The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one, C18H21NO4
Raičević, Vidak; Radnović, Nikola D.; Rodić, Marko V.; Radulović, Niko S.; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 277–280; doi:10.1515/ncrs-2022-0602

data_8107416
_publ_section_title
;
 The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one,
 C18H21NO4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              277
_journal_page_last               280
_journal_paper_doi               10.1515/ncrs-2022-0602
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_melting_point          435
_chemical_name_common            2-nitroestrone
_chemical_name_systematic        3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6891(2)
_cell_length_b                   11.8375(2)
_cell_length_c                   25.4410(4)
_cell_measurement_reflns_used    7093
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      71.9770
_cell_measurement_theta_min      3.4730
_cell_volume                     3219.11(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 [1]'
_computing_data_collection       'CrysAlisPro 1.171.42.49 [1]'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 [1]'
_computing_molecular_graphics    'PLATON [4]'
_computing_publication_material  'PLATON [4]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2018/2 [2]'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_detector_type            'Sapphire3 (Oxford Diffraction)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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      3.00  70.00   1.00   15.00    --   36.53 -99.00 150.00   67
  2  \w     38.00  92.00   1.00   15.00    --   36.53  57.00  30.00   54
  3  \w    -29.00  36.00   1.00   15.00    --   36.53 -57.00-120.00   65
  4  \w     67.00 120.00   1.00   60.00    --  108.00 -45.00  60.00   53
  5  \w    103.00 176.00   1.00   60.00    --  108.00  77.00-120.00   73
  6  \w    110.00 176.00   1.00   60.00    --  108.00  77.00 -30.00   66
  7  \w     43.00 105.00   1.00   60.00    --  108.00 -94.00-120.00   62
  8  \w     58.00  95.00   1.00   60.00    --  108.00 -94.00   0.00   37
  9  \f      0.00 270.00   1.00    0.50   0.00   0.00   0.00    --   270
 10  \w     25.00  67.00   1.00   11.00    --   36.66-125.00  90.00   42
 11  \w    -13.00  54.00   1.00   11.00    --   36.66 -77.00-150.00   67
 12  \w     49.00 123.00   1.00   60.00    --  108.00 -45.00-120.00   74
 13  \w    135.00 161.00   1.00   60.00    --  108.00  61.00 -60.00   26
 14  \w     90.00 116.00   1.00   60.00    --  108.00  61.00 -60.00   26
 15  \w     41.00  87.00   1.00   60.00    --  108.00 -94.00 120.00   46
 16  \w    126.00 176.00   1.00   60.00    --  108.00  15.00 -60.00   50
 17  \w     71.00 102.00   1.00   60.00    --  108.00  15.00 -60.00   31
 18  \w     17.00 106.00   1.00   11.00    --   36.66  37.00-120.00   89
 19  \w     20.00 104.00   1.00   11.00    --   36.66  57.00 120.00   84
 20  \w     17.00 106.00   1.00   11.00    --   36.66  37.00 -30.00   89
 21  \w     13.00 104.00   1.00   11.00    --   36.66  72.00 -17.00   91
 22  \w    -31.00  53.00   1.00   11.00    --   36.66 -57.00  60.00   84
 23  \w    -30.00  61.00   1.00   11.00    --   36.66 -72.00-148.00   91
 24  \w    -18.00  63.00   1.00   11.00    --   36.66 -77.00 -30.00   81
 25  \w     87.00 112.00   1.00   60.00    --  108.00  30.00  60.00   25
 26  \f     60.00 330.00   1.00    0.50   0.00   0.00   0.00    --   270
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0099483000
_diffrn_orient_matrix_UB_12      0.0119080000
_diffrn_orient_matrix_UB_13      -0.0601536000
_diffrn_orient_matrix_UB_21      0.0855739000
_diffrn_orient_matrix_UB_22      -0.1036786000
_diffrn_orient_matrix_UB_23      -0.0069369000
_diffrn_orient_matrix_UB_31      -0.1155709000
_diffrn_orient_matrix_UB_32      -0.0777562000
_diffrn_orient_matrix_UB_33      0.0000237000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11459
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.943
_diffrn_reflns_theta_min         3.475
_diffrn_source
'fine-focus sealed X-ray tube (Oxford Diffraction)'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.

Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.405
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1019 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0483
_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/[\s^2^(Fo^2^)+(0.0959P)^2^+0.2933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2673
_reflns_number_total             3106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0602_suppl.cif
_cod_data_source_block           Nitrovani_abs_a
_cod_database_code               8107416
_shelx_estimated_absorpt_t_min   0.751
_shelx_estimated_absorpt_t_max   0.886
_shelx_res_checksum              13946
_shelx_hkl_checksum              60146