#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/12/7111267.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7111267
loop_
_publ_author_name
'Walsh, R. D. Bailey'
'Bradner, M. W.'
'Fleischman, S.'
'Morales, L. A.'
'Moulton, B.'
'Rodríguez-Hornedo, N.'
'Zaworotko, M. J.'
_publ_section_title
;
 Crystal engineering of the composition of pharmaceutical phases
;
_journal_issue                   2
_journal_name_full               'Chemical Communications'
_journal_page_first              186
_journal_paper_doi               10.1039/b208574g
_journal_year                    2003
_chemical_formula_sum            'C36 H44 N2 O4'
_chemical_formula_weight         568.73
_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                93.674(11)
_cell_angle_beta                 90.880(10)
_cell_angle_gamma                104.045(7)
_cell_formula_units_Z            2
_cell_length_a                   5.759(3)
_cell_length_b                   11.683(6)
_cell_length_c                   24.705(11)
_cell_measurement_temperature    473(2)
_cell_volume                     1608.4(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      473(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0826
_diffrn_reflns_av_sigmaI/netI    0.1182
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5208
_diffrn_reflns_theta_full        20.85
_diffrn_reflns_theta_max         20.85
_diffrn_reflns_theta_min         0.83
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.302
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             612
_exptl_crystal_size_max          .05
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          1.0
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.1775
_refine_ls_R_factor_gt           0.0964
_refine_ls_shift/su_max          8.885
_refine_ls_shift/su_mean         0.118
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1643P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2510
_refine_ls_wR_factor_ref         0.2987
_reflns_number_gt                1369
_reflns_number_total             3362
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b208574gsup1.cif
_cod_data_source_block           sf0219
_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        1608.3(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7111267
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
N1 N 0.3818(11) 0.7253(5) 0.0909(3) 0.0496(18) Uani 1 1 d .
C1 C 0.5521(15) 0.6706(7) 0.1015(3) 0.059(2) Uani 1 1 d .
H1 H 0.6414 0.6928 0.1338 0.071 Uiso 1 1 calc R
C2 C 0.6051(13) 0.5816(7) 0.0671(3) 0.051(2) Uani 1 1 d .
H2 H 0.7277 0.5465 0.0763 0.061 Uiso 1 1 calc R
C3 C 0.4726(13) 0.5464(6) 0.0194(3) 0.042(2) Uani 1 1 d .
C4 C 0.2928(13) 0.6035(7) 0.0087(3) 0.047(2) Uani 1 1 d .
H4 H 0.2008 0.5832 -0.0234 0.056 Uiso 1 1 calc R
C5 C 0.2498(13) 0.6906(7) 0.0455(3) 0.048(2) Uani 1 1 d .
H5 H 0.1250 0.7255 0.0381 0.057 Uiso 1 1 calc R
N11 N 0.3949(12) 0.2362(6) 0.0870(3) 0.0524(19) Uani 1 1 d .
C11 C 0.5631(15) 0.1805(8) 0.0986(3) 0.060(2) Uani 1 1 d .
H11 H 0.6553 0.2049 0.1304 0.072 Uiso 1 1 calc R
C12 C 0.6096(14) 0.0871(7) 0.0655(3) 0.056(2) Uani 1 1 d .
H12 H 0.7306 0.0517 0.0754 0.067 Uiso 1 1 calc R
C13 C 0.4764(13) 0.0481(6) 0.0186(3) 0.040(2) Uani 1 1 d .
C14 C 0.2960(13) 0.1054(7) 0.0060(3) 0.050(2) Uani 1 1 d .
H14 H 0.2022 0.0832 -0.0256 0.060 Uiso 1 1 calc R
C15 C 0.2604(14) 0.1964(7) 0.0420(4) 0.054(2) Uani 1 1 d .
H15 H 0.1359 0.2313 0.0342 0.065 Uiso 1 1 calc R
O21 O 1.3327(10) 0.3971(4) 0.1620(2) 0.0574(16) Uani 1 1 d .
O22 O 1.0119(10) 0.4185(5) 0.1172(2) 0.0679(18) Uani 1 1 d .
C21 C 1.1418(16) 0.4384(7) 0.1571(4) 0.057(2) Uani 1 1 d .
C22 C 1.1020(19) 0.5068(8) 0.2094(4) 0.077(3) Uani 1 1 d .
H22 H 1.261(14) 0.553(8) 0.222(4) 0.092 Uiso 1 1 calc .
C23 C 0.961(2) 0.5921(9) 0.2023(4) 0.114(4) Uani 1 1 d .
H23A H 0.7997 0.5513 0.1913 0.137 Uiso 1 1 calc R
H23B H 1.0294 0.6438 0.1750 0.137 Uiso 1 1 calc R
H23C H 0.9592 0.6377 0.2360 0.137 Uiso 1 1 calc R
C24 C 1.0227(18) 0.4204(8) 0.2520(3) 0.061(3) Uani 1 1 d .
C25 C 0.7874(18) 0.3537(8) 0.2538(3) 0.070(3) Uani 1 1 d .
H25 H 0.6727 0.3649 0.2291 0.085 Uiso 1 1 calc R
C26 C 0.7221(16) 0.2705(8) 0.2921(4) 0.072(3) Uani 1 1 d .
H26 H 0.5625 0.2293 0.2931 0.086 Uiso 1 1 calc R
C27 C 0.8837(18) 0.2471(8) 0.3283(3) 0.063(3) Uani 1 1 d .
C28 C 1.1166(17) 0.3153(8) 0.3263(3) 0.073(3) Uani 1 1 d .
H28 H 1.2316 0.3051 0.3512 0.088 Uiso 1 1 calc R
C29 C 1.1813(15) 0.3975(8) 0.2886(4) 0.069(3) Uani 1 1 d .
H29 H 1.3407 0.4393 0.2880 0.083 Uiso 1 1 calc R
C30 C 0.8115(17) 0.1538(8) 0.3686(3) 0.082(3) Uani 1 1 d .
H30A H 0.6644 0.0992 0.3549 0.098 Uiso 1 1 calc R
H30B H 0.9338 0.1095 0.3694 0.098 Uiso 1 1 calc R
O41 O 1.3164(10) 0.8858(5) 0.1646(2) 0.0657(17) Uani 1 1 d .
O42 O 1.0087(10) 0.9084(5) 0.1153(2) 0.0674(18) Uani 1 1 d .
C41 C 1.1358(17) 0.9315(7) 0.1554(4) 0.058(3) Uani 1 1 d .
C42 C 1.1076(19) 1.0136(8) 0.2032(4) 0.081(3) Uani 1 1 d .
H42 H 1.271(15) 1.058(8) 0.214(4) 0.097 Uiso 1 1 calc .
C43 C 0.982(2) 1.1018(8) 0.1907(4) 0.117(4) Uani 1 1 d .
H43A H 1.0723 1.1540 0.1659 0.140 Uiso 1 1 calc R
H43B H 0.9610 1.1465 0.2235 0.140 Uiso 1 1 calc R
H43C H 0.8276 1.0637 0.1744 0.140 Uiso 1 1 calc R
C44 C 1.0138(19) 0.9451(8) 0.2523(4) 0.066(3) Uani 1 1 d .
C45 C 1.1589(16) 0.9411(8) 0.2956(4) 0.069(3) Uani 1 1 d .
H45 H 1.3204 0.9791 0.2944 0.083 Uiso 1 1 calc R
C46 C 1.0792(18) 0.8838(8) 0.3407(4) 0.079(3) Uani 1 1 d .
H46 H 1.1856 0.8855 0.3696 0.095 Uiso 1 1 calc R
C47 C 0.8420(18) 0.8234(8) 0.3439(4) 0.071(3) Uani 1 1 d .
C48 C 0.6872(17) 0.8217(8) 0.2992(4) 0.082(3) Uani 1 1 d .
H48 H 0.5275 0.7803 0.2994 0.099 Uiso 1 1 calc R
C49 C 0.7763(19) 0.8825(8) 0.2549(4) 0.075(3) Uani 1 1 d .
H49 H 0.6728 0.8817 0.2255 0.090 Uiso 1 1 calc R
C50 C 0.7470(18) 0.7610(9) 0.3940(4) 0.088(3) Uani 1 1 d .
H50A H 0.8579 0.7927 0.4243 0.106 Uiso 1 1 calc R
H50B H 0.5953 0.7791 0.4025 0.106 Uiso 1 1 calc R
C52 C 0.920(3) 0.5927(11) 0.3761(6) 0.217(10) Uani 1 1 d .
H52A H 0.9971 0.6342 0.3463 0.261 Uiso 1 1 calc R
H52B H 0.8766 0.5093 0.3661 0.261 Uiso 1 1 calc R
H52C H 1.0282 0.6081 0.4071 0.261 Uiso 1 1 calc R
C32 C 0.718(4) 0.0886(12) 0.4586(5) 0.300(13) Uani 1 1 d .
H32A H 0.7559 0.0207 0.4403 0.359 Uiso 1 1 calc R
H32B H 0.5511 0.0705 0.4665 0.359 Uiso 1 1 calc R
H32C H 0.8119 0.1092 0.4919 0.359 Uiso 1 1 calc R
C53 C 0.604(2) 0.5760(12) 0.4387(6) 0.198(8) Uani 1 1 d .
H53A H 0.5749 0.4916 0.4332 0.238 Uiso 1 1 calc R
H53B H 0.4556 0.5972 0.4455 0.238 Uiso 1 1 calc R
H53C H 0.7128 0.6036 0.4692 0.238 Uiso 1 1 calc R
C31 C 0.775(3) 0.1916(13) 0.4227(6) 0.144(7) Uani 1 1 d .
H31 H 0.61(2) 0.193(14) 0.416(7) 0.173 Uiso 1 1 calc .
C51 C 0.711(4) 0.6319(14) 0.3889(5) 0.167(9) Uani 1 1 d .
H51 H 0.59(3) 0.602(13) 0.359(6) 0.201 Uiso 1 1 calc .
C33 C 0.822(5) 0.2784(15) 0.4470(7) 0.38(2) Uani 1 1 d .
H33A H 0.9892 0.3150 0.4436 0.451 Uiso 1 1 calc R
H33B H 0.7897 0.2659 0.4845 0.451 Uiso 1 1 calc R
H33C H 0.7281 0.3290 0.4340 0.451 Uiso 1 1 calc R
H21A H 1.3839 0.3450 0.1294 0.08(3) Uiso 1 1 d R
H41A H 1.3456 0.8288 0.1342 0.07(3) 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_3
C1 N1 C5 117.8(7) .
N1 C1 C2 123.8(8) .
C3 C2 C1 118.9(7) .
C2 C3 C4 117.0(7) .
C2 C3 C3 120.7(9) 2_665
C4 C3 C3 122.3(10) 2_665
C3 C4 C5 120.5(7) .
N1 C5 C4 122.0(7) .
C11 N11 C15 116.7(7) .
N11 C11 C12 123.6(8) .
C13 C12 C11 119.9(7) .
C12 C13 C14 117.2(7) .
C12 C13 C13 121.9(9) 2_655
C14 C13 C13 120.9(9) 2_655
C15 C14 C13 118.8(7) .
N11 C15 C14 123.7(7) .
O22 C21 O21 123.2(8) .
O22 C21 C22 125.9(9) .
O21 C21 C22 110.8(8) .
C23 C22 C24 116.5(8) .
C23 C22 C21 114.4(9) .
C24 C22 C21 108.6(7) .
C29 C24 C25 116.4(8) .
C29 C24 C22 121.5(9) .
C25 C24 C22 122.0(9) .
C26 C25 C24 120.7(8) .
C27 C26 C25 122.5(9) .
C26 C27 C28 116.0(8) .
C26 C27 C30 121.9(9) .
C28 C27 C30 122.1(9) .
C29 C28 C27 121.5(8) .
C24 C29 C28 122.9(8) .
C31 C30 C27 117.9(9) .
O42 C41 O41 124.4(8) .
O42 C41 C42 125.8(9) .
O41 C41 C42 109.8(9) .
C43 C42 C41 114.6(9) .
C43 C42 C44 114.0(8) .
C41 C42 C44 111.5(7) .
C45 C44 C49 116.2(8) .
C45 C44 C42 121.7(10) .
C49 C44 C42 122.0(10) .
C44 C45 C46 123.1(9) .
C45 C46 C47 120.7(9) .
C46 C47 C48 118.0(8) .
C46 C47 C50 122.0(9) .
C48 C47 C50 120.1(9) .
C49 C48 C47 118.9(9) .
C48 C49 C44 123.0(9) .
C51 C50 C47 114.8(9) .
C33 C31 C30 134.7(16) .
C33 C31 C32 111.7(15) .
C30 C31 C32 111.4(12) .
C52 C51 C50 114.6(15) .
C52 C51 C53 109.6(13) .
C50 C51 C53 111.6(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.326(9) .
N1 C5 1.329(8) .
C1 C2 1.395(10) .
C2 C3 1.379(9) .
C3 C4 1.391(9) .
C3 C3 1.496(14) 2_665
C4 C5 1.391(10) .
N11 C11 1.328(9) .
N11 C15 1.336(9) .
C11 C12 1.401(10) .
C12 C13 1.369(9) .
C13 C14 1.406(9) .
C13 C13 1.486(14) 2_655
C14 C15 1.398(10) .
O21 C21 1.311(9) .
O22 C21 1.204(9) .
C21 C22 1.524(12) .
C22 C23 1.449(12) .
C22 C24 1.504(12) .
C24 C29 1.360(10) .
C24 C25 1.393(11) .
C25 C26 1.390(11) .
C26 C27 1.369(10) .
C27 C28 1.387(11) .
C27 C30 1.511(11) .
C28 C29 1.372(11) .
C30 C31 1.414(15) .
O41 C41 1.302(9) .
O42 C41 1.199(9) .
C41 C42 1.509(12) .
C42 C43 1.442(12) .
C42 C44 1.530(12) .
C44 C45 1.357(11) .
C44 C49 1.390(11) .
C45 C46 1.366(11) .
C46 C47 1.383(11) .
C47 C48 1.406(11) .
C47 C50 1.517(11) .
C48 C49 1.379(11) .
C50 C51 1.469(16) .
C52 C51 1.42(2) .
C32 C31 1.517(17) .
C53 C51 1.501(16) .
C31 C33 1.12(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184014
