#------------------------------------------------------------------------------
#$Date: 2019-11-24 07:34:30 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237138 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/43/1554339.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1554339
loop_
_publ_author_name
'Olivon, F.'
'Apel, C.'
'Retailleau, P.'
'Allard, P. M.'
'Wolfender, J. L.'
'Touboul, D.'
'Roussi, F.'
'Litaudon, M.'
'Desrat, S.'
_publ_section_title
;
 Searching for original natural products by molecular networking:
 detection, isolation and total synthesis of chloroaustralasines
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2171
_journal_paper_doi               10.1039/C8QO00429C
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C20 H24 Cl N O5'
_chemical_formula_sum            'C20 H24 Cl N O5'
_chemical_formula_weight         393.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2017-12-04 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.784(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3027(5)
_cell_length_b                   7.2512(2)
_cell_length_c                   23.1020(16)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      3.9
_cell_volume                     1871.19(17)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Rigaku Rapid2 IP'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type
;
Rigaku mm007HF
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  'OSMIC CMF Confocal'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9812
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.191
_diffrn_reflns_theta_min         3.872
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Reqab (Higashi,Rigaku, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       platelet
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ether/methanol'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0463
_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)+(0.0621P)²+0.2619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2563
_reflns_number_total             3350
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo00429c2.cif
_cod_data_source_block           compound_17
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1554339
_shelx_shelxl_version_number     2017/1
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N1 N 0.66926(15) 0.5990(2) 0.64851(8) 0.0366(5) Uani 1 1 d . .
O1 O 0.57952(13) 0.6258(2) 0.55384(7) 0.0460(4) Uani 1 1 d . .
Cl1 Cl 0.45313(4) 0.87822(7) 0.65581(2) 0.03760(18) Uani 1 1 d . .
C2 C 0.57318(18) 0.6208(3) 0.60623(9) 0.0331(5) Uani 1 1 d . .
O2 O 0.47077(13) 0.3269(2) 0.65751(7) 0.0393(4) Uani 1 1 d . .
H2O H 0.437(2) 0.323(4) 0.6244(11) 0.059 Uiso 1 1 d . U
C3 C 0.45227(17) 0.6448(3) 0.62794(9) 0.0287(5) Uani 1 1 d . .
C4 C 0.44790(16) 0.5055(3) 0.67830(9) 0.0311(5) Uani 1 1 d . .
C5 C 0.5385(2) 0.5478(3) 0.78502(9) 0.0410(6) Uani 1 1 d . .
H5 H 0.465010 0.520442 0.796418 0.049 Uiso 1 1 calc R U
C6 C 0.6364(2) 0.5876(3) 0.82694(11) 0.0514(7) Uani 1 1 d . .
H6 H 0.628459 0.588673 0.866411 0.062 Uiso 1 1 calc R U
C7 C 0.7458(2) 0.6256(3) 0.81006(12) 0.0538(7) Uani 1 1 d . .
H7 H 0.811848 0.649407 0.838309 0.065 Uiso 1 1 calc R U
C8 C 0.7576(2) 0.6285(3) 0.75162(10) 0.0441(6) Uani 1 1 d . .
H8 H 0.831559 0.654643 0.740542 0.053 Uiso 1 1 calc R U
C9 C 0.78816(19) 0.5848(3) 0.63033(11) 0.0491(7) Uani 1 1 d . .
H9A H 0.832819 0.487814 0.651918 0.074 Uiso 1 1 calc R U
H9AB H 0.830074 0.699509 0.638003 0.074 Uiso 1 1 calc R U
H9AC H 0.779168 0.557964 0.589198 0.074 Uiso 1 1 calc R U
C1' C 0.2220(2) 0.8634(3) 0.50864(10) 0.0425(6) Uani 1 1 d . .
O1' O 0.27485(15) 0.7219(2) 0.47604(6) 0.0516(5) Uani 1 1 d . .
C2' C 0.33530(19) 0.7741(3) 0.53324(9) 0.0381(5) Uani 1 1 d . .
H2' H 0.407636 0.849064 0.533908 0.046 Uiso 1 1 calc R U
O2' O 0.34765(13) 0.4441(2) 0.55468(6) 0.0376(4) Uani 1 1 d . .
H2'O H 0.379(2) 0.445(4) 0.5262(11) 0.056 Uiso 1 1 d . U
C3' C 0.34143(17) 0.6229(3) 0.58010(9) 0.0306(5) Uani 1 1 d . .
O3' O 0.34070(11) 0.5144(2) 0.70125(5) 0.0366(4) Uani 1 1 d . .
C4' C 0.22831(17) 0.6324(3) 0.60999(9) 0.0346(5) Uani 1 1 d . .
H4' H 0.227901 0.756585 0.626665 0.041 Uiso 1 1 calc R U
C5' C 0.11786(19) 0.6230(3) 0.56228(10) 0.0437(6) Uani 1 1 d . .
H5'A H 0.125840 0.521251 0.535901 0.052 Uiso 1 1 calc R U
H5'B H 0.046470 0.602990 0.580011 0.052 Uiso 1 1 calc R U
C6' C 0.1074(2) 0.8038(4) 0.52852(11) 0.0551(7) Uani 1 1 d . .
H6'A H 0.046058 0.790993 0.494486 0.066 Uiso 1 1 calc R U
H6'B H 0.081736 0.899599 0.553167 0.066 Uiso 1 1 calc R U
C7' C 0.2257(3) 1.0544(4) 0.48435(11) 0.0601(7) Uani 1 1 d . .
H7'A H 0.224093 1.142587 0.515199 0.090 Uiso 1 1 calc R U
H7'B H 0.157609 1.073010 0.454603 0.090 Uiso 1 1 calc R U
H7'C H 0.297838 1.069917 0.467669 0.090 Uiso 1 1 calc R U
C8' C 0.22657(17) 0.4990(4) 0.66172(9) 0.0393(6) Uani 1 1 d . .
C9' C 0.1979(2) 0.2994(4) 0.64502(10) 0.0526(7) Uani 1 1 d . .
H9'A H 0.116382 0.290291 0.626112 0.079 Uiso 1 1 calc R U
H9'B H 0.208931 0.224261 0.679641 0.079 Uiso 1 1 calc R U
H9'C H 0.250372 0.257532 0.618750 0.079 Uiso 1 1 calc R U
C10' C 0.1384(2) 0.5687(5) 0.70072(10) 0.0613(8) Uani 1 1 d . .
H10A H 0.058998 0.569298 0.678898 0.092 Uiso 1 1 calc R U
H10B H 0.160046 0.691643 0.713707 0.092 Uiso 1 1 calc R U
H10C H 0.140781 0.489072 0.734070 0.092 Uiso 1 1 calc R U
C4A C 0.54971(17) 0.5487(3) 0.72636(9) 0.0329(5) Uani 1 1 d . .
C8A C 0.66004(18) 0.5927(3) 0.70945(10) 0.0361(5) Uani 1 1 d . .
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'
Cl Cl 0.3639 0.7018 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C8A 122.92(17)
C2 N1 C9 117.96(18)
C8A N1 C9 119.11(18)
O1 C2 N1 123.72(19)
O1 C2 C3 120.60(19)
N1 C2 C3 115.66(17)
C4 O2 H2O 106(2)
C2 C3 C3' 114.76(16)
C2 C3 C4 107.67(16)
C3' C3 C4 110.77(16)
C2 C3 Cl1 105.40(13)
C3' C3 Cl1 108.06(14)
C4 C3 Cl1 110.01(14)
O3' C4 O2 112.62(16)
O3' C4 C4A 108.68(16)
O2 C4 C4A 106.35(16)
O3' C4 C3 112.59(16)
O2 C4 C3 108.26(16)
C4A C4 C3 108.07(16)
C4A C5 C6 120.1(2)
C4A C5 H5 119.9
C6 C5 H5 119.9
C7 C6 C5 119.9(2)
C7 C6 H6 120.0
C5 C6 H6 120.0
C8 C7 C6 120.4(2)
C8 C7 H7 119.8
C6 C7 H7 119.8
C7 C8 C8A 120.1(2)
C7 C8 H8 119.9
C8A C8 H8 119.9
N1 C9 H9A 109.5
N1 C9 H9AB 109.5
H9A C9 H9AB 109.5
N1 C9 H9AC 109.5
H9A C9 H9AC 109.5
H9AB C9 H9AC 109.5
O1' C1' C2' 59.12(13)
O1' C1' C7' 114.9(2)
C2' C1' C7' 118.7(2)
O1' C1' C6' 113.4(2)
C2' C1' C6' 119.8(2)
C7' C1' C6' 117.1(2)
C2' O1' C1' 60.98(13)
O1' C2' C1' 59.89(13)
O1' C2' C3' 115.02(18)
C1' C2' C3' 122.02(19)
O1' C2' H2' 115.9
C1' C2' H2' 115.9
C3' C2' H2' 115.9
C3' O2' H2'O 113(2)
O2' C3' C2' 110.97(16)
O2' C3' C4' 108.66(16)
C2' C3' C4' 109.40(16)
O2' C3' C3 107.55(16)
C2' C3' C3 112.01(17)
C4' C3' C3 108.13(16)
C4 O3' C8' 119.46(14)
C5' C4' C8' 115.10(17)
C5' C4' C3' 108.36(17)
C8' C4' C3' 115.38(17)
C5' C4' H4' 105.7
C8' C4' H4' 105.7
C3' C4' H4' 105.7
C6' C5' C4' 108.73(19)
C6' C5' H5'A 109.9
C4' C5' H5'A 109.9
C6' C5' H5'B 109.9
C4' C5' H5'B 109.9
H5'A C5' H5'B 108.3
C1' C6' C5' 113.7(2)
C1' C6' H6'A 108.8
C5' C6' H6'A 108.8
C1' C6' H6'B 108.8
C5' C6' H6'B 108.8
H6'A C6' H6'B 107.7
C1' C7' H7'A 109.5
C1' C7' H7'B 109.5
H7'A C7' H7'B 109.5
C1' C7' H7'C 109.5
H7'A C7' H7'C 109.5
H7'B C7' H7'C 109.5
O3' C8' C9' 111.32(19)
O3' C8' C10' 101.45(17)
C9' C8' C10' 109.4(2)
O3' C8' C4' 108.74(16)
C9' C8' C4' 115.36(18)
C10' C8' C4' 109.7(2)
C8' C9' H9'A 109.5
C8' C9' H9'B 109.5
H9'A C9' H9'B 109.5
C8' C9' H9'C 109.5
H9'A C9' H9'C 109.5
H9'B C9' H9'C 109.5
C8' C10' H10A 109.5
C8' C10' H10B 109.5
H10A C10' H10B 109.5
C8' C10' H10C 109.5
H10A C10' H10C 109.5
H10B C10' H10C 109.5
C5 C4A C8A 119.65(19)
C5 C4A C4 123.28(19)
C8A C4A C4 117.07(18)
C8 C8A C4A 119.7(2)
C8 C8A N1 121.3(2)
C4A C8A N1 118.99(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.354(3)
N1 C8A 1.428(3)
N1 C9 1.472(2)
O1 C2 1.224(2)
Cl1 C3 1.810(2)
C2 C3 1.536(3)
O2 C4 1.418(3)
O2 H2O 0.80(2)
C3 C3' 1.547(3)
C3 C4 1.547(3)
C4 O3' 1.396(2)
C4 C4A 1.505(3)
C5 C4A 1.380(3)
C5 C6 1.385(3)
C5 H5 0.9300
C6 C7 1.379(3)
C6 H6 0.9300
C7 C8 1.377(3)
C7 H7 0.9300
C8 C8A 1.380(3)
C8 H8 0.9300
C9 H9A 0.9600
C9 H9AB 0.9600
C9 H9AC 0.9600
C1' O1' 1.454(3)
C1' C2' 1.470(3)
C1' C7' 1.497(3)
C1' C6' 1.502(3)
O1' C2' 1.442(2)
C2' C3' 1.535(3)
C2' H2' 0.9800
O2' C3' 1.429(2)
O2' H2'O 0.79(2)
C3' C4' 1.545(3)
O3' C8' 1.466(2)
C4' C5' 1.535(3)
C4' C8' 1.540(3)
C4' H4' 0.9800
C5' C6' 1.521(3)
C5' H5'A 0.9700
C5' H5'B 0.9700
C6' H6'A 0.9700
C6' H6'B 0.9700
C7' H7'A 0.9600
C7' H7'B 0.9600
C7' H7'C 0.9600
C8' C9' 1.520(4)
C8' C10' 1.528(3)
C9' H9'A 0.9600
C9' H9'B 0.9600
C9' H9'C 0.9600
C10' H10A 0.9600
C10' H10B 0.9600
C10' H10C 0.9600
C4A C8A 1.399(3)
