9300 . ?
C01K H01M 0.9600 . ?
C01K H01N 0.9600 . ?
C01K H01O 0.9600 . ?

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
C00O S001 C00H 103.04(10) . . ?
C00P S002 C011 102.18(10) . . ?
N006 N005 H005 124.0 . . ?
C00I N005 H005 124.0 . . ?
C00I N005 N006 112.09(16) . . ?
C00J N006 N005 106.00(16) . . ?
C00E N007 H007 119.7 . . ?
C00E N007 C01G 120.55(19) . . ?
C01G N007 H007 119.7 . . ?
C014 N008 C00R 117.47(18) . . ?
C00W N009 N00A 106.78(18) . . ?
N009 N00A H00A 124.2 . . ?
C00T N00A N009 111.66(18) . . ?
C00T N00A H00A 124.2 . . ?
C019 N00B H00B 119.8 . . ?
C019 N00B C01K 120.4(2) . . ?
C01K N00B H00B 119.8 . . ?
C01J N00C C015 118.2(2) . . ?
C00I C00D C00J 104.11(18) . . ?
C00S C00D C00I 119.94(18) . . ?
C00S C00D C00J 135.89(18) . . ?
O003 C00E N007 121.98(19) . . ?
O003 C00E C00F 121.36(18) . . ?
N007 C00E C00F 116.65(18) . . ?
C00H C00F C00E 119.84(19) . . ?
C00M C00F C00E 120.85(18) . . ?
C00M C00F C00H 119.30(19) . . ?
C00H C00G H00G 119.6 . . ?
C00N C00G H00G 119.6 . . ?
C00N C00G C00H 120.86(19) . . ?
C00F C00H S001 119.47(16) . . ?
C00G C00H S001 121.85(16) . . ?
C00G C00H C00F 118.67(19) . . ?
N005 C00I C00D 106.93(17) . . ?
N005 C00I C00K 131.31(19) . . ?
C00K C00I C00D 121.75(19) . . ?
N006 C00J C00D 110.84(17) . . ?
N006 C00J C00L 122.15(18) . . ?
C00D C00J C00L 127.01(19) . . ?
C00I C00K H00K 121.4 . . ?
C00O C00K C00I 117.21(18) . . ?
C00O C00K H00K 121.4 . . ?
C00J C00L H00L 117.7 . . ?
C00V C00L C00J 124.6(2) . . ?
C00V C00L H00L 117.7 . . ?
C00F C00M H00M 119.3 . . ?
C00Q C00M C00F 121.41(19) . . ?
C00Q C00M H00M 119.3 . . ?
C00G C00N H00N 119.6 . . ?
C00G C00N C00Q 120.73(19) . . ?
C00Q C00N H00N 119.6 . . ?
C00K C00O S001 117.21(15) . . ?
C00K C00O C017 121.63(18) . . ?
C017 C00O S001 120.74(16) . . ?
C00U C00P S002 120.20(16) . . ?
C00X C00P S002 120.95(16) . . ?
C00X C00P C00U 118.8(2) . . ?
C00M C00Q H00Q 120.5 . . ?
C00N C00Q C00M 119.0(2) . . ?
C00N C00Q H00Q 120.5 . . ?
N008 C00R C00V 118.69(18) . . ?
N008 C00R C00Z 121.70(18) . . ?
C00Z C00R C00V 119.60(19) . . ?
C00D C00S H00S 120.7 . . ?
C017 C00S C00D 118.69(19) . . ?
C017 C00S H00S 120.7 . . ?
N00A C00T C00Y 107.30(18) . . ?
N00A C00T C010 129.7(2) . . ?
C010 C00T C00Y 123.0(2) . . ?
C00P C00U C019 120.5(2) . . ?
C01I C00U C00P 119.0(2) . . ?
C01I C00U C019 120.5(2) . . ?
C00L C00V C00R 124.9(2) . . ?
C00L C00V H00V 117.5 . . ?
C00R C00V H00V 117.5 . . ?
N009 C00W C00Y 110.66(19) . . ?
N009 C00W C016 118.0(2) . . ?
C00Y C00W C016 131.4(2) . . ?
C00P C00X H00X 119.5 . . ?
C01C C00X C00P 121.1(2) . . ?
C01C C00X H00X 119.5 . . ?
C00T C00Y C00W 103.6(2) . . ?
C01D C00Y C00T 118.76(19) . . ?
C01D C00Y C00W 137.6(2) . . ?
C00R C00Z H00Z 120.1 . . ?
C013 C00Z C00R 119.7(2) . . ?
C013 C00Z H00Z 120.1 . . ?
C00T C010 H010 121.6 . . ?
C011 C010 C00T 116.9(2) . . ?
C011 C010 H010 121.6 . . ?
C010 C011 S002 117.20(16) . . ?
C010 C011 C01E 121.4(2) . . ?
C01E C011 S002 121.25(18) . . ?
C01B C012 H012 120.5 . . ?
C01B C012 C01F 119.0(2) . . ?
C01F C012 H012 120.5 . . ?
C00Z C013 H013 120.6 . . ?
C018 C013 C00Z 118.8(2) . . ?
C018 C013 H013 120.6 . . ?
N008 C014 H014 117.9 . . ?
N008 C014 C018 124.1(2) . . ?
C018 C014 H014 117.9 . . ?
N00C C015 C01A 115.01(19) . . ?
N00C C015 C01F 121.2(2) . . ?
C01F C015 C01A 123.8(2) . . ?
C00W C016 H016 116.9 . . ?
C01A C016 C00W 126.3(2) . . ?
C01A C016 H016 116.9 . . ?
C00O C017 H017 119.7 . . ?
C00S C017 C00O 120.6(2) . . ?
C00S C017 H017 119.7 . . ?
C013 C018 C014 118.13(19) . . ?
C013 C018 H018 120.9 . . ?
C014 C018 H018 120.9 . . ?
O004 C019 N00B 121.9(2) . . ?
O004 C019 C00U 120.7(2) . . ?
N00B C019 C00U 117.5(2) . . ?
C015 C01A H01D 116.9 . . ?
C016 C01A C015 126.2(2) . . ?
C016 C01A H01D 116.9 . . ?
C012 C01B H01E 120.8 . . ?
C012 C01B C01J 118.3(2) . . ?
C01J C01B H01E 120.8 . . ?
C00X C01C H01F 119.7 . . ?
C00X C01C C01H 120.6(2) . . ?
C01H C01C H01F 119.7 . . ?
C00Y C01D H01G 120.7 . . ?
C01E C01D C00Y 118.6(2) . . ?
C01E C01D H01G 120.7 . . ?
C011 C01E H01H 119.3 . . ?
C01D C01E C011 121.3(2) . . ?
C01D C01E H01H 119.3 . . ?
C012 C01F C015 119.4(2) . . ?
C012 C01F H01I 120.3 . . ?
C015 C01F H01I 120.3 . . ?
N007 C01G H01A 109.5 . . ?
N007 C01G H01B 109.5 . . ?
N007 C01G H01C 109.5 . . ?
H01A C01G H01B 109.5 . . ?
H01A C01G H01C 109.5 . . ?
H01B C01G H01C 109.5 . . ?
C01C C01H H01J 120.5 . . ?
C01I C01H C01C 119.0(2) . . ?
C01I C01H H01J 120.5 . . ?
C00U C01I H01K 119.2 . . ?
C01H C01I C00U 121.5(2) . . ?
C01H C01I H01K 119.2 . . ?
N00C C01J C01B 123.7(2) . . ?
N00C C01J H01L 118.2 . . ?
C01B C01J H01L 118.2 . . ?
N00B C01K H01M 109.5 . . ?
N00B C01K H01N 109.5 . . ?
N00B C01K H01O 109.5 . . ?
H01M C01K H01N 109.5 . . ?
H01M C01K H01O 109.5 . . ?
H01N C01K H01O 109.5 . . ?

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
S001 C00O C017 C00S 174.14(17) . . . . ?
S002 C00P C00U C019 -2.2(3) . . . . ?
S002 C00P C00U C01I -179.30(17) . . . . ?
S002 C00P C00X C01C 179.16(18) . . . . ?
S002 C011 C01E C01D 175.84(17) . . . . ?
O003 C00E C00F C00H -35.7(3) . . . . ?
O003 C00E C00F C00M 143.5(2) . . . . ?
N005 N006 C00J C00D 0.2(2) . . . . ?
N005 N006 C00J C00L -179.63(18) . . . . ?
N005 C00I C00K C00O 176.1(2) . . . . ?
N006 N005 C00I C00D -1.5(2) . . . . ?
N006 N005 C00I C00K 178.4(2) . . . . ?
N006 C00J C00L C00V -0.6(3) . . . . ?
N007 C00E C00F C00H 143.48(19) . . . . ?
N007 C00E C00F C00M -37.3(3) . . . . ?
N008 C00R C00V C00L -5.9(3) . . . . ?
N008 C00R C00Z C013 1.0(3) . . . . ?
N008 C014 C018 C013 0.9(3) . . . . ?
N009 N00A C00T C00Y 0.4(2) . . . . ?
N009 N00A C00T C010 178.8(2) . . . . ?
N009 C00W C00Y C00T 0.8(2) . . . . ?
N009 C00W C00Y C01D 179.7(2) . . . . ?
N009 C00W C016 C01A 174.6(2) . . . . ?
N00A N009 C00W C00Y -0.6(2) . . . . ?
N00A N009 C00W C016 178.88(19) . . . . ?
N00A C00T C00Y C00W -0.7(2) . . . . ?
N00A C00T C00Y C01D -179.86(19) . . . . ?
N00A C00T C010 C011 -179.2(2) . . . . ?
N00C C015 C01A C016 175.3(2) . . . . ?
N00C C015 C01F C012 1.5(3) . . . . ?
C00D C00I C00K C00O -4.1(3) . . . . ?
C00D C00J C00L C00V 179.6(2) . . . . ?
C00D C00S C017 C00O -1.9(3) . . . . ?
C00E C00F C00H S001 -0.4(3) . . . . ?
C00E C00F C00H C00G 179.75(18) . . . . ?
C00E C00F C00M C00Q 179.97(19) . . . . ?
C00F C00M C00Q C00N 0.7(3) . . . . ?
C00G C00N C00Q C00M -0.3(3) . . . . ?
C00H S001 C00O C00K -121.96(17) . . . . ?
C00H S001 C00O C017 65.38(19) . . . . ?
C00H C00F C00M C00Q -0.8(3) . . . . ?
C00H C00G C00N C00Q 0.1(3) . . . . ?
C00I N005 N006 C00J 0.8(2) . . . . ?
C00I C00D C00J N006 -1.1(2) . . . . ?
C00I C00D C00J C00L 178.7(2) . . . . ?
C00I C00D C00S C017 -0.9(3) . . . . ?
C00I C00K C00O S001 -171.40(15) . . . . ?
C00I C00K C00O C017 1.2(3) . . . . ?
C00J C00D C00I N005 1.6(2) . . . . ?
C00J C00D C00I C00K -178.35(19) . . . . ?
C00J C00D C00S C017 -177.6(2) . . . . ?
C00J C00L C00V C00R -178.8(2) . . . . ?
C00K C00O C017 C00S 1.8(3) . . . . ?
C00M C00F C00H S001 -179.63(15) . . . . ?
C00M C00F C00H C00G 0.5(3) . . . . ?
C00N C00G C00H S001 179.99(16) . . . . ?
C00N C00G C00H C00F -0.1(3) . . . . ?
C00O S001 C00H C00F -166.11(16) . . . . ?
C00O S001 C00H C00G 13.75(19) . . . . ?
C00P S002 C011 C010 -115.88(18) . . . . ?
C00P S002 C011 C01E 69.0(2) . . . . ?
C00P C00U C019 O004 -24.9(3) . . . . ?
C00P C00U C019 N00B 155.8(2) . . . . ?
C00P C00U C01I C01H 0.4(4) . . . . ?
C00P C00X C01C C01H -0.1(4) . . . . ?
C00R N008 C014 C018 0.6(3) . . . . ?
C00R C00Z C013 C018 0.5(3) . . . . ?
C00S C00D C00I N005 -176.10(18) . . . . ?
C00S C00D C00I C00K 4.0(3) . . . . ?
C00S C00D C00J N006 176.0(2) . . . . ?
C00S C00D C00J C00L -4.2(4) . . . . ?
C00T C00Y C01D C01E -0.8(3) . . . . ?
C00T C010 C011 S002 -175.34(16) . . . . ?
C00T C010 C011 C01E -0.2(3) . . . . ?
C00U C00P C00X C01C 0.4(3) . . . . ?
C00V C00R C00Z C013 -178.05(19) . . . . ?
C00W N009 N00A C00T 0.1(2) . . . . ?
C00W C00Y C01D C01E -179.7(2) . . . . ?
C00W C016 C01A C015 178.1(2) . . . . ?
C00X C00P C00U C019 176.6(2) . . . . ?
C00X C00P C00U C01I -0.5(3) . . . . ?
C00X C01C C01H C01I -0.1(4) . . . . ?
C00Y C00T C010 C011 -1.0(3) . . . . ?
C00Y C00W C016 C01A -6.1(4) . . . . ?
C00Y C01D C01E C011 -0.4(3) . . . . ?
C00Z C00R C00V C00L 173.2(2) . . . . ?
C00Z C013 C018 C014 -1.4(3) . . . . ?
C010 C00T C00Y C00W -179.2(2) . . . . ?
C010 C00T C00Y C01D 1.6(3) . . . . ?
C010 C011 C01E C01D 0.9(3) . . . . ?
C011 S002 C00P C00U -169.64(18) . . . . ?
C011 S002 C00P C00X 11.6(2) . . . . ?
C012 C01B C01J N00C 2.1(4) . . . . ?
C014 N008 C00R C00V 177.50(19) . . . . ?
C014 N008 C00R C00Z -1.6(3) . . . . ?
C015 N00C C01J C01B 0.6(4) . . . . ?
C016 C00W C00Y C00T -178.6(2) . . . . ?
C016 C00W C00Y C01D 0.4(4) . . . . ?
C019 C00U C01I C01H -176.7(2) . . . . ?
C01A C015 C01F C012 -177.8(2) . . . . ?
C01B C012 C01F C015 1.3(3) . . . . ?
C01C C01H C01I C00U -0.1(4) . . . . ?
C01F C012 C01B C01J -3.0(3) . . . . ?
C01F C015 C01A C016 -5.4(4) . . . . ?
C01G N007 C00E O003 0.2(3) . . . . ?
C01G N007 C00E C00F -178.95(18) . . . . ?
C01I C00U C019 O004 152.1(2) . . . . ?
C01I C00U C019 N00B -27.2(3) . . . . ?
C01J N00C C015 C01A 177.0(2) . . . . ?
C01J N00C C015 C01F -2.4(3) . . . . ?
C01K N00B C019 O004 -0.4(4) . . . . ?
C01K N00B C019 C00U 178.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.729
_oxdiff_exptl_absorpt_empirical_full_min 0.564
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Clotrimazole-100k-HWRong
_database_code_depnum_ccdc_archive 'CCDC 1987332'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2020-01-06
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Clotrimazole
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Cl N2'
_chemical_formula_sum            'C22 H17 Cl N2'
_chemical_formula_weight         344.82
_chemical_melting_point          421K
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'
Cl Cl 0.3639 0.7018 '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                   8.68460(10)
_cell_length_b                   10.3809(2)
_cell_length_c                   10.5107(2)
_cell_angle_alpha                113.566(2)
_cell_angle_beta                 97.7510(10)
_cell_angle_gamma                96.7670(10)
_cell_volume                     845.09(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18475
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9070
_cell_measurement_theta_min      4.6390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            30455
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.050
_diffrn_reflns_theta_min         4.684
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  61.00   0.50    0.05    --   46.37 -45.00 -99.00  174
  2  ω     31.00 122.00   0.50    0.05    --   46.37  19.00-180.00  182
  3  ω     56.00 122.00   0.50    0.05    --  105.44 -61.00 -90.00  132
  4  ω     91.00 178.00   0.50    0.05    --  105.44  45.00  51.00  174
  5  ω     89.00 176.00   0.50    0.05    --  105.44  61.00-120.00  174
  6  ω     42.00 137.00   0.50    0.05    --   64.00  73.00 -35.52  190
  7  ω     32.00 119.00   0.50    0.05    --   46.37  45.00  51.00  174
  8  ω     36.00 132.00   0.50    0.05    --   60.00  78.00 135.16  192
  9  ω     38.00 132.00   0.50    0.05    --   60.00  72.00  62.85  188
 10  ω     38.00 132.00   0.50    0.05    --   60.00  72.00  30.22  188
 11  ω     39.00 137.00   0.50    0.05    --   64.00  79.00 -27.19  196
 12  ω     33.00 120.00   0.50    0.05    --  105.44 -45.00 -99.00  174
 13  ω     43.00  69.00   0.50    0.05    --  105.44 -94.00-180.00   52
 14  ω     33.00 109.00   0.50    0.05    --  105.44-125.00 -60.00  152
 15  ω     40.00 100.00   0.50    0.05    --  105.44 -94.00  90.00  120
 16  ω     91.00 117.00   0.50    0.05    --  105.44-125.00  90.00   52
 17  ω     49.00 108.00   0.50    0.05    --  105.44 -94.00 120.00  118
 18  ω     15.00  95.00   0.50    0.05    --   46.37-125.00 150.00  160
 19  ω    -40.00 -11.00   0.50    0.05    --  -40.00 -88.00-119.25   58
 20  ω    -70.00 -44.00   0.50    0.05    --  -68.00 -78.00-153.38   52
 21  ω    -72.00 -46.00   0.50    0.05    --  -68.00 -73.00-179.37   52
 22  ω    -80.00 -54.00   0.50    0.05    --  -80.00 -82.00-110.24   52
 23  ω    -81.00 -55.00   0.50    0.05    --  -76.00 -74.00 -70.22   52
 24  ω    -72.00 -46.00   0.50    0.05    --  -72.00 -82.00  -6.71   52
 25  ω    -72.00 -46.00   0.50    0.05    --  -72.00 -82.00  52.19   52
 26  ω    -79.00 -53.00   0.50    0.05    --  -72.00 -69.00  83.58   52
 27  ω    -71.00 -46.00   0.50    0.05    --  -68.00 -72.00 152.90   50
 28  ω    -76.00 -50.00   0.50    0.05    --  -76.00 -83.00 170.22   52
 29  ω    -92.00 -66.00   0.50    0.05    --  -84.00 -62.00 178.51   52
 30  ω    -90.00 -64.00   0.50    0.05    --  -84.00 -71.00 146.75   52
 31  ω   -101.00 -67.00   0.50    0.05    --  -88.00 -73.00 136.06   68
 32  ω   -110.00 -84.00   0.50    0.05    --  -72.00 -69.00  83.58   52
 33  ω    -89.00 -64.00   0.50    0.05    --  -80.00 -56.00  56.57   50
 34  ω    -87.00 -61.00   0.50    0.05    --  -80.00 -73.00  49.44   52
 35  ω    -89.00 -63.00   0.50    0.05    --  -84.00 -69.00  29.48   52
 36  ω    -94.00 -68.00   0.50    0.05    --  -84.00 -59.00 -34.15   52
 37  ω    -95.00 -69.00   0.50    0.05    --  -92.00 -75.00 -24.67   52
 38  ω   -102.00 -49.00   0.50    0.05    --  -68.00 -68.00  43.90  106
 39  ω   -101.00 -70.00   0.50    0.05    --  -88.00 -62.00  74.62   62
 40  ω   -110.00 -69.00   0.50    0.05    --  -84.00 -55.00 147.89   82
 41  ω   -112.00 -69.00   0.50    0.05    --  -92.00 -74.00 108.20   86
 42  ω   -103.00 -75.00   0.50    0.05    --  -92.00 -64.00  22.60   56
 43  ω   -109.00 -70.00   0.50    0.05    --  -88.00 -63.00   6.32   78
 44  ω   -102.00 -68.00   0.50    0.05    --  -92.00 -80.00 -81.02   68
 45  ω   -102.00 -54.00   0.50    0.05    --  -72.00 -63.00-121.25   96
 46  ω    -88.00 -62.00   0.50    0.05    --  -80.00 -63.00-160.28   52
 47  ω    -93.00 -67.00   0.50    0.05    --  -84.00 -62.00-163.33   52
 48  ω   -100.00 -72.00   0.50    0.05    --  -96.00 -77.00 -94.02   56
 49  ω   -116.00 -73.00   0.50    0.05    --  -96.00 -76.00 -57.39   86
 50  ω   -112.00 -77.00   0.50    0.05    -- -100.00 -74.00-105.72   70
 51  ω   -115.00 -76.00   0.50    0.05    -- -100.00 -77.00 -30.00   78
 52  ω   -119.00 -32.00   0.50    0.05    --  -46.37 -45.00 -99.00  174
 53  ω     22.00 121.00   0.50    0.05    --   48.00  82.00  18.71  198
 54  ω     27.00 125.00   0.50    0.05    --   52.00  81.00 -65.16  196
 55  ω     30.00 125.00   0.50    0.05    --   52.00  74.00-100.25  190
 56  ω     34.00 129.00   0.50    0.05    --   56.00  73.00  84.13  190
 57  ω     34.00 129.00   0.50    0.05    --   56.00  73.00 -66.98  190
 58  ω     36.00 132.00   0.50    0.05    --   60.00  77.00 -55.80  192
 59  ω     28.00 125.00   0.50    0.05    --   52.00  78.00-155.43  194
 60  ω    -12.00  36.00   0.50    0.05    --   20.00  94.00 115.25   96
 61  ω     11.00  45.00   0.50    0.05    --   40.00  88.00 161.30   68
 62  ω     28.00 125.00   0.50    0.05    --   52.00  78.00 114.41  194
 63  ω    -57.00 -30.00   0.50    0.05    --   16.00 163.00 -87.26   54
 64  ω    -61.00  26.00   0.50    0.05    --  -46.37  45.00  51.00  174
 65  ω    -95.00 -70.00   0.50    0.05    -- -100.00  45.00  51.00   50
 66  ω   -122.00 -31.00   0.50    0.05    --  -46.37 -19.00 120.00  182
 67  ω   -120.00 -32.00   0.50    0.05    --  -46.37 -38.00 -30.00  176
 68  ω   -113.00 -35.00   0.50    0.05    -- -100.00  30.00-120.00  156
 69  ω   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00 -30.00  190
 70  ω   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00  30.00  190
 71  ω   -129.00-103.00   0.50    0.05    --  -68.00 -72.00 152.90   52
 72  ω   -132.00 -35.00   0.50    0.05    --  -60.00 -80.00 118.86  194
 73  ω   -123.00 -76.00   0.50    0.05    -- -100.00 -78.00  23.23   94
 74  ω   -121.00 -79.00   0.50    0.05    -- -100.00 -70.00 -10.91   84
 75  ω   -130.00-104.00   0.50    0.05    --  -72.00 -63.00-121.25   52
 76  ω   -132.00 -78.00   0.50    0.05    --  -96.00 -61.00-163.26  108
 77  ω   -113.00 -80.00   0.50    0.05    -- -100.00 -71.00-178.01   66
 78  ω   -150.00-122.00   0.50    0.05    --  -96.00 -76.00 -57.39   56
 79  ω   -160.00-115.00   0.50    0.05    --  -88.00 -63.00   6.32   90
 80  ω   -154.00-128.00   0.50    0.05    --  -88.00 -62.00  74.62   52
 81  ω   -157.00-107.00   0.50    0.05    --  -88.00 -73.00 136.06  100
 82  ω   -155.00-120.00   0.50    0.05    --  -92.00 -74.00 108.20   70
 83  ω   -168.00 -77.00   0.50    0.05    -- -100.00 -76.00  77.69  182
 84  ω   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00 -99.00  174
 85  ω   -164.00-111.00   0.50    0.05    --  -92.00 -75.00 -24.67  106
 86  ω   -166.00-123.00   0.50    0.05    -- -100.00 -74.00-105.72   86
 87  ω   -163.00-136.00   0.50    0.05    --  -96.00 -61.00-163.26   54
 88  ω   -157.00 -82.00   0.50    0.05    -- -100.00 -61.00-180.00  150
 89  ω   -111.00 -62.00   0.50    0.05    -- -100.00  61.00-120.00   98
 90  ω   -116.00 -34.00   0.50    0.05    -- -100.00 125.00-180.00  164
 91  ω   -113.00 -27.00   0.50    0.05    -- -100.00 125.00   0.00  172
 92  ω   -171.00 -77.00   0.50    0.05    -- -100.00 -77.00 150.00  188
 93  ω   -165.00-139.00   0.50    0.05    -- -100.00 -70.00 -10.91   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0573559000
_diffrn_orient_matrix_UB_12      -0.1390594000
_diffrn_orient_matrix_UB_13      -0.0830793000
_diffrn_orient_matrix_UB_21      0.1700120000
_diffrn_orient_matrix_UB_22      0.0850595000
_diffrn_orient_matrix_UB_23      0.0372617000
_diffrn_orient_matrix_UB_31      0.0323303000
_diffrn_orient_matrix_UB_32      -0.0247636000
_diffrn_orient_matrix_UB_33      0.1354408000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3152
_reflns_number_total             3349
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.112
_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)+(0.0288P)²+0.9166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1037
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P)
;
_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
Cl01 Cl 0.02456(5) 0.55449(5) 0.18681(5) 0.02575(14) Uani 1 1 d . . . . .
N002 N 0.32502(18) 0.76255(17) 0.25892(17) 0.0221(3) Uani 1 1 d . . . . .
N003 N 0.2724(2) 0.82373(19) 0.07916(18) 0.0295(4) Uani 1 1 d . . . . .
C004 C 0.3341(2) 0.5187(2) 0.2326(2) 0.0230(4) Uani 1 1 d . . . . .
C005 C 0.2273(2) 0.6084(2) 0.4956(2) 0.0239(4) Uani 1 1 d . . . . .
H005 H 0.196449 0.516315 0.423555 0.029 Uiso 1 1 calc R U . . .
C006 C 0.5682(2) 0.7234(2) 0.3797(2) 0.0224(4) Uani 1 1 d . . . . .
C007 C 0.2702(2) 0.8894(2) 0.3102(2) 0.0249(4) Uani 1 1 d . . . . .
H007 H 0.257058 0.940267 0.402298 0.030 Uiso 1 1 calc R U . . .
C008 C 0.3190(2) 0.7124(2) 0.4727(2) 0.0218(4) Uani 1 1 d . . . . .
C009 C 0.8985(2) 0.8040(2) 0.4648(2) 0.0290(4) Uani 1 1 d . . . . .
H009 H 1.007881 0.831831 0.493807 0.035 Uiso 1 1 calc R U . . .
C00A C 0.8110(2) 0.7478(2) 0.5377(2) 0.0275(4) Uani 1 1 d . . . . .
H00A H 0.862118 0.736901 0.615398 0.033 Uiso 1 1 calc R U . . .
C00B C 0.3660(2) 0.8490(2) 0.5846(2) 0.0242(4) Uani 1 1 d . . . . .
H00B H 0.429720 0.920277 0.572870 0.029 Uiso 1 1 calc R U . . .
C00C C 0.2394(2) 0.9253(2) 0.2004(2) 0.0277(4) Uani 1 1 d . . . . .
H00C H 0.201194 1.006953 0.205644 0.033 Uiso 1 1 calc R U . . .
C00D C 0.1803(2) 0.6388(2) 0.6243(2) 0.0280(4) Uani 1 1 d . . . . .
H00D H 0.118220 0.567232 0.636977 0.034 Uiso 1 1 calc R U . . .
C00E C 0.1313(2) 0.3114(2) 0.0727(2) 0.0277(4) Uani 1 1 d . . . . .
H00E H 0.026031 0.273058 0.027858 0.033 Uiso 1 1 calc R U . . .
C00F C 0.6579(2) 0.7782(2) 0.3064(2) 0.0265(4) Uani 1 1 d . . . . .
H00F H 0.607569 0.788371 0.228000 0.032 Uiso 1 1 calc R U . . .
C00G C 0.3226(2) 0.7281(2) 0.1192(2) 0.0264(4) Uani 1 1 d . . . . .
H00G H 0.353034 0.646071 0.058586 0.032 Uiso 1 1 calc R U . . .
C00H C 0.6479(2) 0.7075(2) 0.4958(2) 0.0257(4) Uani 1 1 d . . . . .
H00H H 0.590775 0.669494 0.545543 0.031 Uiso 1 1 calc R U . . .
C00I C 0.2437(3) 0.2244(2) 0.0497(2) 0.0300(5) Uani 1 1 d . . . . .
H00I H 0.213937 0.127398 -0.010210 0.036 Uiso 1 1 calc R U . . .
C00J C 0.2249(2) 0.7742(2) 0.7334(2) 0.0297(5) Uani 1 1 d . . . . .
H00J H 0.192762 0.794704 0.819157 0.036 Uiso 1 1 calc R U . . .
C00K C 0.1766(2) 0.4558(2) 0.1629(2) 0.0238(4) Uani 1 1 d . . . . .
C00L C 0.4441(2) 0.4280(2) 0.2061(2) 0.0260(4) Uani 1 1 d . . . . .
H00L H 0.549846 0.465898 0.249698 0.031 Uiso 1 1 calc R U . . .
C00M C 0.4005(2) 0.2826(2) 0.1163(2) 0.0294(4) Uani 1 1 d . . . . .
H00M H 0.476453 0.224815 0.101073 0.035 Uiso 1 1 calc R U . . .
C00N C 0.8221(2) 0.8183(2) 0.3487(2) 0.0299(5) Uani 1 1 d . . . . .
H00N H 0.880214 0.854758 0.298343 0.036 Uiso 1 1 calc R U . . .
C00O C 0.3853(2) 0.6789(2) 0.3358(2) 0.0218(4) Uani 1 1 d . . . . .
C00P C 0.3186(2) 0.8793(2) 0.7127(2) 0.0280(4) Uani 1 1 d . . . . .
H00P H 0.349997 0.970892 0.785542 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00K 1.7488(19) . ?
N002 C007 1.378(3) . ?
N002 C00G 1.362(3) . ?
N002 C00O 1.494(2) . ?
N003 C00C 1.384(3) . ?
N003 C00G 1.319(3) . ?
C004 C00K 1.404(3) . ?
C004 C00L 1.397(3) . ?
C004 C00O 1.547(3) . ?
C005 H005 0.9300 . ?
C005 C008 1.385(3) . ?
C005 C00D 1.390(3) . ?
C006 C00F 1.390(3) . ?
C006 C00H 1.398(3) . ?
C006 C00O 1.552(2) . ?
C007 H007 0.9300 . ?
C007 C00C 1.351(3) . ?
C008 C00B 1.400(3) . ?
C008 C00O 1.548(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.384(3) . ?
C009 C00N 1.379(3) . ?
C00A H00A 0.9300 . ?
C00A C00H 1.386(3) . ?
C00B H00B 0.9300 . ?
C00B C00P 1.386(3) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00J 1.379(3) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.387(3) . ?
C00E C00K 1.387(3) . ?
C00F H00F 0.9300 . ?
C00F C00N 1.395(3) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00M 1.386(3) . ?
C00J H00J 0.9300 . ?
C00J C00P 1.388(3) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.394(3) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00P H00P 0.9300 . ?

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 N002 C00O 129.54(16) . . ?
C00G N002 C007 105.81(16) . . ?
C00G N002 C00O 124.56(16) . . ?
C00G N003 C00C 104.42(17) . . ?
C00K C004 C00O 122.65(17) . . ?
C00L C004 C00K 116.39(18) . . ?
C00L C004 C00O 120.94(17) . . ?
C008 C005 H005 119.4 . . ?
C008 C005 C00D 121.27(19) . . ?
C00D C005 H005 119.4 . . ?
C00F C006 C00H 117.91(17) . . ?
C00F C006 C00O 122.18(17) . . ?
C00H C006 C00O 119.90(17) . . ?
N002 C007 H007 126.7 . . ?
C00C C007 N002 106.60(17) . . ?
C00C C007 H007 126.7 . . ?
C005 C008 C00B 117.77(17) . . ?
C005 C008 C00O 122.48(17) . . ?
C00B C008 C00O 119.40(17) . . ?
C00A C009 H009 120.3 . . ?
C00N C009 H009 120.3 . . ?
C00N C009 C00A 119.37(18) . . ?
C009 C00A H00A 119.7 . . ?
C009 C00A C00H 120.55(19) . . ?
C00H C00A H00A 119.7 . . ?
C008 C00B H00B 119.6 . . ?
C00P C00B C008 120.88(19) . . ?
C00P C00B H00B 119.6 . . ?
N003 C00C H00C 124.7 . . ?
C007 C00C N003 110.54(18) . . ?
C007 C00C H00C 124.7 . . ?
C005 C00D H00D 119.7 . . ?
C00J C00D C005 120.64(19) . . ?
C00J C00D H00D 119.7 . . ?
C00I C00E H00E 120.1 . . ?
C00I C00E C00K 119.76(19) . . ?
C00K C00E H00E 120.1 . . ?
C006 C00F H00F 119.5 . . ?
C006 C00F C00N 121.08(19) . . ?
C00N C00F H00F 119.5 . . ?
N002 C00G H00G 123.7 . . ?
N003 C00G N002 112.62(18) . . ?
N003 C00G H00G 123.7 . . ?
C006 C00H H00H 119.6 . . ?
C00A C00H C006 120.86(19) . . ?
C00A C00H H00H 119.6 . . ?
C00E C00I H00I 120.1 . . ?
C00M C00I C00E 119.73(19) . . ?
C00M C00I H00I 120.1 . . ?
C00D C00J H00J 120.6 . . ?
C00D C00J C00P 118.80(19) . . ?
C00P C00J H00J 120.6 . . ?
C004 C00K Cl01 121.92(15) . . ?
C00E C00K Cl01 115.84(15) . . ?
C00E C00K C004 122.23(18) . . ?
C004 C00L H00L 118.9 . . ?
C00M C00L C004 122.11(18) . . ?
C00M C00L H00L 118.9 . . ?
C00I C00M C00L 119.78(19) . . ?
C00I C00M H00M 120.1 . . ?
C00L C00M H00M 120.1 . . ?
C009 C00N C00F 120.21(19) . . ?
C009 C00N H00N 119.9 . . ?
C00F C00N H00N 119.9 . . ?
N002 C00O C004 107.06(15) . . ?
N002 C00O C006 108.70(15) . . ?
N002 C00O C008 110.96(15) . . ?
C004 C00O C006 111.29(15) . . ?
C004 C00O C008 111.25(15) . . ?
C008 C00O C006 107.57(15) . . ?
C00B C00P C00J 120.62(19) . . ?
C00B C00P H00P 119.7 . . ?
C00J C00P H00P 119.7 . . ?

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
N002 C007 C00C N003 0.3(2) . . . . ?
C004 C00L C00M C00I 0.3(3) . . . . ?
C005 C008 C00B C00P -1.5(3) . . . . ?
C005 C008 C00O N002 119.59(19) . . . . ?
C005 C008 C00O C004 0.5(2) . . . . ?
C005 C008 C00O C006 -121.63(19) . . . . ?
C005 C00D C00J C00P -0.5(3) . . . . ?
C006 C00F C00N C009 0.0(3) . . . . ?
C007 N002 C00G N003 0.7(2) . . . . ?
C007 N002 C00O C004 145.58(18) . . . . ?
C007 N002 C00O C006 -94.1(2) . . . . ?
C007 N002 C00O C008 24.0(3) . . . . ?
C008 C005 C00D C00J -0.3(3) . . . . ?
C008 C00B C00P C00J 0.7(3) . . . . ?
C009 C00A C00H C006 -0.3(3) . . . . ?
C00A C009 C00N C00F 0.9(3) . . . . ?
C00B C008 C00O N002 -67.3(2) . . . . ?
C00B C008 C00O C004 173.62(16) . . . . ?
C00B C008 C00O C006 51.5(2) . . . . ?
C00C N003 C00G N002 -0.5(2) . . . . ?
C00D C005 C008 C00B 1.3(3) . . . . ?
C00D C005 C008 C00O 174.55(17) . . . . ?
C00D C00J C00P C00B 0.3(3) . . . . ?
C00E C00I C00M C00L 0.1(3) . . . . ?
C00F C006 C00H C00A 1.1(3) . . . . ?
C00F C006 C00O N002 -25.7(2) . . . . ?
C00F C006 C00O C004 91.9(2) . . . . ?
C00F C006 C00O C008 -145.96(18) . . . . ?
C00G N002 C007 C00C -0.6(2) . . . . ?
C00G N002 C00O C004 -38.3(2) . . . . ?
C00G N002 C00O C006 82.0(2) . . . . ?
C00G N002 C00O C008 -159.88(17) . . . . ?
C00G N003 C00C C007 0.1(2) . . . . ?
C00H C006 C00F C00N -1.0(3) . . . . ?
C00H C006 C00O N002 154.83(17) . . . . ?
C00H C006 C00O C004 -87.5(2) . . . . ?
C00H C006 C00O C008 34.6(2) . . . . ?
C00I C00E C00K Cl01 -178.76(16) . . . . ?
C00I C00E C00K C004 0.2(3) . . . . ?
C00K C004 C00L C00M -0.5(3) . . . . ?
C00K C004 C00O N002 -53.0(2) . . . . ?
C00K C004 C00O C006 -171.69(17) . . . . ?
C00K C004 C00O C008 68.4(2) . . . . ?
C00K C00E C00I C00M -0.4(3) . . . . ?
C00L C004 C00K Cl01 179.15(15) . . . . ?
C00L C004 C00K C00E 0.2(3) . . . . ?
C00L C004 C00O N002 128.10(18) . . . . ?
C00L C004 C00O C006 9.4(2) . . . . ?
C00L C004 C00O C008 -110.5(2) . . . . ?
C00N C009 C00A C00H -0.7(3) . . . . ?
C00O N002 C007 C00C 176.10(17) . . . . ?
C00O N002 C00G N003 -176.20(16) . . . . ?
C00O C004 C00K Cl01 0.2(3) . . . . ?
C00O C004 C00K C00E -178.69(18) . . . . ?
C00O C004 C00L C00M 178.43(18) . . . . ?
C00O C006 C00F C00N 179.58(18) . . . . ?
C00O C006 C00H C00A -179.41(18) . . . . ?
C00O C008 C00B C00P -174.95(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.627
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Alpha-NIF-100K-XZLI
_database_code_depnum_ccdc_archive 'CCDC 1918294'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;School of pharmaceutical Science, Sun Yat sen University
China
;
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2018-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            nifedipine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 N2 O6'
_chemical_formula_sum            'C17 H18 N2 O6'
_chemical_formula_weight         346.33
_chemical_melting_point          445K
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6219(4)
_cell_length_b                   10.4085(4)
_cell_length_c                   14.7800(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.879(3)
_cell_angle_gamma                90
_cell_volume                     1628.13(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7919
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8780
_cell_measurement_theta_min      3.0790
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.712
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10268
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.509
_diffrn_reflns_theta_min         5.204
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -31.00   0.50    0.05    --  -46.37 -36.00  14.00  174
  2  ω     34.00  79.00   0.50    0.05    --   46.37  36.00 170.00   90
  3  ω     -1.00  57.00   0.50    0.05    --   46.37 -36.00  14.00  116
  4  ω   -169.00 -90.00   0.50    0.05    -- -100.00 -36.00  14.00  158
  5  ω   -115.00 -27.00   0.50    0.05    -- -100.00  36.00 170.00  176
  6  ω    138.00 163.00   0.50    0.05    --  107.00  36.00 170.00   50
  7  ω     94.00 119.00   0.50    0.05    --  107.00  36.00 170.00   50
  8  ω     47.00  72.00   0.50    0.05    --  107.00 -36.00  14.00   50
  9  ω    -41.00 -16.00   0.50    0.05    --  -46.37  36.00 170.00   50
 10  ω     16.00  95.00   0.50    0.05    --   46.37-125.00 -90.00  158
 11  ω    -61.00 -28.00   0.50    0.05    -- -100.00 125.00-180.00   66
 12  ω   -113.00 -25.00   0.50    0.05    -- -100.00  15.00   0.00  176
 13  ω   -117.00 -73.00   0.50    0.05    -- -100.00  61.00   0.00   88
 14  ω    -62.00 -27.00   0.50    0.05    -- -100.00  61.00   0.00   70
 15  ω   -113.00 -28.00   0.50    0.05    -- -100.00  45.00   0.00  170
 16  ω    103.00 166.00   0.50    0.05    --  107.00  45.00 -60.00  126
 17  ω     39.00  89.00   0.50    0.05    --  107.00 -95.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1132664000
_diffrn_orient_matrix_UB_12      -0.0030968000
_diffrn_orient_matrix_UB_13      0.0585891000
_diffrn_orient_matrix_UB_21      -0.0826119000
_diffrn_orient_matrix_UB_22      0.0675998000
_diffrn_orient_matrix_UB_23      -0.0764535000
_diffrn_orient_matrix_UB_31      -0.0395898000
_diffrn_orient_matrix_UB_32      -0.1316604000
_diffrn_orient_matrix_UB_33      -0.0405501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2957
_reflns_number_total             3196
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.318
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.029
_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)+(0.0685P)²+0.9950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1269
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), C00A(H00A), C00J(H00J), C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00M(H00B,H00D,H00E), C00N(H00F,H00G,H00H), C00O(H00I,H00M,H00N), C00P(H00O,
 H00P,H00Q)
;
_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
O001 O 0.45742(10) 0.78209(11) 0.53509(8) 0.0264(3) Uani 1 1 d . . . . .
O002 O 0.36790(10) 0.73310(11) 0.66269(8) 0.0264(3) Uani 1 1 d . . . . .
O003 O 0.85930(11) 0.36868(11) 0.47450(7) 0.0256(3) Uani 1 1 d . . . . .
O004 O 0.65567(12) 0.80249(12) 0.39810(8) 0.0303(3) Uani 1 1 d . . . . .
O005 O 0.82425(12) 0.57152(11) 0.43138(8) 0.0315(3) Uani 1 1 d . . . . .
O006 O 0.84915(14) 0.86170(13) 0.38674(8) 0.0383(3) Uani 1 1 d . . . . .
N007 N 0.64221(13) 0.43337(13) 0.69488(9) 0.0239(3) Uani 1 1 d . . . . .
H007 H 0.648279 0.386274 0.742860 0.029 Uiso 1 1 calc R . . . .
N008 N 0.76235(14) 0.82934(13) 0.43145(9) 0.0249(3) Uani 1 1 d . . . . .
C009 C 0.73804(13) 0.73885(14) 0.58723(10) 0.0186(3) Uani 1 1 d . . . . .
C00A C 0.77422(14) 0.75258(15) 0.68029(10) 0.0209(3) Uani 1 1 d . . . . .
H00A H 0.745521 0.692650 0.720429 0.025 Uiso 1 1 calc R . . . .
C00B C 0.54528(13) 0.61176(15) 0.61871(10) 0.0200(3) Uani 1 1 d . . . . .
C00C C 0.65412(13) 0.62306(14) 0.55791(10) 0.0182(3) Uani 1 1 d . . . . .
H00C H 0.618994 0.636269 0.495119 0.022 Uiso 1 1 calc R . . . .
C00D C 0.78809(14) 0.83023(15) 0.53106(10) 0.0202(3) Uani 1 1 d . . . . .
C00E C 0.73071(14) 0.41722(15) 0.63252(10) 0.0212(3) Uani 1 1 d . . . . .
C00F C 0.44763(14) 0.71051(15) 0.61003(10) 0.0204(3) Uani 1 1 d . . . . .
C00G C 0.73324(14) 0.50027(14) 0.56233(10) 0.0190(3) Uani 1 1 d . . . . .
C00H C 0.54484(14) 0.52080(15) 0.68433(10) 0.0215(3) Uani 1 1 d . . . . .
C00I C 0.80992(14) 0.48575(14) 0.48473(10) 0.0196(3) Uani 1 1 d . . . . .
C00J C 0.86640(14) 0.93007(15) 0.56425(11) 0.0233(3) Uani 1 1 d . . . . .
H00J H 0.898144 0.988473 0.524338 0.028 Uiso 1 1 calc R . . . .
C00K C 0.89670(14) 0.94197(15) 0.65666(11) 0.0239(3) Uani 1 1 d . . . . .
H00K H 0.947088 1.009516 0.679599 0.029 Uiso 1 1 calc R . . . .
C00L C 0.85095(14) 0.85178(16) 0.71479(11) 0.0235(3) Uani 1 1 d . . . . .
H00L H 0.871848 0.857955 0.777028 0.028 Uiso 1 1 calc R . . . .
C00M C 0.92600(16) 0.35339(17) 0.39425(11) 0.0287(4) Uani 1 1 d . . . . .
H00B H 0.869289 0.369194 0.341329 0.043 Uiso 1 1 calc GR . . . .
H00D H 0.958319 0.267413 0.392030 0.043 Uiso 1 1 calc GR . . . .
H00E H 0.994817 0.413365 0.395938 0.043 Uiso 1 1 calc GR . . . .
C00N C 0.44572(16) 0.50355(18) 0.74992(12) 0.0300(4) Uani 1 1 d . . . . .
H00F H 0.453983 0.419801 0.776983 0.045 Uiso 1 1 calc GR . . . .
H00G H 0.363428 0.511948 0.718206 0.045 Uiso 1 1 calc GR . . . .
H00H H 0.456358 0.567865 0.796492 0.045 Uiso 1 1 calc GR . . . .
C00O C 0.81725(16) 0.30531(16) 0.65580(12) 0.0276(4) Uani 1 1 d . . . . .
H00I H 0.849486 0.310987 0.718355 0.041 Uiso 1 1 calc GR . . . .
H00M H 0.886269 0.307104 0.617894 0.041 Uiso 1 1 calc GR . . . .
H00N H 0.771181 0.226482 0.646006 0.041 Uiso 1 1 calc GR . . . .
C00P C 0.36746(16) 0.88461(17) 0.52101(13) 0.0316(4) Uani 1 1 d . . . . .
H00O H 0.377571 0.925390 0.463822 0.047 Uiso 1 1 calc GR . . . .
H00P H 0.381222 0.946423 0.569040 0.047 Uiso 1 1 calc GR . . . .
H00Q H 0.283431 0.850568 0.520754 0.047 Uiso 1 1 calc GR . . . .


_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
O001 C00F 1.3463(19) . ?
O001 C00P 1.4357(19) . ?
O002 C00F 1.2208(19) . ?
O003 C00I 1.3403(19) . ?
O003 C00M 1.4411(18) . ?
O004 N008 1.2288(19) . ?
O005 C00I 1.2092(19) . ?
O006 N008 1.2263(19) . ?
N007 H007 0.8600 . ?
N007 C00E 1.382(2) . ?
N007 C00H 1.376(2) . ?
N008 C00D 1.474(2) . ?
C009 C00A 1.404(2) . ?
C009 C00C 1.539(2) . ?
C009 C00D 1.397(2) . ?
C00A H00A 0.9300 . ?
C00A C00L 1.386(2) . ?
C00B C00C 1.5280(19) . ?
C00B C00F 1.458(2) . ?
C00B C00H 1.356(2) . ?
C00C H00C 0.9800 . ?
C00C C00G 1.528(2) . ?
C00D C00J 1.394(2) . ?
C00E C00G 1.352(2) . ?
C00E C00O 1.505(2) . ?
C00G C00I 1.470(2) . ?
C00H C00N 1.501(2) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.382(2) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.388(2) . ?
C00L H00L 0.9300 . ?
C00M H00B 0.9600 . ?
C00M H00D 0.9600 . ?
C00M H00E 0.9600 . ?
C00N H00F 0.9600 . ?
C00N H00G 0.9600 . ?
C00N H00H 0.9600 . ?
C00O H00I 0.9600 . ?
C00O H00M 0.9600 . ?
C00O H00N 0.9600 . ?
C00P H00O 0.9600 . ?
C00P H00P 0.9600 . ?
C00P H00Q 0.9600 . ?

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
C00F O001 C00P 115.70(13) . . ?
C00I O003 C00M 114.69(12) . . ?
C00E N007 H007 118.2 . . ?
C00H N007 H007 118.2 . . ?
C00H N007 C00E 123.52(13) . . ?
O004 N008 C00D 119.23(13) . . ?
O006 N008 O004 123.80(14) . . ?
O006 N008 C00D 116.89(14) . . ?
C00A C009 C00C 117.35(13) . . ?
C00D C009 C00A 115.25(14) . . ?
C00D C009 C00C 127.33(13) . . ?
C009 C00A H00A 118.7 . . ?
C00L C00A C009 122.69(14) . . ?
C00L C00A H00A 118.7 . . ?
C00F C00B C00C 117.52(13) . . ?
C00H C00B C00C 121.56(13) . . ?
C00H C00B C00F 120.63(13) . . ?
C009 C00C H00C 108.8 . . ?
C00B C00C C009 110.10(12) . . ?
C00B C00C H00C 108.8 . . ?
C00B C00C C00G 110.57(12) . . ?
C00G C00C C009 109.86(11) . . ?
C00G C00C H00C 108.8 . . ?
C009 C00D N008 122.78(14) . . ?
C00J C00D N008 114.23(13) . . ?
C00J C00D C009 122.99(14) . . ?
N007 C00E C00O 112.25(13) . . ?
C00G C00E N007 119.54(14) . . ?
C00G C00E C00O 128.19(14) . . ?
O001 C00F C00B 111.00(13) . . ?
O002 C00F O001 121.61(14) . . ?
O002 C00F C00B 127.35(15) . . ?
C00E C00G C00C 121.38(13) . . ?
C00E C00G C00I 125.55(14) . . ?
C00I C00G C00C 113.07(12) . . ?
N007 C00H C00N 114.16(13) . . ?
C00B C00H N007 119.63(13) . . ?
C00B C00H C00N 126.21(14) . . ?
O003 C00I C00G 115.44(13) . . ?
O005 C00I O003 121.70(13) . . ?
O005 C00I C00G 122.80(14) . . ?
C00D C00J H00J 120.1 . . ?
C00K C00J C00D 119.76(14) . . ?
C00K C00J H00J 120.1 . . ?
C00J C00K H00K 120.4 . . ?
C00J C00K C00L 119.14(15) . . ?
C00L C00K H00K 120.4 . . ?
C00A C00L C00K 120.14(15) . . ?
C00A C00L H00L 119.9 . . ?
C00K C00L H00L 119.9 . . ?
O003 C00M H00B 109.5 . . ?
O003 C00M H00D 109.5 . . ?
O003 C00M H00E 109.5 . . ?
H00B C00M H00D 109.5 . . ?
H00B C00M H00E 109.5 . . ?
H00D C00M H00E 109.5 . . ?
C00H C00N H00F 109.5 . . ?
C00H C00N H00G 109.5 . . ?
C00H C00N H00H 109.5 . . ?
H00F C00N H00G 109.5 . . ?
H00F C00N H00H 109.5 . . ?
H00G C00N H00H 109.5 . . ?
C00E C00O H00I 109.5 . . ?
C00E C00O H00M 109.5 . . ?
C00E C00O H00N 109.5 . . ?
H00I C00O H00M 109.5 . . ?
H00I C00O H00N 109.5 . . ?
H00M C00O H00N 109.5 . . ?
O001 C00P H00O 109.5 . . ?
O001 C00P H00P 109.5 . . ?
O001 C00P H00Q 109.5 . . ?
H00O C00P H00P 109.5 . . ?
H00O C00P H00Q 109.5 . . ?
H00P C00P H00Q 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.349
_oxdiff_exptl_absorpt_empirical_full_min 0.361
####################################################################### 
# 
# 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_Ciclopirox-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987333'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Ciclopirox
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N O2'
_chemical_formula_sum            'C12 H17 N O2'
_chemical_formula_weight         207.26

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   25.3104(4)
_cell_length_b                   27.6509(4)
_cell_length_c                   19.1485(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.1260(10)
_cell_angle_gamma                90
_cell_volume                     13324.7(3)
_cell_formula_units_Z            48
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    37171
_cell_measurement_theta_min      2.3870
_cell_measurement_theta_max      76.1990

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             5376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.674
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            89852
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.374
_diffrn_reflns_theta_max         76.582
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             26683
_reflns_number_gt                20563
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1061P)²+16.2082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         26683
_refine_ls_number_parameters     1621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2196
_refine_ls_wR_factor_gt          0.2011
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.96861(8) 0.09154(7) 0.48870(11) 0.0259(4) Uani 1 1 d . . . . .
N2 N 0.70365(8) 0.10365(7) 0.70597(11) 0.0258(4) Uani 1 1 d . . . . .
N3 N 0.31036(8) 0.41243(7) 0.30923(11) 0.0275(4) Uani 1 1 d . . . . .
N4 N 0.37436(8) 0.58297(8) 0.39330(12) 0.0312(5) Uani 1 1 d . . . . .
N5 N 0.53207(8) 0.67574(7) 0.54720(11) 0.0258(4) Uani 1 1 d . . . . .
N6 N 0.47022(8) 0.85037(7) 0.46703(11) 0.0263(4) Uani 1 1 d . . . . .
N7 N 0.65257(8) 0.92185(7) 0.62324(11) 0.0258(4) Uani 1 1 d . . . . .
N8 N 0.18919(8) 0.84626(8) 0.69636(12) 0.0299(5) Uani 1 1 d . . . . .
N9 N 0.13800(8) 0.67217(8) 0.60218(11) 0.0294(4) Uani 1 1 d . . . . .
N10 N 0.03694(9) 0.42889(8) 0.56887(14) 0.0383(5) Uani 1 1 d . . . . .
N11 N 0.20322(8) 0.35326(7) 0.71699(11) 0.0273(4) Uani 1 1 d . . . . .
N12 N 0.14078(8) 0.17645(7) 0.65277(12) 0.0314(5) Uani 1 1 d . . . . .
O1 O 1.01845(7) 0.07257(6) 0.48173(10) 0.0321(4) Uani 1 1 d . . . . .
H1 H 1.017954 0.043217 0.487770 0.048 Uiso 1 1 calc R U . . .
O2 O 0.94190(7) 0.01533(6) 0.50879(11) 0.0376(4) Uani 1 1 d . . . . .
O3 O 0.65622(7) 0.07950(6) 0.71027(10) 0.0308(4) Uani 1 1 d . . . . .
H3 H 0.658684 0.051766 0.695793 0.046 Uiso 1 1 calc R U . . .
O4 O 0.73714(7) 0.03259(6) 0.67097(10) 0.0340(4) Uani 1 1 d . . . . .
O5 O 0.35899(7) 0.43154(6) 0.29681(10) 0.0323(4) Uani 1 1 d . . . . .
H5 H 0.364658 0.456301 0.319972 0.048 Uiso 1 1 calc R U . . .
O6 O 0.28401(7) 0.48898(7) 0.33050(11) 0.0384(4) Uani 1 1 d . . . . .
O7 O 0.32728(8) 0.56055(7) 0.40511(12) 0.0434(5) Uani 1 1 d . . . . .
H7 H 0.320611 0.539011 0.376067 0.065 Uiso 1 1 calc R U . . .
O8 O 0.40265(8) 0.51108(7) 0.35367(12) 0.0450(5) Uani 1 1 d . . . . .
O9 O 0.48499(7) 0.69703(6) 0.56167(10) 0.0317(4) Uani 1 1 d . . . . .
H9 H 0.481014 0.722774 0.540495 0.048 Uiso 1 1 calc R U . . .
O10 O 0.56056(7) 0.75070(6) 0.52133(11) 0.0372(4) Uani 1 1 d . . . . .
O11 O 0.51766(7) 0.82766(6) 0.45761(10) 0.0310(4) Uani 1 1 d . . . . .
H11 H 0.521793 0.804265 0.483952 0.047 Uiso 1 1 calc R U . . .
O12 O 0.44408(7) 0.78038(6) 0.51417(11) 0.0356(4) Uani 1 1 d . . . . .
O13 O 0.69878(7) 0.94607(6) 0.61125(10) 0.0307(4) Uani 1 1 d . . . . .
H13 H 0.701493 0.970821 0.634955 0.046 Uiso 1 1 calc R U . . .
O14 O 0.62773(7) 0.99029(6) 0.67564(11) 0.0352(4) Uani 1 1 d . . . . .
O15 O 0.14022(7) 0.82442(7) 0.69749(11) 0.0374(4) Uani 1 1 d . . . . .
H15 H 0.139503 0.799184 0.674919 0.056 Uiso 1 1 calc R U . . .
O16 O 0.21850(8) 0.77560(7) 0.65439(12) 0.0425(5) Uani 1 1 d . . . . .
O17 O 0.18336(7) 0.69713(7) 0.58953(11) 0.0401(5) Uani 1 1 d . . . . .
H17 H 0.187115 0.720651 0.615663 0.060 Uiso 1 1 calc R U . . .
O18 O 0.10398(8) 0.74283(7) 0.63814(12) 0.0412(5) Uani 1 1 d . . . . .
O19 O -0.00764(8) 0.45368(8) 0.58539(14) 0.0527(6) Uani 1 1 d . . . . .
H19 H -0.021095 0.468144 0.550550 0.079 Uiso 1 1 calc R U . . .
O20 O 0.06137(9) 0.49629(8) 0.51219(14) 0.0531(6) Uani 1 1 d . . . . .
O21 O 0.15731(7) 0.33134(6) 0.73400(10) 0.0327(4) Uani 1 1 d . . . . .
H21 H 0.156413 0.303281 0.720055 0.049 Uiso 1 1 calc R U . . .
O22 O 0.23562(7) 0.27819(7) 0.69922(11) 0.0374(4) Uani 1 1 d . . . . .
O23 O 0.19070(7) 0.19557(7) 0.64604(12) 0.0396(5) Uani 1 1 d . . . . .
H23 H 0.194188 0.221221 0.667519 0.059 Uiso 1 1 calc R U . . .
O24 O 0.12269(10) 0.24487(7) 0.71057(16) 0.0629(7) Uani 1 1 d . . . . .
C1 C 1.02001(10) 0.16520(10) 0.38893(14) 0.0326(6) Uani 1 1 d . . . . .
H1A H 0.991341 0.181775 0.360932 0.039 Uiso 1 1 calc R U . . .
H1B H 1.019773 0.131603 0.374337 0.039 Uiso 1 1 calc R U . . .
C2 C 1.07312(11) 0.18838(10) 0.37693(16) 0.0373(6) Uani 1 1 d . . . . .
H2A H 1.101835 0.170245 0.402330 0.045 Uiso 1 1 calc R U . . .
H2B H 1.077759 0.187064 0.327331 0.045 Uiso 1 1 calc R U . . .
C3 C 1.07575(12) 0.24083(10) 0.40146(18) 0.0436(7) Uani 1 1 d . . . . .
H3A H 1.111067 0.253476 0.397601 0.052 Uiso 1 1 calc R U . . .
H3B H 1.050657 0.259946 0.371147 0.052 Uiso 1 1 calc R U . . .
C4 C 1.06316(13) 0.24571(10) 0.47660(19) 0.0470(8) Uani 1 1 d . . . . .
H4A H 1.061690 0.279732 0.488580 0.056 Uiso 1 1 calc R U . . .
H4B H 1.091444 0.230965 0.507632 0.056 Uiso 1 1 calc R U . . .
C5 C 1.01010(11) 0.22169(9) 0.48831(16) 0.0372(6) Uani 1 1 d . . . . .
H5A H 0.981132 0.238146 0.460717 0.045 Uiso 1 1 calc R U . . .
H5B H 1.004264 0.223965 0.537453 0.045 Uiso 1 1 calc R U . . .
C6 C 1.01156(10) 0.16828(8) 0.46623(13) 0.0275(5) Uani 1 1 d . . . . .
H6 H 1.042297 0.153227 0.493245 0.033 Uiso 1 1 calc R U . . .
C7 C 0.96305(10) 0.14061(8) 0.48097(12) 0.0255(5) Uani 1 1 d . . . . .
C8 C 0.91348(10) 0.15911(9) 0.48550(13) 0.0291(5) Uani 1 1 d . . . . .
H8 H 0.907936 0.192220 0.480208 0.035 Uiso 1 1 calc R U . . .
C9 C 0.87051(10) 0.12892(9) 0.49808(13) 0.0290(5) Uani 1 1 d . . . . .
C10 C 0.87891(10) 0.08012(9) 0.50753(14) 0.0310(5) Uani 1 1 d . . . . .
H10 H 0.850775 0.060514 0.517354 0.037 Uiso 1 1 calc R U . . .
C11 C 0.92946(10) 0.05891(9) 0.50266(14) 0.0298(5) Uani 1 1 d . . . . .
C12 C 0.81575(11) 0.14973(10) 0.49959(16) 0.0382(6) Uani 1 1 d . . . . .
H12A H 0.816883 0.184040 0.492184 0.057 Uiso 1 1 calc R U . . .
H12B H 0.791961 0.135173 0.463165 0.057 Uiso 1 1 calc R U . . .
H12C H 0.803460 0.143280 0.544393 0.057 Uiso 1 1 calc R U . . .
C13 C 0.61765(10) 0.18760(9) 0.68097(13) 0.0302(5) Uani 1 1 d . . . . .
H13A H 0.634603 0.211930 0.654459 0.036 Uiso 1 1 calc R U . . .
H13B H 0.610734 0.159482 0.651099 0.036 Uiso 1 1 calc R U . . .
C14 C 0.56509(11) 0.20742(10) 0.70164(15) 0.0371(6) Uani 1 1 d . . . . .
H14A H 0.543504 0.218572 0.659837 0.045 Uiso 1 1 calc R U . . .
H14B H 0.545904 0.181642 0.722280 0.045 Uiso 1 1 calc R U . . .
C15 C 0.57365(11) 0.24911(10) 0.75397(15) 0.0373(6) Uani 1 1 d . . . . .
H15A H 0.587862 0.276769 0.731036 0.045 Uiso 1 1 calc R U . . .
H15B H 0.539804 0.258457 0.769306 0.045 Uiso 1 1 calc R U . . .
C16 C 0.61174(11) 0.23491(10) 0.81748(15) 0.0352(6) Uani 1 1 d . . . . .
H16A H 0.595820 0.209607 0.843397 0.042 Uiso 1 1 calc R U . . .
H16B H 0.618127 0.262616 0.848294 0.042 Uiso 1 1 calc R U . . .
C17 C 0.66471(10) 0.21692(10) 0.79494(14) 0.0324(6) Uani 1 1 d . . . . .
H17A H 0.681612 0.242672 0.771056 0.039 Uiso 1 1 calc R U . . .
H17B H 0.688280 0.207687 0.836068 0.039 Uiso 1 1 calc R U . . .
C18 C 0.65500(9) 0.17352(8) 0.74591(12) 0.0245(5) Uani 1 1 d . . . . .
H18 H 0.636971 0.148702 0.771174 0.029 Uiso 1 1 calc R U . . .
C19 C 0.70538(9) 0.15137(8) 0.72473(12) 0.0239(5) Uani 1 1 d . . . . .
C20 C 0.75258(10) 0.17491(9) 0.72226(13) 0.0276(5) Uani 1 1 d . . . . .
H20 H 0.755397 0.207321 0.735101 0.033 Uiso 1 1 calc R U . . .
C21 C 0.79704(10) 0.15084(9) 0.70054(14) 0.0312(5) Uani 1 1 d . . . . .
C22 C 0.79303(10) 0.10272(9) 0.68257(14) 0.0312(5) Uani 1 1 d . . . . .
H22 H 0.822592 0.087010 0.668458 0.037 Uiso 1 1 calc R U . . .
C23 C 0.74531(10) 0.07639(9) 0.68488(13) 0.0281(5) Uani 1 1 d . . . . .
C24 C 0.84816(12) 0.17784(11) 0.69704(19) 0.0477(8) Uani 1 1 d . . . . .
H24A H 0.843819 0.210757 0.711310 0.072 Uiso 1 1 calc R U . . .
H24B H 0.875829 0.162833 0.727808 0.072 Uiso 1 1 calc R U . . .
H24C H 0.857520 0.177191 0.649769 0.072 Uiso 1 1 calc R U . . .
C25 C 0.35733(10) 0.34412(9) 0.20290(13) 0.0288(5) Uani 1 1 d . . . . .
H25A H 0.326437 0.331861 0.173953 0.035 Uiso 1 1 calc R U . . .
H25B H 0.359852 0.378579 0.194389 0.035 Uiso 1 1 calc R U . . .
C26 C 0.40722(10) 0.31893(9) 0.18283(14) 0.0313(5) Uani 1 1 d . . . . .
H26A H 0.438326 0.333049 0.209112 0.038 Uiso 1 1 calc R U . . .
H26B H 0.410107 0.323861 0.133224 0.038 Uiso 1 1 calc R U . . .
C27 C 0.40548(12) 0.26476(10) 0.19820(16) 0.0390(6) Uani 1 1 d . . . . .
H27A H 0.377096 0.249980 0.167374 0.047 Uiso 1 1 calc R U . . .
H27B H 0.438720 0.250057 0.188509 0.047 Uiso 1 1 calc R U . . .
C28 C 0.39646(12) 0.25500(10) 0.27418(16) 0.0388(6) Uani 1 1 d . . . . .
H28A H 0.427142 0.265931 0.304798 0.047 Uiso 1 1 calc R U . . .
H28B H 0.392727 0.220459 0.281029 0.047 Uiso 1 1 calc R U . . .
C29 C 0.34670(11) 0.28082(9) 0.29412(14) 0.0312(5) Uani 1 1 d . . . . .
H29A H 0.342935 0.275176 0.343337 0.037 Uiso 1 1 calc R U . . .
H29B H 0.315506 0.267902 0.266526 0.037 Uiso 1 1 calc R U . . .
C30 C 0.35075(10) 0.33530(9) 0.28072(13) 0.0271(5) Uani 1 1 d . . . . .
H30 H 0.382843 0.347215 0.308590 0.032 Uiso 1 1 calc R U . . .
C31 C 0.30444(10) 0.36338(9) 0.30189(12) 0.0263(5) Uani 1 1 d . . . . .
C32 C 0.25543(10) 0.34462(10) 0.31262(13) 0.0305(5) Uani 1 1 d . . . . .
H32 H 0.249591 0.311509 0.308124 0.037 Uiso 1 1 calc R U . . .
C33 C 0.21404(10) 0.37494(10) 0.33033(13) 0.0326(6) Uani 1 1 d . . . . .
C34 C 0.22293(10) 0.42365(10) 0.33804(14) 0.0330(6) Uani 1 1 d . . . . .
H34 H 0.195827 0.443316 0.351039 0.040 Uiso 1 1 calc R U . . .
C35 C 0.27221(10) 0.44483(9) 0.32679(14) 0.0309(5) Uani 1 1 d . . . . .
C36 C 0.16030(11) 0.35396(12) 0.33876(17) 0.0442(7) Uani 1 1 d . . . . .
H36A H 0.161115 0.319612 0.331650 0.066 Uiso 1 1 calc R U . . .
H36B H 0.151246 0.360665 0.385212 0.066 Uiso 1 1 calc R U . . .
H36C H 0.134233 0.368203 0.304811 0.066 Uiso 1 1 calc R U . . .
C37 C 0.29218(11) 0.66872(11) 0.36976(14) 0.0356(6) Uani 1 1 d . . . . .
H37A H 0.309167 0.691615 0.340939 0.043 Uiso 1 1 calc R U . . .
H37B H 0.283561 0.639949 0.341866 0.043 Uiso 1 1 calc R U . . .
C38 C 0.24103(11) 0.69094(12) 0.39152(16) 0.0423(7) Uani 1 1 d . . . . .
H38A H 0.218665 0.701273 0.349894 0.051 Uiso 1 1 calc R U . . .
H38B H 0.221750 0.666642 0.415125 0.051 Uiso 1 1 calc R U . . .
C39 C 0.25272(12) 0.73406(11) 0.44026(17) 0.0428(7) Uani 1 1 d . . . . .
H39A H 0.267080 0.760279 0.414421 0.051 Uiso 1 1 calc R U . . .
H39B H 0.219899 0.745222 0.456746 0.051 Uiso 1 1 calc R U . . .
C40 C 0.29210(11) 0.72093(10) 0.50293(15) 0.0360(6) Uani 1 1 d . . . . .
H40A H 0.276046 0.697431 0.531794 0.043 Uiso 1 1 calc R U . . .
H40B H 0.300423 0.749585 0.531198 0.043 Uiso 1 1 calc R U . . .
C41 C 0.34348(11) 0.69991(10) 0.47983(14) 0.0340(6) Uani 1 1 d . . . . .
H41A H 0.360960 0.724011 0.453531 0.041 Uiso 1 1 calc R U . . .
H41B H 0.367413 0.691116 0.520829 0.041 Uiso 1 1 calc R U . . .
C42 C 0.33070(10) 0.65539(9) 0.43417(13) 0.0280(5) Uani 1 1 d . . . . .
H42 H 0.312736 0.631999 0.461985 0.034 Uiso 1 1 calc R U . . .
C43 C 0.37879(10) 0.63084(9) 0.41041(13) 0.0270(5) Uani 1 1 d . . . . .
C44 C 0.42585(10) 0.65318(9) 0.40133(13) 0.0296(5) Uani 1 1 d . . . . .
H44 H 0.430629 0.685543 0.413640 0.035 Uiso 1 1 calc R U . . .
C45 C 0.46731(10) 0.62769(10) 0.37347(13) 0.0315(6) Uani 1 1 d . . . . .
C46 C 0.46023(10) 0.57945(10) 0.35695(14) 0.0325(6) Uani 1 1 d . . . . .
H46 H 0.487583 0.562738 0.338820 0.039 Uiso 1 1 calc R U . . .
C47 C 0.41269(10) 0.55445(9) 0.36666(14) 0.0315(5) Uani 1 1 d . . . . .
C48 C 0.51820(11) 0.65304(11) 0.36318(16) 0.0384(6) Uani 1 1 d . . . . .
H48A H 0.516005 0.686215 0.377381 0.058 Uiso 1 1 calc R U . . .
H48B H 0.547129 0.637525 0.391053 0.058 Uiso 1 1 calc R U . . .
H48C H 0.524083 0.651633 0.314520 0.058 Uiso 1 1 calc R U . . .
C49 C 0.48681(10) 0.60685(9) 0.65647(13) 0.0294(5) Uani 1 1 d . . . . .
H49A H 0.517557 0.591152 0.681289 0.035 Uiso 1 1 calc R U . . .
H49B H 0.487995 0.640896 0.668720 0.035 Uiso 1 1 calc R U . . .
C50 C 0.43605(11) 0.58418(9) 0.67797(15) 0.0350(6) Uani 1 1 d . . . . .
H50A H 0.405504 0.601294 0.655125 0.042 Uiso 1 1 calc R U . . .
H50B H 0.435542 0.587393 0.728332 0.042 Uiso 1 1 calc R U . . .
C51 C 0.43220(12) 0.53082(10) 0.65790(17) 0.0408(7) Uani 1 1 d . . . . .
H51A H 0.460928 0.513133 0.684044 0.049 Uiso 1 1 calc R U . . .
H51B H 0.398864 0.517738 0.670209 0.049 Uiso 1 1 calc R U . . .
C52 C 0.43534(11) 0.52426(10) 0.57965(16) 0.0378(6) Uani 1 1 d . . . . .
H52A H 0.404417 0.538898 0.553669 0.045 Uiso 1 1 calc R U . . .
H52B H 0.435058 0.490014 0.568608 0.045 Uiso 1 1 calc R U . . .
C53 C 0.48570(10) 0.54729(8) 0.55688(14) 0.0291(5) Uani 1 1 d . . . . .
H53A H 0.485878 0.543924 0.506484 0.035 Uiso 1 1 calc R U . . .
H53B H 0.516732 0.530809 0.579597 0.035 Uiso 1 1 calc R U . . .
C54 C 0.48803(10) 0.60098(8) 0.57676(13) 0.0255(5) Uani 1 1 d . . . . .
H54 H 0.456187 0.616600 0.553314 0.031 Uiso 1 1 calc R U . . .
C55 C 0.53560(9) 0.62666(8) 0.55419(12) 0.0240(5) Uani 1 1 d . . . . .
C56 C 0.58288(10) 0.60570(9) 0.54206(12) 0.0262(5) Uani 1 1 d . . . . .
H56 H 0.586896 0.572376 0.546554 0.031 Uiso 1 1 calc R U . . .
C57 C 0.62553(10) 0.63386(9) 0.52287(12) 0.0259(5) Uani 1 1 d . . . . .
C58 C 0.61902(10) 0.68297(9) 0.51487(13) 0.0288(5) Uani 1 1 d . . . . .
H58 H 0.646901 0.701360 0.501146 0.035 Uiso 1 1 calc R U . . .
C59 C 0.57107(10) 0.70634(8) 0.52694(13) 0.0276(5) Uani 1 1 d . . . . .
C60 C 0.67788(10) 0.61067(10) 0.51170(14) 0.0318(5) Uani 1 1 d . . . . .
H60A H 0.675749 0.576440 0.519297 0.048 Uiso 1 1 calc R U . . .
H60B H 0.685732 0.616662 0.464517 0.048 Uiso 1 1 calc R U . . .
H60C H 0.705501 0.624145 0.544187 0.048 Uiso 1 1 calc R U . . .
C61 C 0.55367(10) 0.93410(9) 0.47034(13) 0.0293(5) Uani 1 1 d . . . . .
H61A H 0.540216 0.959903 0.497860 0.035 Uiso 1 1 calc R U . . .
H61B H 0.562496 0.906852 0.501306 0.035 Uiso 1 1 calc R U . . .
C62 C 0.60361(10) 0.95137(10) 0.43925(15) 0.0345(6) Uani 1 1 d . . . . .
H62A H 0.629420 0.962672 0.476788 0.041 Uiso 1 1 calc R U . . .
H62B H 0.619234 0.924468 0.416245 0.041 Uiso 1 1 calc R U . . .
C63 C 0.59097(11) 0.99215(10) 0.38626(15) 0.0373(6) Uani 1 1 d . . . . .
H63A H 0.580967 1.020894 0.410750 0.045 Uiso 1 1 calc R U . . .
H63B H 0.622503 0.999706 0.363704 0.045 Uiso 1 1 calc R U . . .
C64 C 0.54603(11) 0.97831(10) 0.33054(14) 0.0359(6) Uani 1 1 d . . . . .
H64A H 0.557724 0.952200 0.302050 0.043 Uiso 1 1 calc R U . . .
H64B H 0.537235 1.005798 0.300034 0.043 Uiso 1 1 calc R U . . .
C65 C 0.49639(10) 0.96228(9) 0.36377(14) 0.0309(5) Uani 1 1 d . . . . .
H65A H 0.483494 0.988663 0.390707 0.037 Uiso 1 1 calc R U . . .
H65B H 0.468519 0.953329 0.327326 0.037 Uiso 1 1 calc R U . . .
C66 C 0.51069(9) 0.91901(9) 0.41179(13) 0.0260(5) Uani 1 1 d . . . . .
H66 H 0.525963 0.894042 0.383660 0.031 Uiso 1 1 calc R U . . .
C67 C 0.46411(9) 0.89687(8) 0.44297(12) 0.0251(5) Uani 1 1 d . . . . .
C68 C 0.41688(9) 0.91918(9) 0.45043(13) 0.0262(5) Uani 1 1 d . . . . .
H68 H 0.411211 0.950698 0.434386 0.031 Uiso 1 1 calc R U . . .
C69 C 0.37640(10) 0.89482(9) 0.48237(13) 0.0290(5) Uani 1 1 d . . . . .
C70 C 0.38477(10) 0.84799(9) 0.50497(13) 0.0296(5) Uani 1 1 d . . . . .
H70 H 0.358206 0.832135 0.526034 0.035 Uiso 1 1 calc R U . . .
C71 C 0.43283(10) 0.82316(9) 0.49704(13) 0.0276(5) Uani 1 1 d . . . . .
C72 C 0.32508(11) 0.92036(10) 0.49035(16) 0.0366(6) Uani 1 1 d . . . . .
H72A H 0.326413 0.952527 0.471753 0.055 Uiso 1 1 calc R U . . .
H72B H 0.296237 0.902953 0.465197 0.055 Uiso 1 1 calc R U . . .
H72C H 0.319770 0.921936 0.539190 0.055 Uiso 1 1 calc R U . . .
C73 C 0.73387(10) 0.83408(9) 0.61823(13) 0.0300(5) Uani 1 1 d . . . . .
H73A H 0.747103 0.860213 0.649086 0.036 Uiso 1 1 calc R U . . .
H73B H 0.718443 0.809817 0.646502 0.036 Uiso 1 1 calc R U . . .
C74 C 0.78015(11) 0.81172(10) 0.58398(15) 0.0362(6) Uani 1 1 d . . . . .
H74A H 0.798304 0.836875 0.560523 0.043 Uiso 1 1 calc R U . . .
H74B H 0.805350 0.797724 0.620101 0.043 Uiso 1 1 calc R U . . .
C75 C 0.76105(11) 0.77267(10) 0.53084(16) 0.0373(6) Uani 1 1 d . . . . .
H75A H 0.790833 0.761117 0.507552 0.045 Uiso 1 1 calc R U . . .
H75B H 0.746958 0.745566 0.555147 0.045 Uiso 1 1 calc R U . . .
C76 C 0.71821(10) 0.79228(10) 0.47625(14) 0.0336(6) Uani 1 1 d . . . . .
H76A H 0.705344 0.766406 0.444701 0.040 Uiso 1 1 calc R U . . .
H76B H 0.733354 0.817122 0.448677 0.040 Uiso 1 1 calc R U . . .
C77 C 0.67167(10) 0.81356(9) 0.51107(14) 0.0310(5) Uani 1 1 d . . . . .
H77A H 0.645513 0.826579 0.475279 0.037 Uiso 1 1 calc R U . . .
H77B H 0.654799 0.788199 0.535776 0.037 Uiso 1 1 calc R U . . .
C78 C 0.69084(9) 0.85367(8) 0.56283(13) 0.0254(5) Uani 1 1 d . . . . .
H78 H 0.706659 0.879353 0.536567 0.030 Uiso 1 1 calc R U . . .
C79 C 0.64649(10) 0.87547(8) 0.59898(12) 0.0254(5) Uani 1 1 d . . . . .
C80 C 0.60045(10) 0.85226(9) 0.61032(12) 0.0261(5) Uani 1 1 d . . . . .
H80 H 0.594816 0.820733 0.594310 0.031 Uiso 1 1 calc R U . . .
C81 C 0.56138(10) 0.87524(9) 0.64582(13) 0.0269(5) Uani 1 1 d . . . . .
C82 C 0.56948(10) 0.92220(9) 0.66845(13) 0.0275(5) Uani 1 1 d . . . . .
H82 H 0.543552 0.937434 0.691509 0.033 Uiso 1 1 calc R U . . .
C83 C 0.61628(10) 0.94787(8) 0.65751(13) 0.0277(5) Uani 1 1 d . . . . .
C84 C 0.51084(10) 0.84910(10) 0.65707(15) 0.0337(6) Uani 1 1 d . . . . .
H84A H 0.511848 0.816983 0.638202 0.051 Uiso 1 1 calc R U . . .
H84B H 0.507384 0.847359 0.706450 0.051 Uiso 1 1 calc R U . . .
H84C H 0.481049 0.866264 0.633747 0.051 Uiso 1 1 calc R U . . .
C85 C 0.10857(11) 0.93362(10) 0.67847(14) 0.0346(6) Uani 1 1 d . . . . .
H85A H 0.126794 0.957728 0.653105 0.042 Uiso 1 1 calc R U . . .
H85B H 0.099872 0.906511 0.647193 0.042 Uiso 1 1 calc R U . . .
C86 C 0.05745(11) 0.95529(11) 0.70111(16) 0.0417(7) Uani 1 1 d . . . . .
H86A H 0.035837 0.967700 0.660139 0.050 Uiso 1 1 calc R U . . .
H86B H 0.037364 0.930136 0.721735 0.050 Uiso 1 1 calc R U . . .
C87 C 0.06912(12) 0.99605(10) 0.75428(16) 0.0410(7) Uani 1 1 d . . . . .
H87A H 0.085097 1.023030 0.731877 0.049 Uiso 1 1 calc R U . . .
H87B H 0.036121 1.007172 0.770297 0.049 Uiso 1 1 calc R U . . .
C88 C 0.10659(11) 0.97900(10) 0.81704(15) 0.0354(6) Uani 1 1 d . . . . .
H88A H 0.089089 0.954342 0.842315 0.042 Uiso 1 1 calc R U . . .
H88B H 0.115011 1.005938 0.848718 0.042 Uiso 1 1 calc R U . . .
C89 C 0.15806(10) 0.95836(10) 0.79358(14) 0.0332(6) Uani 1 1 d . . . . .
H89A H 0.176755 0.983451 0.770730 0.040 Uiso 1 1 calc R U . . .
H89B H 0.180936 0.947171 0.834234 0.040 Uiso 1 1 calc R U . . .
C90 C 0.14530(10) 0.91645(9) 0.74285(13) 0.0281(5) Uani 1 1 d . . . . .
H90 H 0.125946 0.892060 0.767160 0.034 Uiso 1 1 calc R U . . .
C91 C 0.19455(10) 0.89256(9) 0.72044(13) 0.0272(5) Uani 1 1 d . . . . .
C92 C 0.24354(10) 0.91329(9) 0.72178(13) 0.0290(5) Uani 1 1 d . . . . .
H92 H 0.248508 0.944800 0.738175 0.035 Uiso 1 1 calc R U . . .
C93 C 0.28701(10) 0.88779(9) 0.69870(13) 0.0298(5) Uani 1 1 d . . . . .
C94 C 0.27908(10) 0.84142(9) 0.67420(13) 0.0299(5) Uani 1 1 d . . . . .
H94 H 0.307317 0.824910 0.657857 0.036 Uiso 1 1 calc R U . . .
C95 C 0.22943(10) 0.81800(9) 0.67303(14) 0.0309(5) Uani 1 1 d . . . . .
C96 C 0.34120(11) 0.91034(11) 0.70416(16) 0.0396(6) Uani 1 1 d . . . . .
H96A H 0.339393 0.942629 0.722166 0.059 Uiso 1 1 calc R U . . .
H96B H 0.365299 0.891489 0.735307 0.059 Uiso 1 1 calc R U . . .
H96C H 0.353589 0.911318 0.658516 0.059 Uiso 1 1 calc R U . . .
C97 C 0.22684(10) 0.59033(10) 0.62359(14) 0.0319(5) Uani 1 1 d . . . . .
H97A H 0.211531 0.567301 0.653916 0.038 Uiso 1 1 calc R U . . .
H97B H 0.235316 0.619556 0.650490 0.038 Uiso 1 1 calc R U . . .
C98 C 0.27801(11) 0.56910(11) 0.59964(14) 0.0363(6) Uani 1 1 d . . . . .
H98A H 0.295856 0.593679 0.574661 0.044 Uiso 1 1 calc R U . . .
H98B H 0.301680 0.559536 0.640498 0.044 Uiso 1 1 calc R U . . .
C99 C 0.26626(11) 0.52535(10) 0.55189(15) 0.0357(6) Uani 1 1 d . . . . .
H99A H 0.298838 0.514621 0.534276 0.043 Uiso 1 1 calc R U . . .
H99B H 0.253050 0.499073 0.578749 0.043 Uiso 1 1 calc R U . . .
C100 C 0.22529(10) 0.53759(10) 0.49028(14) 0.0319(5) Uani 1 1 d . . . . .
H10A H 0.217296 0.508768 0.462243 0.038 Uiso 1 1 calc R U . . .
H10B H 0.240009 0.561516 0.460765 0.038 Uiso 1 1 calc R U . . .
C101 C 0.17410(10) 0.55721(9) 0.51511(14) 0.0305(5) Uani 1 1 d . . . . .
H10C H 0.157936 0.532592 0.542008 0.037 Uiso 1 1 calc R U . . .
H10D H 0.149201 0.565414 0.474797 0.037 Uiso 1 1 calc R U . . .
C102 C 0.18607(10) 0.60214(9) 0.56068(13) 0.0264(5) Uani 1 1 d . . . . .
H102 H 0.201810 0.626505 0.532011 0.032 Uiso 1 1 calc R U . . .
C103 C 0.13665(10) 0.62393(8) 0.58625(12) 0.0260(5) Uani 1 1 d . . . . .
C104 C 0.09122(10) 0.59916(9) 0.59541(12) 0.0265(5) Uani 1 1 d . . . . .
H104 H 0.088982 0.566349 0.584827 0.032 Uiso 1 1 calc R U . . .
C105 C 0.04770(10) 0.62270(9) 0.62069(13) 0.0290(5) Uani 1 1 d . . . . .
C106 C 0.05130(10) 0.67123(9) 0.63605(13) 0.0292(5) Uani 1 1 d . . . . .
H106 H 0.022612 0.686578 0.653117 0.035 Uiso 1 1 calc R U . . .
C107 C 0.09730(10) 0.69859(9) 0.62673(14) 0.0307(5) Uani 1 1 d . . . . .
C108 C -0.00269(11) 0.59523(10) 0.62774(16) 0.0365(6) Uani 1 1 d . . . . .
H10E H 0.001894 0.562045 0.614936 0.055 Uiso 1 1 calc R U . . .
H10F H -0.010897 0.596891 0.675486 0.055 Uiso 1 1 calc R U . . .
H10G H -0.031255 0.609200 0.597310 0.055 Uiso 1 1 calc R U . . .
C109 C -0.04637(11) 0.34660(11) 0.56796(14) 0.0360(6) Uani 1 1 d . . . . .
H10H H -0.056301 0.374656 0.539102 0.043 Uiso 1 1 calc R U . . .
H10I H -0.032512 0.322271 0.538289 0.043 Uiso 1 1 calc R U . . .
C110 C -0.09547(12) 0.32671(12) 0.59811(16) 0.0435(7) Uani 1 1 d . . . . .
H11A H -0.120773 0.315255 0.560096 0.052 Uiso 1 1 calc R U . . .
H11B H -0.112262 0.352385 0.622293 0.052 Uiso 1 1 calc R U . . .
C111 C -0.08073(15) 0.28526(11) 0.64925(18) 0.0529(8) Uani 1 1 d . . . . .
H11C H -0.111854 0.275654 0.671320 0.064 Uiso 1 1 calc R U . . .
H11D H -0.069199 0.257670 0.623510 0.064 Uiso 1 1 calc R U . . .
C112 C -0.03654(14) 0.29978(12) 0.70585(16) 0.0505(8) Uani 1 1 d . . . . .
H11E H -0.049438 0.324988 0.734920 0.061 Uiso 1 1 calc R U . . .
H11F H -0.026842 0.272125 0.735648 0.061 Uiso 1 1 calc R U . . .
C113 C 0.01242(13) 0.31799(12) 0.67391(16) 0.0469(8) Uani 1 1 d . . . . .
H11G H 0.039546 0.327579 0.710958 0.056 Uiso 1 1 calc R U . . .
H11H H 0.026769 0.292367 0.646923 0.056 Uiso 1 1 calc R U . . .
C114 C -0.00295(10) 0.36093(10) 0.62653(14) 0.0321(6) Uani 1 1 d . . . . .
H114 H -0.017539 0.386022 0.655112 0.039 Uiso 1 1 calc R U . . .
C115 C 0.04294(10) 0.38258(10) 0.59338(14) 0.0334(6) Uani 1 1 d . . . . .
C116 C 0.08923(11) 0.35927(11) 0.58302(15) 0.0378(6) Uani 1 1 d . . . . .
H116 H 0.095211 0.328127 0.600451 0.045 Uiso 1 1 calc R U . . .
C117 C 0.12784(11) 0.38173(12) 0.54641(16) 0.0424(7) Uani 1 1 d . . . . .
C118 C 0.11936(11) 0.42784(11) 0.52163(17) 0.0430(7) Uani 1 1 d . . . . .
H118 H 0.144941 0.442453 0.497245 0.052 Uiso 1 1 calc R U . . .
C119 C 0.07251(11) 0.45396(11) 0.53216(17) 0.0419(7) Uani 1 1 d . . . . .
C120 C 0.17815(13) 0.35501(16) 0.53509(18) 0.0587(10) Uani 1 1 d . . . . .
H12D H 0.177430 0.323416 0.555769 0.088 Uiso 1 1 calc R U . . .
H12E H 0.180781 0.351961 0.485643 0.088 Uiso 1 1 calc R U . . .
H12F H 0.208262 0.372621 0.556662 0.088 Uiso 1 1 calc R U . . .
C121 C 0.15127(10) 0.42417(9) 0.81818(13) 0.0279(5) Uani 1 1 d . . . . .
H12G H 0.153537 0.390566 0.832729 0.033 Uiso 1 1 calc R U . . .
H12H H 0.180521 0.441561 0.843681 0.033 Uiso 1 1 calc R U . . .
C122 C 0.09856(10) 0.44562(9) 0.83539(14) 0.0300(5) Uani 1 1 d . . . . .
H12I H 0.069416 0.426961 0.811955 0.036 Uiso 1 1 calc R U . . .
H12J H 0.096495 0.443595 0.885602 0.036 Uiso 1 1 calc R U . . .
C123 C 0.09313(11) 0.49828(9) 0.81210(14) 0.0331(6) Uani 1 1 d . . . . .
H12K H 0.119610 0.517624 0.839812 0.040 Uiso 1 1 calc R U . . .
H12L H 0.058323 0.510202 0.820501 0.040 Uiso 1 1 calc R U . . .
C124 C 0.10026(11) 0.50387(9) 0.73425(15) 0.0345(6) Uani 1 1 d . . . . .
H12M H 0.099925 0.537945 0.722194 0.041 Uiso 1 1 calc R U . . .
H12N H 0.070790 0.488441 0.706222 0.041 Uiso 1 1 calc R U . . .
C125 C 0.15256(11) 0.48121(9) 0.71694(14) 0.0307(5) Uani 1 1 d . . . . .
H12O H 0.182229 0.498687 0.741326 0.037 Uiso 1 1 calc R U . . .
H12P H 0.155095 0.483721 0.666877 0.037 Uiso 1 1 calc R U . . .
C126 C 0.15550(9) 0.42767(8) 0.73906(13) 0.0253(5) Uani 1 1 d . . . . .
H126 H 0.124598 0.411143 0.714684 0.030 Uiso 1 1 calc R U . . .
C127 C 0.20451(10) 0.40264(9) 0.71953(12) 0.0265(5) Uani 1 1 d . . . . .
C128 C 0.25071(10) 0.42458(9) 0.70482(13) 0.0298(5) Uani 1 1 d . . . . .
H128 H 0.253299 0.458120 0.706282 0.036 Uiso 1 1 calc R U . . .
C129 C 0.29441(10) 0.39688(10) 0.68748(13) 0.0316(5) Uani 1 1 d . . . . .
C130 C 0.29060(10) 0.34742(10) 0.68549(14) 0.0327(6) Uani 1 1 d . . . . .
H130 H 0.319498 0.329409 0.674066 0.039 Uiso 1 1 calc R U . . .
C131 C 0.24370(10) 0.32286(9) 0.70039(13) 0.0298(5) Uani 1 1 d . . . . .
C132 C 0.34383(11) 0.42257(11) 0.67006(16) 0.0396(6) Uani 1 1 d . . . . .
H13C H 0.339118 0.456850 0.674310 0.059 Uiso 1 1 calc R U . . .
H13D H 0.373567 0.412327 0.701956 0.059 Uiso 1 1 calc R U . . .
H13E H 0.350286 0.414888 0.622826 0.059 Uiso 1 1 calc R U . . .
C133 C 0.21256(10) 0.08198(10) 0.64925(14) 0.0316(5) Uani 1 1 d . . . . .
H13F H 0.226783 0.106387 0.682478 0.038 Uiso 1 1 calc R U . . .
H13G H 0.193695 0.058329 0.674596 0.038 Uiso 1 1 calc R U . . .
C134 C 0.25819(11) 0.05719(11) 0.61737(16) 0.0406(7) Uani 1 1 d . . . . .
H13H H 0.280654 0.040662 0.654070 0.049 Uiso 1 1 calc R U . . .
H13I H 0.279587 0.081369 0.596805 0.049 Uiso 1 1 calc R U . . .
C135 C 0.23740(12) 0.02073(10) 0.56091(16) 0.0390(6) Uani 1 1 d . . . . .
H13J H 0.267028 0.007330 0.539107 0.047 Uiso 1 1 calc R U . . .
H13K H 0.219752 -0.005613 0.582542 0.047 Uiso 1 1 calc R U . . .
C136 C 0.19863(11) 0.04446(9) 0.50506(14) 0.0324(6) Uani 1 1 d . . . . .
H13L H 0.184668 0.020244 0.471371 0.039 Uiso 1 1 calc R U . . .
H13M H 0.217233 0.068564 0.480160 0.039 Uiso 1 1 calc R U . . .
C137 C 0.15280(10) 0.06843(9) 0.53745(14) 0.0312(5) Uani 1 1 d . . . . .
H13N H 0.132432 0.044020 0.559211 0.037 Uiso 1 1 calc R U . . .
H13O H 0.129401 0.084188 0.500937 0.037 Uiso 1 1 calc R U . . .
C138 C 0.17379(10) 0.10574(9) 0.59253(13) 0.0263(5) Uani 1 1 d . . . . .
H138 H 0.193616 0.130114 0.568842 0.032 Uiso 1 1 calc R U . . .
C139 C 0.13020(10) 0.13153(8) 0.62545(13) 0.0263(5) Uani 1 1 d . . . . .
C140 C 0.08075(10) 0.11290(9) 0.63203(13) 0.0293(5) Uani 1 1 d . . . . .
H140 H 0.071925 0.082417 0.613864 0.035 Uiso 1 1 calc R U . . .
C141 C 0.04293(10) 0.13922(9) 0.66595(14) 0.0308(5) Uani 1 1 d . . . . .
C142 C 0.05600(11) 0.18397(10) 0.69248(16) 0.0357(6) Uani 1 1 d . . . . .
H142 H 0.031092 0.201232 0.714770 0.043 Uiso 1 1 calc R U . . .
C143 C 0.10647(11) 0.20482(9) 0.68696(17) 0.0378(6) Uani 1 1 d . . . . .
C144 C -0.01108(11) 0.11790(11) 0.67160(16) 0.0396(6) Uani 1 1 d . . . . .
H14C H -0.013148 0.086455 0.650234 0.059 Uiso 1 1 calc R U . . .
H14D H -0.016782 0.115113 0.720199 0.059 Uiso 1 1 calc R U . . .
H14E H -0.037789 0.138519 0.647968 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.371(3) . ?
N1 O1 1.386(3) . ?
N1 C11 1.387(3) . ?
N2 C19 1.367(3) . ?
N2 O3 1.384(3) . ?
N2 C23 1.391(3) . ?
N3 C31 1.370(3) . ?
N3 O5 1.383(3) . ?
N3 C35 1.385(3) . ?
N4 C43 1.365(3) . ?
N4 O7 1.383(3) . ?
N4 C47 1.389(3) . ?
N5 C55 1.366(3) . ?
N5 O9 1.383(3) . ?
N5 C59 1.387(3) . ?
N6 C67 1.369(3) . ?
N6 C71 1.381(3) . ?
N6 O11 1.384(3) . ?
N7 C79 1.367(3) . ?
N7 C83 1.386(3) . ?
N7 O13 1.388(3) . ?
N8 C91 1.363(3) . ?
N8 O15 1.381(3) . ?
N8 C95 1.395(3) . ?
N9 C103 1.368(3) . ?
N9 O17 1.383(3) . ?
N9 C107 1.385(3) . ?
N10 C115 1.367(4) . ?
N10 O19 1.385(3) . ?
N10 C119 1.386(4) . ?
N11 C127 1.367(3) . ?
N11 O21 1.380(3) . ?
N11 C131 1.388(3) . ?
N12 C139 1.363(3) . ?
N12 C143 1.385(3) . ?
N12 O23 1.388(3) . ?
O1 H1 0.8200 . ?
O2 C11 1.248(3) . ?
O3 H3 0.8200 . ?
O4 C23 1.253(3) . ?
O5 H5 0.8200 . ?
O6 C35 1.257(3) . ?
O7 H7 0.8200 . ?
O8 C47 1.245(3) . ?
O9 H9 0.8200 . ?
O10 C59 1.257(3) . ?
O11 H11 0.8200 . ?
O12 C71 1.252(3) . ?
O13 H13 0.8200 . ?
O14 C83 1.248(3) . ?
O15 H15 0.8200 . ?
O16 C95 1.248(3) . ?
O17 H17 0.8200 . ?
O18 C107 1.251(3) . ?
O19 H19 0.8200 . ?
O20 C119 1.254(4) . ?
O21 H21 0.8200 . ?
O22 C131 1.252(3) . ?
O23 H23 0.8200 . ?
O24 C143 1.249(3) . ?
C1 C6 1.520(4) . ?
C1 C2 1.528(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.524(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.513(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.536(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.538(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.499(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.366(3) . ?
C8 C9 1.412(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(4) . ?
C9 C12 1.504(4) . ?
C10 C11 1.419(4) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.529(4) . ?
C13 C18 1.530(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.528(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.520(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.535(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.527(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.509(3) . ?
C18 H18 0.9800 . ?
C19 C20 1.366(3) . ?
C20 C21 1.408(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(4) . ?
C21 C24 1.502(4) . ?
C22 C23 1.415(4) . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.527(3) . ?
C25 C30 1.536(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.528(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.521(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.531(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.533(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.497(3) . ?
C30 H30 0.9800 . ?
C31 C32 1.380(4) . ?
C32 C33 1.411(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.371(4) . ?
C33 C36 1.503(4) . ?
C34 C35 1.415(4) . ?
C34 H34 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.530(4) . ?
C37 C42 1.533(4) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.524(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.520(4) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.532(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.525(3) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.506(3) . ?
C42 H42 0.9800 . ?
C43 C44 1.369(3) . ?
C44 C45 1.415(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.378(4) . ?
C45 C48 1.498(4) . ?
C46 C47 1.417(4) . ?
C46 H46 0.9300 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.525(4) . ?
C49 C54 1.539(3) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.525(4) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 C52 1.520(4) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 C53 1.529(4) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C53 C54 1.532(3) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 C55 1.501(3) . ?
C54 H54 0.9800 . ?
C55 C56 1.372(3) . ?
C56 C57 1.411(3) . ?
C56 H56 0.9300 . ?
C57 C58 1.375(3) . ?
C57 C60 1.508(3) . ?
C58 C59 1.416(3) . ?
C58 H58 0.9300 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 C62 1.530(4) . ?
C61 C66 1.534(3) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C62 C63 1.528(4) . ?
C62 H62A 0.9700 . ?
C62 H62B 0.9700 . ?
C63 C64 1.523(4) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C64 C65 1.533(4) . ?
C64 H64A 0.9700 . ?
C64 H64B 0.9700 . ?
C65 C66 1.529(3) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C66 C67 1.507(3) . ?
C66 H66 0.9800 . ?
C67 C68 1.366(3) . ?
C68 C69 1.418(4) . ?
C68 H68 0.9300 . ?
C69 C70 1.375(4) . ?
C69 C72 1.500(4) . ?
C70 C71 1.419(4) . ?
C70 H70 0.9300 . ?
C72 H72A 0.9600 . ?
C72 H72B 0.9600 . ?
C72 H72C 0.9600 . ?
C73 C74 1.532(4) . ?
C73 C78 1.536(3) . ?
C73 H73A 0.9700 . ?
C73 H73B 0.9700 . ?
C74 C75 1.527(4) . ?
C74 H74A 0.9700 . ?
C74 H74B 0.9700 . ?
C75 C76 1.523(4) . ?
C75 H75A 0.9700 . ?
C75 H75B 0.9700 . ?
C76 C77 1.532(4) . ?
C76 H76A 0.9700 . ?
C76 H76B 0.9700 . ?
C77 C78 1.531(3) . ?
C77 H77A 0.9700 . ?
C77 H77B 0.9700 . ?
C78 C79 1.506(3) . ?
C78 H78 0.9800 . ?
C79 C80 1.368(3) . ?
C80 C81 1.410(4) . ?
C80 H80 0.9300 . ?
C81 C82 1.377(3) . ?
C81 C84 1.505(3) . ?
C82 C83 1.415(3) . ?
C82 H82 0.9300 . ?
C84 H84A 0.9600 . ?
C84 H84B 0.9600 . ?
C84 H84C 0.9600 . ?
C85 C86 1.530(4) . ?
C85 C90 1.538(3) . ?
C85 H85A 0.9700 . ?
C85 H85B 0.9700 . ?
C86 C87 1.527(4) . ?
C86 H86A 0.9700 . ?
C86 H86B 0.9700 . ?
C87 C88 1.524(4) . ?
C87 H87A 0.9700 . ?
C87 H87B 0.9700 . ?
C88 C89 1.533(4) . ?
C88 H88A 0.9700 . ?
C88 H88B 0.9700 . ?
C89 C90 1.524(3) . ?
C89 H89A 0.9700 . ?
C89 H89B 0.9700 . ?
C90 C91 1.513(3) . ?
C90 H90 0.9800 . ?
C91 C92 1.364(4) . ?
C92 C93 1.417(4) . ?
C92 H92 0.9300 . ?
C93 C94 1.373(4) . ?
C93 C96 1.500(4) . ?
C94 C95 1.412(4) . ?
C94 H94 0.9300 . ?
C96 H96A 0.9600 . ?
C96 H96B 0.9600 . ?
C96 H96C 0.9600 . ?
C97 C102 1.535(3) . ?
C97 C98 1.536(4) . ?
C97 H97A 0.9700 . ?
C97 H97B 0.9700 . ?
C98 C99 1.526(4) . ?
C98 H98A 0.9700 . ?
C98 H98B 0.9700 . ?
C99 C100 1.524(4) . ?
C99 H99A 0.9700 . ?
C99 H99B 0.9700 . ?
C100 C101 1.526(4) . ?
C100 H10A 0.9700 . ?
C100 H10B 0.9700 . ?
C101 C102 1.530(3) . ?
C101 H10C 0.9700 . ?
C101 H10D 0.9700 . ?
C102 C103 1.516(3) . ?
C102 H102 0.9800 . ?
C103 C104 1.366(3) . ?
C104 C105 1.409(4) . ?
C104 H104 0.9300 . ?
C105 C106 1.375(4) . ?
C105 C108 1.503(4) . ?
C106 C107 1.416(4) . ?
C106 H106 0.9300 . ?
C108 H10E 0.9600 . ?
C108 H10F 0.9600 . ?
C108 H10G 0.9600 . ?
C109 C110 1.528(4) . ?
C109 C114 1.536(3) . ?
C109 H10H 0.9700 . ?
C109 H10I 0.9700 . ?
C110 C111 1.528(5) . ?
C110 H11A 0.9700 . ?
C110 H11B 0.9700 . ?
C111 C112 1.526(5) . ?
C111 H11C 0.9700 . ?
C111 H11D 0.9700 . ?
C112 C113 1.525(5) . ?
C112 H11E 0.9700 . ?
C112 H11F 0.9700 . ?
C113 C114 1.520(4) . ?
C113 H11G 0.9700 . ?
C113 H11H 0.9700 . ?
C114 C115 1.506(4) . ?
C114 H114 0.9800 . ?
C115 C116 1.370(4) . ?
C116 C117 1.407(4) . ?
C116 H116 0.9300 . ?
C117 C118 1.369(5) . ?
C117 C120 1.508(4) . ?
C118 C119 1.421(4) . ?
C118 H118 0.9300 . ?
C120 H12D 0.9600 . ?
C120 H12E 0.9600 . ?
C120 H12F 0.9600 . ?
C121 C122 1.528(3) . ?
C121 C126 1.533(3) . ?
C121 H12G 0.9700 . ?
C121 H12H 0.9700 . ?
C122 C123 1.525(3) . ?
C122 H12I 0.9700 . ?
C122 H12J 0.9700 . ?
C123 C124 1.528(4) . ?
C123 H12K 0.9700 . ?
C123 H12L 0.9700 . ?
C124 C125 1.532(4) . ?
C124 H12M 0.9700 . ?
C124 H12N 0.9700 . ?
C125 C126 1.539(3) . ?
C125 H12O 0.9700 . ?
C125 H12P 0.9700 . ?
C126 C127 1.502(3) . ?
C126 H126 0.9800 . ?
C127 C128 1.373(4) . ?
C128 C129 1.414(4) . ?
C128 H128 0.9300 . ?
C129 C130 1.371(4) . ?
C129 C132 1.506(4) . ?
C130 C131 1.423(4) . ?
C130 H130 0.9300 . ?
C132 H13C 0.9600 . ?
C132 H13D 0.9600 . ?
C132 H13E 0.9600 . ?
C133 C134 1.525(4) . ?
C133 C138 1.532(3) . ?
C133 H13F 0.9700 . ?
C133 H13G 0.9700 . ?
C134 C135 1.530(4) . ?
C134 H13H 0.9700 . ?
C134 H13I 0.9700 . ?
C135 C136 1.521(4) . ?
C135 H13J 0.9700 . ?
C135 H13K 0.9700 . ?
C136 C137 1.524(4) . ?
C136 H13L 0.9700 . ?
C136 H13M 0.9700 . ?
C137 C138 1.529(3) . ?
C137 H13N 0.9700 . ?
C137 H13O 0.9700 . ?
C138 C139 1.507(3) . ?
C138 H138 0.9800 . ?
C139 C140 1.372(3) . ?
C140 C141 1.414(4) . ?
C140 H140 0.9300 . ?
C141 C142 1.365(4) . ?
C141 C144 1.503(4) . ?
C142 C143 1.416(4) . ?
C142 H142 0.9300 . ?
C144 H14C 0.9600 . ?
C144 H14D 0.9600 . ?
C144 H14E 0.9600 . ?

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
C7 N1 O1 116.63(19) . . ?
C7 N1 C11 126.7(2) . . ?
O1 N1 C11 116.67(18) . . ?
C19 N2 O3 117.00(19) . . ?
C19 N2 C23 126.5(2) . . ?
O3 N2 C23 116.43(19) . . ?
C31 N3 O5 116.74(19) . . ?
C31 N3 C35 126.4(2) . . ?
O5 N3 C35 116.81(19) . . ?
C43 N4 O7 116.4(2) . . ?
C43 N4 C47 126.6(2) . . ?
O7 N4 C47 116.9(2) . . ?
C55 N5 O9 116.87(19) . . ?
C55 N5 C59 126.4(2) . . ?
O9 N5 C59 116.77(18) . . ?
C67 N6 C71 126.4(2) . . ?
C67 N6 O11 116.79(19) . . ?
C71 N6 O11 116.71(19) . . ?
C79 N7 C83 126.3(2) . . ?
C79 N7 O13 117.6(2) . . ?
C83 N7 O13 116.15(18) . . ?
C91 N8 O15 117.6(2) . . ?
C91 N8 C95 125.8(2) . . ?
O15 N8 C95 116.58(19) . . ?
C103 N9 O17 116.7(2) . . ?
C103 N9 C107 126.0(2) . . ?
O17 N9 C107 117.2(2) . . ?
C115 N10 O19 116.7(2) . . ?
C115 N10 C119 126.1(2) . . ?
O19 N10 C119 117.2(2) . . ?
C127 N11 O21 116.61(19) . . ?
C127 N11 C131 126.7(2) . . ?
O21 N11 C131 116.67(19) . . ?
C139 N12 C143 126.2(2) . . ?
C139 N12 O23 117.0(2) . . ?
C143 N12 O23 116.8(2) . . ?
N1 O1 H1 109.5 . . ?
N2 O3 H3 109.5 . . ?
N3 O5 H5 109.5 . . ?
N4 O7 H7 109.5 . . ?
N5 O9 H9 109.5 . . ?
N6 O11 H11 109.5 . . ?
N7 O13 H13 109.5 . . ?
N8 O15 H15 109.5 . . ?
N9 O17 H17 109.5 . . ?
N10 O19 H19 109.5 . . ?
N11 O21 H21 109.5 . . ?
N12 O23 H23 109.5 . . ?
C6 C1 C2 109.9(2) . . ?
C6 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
C6 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C1 111.3(2) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 111.8(2) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 112.1(3) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 109.1(2) . . ?
C4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C7 C6 C1 111.0(2) . . ?
C7 C6 C5 113.2(2) . . ?
C1 C6 C5 109.4(2) . . ?
C7 C6 H6 107.7 . . ?
C1 C6 H6 107.7 . . ?
C5 C6 H6 107.7 . . ?
C8 C7 N1 116.6(2) . . ?
C8 C7 C6 126.6(2) . . ?
N1 C7 C6 116.7(2) . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 C12 120.2(2) . . ?
C8 C9 C12 120.3(2) . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
O2 C11 N1 117.9(2) . . ?
O2 C11 C10 127.8(2) . . ?
N1 C11 C10 114.3(2) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 111.1(2) . . ?
C14 C13 H13A 109.4 . . ?
C18 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C18 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 111.9(2) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 111.3(2) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 110.9(2) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 109.8(2) . . ?
C18 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C17 113.5(2) . . ?
C19 C18 C13 110.58(19) . . ?
C17 C18 C13 110.2(2) . . ?
C19 C18 H18 107.4 . . ?
C17 C18 H18 107.4 . . ?
C13 C18 H18 107.4 . . ?
C20 C19 N2 117.0(2) . . ?
C20 C19 C18 125.7(2) . . ?
N2 C19 C18 117.3(2) . . ?
C19 C20 C21 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 119.4(2) . . ?
C22 C21 C24 120.7(2) . . ?
C20 C21 C24 119.9(2) . . ?
C21 C22 C23 122.0(2) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
O4 C23 N2 118.2(2) . . ?
O4 C23 C22 127.8(2) . . ?
N2 C23 C22 114.0(2) . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 110.5(2) . . ?
C26 C25 H25A 109.6 . . ?
C30 C25 H25A 109.6 . . ?
C26 C25 H25B 109.6 . . ?
C30 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 C27 110.9(2) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.0 . . ?
C28 C27 C26 111.6(2) . . ?
C28 C27 H27A 109.3 . . ?
C26 C27 H27A 109.3 . . ?
C28 C27 H27B 109.3 . . ?
C26 C27 H27B 109.3 . . ?
H27A C27 H27B 108.0 . . ?
C27 C28 C29 111.5(2) . . ?
C27 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?
C28 C29 C30 110.2(2) . . ?
C28 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C31 C30 C29 113.3(2) . . ?
C31 C30 C25 110.44(19) . . ?
C29 C30 C25 109.5(2) . . ?
C31 C30 H30 107.8 . . ?
C29 C30 H30 107.8 . . ?
C25 C30 H30 107.8 . . ?
N3 C31 C32 116.5(2) . . ?
N3 C31 C30 117.4(2) . . ?
C32 C31 C30 126.0(2) . . ?
C31 C32 C33 121.0(2) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C34 C33 C32 119.5(2) . . ?
C34 C33 C36 120.5(3) . . ?
C32 C33 C36 120.0(3) . . ?
C33 C34 C35 121.8(2) . . ?
C33 C34 H34 119.1 . . ?
C35 C34 H34 119.1 . . ?
O6 C35 N3 118.3(2) . . ?
O6 C35 C34 127.0(2) . . ?
N3 C35 C34 114.7(2) . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C42 111.2(2) . . ?
C38 C37 H37A 109.4 . . ?
C42 C37 H37A 109.4 . . ?
C38 C37 H37B 109.4 . . ?
C42 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C39 C38 C37 111.5(2) . . ?
C39 C38 H38A 109.3 . . ?
C37 C38 H38A 109.3 . . ?
C39 C38 H38B 109.3 . . ?
C37 C38 H38B 109.3 . . ?
H38A C38 H38B 108.0 . . ?
C40 C39 C38 111.4(2) . . ?
C40 C39 H39A 109.3 . . ?
C38 C39 H39A 109.3 . . ?
C40 C39 H39B 109.3 . . ?
C38 C39 H39B 109.3 . . ?
H39A C39 H39B 108.0 . . ?
C39 C40 C41 111.6(2) . . ?
C39 C40 H40A 109.3 . . ?
C41 C40 H40A 109.3 . . ?
C39 C40 H40B 109.3 . . ?
C41 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
C42 C41 C40 109.7(2) . . ?
C42 C41 H41A 109.7 . . ?
C40 C41 H41A 109.7 . . ?
C42 C41 H41B 109.7 . . ?
C40 C41 H41B 109.7 . . ?
H41A C41 H41B 108.2 . . ?
C43 C42 C41 114.1(2) . . ?
C43 C42 C37 109.3(2) . . ?
C41 C42 C37 110.2(2) . . ?
C43 C42 H42 107.7 . . ?
C41 C42 H42 107.7 . . ?
C37 C42 H42 107.7 . . ?
N4 C43 C44 117.2(2) . . ?
N4 C43 C42 117.5(2) . . ?
C44 C43 C42 125.3(2) . . ?
C43 C44 C45 120.9(2) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C46 C45 C44 119.0(2) . . ?
C46 C45 C48 121.0(3) . . ?
C44 C45 C48 120.0(2) . . ?
C45 C46 C47 122.2(2) . . ?
C45 C46 H46 118.9 . . ?
C47 C46 H46 118.9 . . ?
O8 C47 N4 119.0(2) . . ?
O8 C47 C46 127.0(3) . . ?
N4 C47 C46 114.0(2) . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C50 C49 C54 109.3(2) . . ?
C50 C49 H49A 109.8 . . ?
C54 C49 H49A 109.8 . . ?
C50 C49 H49B 109.8 . . ?
C54 C49 H49B 109.8 . . ?
H49A C49 H49B 108.3 . . ?
C49 C50 C51 111.3(2) . . ?
C49 C50 H50A 109.4 . . ?
C51 C50 H50A 109.4 . . ?
C49 C50 H50B 109.4 . . ?
C51 C50 H50B 109.4 . . ?
H50A C50 H50B 108.0 . . ?
C52 C51 C50 110.8(2) . . ?
C52 C51 H51A 109.5 . . ?
C50 C51 H51A 109.5 . . ?
C52 C51 H51B 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 108.1 . . ?
C51 C52 C53 111.4(2) . . ?
C51 C52 H52A 109.4 . . ?
C53 C52 H52A 109.4 . . ?
C51 C52 H52B 109.4 . . ?
C53 C52 H52B 109.4 . . ?
H52A C52 H52B 108.0 . . ?
C52 C53 C54 110.1(2) . . ?
C52 C53 H53A 109.6 . . ?
C54 C53 H53A 109.6 . . ?
C52 C53 H53B 109.6 . . ?
C54 C53 H53B 109.6 . . ?
H53A C53 H53B 108.2 . . ?
C55 C54 C53 113.4(2) . . ?
C55 C54 C49 109.72(19) . . ?
C53 C54 C49 110.14(19) . . ?
C55 C54 H54 107.8 . . ?
C53 C54 H54 107.8 . . ?
C49 C54 H54 107.8 . . ?
N5 C55 C56 116.9(2) . . ?
N5 C55 C54 116.9(2) . . ?
C56 C55 C54 126.2(2) . . ?
C55 C56 C57 121.1(2) . . ?
C55 C56 H56 119.5 . . ?
C57 C56 H56 119.5 . . ?
C58 C57 C56 119.2(2) . . ?
C58 C57 C60 120.1(2) . . ?
C56 C57 C60 120.7(2) . . ?
C57 C58 C59 121.8(2) . . ?
C57 C58 H58 119.1 . . ?
C59 C58 H58 119.1 . . ?
O10 C59 N5 118.0(2) . . ?
O10 C59 C58 127.5(2) . . ?
N5 C59 C58 114.6(2) . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C62 C61 C66 110.6(2) . . ?
C62 C61 H61A 109.5 . . ?
C66 C61 H61A 109.5 . . ?
C62 C61 H61B 109.5 . . ?
C66 C61 H61B 109.5 . . ?
H61A C61 H61B 108.1 . . ?
C63 C62 C61 111.4(2) . . ?
C63 C62 H62A 109.3 . . ?
C61 C62 H62A 109.3 . . ?
C63 C62 H62B 109.3 . . ?
C61 C62 H62B 109.3 . . ?
H62A C62 H62B 108.0 . . ?
C64 C63 C62 111.6(2) . . ?
C64 C63 H63A 109.3 . . ?
C62 C63 H63A 109.3 . . ?
C64 C63 H63B 109.3 . . ?
C62 C63 H63B 109.3 . . ?
H63A C63 H63B 108.0 . . ?
C63 C64 C65 111.5(2) . . ?
C63 C64 H64A 109.3 . . ?
C65 C64 H64A 109.3 . . ?
C63 C64 H64B 109.3 . . ?
C65 C64 H64B 109.3 . . ?
H64A C64 H64B 108.0 . . ?
C66 C65 C64 108.9(2) . . ?
C66 C65 H65A 109.9 . . ?
C64 C65 H65A 109.9 . . ?
C66 C65 H65B 109.9 . . ?
C64 C65 H65B 109.9 . . ?
H65A C65 H65B 108.3 . . ?
C67 C66 C65 114.3(2) . . ?
C67 C66 C61 110.2(2) . . ?
C65 C66 C61 109.3(2) . . ?
C67 C66 H66 107.6 . . ?
C65 C66 H66 107.6 . . ?
C61 C66 H66 107.6 . . ?
C68 C67 N6 117.2(2) . . ?
C68 C67 C66 126.0(2) . . ?
N6 C67 C66 116.7(2) . . ?
C67 C68 C69 120.7(2) . . ?
C67 C68 H68 119.6 . . ?
C69 C68 H68 119.6 . . ?
C70 C69 C68 119.3(2) . . ?
C70 C69 C72 121.2(2) . . ?
C68 C69 C72 119.6(2) . . ?
C69 C70 C71 121.8(2) . . ?
C69 C70 H70 119.1 . . ?
C71 C70 H70 119.1 . . ?
O12 C71 N6 118.5(2) . . ?
O12 C71 C70 127.1(2) . . ?
N6 C71 C70 114.5(2) . . ?
C69 C72 H72A 109.5 . . ?
C69 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C69 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C74 C73 C78 111.4(2) . . ?
C74 C73 H73A 109.3 . . ?
C78 C73 H73A 109.3 . . ?
C74 C73 H73B 109.3 . . ?
C78 C73 H73B 109.3 . . ?
H73A C73 H73B 108.0 . . ?
C75 C74 C73 111.6(2) . . ?
C75 C74 H74A 109.3 . . ?
C73 C74 H74A 109.3 . . ?
C75 C74 H74B 109.3 . . ?
C73 C74 H74B 109.3 . . ?
H74A C74 H74B 108.0 . . ?
C76 C75 C74 110.9(2) . . ?
C76 C75 H75A 109.5 . . ?
C74 C75 H75A 109.5 . . ?
C76 C75 H75B 109.5 . . ?
C74 C75 H75B 109.5 . . ?
H75A C75 H75B 108.0 . . ?
C75 C76 C77 111.2(2) . . ?
C75 C76 H76A 109.4 . . ?
C77 C76 H76A 109.4 . . ?
C75 C76 H76B 109.4 . . ?
C77 C76 H76B 109.4 . . ?
H76A C76 H76B 108.0 . . ?
C78 C77 C76 110.8(2) . . ?
C78 C77 H77A 109.5 . . ?
C76 C77 H77A 109.5 . . ?
C78 C77 H77B 109.5 . . ?
C76 C77 H77B 109.5 . . ?
H77A C77 H77B 108.1 . . ?
C79 C78 C77 112.8(2) . . ?
C79 C78 C73 109.4(2) . . ?
C77 C78 C73 110.1(2) . . ?
C79 C78 H78 108.1 . . ?
C77 C78 H78 108.1 . . ?
C73 C78 H78 108.1 . . ?
N7 C79 C80 116.9(2) . . ?
N7 C79 C78 118.0(2) . . ?
C80 C79 C78 125.1(2) . . ?
C79 C80 C81 121.2(2) . . ?
C79 C80 H80 119.4 . . ?
C81 C80 H80 119.4 . . ?
C82 C81 C80 119.2(2) . . ?
C82 C81 C84 120.5(2) . . ?
C80 C81 C84 120.2(2) . . ?
C81 C82 C83 121.7(2) . . ?
C81 C82 H82 119.2 . . ?
C83 C82 H82 119.2 . . ?
O14 C83 N7 118.3(2) . . ?
O14 C83 C82 127.1(2) . . ?
N7 C83 C82 114.7(2) . . ?
C81 C84 H84A 109.5 . . ?
C81 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
C81 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?
C86 C85 C90 110.6(2) . . ?
C86 C85 H85A 109.5 . . ?
C90 C85 H85A 109.5 . . ?
C86 C85 H85B 109.5 . . ?
C90 C85 H85B 109.5 . . ?
H85A C85 H85B 108.1 . . ?
C87 C86 C85 111.6(2) . . ?
C87 C86 H86A 109.3 . . ?
C85 C86 H86A 109.3 . . ?
C87 C86 H86B 109.3 . . ?
C85 C86 H86B 109.3 . . ?
H86A C86 H86B 108.0 . . ?
C88 C87 C86 110.9(2) . . ?
C88 C87 H87A 109.5 . . ?
C86 C87 H87A 109.5 . . ?
C88 C87 H87B 109.5 . . ?
C86 C87 H87B 109.5 . . ?
H87A C87 H87B 108.0 . . ?
C87 C88 C89 111.2(2) . . ?
C87 C88 H88A 109.4 . . ?
C89 C88 H88A 109.4 . . ?
C87 C88 H88B 109.4 . . ?
C89 C88 H88B 109.4 . . ?
H88A C88 H88B 108.0 . . ?
C90 C89 C88 109.9(2) . . ?
C90 C89 H89A 109.7 . . ?
C88 C89 H89A 109.7 . . ?
C90 C89 H89B 109.7 . . ?
C88 C89 H89B 109.7 . . ?
H89A C89 H89B 108.2 . . ?
C91 C90 C89 112.8(2) . . ?
C91 C90 C85 110.7(2) . . ?
C89 C90 C85 110.2(2) . . ?
C91 C90 H90 107.6 . . ?
C89 C90 H90 107.6 . . ?
C85 C90 H90 107.6 . . ?
N8 C91 C92 117.3(2) . . ?
N8 C91 C90 116.8(2) . . ?
C92 C91 C90 125.9(2) . . ?
C91 C92 C93 121.3(2) . . ?
C91 C92 H92 119.3 . . ?
C93 C92 H92 119.3 . . ?
C94 C93 C92 118.8(2) . . ?
C94 C93 C96 120.7(2) . . ?
C92 C93 C96 120.4(2) . . ?
C93 C94 C95 122.1(2) . . ?
C93 C94 H94 119.0 . . ?
C95 C94 H94 119.0 . . ?
O16 C95 N8 118.1(2) . . ?
O16 C95 C94 127.3(2) . . ?
N8 C95 C94 114.7(2) . . ?
C93 C96 H96A 109.5 . . ?
C93 C96 H96B 109.5 . . ?
H96A C96 H96B 109.5 . . ?
C93 C96 H96C 109.5 . . ?
H96A C96 H96C 109.5 . . ?
H96B C96 H96C 109.5 . . ?
C102 C97 C98 111.4(2) . . ?
C102 C97 H97A 109.4 . . ?
C98 C97 H97A 109.4 . . ?
C102 C97 H97B 109.4 . . ?
C98 C97 H97B 109.4 . . ?
H97A C97 H97B 108.0 . . ?
C99 C98 C97 111.4(2) . . ?
C99 C98 H98A 109.3 . . ?
C97 C98 H98A 109.3 . . ?
C99 C98 H98B 109.3 . . ?
C97 C98 H98B 109.3 . . ?
H98A C98 H98B 108.0 . . ?
C100 C99 C98 111.2(2) . . ?
C100 C99 H99A 109.4 . . ?
C98 C99 H99A 109.4 . . ?
C100 C99 H99B 109.4 . . ?
C98 C99 H99B 109.4 . . ?
H99A C99 H99B 108.0 . . ?
C99 C100 C101 111.6(2) . . ?
C99 C100 H10A 109.3 . . ?
C101 C100 H10A 109.3 . . ?
C99 C100 H10B 109.3 . . ?
C101 C100 H10B 109.3 . . ?
H10A C100 H10B 108.0 . . ?
C100 C101 C102 110.1(2) . . ?
C100 C101 H10C 109.6 . . ?
C102 C101 H10C 109.6 . . ?
C100 C101 H10D 109.6 . . ?
C102 C101 H10D 109.6 . . ?
H10C C101 H10D 108.2 . . ?
C103 C102 C101 112.8(2) . . ?
C103 C102 C97 109.9(2) . . ?
C101 C102 C97 110.5(2) . . ?
C103 C102 H102 107.8 . . ?
C101 C102 H102 107.8 . . ?
C97 C102 H102 107.8 . . ?
C104 C103 N9 117.5(2) . . ?
C104 C103 C102 125.3(2) . . ?
N9 C103 C102 117.2(2) . . ?
C103 C104 C105 120.8(2) . . ?
C103 C104 H104 119.6 . . ?
C105 C104 H104 119.6 . . ?
C106 C105 C104 119.2(2) . . ?
C106 C105 C108 120.8(2) . . ?
C104 C105 C108 120.0(2) . . ?
C105 C106 C107 122.1(2) . . ?
C105 C106 H106 119.0 . . ?
C107 C106 H106 119.0 . . ?
O18 C107 N9 118.9(2) . . ?
O18 C107 C106 126.7(2) . . ?
N9 C107 C106 114.4(2) . . ?
C105 C108 H10E 109.5 . . ?
C105 C108 H10F 109.5 . . ?
H10E C108 H10F 109.5 . . ?
C105 C108 H10G 109.5 . . ?
H10E C108 H10G 109.5 . . ?
H10F C108 H10G 109.5 . . ?
C110 C109 C114 111.4(2) . . ?
C110 C109 H10H 109.4 . . ?
C114 C109 H10H 109.4 . . ?
C110 C109 H10I 109.4 . . ?
C114 C109 H10I 109.4 . . ?
H10H C109 H10I 108.0 . . ?
C109 C110 C111 111.1(3) . . ?
C109 C110 H11A 109.4 . . ?
C111 C110 H11A 109.4 . . ?
C109 C110 H11B 109.4 . . ?
C111 C110 H11B 109.4 . . ?
H11A C110 H11B 108.0 . . ?
C112 C111 C110 111.6(3) . . ?
C112 C111 H11C 109.3 . . ?
C110 C111 H11C 109.3 . . ?
C112 C111 H11D 109.3 . . ?
C110 C111 H11D 109.3 . . ?
H11C C111 H11D 108.0 . . ?
C113 C112 C111 111.6(3) . . ?
C113 C112 H11E 109.3 . . ?
C111 C112 H11E 109.3 . . ?
C113 C112 H11F 109.3 . . ?
C111 C112 H11F 109.3 . . ?
H11E C112 H11F 108.0 . . ?
C114 C113 C112 109.3(2) . . ?
C114 C113 H11G 109.8 . . ?
C112 C113 H11G 109.8 . . ?
C114 C113 H11H 109.8 . . ?
C112 C113 H11H 109.8 . . ?
H11G C113 H11H 108.3 . . ?
C115 C114 C113 113.7(2) . . ?
C115 C114 C109 108.6(2) . . ?
C113 C114 C109 110.6(2) . . ?
C115 C114 H114 107.9 . . ?
C113 C114 H114 107.9 . . ?
C109 C114 H114 107.9 . . ?
N10 C115 C116 117.2(3) . . ?
N10 C115 C114 117.1(2) . . ?
C116 C115 C114 125.7(3) . . ?
C115 C116 C117 121.0(3) . . ?
C115 C116 H116 119.5 . . ?
C117 C116 H116 119.5 . . ?
C118 C117 C116 119.5(3) . . ?
C118 C117 C120 120.7(3) . . ?
C116 C117 C120 119.8(3) . . ?
C117 C118 C119 121.8(3) . . ?
C117 C118 H118 119.1 . . ?
C119 C118 H118 119.1 . . ?
O20 C119 N10 119.0(3) . . ?
O20 C119 C118 126.5(3) . . ?
N10 C119 C118 114.5(3) . . ?
C117 C120 H12D 109.5 . . ?
C117 C120 H12E 109.5 . . ?
H12D C120 H12E 109.5 . . ?
C117 C120 H12F 109.5 . . ?
H12D C120 H12F 109.5 . . ?
H12E C120 H12F 109.5 . . ?
C122 C121 C126 110.08(19) . . ?
C122 C121 H12G 109.6 . . ?
C126 C121 H12G 109.6 . . ?
C122 C121 H12H 109.6 . . ?
C126 C121 H12H 109.6 . . ?
H12G C121 H12H 108.2 . . ?
C123 C122 C121 111.2(2) . . ?
C123 C122 H12I 109.4 . . ?
C121 C122 H12I 109.4 . . ?
C123 C122 H12J 109.4 . . ?
C121 C122 H12J 109.4 . . ?
H12I C122 H12J 108.0 . . ?
C122 C123 C124 111.4(2) . . ?
C122 C123 H12K 109.3 . . ?
C124 C123 H12K 109.3 . . ?
C122 C123 H12L 109.3 . . ?
C124 C123 H12L 109.3 . . ?
H12K C123 H12L 108.0 . . ?
C123 C124 C125 111.4(2) . . ?
C123 C124 H12M 109.4 . . ?
C125 C124 H12M 109.4 . . ?
C123 C124 H12N 109.4 . . ?
C125 C124 H12N 109.4 . . ?
H12M C124 H12N 108.0 . . ?
C124 C125 C126 110.6(2) . . ?
C124 C125 H12O 109.5 . . ?
C126 C125 H12O 109.5 . . ?
C124 C125 H12P 109.5 . . ?
C126 C125 H12P 109.5 . . ?
H12O C125 H12P 108.1 . . ?
C127 C126 C121 111.31(19) . . ?
C127 C126 C125 113.0(2) . . ?
C121 C126 C125 109.04(19) . . ?
C127 C126 H126 107.7 . . ?
C121 C126 H126 107.7 . . ?
C125 C126 H126 107.7 . . ?
N11 C127 C128 116.9(2) . . ?
N11 C127 C126 116.9(2) . . ?
C128 C127 C126 126.3(2) . . ?
C127 C128 C129 120.9(2) . . ?
C127 C128 H128 119.5 . . ?
C129 C128 H128 119.5 . . ?
C130 C129 C128 119.5(2) . . ?
C130 C129 C132 121.4(2) . . ?
C128 C129 C132 119.0(2) . . ?
C129 C130 C131 121.9(2) . . ?
C129 C130 H130 119.1 . . ?
C131 C130 H130 119.1 . . ?
O22 C131 N11 118.6(2) . . ?
O22 C131 C130 127.3(2) . . ?
N11 C131 C130 114.2(2) . . ?
C129 C132 H13C 109.5 . . ?
C129 C132 H13D 109.5 . . ?
H13C C132 H13D 109.5 . . ?
C129 C132 H13E 109.5 . . ?
H13C C132 H13E 109.5 . . ?
H13D C132 H13E 109.5 . . ?
C134 C133 C138 111.4(2) . . ?
C134 C133 H13F 109.4 . . ?
C138 C133 H13F 109.4 . . ?
C134 C133 H13G 109.4 . . ?
C138 C133 H13G 109.4 . . ?
H13F C133 H13G 108.0 . . ?
C133 C134 C135 111.2(2) . . ?
C133 C134 H13H 109.4 . . ?
C135 C134 H13H 109.4 . . ?
C133 C134 H13I 109.4 . . ?
C135 C134 H13I 109.4 . . ?
H13H C134 H13I 108.0 . . ?
C136 C135 C134 111.1(2) . . ?
C136 C135 H13J 109.4 . . ?
C134 C135 H13J 109.4 . . ?
C136 C135 H13K 109.4 . . ?
C134 C135 H13K 109.4 . . ?
H13J C135 H13K 108.0 . . ?
C135 C136 C137 111.3(2) . . ?
C135 C136 H13L 109.4 . . ?
C137 C136 H13L 109.4 . . ?
C135 C136 H13M 109.4 . . ?
C137 C136 H13M 109.4 . . ?
H13L C136 H13M 108.0 . . ?
C136 C137 C138 110.5(2) . . ?
C136 C137 H13N 109.5 . . ?
C138 C137 H13N 109.5 . . ?
C136 C137 H13O 109.5 . . ?
C138 C137 H13O 109.5 . . ?
H13N C137 H13O 108.1 . . ?
C139 C138 C137 113.1(2) . . ?
C139 C138 C133 110.4(2) . . ?
C137 C138 C133 110.4(2) . . ?
C139 C138 H138 107.6 . . ?
C137 C138 H138 107.6 . . ?
C133 C138 H138 107.6 . . ?
N12 C139 C140 116.8(2) . . ?
N12 C139 C138 118.0(2) . . ?
C140 C139 C138 125.2(2) . . ?
C139 C140 C141 121.2(2) . . ?
C139 C140 H140 119.4 . . ?
C141 C140 H140 119.4 . . ?
C142 C141 C140 119.2(2) . . ?
C142 C141 C144 121.0(3) . . ?
C140 C141 C144 119.8(2) . . ?
C141 C142 C143 121.7(3) . . ?
C141 C142 H142 119.1 . . ?
C143 C142 H142 119.1 . . ?
O24 C143 N12 118.3(3) . . ?
O24 C143 C142 126.8(3) . . ?
N12 C143 C142 114.9(2) . . ?
C141 C144 H14C 109.5 . . ?
C141 C144 H14D 109.5 . . ?
H14C C144 H14D 109.5 . . ?
C141 C144 H14E 109.5 . . ?
H14C C144 H14E 109.5 . . ?
H14D C144 H14E 109.5 . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.070


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Fluconazole-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987331'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Fluconazole
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 F2 N6 O'
_chemical_formula_sum            'C13 H12 F2 N6 O'
_chemical_formula_weight         306.29
_chemical_melting_point          414K
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'
O O 0.0492 0.0322 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.9345(2)
_cell_length_b                   6.02210(10)
_cell_length_c                   34.8527(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2714.78(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10079
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5760
_cell_measurement_theta_min      2.5540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            22563
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.467
_diffrn_reflns_theta_min         2.536
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00 104.00   0.50    0.10    --   46.37  57.00  60.00  148
  2  ω     91.00 178.00   0.50    0.41    --  105.44  45.00 -90.00  174
  3  ω     88.00 178.00   0.50    0.41    --  105.44  15.00-150.00  180
  4  ω     76.00 178.00   0.50    0.41    --  105.44 125.00-120.00  204
  5  ω     33.00 108.00   0.50    0.41    --  105.44 -94.00-150.00  150
  6  ω     15.00  95.00   0.50    0.10    --   46.37-125.00  30.00  160
  7  ω     33.00 108.00   0.50    0.41    --  105.44 -94.00 120.00  150
  8  ω     30.00 118.00   0.50    0.10    --   46.37  57.00 150.00  176
  9  ω   -118.00 -27.00   0.50    0.41    -- -100.00 127.00  19.00  182
 10  ω   -115.00 -25.00   0.50    0.41    -- -100.00  30.00 -60.00  180
 11  ω   -120.00 -32.00   0.50    0.10    --  -46.37 -35.00  -0.00  176
 12  ω   -118.00 -71.00   0.50    0.10    --  -46.37-125.00 -90.00   94
 13  ω   -118.00 -23.00   0.50    0.10    --  -46.37 -77.00 -60.00  190
 14  ω   -118.00 -71.00   0.50    0.10    --  -46.37-125.00 120.00   94
 15  ω   -118.00 -71.00   0.50    0.10    --  -46.37-125.00 150.00   94
 16  ω   -174.00 -85.00   0.50    0.41    -- -100.00 -35.00  -0.00  178
 17  ω   -128.00 -27.00   0.50    0.41    -- -100.00  87.00 -51.00  202
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0787106000
_diffrn_orient_matrix_UB_12      -0.0111890000
_diffrn_orient_matrix_UB_13      -0.0418298000
_diffrn_orient_matrix_UB_21      -0.2153407000
_diffrn_orient_matrix_UB_22      -0.0520766000
_diffrn_orient_matrix_UB_23      0.0140104000
_diffrn_orient_matrix_UB_31      -0.1138663000
_diffrn_orient_matrix_UB_32      0.1064966000
_diffrn_orient_matrix_UB_33      0.0024760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2470
_reflns_number_total             2776
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.050
_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)+(0.0528P)²+3.0470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00C,H00D), C00H(H00E,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00F(H00F), C00I(H00I), C00J(H00J), C00L(H00L),
 C00M(H00M)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
F001 F 0.33174(9) 0.8380(2) 0.59026(4) 0.0355(3) Uani 1 1 d . . . . .
O002 O 0.53069(9) 0.4277(2) 0.65791(4) 0.0243(3) Uani 1 1 d . . . . .
H002 H 0.584421 0.421037 0.645473 0.036 Uiso 1 1 calc R U . . .
F003 F 0.36764(11) 0.3457(3) 0.48739(4) 0.0501(4) Uani 1 1 d . . . . .
N004 N 0.60781(11) 0.8493(2) 0.63174(4) 0.0193(3) Uani 1 1 d . . . . .
N005 N 0.77554(11) 0.8749(2) 0.62723(4) 0.0216(3) Uani 1 1 d . . . . .
N006 N 0.62651(12) 0.8615(3) 0.59328(4) 0.0217(3) Uani 1 1 d . . . . .
N007 N 0.36732(12) 0.5789(3) 0.70320(5) 0.0276(4) Uani 1 1 d . . . . .
N008 N 0.35491(13) 0.7825(3) 0.72000(5) 0.0348(4) Uani 1 1 d . . . . .
N009 N 0.38889(14) 0.5177(4) 0.76437(5) 0.0426(5) Uani 1 1 d . . . . .
C00A C 0.72862(14) 0.8769(3) 0.59231(5) 0.0221(4) Uani 1 1 d . . . . .
H00A H 0.765448 0.888297 0.569481 0.027 Uiso 1 1 calc R U . . .
C00B C 0.69646(13) 0.8572(3) 0.65128(5) 0.0206(4) Uani 1 1 d . . . . .
H00B H 0.701989 0.851166 0.677866 0.025 Uiso 1 1 calc R U . . .
C00C C 0.44222(13) 0.5268(3) 0.59858(5) 0.0224(4) Uani 1 1 d . . . . .
C00D C 0.46310(13) 0.5825(3) 0.64075(5) 0.0216(4) Uani 1 1 d . . . . .
C00E C 0.50370(13) 0.8201(3) 0.64697(5) 0.0225(4) Uani 1 1 d . . . . .
H00C H 0.457437 0.924486 0.634531 0.027 Uiso 1 1 calc R U . . .
H00D H 0.503948 0.853044 0.674216 0.027 Uiso 1 1 calc R U . . .
C00F C 0.48307(15) 0.3356(3) 0.58170(6) 0.0260(4) Uani 1 1 d . . . . .
H00F H 0.527560 0.246762 0.595979 0.031 Uiso 1 1 calc R U . . .
C00G C 0.37671(14) 0.6515(3) 0.57544(6) 0.0269(4) Uani 1 1 d . . . . .
C00H C 0.35961(14) 0.5518(4) 0.66203(5) 0.0257(4) Uani 1 1 d . . . . .
H00E H 0.310177 0.658628 0.652156 0.031 Uiso 1 1 calc R U . . .
H00G H 0.333084 0.404517 0.656561 0.031 Uiso 1 1 calc R U . . .
C00I C 0.45954(16) 0.2738(4) 0.54440(6) 0.0327(5) Uani 1 1 d . . . . .
H00I H 0.487515 0.145518 0.533764 0.039 Uiso 1 1 calc R U . . .
C00J C 0.35196(16) 0.5986(4) 0.53825(6) 0.0335(5) Uani 1 1 d . . . . .
H00J H 0.308779 0.688581 0.523630 0.040 Uiso 1 1 calc R U . . .
C00K C 0.39401(16) 0.4062(4) 0.52353(6) 0.0347(5) Uani 1 1 d . . . . .
C00L C 0.38736(16) 0.4267(4) 0.72977(6) 0.0358(5) Uani 1 1 d . . . . .
H00L H 0.398746 0.276988 0.724774 0.043 Uiso 1 1 calc R U . . .
C00M C 0.36908(16) 0.7347(5) 0.75661(6) 0.0405(6) Uani 1 1 d . . . . .
H00M H 0.365732 0.842136 0.775743 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00G 1.366(2) . ?
O002 H002 0.8200 . ?
O002 C00D 1.411(2) . ?
F003 C00K 1.355(2) . ?
N004 N006 1.364(2) . ?
N004 C00B 1.335(2) . ?
N004 C00E 1.458(2) . ?
N005 C00A 1.360(2) . ?
N005 C00B 1.327(2) . ?
N006 C00A 1.324(2) . ?
N007 N008 1.368(3) . ?
N007 C00H 1.448(2) . ?
N007 C00L 1.329(3) . ?
N008 C00M 1.321(3) . ?
N009 C00L 1.325(3) . ?
N009 C00M 1.359(4) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00C C00D 1.532(2) . ?
C00C C00F 1.397(3) . ?
C00C C00G 1.390(3) . ?
C00D C00E 1.540(3) . ?
C00D C00H 1.541(2) . ?
C00E H00C 0.9700 . ?
C00E H00D 0.9700 . ?
C00F H00F 0.9300 . ?
C00F C00I 1.386(3) . ?
C00G C00J 1.373(3) . ?
C00H H00E 0.9700 . ?
C00H H00G 0.9700 . ?
C00I H00I 0.9300 . ?
C00I C00K 1.372(3) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.379(3) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?

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 H002 109.5 . . ?
N006 N004 C00E 121.88(14) . . ?
C00B N004 N006 110.32(14) . . ?
C00B N004 C00E 127.72(15) . . ?
C00B N005 C00A 102.83(15) . . ?
C00A N006 N004 101.86(14) . . ?
N008 N007 C00H 121.15(17) . . ?
C00L N007 N008 110.04(18) . . ?
C00L N007 C00H 128.80(19) . . ?
C00M N008 N007 101.67(19) . . ?
C00L N009 C00M 102.35(19) . . ?
N005 C00A H00A 122.5 . . ?
N006 C00A N005 114.94(16) . . ?
N006 C00A H00A 122.5 . . ?
N004 C00B H00B 125.0 . . ?
N005 C00B N004 110.04(16) . . ?
N005 C00B H00B 125.0 . . ?
C00F C00C C00D 121.19(16) . . ?
C00G C00C C00D 123.09(17) . . ?
C00G C00C C00F 115.57(18) . . ?
O002 C00D C00C 111.78(15) . . ?
O002 C00D C00E 110.08(14) . . ?
O002 C00D C00H 104.77(14) . . ?
C00C C00D C00E 113.51(15) . . ?
C00C C00D C00H 106.39(14) . . ?
C00E C00D C00H 109.87(15) . . ?
N004 C00E C00D 112.07(14) . . ?
N004 C00E H00C 109.2 . . ?
N004 C00E H00D 109.2 . . ?
C00D C00E H00C 109.2 . . ?
C00D C00E H00D 109.2 . . ?
H00C C00E H00D 107.9 . . ?
C00C C00F H00F 118.9 . . ?
C00I C00F C00C 122.23(19) . . ?
C00I C00F H00F 118.9 . . ?
F001 C00G C00C 118.96(17) . . ?
F001 C00G C00J 116.64(18) . . ?
C00J C00G C00C 124.4(2) . . ?
N007 C00H C00D 113.80(15) . . ?
N007 C00H H00E 108.8 . . ?
N007 C00H H00G 108.8 . . ?
C00D C00H H00E 108.8 . . ?
C00D C00H H00G 108.8 . . ?
H00E C00H H00G 107.7 . . ?
C00F C00I H00I 120.8 . . ?
C00K C00I C00F 118.5(2) . . ?
C00K C00I H00I 120.8 . . ?
C00G C00J H00J 121.5 . . ?
C00G C00J C00K 117.00(19) . . ?
C00K C00J H00J 121.5 . . ?
F003 C00K C00I 119.5(2) . . ?
F003 C00K C00J 118.2(2) . . ?
C00I C00K C00J 122.32(19) . . ?
N007 C00L H00L 124.7 . . ?
N009 C00L N007 110.6(2) . . ?
N009 C00L H00L 124.7 . . ?
N008 C00M N009 115.3(2) . . ?
N008 C00M H00M 122.3 . . ?
N009 C00M H00M 122.3 . . ?

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
F001 C00G C00J C00K -177.67(17) . . . . ?
O002 C00D C00E N004 57.54(19) . . . . ?
O002 C00D C00H N007 56.3(2) . . . . ?
N004 N006 C00A N005 0.1(2) . . . . ?
N006 N004 C00B N005 0.1(2) . . . . ?
N006 N004 C00E C00D 73.3(2) . . . . ?
N007 N008 C00M N009 -0.3(2) . . . . ?
N008 N007 C00H C00D 89.4(2) . . . . ?
N008 N007 C00L N009 0.2(2) . . . . ?
C00A N005 C00B N004 -0.04(19) . . . . ?
C00B N004 N006 C00A -0.16(19) . . . . ?
C00B N004 C00E C00D -103.2(2) . . . . ?
C00B N005 C00A N006 -0.1(2) . . . . ?
C00C C00D C00E N004 -68.60(19) . . . . ?
C00C C00D C00H N007 174.82(16) . . . . ?
C00C C00F C00I C00K 0.2(3) . . . . ?
C00C C00G C00J C00K 1.3(3) . . . . ?
C00D C00C C00F C00I 175.50(17) . . . . ?
C00D C00C C00G F001 2.8(3) . . . . ?
C00D C00C C00G C00J -176.16(18) . . . . ?
C00E N004 N006 C00A -177.23(16) . . . . ?
C00E N004 C00B N005 176.98(16) . . . . ?
C00E C00D C00H N007 -61.9(2) . . . . ?
C00F C00C C00D O002 3.4(2) . . . . ?
C00F C00C C00D C00E 128.64(18) . . . . ?
C00F C00C C00D C00H -110.41(19) . . . . ?
C00F C00C C00G F001 178.42(16) . . . . ?
C00F C00C C00G C00J -0.5(3) . . . . ?
C00F C00I C00K F003 -178.16(18) . . . . ?
C00F C00I C00K C00J 0.7(3) . . . . ?
C00G C00C C00D O002 178.82(17) . . . . ?
C00G C00C C00D C00E -55.9(2) . . . . ?
C00G C00C C00D C00H 65.0(2) . . . . ?
C00G C00C C00F C00I -0.2(3) . . . . ?
C00G C00J C00K F003 177.50(18) . . . . ?
C00G C00J C00K C00I -1.4(3) . . . . ?
C00H N007 N008 C00M -179.15(17) . . . . ?
C00H N007 C00L N009 179.35(18) . . . . ?
C00H C00D C00E N004 172.42(14) . . . . ?
C00L N007 N008 C00M 0.1(2) . . . . ?
C00L N007 C00H C00D -89.7(2) . . . . ?
C00L N009 C00M N008 0.4(3) . . . . ?
C00M N009 C00L N007 -0.4(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.627
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Repaglinide-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987346'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-25
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Repaglinide
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H36 N2 O4'
_chemical_formula_sum            'C27 H36 N2 O4'
_chemical_formula_weight         452.58
_chemical_absolute_configuration ad
_chemical_melting_point          409K
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'
O O 0.0492 0.0322 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.32210(10)
_cell_length_b                   13.3053(2)
_cell_length_c                   22.7527(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2519.36(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13390
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.6040
_cell_measurement_theta_min      5.1250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25212
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.883
_diffrn_reflns_theta_min         3.849
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  27.00   0.50    0.64    --  -46.62  38.00  60.00  176
  2  ω     14.00  94.00   0.50    0.64    --   46.62-123.00 -77.00  160
  3  ω   -120.00 -32.00   0.50    0.64    --  -46.62 -38.00  90.00  176
  4  ω   -119.00 -73.00   0.50    0.64    --  -46.62-123.00 -77.00   92
  5  ω   -119.00 -71.00   0.50    0.64    --  -46.62-125.00 -30.00   96
  6  ω   -119.00 -30.00   0.50    0.64    --  -46.62 -57.00 -90.00  178
  7  ω   -119.00 -23.00   0.50    0.64    --  -46.62 -77.00-150.00  192
  8  ω   -119.00 -30.00   0.50    0.64    --  -46.62 -57.00   0.00  178
  9  ω     34.00 115.00   0.50    2.55    --  107.00-123.00-168.00  162
 10  ω     34.00 115.00   0.50    2.55    --  107.00-123.00 -77.00  162
 11  ω     34.00 109.00   0.50    2.55    --  107.00 -94.00   0.00  150
 12  ω     31.00 125.00   0.50    2.55    --  107.00 -15.00 -60.00  188
 13  ω     85.00 178.00   0.50    2.55    --  107.00  10.00-176.00  186
 14  ω     34.00 109.00   0.50    2.55    --  107.00 -94.00-120.00  150
 15  ω     32.00 123.00   0.50    2.55    --  107.00 -30.00-180.00  182
 16  ω     34.00 131.00   0.50    2.55    --  107.00 -77.00-150.00  194
 17  ω     34.00 109.00   0.50    2.55    --  107.00 -94.00-180.00  150
 18  ω     35.00 122.00   0.50    2.55    --  107.00 -45.00-180.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0030190000
_diffrn_orient_matrix_UB_12      0.0919930000
_diffrn_orient_matrix_UB_13      -0.0410167000
_diffrn_orient_matrix_UB_21      0.0248655000
_diffrn_orient_matrix_UB_22      -0.0693909000
_diffrn_orient_matrix_UB_23      -0.0534841000
_diffrn_orient_matrix_UB_31      -0.1834467000
_diffrn_orient_matrix_UB_32      -0.0109028000
_diffrn_orient_matrix_UB_33      -0.0065769000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                4875
_reflns_number_total             5214
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1927 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.049
_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)+(0.0537P)²+0.3297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00I), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00J(H00D,H00F), C00O(H00G,H00J), C00P(H00O,H00P), C00S(H00U,
 H00V), C00U(H00Z,H), C00V(H00,HA), C00X(H2,HD)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C00C(H00C), C00E(H00E), C00H(H00H), C00K(H00K), C00M(H00M),
 C00N(H00N), C00Q(H00Q)
2.d Idealised Me refined as rotating group:
 C00R(H00R,H00S,H00T), C00T(H00W,H00X,H00Y), C00W(H1,HB,HC)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_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
O001 O 0.62397(16) 0.52368(11) 0.68087(6) 0.0279(3) Uani 1 1 d . . . . .
O002 O 1.17440(16) 0.45981(10) 0.78455(7) 0.0271(3) Uani 1 1 d . . . . .
O003 O 1.30674(17) 0.27674(12) 0.79433(8) 0.0369(4) Uani 1 1 d . . . . .
O004 O 1.14393(17) 0.15627(11) 0.82511(8) 0.0344(4) Uani 1 1 d . . . . .
H004 H 1.226357 0.122800 0.822501 0.052 Uiso 1 1 calc R U . . .
N005 N 0.44806(19) 0.39932(13) 0.70102(7) 0.0231(3) Uani 1 1 d . . . . .
H005 H 0.399094 0.366653 0.728280 0.028 Uiso 1 1 calc R U . . .
N006 N 0.3581(2) 0.52514(13) 0.55017(8) 0.0297(4) Uani 1 1 d . . . . .
C007 C 1.1741(2) 0.24975(15) 0.80941(8) 0.0226(4) Uani 1 1 d . . . . .
C008 C 1.0266(2) 0.31366(15) 0.80977(8) 0.0217(4) Uani 1 1 d . . . . .
C009 C 0.7377(2) 0.42138(14) 0.79686(8) 0.0221(4) Uani 1 1 d . . . . .
C00A C 1.0294(2) 0.41638(15) 0.79336(8) 0.0222(4) Uani 1 1 d . . . . .
C00B C 0.5521(2) 0.46969(14) 0.71694(9) 0.0218(4) Uani 1 1 d . . . . .
C00C C 0.8843(2) 0.46783(15) 0.78677(9) 0.0236(4) Uani 1 1 d . . . . .
H00C H 0.886041 0.534931 0.775338 0.028 Uiso 1 1 calc R U . . .
C00D C 0.2204(2) 0.48214(15) 0.57901(9) 0.0267(4) Uani 1 1 d . . . . .
C00E C 0.8775(2) 0.27032(15) 0.82295(9) 0.0241(4) Uani 1 1 d . . . . .
H00E H 0.874550 0.204338 0.836398 0.029 Uiso 1 1 calc R U . . .
C00F C 0.2436(2) 0.40937(15) 0.62309(9) 0.0245(4) Uani 1 1 d . . . . .
C00G C 0.5843(2) 0.47766(15) 0.78271(9) 0.0239(4) Uani 1 1 d . . . . .
H00A H 0.595187 0.547687 0.793883 0.029 Uiso 1 1 calc R U . . .
H00B H 0.495281 0.449024 0.804532 0.029 Uiso 1 1 calc R U . . .
C00H C 0.1096(2) 0.36889(16) 0.65098(9) 0.0269(4) Uani 1 1 d . . . . .
H00H H 0.124109 0.320856 0.680199 0.032 Uiso 1 1 calc R U . . .
C00I C 0.4113(2) 0.37373(15) 0.63972(9) 0.0236(4) Uani 1 1 d . . . . .
H00I H 0.489669 0.407029 0.614118 0.028 Uiso 1 1 calc R U . . .
C00J C 0.4297(2) 0.25948(15) 0.63290(9) 0.0252(4) Uani 1 1 d . . . . .
H00D H 0.537527 0.240737 0.644778 0.030 Uiso 1 1 calc R U . . .
H00F H 0.355227 0.226723 0.659526 0.030 Uiso 1 1 calc R U . . .
C00K C 0.7347(2) 0.32206(15) 0.81669(9) 0.0246(4) Uani 1 1 d . . . . .
H00K H 0.637463 0.291088 0.825578 0.030 Uiso 1 1 calc R U . . .
C00L C 0.3999(3) 0.21966(16) 0.57072(9) 0.0280(4) Uani 1 1 d . . . . .
H00L H 0.294948 0.244254 0.557501 0.034 Uiso 1 1 calc R U . . .
C00M C 0.0640(3) 0.51140(17) 0.56457(10) 0.0332(5) Uani 1 1 d . . . . .
H00M H 0.048046 0.559711 0.535617 0.040 Uiso 1 1 calc R U . . .
C00N C -0.0455(2) 0.39856(17) 0.63621(10) 0.0301(4) Uani 1 1 d . . . . .
H00N H -0.133469 0.370786 0.655489 0.036 Uiso 1 1 calc R U . . .
C00O C 1.1779(2) 0.56431(16) 0.76770(12) 0.0340(5) Uani 1 1 d . . . . .
H00G H 1.094037 0.576715 0.738985 0.041 Uiso 1 1 calc R U . . .
H00J H 1.280327 0.579165 0.749318 0.041 Uiso 1 1 calc R U . . .
C00P C 0.3971(3) 0.62479(16) 0.57431(10) 0.0324(5) Uani 1 1 d . . . . .
H00O H 0.405399 0.620435 0.616756 0.039 Uiso 1 1 calc R U . . .
H00P H 0.311475 0.671548 0.564905 0.039 Uiso 1 1 calc R U . . .
C00Q C -0.0679(3) 0.46958(18) 0.59271(10) 0.0337(5) Uani 1 1 d . . . . .
H00Q H -0.171233 0.489331 0.582303 0.040 Uiso 1 1 calc R U . . .
C00R C 0.3948(3) 0.10499(18) 0.57148(11) 0.0385(5) Uani 1 1 d . . . . .
H00R H 0.496607 0.079396 0.584481 0.058 Uiso 1 1 calc R U . . .
H00S H 0.372596 0.080556 0.532621 0.058 Uiso 1 1 calc R U . . .
H00T H 0.311886 0.082886 0.597831 0.058 Uiso 1 1 calc R U . . .
C00S C 0.5548(3) 0.6635(2) 0.54915(12) 0.0417(6) Uani 1 1 d . . . . .
H00U H 0.642312 0.621484 0.562901 0.050 Uiso 1 1 calc R U . . .
H00V H 0.573692 0.731333 0.563182 0.050 Uiso 1 1 calc R U . . .
C00T C 1.1542(3) 0.63298(18) 0.81925(14) 0.0458(6) Uani 1 1 d . . . . .
H00W H 1.166309 0.701484 0.806776 0.069 Uiso 1 1 calc R U . . .
H00X H 1.232736 0.617995 0.848887 0.069 Uiso 1 1 calc R U . . .
H00Y H 1.048378 0.623403 0.835093 0.069 Uiso 1 1 calc R U . . .
C00U C 0.3445(3) 0.5285(2) 0.48593(10) 0.0433(6) Uani 1 1 d . . . . .
H00Z H 0.261733 0.576069 0.474632 0.052 Uiso 1 1 calc R U . . .
H H 0.314569 0.462797 0.471094 0.052 Uiso 1 1 calc R U . . .
C00V C 0.5050(4) 0.5602(2) 0.45974(12) 0.0515(7) Uani 1 1 d . . . . .
H00 H 0.586901 0.511612 0.470323 0.062 Uiso 1 1 calc R U . . .
HA H 0.496808 0.561741 0.417219 0.062 Uiso 1 1 calc R U . . .
C00W C 0.5271(3) 0.2568(2) 0.52757(11) 0.0425(6) Uani 1 1 d . . . . .
H1 H 0.523636 0.328890 0.525584 0.064 Uiso 1 1 calc R U . . .
HB H 0.506147 0.229289 0.489335 0.064 Uiso 1 1 calc R U . . .
HC H 0.631443 0.235765 0.540645 0.064 Uiso 1 1 calc R U . . .
C00X C 0.5528(4) 0.6635(2) 0.48224(12) 0.0508(7) Uani 1 1 d . . . . .
H2 H 0.476901 0.713367 0.468180 0.061 Uiso 1 1 calc R U . . .
HD H 0.658461 0.680969 0.467440 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00B 1.244(2) . ?
O002 C00A 1.353(2) . ?
O002 C00O 1.443(2) . ?
O003 C007 1.210(2) . ?
O004 H004 0.8200 . ?
O004 C007 1.318(2) . ?
N005 H005 0.8600 . ?
N005 C00B 1.325(3) . ?
N005 C00I 1.468(3) . ?
N006 C00D 1.439(3) . ?
N006 C00P 1.471(3) . ?
N006 C00U 1.467(3) . ?
C007 C008 1.494(3) . ?
C008 C00A 1.417(3) . ?
C008 C00E 1.401(3) . ?
C009 C00C 1.387(3) . ?
C009 C00G 1.514(3) . ?
C009 C00K 1.397(3) . ?
C00A C00C 1.396(3) . ?
C00B C00G 1.524(3) . ?
C00C H00C 0.9300 . ?
C00D C00F 1.407(3) . ?
C00D C00M 1.398(3) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.381(3) . ?
C00F C00H 1.391(3) . ?
C00F C00I 1.522(3) . ?
C00G H00A 0.9700 . ?
C00G H00B 0.9700 . ?
C00H H00H 0.9300 . ?
C00H C00N 1.391(3) . ?
C00I H00I 0.9800 . ?
C00I C00J 1.536(3) . ?
C00J H00D 0.9700 . ?
C00J H00F 0.9700 . ?
C00J C00L 1.531(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9800 . ?
C00L C00R 1.526(3) . ?
C00L C00W 1.526(3) . ?
C00M H00M 0.9300 . ?
C00M C00Q 1.387(3) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.381(3) . ?
C00O H00G 0.9700 . ?
C00O H00J 0.9700 . ?
C00O C00T 1.500(4) . ?
C00P H00O 0.9700 . ?
C00P H00P 0.9700 . ?
C00P C00S 1.522(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9600 . ?
C00R H00S 0.9600 . ?
C00R H00T 0.9600 . ?
C00S H00U 0.9700 . ?
C00S H00V 0.9700 . ?
C00S C00X 1.523(4) . ?
C00T H00W 0.9600 . ?
C00T H00X 0.9600 . ?
C00T H00Y 0.9600 . ?
C00U H00Z 0.9700 . ?
C00U H 0.9700 . ?
C00U C00V 1.522(4) . ?
C00V H00 0.9700 . ?
C00V HA 0.9700 . ?
C00V C00X 1.520(4) . ?
C00W H1 0.9600 . ?
C00W HB 0.9600 . ?
C00W HC 0.9600 . ?
C00X H2 0.9700 . ?
C00X HD 0.9700 . ?

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
C00A O002 C00O 117.97(15) . . ?
C007 O004 H004 109.5 . . ?
C00B N005 H005 118.0 . . ?
C00B N005 C00I 124.01(16) . . ?
C00I N005 H005 118.0 . . ?
C00D N006 C00P 111.32(17) . . ?
C00D N006 C00U 113.89(18) . . ?
C00U N006 C00P 111.19(18) . . ?
O003 C007 O004 122.06(18) . . ?
O003 C007 C008 125.61(18) . . ?
O004 C007 C008 112.26(16) . . ?
C00A C008 C007 122.27(17) . . ?
C00E C008 C007 119.67(17) . . ?
C00E C008 C00A 117.93(17) . . ?
C00C C009 C00G 119.08(17) . . ?
C00C C009 C00K 119.40(17) . . ?
C00K C009 C00G 121.43(17) . . ?
O002 C00A C008 117.78(16) . . ?
O002 C00A C00C 123.10(17) . . ?
C00C C00A C008 119.12(17) . . ?
O001 C00B N005 122.81(18) . . ?
O001 C00B C00G 121.51(17) . . ?
N005 C00B C00G 115.62(17) . . ?
C009 C00C C00A 121.65(18) . . ?
C009 C00C H00C 119.2 . . ?
C00A C00C H00C 119.2 . . ?
C00F C00D N006 119.31(18) . . ?
C00M C00D N006 121.59(19) . . ?
C00M C00D C00F 119.10(19) . . ?
C008 C00E H00E 118.8 . . ?
C00K C00E C008 122.35(18) . . ?
C00K C00E H00E 118.8 . . ?
C00D C00F C00I 121.13(18) . . ?
C00H C00F C00D 118.81(19) . . ?
C00H C00F C00I 120.06(18) . . ?
C009 C00G C00B 108.84(15) . . ?
C009 C00G H00A 109.9 . . ?
C009 C00G H00B 109.9 . . ?
C00B C00G H00A 109.9 . . ?
C00B C00G H00B 109.9 . . ?
H00A C00G H00B 108.3 . . ?
C00F C00H H00H 119.2 . . ?
C00N C00H C00F 121.6(2) . . ?
C00N C00H H00H 119.2 . . ?
N005 C00I C00F 110.78(16) . . ?
N005 C00I H00I 108.8 . . ?
N005 C00I C00J 107.76(16) . . ?
C00F C00I H00I 108.8 . . ?
C00F C00I C00J 111.98(16) . . ?
C00J C00I H00I 108.8 . . ?
C00I C00J H00D 108.6 . . ?
C00I C00J H00F 108.6 . . ?
H00D C00J H00F 107.5 . . ?
C00L C00J C00I 114.83(17) . . ?
C00L C00J H00D 108.6 . . ?
C00L C00J H00F 108.6 . . ?
C009 C00K H00K 120.3 . . ?
C00E C00K C009 119.31(17) . . ?
C00E C00K H00K 120.3 . . ?
C00J C00L H00L 108.2 . . ?
C00R C00L C00J 109.88(18) . . ?
C00R C00L H00L 108.2 . . ?
C00W C00L C00J 111.72(18) . . ?
C00W C00L H00L 108.2 . . ?
C00W C00L C00R 110.54(19) . . ?
C00D C00M H00M 119.4 . . ?
C00Q C00M C00D 121.1(2) . . ?
C00Q C00M H00M 119.4 . . ?
C00H C00N H00N 120.2 . . ?
C00Q C00N C00H 119.5(2) . . ?
C00Q C00N H00N 120.2 . . ?
O002 C00O H00G 109.2 . . ?
O002 C00O H00J 109.2 . . ?
O002 C00O C00T 112.1(2) . . ?
H00G C00O H00J 107.9 . . ?
C00T C00O H00G 109.2 . . ?
C00T C00O H00J 109.2 . . ?
N006 C00P H00O 109.5 . . ?
N006 C00P H00P 109.5 . . ?
N006 C00P C00S 110.79(19) . . ?
H00O C00P H00P 108.1 . . ?
C00S C00P H00O 109.5 . . ?
C00S C00P H00P 109.5 . . ?
C00M C00Q H00Q 120.0 . . ?
C00N C00Q C00M 119.9(2) . . ?
C00N C00Q H00Q 120.0 . . ?
C00L C00R H00R 109.5 . . ?
C00L C00R H00S 109.5 . . ?
C00L C00R H00T 109.5 . . ?
H00R C00R H00S 109.5 . . ?
H00R C00R H00T 109.5 . . ?
H00S C00R H00T 109.5 . . ?
C00P C00S H00U 109.3 . . ?
C00P C00S H00V 109.3 . . ?
C00P C00S C00X 111.5(2) . . ?
H00U C00S H00V 108.0 . . ?
C00X C00S H00U 109.3 . . ?
C00X C00S H00V 109.3 . . ?
C00O C00T H00W 109.5 . . ?
C00O C00T H00X 109.5 . . ?
C00O C00T H00Y 109.5 . . ?
H00W C00T H00X 109.5 . . ?
H00W C00T H00Y 109.5 . . ?
H00X C00T H00Y 109.5 . . ?
N006 C00U H00Z 109.8 . . ?
N006 C00U H 109.8 . . ?
N006 C00U C00V 109.3(2) . . ?
H00Z C00U H 108.3 . . ?
C00V C00U H00Z 109.8 . . ?
C00V C00U H 109.8 . . ?
C00U C00V H00 109.6 . . ?
C00U C00V HA 109.6 . . ?
H00 C00V HA 108.1 . . ?
C00X C00V C00U 110.4(2) . . ?
C00X C00V H00 109.6 . . ?
C00X C00V HA 109.6 . . ?
C00L C00W H1 109.5 . . ?
C00L C00W HB 109.5 . . ?
C00L C00W HC 109.5 . . ?
H1 C00W HB 109.5 . . ?
H1 C00W HC 109.5 . . ?
HB C00W HC 109.5 . . ?
C00S C00X H2 109.7 . . ?
C00S C00X HD 109.7 . . ?
C00V C00X C00S 109.9(2) . . ?
C00V C00X H2 109.7 . . ?
C00V C00X HD 109.7 . . ?
H2 C00X HD 108.2 . . ?

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
O001 C00B C00G C009 -79.4(2) . . . . ?
O002 C00A C00C C009 -179.18(18) . . . . ?
O003 C007 C008 C00A -1.8(3) . . . . ?
O003 C007 C008 C00E 173.9(2) . . . . ?
O004 C007 C008 C00A -178.78(18) . . . . ?
O004 C007 C008 C00E -3.1(3) . . . . ?
N005 C00B C00G C009 98.04(19) . . . . ?
N005 C00I C00J C00L -178.46(16) . . . . ?
N006 C00D C00F C00H 179.51(18) . . . . ?
N006 C00D C00F C00I -1.4(3) . . . . ?
N006 C00D C00M C00Q -179.9(2) . . . . ?
N006 C00P C00S C00X 54.4(3) . . . . ?
N006 C00U C00V C00X -59.9(3) . . . . ?
C007 C008 C00A O002 -8.6(3) . . . . ?
C007 C008 C00A C00C 171.10(18) . . . . ?
C007 C008 C00E C00K -171.50(18) . . . . ?
C008 C00A C00C C009 1.1(3) . . . . ?
C008 C00E C00K C009 -0.4(3) . . . . ?
C00A O002 C00O C00T 79.5(2) . . . . ?
C00A C008 C00E C00K 4.4(3) . . . . ?
C00B N005 C00I C00F -108.7(2) . . . . ?
C00B N005 C00I C00J 128.50(19) . . . . ?
C00C C009 C00G C00B 80.7(2) . . . . ?
C00C C009 C00K C00E -3.3(3) . . . . ?
C00D N006 C00P C00S 172.70(18) . . . . ?
C00D N006 C00U C00V -171.5(2) . . . . ?
C00D C00F C00H C00N 0.1(3) . . . . ?
C00D C00F C00I N005 116.9(2) . . . . ?
C00D C00F C00I C00J -122.7(2) . . . . ?
C00D C00M C00Q C00N 0.7(3) . . . . ?
C00E C008 C00A O002 175.60(17) . . . . ?
C00E C008 C00A C00C -4.7(3) . . . . ?
C00F C00D C00M C00Q -0.3(3) . . . . ?
C00F C00H C00N C00Q 0.2(3) . . . . ?
C00F C00I C00J C00L 59.5(2) . . . . ?
C00G C009 C00C C00A -173.49(18) . . . . ?
C00G C009 C00K C00E 173.05(18) . . . . ?
C00H C00F C00I N005 -64.0(2) . . . . ?
C00H C00F C00I C00J 56.3(2) . . . . ?
C00H C00N C00Q C00M -0.6(3) . . . . ?
C00I N005 C00B O001 3.0(3) . . . . ?
C00I N005 C00B C00G -174.45(16) . . . . ?
C00I C00F C00H C00N -179.0(2) . . . . ?
C00I C00J C00L C00R -170.91(17) . . . . ?
C00I C00J C00L C00W 66.0(2) . . . . ?
C00K C009 C00C C00A 3.0(3) . . . . ?
C00K C009 C00G C00B -95.7(2) . . . . ?
C00M C00D C00F C00H -0.1(3) . . . . ?
C00M C00D C00F C00I 178.99(19) . . . . ?
C00O O002 C00A C008 179.86(19) . . . . ?
C00O O002 C00A C00C 0.1(3) . . . . ?
C00P N006 C00D C00F -100.3(2) . . . . ?
C00P N006 C00D C00M 79.2(3) . . . . ?
C00P N006 C00U C00V 61.7(3) . . . . ?
C00P C00S C00X C00V -52.7(3) . . . . ?
C00U N006 C00D C00F 133.0(2) . . . . ?
C00U N006 C00D C00M -47.4(3) . . . . ?
C00U N006 C00P C00S -59.2(2) . . . . ?
C00U C00V C00X C00S 55.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.100
_oxdiff_exptl_absorpt_empirical_full_min 0.581
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Nimodipine-100k-HWRong
_database_code_depnum_ccdc_archive 'CCDC 1987341'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2020-06-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Nimodipine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O7'
_chemical_formula_sum            'C21 H26 N2 O7'
_chemical_formula_weight         418.44
_chemical_melting_point          399K
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'
O O 0.0492 0.0322 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.76260(10)
_cell_length_b                   10.72760(10)
_cell_length_c                   14.78350(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.3000(10)
_cell_angle_gamma                90
_cell_volume                     2115.00(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    30153
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8510
_cell_measurement_theta_min      3.1010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40061
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.841
_diffrn_reflns_theta_min         3.314
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  27.00   0.50    0.05    --  -46.37  85.00  -5.00  202
  2  ω    -25.00  74.00   0.50    0.05    --   46.37 -85.00-124.00  198
  3  ω   -127.00 -27.00   0.50    0.05    -- -100.00  85.00  -5.00  200
  4  ω   -173.00 -77.00   0.50    0.05    -- -100.00 -85.00-124.00  192
  5  ω     34.00 135.00   0.50    0.05    --  107.00 -85.00-124.00  202
  6  ω   -118.00 -71.00   0.50    0.05    --  -46.37-125.00  60.00   94
  7  ω    -62.00  27.00   0.50    0.05    --  -46.37  57.00 -60.00  178
  8  ω   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00-180.00  190
  9  ω   -118.00 -71.00   0.50    0.05    --  -46.37-125.00  30.00   94
 10  ω     31.00 122.00   0.50    0.05    --   46.37  19.00-120.00  182
 11  ω   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00 -60.00  174
 12  ω   -175.00 -82.00   0.50    0.05    -- -100.00 -15.00 120.00  186
 13  ω   -173.00 -81.00   0.50    0.05    -- -100.00 -94.00 -60.00  184
 14  ω     32.00 123.00   0.50    0.05    --  107.00 -30.00  90.00  182
 15  ω     90.00 178.00   0.50    0.05    --  107.00  61.00 -60.00  176
 16  ω     34.00 117.00   0.50    0.05    --  107.00-125.00-120.00  166
 17  ω     34.00 117.00   0.50    0.05    --  107.00-125.00 -90.00  166
 18  ω     35.00 122.00   0.50    0.05    --  107.00 -45.00  90.00  174
 19  ω     31.00 125.00   0.50    0.05    --  107.00 -15.00-180.00  188
 20  ω     32.00 123.00   0.50    0.05    --  107.00 -30.00-150.00  182
 21  ω     93.00 178.00   0.50    0.05    --  107.00  45.00 120.00  170
 22  ω     34.00 117.00   0.50    0.05    --  107.00-125.00  90.00  166
 23  ω     93.00 178.00   0.50    0.05    --  107.00  45.00  60.00  170
 24  ω     35.00 122.00   0.50    0.05    --  107.00 -45.00-120.00  174
 25  ω     92.00 178.00   0.50    0.05    --  107.00  30.00 -30.00  172
 26  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 120.00  150
 27  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 -30.00  150
 28  ω     93.00 178.00   0.50    0.05    --  107.00  45.00 150.00  170
 29  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 -90.00  150
 30  ω     34.00 117.00   0.50    0.05    --  107.00-125.00  60.00  166
 31  ω     81.00 178.00   0.50    0.05    --  107.00  85.00  -5.00  194
 32  ω   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00   0.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0974466000
_diffrn_orient_matrix_UB_12      -0.0546445000
_diffrn_orient_matrix_UB_13      -0.0619603000
_diffrn_orient_matrix_UB_21      -0.0582981000
_diffrn_orient_matrix_UB_22      0.1151953000
_diffrn_orient_matrix_UB_23      0.0196937000
_diffrn_orient_matrix_UB_31      0.0212215000
_diffrn_orient_matrix_UB_32      0.0658411000
_diffrn_orient_matrix_UB_33      -0.0857604000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4265
_reflns_number_total             4421
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.046
_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)+(0.0594P)²+1.0342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00R(H00R)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00C), C00J(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 N006(H006), C00B(H00B), C00D(H00D), C00O(H00O), C00P(H00P)
2.d Idealised Me refined as rotating group:
 C00M(H00H,H00I,H00J), C00Q(H00K,H00L,H00M), C00S(H00N,H00Q,H00S), C00T(H00T,
 H00U,H00V), C00U(H00W,H00X,H00Y)
;
_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
O001 O 0.73535(6) 0.77656(8) 0.36717(6) 0.0214(2) Uani 1 1 d . . . . .
O002 O 0.82680(6) 0.36067(8) 0.42867(7) 0.0246(2) Uani 1 1 d . . . . .
O003 O 0.72059(7) 0.89545(9) 0.18964(6) 0.0259(2) Uani 1 1 d . . . . .
O004 O 0.72103(7) 0.20132(9) 0.42938(8) 0.0321(2) Uani 1 1 d . . . . .
O005 O 0.58234(7) 0.85435(9) 0.36292(8) 0.0324(2) Uani 1 1 d . . . . .
N006 N 0.48723(8) 0.47265(10) 0.35040(7) 0.0208(2) Uani 1 1 d . . . . .
H006 H 0.425037 0.451590 0.334478 0.025 Uiso 1 1 calc R U . . .
O007 O 0.95127(9) 0.53213(10) 0.08492(8) 0.0395(3) Uani 1 1 d . . . . .
O1 O 0.99450(8) 0.59302(14) 0.22836(8) 0.0481(3) Uani 1 1 d . . . . .
N009 N 0.93176(9) 0.55412(11) 0.15986(9) 0.0297(3) Uani 1 1 d . . . . .
C00A C 0.71246(9) 0.52904(10) 0.26462(8) 0.0176(2) Uani 1 1 d . . . . .
C00B C 0.80960(9) 0.54765(11) 0.25590(9) 0.0206(2) Uani 1 1 d . . . . .
H00B H 0.860858 0.568052 0.307692 0.025 Uiso 1 1 calc R U . . .
C00C C 0.55780(9) 0.37923(11) 0.37510(8) 0.0196(2) Uani 1 1 d . . . . .
C00D C 0.63708(9) 0.50125(11) 0.18474(8) 0.0206(2) Uani 1 1 d . . . . .
H00D H 0.571602 0.490254 0.189787 0.025 Uiso 1 1 calc R U . . .
C00E C 0.65604(9) 0.40677(11) 0.38605(8) 0.0182(2) Uani 1 1 d . . . . .
C00F C 0.60739(9) 0.63251(11) 0.36019(8) 0.0178(2) Uani 1 1 d . . . . .
C00G C 0.68814(9) 0.53555(11) 0.36000(8) 0.0172(2) Uani 1 1 d . . . . .
H00G H 0.749097 0.559938 0.406533 0.021 Uiso 1 1 calc R U . . .
C00H C 0.51032(9) 0.59743(11) 0.34968(8) 0.0193(2) Uani 1 1 d . . . . .
C00I C 0.77350(10) 0.89966(11) 0.35570(9) 0.0233(3) Uani 1 1 d . . . . .
H00A H 0.829824 0.918562 0.407837 0.028 Uiso 1 1 calc R U . . .
H00C H 0.721660 0.961409 0.354261 0.028 Uiso 1 1 calc R U . . .
C00J C 0.80622(9) 0.90383(12) 0.26619(9) 0.0236(3) Uani 1 1 d . . . . .
H00E H 0.841634 0.981119 0.262539 0.028 Uiso 1 1 calc R U . . .
H00F H 0.851403 0.835080 0.264155 0.028 Uiso 1 1 calc R U . . .
C00K C 0.73410(9) 0.31116(11) 0.41641(8) 0.0208(2) Uani 1 1 d . . . . .
C00L C 0.82878(10) 0.53523(12) 0.16847(9) 0.0232(3) Uani 1 1 d . . . . .
C00M C 0.51238(10) 0.25546(12) 0.38863(9) 0.0243(3) Uani 1 1 d . . . . .
H00H H 0.505860 0.249141 0.451638 0.036 Uiso 1 1 calc R U . . .
H00I H 0.554834 0.189665 0.376700 0.036 Uiso 1 1 calc R U . . .
H00J H 0.447408 0.248454 0.346197 0.036 Uiso 1 1 calc R U . . .
C00N C 0.63586(9) 0.76493(11) 0.36340(8) 0.0196(2) Uani 1 1 d . . . . .
C00O C 0.65822(10) 0.48976(12) 0.09793(9) 0.0253(3) Uani 1 1 d . . . . .
H00O H 0.606952 0.471426 0.045622 0.030 Uiso 1 1 calc R U . . .
C00P C 0.75530(11) 0.50550(12) 0.08897(9) 0.0258(3) Uani 1 1 d . . . . .
H00P H 0.770635 0.496405 0.031485 0.031 Uiso 1 1 calc R U . . .
C00Q C 0.41984(9) 0.68022(12) 0.33647(9) 0.0254(3) Uani 1 1 d . . . . .
H00K H 0.361872 0.636588 0.301228 0.038 Uiso 1 1 calc R U . . .
H00L H 0.430078 0.754146 0.303419 0.038 Uiso 1 1 calc R U . . .
H00M H 0.409749 0.702814 0.396321 0.038 Uiso 1 1 calc R U . . .
C00R C 0.91160(10) 0.27749(12) 0.46396(12) 0.0318(3) Uani 1 1 d . . . . .
H00R H 0.895422 0.193551 0.438520 0.038 Uiso 1 1 calc R U . . .
C00S C 0.74707(12) 0.88905(17) 0.10267(10) 0.0378(4) Uani 1 1 d . . . . .
H00N H 0.687295 0.887292 0.052765 0.057 Uiso 1 1 calc R U . . .
H00Q H 0.785414 0.814792 0.100675 0.057 Uiso 1 1 calc R U . . .
H00S H 0.786391 0.960755 0.095844 0.057 Uiso 1 1 calc R U . . .
C00T C 0.93295(13) 0.27377(16) 0.56894(13) 0.0449(4) Uani 1 1 d . . . . .
H00T H 0.947484 0.356433 0.593421 0.067 Uiso 1 1 calc R U . . .
H00U H 0.989542 0.220663 0.593136 0.067 Uiso 1 1 calc R U . . .
H00V H 0.875416 0.241855 0.587121 0.067 Uiso 1 1 calc R U . . .
C00U C 0.99744(12) 0.33067(15) 0.42919(16) 0.0488(5) Uani 1 1 d . . . . .
H00W H 0.980067 0.330389 0.362182 0.073 Uiso 1 1 calc R U . . .
H00X H 1.056313 0.280769 0.451946 0.073 Uiso 1 1 calc R U . . .
H00Y H 1.010444 0.414615 0.451377 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00I 1.4464(14) . ?
O001 C00N 1.3622(15) . ?
O002 C00K 1.3522(15) . ?
O002 C00R 1.4593(15) . ?
O003 C00J 1.4209(15) . ?
O003 C00S 1.4220(16) . ?
O004 C00K 1.2144(16) . ?
O005 C00N 1.2084(16) . ?
N006 H006 0.8600 . ?
N006 C00C 1.3804(16) . ?
N006 C00H 1.3765(16) . ?
O007 N009 1.2256(16) . ?
O1 N009 1.2302(17) . ?
N009 C00L 1.4680(17) . ?
C00A C00B 1.3888(17) . ?
C00A C00D 1.3980(17) . ?
C00A C00G 1.5292(15) . ?
C00B H00B 0.9300 . ?
C00B C00L 1.3880(17) . ?
C00C C00E 1.3540(17) . ?
C00C C00M 1.5018(17) . ?
C00D H00D 0.9300 . ?
C00D C00O 1.3896(17) . ?
C00E C00G 1.5285(16) . ?
C00E C00K 1.4728(16) . ?
C00F C00G 1.5227(16) . ?
C00F C00H 1.3594(17) . ?
C00F C00N 1.4713(16) . ?
C00G H00G 0.9800 . ?
C00H C00Q 1.5024(17) . ?
C00I H00A 0.9700 . ?
C00I H00C 0.9700 . ?
C00I C00J 1.5000(17) . ?
C00J H00E 0.9700 . ?
C00J H00F 0.9700 . ?
C00L C00P 1.3851(19) . ?
C00M H00H 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00J 0.9600 . ?
C00O H00O 0.9300 . ?
C00O C00P 1.3852(19) . ?
C00P H00P 0.9300 . ?
C00Q H00K 0.9600 . ?
C00Q H00L 0.9600 . ?
C00Q H00M 0.9600 . ?
C00R H00R 0.9800 . ?
C00R C00T 1.507(2) . ?
C00R C00U 1.512(2) . ?
C00S H00N 0.9600 . ?
C00S H00Q 0.9600 . ?
C00S H00S 0.9600 . ?
C00T H00T 0.9600 . ?
C00T H00U 0.9600 . ?
C00T H00V 0.9600 . ?
C00U H00W 0.9600 . ?
C00U H00X 0.9600 . ?
C00U H00Y 0.9600 . ?

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
C00N O001 C00I 117.98(9) . . ?
C00K O002 C00R 116.90(10) . . ?
C00J O003 C00S 112.08(10) . . ?
C00C N006 H006 118.0 . . ?
C00H N006 H006 118.0 . . ?
C00H N006 C00C 124.01(10) . . ?
O007 N009 O1 122.93(12) . . ?
O007 N009 C00L 118.92(12) . . ?
O1 N009 C00L 118.15(11) . . ?
C00B C00A C00D 118.86(11) . . ?
C00B C00A C00G 120.93(10) . . ?
C00D C00A C00G 120.19(10) . . ?
C00A C00B H00B 120.6 . . ?
C00L C00B C00A 118.78(11) . . ?
C00L C00B H00B 120.6 . . ?
N006 C00C C00M 112.85(10) . . ?
C00E C00C N006 119.32(11) . . ?
C00E C00C C00M 127.81(11) . . ?
C00A C00D H00D 119.4 . . ?
C00O C00D C00A 121.21(12) . . ?
C00O C00D H00D 119.4 . . ?
C00C C00E C00G 120.62(10) . . ?
C00C C00E C00K 121.08(11) . . ?
C00K C00E C00G 118.14(10) . . ?
C00H C00F C00G 120.52(11) . . ?
C00H C00F C00N 121.16(11) . . ?
C00N C00F C00G 118.09(10) . . ?
C00A C00G H00G 108.4 . . ?
C00E C00G C00A 109.50(9) . . ?
C00E C00G H00G 108.4 . . ?
C00F C00G C00A 111.04(9) . . ?
C00F C00G C00E 111.13(9) . . ?
C00F C00G H00G 108.4 . . ?
N006 C00H C00Q 112.98(11) . . ?
C00F C00H N006 119.37(11) . . ?
C00F C00H C00Q 127.65(11) . . ?
O001 C00I H00A 109.9 . . ?
O001 C00I H00C 109.9 . . ?
O001 C00I C00J 109.11(10) . . ?
H00A C00I H00C 108.3 . . ?
C00J C00I H00A 109.9 . . ?
C00J C00I H00C 109.9 . . ?
O003 C00J C00I 109.28(10) . . ?
O003 C00J H00E 109.8 . . ?
O003 C00J H00F 109.8 . . ?
C00I C00J H00E 109.8 . . ?
C00I C00J H00F 109.8 . . ?
H00E C00J H00F 108.3 . . ?
O002 C00K C00E 111.12(10) . . ?
O004 C00K O002 122.11(11) . . ?
O004 C00K C00E 126.76(12) . . ?
C00B C00L N009 118.50(12) . . ?
C00P C00L N009 118.45(11) . . ?
C00P C00L C00B 123.05(12) . . ?
C00C C00M H00H 109.5 . . ?
C00C C00M H00I 109.5 . . ?
C00C C00M H00J 109.5 . . ?
H00H C00M H00I 109.5 . . ?
H00H C00M H00J 109.5 . . ?
H00I C00M H00J 109.5 . . ?
O001 C00N C00F 110.29(10) . . ?
O005 C00N O001 122.18(11) . . ?
O005 C00N C00F 127.53(11) . . ?
C00D C00O H00O 119.9 . . ?
C00P C00O C00D 120.29(12) . . ?
C00P C00O H00O 119.9 . . ?
C00L C00P C00O 117.79(11) . . ?
C00L C00P H00P 121.1 . . ?
C00O C00P H00P 121.1 . . ?
C00H C00Q H00K 109.5 . . ?
C00H C00Q H00L 109.5 . . ?
C00H C00Q H00M 109.5 . . ?
H00K C00Q H00L 109.5 . . ?
H00K C00Q H00M 109.5 . . ?
H00L C00Q H00M 109.5 . . ?
O002 C00R H00R 109.8 . . ?
O002 C00R C00T 108.64(12) . . ?
O002 C00R C00U 105.71(12) . . ?
C00T C00R H00R 109.8 . . ?
C00T C00R C00U 112.96(14) . . ?
C00U C00R H00R 109.8 . . ?
O003 C00S H00N 109.5 . . ?
O003 C00S H00Q 109.5 . . ?
O003 C00S H00S 109.5 . . ?
H00N C00S H00Q 109.5 . . ?
H00N C00S H00S 109.5 . . ?
H00Q C00S H00S 109.5 . . ?
C00R C00T H00T 109.5 . . ?
C00R C00T H00U 109.5 . . ?
C00R C00T H00V 109.5 . . ?
H00T C00T H00U 109.5 . . ?
H00T C00T H00V 109.5 . . ?
H00U C00T H00V 109.5 . . ?
C00R C00U H00W 109.5 . . ?
C00R C00U H00X 109.5 . . ?
C00R C00U H00Y 109.5 . . ?
H00W C00U H00X 109.5 . . ?
H00W C00U H00Y 109.5 . . ?
H00X C00U H00Y 109.5 . . ?

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
O001 C00I C00J O003 68.55(13) . . . . ?
N006 C00C C00E C00G -7.44(17) . . . . ?
N006 C00C C00E C00K 177.26(10) . . . . ?
O007 N009 C00L C00B 173.31(12) . . . . ?
O007 N009 C00L C00P -6.51(19) . . . . ?
O1 N009 C00L C00B -7.58(19) . . . . ?
O1 N009 C00L C00P 172.60(13) . . . . ?
N009 C00L C00P C00O -179.07(11) . . . . ?
C00A C00B C00L N009 -179.56(11) . . . . ?
C00A C00B C00L C00P 0.26(19) . . . . ?
C00A C00D C00O C00P 0.15(19) . . . . ?
C00B C00A C00D C00O 1.24(18) . . . . ?
C00B C00A C00G C00E -113.81(12) . . . . ?
C00B C00A C00G C00F 123.10(12) . . . . ?
C00B C00L C00P C00O 1.11(19) . . . . ?
C00C N006 C00H C00F 10.18(18) . . . . ?
C00C N006 C00H C00Q -169.97(11) . . . . ?
C00C C00E C00G C00A -100.61(12) . . . . ?
C00C C00E C00G C00F 22.42(15) . . . . ?
C00C C00E C00K O002 -175.93(11) . . . . ?
C00C C00E C00K O004 4.3(2) . . . . ?
C00D C00A C00B C00L -1.42(17) . . . . ?
C00D C00A C00G C00E 64.70(13) . . . . ?
C00D C00A C00G C00F -58.38(14) . . . . ?
C00D C00O C00P C00L -1.30(19) . . . . ?
C00G C00A C00B C00L 177.12(10) . . . . ?
C00G C00A C00D C00O -177.31(11) . . . . ?
C00G C00E C00K O002 8.66(15) . . . . ?
C00G C00E C00K O004 -171.07(12) . . . . ?
C00G C00F C00H N006 7.97(17) . . . . ?
C00G C00F C00H C00Q -171.86(11) . . . . ?
C00G C00F C00N O001 -0.92(14) . . . . ?
C00G C00F C00N O005 179.05(12) . . . . ?
C00H N006 C00C C00E -10.43(18) . . . . ?
C00H N006 C00C C00M 168.33(11) . . . . ?
C00H C00F C00G C00A 99.49(12) . . . . ?
C00H C00F C00G C00E -22.66(15) . . . . ?
C00H C00F C00N O001 -175.42(10) . . . . ?
C00H C00F C00N O005 4.6(2) . . . . ?
C00I O001 C00N O005 -9.66(17) . . . . ?
C00I O001 C00N C00F 170.31(10) . . . . ?
C00K O002 C00R C00T -84.61(14) . . . . ?
C00K O002 C00R C00U 153.89(13) . . . . ?
C00K C00E C00G C00A 74.82(13) . . . . ?
C00K C00E C00G C00F -162.15(10) . . . . ?
C00M C00C C00E C00G 174.00(11) . . . . ?
C00M C00C C00E C00K -1.30(19) . . . . ?
C00N O001 C00I C00J -113.35(11) . . . . ?
C00N C00F C00G C00A -75.05(13) . . . . ?
C00N C00F C00G C00E 162.81(10) . . . . ?
C00N C00F C00H N006 -177.66(10) . . . . ?
C00N C00F C00H C00Q 2.50(19) . . . . ?
C00R O002 C00K O004 -3.65(18) . . . . ?
C00R O002 C00K C00E 176.60(11) . . . . ?
C00S O003 C00J C00I -175.40(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.617
_oxdiff_exptl_absorpt_empirical_full_min 0.583
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Vildagliptin-100k-HWRong
_database_code_depnum_ccdc_archive 'CCDC 1987348'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2020-01-02
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Vildagliptin
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H25 N3 O2'
_chemical_formula_sum            'C17 H26 N3 O2'
_chemical_formula_weight         304.41
_chemical_absolute_configuration ad
_chemical_melting_point          428K
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'
O O 0.0492 0.0322 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.14270(10)
_cell_length_b                   10.60440(10)
_cell_length_c                   14.51410(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1561.10(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11987
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.7290
_cell_measurement_theta_min      5.1370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14740
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.016
_diffrn_reflns_theta_min         5.166
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  26.00   0.50    0.05    --  -46.62  57.00   0.00  178
  2  ω     74.00 120.00   0.50    0.05    --   46.62 127.00  58.00   92
  3  ω     87.00 178.00   0.50    0.11    --  105.44  13.00  -4.00  182
  4  ω     33.00 117.00   0.50    0.11    --  105.44-125.00  60.00  168
  5  ω     15.00  95.00   0.50    0.05    --   46.62-125.00-150.00  160
  6  ω   -112.00 -27.00   0.50    0.11    -- -100.00 116.00 155.00  170
  7  ω   -117.00 -27.00   0.50    0.11    -- -100.00  61.00 -30.00  180
  8  ω   -119.00 -30.00   0.50    0.05    --  -46.62 -57.00  60.00  178
  9  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00  30.00  192
 10  ω   -123.00 -28.00   0.50    0.05    --  -46.62 -13.00-176.00  190
 11  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00-180.00  192
 12  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00 -30.00  192
 13  ω   -124.00 -27.00   0.50    0.11    -- -100.00  77.00 -30.00  194
 14  ω   -173.00 -70.00   0.50    0.11    -- -100.00-127.00 -17.00  206
 15  ω   -173.00 -82.00   0.50    0.11    -- -100.00 -61.00-180.00  182
 16  ω   -172.00-135.00   0.50    0.11    -- -100.00 -45.00  90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0002758000
_diffrn_orient_matrix_UB_12      -0.0507122000
_diffrn_orient_matrix_UB_13      -0.0994573000
_diffrn_orient_matrix_UB_21      0.0256063000
_diffrn_orient_matrix_UB_22      0.1342618000
_diffrn_orient_matrix_UB_23      -0.0365362000
_diffrn_orient_matrix_UB_31      0.1496417000
_diffrn_orient_matrix_UB_32      -0.0228911000
_diffrn_orient_matrix_UB_33      0.0064125000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                2938
_reflns_number_total             3087
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 1184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.086
_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)+(0.0648P)²+0.2077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C00C(H00G), C00G(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00A(H00C,H00D), C00B(H00E,H00F), C00D(H00H,H00I), C00E(H00J,
 H00K), C00H(H00M,H00N), C00I(H00O,H00P), C00J(H00Q,H00R), C00K(H00S,H00T),
 C00M(H00U,H00V)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.91347(15) 0.21996(13) 0.25902(10) 0.0243(3) Uani 1 1 d . . . . .
O002 O 0.81501(16) 0.44394(15) 0.68809(9) 0.0253(3) Uani 1 1 d . . . . .
H002 H 0.796672 0.488748 0.732317 0.038 Uiso 1 1 calc R U . . .
N003 N 0.76019(17) 0.06519(16) 0.26127(11) 0.0207(4) Uani 1 1 d . . . . .
N004 N 0.7650(2) 0.38733(17) 0.35195(12) 0.0227(4) Uani 1 1 d . . . . .
H004 H 0.856(3) 0.382(3) 0.3468(18) 0.027 Uiso 1 1 d . U . . .
C005 C 0.8063(2) 0.18038(19) 0.28515(13) 0.0199(4) Uani 1 1 d . . . . .
N006 N 0.8079(2) -0.0184(2) 0.03473(14) 0.0372(5) Uani 1 1 d . . . . .
C007 C 0.6078(2) 0.5037(2) 0.61574(14) 0.0223(4) Uani 1 1 d . . . . .
H00A H 0.585241 0.558066 0.667113 0.027 Uiso 1 1 calc R U . . .
H00B H 0.572320 0.420452 0.628024 0.027 Uiso 1 1 calc R U . . .
C008 C 0.7528(2) 0.68130(18) 0.49924(14) 0.0232(4) Uani 1 1 d . . . . .
H008 H 0.788292 0.765752 0.487539 0.028 Uiso 1 1 calc R U . . .
C009 C 0.7574(2) 0.4959(2) 0.60626(13) 0.0204(4) Uani 1 1 d . . . . .
C00A C 0.6398(2) 0.0040(2) 0.29744(15) 0.0244(4) Uani 1 1 d . . . . .
H00C H 0.561044 0.045024 0.274285 0.029 Uiso 1 1 calc R U . . .
H00D H 0.638381 0.005507 0.364253 0.029 Uiso 1 1 calc R U . . .
C00B C 0.8133(2) 0.62741(19) 0.58772(13) 0.0220(4) Uani 1 1 d . . . . .
H00E H 0.908370 0.622595 0.581326 0.026 Uiso 1 1 calc R U . . .
H00F H 0.793419 0.682555 0.639202 0.026 Uiso 1 1 calc R U . . .
C00C C 0.5474(2) 0.5562(2) 0.52688(14) 0.0236(5) Uani 1 1 d . . . . .
H00G H 0.451405 0.560831 0.533469 0.028 Uiso 1 1 calc R U . . .
C00D C 0.7179(2) 0.25743(19) 0.34842(14) 0.0230(4) Uani 1 1 d . . . . .
H00H H 0.627972 0.255693 0.325614 0.028 Uiso 1 1 calc R U . . .
H00I H 0.718540 0.221305 0.409814 0.028 Uiso 1 1 calc R U . . .
C00E C 0.5822(2) 0.4692(2) 0.44599(14) 0.0230(4) Uani 1 1 d . . . . .
H00J H 0.546622 0.385625 0.457052 0.028 Uiso 1 1 calc R U . . .
H00K H 0.543311 0.501636 0.389743 0.028 Uiso 1 1 calc R U . . .
C00F C 0.7321(2) 0.46126(18) 0.43512(13) 0.0201(4) Uani 1 1 d . . . . .
C00G C 0.8452(2) -0.02490(18) 0.21349(14) 0.0213(4) Uani 1 1 d . . . . .
H00L H 0.937999 -0.010116 0.229007 0.026 Uiso 1 1 calc R U . . .
C00H C 0.7872(2) 0.59366(19) 0.41883(13) 0.0227(4) Uani 1 1 d . . . . .
H00M H 0.750877 0.627648 0.362214 0.027 Uiso 1 1 calc R U . . .
H00N H 0.882232 0.589145 0.412056 0.027 Uiso 1 1 calc R U . . .
C00I C 0.7924(2) 0.40881(19) 0.52564(13) 0.0202(4) Uani 1 1 d . . . . .
H00O H 0.758373 0.324842 0.537348 0.024 Uiso 1 1 calc R U . . .
H00P H 0.887454 0.403092 0.519574 0.024 Uiso 1 1 calc R U . . .
C00J C 0.6504(2) -0.13111(19) 0.26132(15) 0.0240(4) Uani 1 1 d . . . . .
H00Q H 0.612307 -0.190563 0.304569 0.029 Uiso 1 1 calc R U . . .
H00R H 0.606345 -0.139781 0.202346 0.029 Uiso 1 1 calc R U . . .
C00K C 0.7989(2) -0.1518(2) 0.25160(15) 0.0250(5) Uani 1 1 d . . . . .
H00S H 0.818100 -0.219990 0.209095 0.030 Uiso 1 1 calc R U . . .
H00T H 0.839356 -0.169977 0.310674 0.030 Uiso 1 1 calc R U . . .
C00L C 0.8250(2) -0.0182(2) 0.11271(15) 0.0240(4) Uani 1 1 d . . . . .
C00M C 0.6026(2) 0.6882(2) 0.50972(15) 0.0260(5) Uani 1 1 d . . . . .
H00U H 0.580154 0.742946 0.560902 0.031 Uiso 1 1 calc R U . . .
H00V H 0.563922 0.723160 0.454192 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.225(3) . ?
O002 H002 0.8200 . ?
O002 C009 1.434(2) . ?
N003 C005 1.353(3) . ?
N003 C00A 1.479(3) . ?
N003 C00G 1.462(3) . ?
N004 H004 0.92(3) . ?
N004 C00D 1.459(3) . ?
N004 C00F 1.478(2) . ?
C005 C00D 1.522(3) . ?
N006 C00L 1.145(3) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C009 1.526(3) . ?
C007 C00C 1.532(3) . ?
C008 H008 0.9800 . ?
C008 C00B 1.534(3) . ?
C008 C00H 1.532(3) . ?
C008 C00M 1.533(3) . ?
C009 C00B 1.529(3) . ?
C009 C00I 1.532(3) . ?
C00A H00C 0.9700 . ?
C00A H00D 0.9700 . ?
C00A C00J 1.529(3) . ?
C00B H00E 0.9700 . ?
C00B H00F 0.9700 . ?
C00C H00G 0.9800 . ?
C00C C00E 1.534(3) . ?
C00C C00M 1.528(3) . ?
C00D H00H 0.9700 . ?
C00D H00I 0.9700 . ?
C00E H00J 0.9700 . ?
C00E H00K 0.9700 . ?
C00E C00F 1.531(3) . ?
C00F C00H 1.529(3) . ?
C00F C00I 1.552(3) . ?
C00G H00L 0.9800 . ?
C00G C00K 1.529(3) . ?
C00G C00L 1.479(3) . ?
C00H H00M 0.9700 . ?
C00H H00N 0.9700 . ?
C00I H00O 0.9700 . ?
C00I H00P 0.9700 . ?
C00J H00Q 0.9700 . ?
C00J H00R 0.9700 . ?
C00J C00K 1.528(3) . ?
C00K H00S 0.9700 . ?
C00K H00T 0.9700 . ?
C00M H00U 0.9700 . ?
C00M H00V 0.9700 . ?

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
C009 O002 H002 109.5 . . ?
C005 N003 C00A 126.21(18) . . ?
C005 N003 C00G 120.48(17) . . ?
C00G N003 C00A 111.62(17) . . ?
C00D N004 H004 105.2(17) . . ?
C00D N004 C00F 117.10(17) . . ?
C00F N004 H004 109.0(17) . . ?
O001 C005 N003 122.46(19) . . ?
O001 C005 C00D 121.73(18) . . ?
N003 C005 C00D 115.80(18) . . ?
H00A C007 H00B 108.2 . . ?
C009 C007 H00A 109.7 . . ?
C009 C007 H00B 109.7 . . ?
C009 C007 C00C 109.96(16) . . ?
C00C C007 H00A 109.7 . . ?
C00C C007 H00B 109.7 . . ?
C00B C008 H008 109.8 . . ?
C00H C008 H008 109.8 . . ?
C00H C008 C00B 108.71(17) . . ?
C00H C008 C00M 109.32(17) . . ?
C00M C008 H008 109.8 . . ?
C00M C008 C00B 109.41(17) . . ?
O002 C009 C007 110.56(16) . . ?
O002 C009 C00B 110.20(16) . . ?
O002 C009 C00I 107.86(16) . . ?
C007 C009 C00B 109.57(18) . . ?
C007 C009 C00I 109.38(17) . . ?
C00B C009 C00I 109.24(15) . . ?
N003 C00A H00C 111.1 . . ?
N003 C00A H00D 111.1 . . ?
N003 C00A C00J 103.38(17) . . ?
H00C C00A H00D 109.1 . . ?
C00J C00A H00C 111.1 . . ?
C00J C00A H00D 111.1 . . ?
C008 C00B H00E 109.7 . . ?
C008 C00B H00F 109.7 . . ?
C009 C00B C008 109.80(16) . . ?
C009 C00B H00E 109.7 . . ?
C009 C00B H00F 109.7 . . ?
H00E C00B H00F 108.2 . . ?
C007 C00C H00G 109.5 . . ?
C007 C00C C00E 109.49(17) . . ?
C00E C00C H00G 109.5 . . ?
C00M C00C C007 108.88(17) . . ?
C00M C00C H00G 109.5 . . ?
C00M C00C C00E 110.00(17) . . ?
N004 C00D C005 109.55(17) . . ?
N004 C00D H00H 109.8 . . ?
N004 C00D H00I 109.8 . . ?
C005 C00D H00H 109.8 . . ?
C005 C00D H00I 109.8 . . ?
H00H C00D H00I 108.2 . . ?
C00C C00E H00J 109.7 . . ?
C00C C00E H00K 109.7 . . ?
H00J C00E H00K 108.2 . . ?
C00F C00E C00C 109.89(17) . . ?
C00F C00E H00J 109.7 . . ?
C00F C00E H00K 109.7 . . ?
N004 C00F C00E 109.73(17) . . ?
N004 C00F C00H 106.16(16) . . ?
N004 C00F C00I 114.36(17) . . ?
C00E C00F C00I 108.88(17) . . ?
C00H C00F C00E 109.18(16) . . ?
C00H C00F C00I 108.42(16) . . ?
N003 C00G H00L 110.7 . . ?
N003 C00G C00K 102.84(16) . . ?
N003 C00G C00L 110.84(17) . . ?
C00K C00G H00L 110.7 . . ?
C00L C00G H00L 110.7 . . ?
C00L C00G C00K 110.93(17) . . ?
C008 C00H H00M 109.5 . . ?
C008 C00H H00N 109.5 . . ?
C00F C00H C008 110.85(16) . . ?
C00F C00H H00M 109.5 . . ?
C00F C00H H00N 109.5 . . ?
H00M C00H H00N 108.1 . . ?
C009 C00I C00F 109.83(16) . . ?
C009 C00I H00O 109.7 . . ?
C009 C00I H00P 109.7 . . ?
C00F C00I H00O 109.7 . . ?
C00F C00I H00P 109.7 . . ?
H00O C00I H00P 108.2 . . ?
C00A C00J H00Q 111.0 . . ?
C00A C00J H00R 111.0 . . ?
H00Q C00J H00R 109.0 . . ?
C00K C00J C00A 103.63(17) . . ?
C00K C00J H00Q 111.0 . . ?
C00K C00J H00R 111.0 . . ?
C00G C00K H00S 111.3 . . ?
C00G C00K H00T 111.3 . . ?
C00J C00K C00G 102.11(16) . . ?
C00J C00K H00S 111.3 . . ?
C00J C00K H00T 111.3 . . ?
H00S C00K H00T 109.2 . . ?
N006 C00L C00G 177.1(2) . . ?
C008 C00M H00U 109.7 . . ?
C008 C00M H00V 109.7 . . ?
C00C C00M C008 109.66(17) . . ?
C00C C00M H00U 109.7 . . ?
C00C C00M H00V 109.7 . . ?
H00U C00M H00V 108.2 . . ?

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
O001 C005 C00D N004 13.5(3) . . . . ?
O002 C009 C00B C008 179.09(16) . . . . ?
O002 C009 C00I C00F -179.97(16) . . . . ?
N003 C005 C00D N004 -167.70(17) . . . . ?
N003 C00A C00J C00K 27.7(2) . . . . ?
N003 C00G C00K C00J 36.6(2) . . . . ?
N004 C00F C00H C008 177.21(17) . . . . ?
N004 C00F C00I C009 177.35(17) . . . . ?
C005 N003 C00A C00J -169.72(18) . . . . ?
C005 N003 C00G C00K 145.87(18) . . . . ?
C005 N003 C00G C00L -95.5(2) . . . . ?
C007 C009 C00B C008 -59.0(2) . . . . ?
C007 C009 C00I C00F 59.7(2) . . . . ?
C007 C00C C00E C00F -60.0(2) . . . . ?
C007 C00C C00M C008 60.4(2) . . . . ?
C009 C007 C00C C00E 59.9(2) . . . . ?
C009 C007 C00C C00M -60.4(2) . . . . ?
C00A N003 C005 O001 172.76(19) . . . . ?
C00A N003 C005 C00D -6.1(3) . . . . ?
C00A N003 C00G C00K -20.2(2) . . . . ?
C00A N003 C00G C00L 98.4(2) . . . . ?
C00A C00J C00K C00G -39.96(19) . . . . ?
C00B C008 C00H C00F 60.2(2) . . . . ?
C00B C008 C00M C00C -60.1(2) . . . . ?
C00B C009 C00I C00F -60.2(2) . . . . ?
C00C C007 C009 O002 -178.54(16) . . . . ?
C00C C007 C009 C00B 59.8(2) . . . . ?
C00C C007 C009 C00I -59.9(2) . . . . ?
C00C C00E C00F N004 -174.65(16) . . . . ?
C00C C00E C00F C00H -58.7(2) . . . . ?
C00C C00E C00F C00I 59.5(2) . . . . ?
C00D N004 C00F C00E -59.6(2) . . . . ?
C00D N004 C00F C00H -177.44(17) . . . . ?
C00D N004 C00F C00I 63.1(2) . . . . ?
C00E C00C C00M C008 -59.6(2) . . . . ?
C00E C00F C00H C008 59.0(2) . . . . ?
C00E C00F C00I C009 -59.5(2) . . . . ?
C00F N004 C00D C005 -154.73(17) . . . . ?
C00G N003 C005 O001 8.8(3) . . . . ?
C00G N003 C005 C00D -169.99(17) . . . . ?
C00G N003 C00A C00J -4.6(2) . . . . ?
C00H C008 C00B C009 -60.2(2) . . . . ?
C00H C008 C00M C00C 58.9(2) . . . . ?
C00H C00F C00I C009 59.1(2) . . . . ?
C00I C009 C00B C008 60.8(2) . . . . ?
C00I C00F C00H C008 -59.5(2) . . . . ?
C00L C00G C00K C00J -82.0(2) . . . . ?
C00M C008 C00B C009 59.2(2) . . . . ?
C00M C008 C00H C00F -59.1(2) . . . . ?
C00M C00C C00E C00F 59.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.734
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_MetforminHydrochloride-100k-HWRong
_database_code_depnum_ccdc_archive 'CCDC 1987347'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-31
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Metformin
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C4 H11 N5'
_chemical_formula_sum            'C4 H11 Cl N5'
_chemical_formula_weight         164.63
_chemical_melting_point          511K
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'
Cl Cl 0.3639 0.7018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9234(2)
_cell_length_b                   13.8743(2)
_cell_length_c                   7.9286(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.547(2)
_cell_angle_gamma                90
_cell_volume                     792.83(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6615
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9410
_cell_measurement_theta_min      6.1010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7387
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.947
_diffrn_reflns_theta_min         6.140
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  63.00   0.50    0.05    --   46.62 -57.00 106.00  176
  2  ω     88.00 178.00   0.50    0.08    --  105.44  15.00  30.00  180
  3  ω     88.00 158.00   0.50    0.08    --  105.44  15.00 -60.00  140
  4  ω     76.00 178.00   0.50    0.08    --  105.44 125.00-180.00  204
  5  ω     32.00 120.00   0.50    0.05    --   46.62  38.00-120.00  176
  6  ω     31.00 120.00   0.50    0.05    --   46.62  57.00 -30.00  178
  7  ω     33.00 108.00   0.50    0.08    --  105.44 -94.00  90.00  150
  8  ω     33.00 108.00   0.50    0.08    --  105.44 -94.00 150.00  150
  9  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00 -90.00   96
 10  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00-120.00   96
 11  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00  30.00  192
 12  ω   -118.00 -27.00   0.50    0.08    -- -100.00  64.00  78.00  182
 13  ω   -119.00 -30.00   0.50    0.05    --  -46.62 -57.00 106.00  178
 14  ω   -124.00 -27.00   0.50    0.08    -- -100.00  77.00 -60.00  194
 15  ω   -173.00 -74.00   0.50    0.08    -- -100.00-121.00-126.00  198
 16  ω   -173.00 -84.00   0.50    0.08    -- -100.00 -57.00 106.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2064236000
_diffrn_orient_matrix_UB_12      -0.0095414000
_diffrn_orient_matrix_UB_13      0.0378672000
_diffrn_orient_matrix_UB_21      0.0117539000
_diffrn_orient_matrix_UB_22      0.1099386000
_diffrn_orient_matrix_UB_23      -0.0204957000
_diffrn_orient_matrix_UB_31      0.0543825000
_diffrn_orient_matrix_UB_32      0.0125230000
_diffrn_orient_matrix_UB_33      0.2091063000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1530
_reflns_number_total             1580
_reflns_odcompleteness_completeness 98.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.032
_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)+(0.0665P)²+1.1583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002)
2.b X=CH2 refined with riding coordinates:
 N003(H00A,H00B)
2.c Idealised Me refined as rotating group:
 C009(H00C,H00D,H00E), C00A(H00F,H00G,H00H)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl01 Cl 1.15556(6) 0.51546(3) 0.77615(6) 0.01387(19) Uani 1 1 d . . . . .
N002 N 0.6249(2) 0.27205(12) 0.7020(2) 0.0118(4) Uani 1 1 d . . . . .
H002 H 0.644907 0.250584 0.810385 0.014 Uiso 1 1 calc R U . . .
N003 N 0.8388(2) 0.39165(12) 0.8366(2) 0.0158(4) Uani 1 1 d . . . . .
H00A H 0.830146 0.381345 0.939663 0.019 Uiso 1 1 calc R U . . .
H00B H 0.912533 0.435518 0.829990 0.019 Uiso 1 1 calc R U . . .
N004 N 0.7623(2) 0.35413(13) 0.5313(2) 0.0143(4) Uani 1 1 d . . . . .
H004 H 0.820(4) 0.393(2) 0.522(4) 0.017 Uiso 1 1 d . U . . .
N005 N 0.3502(2) 0.29301(12) 0.4303(2) 0.0129(4) Uani 1 1 d . . . . .
N006 N 0.4605(3) 0.14045(12) 0.5418(3) 0.0155(4) Uani 1 1 d . . . . .
H006 H 0.550(4) 0.107(2) 0.606(4) 0.019 Uiso 1 1 d . U . . .
C007 C 0.7376(3) 0.33941(14) 0.6864(3) 0.0116(4) Uani 1 1 d . . . . .
C008 C 0.4800(3) 0.23626(14) 0.5531(3) 0.0121(4) Uani 1 1 d . . . . .
C009 C 0.3426(3) 0.39671(14) 0.4585(3) 0.0177(4) Uani 1 1 d . . . . .
H00C H 0.417161 0.412079 0.586064 0.027 Uiso 1 1 calc R U . . .
H00D H 0.216482 0.415594 0.426728 0.027 Uiso 1 1 calc R U . . .
H00E H 0.389137 0.430585 0.381046 0.027 Uiso 1 1 calc R U . . .
C00A C 0.1910(3) 0.25385(16) 0.2724(3) 0.0173(4) Uani 1 1 d . . . . .
H00F H 0.226338 0.195028 0.232044 0.026 Uiso 1 1 calc R U . . .
H00G H 0.150303 0.299697 0.172738 0.026 Uiso 1 1 calc R U . . .
H00H H 0.091761 0.241124 0.308922 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N002 H002 0.8600 . ?
N002 C007 1.333(3) . ?
N002 C008 1.353(3) . ?
N003 H00A 0.8600 . ?
N003 H00B 0.8600 . ?
N003 C007 1.339(3) . ?
N004 H004 0.73(3) . ?
N004 C007 1.339(3) . ?
N005 C008 1.339(3) . ?
N005 C009 1.461(3) . ?
N005 C00A 1.464(3) . ?
N006 H006 0.82(3) . ?
N006 C008 1.337(3) . ?
C009 H00C 0.9600 . ?
C009 H00D 0.9600 . ?
C009 H00E 0.9600 . ?
C00A H00F 0.9600 . ?
C00A H00G 0.9600 . ?
C00A H00H 0.9600 . ?

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 N002 H002 118.8 . . ?
C007 N002 C008 122.31(17) . . ?
C008 N002 H002 118.8 . . ?
H00A N003 H00B 120.0 . . ?
C007 N003 H00A 120.0 . . ?
C007 N003 H00B 120.0 . . ?
C007 N004 H004 123(2) . . ?
C008 N005 C009 122.41(17) . . ?
C008 N005 C00A 122.16(17) . . ?
C009 N005 C00A 114.87(16) . . ?
C008 N006 H006 118.0(19) . . ?
N002 C007 N003 118.31(18) . . ?
N002 C007 N004 123.42(18) . . ?
N004 C007 N003 118.18(18) . . ?
N005 C008 N002 122.36(18) . . ?
N006 C008 N002 117.10(18) . . ?
N006 C008 N005 120.23(18) . . ?
N005 C009 H00C 109.5 . . ?
N005 C009 H00D 109.5 . . ?
N005 C009 H00E 109.5 . . ?
H00C C009 H00D 109.5 . . ?
H00C C009 H00E 109.5 . . ?
H00D C009 H00E 109.5 . . ?
N005 C00A H00F 109.5 . . ?
N005 C00A H00G 109.5 . . ?
N005 C00A H00H 109.5 . . ?
H00F C00A H00G 109.5 . . ?
H00F C00A H00H 109.5 . . ?
H00G C00A H00H 109.5 . . ?

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
C007 N002 C008 N005 -53.6(3) . . . . ?
C007 N002 C008 N006 132.7(2) . . . . ?
C008 N002 C007 N003 159.82(18) . . . . ?
C008 N002 C007 N004 -23.8(3) . . . . ?
C009 N005 C008 N002 -7.2(3) . . . . ?
C009 N005 C008 N006 166.26(19) . . . . ?
C00A N005 C008 N002 -178.21(18) . . . . ?
C00A N005 C008 N006 -4.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.738
_oxdiff_exptl_absorpt_empirical_full_min 0.747
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Celecoxib-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987512'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Celecoxib
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 F3 N3 O2 S'
_chemical_formula_sum            'C17 H14 F3 N3 O2 S'
_chemical_formula_weight         381.37
_chemical_melting_point          436K
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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   5.06400(10)
_cell_length_b                   10.01390(10)
_cell_length_c                   16.40730(10)
_cell_angle_alpha                89.8820(10)
_cell_angle_beta                 85.8650(10)
_cell_angle_gamma                80.5380(10)
_cell_volume                     818.524(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24344
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9500
_cell_measurement_theta_min      2.7020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.107
_diffrn_reflns_theta_min         2.700
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00 122.00   0.50    0.05    --   46.37  19.00 -90.00  182
  2  ω     65.00  91.00   0.50    0.05    --   80.00  71.00   1.35   52
  3  ω     60.00  86.00   0.50    0.05    --   84.00  82.00 -50.78   52
  4  ω     64.00 118.00   0.50    0.05    --   46.37 143.00   9.00  108
  5  ω     64.00 175.00   0.50    0.05    --  105.44 143.00   9.00  222
  6  ω     74.00 178.00   0.50    0.05    --  105.44 127.00-159.00  208
  7  ω     81.00 107.00   0.50    0.05    --  105.44 -45.00  90.00   52
  8  ω     38.00  79.00   0.50    0.05    --  105.44 -45.00  90.00   82
  9  ω     16.00  96.00   0.50    0.05    --   46.37-127.00 124.00  160
 10  ω     33.00 118.00   0.50    0.05    --  105.44-127.00 124.00  170
 11  ω     25.00 106.00   0.50    0.05    --   46.37-143.00 -44.00  162
 12  ω     33.00 130.00   0.50    0.05    --  105.44-143.00 -44.00  194
 13  ω     33.00 106.00   0.50    0.05    --  105.44 -94.00 -30.00  146
 14  ω     32.00 120.00   0.50    0.05    --   46.37  38.00 120.00  176
 15  ω     39.00  65.00   0.50    0.05    --   64.00  79.00 172.52   52
 16  ω     24.00 121.00   0.50    0.05    --   48.00  78.00 129.92  194
 17  ω     30.00 118.00   0.50    0.05    --   46.37  57.00 -60.00  176
 18  ω     36.00 132.00   0.50    0.05    --   60.00  77.00 -23.59  192
 19  ω     39.00 132.00   0.50    0.05    --   60.00  71.00-111.06  186
 20  ω     32.00 120.00   0.50    0.05    --   46.37  38.00 -90.00  176
 21  ω     34.00 129.00   0.50    0.05    --   56.00  73.00-100.10  190
 22  ω     23.00 118.00   0.50    0.05    --   46.37  77.00   0.00  190
 23  ω     23.00 118.00   0.50    0.05    --   46.37  77.00  60.00  190
 24  ω     31.00 125.00   0.50    0.05    --   52.00  70.00 103.45  188
 25  ω     33.00 129.00   0.50    0.05    --   56.00  76.00 -72.86  192
 26  ω     23.00 118.00   0.50    0.05    --   46.37  77.00-180.00  190
 27  ω     -3.00  24.00   0.50    0.05    --   32.00 100.00 -50.70   54
 28  ω    -39.00 -13.00   0.50    0.05    --   12.00 129.00 -53.62   52
 29  ω    -96.00 -12.00   0.50    0.05    --  -46.37 127.00-159.00  168
 30  ω    -59.00 -31.00   0.50    0.05    -- -100.00  61.00  60.00   56
 31  ω   -100.00 -66.00   0.50    0.05    -- -100.00  61.00  60.00   68
 32  ω   -113.00 -27.00   0.50    0.05    -- -100.00  45.00  60.00  172
 33  ω   -105.00 -20.00   0.50    0.05    --  -46.37 143.00   9.00  170
 34  ω   -103.00 -78.00   0.50    0.05    -- -100.00 143.00   9.00   50
 35  ω   -115.00 -29.00   0.50    0.05    -- -100.00  61.00-120.00  172
 36  ω   -118.00 -27.00   0.50    0.05    -- -100.00 127.00-159.00  182
 37  ω    -87.00 -61.00   0.50    0.05    --  -76.00 -57.00 -20.88   52
 38  ω    -80.00 -54.00   0.50    0.05    --  -80.00 -82.00 -33.81   52
 39  ω    -67.00 -41.00   0.50    0.05    --  -64.00 -76.00 -75.65   52
 40  ω    -70.00 -44.00   0.50    0.05    --  -64.00 -68.00-116.04   52
 41  ω    -73.00 -47.00   0.50    0.05    --  -64.00 -65.00-141.10   52
 42  ω    -73.00 -47.00   0.50    0.05    --  -68.00 -79.00-159.48   52
 43  ω    -80.00 -54.00   0.50    0.05    --  -76.00 -72.00 -81.02   52
 44  ω    -83.00 -57.00   0.50    0.05    --  -80.00 -76.00-116.61   52
 45  ω    -95.00 -69.00   0.50    0.05    --  -84.00 -59.00-106.65   52
 46  ω   -101.00 -73.00   0.50    0.05    --  -88.00 -55.00 -29.51   56
 47  ω    -95.00 -50.00   0.50    0.05    --  -68.00 -62.00  26.21   90
 48  ω    -81.00 -55.00   0.50    0.05    --  -72.00 -61.00  41.68   52
 49  ω    -86.00 -60.00   0.50    0.05    --  -76.00 -60.00  55.48   52
 50  ω    -76.00 -50.00   0.50    0.05    --  -76.00 -81.00  48.70   52
 51  ω    -69.00 -39.00   0.50    0.05    --  -64.00 -81.00 128.81   60
 52  ω    -74.00 -48.00   0.50    0.05    --  -68.00 -68.00 155.08   52
 53  ω    -72.00 -46.00   0.50    0.05    --  -72.00 -83.00 162.30   52
 54  ω    -87.00 -53.00   0.50    0.05    --  -76.00 -76.00  95.11   68
 55  ω    -95.00 -56.00   0.50    0.05    --  -80.00 -78.00  29.13   78
 56  ω   -104.00 -74.00   0.50    0.05    --  -92.00 -63.00  71.54   60
 57  ω   -101.00 -76.00   0.50    0.05    -- -100.00 -77.00 120.00   50
 58  ω    -88.00 -62.00   0.50    0.05    --  -84.00 -72.00 146.09   52
 59  ω    -92.00 -66.00   0.50    0.05    --  -84.00 -65.00 147.74   52
 60  ω    -96.00 -70.00   0.50    0.05    --  -84.00 -61.00 168.18   52
 61  ω    -97.00 -71.00   0.50    0.05    --  -88.00 -59.00 177.88   52
 62  ω    -97.00 -71.00   0.50    0.05    --  -88.00 -62.00 158.43   52
 63  ω   -102.00 -73.00   0.50    0.05    --  -96.00 -76.00 146.49   58
 64  ω   -102.00 -76.00   0.50    0.05    -- -100.00 -77.00  90.00   52
 65  ω   -120.00 -78.00   0.50    0.05    -- -100.00 -74.00 172.02   84
 66  ω   -114.00 -84.00   0.50    0.05    -- -100.00 -64.00  89.70   60
 67  ω   -112.00 -76.00   0.50    0.05    -- -100.00 -77.00  30.00   72
 68  ω   -111.00 -72.00   0.50    0.05    --  -96.00 -77.00 -27.92   78
 69  ω   -109.00 -76.00   0.50    0.05    -- -100.00 -77.00 -60.00   66
 70  ω   -101.00 -76.00   0.50    0.05    -- -100.00 -77.00-120.00   50
 71  ω   -108.00 -81.00   0.50    0.05    -- -100.00 -72.00-178.91   54
 72  ω   -124.00 -75.00   0.50    0.05    --  -92.00 -59.00-161.93   98
 73  ω   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00-150.00  190
 74  ω   -118.00 -59.00   0.50    0.05    --  -46.37-143.00 -44.00  118
 75  ω   -121.00 -77.00   0.50    0.05    --  -92.00 -57.00-112.04   88
 76  ω   -132.00 -35.00   0.50    0.05    --  -60.00 -80.00 -93.63  194
 77  ω   -124.00 -78.00   0.50    0.05    -- -100.00 -72.00  31.31   92
 78  ω   -118.00 -70.00   0.50    0.05    --  -46.37-127.00 124.00   96
 79  ω   -133.00 -84.00   0.50    0.05    -- -100.00 -59.00 115.49   98
 80  ω   -148.00-110.00   0.50    0.05    --  -88.00 -55.00 -29.51   76
 81  ω   -153.00 -75.00   0.50    0.05    -- -100.00 -79.00 -46.29  156
 82  ω   -132.00 -35.00   0.50    0.05    --  -60.00 -80.00-178.29  194
 83  ω   -164.00-115.00   0.50    0.05    --  -92.00 -63.00  71.54   98
 84  ω   -169.00-110.00   0.50    0.05    --  -96.00 -76.00 146.49  118
 85  ω   -173.00 -70.00   0.50    0.05    -- -100.00-127.00 124.00  206
 86  ω   -173.00 -59.00   0.50    0.05    -- -100.00-143.00 -44.00  228
 87  ω   -163.00-131.00   0.50    0.05    --  -92.00 -59.00-161.93   64
 88  ω   -157.00 -82.00   0.50    0.05    -- -100.00 -61.00-180.00  150
 89  ω   -164.00 -76.00   0.50    0.05    --  -92.00 -56.00-134.11  176
 90  ω   -168.00 -78.00   0.50    0.05    --  -96.00 -66.00  52.63  180
 91  ω   -168.00-126.00   0.50    0.05    --  -96.00 -77.00 -27.92   84
 92  ω   -172.00 -78.00   0.50    0.05    -- -100.00 -77.00   0.00  188
 93  ω   -172.00-122.00   0.50    0.05    -- -100.00 -77.00 120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0008649000
_diffrn_orient_matrix_UB_12      0.0448571000
_diffrn_orient_matrix_UB_13      0.0897908000
_diffrn_orient_matrix_UB_21      0.0141808000
_diffrn_orient_matrix_UB_22      0.1458530000
_diffrn_orient_matrix_UB_23      -0.0277923000
_diffrn_orient_matrix_UB_31      -0.3089066000
_diffrn_orient_matrix_UB_32      0.0322829000
_diffrn_orient_matrix_UB_33      0.0053300000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3162
_reflns_number_total             3225
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.067
_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)+(0.0438P)²+0.6454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J),
 C00K(H00K), C00N(H00N), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00M(H00H,H00I,H00L)
;
_atom_sites_solution_hydrogens   mixed
_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
S001 S 0.87869(7) 0.17235(4) 0.40775(2) 0.01570(11) Uani 1 1 d . . . . .
F002 F -0.2436(2) 0.63858(10) 0.79518(6) 0.0276(2) Uani 1 1 d . . . . .
F003 F -0.1717(2) 0.58810(11) 0.92036(6) 0.0288(2) Uani 1 1 d . . . . .
F004 F 0.0271(2) 0.73741(10) 0.85909(7) 0.0311(3) Uani 1 1 d . . . . .
O005 O 0.8556(2) 0.03172(11) 0.40811(7) 0.0217(3) Uani 1 1 d . . . . .
O006 O 1.1363(2) 0.21276(13) 0.39081(7) 0.0236(3) Uani 1 1 d . . . . .
N007 N 0.4536(3) 0.38913(13) 0.73767(8) 0.0158(3) Uani 1 1 d . . . . .
N008 N 0.2376(3) 0.49007(13) 0.74088(8) 0.0165(3) Uani 1 1 d . . . . .
N009 N 0.6880(3) 0.24495(14) 0.34127(8) 0.0177(3) Uani 1 1 d . . . . .
H00A H 0.712(4) 0.326(2) 0.3292(12) 0.021 Uiso 1 1 d . U . . .
H00B H 0.521(5) 0.234(2) 0.3496(12) 0.021 Uiso 1 1 d . U . . .
C00A C 0.5575(3) 0.33883(15) 0.65776(9) 0.0157(3) Uani 1 1 d . . . . .
C00B C 0.1731(3) 0.50958(15) 0.82064(9) 0.0162(3) Uani 1 1 d . . . . .
C00C C 0.3409(3) 0.42392(15) 0.86854(9) 0.0175(3) Uani 1 1 d . . . . .
H00C H 0.332693 0.420026 0.925287 0.021 Uiso 1 1 calc R U . . .
C00D C 0.5443(3) 0.18542(16) 0.54704(10) 0.0176(3) Uani 1 1 d . . . . .
H00D H 0.472358 0.116351 0.523464 0.021 Uiso 1 1 calc R U . . .
C00E C 0.4469(3) 0.23586(16) 0.62367(10) 0.0174(3) Uani 1 1 d . . . . .
H00E H 0.308253 0.201108 0.652170 0.021 Uiso 1 1 calc R U . . .
C00F C 1.0549(3) 0.14159(16) 0.93138(10) 0.0198(3) Uani 1 1 d . . . . .
H00F H 1.108785 0.140817 0.984405 0.024 Uiso 1 1 calc R U . . .
C00G C 0.7618(3) 0.39447(16) 0.61646(10) 0.0189(3) Uani 1 1 d . . . . .
H00G H 0.831632 0.464421 0.639848 0.023 Uiso 1 1 calc R U . . .
C00H C 0.7516(3) 0.24065(15) 0.83129(9) 0.0163(3) Uani 1 1 d . . . . .
C00I C 0.5235(3) 0.34536(15) 0.81371(9) 0.0159(3) Uani 1 1 d . . . . .
C00J C 0.8839(3) 0.14334(16) 0.77489(10) 0.0203(3) Uani 1 1 d . . . . .
H00J H 0.826678 0.141910 0.722351 0.024 Uiso 1 1 calc R U . . .
C00K C 1.0997(3) 0.04881(16) 0.79629(10) 0.0200(3) Uani 1 1 d . . . . .
H00K H 1.185310 -0.014329 0.757476 0.024 Uiso 1 1 calc R U . . .
C00L C -0.0531(3) 0.61822(16) 0.84818(10) 0.0193(3) Uani 1 1 d . . . . .
C00M C 1.4288(3) -0.05558(16) 0.89554(10) 0.0210(3) Uani 1 1 d . . . . .
H00H H 1.581659 -0.011067 0.899144 0.031 Uiso 1 1 calc R U . . .
H00I H 1.467825 -0.124639 0.853898 0.031 Uiso 1 1 calc R U . . .
H00L H 1.388544 -0.095951 0.947102 0.031 Uiso 1 1 calc R U . . .
C00N C 0.8417(3) 0.23698(16) 0.91032(10) 0.0188(3) Uani 1 1 d . . . . .
H00N H 0.756302 0.299940 0.949265 0.023 Uiso 1 1 calc R U . . .
C00O C 1.1912(3) 0.04614(15) 0.87433(10) 0.0177(3) Uani 1 1 d . . . . .
C00P C 0.8602(3) 0.34348(16) 0.53936(10) 0.0192(3) Uani 1 1 d . . . . .
H00P H 0.997584 0.378838 0.510636 0.023 Uiso 1 1 calc R U . . .
C00Q C 0.7517(3) 0.23948(15) 0.50564(9) 0.0155(3) Uani 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
S001 O005 1.4321(12) . ?
S001 O006 1.4364(12) . ?
S001 N009 1.6027(14) . ?
S001 C00Q 1.7772(15) . ?
F002 C00L 1.3358(19) . ?
F003 C00L 1.3453(19) . ?
F004 C00L 1.3387(19) . ?
N007 N008 1.3599(18) . ?
N007 C00A 1.4373(19) . ?
N007 C00I 1.3729(19) . ?
N008 C00B 1.333(2) . ?
N009 H00A 0.86(2) . ?
N009 H00B 0.87(2) . ?
C00A C00E 1.388(2) . ?
C00A C00G 1.388(2) . ?
C00B C00C 1.389(2) . ?
C00B C00L 1.489(2) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.388(2) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.382(2) . ?
C00D C00Q 1.393(2) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00N 1.382(2) . ?
C00F C00O 1.400(2) . ?
C00G H00G 0.9300 . ?
C00G C00P 1.392(2) . ?
C00H C00I 1.471(2) . ?
C00H C00J 1.398(2) . ?
C00H C00N 1.404(2) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.388(2) . ?
C00K H00K 0.9300 . ?
C00K C00O 1.392(2) . ?
C00M H00H 0.9600 . ?
C00M H00I 0.9600 . ?
C00M H00L 0.9600 . ?
C00M C00O 1.504(2) . ?
C00N H00N 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.388(2) . ?

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
O005 S001 O006 120.06(7) . . ?
O005 S001 N009 107.64(7) . . ?
O005 S001 C00Q 107.00(7) . . ?
O006 S001 N009 106.53(7) . . ?
O006 S001 C00Q 107.02(7) . . ?
N009 S001 C00Q 108.12(7) . . ?
N008 N007 C00A 116.55(12) . . ?
N008 N007 C00I 112.74(12) . . ?
C00I N007 C00A 130.51(13) . . ?
C00B N008 N007 103.80(12) . . ?
S001 N009 H00A 114.7(14) . . ?
S001 N009 H00B 113.7(13) . . ?
H00A N009 H00B 115.2(19) . . ?
C00E C00A N007 118.43(14) . . ?
C00G C00A N007 119.77(14) . . ?
C00G C00A C00E 121.80(14) . . ?
N008 C00B C00C 112.78(14) . . ?
N008 C00B C00L 119.16(14) . . ?
C00C C00B C00L 128.03(14) . . ?
C00B C00C H00C 127.3 . . ?
C00I C00C C00B 105.36(14) . . ?
C00I C00C H00C 127.3 . . ?
C00E C00D H00D 120.5 . . ?
C00E C00D C00Q 119.07(14) . . ?
C00Q C00D H00D 120.5 . . ?
C00A C00E H00E 120.3 . . ?
C00D C00E C00A 119.49(14) . . ?
C00D C00E H00E 120.3 . . ?
C00N C00F H00F 119.4 . . ?
C00N C00F C00O 121.19(15) . . ?
C00O C00F H00F 119.4 . . ?
C00A C00G H00G 120.7 . . ?
C00A C00G C00P 118.68(14) . . ?
C00P C00G H00G 120.7 . . ?
C00J C00H C00I 124.56(14) . . ?
C00J C00H C00N 117.48(14) . . ?
C00N C00H C00I 117.96(14) . . ?
N007 C00I C00C 105.31(13) . . ?
N007 C00I C00H 126.18(14) . . ?
C00C C00I C00H 128.46(14) . . ?
C00H C00J H00J 119.6 . . ?
C00K C00J C00H 120.87(15) . . ?
C00K C00J H00J 119.6 . . ?
C00J C00K H00K 119.2 . . ?
C00J C00K C00O 121.67(15) . . ?
C00O C00K H00K 119.2 . . ?
F002 C00L F003 107.08(13) . . ?
F002 C00L F004 106.89(13) . . ?
F002 C00L C00B 112.52(13) . . ?
F003 C00L C00B 111.36(13) . . ?
F004 C00L F003 106.12(13) . . ?
F004 C00L C00B 112.47(13) . . ?
H00H C00M H00I 109.5 . . ?
H00H C00M H00L 109.5 . . ?
H00I C00M H00L 109.5 . . ?
C00O C00M H00H 109.5 . . ?
C00O C00M H00I 109.5 . . ?
C00O C00M H00L 109.5 . . ?
C00F C00N C00H 121.27(15) . . ?
C00F C00N H00N 119.4 . . ?
C00H C00N H00N 119.4 . . ?
C00F C00O C00M 121.85(14) . . ?
C00K C00O C00F 117.49(14) . . ?
C00K C00O C00M 120.66(15) . . ?
C00G C00P H00P 120.2 . . ?
C00Q C00P C00G 119.54(14) . . ?
C00Q C00P H00P 120.2 . . ?
C00D C00Q S001 118.73(12) . . ?
C00P C00Q S001 119.86(12) . . ?
C00P C00Q C00D 121.41(14) . . ?

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
O005 S001 C00Q C00D -32.21(14) . . . . ?
O005 S001 C00Q C00P 147.56(13) . . . . ?
O006 S001 C00Q C00D -162.11(12) . . . . ?
O006 S001 C00Q C00P 17.67(15) . . . . ?
N007 N008 C00B C00C -0.17(17) . . . . ?
N007 N008 C00B C00L 177.85(13) . . . . ?
N007 C00A C00E C00D -179.73(14) . . . . ?
N007 C00A C00G C00P 179.64(14) . . . . ?
N008 N007 C00A C00E -87.06(17) . . . . ?
N008 N007 C00A C00G 92.24(17) . . . . ?
N008 N007 C00I C00C -0.24(17) . . . . ?
N008 N007 C00I C00H -178.14(14) . . . . ?
N008 C00B C00C C00I 0.03(18) . . . . ?
N008 C00B C00L F002 31.2(2) . . . . ?
N008 C00B C00L F003 151.45(14) . . . . ?
N008 C00B C00L F004 -89.57(18) . . . . ?
N009 S001 C00Q C00D 83.48(14) . . . . ?
N009 S001 C00Q C00P -96.74(14) . . . . ?
C00A N007 N008 C00B 175.68(13) . . . . ?
C00A N007 C00I C00C -174.85(15) . . . . ?
C00A N007 C00I C00H 7.2(3) . . . . ?
C00A C00G C00P C00Q 0.3(2) . . . . ?
C00B C00C C00I N007 0.12(17) . . . . ?
C00B C00C C00I C00H 177.96(15) . . . . ?
C00C C00B C00L F002 -151.09(16) . . . . ?
C00C C00B C00L F003 -30.9(2) . . . . ?
C00C C00B C00L F004 88.1(2) . . . . ?
C00E C00A C00G C00P -1.1(2) . . . . ?
C00E C00D C00Q S001 179.14(12) . . . . ?
C00E C00D C00Q C00P -0.6(2) . . . . ?
C00G C00A C00E C00D 1.0(2) . . . . ?
C00G C00P C00Q S001 -179.24(12) . . . . ?
C00G C00P C00Q C00D 0.5(2) . . . . ?
C00H C00J C00K C00O 0.6(3) . . . . ?
C00I N007 N008 C00B 0.25(16) . . . . ?
C00I N007 C00A C00E 87.4(2) . . . . ?
C00I N007 C00A C00G -93.3(2) . . . . ?
C00I C00H C00J C00K 179.31(15) . . . . ?
C00I C00H C00N C00F -179.96(14) . . . . ?
C00J C00H C00I N007 -19.5(2) . . . . ?
C00J C00H C00I C00C 163.09(16) . . . . ?
C00J C00H C00N C00F 0.6(2) . . . . ?
C00J C00K C00O C00F 0.9(2) . . . . ?
C00J C00K C00O C00M -178.80(15) . . . . ?
C00L C00B C00C C00I -177.78(15) . . . . ?
C00N C00F C00O C00K -1.6(2) . . . . ?
C00N C00F C00O C00M 178.10(15) . . . . ?
C00N C00H C00I N007 161.13(15) . . . . ?
C00N C00H C00I C00C -16.3(2) . . . . ?
C00N C00H C00J C00K -1.3(2) . . . . ?
C00O C00F C00N C00H 0.8(2) . . . . ?
C00Q C00D C00E C00A -0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.285
_oxdiff_exptl_absorpt_empirical_full_min 0.540
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Aspirin-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987510'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-24
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Aspirin
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 O4'
_chemical_formula_sum            'C9 H8 O4'
_chemical_formula_weight         180.15
_chemical_melting_point          415K
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'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2582(3)
_cell_length_b                   6.54710(10)
_cell_length_c                   11.2600(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.949(2)
_cell_angle_gamma                90
_cell_volume                     825.49(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8315
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1610
_cell_measurement_theta_min      3.9230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13802
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.931
_diffrn_reflns_theta_min         3.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  61.00   0.50    0.35    --   46.25 -38.00  60.00  176
  2  ω     -5.00  83.00   0.50    0.35    --   46.25-103.00  72.00  176
  3  ω     33.00 110.00   0.50    1.38    --  105.44-103.00  72.00  154
  4  ω     33.00 178.00   0.50    1.38    --  105.44   0.00 -90.00  290
  5  ω     90.00 178.00   0.50    1.38    --  105.44  30.00   0.00  176
  6  ω     86.00 178.00   0.50    1.38    --  105.44 103.00 174.00  184
  7  ω     33.00 108.00   0.50    1.38    --  105.44 -94.00  30.00  150
  8  ω     29.00 123.00   0.50    1.38    --  105.44 -15.00-120.00  188
  9  ω     33.00 108.00   0.50    1.38    --  105.44 -94.00 -90.00  150
 10  ω     33.00 120.00   0.50    1.38    --  105.44 -45.00  60.00  174
 11  ω     33.00 178.00   0.50    1.38    --  105.44   0.00 -90.00  290
 12  ω     33.00 108.00   0.50    1.38    --  105.44 -94.00-120.00  150
 13  ω     15.00  95.00   0.50    0.35    --   46.25-125.00 -90.00  160
 14  ω    -27.00  61.00   0.50    0.35    --   46.25 -38.00 120.00  176
 15  ω     30.00 118.00   0.50    0.35    --   46.25  57.00  90.00  176
 16  ω     30.00 118.00   0.50    0.35    --   46.25  57.00  30.00  176
 17  ω     30.00 118.00   0.50    0.35    --   46.25  57.00 150.00  176
 18  ω     23.00 118.00   0.50    0.35    --   46.25  77.00 -60.00  190
 19  ω     23.00 118.00   0.50    0.35    --   46.25  77.00-180.00  190
 20  ω     30.00 118.00   0.50    0.35    --   46.25  57.00 -90.00  176
 21  ω    -83.00   9.00   0.50    0.35    --  -46.25 103.00 174.00  184
 22  ω   -110.00 -27.00   0.50    1.38    -- -100.00 103.00 174.00  166
 23  ω   -115.00 -25.00   0.50    1.38    -- -100.00  30.00 150.00  180
 24  ω   -117.00 -27.00   0.50    1.38    -- -100.00 125.00 -30.00  180
 25  ω   -118.00 -24.00   0.50    1.38    -- -100.00  15.00-150.00  188
 26  ω   -118.00 -71.00   0.50    0.35    --  -46.25-125.00-150.00   94
 27  ω   -118.00 -71.00   0.50    0.35    --  -46.25-125.00-180.00   94
 28  ω   -118.00 -71.00   0.50    0.35    --  -46.25-125.00 -60.00   94
 29  ω   -173.00 -82.00   0.50    1.38    -- -100.00-103.00  72.00  182
 30  ω   -173.00 -82.00   0.50    1.38    -- -100.00 -61.00 120.00  182
 31  ω   -175.00 -84.00   0.50    1.38    -- -100.00 -30.00 -30.00  182
 32  ω   -173.00-138.00   0.50    1.38    -- -100.00 -61.00  90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124908000
_diffrn_orient_matrix_UB_12      -0.1821279000
_diffrn_orient_matrix_UB_13      0.0844276000
_diffrn_orient_matrix_UB_21      0.1250412000
_diffrn_orient_matrix_UB_22      -0.0757692000
_diffrn_orient_matrix_UB_23      -0.0233908000
_diffrn_orient_matrix_UB_31      0.0560033000
_diffrn_orient_matrix_UB_32      0.1284291000
_diffrn_orient_matrix_UB_33      0.1059793000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1578
_reflns_number_total             1682
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.061
_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)+(0.1374P)²+0.2686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.1847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00F)
2.b Idealised Me refined as rotating group:
 C00C(H00C,H00D,H00E)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
O001 O 0.21116(11) 0.41910(18) 0.58976(10) 0.0241(4) Uani 1 1 d . . . . .
O002 O 0.37610(11) 0.14234(19) 0.55341(11) 0.0271(4) Uani 1 1 d . . . . .
H002 H 0.420720 0.044600 0.568280 0.041 Uiso 1 1 calc R U . . .
O003 O 0.49012(11) 0.18650(18) 0.40434(11) 0.0276(4) Uani 1 1 d . . . . .
O004 O 0.09582(12) 0.2196(2) 0.46233(11) 0.0298(4) Uani 1 1 d . . . . .
C005 C 0.13274(15) 0.2619(2) 0.56301(15) 0.0234(4) Uani 1 1 d . . . . .
C006 C 0.34603(15) 0.4408(2) 0.43320(14) 0.0229(4) Uani 1 1 d . . . . .
C007 C 0.25256(16) 0.5187(2) 0.49192(14) 0.0235(4) Uani 1 1 d . . . . .
C008 C 0.41037(15) 0.2445(2) 0.46258(15) 0.0229(4) Uani 1 1 d . . . . .
C009 C 0.38442(15) 0.5555(2) 0.33909(15) 0.0245(4) Uani 1 1 d . . . . .
H009 H 0.446756 0.506773 0.298894 0.029 Uiso 1 1 calc R U . . .
C00A C 0.33106(16) 0.7399(3) 0.30502(16) 0.0262(4) Uani 1 1 d . . . . .
H00A H 0.356932 0.813504 0.241923 0.031 Uiso 1 1 calc R U . . .
C00B C 0.19954(16) 0.7047(3) 0.45937(16) 0.0260(4) Uani 1 1 d . . . . .
H00B H 0.138143 0.755297 0.500193 0.031 Uiso 1 1 calc R U . . .
C00C C 0.10069(17) 0.1599(3) 0.67397(16) 0.0300(5) Uani 1 1 d . . . . .
H00C H 0.171463 0.105253 0.717415 0.045 Uiso 1 1 calc R U . . .
H00D H 0.045204 0.051251 0.653021 0.045 Uiso 1 1 calc R U . . .
H00E H 0.064795 0.257745 0.722788 0.045 Uiso 1 1 calc R U . . .
C00D C 0.23875(16) 0.8144(3) 0.36552(16) 0.0275(4) Uani 1 1 d . . . . .
H00F H 0.203032 0.938471 0.343000 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.369(2) . ?
O001 C007 1.4010(19) . ?
O002 H002 0.8200 . ?
O002 C008 1.313(2) . ?
O003 C008 1.226(2) . ?
O004 C005 1.199(2) . ?
C005 C00C 1.494(2) . ?
C006 C007 1.396(2) . ?
C006 C008 1.496(2) . ?
C006 C009 1.403(2) . ?
C007 C00B 1.388(2) . ?
C009 H009 0.9300 . ?
C009 C00A 1.385(2) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.389(3) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.387(2) . ?
C00C H00C 0.9600 . ?
C00C H00D 0.9600 . ?
C00C H00E 0.9600 . ?
C00D H00F 0.9300 . ?

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
C005 O001 C007 115.88(12) . . ?
C008 O002 H002 109.5 . . ?
O001 C005 C00C 110.99(14) . . ?
O004 C005 O001 122.29(15) . . ?
O004 C005 C00C 126.71(15) . . ?
C007 C006 C008 125.50(15) . . ?
C007 C006 C009 117.96(15) . . ?
C009 C006 C008 116.54(15) . . ?
C006 C007 O001 122.07(14) . . ?
C00B C007 O001 116.54(15) . . ?
C00B C007 C006 121.32(15) . . ?
O002 C008 C006 115.82(14) . . ?
O003 C008 O002 123.34(15) . . ?
O003 C008 C006 120.85(15) . . ?
C006 C009 H009 119.4 . . ?
C00A C009 C006 121.12(16) . . ?
C00A C009 H009 119.4 . . ?
C009 C00A H00A 120.2 . . ?
C009 C00A C00D 119.70(16) . . ?
C00D C00A H00A 120.2 . . ?
C007 C00B H00B 120.2 . . ?
C00D C00B C007 119.55(16) . . ?
C00D C00B H00B 120.2 . . ?
C005 C00C H00C 109.5 . . ?
C005 C00C H00D 109.5 . . ?
C005 C00C H00E 109.5 . . ?
H00C C00C H00D 109.5 . . ?
H00C C00C H00E 109.5 . . ?
H00D C00C H00E 109.5 . . ?
C00A C00D H00F 119.8 . . ?
C00B C00D C00A 120.34(16) . . ?
C00B C00D H00F 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C007 C00B C00D 178.09(14) . . . . ?
C005 O001 C007 C006 -81.7(2) . . . . ?
C005 O001 C007 C00B 101.18(17) . . . . ?
C006 C007 C00B C00D 1.0(3) . . . . ?
C006 C009 C00A C00D 0.7(3) . . . . ?
C007 O001 C005 O004 -4.4(2) . . . . ?
C007 O001 C005 C00C 176.61(13) . . . . ?
C007 C006 C008 O002 -1.7(2) . . . . ?
C007 C006 C008 O003 178.59(16) . . . . ?
C007 C006 C009 C00A -0.2(3) . . . . ?
C007 C00B C00D C00A -0.5(3) . . . . ?
C008 C006 C007 O001 1.9(3) . . . . ?
C008 C006 C007 C00B 178.92(15) . . . . ?
C008 C006 C009 C00A -179.78(15) . . . . ?
C009 C006 C007 O001 -177.54(14) . . . . ?
C009 C006 C007 C00B -0.6(3) . . . . ?
C009 C006 C008 O002 177.81(14) . . . . ?
C009 C006 C008 O003 -1.9(2) . . . . ?
C009 C00A C00D C00B -0.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.260
_oxdiff_exptl_absorpt_empirical_full_min 0.434
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Indomethacin-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987513'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-26
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Indomethacin
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 Cl N O4'
_chemical_formula_sum            'C19 H16 Cl N O4'
_chemical_formula_weight         357.78
_chemical_melting_point          436K
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'
O O 0.0492 0.0322 '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'
Cl Cl 0.3639 0.7018 '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                   9.21730(10)
_cell_length_b                   9.6060(2)
_cell_length_c                   10.8436(2)
_cell_angle_alpha                69.959(2)
_cell_angle_beta                 87.1970(10)
_cell_angle_gamma                69.501(2)
_cell_volume                     842.09(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16583
_cell_measurement_temperature    99.97(11)
_cell_measurement_theta_max      76.2890
_cell_measurement_theta_min      5.1300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32458
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.808
_diffrn_reflns_theta_min         4.354
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -31.00   0.50    0.08    --  -46.37 -20.00 132.00  180
  2  ω    -61.00  30.00   0.50    0.08    --  -46.37  20.00 -60.00  182
  3  ω     31.00 122.00   0.50    0.08    --   46.37  20.00 -60.00  182
  4  ω    -29.00  62.00   0.50    0.08    --   46.37 -20.00 132.00  182
  5  ω   -115.00 -24.00   0.50    0.32    -- -100.00  20.00 -60.00  182
  6  ω   -175.00 -85.00   0.50    0.32    -- -100.00 -20.00 132.00  180
  7  ω     92.00 178.00   0.50    0.32    --  107.00  20.00 -60.00  172
  8  ω     31.00 122.00   0.50    0.32    --  107.00 -20.00 132.00  182
  9  ω     10.00 109.00   0.50    0.08    --   36.00  83.00 156.30  198
 10  ω     17.00  45.00   0.50    0.08    --   44.00  84.00 -37.85   56
 11  ω     16.00  45.00   0.50    0.08    --   44.00  86.00-124.53   58
 12  ω   -120.00 -32.00   0.50    0.08    --  -46.37 -38.00  60.00  176
 13  ω   -118.00 -30.00   0.50    0.08    --  -46.37 -57.00 150.00  176
 14  ω   -118.00 -23.00   0.50    0.08    --  -46.37 -77.00  90.00  190
 15  ω   -118.00 -23.00   0.50    0.08    --  -46.37 -77.00-180.00  190
 16  ω   -119.00 -32.00   0.50    0.08    --  -46.37 -43.00 -69.45  174
 17  ω   -120.00 -32.00   0.50    0.08    --  -46.37 -38.00  90.00  176
 18  ω   -118.00 -30.00   0.50    0.08    --  -46.37 -57.00   0.00  176
 19  ω     23.00 118.00   0.50    0.08    --   46.37  77.00-120.00  190
 20  ω    -25.00  63.00   0.50    0.08    --   46.37 -57.00   0.00  176
 21  ω     15.00  95.00   0.50    0.08    --   46.37-125.00 -90.00  160
 22  ω     19.00  45.00   0.50    0.08    --   48.00  89.00  43.04   52
 23  ω     19.00  45.00   0.50    0.08    --   48.00  88.00 -32.39   52
 24  ω     28.00 125.00   0.50    0.08    --   52.00  77.00 140.18  194
 25  ω   -128.00 -30.00   0.50    0.08    --  -56.00 -81.00 -47.86  196
 26  ω     33.00 129.00   0.50    0.08    --   56.00  75.00 158.90  192
 27  ω     32.00 129.00   0.50    0.08    --   56.00  78.00-114.31  194
 28  ω     32.00  57.00   0.50    0.08    --   56.00  79.00  81.85   50
 29  ω   -137.00 -85.00   0.50    0.08    --  -64.00 -72.00 -82.00  104
 30  ω    -75.00 -39.00   0.50    0.08    --  -64.00 -80.00  -8.77   72
 31  ω    -68.00 -42.00   0.50    0.08    --  -64.00 -73.00 170.54   52
 32  ω    -66.00 -40.00   0.50    0.08    --  -64.00 -76.00 -99.88   52
 33  ω    -63.00 -37.00   0.50    0.08    --  -64.00 -83.00  28.47   52
 34  ω    -75.00 -42.00   0.50    0.08    --  -64.00 -72.00 -82.00   66
 35  ω   -130.00-104.00   0.50    0.08    --  -64.00 -83.00  28.47   52
 36  ω    -68.00 -43.00   0.50    0.08    --  -68.00 -79.00-129.84   50
 37  ω    -74.00 -48.00   0.50    0.08    --  -68.00 -71.00 -22.78   52
 38  ω    -75.00 -49.00   0.50    0.08    --  -68.00 -69.00  70.07   52
 39  ω   -137.00-112.00   0.50    0.08    --  -68.00 -79.00-129.84   50
 40  ω    -76.00 -50.00   0.50    0.08    --  -72.00 -74.00  19.08   52
 41  ω    -74.00 -48.00   0.50    0.08    --  -72.00 -76.00 123.50   52
 42  ω    -82.00 -56.00   0.50    0.32    --  -76.00 -68.00 137.73   52
 43  ω    -81.00 -55.00   0.50    0.32    --  -76.00 -73.00 179.30   52
 44  ω    -90.00 -58.00   0.50    0.32    --  -80.00 -73.00 -35.79   64
 45  ω    -86.00 -53.00   0.50    0.32    --  -80.00 -83.00  85.12   66
 46  ω    -79.00 -54.00   0.50    0.32    --  -80.00 -81.00-120.75   50
 47  ω    -83.00 -57.00   0.50    0.32    --  -80.00 -75.00  -0.20   52
 48  ω    -93.00 -58.00   0.50    0.32    --  -80.00 -74.00 -98.63   70
 49  ω    -93.00 -61.00   0.50    0.32    --  -84.00 -74.00 -57.57   64
 50  ω   -149.00-123.00   0.50    0.32    --  -84.00 -73.00 -68.34   52
 51  ω    -90.00 -64.00   0.50    0.32    --  -84.00 -73.00 -68.34   52
 52  ω    -90.00 -64.00   0.50    0.32    --  -84.00 -72.00 113.53   52
 53  ω    -94.00 -69.00   0.50    0.32    --  -88.00 -65.00-154.95   50
 54  ω    -96.00 -70.00   0.50    0.32    --  -88.00 -64.00  32.23   52
 55  ω   -106.00 -72.00   0.50    0.32    --  -88.00 -59.00  14.32   68
 56  ω    -87.00 -61.00   0.50    0.32    --  -88.00 -83.00-167.79   52
 57  ω    -94.00 -68.00   0.50    0.32    --  -88.00 -72.00 136.97   52
 58  ω    -97.00 -71.00   0.50    0.32    --  -88.00 -63.00 -92.95   52
 59  ω    -91.00 -66.00   0.50    0.32    --  -88.00 -73.00-118.91   50
 60  ω    -97.00 -69.00   0.50    0.32    --  -92.00 -75.00-128.38   56
 61  ω   -161.00-135.00   0.50    0.32    --  -92.00 -75.00-128.38   52
 62  ω   -168.00 -72.00   0.50    0.32    --  -96.00 -76.00  16.07  192
 63  ω   -113.00 -62.00   0.50    0.32    -- -100.00  45.00 120.00  102
 64  ω   -102.00 -76.00   0.50    0.32    -- -100.00 -78.00  -2.85   52
 65  ω   -102.00 -76.00   0.50    0.32    -- -100.00 -77.00-180.00   52
 66  ω    -63.00 -28.00   0.50    0.32    -- -100.00 125.00 -60.00   70
 67  ω   -161.00 -80.00   0.50    0.32    -- -100.00 -70.00   2.19  162
 68  ω   -116.00 -91.00   0.50    0.32    -- -100.00 125.00 -60.00   50
 69  ω   -105.00 -80.00   0.50    0.32    -- -100.00 -68.00 121.02   50
 70  ω   -173.00-111.00   0.50    0.32    -- -100.00 -68.00 121.02  124
 71  ω   -114.00 -76.00   0.50    0.32    -- -100.00 -78.00-105.25   76
 72  ω   -113.00 -78.00   0.50    0.32    -- -100.00 -72.00 -60.04   70
 73  ω   -155.00-130.00   0.50    0.32    -- -100.00 -78.00-105.25   50
 74  ω   -151.00 -82.00   0.50    0.32    -- -100.00 -63.00 -93.70  138
 75  ω   -118.00 -80.00   0.50    0.32    -- -100.00 -67.00 -26.20   76
 76  ω     75.00 107.00   0.50    0.32    --  100.00  83.00  53.46   64
 77  ω   -172.00-126.00   0.50    0.32    -- -100.00 -67.00 -26.20   92
 78  ω   -136.00 -82.00   0.50    0.32    -- -100.00 -75.00 -39.79  108
 79  ω   -119.00 -76.00   0.50    0.32    -- -100.00 -76.00  37.89   86
 80  ω   -149.00-123.00   0.50    0.32    -- -100.00 -72.00 -60.04   52
 81  ω   -173.00-147.00   0.50    0.32    -- -100.00 -76.00  37.89   52
 82  ω   -137.00 -77.00   0.50    0.32    -- -100.00 -76.00-145.30  120
 83  ω   -121.00 -85.00   0.50    0.32    -- -100.00 -56.00 164.91   72
 84  ω   -104.00 -78.00   0.50    0.32    -- -100.00 -77.00  81.86   52
 85  ω   -162.00 -81.00   0.50    0.32    -- -100.00 -72.00 104.40  162
 86  ω   -151.00 -85.00   0.50    0.32    -- -100.00 -45.00 120.00  132
 87  ω   -136.00 -99.00   0.50    0.32    -- -100.00 -61.00-150.00   74
 88  ω   -172.00 -76.00   0.50    0.32    -- -100.00 -76.00  72.77  192
 89  ω     75.00 108.00   0.50    0.32    --  107.00 -94.00 150.00   66
 90  ω     83.00 151.00   0.50    0.32    --  107.00  77.00 120.00  136
 91  ω    146.00 172.00   0.50    0.32    --  107.00  30.00  30.00   52
 92  ω    118.00 144.00   0.50    0.32    --  107.00  30.00  30.00   52
 93  ω     43.00  69.00   0.50    0.32    --  107.00 -94.00 150.00   52
 94  ω     56.00  87.00   0.50    0.32    --  107.00 -61.00 -30.00   62
 95  ω     76.00 108.00   0.50    0.32    --  107.00 -94.00-150.00   64
 96  ω     39.00 122.00   0.50    0.32    --  107.00 -45.00 120.00  166
 97  ω    132.00 176.00   0.50    0.32    --  107.00  61.00 150.00   88
 98  ω     90.00 123.00   0.50    0.32    --  107.00  61.00 150.00   66
 99  ω    148.00 173.00   0.50    0.32    --  107.00  61.00 -30.00   50
100  ω     91.00 118.00   0.50    0.32    --  107.00  61.00 -30.00   54
101  ω     91.00 176.00   0.50    0.32    --  107.00  61.00-120.00  170
102  ω     78.00 117.00   0.50    0.32    --  107.00-125.00 120.00   78
103  ω     35.00 107.00   0.50    0.32    --  107.00 -94.00  90.00  144
104  ω     34.00  81.00   0.50    0.32    --  107.00 -94.00 120.00   94
105  ω     79.00 114.00   0.50    0.32    --  107.00-125.00  90.00   70
106  ω     35.00  73.00   0.50    0.32    --  107.00-125.00  90.00   76
107  ω     35.00  97.00   0.50    0.32    --  107.00-125.00   0.00  124
108  ω     83.00 116.00   0.50    0.32    --  107.00-125.00-150.00   66
109  ω     36.00 121.00   0.50    0.32    --  107.00 -45.00-120.00  170
110  ω     85.00 111.00   0.50    0.32    --  107.00-125.00 -30.00   52
111  ω     38.00  63.00   0.50    0.32    --  107.00-125.00 -30.00   50
112  ω     72.00 122.00   0.50    0.32    --  107.00 -77.00-150.00  100
113  ω     35.00  69.00   0.50    0.32    --  107.00 -77.00-150.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1763409000
_diffrn_orient_matrix_UB_12      -0.0568038000
_diffrn_orient_matrix_UB_13      0.0336848000
_diffrn_orient_matrix_UB_21      -0.0213160000
_diffrn_orient_matrix_UB_22      0.1556335000
_diffrn_orient_matrix_UB_23      0.0225340000
_diffrn_orient_matrix_UB_31      -0.0223292000
_diffrn_orient_matrix_UB_32      -0.0768516000
_diffrn_orient_matrix_UB_33      0.1462114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3165
_reflns_number_total             3473
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.111
_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)+(0.0364P)²+0.4237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0876
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M),
 C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00O(H00C,H00D,H00F), C00P(H00I,H00L,H00O)
2.d Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_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
Cl01 Cl -0.30897(4) 0.95573(4) -0.06987(4) 0.03011(12) Uani 1 1 d . . . . .
O002 O 0.88513(11) 0.16566(12) 0.39483(10) 0.0225(2) Uani 1 1 d . . . . .
O003 O 0.46403(12) 0.67064(12) -0.00881(10) 0.0243(2) Uani 1 1 d . . . . .
O004 O 0.27615(12) 0.07767(13) 0.59346(11) 0.0269(2) Uani 1 1 d . . . . .
O005 O 0.91800(13) 0.10858(13) 0.61152(10) 0.0288(3) Uani 1 1 d . . . . .
H005 H 0.984329 0.027147 0.607674 0.043 Uiso 1 1 calc R U . . .
N006 N 0.43268(13) 0.54069(14) 0.20536(11) 0.0185(2) Uani 1 1 d . . . . .
C007 C 0.47420(15) 0.34871(16) 0.40637(14) 0.0178(3) Uani 1 1 d . . . . .
C008 C 0.37266(15) 0.42996(16) 0.29246(14) 0.0183(3) Uani 1 1 d . . . . .
C009 C 0.57333(15) 0.52313(16) 0.26679(14) 0.0186(3) Uani 1 1 d . . . . .
C00A C 0.37660(16) 0.63815(16) 0.07428(14) 0.0195(3) Uani 1 1 d . . . . .
C00B C 0.85106(15) 0.19968(16) 0.49343(14) 0.0181(3) Uani 1 1 d . . . . .
C00C C 0.59794(15) 0.41115(16) 0.38817(14) 0.0181(3) Uani 1 1 d . . . . .
C00D C 0.20461(16) 0.70586(16) 0.04507(14) 0.0193(3) Uani 1 1 d . . . . .
C00E C 0.44769(16) 0.22857(16) 0.51233(14) 0.0193(3) Uani 1 1 d . . . . .
H00E H 0.515202 0.175292 0.588232 0.023 Uiso 1 1 calc R U . . .
C00F C 0.31764(16) 0.19203(16) 0.50004(14) 0.0205(3) Uani 1 1 d . . . . .
C00G C 0.24385(16) 0.39031(17) 0.27886(14) 0.0216(3) Uani 1 1 d . . . . .
H00G H 0.178051 0.441096 0.201941 0.026 Uiso 1 1 calc R U . . .
C00H C 0.21759(16) 0.27286(17) 0.38383(15) 0.0230(3) Uani 1 1 d . . . . .
H00H H 0.131067 0.246389 0.377491 0.028 Uiso 1 1 calc R U . . .
C00I C 0.72892(15) 0.35440(16) 0.49038(14) 0.0193(3) Uani 1 1 d . . . . .
H00A H 0.688116 0.340901 0.576173 0.023 Uiso 1 1 calc R U . . .
H00B H 0.776448 0.434118 0.472521 0.023 Uiso 1 1 calc R U . . .
C00J C 0.14311(17) 0.72455(16) -0.07703(14) 0.0211(3) Uani 1 1 d . . . . .
H00J H 0.208658 0.688114 -0.136057 0.025 Uiso 1 1 calc R U . . .
C00K C 0.10597(16) 0.76387(17) 0.13207(14) 0.0213(3) Uani 1 1 d . . . . .
H00K H 0.146896 0.751068 0.213615 0.026 Uiso 1 1 calc R U . . .
C00L C -0.11109(16) 0.85586(17) -0.02347(15) 0.0228(3) Uani 1 1 d . . . . .
C00M C -0.01577(17) 0.79746(17) -0.11056(15) 0.0238(3) Uani 1 1 d . . . . .
H00M H -0.057670 0.806947 -0.190616 0.029 Uiso 1 1 calc R U . . .
C00N C -0.05255(17) 0.84045(17) 0.09808(15) 0.0225(3) Uani 1 1 d . . . . .
H00N H -0.118156 0.880574 0.155416 0.027 Uiso 1 1 calc R U . . .
C00O C 0.66592(17) 0.62527(17) 0.20291(15) 0.0235(3) Uani 1 1 d . . . . .
H00C H 0.720184 0.591594 0.134404 0.035 Uiso 1 1 calc R U . . .
H00D H 0.739584 0.616165 0.267460 0.035 Uiso 1 1 calc R U . . .
H00F H 0.597470 0.733658 0.165820 0.035 Uiso 1 1 calc R U . . .
C00P C 0.38200(17) -0.02008(17) 0.70713(15) 0.0246(3) Uani 1 1 d . . . . .
H00I H 0.482313 -0.068606 0.680304 0.037 Uiso 1 1 calc R U . . .
H00L H 0.344708 -0.100954 0.761359 0.037 Uiso 1 1 calc R U . . .
H00O H 0.390194 0.043539 0.756207 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00L 1.7417(14) . ?
O002 C00B 1.2179(17) . ?
O003 C00A 1.2128(18) . ?
O004 C00F 1.3685(17) . ?
O004 C00P 1.4267(18) . ?
O005 H005 0.8200 . ?
O005 C00B 1.3105(17) . ?
N006 C008 1.4149(18) . ?
N006 C009 1.4167(17) . ?
N006 C00A 1.4089(18) . ?
C007 C008 1.3970(19) . ?
C007 C00C 1.4407(19) . ?
C007 C00E 1.405(2) . ?
C008 C00G 1.3959(19) . ?
C009 C00C 1.352(2) . ?
C009 C00O 1.4946(19) . ?
C00A C00D 1.4907(19) . ?
C00B C00I 1.5085(18) . ?
C00C C00I 1.4963(18) . ?
C00D C00J 1.395(2) . ?
C00D C00K 1.396(2) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.3857(19) . ?
C00F C00H 1.408(2) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.382(2) . ?
C00H H00H 0.9300 . ?
C00I H00A 0.9700 . ?
C00I H00B 0.9700 . ?
C00J H00J 0.9300 . ?
C00J C00M 1.388(2) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.388(2) . ?
C00L C00M 1.384(2) . ?
C00L C00N 1.389(2) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00C 0.9600 . ?
C00O H00D 0.9600 . ?
C00O H00F 0.9600 . ?
C00P H00I 0.9600 . ?
C00P H00L 0.9600 . ?
C00P H00O 0.9600 . ?

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
C00F O004 C00P 117.21(11) . . ?
C00B O005 H005 109.5 . . ?
C008 N006 C009 107.85(11) . . ?
C00A N006 C008 127.21(11) . . ?
C00A N006 C009 124.49(12) . . ?
C008 C007 C00C 107.55(12) . . ?
C008 C007 C00E 121.38(12) . . ?
C00E C007 C00C 131.06(13) . . ?
C007 C008 N006 107.32(12) . . ?
C00G C008 N006 131.87(13) . . ?
C00G C008 C007 120.74(13) . . ?
N006 C009 C00O 122.01(12) . . ?
C00C C009 N006 108.87(12) . . ?
C00C C009 C00O 129.00(13) . . ?
O003 C00A N006 121.38(13) . . ?
O003 C00A C00D 121.93(13) . . ?
N006 C00A C00D 116.61(12) . . ?
O002 C00B O005 123.96(13) . . ?
O002 C00B C00I 122.76(12) . . ?
O005 C00B C00I 113.26(12) . . ?
C007 C00C C00I 123.25(12) . . ?
C009 C00C C007 108.36(12) . . ?
C009 C00C C00I 128.39(13) . . ?
C00J C00D C00A 118.83(13) . . ?
C00J C00D C00K 119.65(13) . . ?
C00K C00D C00A 121.24(13) . . ?
C007 C00E H00E 121.1 . . ?
C00F C00E C007 117.81(13) . . ?
C00F C00E H00E 121.1 . . ?
O004 C00F C00E 125.03(13) . . ?
O004 C00F C00H 114.67(12) . . ?
C00E C00F C00H 120.29(13) . . ?
C008 C00G H00G 121.2 . . ?
C00H C00G C008 117.62(13) . . ?
C00H C00G H00G 121.2 . . ?
C00F C00H H00H 118.9 . . ?
C00G C00H C00F 122.12(13) . . ?
C00G C00H H00H 118.9 . . ?
C00B C00I H00A 109.2 . . ?
C00B C00I H00B 109.2 . . ?
C00C C00I C00B 112.26(11) . . ?
C00C C00I H00A 109.2 . . ?
C00C C00I H00B 109.2 . . ?
H00A C00I H00B 107.9 . . ?
C00D C00J H00J 119.9 . . ?
C00M C00J C00D 120.10(13) . . ?
C00M C00J H00J 119.9 . . ?
C00D C00K H00K 119.7 . . ?
C00N C00K C00D 120.66(13) . . ?
C00N C00K H00K 119.7 . . ?
C00M C00L Cl01 118.85(11) . . ?
C00M C00L C00N 121.79(13) . . ?
C00N C00L Cl01 119.34(12) . . ?
C00J C00M H00M 120.4 . . ?
C00L C00M C00J 119.22(13) . . ?
C00L C00M H00M 120.4 . . ?
C00K C00N C00L 118.54(14) . . ?
C00K C00N H00N 120.7 . . ?
C00L C00N H00N 120.7 . . ?
C009 C00O H00C 109.5 . . ?
C009 C00O H00D 109.5 . . ?
C009 C00O H00F 109.5 . . ?
H00C C00O H00D 109.5 . . ?
H00C C00O H00F 109.5 . . ?
H00D C00O H00F 109.5 . . ?
O004 C00P H00I 109.5 . . ?
O004 C00P H00L 109.5 . . ?
O004 C00P H00O 109.5 . . ?
H00I C00P H00L 109.5 . . ?
H00I C00P H00O 109.5 . . ?
H00L C00P H00O 109.5 . . ?

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 C00L C00M C00J 176.88(11) . . . . ?
Cl01 C00L C00N C00K -178.46(11) . . . . ?
O002 C00B C00I C00C 34.42(18) . . . . ?
O003 C00A C00D C00J 38.2(2) . . . . ?
O003 C00A C00D C00K -135.77(15) . . . . ?
O004 C00F C00H C00G -179.07(13) . . . . ?
O005 C00B C00I C00C -146.96(12) . . . . ?
N006 C008 C00G C00H 179.04(14) . . . . ?
N006 C009 C00C C007 2.06(15) . . . . ?
N006 C009 C00C C00I -178.62(12) . . . . ?
N006 C00A C00D C00J -145.00(13) . . . . ?
N006 C00A C00D C00K 41.00(18) . . . . ?
C007 C008 C00G C00H 2.5(2) . . . . ?
C007 C00C C00I C00B 78.89(16) . . . . ?
C007 C00E C00F O004 179.45(13) . . . . ?
C007 C00E C00F C00H 0.6(2) . . . . ?
C008 N006 C009 C00C -2.06(15) . . . . ?
C008 N006 C009 C00O -178.45(12) . . . . ?
C008 N006 C00A O003 -145.19(14) . . . . ?
C008 N006 C00A C00D 38.02(19) . . . . ?
C008 C007 C00C C009 -1.30(15) . . . . ?
C008 C007 C00C C00I 179.34(12) . . . . ?
C008 C007 C00E C00F 0.5(2) . . . . ?
C008 C00G C00H C00F -1.4(2) . . . . ?
C009 N006 C008 C007 1.21(15) . . . . ?
C009 N006 C008 C00G -175.65(14) . . . . ?
C009 N006 C00A O003 26.2(2) . . . . ?
C009 N006 C00A C00D -150.62(12) . . . . ?
C009 C00C C00I C00B -100.34(16) . . . . ?
C00A N006 C008 C007 173.74(12) . . . . ?
C00A N006 C008 C00G -3.1(2) . . . . ?
C00A N006 C009 C00C -174.83(12) . . . . ?
C00A N006 C009 C00O 8.8(2) . . . . ?
C00A C00D C00J C00M -175.47(13) . . . . ?
C00A C00D C00K C00N 173.71(13) . . . . ?
C00C C007 C008 N006 0.01(15) . . . . ?
C00C C007 C008 C00G 177.29(12) . . . . ?
C00C C007 C00E C00F -178.77(13) . . . . ?
C00D C00J C00M C00L 2.2(2) . . . . ?
C00D C00K C00N C00L 1.0(2) . . . . ?
C00E C007 C008 N006 -179.38(12) . . . . ?
C00E C007 C008 C00G -2.1(2) . . . . ?
C00E C007 C00C C009 178.02(14) . . . . ?
C00E C007 C00C C00I -1.3(2) . . . . ?
C00E C00F C00H C00G -0.1(2) . . . . ?
C00J C00D C00K C00N -0.2(2) . . . . ?
C00K C00D C00J C00M -1.4(2) . . . . ?
C00M C00L C00N C00K -0.1(2) . . . . ?
C00N C00L C00M C00J -1.4(2) . . . . ?
C00O C009 C00C C007 178.13(13) . . . . ?
C00O C009 C00C C00I -2.6(2) . . . . ?
C00P O004 C00F C00E -5.6(2) . . . . ?
C00P O004 C00F C00H 173.24(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.545
_oxdiff_exptl_absorpt_empirical_full_min 0.728
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Paracetamol-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987511'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-24
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Paracetamol
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_melting_point          444K
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'
O O 0.0492 0.0322 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.08950(10)
_cell_length_b                   9.21120(10)
_cell_length_c                   11.59660(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.8900(10)
_cell_angle_gamma                90
_cell_volume                     750.122(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12179
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6850
_cell_measurement_theta_min      3.8260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13453
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.038
_diffrn_reflns_theta_min         6.159
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00  -7.00   0.50    0.05    --  -46.62 119.00-170.00  170
  2  ω     54.00 120.00   0.50    0.05    --   46.62 156.00 -14.00  132
  3  ω     79.00 178.00   0.50    0.05    --  105.44 119.00-170.00  198
  4  ω     90.00 178.00   0.50    0.05    --  105.44  30.00 120.00  176
  5  ω     31.00 114.00   0.50    0.05    --   46.62-156.00 -51.00  166
  6  ω     33.00 138.00   0.50    0.05    --  105.44-156.00 -51.00  210
  7  ω     33.00 113.00   0.50    0.05    --  105.44-119.00 104.00  160
  8  ω     33.00 129.00   0.50    0.05    --  105.44 -77.00  90.00  192
  9  ω     33.00 108.00   0.50    0.05    --  105.44 -94.00 -60.00  150
 10  ω     33.00 123.00   0.50    0.05    --  105.44 -61.00  60.00  180
 11  ω     33.00 108.00   0.50    0.05    --  105.44 -94.00 -30.00  150
 12  ω     11.00  92.00   0.50    0.05    --   46.62-119.00 104.00  162
 13  ω   -119.00 -50.00   0.50    0.05    --  -46.62-156.00 -51.00  138
 14  ω   -113.00 -27.00   0.50    0.05    -- -100.00 119.00-170.00  172
 15  ω   -115.00 -25.00   0.50    0.05    -- -100.00  30.00-120.00  180
 16  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00  30.00  192
 17  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00 120.00  192
 18  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00  30.00   96
 19  ω   -119.00 -30.00   0.50    0.05    --  -46.62 -57.00 -60.00  178
 20  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00-180.00   96
 21  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00-120.00  192
 22  ω   -117.00 -27.00   0.50    0.05    -- -100.00  61.00  30.00  180
 23  ω   -119.00 -74.00   0.50    0.05    --  -46.62 -57.00 150.00   90
 24  ω   -173.00 -75.00   0.50    0.05    -- -100.00-119.00 104.00  196
 25  ω   -166.00 -50.00   0.50    0.05    -- -100.00-156.00 -51.00  232
 26  ω   -173.00 -71.00   0.50    0.05    -- -100.00-125.00 150.00  204
 27  ω   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00   0.00  174
 28  ω   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00 -90.00  174
 29  ω   -173.00 -81.00   0.50    0.05    -- -100.00 -94.00-150.00  184
 30  ω   -137.00 -27.00   0.50    0.05    -- -100.00 156.00 -14.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0294235000
_diffrn_orient_matrix_UB_12      -0.1395671000
_diffrn_orient_matrix_UB_13      0.0685580000
_diffrn_orient_matrix_UB_21      -0.0905237000
_diffrn_orient_matrix_UB_22      0.0899099000
_diffrn_orient_matrix_UB_23      0.0901268000
_diffrn_orient_matrix_UB_31      -0.1975441000
_diffrn_orient_matrix_UB_32      -0.0203639000
_diffrn_orient_matrix_UB_33      -0.0719463000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1477
_reflns_number_total             1527
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.125
_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)+(0.0645P)²+0.2877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C006(H006), C008(H008), C009(H009), C00A(H00A)
2.b Idealised Me refined as rotating group:
 C00B(H00B,H00C,H00D)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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
O001 O 0.33525(11) 0.07681(10) 0.27741(7) 0.0195(2) Uani 1 1 d . . . . .
H001 H 0.437559 0.046599 0.261801 0.029 Uiso 1 1 calc R U . . .
O002 O 0.14680(11) 0.50575(10) 0.69137(8) 0.0208(2) Uani 1 1 d . . . . .
N003 N 0.44778(13) 0.44880(11) 0.66033(8) 0.0148(3) Uani 1 1 d . . . . .
H003 H 0.565806 0.464516 0.685591 0.018 Uiso 1 1 calc R U . . .
C004 C 0.41156(16) 0.35720(12) 0.56157(10) 0.0140(3) Uani 1 1 d . . . . .
C005 C 0.36642(16) 0.16918(13) 0.37062(10) 0.0152(3) Uani 1 1 d . . . . .
C006 C 0.21988(16) 0.26310(13) 0.39034(10) 0.0162(3) Uani 1 1 d . . . . .
H006 H 0.106181 0.262760 0.339683 0.019 Uiso 1 1 calc R U . . .
C007 C 0.32124(16) 0.51441(12) 0.71973(10) 0.0154(3) Uani 1 1 d . . . . .
C008 C 0.24201(16) 0.35713(12) 0.48487(10) 0.0157(3) Uani 1 1 d . . . . .
H008 H 0.143880 0.419922 0.496953 0.019 Uiso 1 1 calc R U . . .
C009 C 0.53750(16) 0.17173(13) 0.44576(11) 0.0179(3) Uani 1 1 d . . . . .
H009 H 0.636876 0.110807 0.432457 0.021 Uiso 1 1 calc R U . . .
C00A C 0.55943(16) 0.26499(13) 0.54020(10) 0.0169(3) Uani 1 1 d . . . . .
H00A H 0.673961 0.266328 0.590060 0.020 Uiso 1 1 calc R U . . .
C00B C 0.40712(17) 0.60122(14) 0.82380(11) 0.0210(3) Uani 1 1 d . . . . .
H00B H 0.396295 0.702882 0.805899 0.031 Uiso 1 1 calc R U . . .
H00C H 0.539038 0.575979 0.843226 0.031 Uiso 1 1 calc R U . . .
H00D H 0.340805 0.580160 0.888669 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 H001 0.8200 . ?
O001 C005 1.3694(14) . ?
O002 C007 1.2379(15) . ?
N003 H003 0.8600 . ?
N003 C004 1.4173(15) . ?
N003 C007 1.3469(15) . ?
C004 C008 1.3937(16) . ?
C004 C00A 1.3975(16) . ?
C005 C006 1.3948(16) . ?
C005 C009 1.3931(16) . ?
C006 H006 0.9300 . ?
C006 C008 1.3889(16) . ?
C007 C00B 1.5050(17) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C009 C00A 1.3839(17) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9600 . ?
C00B H00C 0.9600 . ?
C00B H00D 0.9600 . ?

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
C005 O001 H001 109.5 . . ?
C004 N003 H003 115.8 . . ?
C007 N003 H003 115.8 . . ?
C007 N003 C004 128.38(10) . . ?
C008 C004 N003 124.11(10) . . ?
C008 C004 C00A 119.26(11) . . ?
C00A C004 N003 116.61(10) . . ?
O001 C005 C006 118.14(10) . . ?
O001 C005 C009 122.44(10) . . ?
C009 C005 C006 119.41(11) . . ?
C005 C006 H006 119.7 . . ?
C008 C006 C005 120.68(10) . . ?
C008 C006 H006 119.7 . . ?
O002 C007 N003 123.13(11) . . ?
O002 C007 C00B 121.78(11) . . ?
N003 C007 C00B 115.09(10) . . ?
C004 C008 H008 120.1 . . ?
C006 C008 C004 119.87(10) . . ?
C006 C008 H008 120.1 . . ?
C005 C009 H009 120.0 . . ?
C00A C009 C005 119.94(11) . . ?
C00A C009 H009 120.0 . . ?
C004 C00A H00A 119.6 . . ?
C009 C00A C004 120.80(10) . . ?
C009 C00A H00A 119.6 . . ?
C007 C00B H00B 109.5 . . ?
C007 C00B H00C 109.5 . . ?
C007 C00B H00D 109.5 . . ?
H00B C00B H00C 109.5 . . ?
H00B C00B H00D 109.5 . . ?
H00C C00B H00D 109.5 . . ?

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
O001 C005 C006 C008 178.71(10) . . . . ?
O001 C005 C009 C00A -178.46(10) . . . . ?
N003 C004 C008 C006 -179.98(10) . . . . ?
N003 C004 C00A C009 -179.93(10) . . . . ?
C004 N003 C007 O002 -2.44(18) . . . . ?
C004 N003 C007 C00B 178.05(10) . . . . ?
C005 C006 C008 C004 -0.52(17) . . . . ?
C005 C009 C00A C004 0.05(18) . . . . ?
C006 C005 C009 C00A 1.22(18) . . . . ?
C007 N003 C004 C008 22.85(18) . . . . ?
C007 N003 C004 C00A -158.87(11) . . . . ?
C008 C004 C00A C009 -1.56(18) . . . . ?
C009 C005 C006 C008 -0.99(18) . . . . ?
C00A C004 C008 C006 1.78(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.469
_oxdiff_exptl_absorpt_empirical_full_min 0.590
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Gliclazide-100k-XOu
_database_code_depnum_ccdc_archive 'CCDC 1987345'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Gliclazide
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H21 N3 O3 S'
_chemical_formula_sum            'C15 H21 N3 O3 S'
_chemical_formula_weight         323.41
_chemical_melting_point          453K
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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.63520(10)
_cell_length_b                   14.32960(10)
_cell_length_c                   10.89950(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.6230(10)
_cell_angle_gamma                90
_cell_volume                     1591.64(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20589
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9800
_cell_measurement_theta_min      5.0990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29461
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.135
_diffrn_reflns_theta_min         5.124
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  69.00   0.50    0.07    --   46.37 -74.00   6.00  188
  2  ω     33.00 128.00   0.50    0.28    --  105.44 -74.00   6.00  190
  3  ω     33.00 108.00   0.50    0.28    --  105.44 -94.00 -30.00  150
  4  ω     33.00 117.00   0.50    0.28    --  105.44-125.00  90.00  168
  5  ω     33.00 108.00   0.50    0.28    --  105.44 -94.00 150.00  150
  6  ω     33.00 117.00   0.50    0.28    --  105.44-125.00   0.00  168
  7  ω     33.00 117.00   0.50    0.28    --  105.44-125.00 150.00  168
  8  ω     33.00 108.00   0.50    0.28    --  105.44 -94.00  90.00  150
  9  ω     33.00 123.00   0.50    0.28    --  105.44 -61.00   0.00  180
 10  ω     30.00 118.00   0.50    0.07    --   46.37  57.00-150.00  176
 11  ω     23.00  99.00   0.50    0.07    --   46.37  77.00 -60.00  152
 12  ω     30.00 118.00   0.50    0.07    --   46.37  57.00  60.00  176
 13  ω     83.00 178.00   0.50    0.28    --  105.44  74.00 135.00  190
 14  ω     33.00 108.00   0.50    0.28    --  105.44 -94.00-120.00  150
 15  ω     33.00 108.00   0.50    0.28    --  105.44 -94.00-150.00  150
 16  ω     24.00 118.00   0.50    0.07    --   46.37  74.00 135.00  188
 17  ω    -61.00  27.00   0.50    0.07    --  -46.37  38.00 120.00  176
 18  ω    -69.00  27.00   0.50    0.07    --  -46.37  74.00 135.00  192
 19  ω   -118.00 -24.00   0.50    0.07    --  -46.37 -74.00   6.00  188
 20  ω   -122.00 -27.00   0.50    0.28    -- -100.00  74.00 135.00  190
 21  ω   -173.00 -77.00   0.50    0.28    -- -100.00 -74.00   6.00  192
 22  ω   -118.00 -71.00   0.50    0.07    --  -46.37-125.00 -30.00   94
 23  ω   -118.00 -71.00   0.50    0.07    --  -46.37-125.00-120.00   94
 24  ω   -118.00 -71.00   0.50    0.07    --  -46.37-125.00  30.00   94
 25  ω   -118.00 -71.00   0.50    0.07    --  -46.37-125.00  60.00   94
 26  ω   -118.00 -71.00   0.50    0.07    --  -46.37-125.00 150.00   94
 27  ω   -172.00 -85.00   0.50    0.28    -- -100.00 -45.00 -60.00  174
 28  ω   -173.00 -81.00   0.50    0.28    -- -100.00 -94.00  90.00  184
 29  ω   -173.00 -82.00   0.50    0.28    -- -100.00 -61.00 -90.00  182
 30  ω   -172.00 -85.00   0.50    0.28    -- -100.00 -45.00-180.00  174
 31  ω   -175.00 -84.00   0.50    0.28    -- -100.00 -30.00-150.00  182
 32  ω   -175.00 -82.00   0.50    0.28    -- -100.00 -15.00-120.00  186
 33  ω   -173.00 -82.00   0.50    0.28    -- -100.00 -61.00  30.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0503064000
_diffrn_orient_matrix_UB_12      -0.0293965000
_diffrn_orient_matrix_UB_13      0.1134893000
_diffrn_orient_matrix_UB_21      0.0960767000
_diffrn_orient_matrix_UB_22      -0.0830356000
_diffrn_orient_matrix_UB_23      0.0268477000
_diffrn_orient_matrix_UB_31      0.1052168000
_diffrn_orient_matrix_UB_32      0.0617073000
_diffrn_orient_matrix_UB_33      0.0903367000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3059
_reflns_number_total             3260
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.098
_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)+(0.0859P)²+1.0801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1415
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00L), C00K(H00O)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00F), C00H(H00J,H00K), C00J(H00M,H00N), C00L(H00P,H00Q), C00M(H00R,
 H00S)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
2.d Idealised Me refined as rotating group:
 C00G(H00G,H00H,H00I)
;
_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
S001 S 0.65201(4) 0.41731(3) 0.65467(4) 0.01900(17) Uani 1 1 d . . . . .
O002 O 0.58010(14) 0.42259(9) 0.90055(12) 0.0243(3) Uani 1 1 d . . . . .
O003 O 0.77644(13) 0.41590(9) 0.74938(13) 0.0245(3) Uani 1 1 d . . . . .
O004 O 0.64318(13) 0.44989(9) 0.52759(12) 0.0232(3) Uani 1 1 d . . . . .
N005 N 0.46568(17) 0.55728(11) 0.84938(15) 0.0261(4) Uani 1 1 d . . . . .
H005 H 0.428110 0.551458 0.909126 0.031 Uiso 1 1 calc R U . . .
N006 N 0.55522(15) 0.48862(11) 0.70272(14) 0.0207(3) Uani 1 1 d . . . . .
H006 H 0.512911 0.530019 0.649681 0.025 Uiso 1 1 calc R U . . .
N007 N 0.45097(16) 0.64144(11) 0.77889(15) 0.0240(4) Uani 1 1 d . . . . .
C008 C 0.58269(17) 0.30490(12) 0.64207(17) 0.0198(4) Uani 1 1 d . . . . .
C009 C 0.53745(18) 0.48609(13) 0.82465(17) 0.0214(4) Uani 1 1 d . . . . .
C00A C 0.47381(18) 0.12668(13) 0.61856(18) 0.0237(4) Uani 1 1 d . . . . .
C00B C 0.61940(19) 0.24322(14) 0.74505(18) 0.0247(4) Uani 1 1 d . . . . .
H00B H 0.679555 0.261285 0.821452 0.030 Uiso 1 1 calc R U . . .
C00C C 0.49355(19) 0.27824(13) 0.52741(17) 0.0233(4) Uani 1 1 d . . . . .
H00C H 0.470395 0.319325 0.458546 0.028 Uiso 1 1 calc R U . . .
C00D C 0.43953(19) 0.18946(14) 0.51707(18) 0.0247(4) Uani 1 1 d . . . . .
H00D H 0.379165 0.171544 0.440720 0.030 Uiso 1 1 calc R U . . .
C00E C 0.5650(2) 0.15464(14) 0.73199(19) 0.0268(4) Uani 1 1 d . . . . .
H00E H 0.589812 0.113037 0.800158 0.032 Uiso 1 1 calc R U . . .
C00F C 0.31524(19) 0.67587(14) 0.74795(19) 0.0264(4) Uani 1 1 d . . . . .
H00A H 0.279808 0.667580 0.819939 0.032 Uiso 1 1 calc R U . . .
H00F H 0.259483 0.643407 0.674249 0.032 Uiso 1 1 calc R U . . .
C00G C 0.4122(2) 0.03134(14) 0.6059(2) 0.0287(4) Uani 1 1 d . . . . .
H00G H 0.350893 0.028614 0.655498 0.043 Uiso 1 1 calc R U . . .
H00H H 0.479300 -0.014830 0.636467 0.043 Uiso 1 1 calc R U . . .
H00I H 0.367207 0.019393 0.517548 0.043 Uiso 1 1 calc R U . . .
C00H C 0.5291(2) 0.71590(14) 0.8601(2) 0.0291(4) Uani 1 1 d . . . . .
H00J H 0.620376 0.712220 0.860724 0.035 Uiso 1 1 calc R U . . .
H00K H 0.524285 0.710851 0.947391 0.035 Uiso 1 1 calc R U . . .
C00I C 0.4679(2) 0.80632(15) 0.7996(2) 0.0295(4) Uani 1 1 d . . . . .
H00L H 0.517497 0.832555 0.744551 0.035 Uiso 1 1 calc R U . . .
C00J C 0.4518(2) 0.87940(15) 0.8991(2) 0.0339(5) Uani 1 1 d . . . . .
H00M H 0.514236 0.868194 0.982087 0.041 Uiso 1 1 calc R U . . .
H00N H 0.464305 0.942216 0.871532 0.041 Uiso 1 1 calc R U . . .
C00K C 0.3257(2) 0.77882(15) 0.7188(2) 0.0299(4) Uani 1 1 d . . . . .
H00O H 0.313384 0.788993 0.627226 0.036 Uiso 1 1 calc R U . . .
C00L C 0.2349(2) 0.84163(16) 0.7687(2) 0.0340(5) Uani 1 1 d . . . . .
H00P H 0.213137 0.897780 0.717303 0.041 Uiso 1 1 calc R U . . .
H00Q H 0.154257 0.809129 0.766630 0.041 Uiso 1 1 calc R U . . .
C00M C 0.3110(2) 0.86531(18) 0.9048(2) 0.0398(5) Uani 1 1 d . . . . .
H00R H 0.306360 0.814773 0.962511 0.048 Uiso 1 1 calc R U . . .
H00S H 0.277383 0.921774 0.933067 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O003 1.4268(14) . ?
S001 O004 1.4390(13) . ?
S001 N006 1.6391(15) . ?
S001 C008 1.7605(19) . ?
O002 C009 1.226(2) . ?
N005 H005 0.8600 . ?
N005 N007 1.414(2) . ?
N005 C009 1.347(2) . ?
N006 H006 0.8600 . ?
N006 C009 1.395(2) . ?
N007 C00F 1.471(2) . ?
N007 C00H 1.481(3) . ?
C008 C00B 1.394(3) . ?
C008 C00C 1.389(2) . ?
C00A C00D 1.391(3) . ?
C00A C00E 1.394(3) . ?
C00A C00G 1.504(3) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.385(3) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.387(3) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F H00A 0.9700 . ?
C00F H00F 0.9700 . ?
C00F C00K 1.520(3) . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00H H00J 0.9700 . ?
C00H H00K 0.9700 . ?
C00H C00I 1.514(3) . ?
C00I H00L 0.9800 . ?
C00I C00J 1.552(3) . ?
C00I C00K 1.567(3) . ?
C00J H00M 0.9700 . ?
C00J H00N 0.9700 . ?
C00J C00M 1.530(3) . ?
C00K H00O 0.9800 . ?
C00K C00L 1.530(3) . ?
C00L H00P 0.9700 . ?
C00L H00Q 0.9700 . ?
C00L C00M 1.511(3) . ?
C00M H00R 0.9700 . ?
C00M H00S 0.9700 . ?

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
O003 S001 O004 119.51(8) . . ?
O003 S001 N006 108.36(8) . . ?
O003 S001 C008 108.93(8) . . ?
O004 S001 N006 103.37(8) . . ?
O004 S001 C008 108.13(8) . . ?
N006 S001 C008 107.94(8) . . ?
N007 N005 H005 119.4 . . ?
C009 N005 H005 119.4 . . ?
C009 N005 N007 121.21(15) . . ?
S001 N006 H006 118.1 . . ?
C009 N006 S001 123.82(13) . . ?
C009 N006 H006 118.1 . . ?
N005 N007 C00F 111.07(15) . . ?
N005 N007 C00H 109.50(15) . . ?
C00F N007 C00H 103.98(15) . . ?
C00B C008 S001 120.19(14) . . ?
C00C C008 S001 118.99(14) . . ?
C00C C008 C00B 120.80(17) . . ?
O002 C009 N005 123.26(16) . . ?
O002 C009 N006 122.50(17) . . ?
N005 C009 N006 114.19(16) . . ?
C00D C00A C00E 118.48(18) . . ?
C00D C00A C00G 120.40(17) . . ?
C00E C00A C00G 121.11(17) . . ?
C008 C00B H00B 120.5 . . ?
C00E C00B C008 119.06(17) . . ?
C00E C00B H00B 120.5 . . ?
C008 C00C H00C 120.5 . . ?
C00D C00C C008 119.06(17) . . ?
C00D C00C H00C 120.5 . . ?
C00A C00D H00D 119.3 . . ?
C00C C00D C00A 121.35(17) . . ?
C00C C00D H00D 119.3 . . ?
C00A C00E H00E 119.4 . . ?
C00B C00E C00A 121.24(18) . . ?
C00B C00E H00E 119.4 . . ?
N007 C00F H00A 110.9 . . ?
N007 C00F H00F 110.9 . . ?
N007 C00F C00K 104.36(16) . . ?
H00A C00F H00F 108.9 . . ?
C00K C00F H00A 110.9 . . ?
C00K C00F H00F 110.9 . . ?
C00A C00G H00G 109.5 . . ?
C00A C00G H00H 109.5 . . ?
C00A C00G H00I 109.5 . . ?
H00G C00G H00H 109.5 . . ?
H00G C00G H00I 109.5 . . ?
H00H C00G H00I 109.5 . . ?
N007 C00H H00J 110.8 . . ?
N007 C00H H00K 110.8 . . ?
N007 C00H C00I 104.96(16) . . ?
H00J C00H H00K 108.8 . . ?
C00I C00H H00J 110.8 . . ?
C00I C00H H00K 110.8 . . ?
C00H C00I H00L 110.8 . . ?
C00H C00I C00J 113.10(18) . . ?
C00H C00I C00K 104.79(16) . . ?
C00J C00I H00L 110.8 . . ?
C00J C00I C00K 106.31(17) . . ?
C00K C00I H00L 110.8 . . ?
C00I C00J H00M 110.9 . . ?
C00I C00J H00N 110.9 . . ?
H00M C00J H00N 109.0 . . ?
C00M C00J C00I 104.10(18) . . ?
C00M C00J H00M 110.9 . . ?
C00M C00J H00N 110.9 . . ?
C00F C00K C00I 104.08(16) . . ?
C00F C00K H00O 111.2 . . ?
C00F C00K C00L 113.93(17) . . ?
C00I C00K H00O 111.2 . . ?
C00L C00K C00I 104.98(17) . . ?
C00L C00K H00O 111.2 . . ?
C00K C00L H00P 110.7 . . ?
C00K C00L H00Q 110.7 . . ?
H00P C00L H00Q 108.8 . . ?
C00M C00L C00K 105.39(17) . . ?
C00M C00L H00P 110.7 . . ?
C00M C00L H00Q 110.7 . . ?
C00J C00M H00R 110.9 . . ?
C00J C00M H00S 110.9 . . ?
C00L C00M C00J 104.26(18) . . ?
C00L C00M H00R 110.9 . . ?
C00L C00M H00S 110.9 . . ?
H00R C00M H00S 108.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S001 N006 C009 O002 -9.5(3) . . . . ?
S001 N006 C009 N005 172.79(13) . . . . ?
S001 C008 C00B C00E -178.96(15) . . . . ?
S001 C008 C00C C00D 179.56(14) . . . . ?
O003 S001 N006 C009 -49.26(17) . . . . ?
O003 S001 C008 C00B 24.67(17) . . . . ?
O003 S001 C008 C00C -153.90(14) . . . . ?
O004 S001 N006 C009 -177.03(15) . . . . ?
O004 S001 C008 C00B 156.00(15) . . . . ?
O004 S001 C008 C00C -22.58(17) . . . . ?
N005 N007 C00F C00K 159.86(15) . . . . ?
N005 N007 C00H C00I -158.47(16) . . . . ?
N006 S001 C008 C00B -92.79(16) . . . . ?
N006 S001 C008 C00C 88.64(15) . . . . ?
N007 N005 C009 O002 161.25(18) . . . . ?
N007 N005 C009 N006 -21.1(3) . . . . ?
N007 C00F C00K C00I -27.8(2) . . . . ?
N007 C00F C00K C00L -141.57(18) . . . . ?
N007 C00H C00I C00J 136.80(18) . . . . ?
N007 C00H C00I C00K 21.4(2) . . . . ?
C008 S001 N006 C009 68.56(16) . . . . ?
C008 C00B C00E C00A -0.6(3) . . . . ?
C008 C00C C00D C00A -0.6(3) . . . . ?
C009 N005 N007 C00F 138.46(18) . . . . ?
C009 N005 N007 C00H -107.26(19) . . . . ?
C00B C008 C00C C00D 1.0(3) . . . . ?
C00C C008 C00B C00E -0.4(3) . . . . ?
C00D C00A C00E C00B 1.0(3) . . . . ?
C00E C00A C00D C00C -0.4(3) . . . . ?
C00F N007 C00H C00I -39.71(19) . . . . ?
C00F C00K C00L C00M 87.1(2) . . . . ?
C00G C00A C00D C00C 178.96(18) . . . . ?
C00G C00A C00E C00B -178.35(18) . . . . ?
C00H N007 C00F C00K 42.17(19) . . . . ?
C00H C00I C00J C00M -95.0(2) . . . . ?
C00H C00I C00K C00F 3.8(2) . . . . ?
C00H C00I C00K C00L 123.78(18) . . . . ?
C00I C00J C00M C00L -35.8(2) . . . . ?
C00I C00K C00L C00M -26.1(2) . . . . ?
C00J C00I C00K C00F -116.22(18) . . . . ?
C00J C00I C00K C00L 3.8(2) . . . . ?
C00K C00I C00J C00M 19.4(2) . . . . ?
C00K C00L C00M C00J 38.9(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.735
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Felodipine-100k-HWRong
_database_code_depnum_ccdc_archive 'CCDC 1987340'
loop_
_audit_author_name
_audit_author_address
'Ming Lu'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Felodipine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 Cl2 N O4'
_chemical_formula_sum            'C18 H19 Cl2 N O4'
_chemical_formula_weight         384.24
_chemical_melting_point          418K
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'
O O 0.0492 0.0322 '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'
Cl Cl 0.3639 0.7018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0936(2)
_cell_length_b                   12.0624(2)
_cell_length_c                   13.4258(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.167(2)
_cell_angle_gamma                90
_cell_volume                     1757.80(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22811
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.8090
_cell_measurement_theta_min      3.6620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33252
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.979
_diffrn_reflns_theta_min         4.073
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00 -12.00   0.50    0.05    --  -46.37 127.00   9.00  168
  2  ω   -105.00 -20.00   0.50    0.05    --  -46.37 143.00 179.00  170
  3  ω   -118.00 -70.00   0.50    0.05    --  -46.37-127.00 -65.00   96
  4  ω   -118.00 -59.00   0.50    0.05    --  -46.37-143.00 124.00  118
  5  ω     64.00 118.00   0.50    0.05    --   46.37 143.00 179.00  108
  6  ω     25.00 106.00   0.50    0.05    --   46.37-143.00 124.00  162
  7  ω     16.00  96.00   0.50    0.05    --   46.37-127.00 -65.00  160
  8  ω   -130.00 -27.00   0.50    0.05    -- -100.00 143.00 179.00  206
  9  ω   -118.00 -27.00   0.50    0.05    -- -100.00 127.00   9.00  182
 10  ω   -173.00 -70.00   0.50    0.05    -- -100.00-127.00 -65.00  206
 11  ω     74.00 178.00   0.50    0.05    --  107.00 127.00   9.00  208
 12  ω     34.00 130.00   0.50    0.05    --  107.00-143.00 124.00  192
 13  ω     34.00 118.00   0.50    0.05    --  107.00-127.00 -65.00  168
 14  ω     64.00 176.00   0.50    0.05    --  107.00 143.00 179.00  224
 15  ω   -118.00 -71.00   0.50    0.05    --  -46.37-125.00   0.00   94
 16  ω   -118.00 -71.00   0.50    0.05    --  -46.37-125.00 150.00   94
 17  ω     30.00 118.00   0.50    0.05    --   46.37  57.00  90.00  176
 18  ω     30.00 118.00   0.50    0.05    --   46.37  57.00-180.00  176
 19  ω     30.00 118.00   0.50    0.05    --   46.37  57.00 -60.00  176
 20  ω   -175.00 -82.00   0.50    0.05    -- -100.00 -15.00-180.00  186
 21  ω   -114.00 -27.00   0.50    0.05    -- -100.00  45.00  60.00  174
 22  ω   -142.00-111.00   0.50    0.05    -- -100.00 -59.00  20.52   62
 23  ω   -173.00-147.00   0.50    0.05    -- -100.00 -59.00  20.52   52
 24  ω   -140.00-115.00   0.50    0.05    -- -100.00-143.00 124.00   50
 25  ω     74.00 117.00   0.50    0.05    --  107.00-125.00-150.00   86
 26  ω    132.00 178.00   0.50    0.05    --  107.00 125.00-120.00   92
 27  ω     35.00 120.00   0.50    0.05    --  107.00 -45.00 150.00  170
 28  ω     92.00 177.00   0.50    0.05    --  107.00  30.00-120.00  170
 29  ω     97.00 123.00   0.50    0.05    --  107.00 -61.00  90.00   52
 30  ω     82.00 121.00   0.50    0.05    --  107.00 -45.00  60.00   78
 31  ω     37.00  63.00   0.50    0.05    --  107.00-125.00-120.00   52
 32  ω     58.00  88.00   0.50    0.05    --  107.00 -61.00  90.00   60
 33  ω     60.00  85.00   0.50    0.05    --  107.00-125.00 -30.00   50
 34  ω     80.00 117.00   0.50    0.05    --  107.00-125.00-120.00   74
 35  ω    146.00 178.00   0.50    0.05    --  107.00 125.00  60.00   64
 36  ω     34.00 117.00   0.50    0.05    --  107.00-125.00   0.00  166
 37  ω     91.00 177.00   0.50    0.05    --  107.00  61.00 -90.00  172
 38  ω     35.00 103.00   0.50    0.05    --  107.00-125.00  90.00  136
 39  ω     62.00 113.00   0.50    0.05    --  107.00 -61.00 -60.00  102
 40  ω     34.00  76.00   0.50    0.05    --  107.00 -77.00  90.00   84
 41  ω     78.00 128.00   0.50    0.05    --  107.00 125.00  60.00  100
 42  ω     87.00 113.00   0.50    0.05    --  107.00-125.00  30.00   52
 43  ω     37.00  63.00   0.50    0.05    --  107.00-125.00  30.00   52
 44  ω     33.00 122.00   0.50    0.05    --  107.00 -30.00-120.00  178
 45  ω     35.00  72.00   0.50    0.05    --  107.00 -45.00  60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0642153000
_diffrn_orient_matrix_UB_12      0.1131037000
_diffrn_orient_matrix_UB_13      0.0126949000
_diffrn_orient_matrix_UB_21      0.1252284000
_diffrn_orient_matrix_UB_22      -0.0589806000
_diffrn_orient_matrix_UB_23      0.0393194000
_diffrn_orient_matrix_UB_31      -0.0187546000
_diffrn_orient_matrix_UB_32      -0.0073632000
_diffrn_orient_matrix_UB_33      -0.1209163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3515
_reflns_number_total             3658
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.344
_refine_diff_density_min         -1.384
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0782
_refine_ls_restrained_S_all      1.041
_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)+(0.0918P)²+4.4349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1983
_refine_ls_wR_factor_ref         0.1997
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00B,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C00D(H00D), C00K(H00K), C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00J(H00E,H00F,H00G), C00L(H00H,H00I,H00J), C00N(H00L,H00M,H00N), C00P(H00P,
 H00Q,H00R)
;
_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
Cl01 Cl 0.36433(10) 0.65016(8) 0.74914(7) 0.0479(3) Uani 1 1 d . . . . .
Cl02 Cl 0.64855(11) 0.61596(14) 0.83657(10) 0.0785(5) Uani 1 1 d . . . . .
O003 O 0.2295(2) 0.4287(2) 0.74872(17) 0.0350(5) Uani 1 1 d . . . . .
O004 O 0.2335(2) 0.70195(19) 0.49522(19) 0.0373(5) Uani 1 1 d . . . . .
O005 O 0.1227(3) 0.2713(2) 0.6977(2) 0.0475(7) Uani 1 1 d . . . . .
O006 O 0.1425(2) 0.6861(3) 0.3108(2) 0.0490(7) Uani 1 1 d . . . . .
N007 N 0.0530(3) 0.3561(2) 0.3671(2) 0.0354(6) Uani 1 1 d . . . . .
H007 H 0.019667 0.309513 0.313518 0.042 Uiso 1 1 calc R U . . .
C008 C 0.1380(3) 0.3891(3) 0.5602(2) 0.0260(6) Uani 1 1 d . . . . .
C009 C 0.3362(3) 0.4876(3) 0.5986(2) 0.0277(6) Uani 1 1 d . . . . .
C00A C 0.1958(3) 0.4977(3) 0.5486(2) 0.0264(6) Uani 1 1 d . . . . .
H00A H 0.175102 0.555785 0.588626 0.032 Uiso 1 1 calc R U . . .
C00B C 0.1598(3) 0.3538(3) 0.6723(2) 0.0281(6) Uani 1 1 d . . . . .
C00C C 0.0736(3) 0.3229(3) 0.4719(2) 0.0293(6) Uani 1 1 d . . . . .
C00D C 0.3867(3) 0.4099(3) 0.5536(2) 0.0298(6) Uani 1 1 d . . . . .
H00D H 0.334168 0.365526 0.495255 0.036 Uiso 1 1 calc R U . . .
C00E C 0.1451(3) 0.5317(3) 0.4263(2) 0.0286(6) Uani 1 1 d . . . . .
C00F C 0.1707(3) 0.6448(3) 0.4014(3) 0.0319(7) Uani 1 1 d . . . . .
C00G C 0.0827(3) 0.4592(3) 0.3434(2) 0.0322(7) Uani 1 1 d . . . . .
C00H C 0.4176(3) 0.5521(3) 0.6868(3) 0.0356(7) Uani 1 1 d . . . . .
C00I C 0.2760(3) 0.3969(3) 0.8636(3) 0.0378(8) Uani 1 1 d . . . . .
H00B H 0.226500 0.337170 0.871246 0.045 Uiso 1 1 calc R U . . .
H00C H 0.272075 0.459329 0.907495 0.045 Uiso 1 1 calc R U . . .
C00J C 0.0183(3) 0.2117(3) 0.4736(3) 0.0368(7) Uani 1 1 d . . . . .
H00E H -0.034081 0.188851 0.398938 0.055 Uiso 1 1 calc R U . . .
H00F H -0.029241 0.216867 0.514814 0.055 Uiso 1 1 calc R U . . .
H00G H 0.082956 0.158238 0.508079 0.055 Uiso 1 1 calc R U . . .
C00K C 0.5127(3) 0.3966(3) 0.5933(3) 0.0399(8) Uani 1 1 d . . . . .
H00K H 0.543490 0.344533 0.560949 0.048 Uiso 1 1 calc R U . . .
C00L C 0.0372(3) 0.4794(3) 0.2210(3) 0.0401(8) Uani 1 1 d . . . . .
H00H H 0.007196 0.411197 0.181338 0.060 Uiso 1 1 calc R U . . .
H00I H 0.103565 0.507001 0.207157 0.060 Uiso 1 1 calc R U . . .
H00J H -0.028268 0.532930 0.196408 0.060 Uiso 1 1 calc R U . . .
C00M C 0.5451(3) 0.5373(4) 0.7263(3) 0.0466(9) Uani 1 1 d . . . . .
C00N C 0.2669(4) 0.8148(3) 0.4843(4) 0.0449(9) Uani 1 1 d . . . . .
H00L H 0.195534 0.853822 0.432476 0.067 Uiso 1 1 calc R U . . .
H00M H 0.328950 0.814517 0.458029 0.067 Uiso 1 1 calc R U . . .
H00N H 0.298417 0.850876 0.555253 0.067 Uiso 1 1 calc R U . . .
C00O C 0.5919(3) 0.4598(4) 0.6797(3) 0.0485(10) Uani 1 1 d . . . . .
H00O H 0.676553 0.450645 0.706804 0.058 Uiso 1 1 calc R U . . .
C00P C 0.4036(5) 0.3605(6) 0.9026(5) 0.0778(16) Uani 1 1 d . . . . .
H00P H 0.405832 0.294455 0.863561 0.117 Uiso 1 1 calc R U . . .
H00Q H 0.438459 0.345317 0.980686 0.117 Uiso 1 1 calc R U . . .
H00R H 0.450349 0.417793 0.888964 0.117 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00H 1.729(4) . ?
Cl02 C00M 1.739(4) . ?
O003 C00B 1.348(4) . ?
O003 C00I 1.442(4) . ?
O004 C00F 1.340(4) . ?
O004 C00N 1.445(4) . ?
O005 C00B 1.200(4) . ?
O006 C00F 1.216(4) . ?
N007 H007 0.8600 . ?
N007 C00C 1.376(4) . ?
N007 C00G 1.370(5) . ?
C008 C00A 1.525(4) . ?
C008 C00B 1.471(4) . ?
C008 C00C 1.354(4) . ?
C009 C00A 1.531(4) . ?
C009 C00D 1.393(4) . ?
C009 C00H 1.396(4) . ?
C00A H00A 0.9800 . ?
C00A C00E 1.534(4) . ?
C00C C00J 1.504(5) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.384(4) . ?
C00E C00F 1.469(5) . ?
C00E C00G 1.354(5) . ?
C00G C00L 1.505(4) . ?
C00H C00M 1.404(5) . ?
C00I H00B 0.9700 . ?
C00I H00C 0.9700 . ?
C00I C00P 1.462(6) . ?
C00J H00E 0.9600 . ?
C00J H00F 0.9600 . ?
C00J H00G 0.9600 . ?
C00K H00K 0.9300 . ?
C00K C00O 1.365(6) . ?
C00L H00H 0.9600 . ?
C00L H00I 0.9600 . ?
C00L H00J 0.9600 . ?
C00M C00O 1.376(6) . ?
C00N H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9600 . ?
C00P H00Q 0.9600 . ?
C00P H00R 0.9600 . ?

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
C00B O003 C00I 117.0(3) . . ?
C00F O004 C00N 117.2(3) . . ?
C00C N007 H007 118.2 . . ?
C00G N007 H007 118.2 . . ?
C00G N007 C00C 123.6(3) . . ?
C00B C008 C00A 118.0(3) . . ?
C00C C008 C00A 122.0(3) . . ?
C00C C008 C00B 119.9(3) . . ?
C00D C009 C00A 118.5(3) . . ?
C00D C009 C00H 117.6(3) . . ?
C00H C009 C00A 123.9(3) . . ?
C008 C00A C009 110.9(2) . . ?
C008 C00A H00A 108.6 . . ?
C008 C00A C00E 110.8(2) . . ?
C009 C00A H00A 108.6 . . ?
C009 C00A C00E 109.4(2) . . ?
C00E C00A H00A 108.6 . . ?
O003 C00B C008 110.7(3) . . ?
O005 C00B O003 121.7(3) . . ?
O005 C00B C008 127.6(3) . . ?
N007 C00C C00J 113.2(3) . . ?
C008 C00C N007 119.9(3) . . ?
C008 C00C C00J 126.9(3) . . ?
C009 C00D H00D 119.0 . . ?
C00K C00D C009 122.0(3) . . ?
C00K C00D H00D 119.0 . . ?
C00F C00E C00A 117.8(3) . . ?
C00G C00E C00A 121.4(3) . . ?
C00G C00E C00F 120.7(3) . . ?
O004 C00F C00E 110.7(3) . . ?
O006 C00F O004 121.5(3) . . ?
O006 C00F C00E 127.9(3) . . ?
N007 C00G C00L 113.2(3) . . ?
C00E C00G N007 120.3(3) . . ?
C00E C00G C00L 126.5(3) . . ?
C009 C00H Cl01 121.2(3) . . ?
C009 C00H C00M 119.7(3) . . ?
C00M C00H Cl01 119.1(3) . . ?
O003 C00I H00B 110.0 . . ?
O003 C00I H00C 110.0 . . ?
O003 C00I C00P 108.3(3) . . ?
H00B C00I H00C 108.4 . . ?
C00P C00I H00B 110.0 . . ?
C00P C00I H00C 110.0 . . ?
C00C C00J H00E 109.5 . . ?
C00C C00J H00F 109.5 . . ?
C00C C00J H00G 109.5 . . ?
H00E C00J H00F 109.5 . . ?
H00E C00J H00G 109.5 . . ?
H00F C00J H00G 109.5 . . ?
C00D C00K H00K 119.9 . . ?
C00O C00K C00D 120.2(3) . . ?
C00O C00K H00K 119.9 . . ?
C00G C00L H00H 109.5 . . ?
C00G C00L H00I 109.5 . . ?
C00G C00L H00J 109.5 . . ?
H00H C00L H00I 109.5 . . ?
H00H C00L H00J 109.5 . . ?
H00I C00L H00J 109.5 . . ?
C00H C00M Cl02 120.6(3) . . ?
C00O C00M Cl02 118.2(3) . . ?
C00O C00M C00H 121.2(3) . . ?
O004 C00N H00L 109.5 . . ?
O004 C00N H00M 109.5 . . ?
O004 C00N H00N 109.5 . . ?
H00L C00N H00M 109.5 . . ?
H00L C00N H00N 109.5 . . ?
H00M C00N H00N 109.5 . . ?
C00K C00O C00M 119.4(3) . . ?
C00K C00O H00O 120.3 . . ?
C00M C00O H00O 120.3 . . ?
C00I C00P H00P 109.5 . . ?
C00I C00P H00Q 109.5 . . ?
C00I C00P H00R 109.5 . . ?
H00P C00P H00Q 109.5 . . ?
H00P C00P H00R 109.5 . . ?
H00Q C00P H00R 109.5 . . ?

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 C00H C00M Cl02 0.1(4) . . . . ?
Cl01 C00H C00M C00O 179.6(3) . . . . ?
Cl02 C00M C00O C00K 179.7(3) . . . . ?
C008 C00A C00E C00F 167.5(2) . . . . ?
C008 C00A C00E C00G -14.8(4) . . . . ?
C009 C00A C00E C00F -70.0(3) . . . . ?
C009 C00A C00E C00G 107.7(3) . . . . ?
C009 C00D C00K C00O 0.7(5) . . . . ?
C009 C00H C00M Cl02 -179.6(3) . . . . ?
C009 C00H C00M C00O -0.1(5) . . . . ?
C00A C008 C00B O003 0.9(4) . . . . ?
C00A C008 C00B O005 -179.6(3) . . . . ?
C00A C008 C00C N007 -3.6(4) . . . . ?
C00A C008 C00C C00J 176.5(3) . . . . ?
C00A C009 C00D C00K 179.2(3) . . . . ?
C00A C009 C00H Cl01 0.8(4) . . . . ?
C00A C009 C00H C00M -179.5(3) . . . . ?
C00A C00E C00F O004 -2.2(4) . . . . ?
C00A C00E C00F O006 177.4(3) . . . . ?
C00A C00E C00G N007 6.2(4) . . . . ?
C00A C00E C00G C00L -174.9(3) . . . . ?
C00B O003 C00I C00P 99.2(4) . . . . ?
C00B C008 C00A C009 68.5(3) . . . . ?
C00B C008 C00A C00E -169.8(2) . . . . ?
C00B C008 C00C N007 179.9(3) . . . . ?
C00B C008 C00C C00J 0.0(5) . . . . ?
C00C N007 C00G C00E 5.9(5) . . . . ?
C00C N007 C00G C00L -173.1(3) . . . . ?
C00C C008 C00A C009 -108.1(3) . . . . ?
C00C C008 C00A C00E 13.6(4) . . . . ?
C00C C008 C00B O003 177.5(3) . . . . ?
C00C C008 C00B O005 -2.9(5) . . . . ?
C00D C009 C00A C008 61.2(3) . . . . ?
C00D C009 C00A C00E -61.3(3) . . . . ?
C00D C009 C00H Cl01 -179.5(2) . . . . ?
C00D C009 C00H C00M 0.3(5) . . . . ?
C00D C00K C00O C00M -0.5(6) . . . . ?
C00F C00E C00G N007 -176.2(3) . . . . ?
C00F C00E C00G C00L 2.7(5) . . . . ?
C00G N007 C00C C008 -7.3(5) . . . . ?
C00G N007 C00C C00J 172.6(3) . . . . ?
C00G C00E C00F O004 -179.9(3) . . . . ?
C00G C00E C00F O006 -0.3(5) . . . . ?
C00H C009 C00A C008 -119.1(3) . . . . ?
C00H C009 C00A C00E 118.4(3) . . . . ?
C00H C009 C00D C00K -0.6(5) . . . . ?
C00H C00M C00O C00K 0.2(6) . . . . ?
C00I O003 C00B O005 10.7(4) . . . . ?
C00I O003 C00B C008 -169.8(3) . . . . ?
C00N O004 C00F O006 -0.3(4) . . . . ?
C00N O004 C00F C00E 179.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.576
_oxdiff_exptl_absorpt_empirical_full_min 0.509
_exptl_crystal_recrystallization_method 'From the Melt'
