The crystal structure of 17-(bromoethynyl)-17-hydroxy-10, 13-dimethyl- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, C21H27BrO2
Ji, Xiao-Liang; Xie, Feng; Li, Yi-Biao; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 655–657; doi:10.1515/ncrs-2022-0165

data_8107179
_publ_section_title
;
 The crystal structure of 17-(bromoethynyl)-17-hydroxy-10, 13-dimethyl-
 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one,
 C21H27BrO2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              655
_journal_page_last               657
_journal_paper_doi               10.1515/ncrs-2022-0165
_journal_volume                  237
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H27 Br O2'
_chemical_formula_sum            'C21 H27 Br O2'
_chemical_formula_weight         391.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 95.0757(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.62197(14)
_cell_length_b                   11.7640(2)
_cell_length_c                   11.8485(2)
_cell_measurement_reflns_used    4521
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6270
_cell_measurement_theta_min      3.7530
_cell_volume                     919.39(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_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    -65.00  17.00   1.00    1.00    --  -40.73  57.00  30.00   82
  2  \w    -30.00  -3.00   1.00    1.00    --  -40.73 125.00-150.00   27
  3  \w   -114.00 -22.00   1.00    1.00    --  -40.73 -38.00  30.00   92
  4  \w    148.00 175.00   1.00    1.00    --  107.58  30.00  30.00   27
  5  \w    109.00 173.00   1.00    1.00    --  107.58 125.00-120.00   64
  6  \w     97.00 172.00   1.00    1.00    --  107.58 125.00-150.00   75
  7  \w     97.00 174.00   1.00    1.00    --  107.58  45.00   0.00   77
  8  \w     40.00 129.00   1.00    1.00    --  107.58 -45.00-150.00   89
  9  \w     26.00  89.00   1.00    1.00    --  107.58 -95.00-180.00   63
 10  \w   -101.00 -23.00   1.00    1.00    --  -40.98 -57.00 120.00   78
 11  \w    -60.00 -27.00   1.00    1.00    --  -40.98 -57.00  30.00   33
 12  \w     63.00  93.00   1.00    1.00    --   40.98-125.00-150.00   30
 13  \w     23.00  77.00   1.00    1.00    --   40.98-125.00 -60.00   54
 14  \w     30.00  56.00   1.00    1.00    --   40.98-125.00-150.00   26
 15  \w    152.00 178.00   1.00    1.00    --  107.58  61.00 120.00   26
 16  \w     78.00 111.00   1.00    1.00    --  107.58  61.00 120.00   33
 17  \w     83.00 113.00   1.00    1.00    --  107.58  45.00  60.00   30
 18  \w     75.00 101.00   1.00    1.00    --  107.58  77.00  60.00   26
 19  \w     82.00  96.00   1.00    1.00    --  107.58  45.00  90.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1749550000
_diffrn_orient_matrix_UB_12      -0.0075453000
_diffrn_orient_matrix_UB_13      0.0944229000
_diffrn_orient_matrix_UB_21      -0.1434364000
_diffrn_orient_matrix_UB_22      -0.0566317000
_diffrn_orient_matrix_UB_23      0.0788035000
_diffrn_orient_matrix_UB_31      0.0576297000
_diffrn_orient_matrix_UB_32      -0.1178203000
_diffrn_orient_matrix_UB_33      -0.0439310000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5032
_diffrn_reflns_point_group_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.787
_diffrn_reflns_theta_min         3.745
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0487P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.643
_reflns_Friedel_fraction_full    0.753
_reflns_Friedel_fraction_max     0.694
_reflns_number_gt                3117
_reflns_number_total             3136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0165_suppl.cif
_cod_data_source_block           b5
_cod_database_code               8107179
_reflns_odcompleteness_completeness 100.00
_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:
 C7(H7), C8(H8), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              17613
_shelx_hkl_checksum              61778
_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 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.456