#------------------------------------------------------------------------------
#$Date: 2017-04-25 08:35:58 +0300 (Tue, 25 Apr 2017) $
#$Revision: 195747 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545849.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_1545849
loop_
_publ_author_name
'Dubey, Ritesh'
'Mir, Niyaz A.'
'Desiraju, Gautam R.'
_publ_section_title
;
 Quaternary cocrystals: combinatorial synthetic strategies based on
 long-range synthon Aufbau modules (LSAM)
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              102
_journal_page_last               107
_journal_paper_doi               10.1107/S2052252515023957
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C24 H23 N2 O2'
_chemical_formula_weight         371.44
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                109.665(8)
_cell_angle_beta                 94.353(7)
_cell_angle_gamma                90.742(7)
_cell_formula_units_Z            2
_cell_length_a                   8.971(4)
_cell_length_b                   10.078(4)
_cell_length_c                   11.666(5)
_cell_measurement_temperature    293(2)
_cell_volume                     989.5(7)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1280
_diffrn_reflns_av_unetI/netI     0.1681
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9373
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         3.063
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       Plate
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.2240
_refine_ls_R_factor_gt           0.0953
_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)+(0.1142P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.2760
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1683
_reflns_number_total             4291
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hi5641.cif
_cod_data_source_block           TS_ORC_TMP_ACR
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/IUCr/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1545849
_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.
;
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.1924(3) 0.3176(3) 0.5288(3) 0.0427(9) Uani 1 1 d . .
H1O H 0.2524 0.2566 0.5279 0.064 Uiso 1 1 calc R U
N2 N -0.6554(4) 0.1035(4) 0.8671(3) 0.0349(9) Uani 1 1 d . .
O2 O 0.0956(3) 0.2644(3) 0.9121(3) 0.0431(9) Uani 1 1 d . .
H2O H 0.1699 0.2169 0.8982 0.065 Uiso 1 1 calc R U
C4 C 0.1493(4) 0.2869(4) 0.7207(4) 0.0307(10) Uani 1 1 d . .
H4 H 0.2233 0.2210 0.7106 0.037 Uiso 1 1 calc R U
C23 C -0.5482(5) -0.1214(4) 0.7609(4) 0.0335(10) Uani 1 1 d . .
C18 C -0.6702(4) -0.0291(5) 0.7914(4) 0.0346(11) Uani 1 1 d . .
C12 C -0.3896(4) 0.0711(5) 0.8993(4) 0.0345(11) Uani 1 1 d . .
C24 C -0.4063(5) -0.0647(5) 0.8206(4) 0.0423(12) Uani 1 1 d . .
H24 H -0.3235 -0.1207 0.8059 0.051 Uiso 1 1 calc R U
C2 C 0.0083(4) 0.4502(4) 0.6483(4) 0.0346(10) Uani 1 1 d . .
H2 H -0.0121 0.4921 0.5892 0.041 Uiso 1 1 calc R U
C1 C -0.0695(4) 0.4871(4) 0.7518(4) 0.0314(10) Uani 1 1 d . .
C3 C 0.1177(4) 0.3498(4) 0.6332(4) 0.0306(10) Uani 1 1 d . .
C16 C -0.5016(5) 0.2976(5) 1.0011(4) 0.0443(12) Uani 1 1 d . .
H16 H -0.5845 0.3536 1.0138 0.053 Uiso 1 1 calc R U
C5 C 0.0688(4) 0.3232(4) 0.8248(4) 0.0310(10) Uani 1 1 d . .
C6 C -0.0402(4) 0.4236(4) 0.8391(4) 0.0351(11) Uani 1 1 d . .
H6 H -0.0938 0.4481 0.9080 0.042 Uiso 1 1 calc R U
C17 C -0.5176(4) 0.1556(5) 0.9223(4) 0.0332(10) Uani 1 1 d . .
C19 C -0.8152(5) -0.0832(5) 0.7307(4) 0.0415(12) Uani 1 1 d . .
H19 H -0.8964 -0.0253 0.7469 0.050 Uiso 1 1 calc R U
C22 C -0.5738(5) -0.2610(5) 0.6781(5) 0.0481(13) Uani 1 1 d . .
H22 H -0.4947 -0.3213 0.6595 0.058 Uiso 1 1 calc R U
C20 C -0.8360(5) -0.2154(5) 0.6515(4) 0.0456(12) Uani 1 1 d . .
H20 H -0.9308 -0.2471 0.6131 0.055 Uiso 1 1 calc R U
C21 C -0.7154(5) -0.3071(5) 0.6257(5) 0.0517(14) Uani 1 1 d . .
H21 H -0.7323 -0.3994 0.5727 0.062 Uiso 1 1 calc R U
C13 C -0.2477(5) 0.1333(6) 0.9612(5) 0.0515(14) Uani 1 1 d . .
H13 H -0.1630 0.0798 0.9487 0.062 Uiso 1 1 calc R U
C14 C -0.2360(5) 0.2701(6) 1.0380(5) 0.0544(14) Uani 1 1 d . .
H14 H -0.1435 0.3092 1.0770 0.065 Uiso 1 1 calc R U
C7 C -0.1832(5) 0.6018(5) 0.7701(4) 0.0437(12) Uani 1 1 d . .
H7A H -0.1927 0.6304 0.6994 0.066 Uiso 1 1 calc R U
H7B H -0.1501 0.6813 0.8408 0.066 Uiso 1 1 calc R U
H7C H -0.2784 0.5658 0.7818 0.066 Uiso 1 1 calc R U
C15 C -0.3648(6) 0.3532(5) 1.0585(4) 0.0520(14) Uani 1 1 d . .
H15 H -0.3559 0.4460 1.1115 0.062 Uiso 1 1 calc R U
N1 N 0.3945(3) 0.1024(4) 0.5190(3) 0.0332(9) Uani 1 1 d . .
C9 C 0.3584(4) -0.0295(5) 0.4474(4) 0.0339(11) Uani 1 1 d . .
C10 C 0.5350(4) 0.1342(4) 0.5741(4) 0.0335(11) Uani 1 1 d . .
C8 C 0.2004(4) -0.0630(5) 0.3899(5) 0.0506(14) Uani 1 1 d . .
H8A H 0.1445 0.0212 0.4133 0.076 Uiso 1 1 calc R U
H8B H 0.1546 -0.1325 0.4170 0.076 Uiso 1 1 calc R U
H8C H 0.2013 -0.0989 0.3026 0.076 Uiso 1 1 calc R U
C11 C 0.5713(5) 0.2820(5) 0.6543(4) 0.0471(13) Uani 1 1 d . .
H11A H 0.4863 0.3383 0.6525 0.071 Uiso 1 1 calc R U
H11B H 0.6548 0.3188 0.6258 0.071 Uiso 1 1 calc R U
H11C H 0.5965 0.2845 0.7365 0.071 Uiso 1 1 calc R U
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
C3 O1 H1O 109.5 . .
C18 N2 C17 119.0(4) . .
C5 O2 H2O 109.5 . .
C3 C4 C5 119.5(4) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C24 C23 C22 124.0(4) . .
C24 C23 C18 115.8(4) . .
C22 C23 C18 120.2(4) . .
N2 C18 C23 123.9(4) . .
N2 C18 C19 119.0(4) . .
C23 C18 C19 117.0(4) . .
C24 C12 C17 119.1(4) . .
C24 C12 C13 122.8(4) . .
C17 C12 C13 118.0(4) . .
C12 C24 C23 120.9(4) . .
C12 C24 H24 119.6 . .
C23 C24 H24 119.6 . .
C1 C2 C3 119.5(4) . .
C1 C2 H2 120.2 . .
C3 C2 H2 120.2 . .
C2 C1 C6 120.2(4) . .
C2 C1 C7 119.0(4) . .
C6 C1 C7 120.7(4) . .
O1 C3 C4 122.1(4) . .
O1 C3 C2 117.2(4) . .
C4 C3 C2 120.7(4) . .
C15 C16 C17 120.4(5) . .
C15 C16 H16 119.8 . .
C17 C16 H16 119.8 . .
O2 C5 C6 119.1(4) . .
O2 C5 C4 121.5(4) . .
C6 C5 C4 119.4(4) . .
C1 C6 C5 120.6(4) . .
C1 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
N2 C17 C16 118.9(4) . .
N2 C17 C12 121.2(4) . .
C16 C17 C12 119.9(4) . .
C20 C19 C18 121.5(4) . .
C20 C19 H19 119.2 . .
C18 C19 H19 119.2 . .
C21 C22 C23 119.9(5) . .
C21 C22 H22 120.1 . .
C23 C22 H22 120.1 . .
C19 C20 C21 120.8(4) . .
C19 C20 H20 119.6 . .
C21 C20 H20 119.6 . .
C22 C21 C20 120.5(5) . .
C22 C21 H21 119.7 . .
C20 C21 H21 119.7 . .
C14 C13 C12 120.8(5) . .
C14 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C13 C14 C15 120.3(5) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C1 C7 H7A 109.5 . .
C1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C16 C15 C14 120.6(5) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C9 N1 C10 119.1(4) . .
N1 C9 C10 120.9(4) . 2_656
N1 C9 C8 118.0(4) . .
C10 C9 C8 121.1(4) 2_656 .
N1 C10 C9 120.0(4) . 2_656
N1 C10 C11 117.7(4) . .
C9 C10 C11 122.2(4) 2_656 .
C9 C8 H8A 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C9 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.379(5) .
O1 H1O 0.8200 .
N2 C18 1.329(5) .
N2 C17 1.362(5) .
O2 C5 1.349(5) .
O2 H2O 0.8200 .
C4 C3 1.386(6) .
C4 C5 1.404(5) .
C4 H4 0.9300 .
C23 C24 1.418(6) .
C23 C22 1.418(6) .
C23 C18 1.432(6) .
C18 C19 1.440(6) .
C12 C24 1.366(6) .
C12 C17 1.426(6) .
C12 C13 1.438(6) .
C24 H24 0.9300 .
C2 C1 1.384(6) .
C2 C3 1.397(6) .
C2 H2 0.9300 .
C1 C6 1.386(6) .
C1 C7 1.523(5) .
C16 C15 1.369(6) .
C16 C17 1.415(6) .
C16 H16 0.9300 .
C5 C6 1.394(5) .
C6 H6 0.9300 .
C19 C20 1.343(6) .
C19 H19 0.9300 .
C22 C21 1.371(6) .
C22 H22 0.9300 .
C20 C21 1.415(6) .
C20 H20 0.9300 .
C21 H21 0.9300 .
C13 C14 1.366(7) .
C13 H13 0.9300 .
C14 C15 1.422(7) .
C14 H14 0.9300 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C15 H15 0.9300 .
N1 C9 1.331(5) .
N1 C10 1.353(5) .
C9 C10 1.405(6) 2_656
C9 C8 1.505(6) .
C10 C9 1.405(6) 2_656
C10 C11 1.485(6) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 N2 0.93 2.67 3.340(5) 129.9 1_655
