Crystal Structure and Intermolecular Energy for Some Nandrolone Esters.
Mare, Liviu; Muresan-Pop, Marieta; Purcea Lopes, Pompilia Mioara; Turza, Alexandru; Borodi, Gheorghe; Popescu, Violeta; Molecules (Basel, Switzerland) 28 (2023) 7179–; doi:10.3390/molecules28207179

data_1570280
_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         'C26 H38 O3'
_chemical_formula_sum            'C26 H38 O3'
_chemical_formula_weight         398.56
_chemical_name_common            Nandrolone_cypionate
_chemical_name_systematic
19_nortestosterone_17&#x00CE;&#x00B2;_cyclopentanepropionate
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-03
_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            4
_cell_length_a                   7.64320(10)
_cell_length_b                   15.3112(4)
_cell_length_c                   19.7800(4)
_cell_measurement_reflns_used    13856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2050
_cell_measurement_theta_min      4.4550
_cell_volume                     2314.79(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.16a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.16a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.16a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     32.00  64.00   1.00    1.00    --    0.00  38.00   0.00   32
  2  \w    -29.00  25.00   1.00    1.00    --    0.00  76.00-124.42   54
  3  \w    -25.00  25.00   1.00    1.00    --    0.00  38.00   0.00   50
  4  \w    -68.00 -25.00   1.00    1.00    --    0.00 -77.00-120.00   43
  5  \w     32.00  68.00   1.00    1.00    --    0.00  76.00-124.42   36
  6  \w    -20.00  30.00   1.00    1.00    --    0.00 -77.00-120.00   50
  7  \w    -32.00   3.00   1.00    1.00    --    0.00  82.00  52.84   35
  8  \w      7.00  39.00   1.00    1.00    --    0.00  82.00  52.84   32
  9  \w    -20.00   7.00   1.00    1.25    --   28.00 112.00  16.07   27
 10  \w    -17.00   8.00   1.00    1.25    --   28.00 106.00-116.92   25
 11  \w      7.00  32.00   1.00    1.25    --   44.00  89.00  -0.86   25
 12  \w      9.00  34.00   1.00    1.25    --   44.00  86.00 169.86   25
 13  \w      8.00  33.00   1.00    1.25    --   44.00  87.00-129.58   25
 14  \w      9.00  34.00   1.00    1.25    --   44.00  86.00 106.60   25
 15  \w     16.00  41.00   1.00    1.25    --   48.00  81.00  28.73   25
 16  \w     17.00  42.00   1.00    1.25    --   48.00  79.00 -41.85   25
 17  \w     17.00  42.00   1.00    1.25    --   48.00  79.00 -65.59   25
 18  \w     19.00  44.00   1.00    1.25    --   52.00  82.00 -10.88   25
 19  \w     19.00  44.00   1.00    1.25    --   52.00  82.00  74.59   25
 20  \w     14.00  74.00   1.00    1.25    --   54.00 -57.00  60.00   60
 21  \w     25.00  93.00   1.00    1.25    --   54.00-126.00  90.00   68
 22  \w      1.00  74.00   1.00    1.25    --   54.00 -57.00 -90.00   73
 23  \w     10.00  89.00   1.00    1.25    --   54.00 -99.00-150.00   79
 24  \w     27.00  53.00   1.00    1.25    --   54.00  77.00-120.00   26
 25  \w     31.00  67.00   1.00    1.25    --   60.00  77.00-156.60   36
 26  \w     78.00 129.00   1.00    1.25    --   60.00  72.00 144.21   51
 27  \w     33.00  59.00   1.00    1.25    --   60.00  72.00 144.21   26
 28  \w    103.00 129.00   1.00    1.25    --   60.00  77.00-156.60   26
 29  \w     32.00  84.00   1.00    1.25    --   60.00  75.00  69.76   52
 30  \w     99.00 127.00   1.00    1.25    --   60.00  72.00 -33.80   28
 31  \w     34.00  74.00   1.00    1.25    --   60.00  72.00 -33.80   40
 32  \w     31.00  60.00   1.00    1.25    --   60.00  76.00  36.39   29
 33  \w     70.00 130.00   1.00    1.25    --   60.00  77.00 178.45   60
 34  \w     90.00 128.00   1.00    1.25    --   60.00  71.00 -63.73   38
 35  \w     33.00  77.00   1.00    1.25    --   60.00  71.00 -63.73   44
 36  \w     30.00  57.00   1.00    1.25    --   60.00  77.00 178.45   27
 37  \w     32.00  58.00   1.00    1.25    --   60.00  73.00 128.66   26
 38  \w     44.00 110.00   1.00    1.25    --   64.00  55.00 121.54   66
 39  \w     95.00 137.00   1.00    1.25    --   68.00  76.00   2.45   42
 40  \w     39.00  77.00   1.00    1.25    --   68.00  76.00   2.45   38
 41  \w     39.00 126.00   1.00    1.25    --   68.00  75.00-115.17   87
 42  \w    105.00 147.00   1.00    1.25    --   80.00  64.00  44.60   42
 43  \w     57.00  84.00   1.00    1.25    --   80.00  64.00  44.60   27
 44  \w     85.00 116.00   1.00    1.25    --  108.00  64.00  90.00   31
 45  \w     42.00 130.00   1.00    1.25    --  108.00 -64.00 -60.00   88
 46  \w     85.00 147.00   1.00    1.25    --  108.00  64.00 -60.00   62
 47  \w     44.00 107.00   1.00    1.25    --  108.00 -92.00 -90.00   63
 48  \w     79.00 177.00   1.00    1.25    --  108.00  77.00-120.00   98
 49  \w     79.00 157.00   1.00    1.25    --  108.00  77.00 -90.00   78
 50  \w     36.00 102.00   1.00    1.25    --  108.00 -92.00  90.00   66
 51  \w    118.00 178.00   1.00    1.25    --  108.00  77.00 -60.00   60
 52  \w     78.00 104.00   1.00    1.25    --  108.00  77.00 -60.00   26
 53  \w    130.00 172.00   1.00    1.25    --  108.00  77.00   0.00   42
 54  \w     78.00 104.00   1.00    1.25    --  108.00  77.00   0.00   26
 55  \w     78.00 170.00   1.00    1.25    --  108.00  77.00  90.00   92
 56  \w     61.00 112.00   1.00    1.25    --  108.00-112.00-120.00   51
 57  \w     78.00 167.00   1.00    1.25    --  108.00  77.00  30.00   89
 58  \w     78.00 104.00   1.00    1.25    --  108.00  77.00-150.00   26
 59  \w    127.00 170.00   1.00    1.25    --  108.00  77.00 120.00   43
 60  \w     78.00 104.00   1.00    1.25    --  108.00  77.00 120.00   26
 61  \w     79.00 178.00   1.00    1.25    --  108.00  77.00 -30.00   99
 62  \w     78.00 104.00   1.00    1.25    --  108.00  77.00 150.00   26
 63  \w     85.00 165.00   1.00    1.25    --  108.00  64.00-150.00   80
 64  \w     85.00 111.00   1.00    1.25    --  108.00  64.00 -90.00   26
 65  \w     80.00 112.00   1.00    1.25    --  108.00-112.00  30.00   32
 66  \w    123.00 178.00   1.00    1.25    --  108.00  77.00  60.00   55
 67  \w     85.00 111.00   1.00    1.25    --  108.00  64.00  60.00   26
 68  \w     82.00 131.00   1.00    1.25    --  108.00  38.00 150.00   49
 69  \w     78.00 112.00   1.00    1.25    --  108.00  77.00  60.00   34
 70  \w     85.00 140.00   1.00    1.25    --  108.00  64.00   0.00   55
 71  \w     85.00 111.00   1.00    1.25    --  108.00  64.00 -30.00   26
 72  \w     36.00 100.00   1.00    1.25    --  108.00 -92.00 150.00   64
 73  \w     85.00 166.00   1.00    1.25    --  108.00  64.00-180.00   81
 74  \w     85.00 175.00   1.00    1.25    --  108.00  64.00 150.00   90
 75  \w     78.00 104.00   1.00    1.25    --  108.00  77.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0138131000
_diffrn_orient_matrix_UB_12      -0.1003086000
_diffrn_orient_matrix_UB_13      0.0029226000
_diffrn_orient_matrix_UB_21      -0.1991173000
_diffrn_orient_matrix_UB_22      0.0062678000
_diffrn_orient_matrix_UB_23      -0.0110959000
_diffrn_orient_matrix_UB_31      0.0281189000
_diffrn_orient_matrix_UB_32      -0.0047477000
_diffrn_orient_matrix_UB_33      -0.0770319000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34086
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.948
_diffrn_reflns_theta_min         3.651
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.16a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0652
_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/[\s^2^(Fo^2^)+(0.1349P)^2^+0.3755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2089
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3947
_reflns_number_total             4429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            NCyp.cif
_cod_data_source_block           NCyp
_cod_database_code               1570280
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c20 h20 o3'
_reflns_odcompleteness_completeness 99.92
_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:
 C8(H8), C9(H9), C14(H14), C10(H10), C17(H17), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C15(H15A,H15B), C7(H7A,H7B), C1(H1A,H1B),
 C16(H16A,H16B), C20(H20A,H20B), C6(H6A,H6B), C2(H2A,H2B), C21(H21A,H21B),
 C26(H26A,H26B), C25(H25A,H25B), C24(H24A,H24B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              58513
_shelx_hkl_checksum              39738
_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 1.356
_oxdiff_exptl_absorpt_empirical_full_min 0.671