#------------------------------------------------------------------------------
#$Date: 2023-11-07 05:03:15 +0200 (Tue, 07 Nov 2023) $
#$Revision: 287465 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/02/1570281.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_1570281
loop_
_publ_author_name
'Mare, Liviu'
'Muresan-Pop, Marieta'
'Purcea Lopes, Pompilia Mioara'
'Turza, Alexandru'
'Borodi, Gheorghe'
'Popescu, Violeta'
_publ_section_title
;
 Crystal Structure and Intermolecular Energy for Some Nandrolone Esters.
;
_journal_issue                   20
_journal_name_full               'Molecules (Basel, Switzerland)'
_journal_page_first              7179
_journal_paper_doi               10.3390/molecules28207179
_journal_volume                  28
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H34 O3'
_chemical_formula_sum            'C27 H34 O3'
_chemical_formula_weight         404.52
_chemical_name_common            Nandrolone_phenylpropionate
_chemical_name_systematic
19_Nortestosterone_17Î²_phenylpropionate
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.09590(10)
_cell_length_b                   8.09590(10)
_cell_length_c                   71.2184(14)
_cell_measurement_reflns_used    4810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.3220
_cell_measurement_theta_min      4.9660
_cell_volume                     4667.91(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.4335
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω      2.00  65.00   0.75    0.87    --    0.00  57.00 -90.00   84
  2  ω    -28.00  18.50   0.75    0.87    --    0.00 -57.00 -30.00   62
  3  ω     -9.00  18.00   0.75    0.87    --    0.00  66.00-136.00   36
  4  ω     34.75 127.00   0.75    3.49    --   54.00  19.00   0.00  123
  5  ω    -14.00  27.25   0.75    3.49    --   54.00 -66.00  88.00   55
  6  ω    -18.00  69.00   0.75    3.49    --   54.00 -38.00-180.00  116
  7  ω     -9.00  78.00   0.75    3.49    --   54.00 -38.00 -30.00  116
  8  ω    107.00 139.25   0.75    3.49    --  108.00 112.00 -30.00   43
  9  ω    118.00 169.00   0.75    3.49    --  108.00 112.00 -60.00   68
 10  ω     37.00 107.50   0.75    3.49    --  108.00-112.00 -60.00   94
 11  ω     93.00 174.00   0.75    3.49    --  108.00  50.00  30.00  108
 12  ω     88.00 174.25   0.75    3.49    --  108.00  77.00  90.00  115
 13  ω     45.00 122.25   0.75    3.49    --  108.00 -50.00 -60.00  103
 14  ω    132.00 169.50   0.75    3.49    --  108.00  77.00-150.00   50
 15  ω     83.00 109.25   0.75    3.49    --  108.00  77.00-150.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1353425000
_diffrn_orient_matrix_UB_12      -0.1325212000
_diffrn_orient_matrix_UB_13      -0.0020323000
_diffrn_orient_matrix_UB_21      -0.0338717000
_diffrn_orient_matrix_UB_22      0.0584070000
_diffrn_orient_matrix_UB_23      -0.0202271000
_diffrn_orient_matrix_UB_31      0.1294742000
_diffrn_orient_matrix_UB_32      -0.1233336000
_diffrn_orient_matrix_UB_33      -0.0074006000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       85
_diffrn_reflns_limit_l_min       -86
_diffrn_reflns_number            16752
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.643
_diffrn_reflns_theta_min         4.968
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       plate
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 700 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1301P)²+0.2824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2338
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2542
_reflns_number_total             4401
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            NPhp.cif
_cod_data_source_block           NPhp
_cod_original_cell_volume        4667.91(15)
_cod_database_code               1570281
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c23 o3 h30'
_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.
;
_exptl_absorpt_special_details   ad
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C8(H8), C9(H9), C10(H10), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C11(H11A,H11B), C16(H16A,H16B), C15(H15A,H15B),
 C20(H20A,H20B), C12(H12A,H12B), C21(H21A,H21B), C1(H1A,H1B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C4(H4), C26(H26), C23(H23), C27(H27), C24(H24)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.767
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C14 C 0.8346(6) 0.9762(5) 0.05756(6) 0.0977(12) Uani 1 1 d . . . . .
H14 H 0.725422 0.984984 0.063431 0.117 Uiso 1 1 calc R . . . .
C5 C 1.0453(7) 1.1519(6) 0.10995(6) 0.1109(14) Uani 1 1 d . . . . .
O2 O 0.6807(5) 1.0460(7) 0.00989(4) 0.1441(15) Uani 1 1 d . . . . .
C13 C 0.8297(6) 1.0886(6) 0.04016(6) 0.1023(13) Uani 1 1 d . . . . .
C8 C 0.9592(6) 1.0316(5) 0.07246(6) 0.0957(12) Uani 1 1 d . . . . .
H8 H 1.069945 1.033222 0.066902 0.115 Uiso 1 1 calc R . . . .
C7 C 0.9593(8) 0.9169(5) 0.08937(6) 0.1154(16) Uani 1 1 d . . . . .
H7A H 0.848201 0.909559 0.094394 0.138 Uiso 1 1 calc R . . . .
H7B H 0.992477 0.807183 0.085409 0.138 Uiso 1 1 calc R . . . .
C9 C 0.9135(7) 1.2065(5) 0.07875(6) 0.1049(14) Uani 1 1 d . . . . .
H9 H 0.803949 1.199717 0.084551 0.126 Uiso 1 1 calc R . . . .
C6 C 1.0755(9) 0.9769(6) 0.10465(6) 0.1265(18) Uani 1 1 d . . . . .
H6A H 1.062199 0.907663 0.115665 0.152 Uiso 1 1 calc R . . . .
H6B H 1.188533 0.965416 0.100328 0.152 Uiso 1 1 calc R . . . .
C11 C 0.8980(8) 1.3248(5) 0.06187(7) 0.1222(18) Uani 1 1 d . . . . .
H11A H 0.857232 1.430606 0.066257 0.147 Uiso 1 1 calc R . . . .
H11B H 1.006725 1.342452 0.056507 0.147 Uiso 1 1 calc R . . . .
C10 C 1.0323(8) 1.2715(5) 0.09388(6) 0.1176(16) Uani 1 1 d . . . . .
H10 H 1.142010 1.282312 0.088203 0.141 Uiso 1 1 calc R . . . .
C25 C 0.6402(12) 1.4323(8) -0.07920(8) 0.143(2) Uani 1 1 d . . . . .
H25 H 0.647411 1.464389 -0.091708 0.171 Uiso 1 1 calc R . . . .
C4 C 1.0336(7) 1.1998(7) 0.12785(6) 0.1191(16) Uani 1 1 d . . . . .
H4 H 1.030704 1.118183 0.137038 0.143 Uiso 1 1 calc R . . . .
C16 C 0.7520(7) 0.8121(7) 0.03055(7) 0.1210(16) Uani 1 1 d . . . . .
H16A H 0.823946 0.783258 0.020168 0.145 Uiso 1 1 calc R . . . .
H16B H 0.657076 0.738979 0.030474 0.145 Uiso 1 1 calc R . . . .
O1 O 1.0030(7) 1.4023(6) 0.15038(6) 0.175(2) Uani 1 1 d . . . . .
C15 C 0.8448(7) 0.8012(6) 0.04936(6) 0.1112(15) Uani 1 1 d . . . . .
H15A H 0.792511 0.721862 0.057665 0.133 Uiso 1 1 calc R . . . .
H15B H 0.958856 0.768749 0.047412 0.133 Uiso 1 1 calc R . . . .
C17 C 0.6983(7) 0.9917(8) 0.02929(6) 0.1165(16) Uani 1 1 d . . . . .
H17 H 0.591832 1.004181 0.035680 0.140 Uiso 1 1 calc R . . . .
C20 C 0.5392(11) 1.1479(8) -0.01617(9) 0.154(2) Uani 1 1 d . . . . .
H20A H 0.589037 1.058498 -0.023253 0.185 Uiso 1 1 calc R . . . .
H20B H 0.424405 1.156106 -0.019955 0.185 Uiso 1 1 calc R . . . .
C18 C 0.9922(6) 1.0892(7) 0.02906(7) 0.1165(15) Uani 1 1 d . . . . .
H18A H 1.080371 1.126108 0.037042 0.175 Uiso 1 1 calc GR . . . .
H18B H 0.982328 1.162273 0.018510 0.175 Uiso 1 1 calc GR . . . .
H18C H 1.015614 0.979446 0.024697 0.175 Uiso 1 1 calc GR . . . .
C26 C 0.4898(10) 1.4251(8) -0.07054(9) 0.142(2) Uani 1 1 d . . . . .
H26 H 0.393999 1.452359 -0.077036 0.170 Uiso 1 1 calc R . . . .
C12 C 0.7823(8) 1.2595(7) 0.04656(7) 0.1282(19) Uani 1 1 d . . . . .
H12A H 0.670112 1.257417 0.051344 0.154 Uiso 1 1 calc R . . . .
H12B H 0.785022 1.334036 0.035901 0.154 Uiso 1 1 calc R . . . .
C22 C 0.6258(10) 1.3371(6) -0.04182(7) 0.1251(18) Uani 1 1 d . . . . .
C23 C 0.7726(9) 1.3468(7) -0.05099(8) 0.1305(18) Uani 1 1 d . . . . .
H23 H 0.869882 1.322110 -0.044642 0.157 Uiso 1 1 calc R . . . .
C21 C 0.6191(12) 1.2943(9) -0.02062(8) 0.163(3) Uani 1 1 d . . . . .
H21A H 0.731372 1.288472 -0.015900 0.195 Uiso 1 1 calc R . . . .
H21B H 0.564180 1.383979 -0.014090 0.195 Uiso 1 1 calc R . . . .
C27 C 0.4825(9) 1.3764(7) -0.05181(8) 0.1323(18) Uani 1 1 d . . . . .
H27 H 0.380557 1.369811 -0.045846 0.159 Uiso 1 1 calc R . . . .
C1 C 0.9780(12) 1.4433(6) 0.10066(8) 0.168(3) Uani 1 1 d . . . . .
H1A H 1.006137 1.524252 0.091141 0.201 Uiso 1 1 calc R . . . .
H1B H 0.858957 1.444134 0.102160 0.201 Uiso 1 1 calc R . . . .
C24 C 0.7786(10) 1.3927(7) -0.06954(8) 0.1295(18) Uani 1 1 d . . . . .
H24 H 0.880225 1.396611 -0.075610 0.155 Uiso 1 1 calc R . . . .
C3 C 1.0253(9) 1.3666(8) 0.13378(9) 0.1343(19) Uani 1 1 d . . . . .
C19 C 0.5468(10) 1.1073(9) 0.00423(8) 0.142(2) Uani 1 1 d . . . . .
C2 C 1.0563(12) 1.4921(7) 0.11876(10) 0.168(3) Uani 1 1 d . . . . .
H2A H 1.012502 1.598033 0.122725 0.202 Uiso 1 1 calc R . . . .
H2B H 1.174426 1.504454 0.116938 0.202 Uiso 1 1 calc R . . . .
O3 O 0.4363(8) 1.1331(12) 0.01460(8) 0.270(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C8 C14 C13 113.7(4) . . ?
C8 C14 C15 119.9(4) . . ?
C15 C14 C13 104.0(4) . . ?
C6 C5 C10 115.6(4) . . ?
C4 C5 C6 122.1(4) . . ?
C4 C5 C10 122.3(4) . . ?
C19 O2 C17 120.5(4) . . ?
C17 C13 C14 97.0(4) . . ?
C17 C13 C18 109.6(4) . . ?
C18 C13 C14 113.2(4) . . ?
C12 C13 C14 107.8(4) . . ?
C12 C13 C17 116.5(5) . . ?
C12 C13 C18 111.8(4) . . ?
C7 C8 C14 111.7(4) . . ?
C7 C8 C9 109.5(3) . . ?
C9 C8 C14 108.3(4) . . ?
C6 C7 C8 111.9(4) . . ?
C8 C9 C11 111.4(3) . . ?
C8 C9 C10 111.8(4) . . ?
C10 C9 C11 112.6(4) . . ?
C5 C6 C7 112.6(5) . . ?
C12 C11 C9 113.0(4) . . ?
C5 C10 C9 110.9(4) . . ?
C5 C10 C1 111.4(4) . . ?
C1 C10 C9 110.6(5) . . ?
C24 C25 C26 119.9(5) . . ?
C5 C4 C3 124.4(5) . . ?
C17 C16 C15 104.3(4) . . ?
C14 C15 C16 104.6(4) . . ?
O2 C17 C13 113.1(4) . . ?
O2 C17 C16 111.9(4) . . ?
C16 C17 C13 105.2(4) . . ?
C21 C20 C19 113.1(6) . . ?
C25 C26 C27 118.9(7) . . ?
C13 C12 C11 112.1(4) . . ?
C23 C22 C21 120.8(7) . . ?
C23 C22 C27 117.9(5) . . ?
C27 C22 C21 121.2(6) . . ?
C22 C23 C24 120.6(6) . . ?
C20 C21 C22 115.4(6) . . ?
C26 C27 C22 121.1(6) . . ?
C2 C1 C10 113.0(6) . . ?
C25 C24 C23 121.6(6) . . ?
C4 C3 C2 115.3(5) . . ?
O1 C3 C4 121.2(6) . . ?
O1 C3 C2 123.5(6) . . ?
O2 C19 C20 115.8(6) . . ?
O3 C19 O2 121.5(6) . . ?
O3 C19 C20 122.7(7) . . ?
C1 C2 C3 111.5(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C14 C13 1.538(5) . ?
C14 C8 1.531(6) . ?
C14 C15 1.535(6) . ?
C5 C6 1.487(7) . ?
C5 C10 1.503(6) . ?
C5 C4 1.336(6) . ?
O2 C17 1.457(6) . ?
O2 C19 1.259(7) . ?
C13 C17 1.532(7) . ?
C13 C18 1.535(6) . ?
C13 C12 1.506(7) . ?
C8 C7 1.521(5) . ?
C8 C9 1.531(6) . ?
C7 C6 1.518(8) . ?
C9 C11 1.542(6) . ?
C9 C10 1.537(7) . ?
C11 C12 1.532(8) . ?
C10 C1 1.536(7) . ?
C25 C26 1.366(9) . ?
C25 C24 1.354(9) . ?
C4 C3 1.416(8) . ?
C16 C15 1.539(7) . ?
C16 C17 1.520(8) . ?
O1 C3 1.231(7) . ?
C20 C21 1.387(9) . ?
C20 C19 1.491(8) . ?
C26 C27 1.392(8) . ?
C22 C23 1.358(8) . ?
C22 C21 1.550(7) . ?
C22 C27 1.397(9) . ?
C23 C24 1.373(8) . ?
C1 C2 1.490(9) . ?
C3 C2 1.496(9) . ?
C19 O3 1.179(7) . ?
