data_3b
_audit_creation_date               2021-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C19 H22 Cl N O4'
_chemical_formula_sum              'C19 H22 Cl N O4'
_chemical_formula_weight           363.83
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl' 'Cl' 0.1484 0.1585 '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 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x+1/2, y+1/2, -z+1/2'
 3 '-x, -y, -z'
 4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     10.1138(7)
_cell_length_b                     7.5024(5)
_cell_length_c                     24.5925(17)
_cell_angle_alpha                  90.00
_cell_angle_beta                   97.092(3)
_cell_angle_gamma                  90.00
_cell_volume                       1851.7(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      22444
_cell_measurement_temperature      300(2)
_cell_measurement_theta_max        28.32
_cell_measurement_theta_min        2.29
_exptl_absorpt_coefficient_mu      0.229
_exptl_absorpt_correction_T_max    0.9454
_exptl_absorpt_correction_T_min    0.9219
_exptl_absorpt_correction_type     ?
_exptl_absorpt_process_details     ?
_exptl_crystal_colour              'pale yellow'
_exptl_crystal_density_diffrn      1.305
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         'plate'
_exptl_crystal_F_000               768
_exptl_crystal_size_max            0.361
_exptl_crystal_size_mid            0.28
_exptl_crystal_size_min            0.248
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents    0.0412
_diffrn_reflns_av_unetI/netI       0.0355
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -10
_diffrn_reflns_limit_l_max         32
_diffrn_reflns_limit_l_min         -32
_diffrn_reflns_number              22444
_diffrn_reflns_theta_full          28.32
_diffrn_reflns_theta_max           28.32
_diffrn_reflns_theta_min           2.29
_diffrn_ambient_temperature        300.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'fine-focus sealed tube'
_diffrn_standards_decay_%          ?
_diffrn_standards_interval_count   ?
_diffrn_standards_interval_time    ?
_diffrn_standards_number           ?
_reflns_number_gt                  2647
_reflns_number_total               4583
_reflns_threshold_expression       >2sigma(I)
_computing_cell_refinement         ?
_computing_data_collection         ?
_computing_data_reduction          ?
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution      'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max           0.463
_refine_diff_density_min           -0.367
_refine_diff_density_rms           0.045
_refine_ls_extinction_coef         0.011(3)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       SHELXL
_refine_ls_goodness_of_fit_ref     1.019
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       235
_refine_ls_number_reflns           4583
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1118
_refine_ls_R_factor_gt             0.0618
_refine_ls_restrained_S_all        1.019
_refine_ls_shift/su_max            0.023
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'calc w=1/[σ²(Fo²)+(0.0842P)²+1.0632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1597
_refine_ls_wR_factor_ref           0.2019
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00I,H00K), C00N(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00J(H00J), C00L(H00L)
2.d Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00C), C00K(H00D,H00E,H00H), C00O(H00O,H00P,H00Q), C00P(H00R,
 H00S,H00T)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     difmap
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_calc_flag
  _atom_site_disorder_assembly
  _atom_site_disorder_group
  _atom_site_refinement_flags_posn
 Cl1 Cl 0.96518(10) 0.23325(15) 0.23413(4) 0.0942(4) Uani 1 d . . .
 O2 O 0.7665(2) 0.0684(2) 0.49164(8) 0.0650(6) Uani 1 d . . .
 O3 O 0.9065(3) 0.2505(3) 0.54175(9) 0.0779(7) Uani 1 d . . .
 O4 O 0.3462(2) 0.5653(3) 0.35679(10) 0.0831(7) Uani 1 d . . .
 N006 N 0.6869(2) 0.6823(3) 0.47117(10) 0.0554(6) Uani 1 d . . .
 O5 O 0.4205(2) 0.2849(3) 0.35987(9) 0.0729(6) Uani 1 d . . .
 C007 C 0.7307(2) 0.3130(3) 0.37711(10) 0.0468(6) Uani 1 d . . .
 C008 C 0.7411(2) 0.3780(3) 0.47764(9) 0.0443(5) Uani 1 d . . .
 C009 C 0.6500(2) 0.3421(3) 0.42486(10) 0.0465(6) Uani 1 d . . .
 H009 H 0.6002 0.2325 0.4299 0.056 Uiso 1 calc . . R
 C00A C 0.5498(2) 0.4927(3) 0.41277(10) 0.0480(6) Uani 1 d . . .
 C00B C 0.8032(3) 0.2187(3) 0.50385(10) 0.0492(6) Uani 1 d . . .
 C00C C 0.7610(2) 0.5453(3) 0.49723(10) 0.0477(6) Uani 1 d . . .
 C00D C 0.5750(3) 0.6559(3) 0.43403(11) 0.0510(6) Uani 1 d . . .
 C00E C 0.4295(3) 0.4582(4) 0.37449(11) 0.0572(7) Uani 1 d . . .
 C00F C 0.8210(3) 0.4371(4) 0.36406(11) 0.0627(7) Uani 1 d . . .
 H00F H 0.8333 0.5405 0.3849 0.075 Uiso 1 calc . . R
 C00G C 0.7162(3) 0.1620(4) 0.34534(13) 0.0702(9) Uani 1 d . . .
 H00G H 0.6564 0.0746 0.3535 0.084 Uiso 1 calc . . R
 C00H C 0.8751(3) 0.2632(4) 0.28956(11) 0.0615(7) Uani 1 d . . .
 C00I C 0.8538(3) 0.6064(4) 0.54564(12) 0.0627(7) Uani 1 d . . .
 H00A H 0.9441 0.5951 0.5378 0.094 Uiso 1 calc . . GR
 H00B H 0.8412 0.5344 0.5769 0.094 Uiso 1 calc . . GR
 H00C H 0.8356 0.7288 0.5533 0.094 Uiso 1 calc . . GR
 C00J C 0.8946(3) 0.4132(4) 0.32069(13) 0.0714(8) Uani 1 d . . .
 H00J H 0.9565 0.4984 0.3130 0.086 Uiso 1 calc . . R
 C00K C 0.4929(3) 0.8212(4) 0.42296(15) 0.0709(8) Uani 1 d . . .
 H00D H 0.4738 0.8387 0.3841 0.106 Uiso 1 calc . . GR
 H00E H 0.5414 0.9219 0.4391 0.106 Uiso 1 calc . . GR
 H00H H 0.4110 0.8087 0.4385 0.106 Uiso 1 calc . . GR
 C00L C 0.7880(3) 0.1361(5) 0.30165(13) 0.0767(9) Uani 1 d . . .
 H00L H 0.7767 0.0326 0.2808 0.092 Uiso 1 calc . . R
 C00M C 0.9672(4) 0.1025(5) 0.57340(15) 0.0925(12) Uani 1 d . . .
 H00I H 0.9506 -0.0073 0.5529 0.111 Uiso 1 calc . . R
 H00K H 1.0628 0.1202 0.5803 0.111 Uiso 1 calc . . R
 C00N C 0.3161(4) 0.2355(6) 0.31693(16) 0.0940(12) Uani 1 d . . .
 H00M H 0.2860 0.1157 0.3236 0.113 Uiso 1 calc . . R
 H00N H 0.2411 0.3156 0.3177 0.113 Uiso 1 calc . . R
 C00O C 0.3604(5) 0.2425(8) 0.26399(18) 0.1254(18) Uani 1 d . . .
 H00O H 0.2899 0.2037 0.2368 0.188 Uiso 1 calc . . GR
 H00P H 0.4362 0.1659 0.2634 0.188 Uiso 1 calc . . GR
 H00Q H 0.3848 0.3627 0.2562 0.188 Uiso 1 calc . . GR
 C00P C 0.9145(7) 0.0898(8) 0.6229(2) 0.162(3) Uani 1 d . . .
 H00R H 0.9194 0.2040 0.6407 0.243 Uiso 1 calc . . GR
 H00S H 0.9646 0.0042 0.6460 0.243 Uiso 1 calc . . GR
 H00T H 0.8232 0.0525 0.6161 0.243 Uiso 1 calc . . GR
 H1 H 0.708(3) 0.784(5) 0.4833(13) 0.071(10) Uiso 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
 Cl1 C00H 1.745(3) . ?
 O2 C00B 1.214(3) . ?
 O3 C00B 1.333(3) . ?
 O3 C00M 1.448(4) . ?
 O4 C00E 1.206(3) . ?
 N006 C00C 1.382(3) . ?
 N006 C00D 1.378(4) . ?
 N006 H1 0.84(3) . ?
 O5 C00E 1.349(4) . ?
 O5 C00N 1.446(4) . ?
 C007 C009 1.526(3) . ?
 C007 C00F 1.370(4) . ?
 C007 C00G 1.374(4) . ?
 C008 C009 1.520(3) . ?
 C008 C00B 1.462(3) . ?
 C008 C00C 1.350(3) . ?
 C009 H009 0.9800 . ?
 C009 C00A 1.522(3) . ?
 C00A C00D 1.344(4) . ?
 C00A C00E 1.467(4) . ?
 C00C C00I 1.494(4) . ?
 C00D C00K 1.498(4) . ?
 C00F H00F 0.9300 . ?
 C00F C00J 1.386(4) . ?
 C00G H00G 0.9300 . ?
 C00G C00L 1.383(4) . ?
 C00H C00J 1.362(4) . ?
 C00H C00L 1.356(5) . ?
 C00I H00A 0.9600 . ?
 C00I H00B 0.9600 . ?
 C00I H00C 0.9600 . ?
 C00J H00J 0.9300 . ?
 C00K H00D 0.9600 . ?
 C00K H00E 0.9600 . ?
 C00K H00H 0.9600 . ?
 C00L H00L 0.9300 . ?
 C00M H00I 0.9700 . ?
 C00M H00K 0.9700 . ?
 C00M C00P 1.391(6) . ?
 C00N H00M 0.9700 . ?
 C00N H00N 0.9700 . ?
 C00N C00O 1.429(6) . ?
 C00O H00O 0.9600 . ?
 C00O H00P 0.9600 . ?
 C00O H00Q 0.9600 . ?
 C00P H00R 0.9600 . ?
 C00P H00S 0.9600 . ?
 C00P H00T 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 O3 C00M 118.9(2) . . ?
 C00C N006 H1 115(2) . . ?
 C00D N006 C00C 123.7(2) . . ?
 C00D N006 H1 121(2) . . ?
 C00E O5 C00N 117.4(3) . . ?
 C00F C007 C009 121.2(2) . . ?
 C00F C007 C00G 117.1(2) . . ?
 C00G C007 C009 121.7(2) . . ?
 C00B C008 C009 114.5(2) . . ?
 C00C C008 C009 121.1(2) . . ?
 C00C C008 C00B 124.4(2) . . ?
 C007 C009 H009 107.9 . . ?
 C008 C009 C007 110.91(19) . . ?
 C008 C009 H009 107.9 . . ?
 C008 C009 C00A 110.74(19) . . ?
 C00A C009 C007 111.24(19) . . ?
 C00A C009 H009 107.9 . . ?
 C00D C00A C009 120.7(2) . . ?
 C00D C00A C00E 120.9(2) . . ?
 C00E C00A C009 118.3(2) . . ?
 O2 C00B O3 121.9(2) . . ?
 O2 C00B C008 123.3(2) . . ?
 O3 C00B C008 114.8(2) . . ?
 N006 C00C C00I 113.1(2) . . ?
 C008 C00C N006 118.5(2) . . ?
 C008 C00C C00I 128.4(2) . . ?
 N006 C00D C00K 113.1(2) . . ?
 C00A C00D N006 119.3(2) . . ?
 C00A C00D C00K 127.5(3) . . ?
 O4 C00E O5 121.7(3) . . ?
 O4 C00E C00A 126.9(3) . . ?
 O5 C00E C00A 111.4(2) . . ?
 C007 C00F H00F 119.0 . . ?
 C007 C00F C00J 122.0(3) . . ?
 C00J C00F H00F 119.0 . . ?
 C007 C00G H00G 119.1 . . ?
 C007 C00G C00L 121.9(3) . . ?
 C00L C00G H00G 119.1 . . ?
 C00J C00H Cl1 119.5(2) . . ?
 C00L C00H Cl1 119.8(2) . . ?
 C00L C00H C00J 120.8(3) . . ?
 C00C C00I H00A 109.5 . . ?
 C00C C00I H00B 109.5 . . ?
 C00C C00I H00C 109.5 . . ?
 H00A C00I H00B 109.5 . . ?
 H00A C00I H00C 109.5 . . ?
 H00B C00I H00C 109.5 . . ?
 C00F C00J H00J 120.5 . . ?
 C00H C00J C00F 119.0(3) . . ?
 C00H C00J H00J 120.5 . . ?
 C00D C00K H00D 109.5 . . ?
 C00D C00K H00E 109.5 . . ?
 C00D C00K H00H 109.5 . . ?
 H00D C00K H00E 109.5 . . ?
 H00D C00K H00H 109.5 . . ?
 H00E C00K H00H 109.5 . . ?
 C00G C00L H00L 120.3 . . ?
 C00H C00L C00G 119.3(3) . . ?
 C00H C00L H00L 120.3 . . ?
 O3 C00M H00I 109.7 . . ?
 O3 C00M H00K 109.7 . . ?
 H00I C00M H00K 108.2 . . ?
 C00P C00M O3 109.9(3) . . ?
 C00P C00M H00I 109.7 . . ?
 C00P C00M H00K 109.7 . . ?
 O5 C00N H00M 109.2 . . ?
 O5 C00N H00N 109.2 . . ?
 H00M C00N H00N 107.9 . . ?
 C00O C00N O5 111.9(3) . . ?
 C00O C00N H00M 109.2 . . ?
 C00O C00N H00N 109.2 . . ?
 C00N C00O H00O 109.5 . . ?
 C00N C00O H00P 109.5 . . ?
 C00N C00O H00Q 109.5 . . ?
 H00O C00O H00P 109.5 . . ?
 H00O C00O H00Q 109.5 . . ?
 H00P C00O H00Q 109.5 . . ?
 C00M C00P H00R 109.5 . . ?
 C00M C00P H00S 109.5 . . ?
 C00M C00P H00T 109.5 . . ?
 H00R C00P H00S 109.5 . . ?
 H00R C00P H00T 109.5 . . ?
 H00S C00P H00T 109.5 . . ?


_olex2_submission_special_instructions  'No special instructions were received'
