#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/92/1519253.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_1519253
loop_
_publ_author_name
'Jones, Ray'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C21H24Cl2N4O4
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              773
_journal_year                    2000
_chemical_formula_sum            'C21 H24 Cl2 N4 O4'
_chemical_formula_weight         467.34
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.36(3)
_cell_angle_beta                 101.24(3)
_cell_angle_gamma                93.97(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5051(13)
_cell_length_b                   10.758(2)
_cell_length_c                   16.079(3)
_cell_measurement_reflns_used    9455
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.34
_cell_measurement_theta_min      2.91
_cell_volume                     1079.3(4)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_collection
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'CAMERON (Watkin, Pearce 1995)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald Sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20953
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.8769
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SORTAV (R. H. Blessing, 1995, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0618P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                3418
_reflns_number_total             4955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-773.cif
_cod_data_source_block           s92
_cod_depositor_comments
;
Citation :
Jones, Ray and Coles, Simon J. and Hursthouse, Michael B. (2000) 
University of Southampton, Crystal Structure Report Archive. 

More at:
http://ecrystals.chem.soton.ac.uk/773/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30440(8) 0.51320(5) 0.19550(3) 0.04251(17) Uani 1 1 d . . .
Cl2 Cl -0.08978(8) 0.61425(5) 0.21983(4) 0.04547(18) Uani 1 1 d . . .
O1 O 0.88159(19) 0.27677(12) 0.32131(8) 0.0302(3) Uani 1 1 d . . .
O2 O 0.35705(17) 0.08752(12) 0.41881(8) 0.0293(3) Uani 1 1 d . . .
O3 O 0.38103(18) -0.39405(12) 0.42034(8) 0.0314(3) Uani 1 1 d . . .
O4 O 0.99900(17) -0.17137(12) 0.42186(8) 0.0271(3) Uani 1 1 d . . .
N1 N 0.7568(2) 0.01996(15) 0.19686(9) 0.0250(3) Uani 1 1 d . . .
N2 N 0.6727(2) -0.13425(14) 0.27327(9) 0.0212(3) Uani 1 1 d . . .
N3 N 0.5844(2) 0.19674(14) 0.35897(9) 0.0233(3) Uani 1 1 d . . .
N4 N 0.7145(2) -0.30847(14) 0.42209(9) 0.0217(3) Uani 1 1 d . . .
C1 C 0.6757(3) 0.2209(2) 0.10452(12) 0.0371(5) Uani 1 1 d . . .
H1 H 0.5861 0.2003 0.1413 0.044 Uiso 1 1 calc R . .
C2 C 0.6267(4) 0.3120(2) 0.05583(13) 0.0464(6) Uani 1 1 d . . .
H2 H 0.5039 0.3539 0.0593 0.056 Uiso 1 1 calc R . .
C3 C 0.7546(5) 0.3426(2) 0.00228(14) 0.0553(7) Uani 1 1 d . . .
H3 H 0.7214 0.4063 -0.0306 0.066 Uiso 1 1 calc R . .
C4 C 0.9293(5) 0.2812(3) -0.00351(14) 0.0586(7) Uani 1 1 d . . .
H4 H 1.0169 0.3019 -0.0410 0.070 Uiso 1 1 calc R . .
C5 C 0.9801(4) 0.1891(2) 0.04477(13) 0.0438(6) Uani 1 1 d . . .
H5 H 1.1016 0.1464 0.0398 0.053 Uiso 1 1 calc R . .
C6 C 0.8549(3) 0.15873(19) 0.10030(12) 0.0325(5) Uani 1 1 d . . .
C7 C 0.9231(3) 0.0665(2) 0.15839(12) 0.0309(4) Uani 1 1 d . . .
H7A H 0.9736 -0.0068 0.1243 0.037 Uiso 1 1 calc R . .
H7B H 1.0429 0.1090 0.2052 0.037 Uiso 1 1 calc R . .
C8 C 0.5995(3) -0.07803(19) 0.14014(12) 0.0321(5) Uani 1 1 d . . .
H8A H 0.6663 -0.1462 0.1086 0.039 Uiso 1 1 calc R . .
H8B H 0.5009 -0.0419 0.0981 0.039 Uiso 1 1 calc R . .
C9 C 0.4897(3) -0.12602(19) 0.20479(11) 0.0286(4) Uani 1 1 d . . .
H9A H 0.3952 -0.0653 0.2262 0.034 Uiso 1 1 calc R . .
H9B H 0.4081 -0.2101 0.1800 0.034 Uiso 1 1 calc R . .
C10 C 0.8351(2) -0.03212(17) 0.27382(11) 0.0218(4) Uani 1 1 d . . .
H10 H 0.9721 -0.0673 0.2701 0.026 Uiso 1 1 calc R . .
C11 C 0.8596(2) 0.06758(16) 0.36003(10) 0.0198(4) Uani 1 1 d . . .
H11 H 1.0064 0.0787 0.3955 0.024 Uiso 1 1 calc R . .
C12 C 0.7869(3) 0.19166(17) 0.34316(11) 0.0222(4) Uani 1 1 d . . .
C13 C 0.4569(3) 0.29989(19) 0.34472(13) 0.0333(5) Uani 1 1 d . . .
H13A H 0.3083 0.2657 0.3246 0.050 Uiso 1 1 calc R . .
H13B H 0.5024 0.3416 0.3010 0.050 Uiso 1 1 calc R . .
H13C H 0.4741 0.3618 0.3990 0.050 Uiso 1 1 calc R . .
C14 C 0.5230(2) 0.09855(17) 0.39561(10) 0.0212(4) Uani 1 1 d . . .
C15 C 0.6993(2) 0.01433(16) 0.40656(11) 0.0191(4) Uani 1 1 d . . .
H15 H 0.7635 0.0217 0.4693 0.023 Uiso 1 1 calc R . .
C16 C 0.6428(2) -0.12670(16) 0.36180(10) 0.0191(4) Uani 1 1 d . . .
C17 C 0.4369(2) -0.19653(17) 0.36993(11) 0.0224(4) Uani 1 1 d . . .
H17A H 0.3665 -0.1413 0.4094 0.027 Uiso 1 1 calc R . .
H17B H 0.3398 -0.2219 0.3127 0.027 Uiso 1 1 calc R . .
C18 C 0.4965(2) -0.31140(17) 0.40561(11) 0.0224(4) Uani 1 1 d . . .
C19 C 0.8312(3) -0.40343(19) 0.45858(13) 0.0325(5) Uani 1 1 d . . .
H19A H 0.8340 -0.4762 0.4125 0.049 Uiso 1 1 calc R . .
H19B H 0.7625 -0.4318 0.5020 0.049 Uiso 1 1 calc R . .
H19C H 0.9758 -0.3663 0.4858 0.049 Uiso 1 1 calc R . .
C20 C 0.8112(2) -0.20131(17) 0.40519(10) 0.0202(4) Uani 1 1 d . . .
C21 C 0.0657(3) 0.4886(2) 0.23010(14) 0.0382(5) Uani 1 1 d . . .
H21A H -0.0148 0.4084 0.1953 0.046 Uiso 1 1 calc R . .
H21B H 0.0977 0.4796 0.2914 0.046 Uiso 1 1 calc R . .
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'
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
C7 N1 C8 115.84(14) . .
C7 N1 C10 113.40(14) . .
C8 N1 C10 105.78(14) . .
C16 N2 C10 108.14(13) . .
C16 N2 C9 118.78(12) . .
C10 N2 C9 107.19(13) . .
C14 N3 C12 112.73(14) . .
C14 N3 C13 123.10(14) . .
C12 N3 C13 124.01(15) . .
C20 N4 C18 112.61(15) . .
C20 N4 C19 122.79(14) . .
C18 N4 C19 124.49(15) . .
C2 C1 C6 120.6(2) . .
C3 C2 C1 120.3(2) . .
C4 C3 C2 119.8(2) . .
C3 C4 C5 120.6(2) . .
C4 C5 C6 120.4(2) . .
C5 C6 C1 118.3(2) . .
C5 C6 C7 119.64(19) . .
C1 C6 C7 121.93(17) . .
N1 C7 C6 113.48(15) . .
N1 C8 C9 101.25(14) . .
N2 C9 C8 100.56(13) . .
N1 C10 N2 105.18(13) . .
N1 C10 C11 112.78(14) . .
N2 C10 C11 107.91(13) . .
C12 C11 C15 104.91(13) . .
C12 C11 C10 111.40(14) . .
C15 C11 C10 104.41(13) . .
O1 C12 N3 123.47(17) . .
O1 C12 C11 128.49(15) . .
N3 C12 C11 108.02(14) . .
O2 C14 N3 124.01(16) . .
O2 C14 C15 126.98(16) . .
N3 C14 C15 108.91(13) . .
C14 C15 C11 103.87(14) . .
C14 C15 C16 116.11(13) . .
C11 C15 C16 105.37(13) . .
N2 C16 C17 115.12(13) . .
N2 C16 C20 105.93(13) . .
C17 C16 C20 102.87(13) . .
N2 C16 C15 105.97(14) . .
C17 C16 C15 118.82(14) . .
C20 C16 C15 107.13(13) . .
C18 C17 C16 106.12(13) . .
O3 C18 N4 123.52(17) . .
O3 C18 C17 127.92(15) . .
N4 C18 C17 108.54(14) . .
O4 C20 N4 124.98(16) . .
O4 C20 C16 125.87(16) . .
N4 C20 C16 109.15(13) . .
Cl2 C21 Cl1 112.02(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C21 1.767(2) .
Cl2 C21 1.756(2) .
O1 C12 1.210(2) .
O2 C14 1.2137(19) .
O3 C18 1.210(2) .
O4 C20 1.2062(19) .
N1 C7 1.450(2) .
N1 C8 1.460(2) .
N1 C10 1.466(2) .
N2 C16 1.463(2) .
N2 C10 1.468(2) .
N2 C9 1.475(2) .
N3 C14 1.371(2) .
N3 C12 1.392(2) .
N3 C13 1.455(2) .
N4 C20 1.370(2) .
N4 C18 1.388(2) .
N4 C19 1.454(2) .
C1 C2 1.377(3) .
C1 C6 1.391(3) .
C2 C3 1.373(3) .
C3 C4 1.364(4) .
C4 C5 1.384(3) .
C5 C6 1.385(3) .
C6 C7 1.512(3) .
C8 C9 1.513(3) .
C10 C11 1.566(2) .
C11 C12 1.499(2) .
C11 C15 1.533(2) .
C14 C15 1.513(2) .
C15 C16 1.543(2) .
C16 C17 1.530(2) .
C16 C20 1.535(2) .
C17 C18 1.497(3) .
