Crystal structure of 4-(((2-(3-(1-(3-(3-cyanophenyl)-6-oxopyridazin-1(6H)-yl)ethyl)phenyl) pyrimidin-5-yl)oxy)methyl)-1-methylpiperidin-1-ium chloride monohydrate, C30H33N6O2Cl
Yao, Han; Yan, Ming; Li, Xingshu; Hu, Jinhui; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 783–785; doi:10.1515/ncrs-2022-0087

data_8107215
_publ_section_title
;
 Crystal structure of
 4-(((2-(3-(1-(3-(3-cyanophenyl)-6-oxopyridazin-1(6H)-yl)ethyl)phenyl)
 pyrimidin-5-yl)oxy)methyl)-1-methylpiperidin-1-ium chloride monohydrate,
 C30H33N6O2Cl
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              783
_journal_page_last               785
_journal_paper_doi               10.1515/ncrs-2022-0087
_journal_volume                  237
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl, C30 H31 N6 O2, H2 O'
_chemical_formula_sum            'C30 H33 Cl N6 O3'
_chemical_formula_weight         561.07
_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                 101.730(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.7983(8)
_cell_length_b                   7.3771(3)
_cell_length_c                   14.3578(7)
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.0490
_cell_measurement_theta_min      3.2410
_cell_volume                     1430.98(13)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     29.00  71.00   1.00    1.20    --   40.73-121.00 -63.00   42
  2  \w    105.00 136.00   1.00    1.00    --  106.95 -61.00-150.00   31
  3  \w     62.00 178.00   1.00    1.00    --  106.95  15.00 -90.00  116
  4  \w     84.00 124.00   1.00    1.00    --  106.95 -45.00  90.00   40
  5  \w     88.00 146.00   1.00    1.00    --  106.95  61.00 150.00   58
  6  \w     40.00  66.00   1.00    1.00    --  106.95 -45.00  90.00   26
  7  \w     24.00 105.00   1.00    1.00    --  106.95 -94.00 -60.00   81
  8  \w     37.00  79.00   1.00    1.00    --  106.95 -61.00-150.00   42
  9  \w   -106.00 -17.00   1.00    1.20    --  -40.73 -38.00  30.00   89
 10  \w   -113.00 -22.00   1.00    1.20    --  -40.73 -38.00 -60.00   91
;
_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      -0.0647453000
_diffrn_orient_matrix_UB_12      0.0025427000
_diffrn_orient_matrix_UB_13      -0.1009697000
_diffrn_orient_matrix_UB_21      -0.0913935000
_diffrn_orient_matrix_UB_22      -0.0491152000
_diffrn_orient_matrix_UB_23      0.0411942000
_diffrn_orient_matrix_UB_31      -0.0212792000
_diffrn_orient_matrix_UB_32      0.2029209000
_diffrn_orient_matrix_UB_33      0.0111453000
_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  0.0498
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4900
_diffrn_reflns_point_group_measured_fraction_full 0.746
_diffrn_reflns_point_group_measured_fraction_max 0.746
_diffrn_reflns_theta_full        64.958
_diffrn_reflns_theta_max         64.958
_diffrn_reflns_theta_min         3.144
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57346
_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    1.302
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.0036(5)
_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   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0486P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.444
_reflns_Friedel_fraction_max     0.444
_reflns_number_gt                3225
_reflns_number_total             3637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0087_suppl.cif
_cod_data_source_block           hy0102
_cod_database_code               8107215
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.804
_reflns_odcompleteness_completeness 99.93
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O00U(H00V,H00W)
2.b Ternary CH refined with riding coordinates:
 N007(H007), C00A(H00A), C00K(H00K)
2.c Secondary CH2 refined with riding coordinates:
 C00H(H00B,H00C), C00L(H00D,H00H), C00O(H00I,H00J), C00Q(H00L,H00M), C00W(H00T,
 H00U)
2.d Aromatic/amide H refined with riding coordinates:
 C009(H009), C00E(H00E), C00F(H00F), C00G(H00G), C00N(H00N), C00R(H00R),
 C00S(H00S), C00Y(H00Y), C00Z(H00Z), C012(H012), C013(H013), C014(H014)
2.e Idealised Me refined as rotating group:
 C00T(H00O,H00P,H00Q), C010(H01A,H01B,H01C)
;
_shelx_res_checksum              79932
_shelx_hkl_checksum              14671
_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 1.569
_oxdiff_exptl_absorpt_empirical_full_min 0.488