#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/59/2005900.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2005900
loop_
_publ_author_name
'Banwell, M. G.'
'Hockless, D. C. R.'
'Peters, S. C.'
_publ_contact_author
;
Dr. David C. R. Hockless
Research School of Chemistry
Institute of Advanced Studies
Australian National University
Canberra, ACT 0200
Australia
;
_publ_section_title
;
 A Possible Synthetic Precursor to the Tropoloisoquinoline Alkaloid
 Pareirubrine A
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              109
_journal_page_last               111
_journal_paper_doi               10.1107/S0108270196009092
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          'C21 H23 N O8 , C H Cl3'
_chemical_formula_moiety         'C22 H24 Cl3 N O8'
_chemical_formula_structural     'C22 H24 Cl3 N O8'
_chemical_formula_sum            'C22 H24 Cl3 N O8'
_chemical_formula_weight         536.78
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 91.315(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.453(2)
_cell_length_b                   10.149(3)
_cell_length_c                   17.136(1)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    213(1)
_cell_measurement_theta_max      44.4
_cell_measurement_theta_min      30.9
_cell_volume                     2512.9(8)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1993)
;
_computing_data_reduction        TEXSAN
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92, DIRDIF94'
_diffrn_ambient_temperature      213.0(10)
_diffrn_measurement_device       AFC6R
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  2.81
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4164
_diffrn_reflns_theta_max         60.08
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.714
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type
;Semi-empirical using azimuthal (\y) scan data (North, Phillips, & Mathews,
 1968)
;
_exptl_absorpt_process_details
;Semi-empirical using azimuthal (ψ) scan data (North, Phillips, & Mathews,
 1968)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112.00
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.36
_refine_ls_extinction_coef       '2(2) x 10^-7^'
_refine_ls_extinction_method
;
Zachariasen (1967) type 2 Gaussian isotropic
;
_refine_ls_goodness_of_fit_obs   2.175
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         1700
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0615
_refine_ls_shift/esd_max         0.0860
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=4Fₒ²/[σ²(Fₒ²)+(0.013Fₒ²)²]
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0641
_reflns_number_observed          1700
_reflns_number_total             3986
_reflns_observed_criterion       I>3.00\s(I)
_cod_data_source_file            ta1095.cif
_cod_data_source_block           MGB12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '
w=4F~o~^2^/[\s^2^(F~o~^2^)+(0.013F~o~^2^)^2^]' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=4F~o~^2^/[\s^2^(F~o~^2^)+(0.013F~o~^2^)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2512.8(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2005900
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,1/2+y,1/2-z'
'   -x,   -y,   -z'
'   +x,1/2-y,1/2+z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Cl(1) 1.000 0.4937(2) 0.8584(3) 0.8365(1) 0.150(1) Uij
Cl(2) 0.777(4) 0.3901(6) 0.7770(9) 0.9685(2) 0.262(4) Uij
Cl(2') 0.223(4) 0.4672(10) 0.936(2) 0.9760(6) 0.211(5) Uij
Cl(3) 0.777(4) 0.3586(2) 0.6623(4) 0.8193(2) 0.177(2) Uij
Cl(3') 0.223(4) 0.382(1) 0.702(2) 0.941(1) 0.159(5) Uij
O(4') 1.000 0.9711(2) 1.1790(3) 0.3220(2) 0.052(1) Uij
O(5') 1.000 0.7777(3) 1.1946(3) 0.3346(2) 0.060(1) Uij
O(6') 1.000 0.6809(2) 1.0045(4) 0.4139(2) 0.053(1) Uij
O(8') 1.000 0.7682(2) 0.7986(4) 0.6721(2) 0.049(1) Uij
O(8'') 1.000 0.6512(2) 0.6455(4) 0.6453(2) 0.057(1) Uij
O(9) 1.000 0.7860(2) 0.4776(4) 0.6244(2) 0.063(1) Uij
O(10) 1.000 0.9595(2) 0.5326(3) 0.5826(2) 0.0368(10) Uij
O(10a) 1.000 0.8636(2) 0.5647(3) 0.4419(2) 0.0386(10) Uij
N(1) 1.000 1.0440(3) 0.7377(4) 0.4596(2) 0.035(1) Uij
C(01) 0.777(4) 0.3833(8) 0.796(2) 0.8663(6) 0.148(3) Uij
C(01') 0.223(4) 0.411(2) 0.855(2) 0.894(1) 0.038(7) Uij
C(2) 1.000 1.0986(3) 0.8334(5) 0.4271(3) 0.039(2) Uij
C(3) 1.000 1.0665(3) 0.9487(5) 0.3943(3) 0.040(1) Uij
C(3a) 1.000 0.9710(3) 0.9747(5) 0.3939(2) 0.035(1) Uij
C(4) 1.000 0.9219(3) 1.0832(5) 0.3598(3) 0.040(1) Uij
C(4') 1.000 0.9619(5) 1.1747(8) 0.2388(3) 0.105(3) Uij
C(5) 1.000 0.8271(4) 1.0923(5) 0.3662(3) 0.043(1) Uij
C(5') 1.000 0.7962(5) 1.3213(6) 0.3671(4) 0.099(3) Uij
C(6) 1.000 0.7745(3) 0.9932(5) 0.4045(3) 0.039(1) Uij
C(6') 1.000 0.6222(4) 1.0217(7) 0.3470(4) 0.076(2) Uij
C(6a) 1.000 0.8207(3) 0.8864(5) 0.4364(2) 0.034(1) Uij
C(6b) 1.000 0.7905(3) 0.7673(5) 0.4794(2) 0.035(1) Uij
C(6c) 1.000 0.6968(3) 0.7051(5) 0.4691(3) 0.046(2) Uij
C(7) 1.000 0.7195(3) 0.7794(5) 0.5435(3) 0.039(1) Uij
C(8) 1.000 0.7312(3) 0.7042(6) 0.6189(3) 0.045(1) Uij
C(8') 1.000 0.7839(4) 0.7520(7) 0.7505(3) 0.074(2) Uij
C(8'') 1.000 0.5731(4) 0.7327(7) 0.6478(4) 0.076(2) Uij
C(9) 1.000 0.8023(3) 0.5920(6) 0.6086(3) 0.042(1) Uij
C(10) 1.000 0.8933(3) 0.6343(5) 0.5756(3) 0.033(1) Uij
C(10a) 1.000 0.8772(3) 0.6780(5) 0.4898(2) 0.033(1) Uij
C(10b) 1.000 0.9553(3) 0.7640(5) 0.4604(2) 0.030(1) Uij
C(10c) 1.000 0.9166(3) 0.8815(5) 0.4303(2) 0.033(1) Uij
H(2) 1.000 1.1635 0.8185 0.4273 0.0471 Uij
H(3) 1.000 1.1082 1.0099 0.3722 0.0482 Uij
H(4'a) 1.000 0.8982 1.1695 0.2241 0.1265 Uij
H(4'b) 1.000 0.9879 1.2522 0.2173 0.1265 Uij
H(4'c) 1.000 0.9934 1.0996 0.2197 0.1265 Uij
H(5'a) 1.000 0.7553 1.3373 0.4087 0.1183 Uij
H(5'b) 1.000 0.7872 1.3866 0.3279 0.1183 Uij
H(5'c) 1.000 0.8583 1.3245 0.3862 0.1183 Uij
H(6'a) 1.000 0.6327 0.9527 0.3109 0.0917 Uij
H(6'b) 1.000 0.6351 1.1041 0.3233 0.0917 Uij
H(6'c) 1.000 0.5594 1.0198 0.3623 0.0917 Uij
H(6ca) 1.000 0.6535 0.7406 0.4323 0.0551 Uij
H(6cb) 1.000 0.6909 0.6119 0.4702 0.0551 Uij
H(7) 1.000 0.6911 0.8634 0.5478 0.0468 Uij
H(8'a) 1.000 0.8042 0.8230 0.7827 0.0883 Uij
H(8'b) 1.000 0.7281 0.7169 0.7699 0.0883 Uij
H(8'c) 1.000 0.8300 0.6852 0.7506 0.0883 Uij
H(8''a) 1.000 0.5235 0.6899 0.6730 0.0916 Uij
H(8''b) 1.000 0.5899 0.8101 0.6759 0.0916 Uij
H(8''c) 1.000 0.5542 0.7557 0.5961 0.0916 Uij
H(10) 1.000 0.9154 0.7080 0.6047 0.0397 Uij
H(010) 1.000 0.9307 0.4540 0.5723 0.0994 Uij
H(010a) 1.000 0.9197 0.5216 0.4358 0.0847 Uij
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol C. Tables 4.2.6.8  and 6.1.1.4)
;
H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol C. Tables 4.2.6.8  and 6.1.1.4)
;
N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol C. Tables 4.2.6.8  and 6.1.1.4)
;
O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol C. Tables 4.2.6.8  and 6.1.1.4)
;
Cl 0.364 0.702
;
International Tables for Crystallography
(1992, Vol C. Tables 4.2.6.8  and 6.1.1.4)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 1 0
0 2 0
0 0 4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(01) Cl(1) C(01') 28.4(9)
Cl(2') Cl(2') Cl(2) 156.0(10)
Cl(2') Cl(2') C(01') 155(2)
Cl(2) Cl(2') C(01') 48.0(10)
Cl(2') Cl(2) Cl(3') 142(2)
Cl(2') Cl(2) C(01) 89.0(10)
Cl(2') Cl(2) C(01') 60.8(10)
Cl(3') Cl(2) C(01) 64(2)
Cl(3') Cl(2) C(01') 91.0(10)
C(01) Cl(2) C(01') 29.0(10)
Cl(2) Cl(3') Cl(3) 133(2)
Cl(2) Cl(3') C(01) 85(2)
Cl(2) Cl(3') C(01') 58.0(10)
Cl(3) Cl(3') C(01) 48.0(10)
Cl(3) Cl(3') C(01') 76.0(10)
C(01) Cl(3') C(01') 28.4(10)
Cl(3') Cl(3) C(01) 47.0(10)
C(4) O(4') C(4') 114.3(6)
C(5) O(5') C(5') 116.2(6)
C(6) O(6') C(6') 119.2(6)
C(8) O(8') C(8') 115.3(6)
C(8'') O(8'') C(8) 114.1(7)
C(2) N(1) C(10b) 115.5(6)
Cl(1) C(01) Cl(2) 106.9(10)
Cl(1) C(01) Cl(3') 117.0(10)
Cl(1) C(01) Cl(3) 110.1(10)
Cl(1) C(01) C(01') 60(2)
Cl(2) C(01) Cl(3') 30.0(10)
Cl(2) C(01) Cl(3) 114.0(10)
Cl(2) C(01) C(01') 61(2)
Cl(3') C(01) Cl(3) 83.0(10)
Cl(3') C(01) C(01') 89(2)
Cl(3) C(01) C(01') 163(3)
Cl(1) C(01') Cl(2') 98.0(10)
Cl(1) C(01') Cl(2) 134(2)
Cl(1) C(01') Cl(3') 119(2)
Cl(1) C(01') C(01) 91(2)
Cl(2') C(01') Cl(2) 71.0(10)
Cl(2') C(01') Cl(3') 98.0(10)
Cl(2') C(01') C(01) 160(3)
Cl(2) C(01') Cl(3') 30.0(10)
Cl(2) C(01') C(01) 89(2)
Cl(3') C(01') C(01) 61(2)
N(1) C(2) C(3) 125.1(7)
C(2) C(3) C(3a) 119.0(7)
C(3) C(3a) C(4) 128.8(7)
C(3) C(3a) C(10c) 115.9(7)
C(4) C(3a) C(10c) 115.3(7)
O(4') C(4) C(3a) 118.7(7)
O(4') C(4) C(5) 121.0(7)
C(3a) C(4) C(5) 120.3(7)
O(5') C(5) C(4) 122.0(7)
O(5') C(5) C(6) 116.0(7)
C(4) C(5) C(6) 121.9(7)
O(6') C(6) C(5) 122.1(7)
O(6') C(6) C(6a) 119.3(7)
C(5) C(6) C(6a) 118.5(7)
C(6) C(6a) C(6b) 133.6(7)
C(6) C(6a) C(10c) 118.2(7)
C(6b) C(6a) C(10c) 108.2(6)
C(6a) C(6b) C(6c) 123.9(6)
C(6a) C(6b) C(7) 120.1(6)
C(6a) C(6b) C(10a) 106.6(6)
C(6c) C(6b) C(7) 59.9(4)
C(6c) C(6b) C(10a) 119.4(6)
C(7) C(6b) C(10a) 121.2(6)
C(6b) C(6c) C(7) 60.8(4)
C(6b) C(7) C(6c) 59.2(4)
C(6b) C(7) C(8) 120.8(6)
C(6c) C(7) C(8) 119.3(7)
O(8') C(8) O(8'') 112.6(6)
O(8') C(8) C(7) 104.0(6)
O(8') C(8) C(9) 109.2(6)
O(8'') C(8) C(7) 114.8(6)
O(8'') C(8) C(9) 106.5(6)
C(7) C(8) C(9) 109.7(6)
O(9) C(9) C(8) 122.9(7)
O(9) C(9) C(10) 122.1(7)
C(8) C(9) C(10) 114.9(7)
C(3a) C(10c) C(6a) 125.8(7)
C(3a) C(10c) C(10b) 121.1(7)
C(6a) C(10c) C(10b) 113.0(7)
O(10) C(10) C(9) 110.8(6)
O(10) C(10) C(10a) 112.2(5)
C(9) C(10) C(10a) 108.9(5)
O(10a) C(10a) C(6b) 107.7(5)
O(10a) C(10a) C(10) 109.4(6)
O(10a) C(10a) C(10b) 111.4(5)
C(6b) C(10a) C(10) 112.3(5)
C(6b) C(10a) C(10b) 103.3(5)
C(10) C(10a) C(10b) 112.5(5)
N(1) C(10b) C(10c) 123.3(7)
N(1) C(10b) C(10a) 128.3(6)
C(10c) C(10b) C(10a) 108.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl(1) C(01) 1.80(2)
Cl(1) C(01') 1.56(3)
Cl(2') Cl(2') 1.79(5)
Cl(2') Cl(2) 1.97(3)
Cl(2') C(01') 1.81(2)
Cl(2) Cl(3') 0.91(3)
Cl(2) C(01) 1.76(2)
Cl(2) C(01') 1.54(3)
Cl(3') Cl(3) 2.14(3)
Cl(3') C(01) 1.59(3)
Cl(3') C(01') 1.81(2)
Cl(3) C(01) 1.61(2)
O(4') C(4) 1.376(8)
O(4') C(4') 1.429(9)
O(5') C(5) 1.365(8)
O(5') C(5') 1.423(9)
O(6') C(6) 1.370(8)
O(6') C(6') 1.421(9)
O(8') C(8) 1.418(8)
O(8') C(8') 1.438(8)
O(8'') C(8'') 1.435(9)
O(8'') C(8) 1.387(8)
O(9) C(9) 1.217(8)
O(10) C(10) 1.410(7)
O(10a) C(10a) 1.424(8)
N(1) C(2) 1.377(8)
N(1) C(10b) 1.310(8)
C(01) C(01') 0.86(3)
C(2) C(3) 1.374(10)
C(3) C(3a) 1.405(9)
C(3a) C(4) 1.428(9)
C(3a) C(10c) 1.388(9)
C(4) C(5) 1.380(10)
C(5) C(6) 1.430(10)
C(6) C(6a) 1.378(9)
C(6a) C(6b) 1.487(9)
C(6a) C(10c) 1.393(9)
C(6b) C(6c) 1.500(9)
C(6b) C(7) 1.525(9)
C(6b) C(10a) 1.553(9)
C(6c) C(7) 1.511(9)
C(7) C(8) 1.507(9)
C(8) C(9) 1.550(10)
C(9) C(10) 1.506(9)
C(10c) C(10b) 1.410(9)
C(10) C(10a) 1.548(9)
C(10a) C(10b) 1.522(9)
