#------------------------------------------------------------------------------
#$Date: 2017-04-25 08:35:58 +0300 (Tue, 25 Apr 2017) $
#$Revision: 195747 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545843.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_1545843
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            'C29 H31 N3 O2'
_chemical_formula_weight         453.57
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                74.162(5)
_cell_angle_beta                 77.589(5)
_cell_angle_gamma                89.115(6)
_cell_formula_units_Z            2
_cell_length_a                   8.9943(15)
_cell_length_b                   9.5169(16)
_cell_length_c                   14.927(3)
_cell_measurement_temperature    150(2)
_cell_volume                     1199.2(4)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0365
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12751
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.997
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       Plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0723P)²+0.2791P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1537
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3925
_reflns_number_total             5486
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hi5641.cif
_cod_data_source_block           QS_ORC_TMP_PHE_HMB
_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               1545843
_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   0.984
_shelx_estimated_absorpt_t_max   0.988
_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
C30 C 0.2473(3) 0.1475(3) 0.04114(17) 0.0523(6) Uani 1 1 d . .
H30A H 0.2058 0.2181 0.0759 0.078 Uiso 1 1 calc R U
H30B H 0.3156 0.1990 -0.0193 0.078 Uiso 1 1 calc R U
H30C H 0.3042 0.0759 0.0798 0.078 Uiso 1 1 calc R U
H2O H 0.751(3) 0.283(3) 0.4660(16) 0.051(6) Uiso 1 1 d . .
H1O H 0.749(3) 0.584(3) 0.1716(16) 0.054(6) Uiso 1 1 d . .
N2 N 0.89990(15) 0.67758(15) 0.20159(10) 0.0260(3) Uani 1 1 d . .
N3 N 1.13781(16) 0.79807(16) 0.25887(11) 0.0316(3) Uani 1 1 d . .
C13 C 0.87034(19) 0.74366(17) 0.27193(12) 0.0260(4) Uani 1 1 d . .
C5 C 0.68503(17) 0.37273(17) 0.31334(11) 0.0229(3) Uani 1 1 d . .
H5 H 0.7593 0.4369 0.3199 0.028 Uiso 1 1 calc R U
O2 O 0.68945(15) 0.20761(14) 0.46667(8) 0.0320(3) Uani 1 1 d . .
O1 O 0.66969(14) 0.53096(14) 0.15973(8) 0.0316(3) Uani 1 1 d . .
C23 C 1.0838(2) 0.59719(19) 0.08716(13) 0.0311(4) Uani 1 1 d . .
H23 H 1.0047 0.5577 0.0669 0.037 Uiso 1 1 calc R U
C24 C 1.04651(18) 0.66972(17) 0.15972(12) 0.0258(4) Uani 1 1 d . .
N1 N 0.89673(15) 0.41726(15) 0.47763(10) 0.0261(3) Uani 1 1 d . .
C18 C 0.99089(19) 0.80540(18) 0.30018(12) 0.0280(4) Uani 1 1 d . .
C14 C 0.7168(2) 0.74971(19) 0.32091(13) 0.0319(4) Uani 1 1 d . .
H14 H 0.6361 0.7066 0.3040 0.038 Uiso 1 1 calc R U
C19 C 1.16663(19) 0.73017(18) 0.18940(12) 0.0280(4) Uani 1 1 d . .
C7 C 0.52713(18) 0.15131(18) 0.37499(12) 0.0253(4) Uani 1 1 d . .
H7 H 0.4930 0.0644 0.4246 0.030 Uiso 1 1 calc R U
C20 C 1.3201(2) 0.7145(2) 0.14482(14) 0.0360(4) Uani 1 1 d . .
H20 H 1.4013 0.7544 0.1631 0.043 Uiso 1 1 calc R U
C17 C 0.9525(2) 0.8764(2) 0.37444(13) 0.0355(4) Uani 1 1 d . .
H17 H 1.0307 0.9198 0.3933 0.043 Uiso 1 1 calc R U
C6 C 0.63539(18) 0.24531(18) 0.38466(11) 0.0233(3) Uani 1 1 d . .
C2 C 0.51718(18) 0.31131(18) 0.22194(11) 0.0252(4) Uani 1 1 d . .
H2 H 0.4769 0.3344 0.1660 0.030 Uiso 1 1 calc R U
C11 C 1.04460(18) 0.42497(18) 0.43466(12) 0.0254(4) Uani 1 1 d . .
C4 C 0.62503(18) 0.40597(18) 0.23193(11) 0.0240(4) Uani 1 1 d . .
C21 C 1.3511(2) 0.6424(2) 0.07591(14) 0.0387(5) Uani 1 1 d . .
H21 H 1.4542 0.6315 0.0474 0.046 Uiso 1 1 calc R U
C15 C 0.6860(2) 0.8167(2) 0.39133(14) 0.0371(4) Uani 1 1 d . .
H15 H 0.5834 0.8205 0.4236 0.045 Uiso 1 1 calc R U
C10 C 0.85016(18) 0.49176(18) 0.54252(12) 0.0258(4) Uani 1 1 d . .
C12 C 1.0912(2) 0.3401(2) 0.36269(14) 0.0365(4) Uani 1 1 d . .
H12A H 1.0023 0.2845 0.3598 0.055 Uiso 1 1 calc R U
H12B H 1.1695 0.2725 0.3815 0.055 Uiso 1 1 calc R U
H12C H 1.1322 0.4078 0.2998 0.055 Uiso 1 1 calc R U
C9 C 0.68336(19) 0.4796(2) 0.58861(14) 0.0363(4) Uani 1 1 d . .
H9A H 0.6276 0.4298 0.5556 0.054 Uiso 1 1 calc R U
H9B H 0.6452 0.5777 0.5845 0.054 Uiso 1 1 calc R U
H9C H 0.6684 0.4235 0.6558 0.054 Uiso 1 1 calc R U
C1 C 0.46840(18) 0.18330(18) 0.29350(12) 0.0250(4) Uani 1 1 d . .
C16 C 0.8054(2) 0.8817(2) 0.41776(14) 0.0394(5) Uani 1 1 d . .
H16 H 0.7810 0.9297 0.4668 0.047 Uiso 1 1 calc R U
C22 C 1.2326(2) 0.5836(2) 0.04613(13) 0.0357(4) Uani 1 1 d . .
H22 H 1.2565 0.5346 -0.0024 0.043 Uiso 1 1 calc R U
C8 C 0.3555(2) 0.0767(2) 0.28332(14) 0.0339(4) Uani 1 1 d . .
H8A H 0.4059 0.0243 0.2378 0.051 Uiso 1 1 calc R U
H8B H 0.2710 0.1298 0.2600 0.051 Uiso 1 1 calc R U
H8C H 0.3162 0.0065 0.3455 0.051 Uiso 1 1 calc R U
C27 C 0.1184(2) 0.06971(19) 0.02108(13) 0.0326(4) Uani 1 1 d . .
C26 C -0.0317(2) 0.07488(19) 0.07073(12) 0.0317(4) Uani 1 1 d . .
C28 C 0.1496(2) -0.0069(2) -0.04833(12) 0.0322(4) Uani 1 1 d . .
C29 C 0.3139(2) -0.0126(3) -0.10032(16) 0.0524(6) Uani 1 1 d . .
H29A H 0.3241 -0.0980 -0.1256 0.079 Uiso 1 1 calc R U
H29B H 0.3813 -0.0202 -0.0558 0.079 Uiso 1 1 calc R U
H29C H 0.3420 0.0765 -0.1531 0.079 Uiso 1 1 calc R U
C25 C -0.0669(3) 0.1548(2) 0.14746(15) 0.0519(6) Uani 1 1 d . .
H25A H 0.0201 0.1510 0.1777 0.078 Uiso 1 1 calc R U
H25B H -0.1573 0.1081 0.1956 0.078 Uiso 1 1 calc R U
H25C H -0.0863 0.2570 0.1186 0.078 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
C27 C30 H30A 109.5 . .
C27 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C27 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C24 N2 C13 117.62(14) . .
C18 N3 C19 116.80(14) . .
N2 C13 C14 119.61(15) . .
N2 C13 C18 121.10(15) . .
C14 C13 C18 119.27(16) . .
C6 C5 C4 119.31(14) . .
C6 C5 H5 120.3 . .
C4 C5 H5 120.3 . .
C6 O2 H2O 108.2(14) . .
C4 O1 H1O 111.2(14) . .
C22 C23 C24 120.58(16) . .
C22 C23 H23 119.7 . .
C24 C23 H23 119.7 . .
N2 C24 C23 119.76(15) . .
N2 C24 C19 120.87(15) . .
C23 C24 C19 119.34(15) . .
C11 N1 C10 119.32(14) . .
N3 C18 C17 119.57(16) . .
N3 C18 C13 121.77(15) . .
C17 C18 C13 118.66(16) . .
C15 C14 C13 119.99(17) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
N3 C19 C20 119.61(16) . .
N3 C19 C24 121.83(15) . .
C20 C19 C24 118.54(16) . .
C1 C7 C6 120.50(15) . .
C1 C7 H7 119.8 . .
C6 C7 H7 119.8 . .
C21 C20 C19 120.24(17) . .
C21 C20 H20 119.9 . .
C19 C20 H20 119.9 . .
C16 C17 C18 120.03(17) . .
C16 C17 H17 120.0 . .
C18 C17 H17 120.0 . .
O2 C6 C5 121.86(14) . .
O2 C6 C7 117.80(15) . .
C5 C6 C7 120.33(15) . .
C1 C2 C4 120.05(15) . .
C1 C2 H2 120.0 . .
C4 C2 H2 120.0 . .
N1 C11 C10 120.54(15) . 2_766
N1 C11 C12 117.41(15) . .
C10 C11 C12 122.04(15) 2_766 .
O1 C4 C5 121.53(14) . .
O1 C4 C2 118.10(14) . .
C5 C4 C2 120.38(15) . .
C20 C21 C22 121.23(17) . .
C20 C21 H21 119.4 . .
C22 C21 H21 119.4 . .
C14 C15 C16 120.81(17) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
N1 C10 C11 120.14(15) . 2_766
N1 C10 C9 117.28(15) . .
C11 C10 C9 122.57(15) 2_766 .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C9 H9A 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C10 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C1 C2 119.42(15) . .
C7 C1 C8 119.35(16) . .
C2 C1 C8 121.21(15) . .
C17 C16 C15 121.19(17) . .
C17 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C23 C22 C21 120.05(17) . .
C23 C22 H22 120.0 . .
C21 C22 H22 120.0 . .
C1 C8 H8A 109.5 . .
C1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C26 C27 C28 120.05(17) . .
C26 C27 C30 120.40(18) . .
C28 C27 C30 119.55(18) . .
C28 C26 C27 119.32(17) 2 .
C28 C26 C25 120.01(18) 2 .
C27 C26 C25 120.66(18) . .
C26 C28 C27 120.60(16) 2 .
C26 C28 C29 120.35(18) 2 .
C27 C28 C29 119.04(18) . .
C28 C29 H29A 109.5 . .
C28 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C28 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C26 C25 H25A 109.5 . .
C26 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C26 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C30 C27 1.509(3) .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
N2 C24 1.343(2) .
N2 C13 1.343(2) .
N3 C18 1.342(2) .
N3 C19 1.343(2) .
C13 C14 1.425(2) .
C13 C18 1.432(2) .
C5 C6 1.382(2) .
C5 C4 1.391(2) .
C5 H5 0.9500 .
O2 C6 1.3690(19) .
O2 H2O 0.91(2) .
O1 C4 1.366(2) .
O1 H1O 0.95(2) .
C23 C22 1.367(3) .
C23 C24 1.417(2) .
C23 H23 0.9500 .
C24 C19 1.435(2) .
N1 C11 1.340(2) .
N1 C10 1.344(2) .
C18 C17 1.429(2) .
C14 C15 1.350(3) .
C14 H14 0.9500 .
C19 C20 1.422(2) .
C7 C1 1.386(2) .
C7 C6 1.388(2) .
C7 H7 0.9500 .
C20 C21 1.365(3) .
C20 H20 0.9500 .
C17 C16 1.349(3) .
C17 H17 0.9500 .
C2 C1 1.386(2) .
C2 C4 1.392(2) .
C2 H2 0.9500 .
C11 C10 1.396(2) 2_766
C11 C12 1.501(2) .
C21 C22 1.416(3) .
C21 H21 0.9500 .
C15 C16 1.424(3) .
C15 H15 0.9500 .
C10 C11 1.396(2) 2_766
C10 C9 1.502(2) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C1 C8 1.505(2) .
C16 H16 0.9500 .
C22 H22 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C27 C26 1.401(3) .
C27 C28 1.401(3) .
C26 C28 1.395(3) 2
C26 C25 1.518(3) .
C28 C26 1.395(3) 2
C28 C29 1.522(3) .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
