Crystal structure of (8R,10R,14R,Z)-12-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one–water (2/1), C37H56NO4.5
Luo, Qin; Meng, Qing-Guo; Hou, Gui-Ge; Jiang, Sheng; Jin, Yong-Sheng; Gao, Yue; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 1223–1226; doi:10.1515/ncrs-2021-0284

data_8104571
_publ_section_title
;
 Crystal structure of
 (8R,10R,14R,Z)-12-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one--water
 (2/1), C37H56NO4.5
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1223
_journal_page_last               1226
_journal_paper_doi               10.1515/ncrs-2021-0284
_journal_volume                  236
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C37 H55 N O4, 0.5(H2 O)'
_chemical_formula_sum            'C37 H56 N O4.5'
_chemical_formula_weight         586.82
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.43680(10)
_cell_length_b                   10.43680(10)
_cell_length_c                   61.5166(11)
_cell_measurement_reflns_used    4614
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      72.9920
_cell_measurement_theta_min      2.8400
_cell_volume                     6700.81(15)
_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 (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_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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    -63.00 -30.00   0.75    1.00    --  -40.98  38.00-120.00   44
  2  \w   -106.00 -16.75   0.75    1.00    --  -40.98 -57.00 -60.00  119
  3  \w    100.00 164.50   0.75    2.00    --  106.95 125.00 120.00   86
  4  \w    148.00 175.00   0.75    2.00    --  106.95 100.00  41.00   36
  5  \w    112.00 144.25   0.75    2.00    --  106.95 100.00  41.00   43
  6  \w    146.00 172.25   0.75    2.00    --  106.95 125.00-180.00   35
  7  \w     35.00 118.25   0.75    2.00    --  106.95-125.00   0.00  111
;
_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      -0.0592175000
_diffrn_orient_matrix_UB_12      -0.1350280000
_diffrn_orient_matrix_UB_13      -0.0013998000
_diffrn_orient_matrix_UB_21      0.0552765000
_diffrn_orient_matrix_UB_22      -0.0158649000
_diffrn_orient_matrix_UB_23      -0.0230673000
_diffrn_orient_matrix_UB_31      0.1233595000
_diffrn_orient_matrix_UB_32      -0.0574792000
_diffrn_orient_matrix_UB_33      0.0096618000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       76
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            14308
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.625
_diffrn_reflns_theta_min         2.873
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53594
_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    1.163
_exptl_crystal_description       block
_exptl_crystal_F_000             2568
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.00057(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         6554
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0404P)^2^+1.9062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5487
_reflns_number_total             6554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0284_suppl.cif
_cod_data_source_block           w1_3
_cod_original_cell_volume        6700.80(18)
_cod_original_formula_sum        'C37 H56 N O4.50'
_cod_database_code               8104571
_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, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C9') \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(O1)=Sof(H1)=Sof(O3)=Sof(H5B)=Sof(C6')=Sof(H6'A)=Sof(H6'B)=Sof(C7')=
 Sof(H7'A)=Sof(H7'B)=Sof(C8')=Sof(C9')=Sof(H9')=Sof(C11')=Sof(H11C)=Sof(H11D)=
 Sof(C12')=Sof(H12')=Sof(C13')=Sof(H13')=Sof(C14')=Sof(C15')=Sof(H15C)=
 Sof(H15D)=Sof(C16')=Sof(H16C)=Sof(H16D)=Sof(C17')=Sof(H17')=Sof(C18')=
 Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C20')=Sof(C21')=Sof(C22')=Sof(H22C)=
 Sof(H22D)=Sof(C23')=Sof(H23C)=Sof(H23D)=Sof(C24')=Sof(H24C)=Sof(H24D)=
 Sof(C25')=Sof(H25D)=Sof(H25E)=Sof(H25F)=Sof(C26')=Sof(H26D)=Sof(H26E)=
 Sof(H26F)=Sof(C27')=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(C30')=Sof(H30D)=
 Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(O1')=Sof(H1')=Sof(O3')=Sof(H5A)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=
 Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18A)=Sof(H18B)=
 Sof(H18C)=Sof(C20)=Sof(C21)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=
 Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(1)
 Fixed Sof: H5C(0.5) H5D(0.5)
4.a Free rotating group:
 O5(H5C,H5D)
4.b Ternary CH refined with riding coordinates:
 C5(H5A), C5(H5B), C9(H9), C9'(H9'), C12(H12), C12'(H12'), C13(H13),
 C13'(H13'), C17(H17), C17'(H17')
4.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C6'(H6'A,H6'B), C7(H7A,H7B), C7'(H7'A,H7'B),
 C11(H11A,H11B), C11'(H11C,H11D), C15(H15A,H15B), C15'(H15C,H15D), C16(H16A,
 H16B), C16'(H16C,H16D), C22(H22A,H22B), C22'(H22C,H22D), C23(H23A,H23B),
 C23'(H23C,H23D), C24(H24A,H24B), C24'(H24C,H24D)
4.d Aromatic/amide H refined with riding coordinates:
 C31(H31), C34(H34), C35(H35), C36(H36)
4.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18'(H18D,H18E,H18F), C19(H19A,H19B,H19C), C25(H25A,H25B,
 H25C), C25'(H25D,H25E,H25F), C26(H26A,H26B,H26C), C26'(H26D,H26E,H26F),
 C27(H27A,H27B,H27C), C27'(H27D,H27E,H27F), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C30'(H30D,H30E,H30F), C37(H37A,H37B,H37C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1'(H1')
;
_shelx_res_checksum              72194
_shelx_hkl_checksum              80538
_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 1.512
_oxdiff_exptl_absorpt_empirical_full_min 0.428