#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:59:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180459 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/28/7212865.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_7212865
loop_
_publ_author_name
'Braga, Dario'
'Dichiarante, Elena'
'Palladino, Giuseppe'
'Grepioni, Fabrizia'
'Chierotti, Michele R.'
'Gobetto, Roberto'
'Pellegrino, Luca'
_publ_section_title
;
 Remarkable reversal of melting point alternation by co-crystallization
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3534
_journal_paper_doi               10.1039/c0ce00253d
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C22 H28 N2 O4'
_chemical_formula_weight         384.46
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.230(5)
_cell_angle_beta                 73.739(6)
_cell_angle_gamma                71.192(6)
_cell_formula_units_Z            1
_cell_length_a                   6.9363(4)
_cell_length_b                   6.9574(4)
_cell_length_c                   12.0029(8)
_cell_measurement_temperature    293(2)
_cell_volume                     520.90(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.833
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4579
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0799P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                1038
_reflns_number_total             2332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00253d.txt
_cod_data_source_block           1.C10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        520.90(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7212865
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
O1 O 0.6712(3) 0.5845(2) 0.31070(15) 0.0697(5) Uani 1 1 d .
H100 H 0.699(4) 0.700(4) 0.263(2) 0.105 Uiso 1 1 d .
O2 O 0.4031(3) 0.6677(2) 0.22755(15) 0.0788(6) Uani 1 1 d .
C2 C 0.4540(4) 0.3674(3) 0.3714(2) 0.0553(6) Uani 1 1 d .
H2A H 0.4558 0.3721 0.4512 0.097(9) Uiso 1 1 d R
H2B H 0.5653 0.2487 0.3457 0.107(10) Uiso 1 1 d R
C4 C 0.5025(4) 0.5566(3) 0.29605(18) 0.0480(6) Uani 1 1 d .
C9 C 0.2497(4) 0.3354(3) 0.3735(2) 0.0566(7) Uani 1 1 d .
H9A H 0.1359 0.4490 0.4035 0.119(11) Uiso 1 1 d R
H9B H 0.2437 0.3334 0.2940 0.090(9) Uiso 1 1 d R
C11 C 0.2207(4) 0.1364(3) 0.4484(2) 0.0608(7) Uani 1 1 d .
H11A H 0.2451 0.1328 0.5246 0.107(10) Uiso 1 1 d R
H11B H 0.3270 0.0235 0.4129 0.106(10) Uiso 1 1 d R
C14 C 0.0102(4) 0.1027(3) 0.4663(2) 0.0611(7) Uani 1 1 d .
H14A H -0.0190 0.1162 0.3900 0.113(10) Uiso 1 1 d R
H14B H -0.0953 0.2097 0.5072 0.146(14) Uiso 1 1 d R
N1 N 0.7654(3) -0.0797(2) 0.18454(15) 0.0530(5) Uani 1 1 d .
C1 C 0.9024(3) 0.4810(3) -0.0044(2) 0.0570(6) Uani 1 1 d .
H1A H 0.9067 0.4858 -0.0864 0.103(10) Uiso 1 1 d R
H1B H 0.7852 0.5928 0.0247 0.100(9) Uiso 1 1 d R
C3 C 0.9823(4) 0.1440(3) 0.13478(19) 0.0555(6) Uani 1 1 d .
H3 H 1.0994 0.1705 0.1443 0.072(7) Uiso 1 1 d R
C5 C 0.6906(4) 0.2300(3) 0.0524(2) 0.0591(7) Uani 1 1 d .
H5 H 0.6045 0.3163 0.0040 0.074(7) Uiso 1 1 d R
C7 C 0.8605(3) 0.2819(3) 0.06246(17) 0.0458(6) Uani 1 1 d .
C13 C 0.6478(4) 0.0517(3) 0.1153(2) 0.0587(7) Uani 1 1 d .
H13 H 0.5308 0.0220 0.1083 0.071(8) Uiso 1 1 d R
C20 C 0.9298(4) -0.0333(3) 0.19289(19) 0.0576(7) Uani 1 1 d .
H20 H 1.0150 -0.1254 0.2401 0.070(7) Uiso 1 1 d 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'
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
C4 O1 H100 110.6(17) . .
C9 C2 C4 116.58(19) . .
C9 C2 H2A 107.8 . .
C4 C2 H2A 108.1 . .
C9 C2 H2B 108.4 . .
C4 C2 H2B 108.4 . .
H2A C2 H2B 107.3 . .
O2 C4 O1 123.24(19) . .
O2 C4 C2 124.6(2) . .
O1 C4 C2 112.13(19) . .
C2 C9 C11 112.08(19) . .
C2 C9 H9A 109.6 . .
C11 C9 H9A 109.2 . .
C2 C9 H9B 109.0 . .
C11 C9 H9B 109.0 . .
H9A C9 H9B 107.9 . .
C14 C11 C9 115.7(2) . .
C14 C11 H11A 108.4 . .
C9 C11 H11A 108.1 . .
C14 C11 H11B 108.6 . .
C9 C11 H11B 108.4 . .
H11A C11 H11B 107.5 . .
C11 C14 C14 114.8(3) . 2_556
C11 C14 H14A 108.5 . .
C14 C14 H14A 108.4 2_556 .
C11 C14 H14B 108.8 . .
C14 C14 H14B 108.6 2_556 .
H14A C14 H14B 107.5 . .
C20 N1 C13 117.11(18) . .
C1 C1 C7 116.1(2) 2_765 .
C1 C1 H1A 108.7 2_765 .
C7 C1 H1A 108.6 . .
C1 C1 H1B 107.6 2_765 .
C7 C1 H1B 107.9 . .
H1A C1 H1B 107.5 . .
C20 C3 C7 119.8(2) . .
C20 C3 H3 120.1 . .
C7 C3 H3 120.1 . .
C13 C5 C7 119.8(2) . .
C13 C5 H5 120.2 . .
C7 C5 H5 119.9 . .
C5 C7 C3 116.36(18) . .
C5 C7 C1 119.4(2) . .
C3 C7 C1 124.3(2) . .
N1 C13 C5 123.4(2) . .
N1 C13 H13 118.5 . .
C5 C13 H13 118.1 . .
N1 C20 C3 123.4(2) . .
N1 C20 H20 118.0 . .
C3 C20 H20 118.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.309(2) .
O1 H100 0.92(3) .
O2 C4 1.201(2) .
C2 C9 1.497(3) .
C2 C4 1.501(3) .
C2 H2A 0.9699 .
C2 H2B 0.9699 .
C9 C11 1.515(3) .
C9 H9A 0.9700 .
C9 H9B 0.9699 .
C11 C14 1.502(3) .
C11 H11A 0.9696 .
C11 H11B 0.9696 .
C14 C14 1.508(4) 2_556
C14 H14A 0.9698 .
C14 H14B 0.9697 .
N1 C20 1.315(3) .
N1 C13 1.325(3) .
C1 C1 1.497(4) 2_765
C1 C7 1.512(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C3 C20 1.382(3) .
C3 C7 1.381(3) .
C3 H3 0.9296 .
C5 C13 1.376(3) .
C5 C7 1.381(3) .
C5 H5 0.9297 .
C13 H13 0.9288 .
C20 H20 0.9298 .
