#------------------------------------------------------------------------------
#$Date: 2021-02-27 08:14:56 +0200 (Sat, 27 Feb 2021) $
#$Revision: 262301 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/07/1560706.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1560706
loop_
_publ_author_name
'Andreev, Stanislav'
'Schollmeyer, Dieter'
'Koch, Pierre'
_publ_section_title
;
 1-{3-[(7-Fluoro-9H-pyrimido[4,5-b]indol-4-yl)(methyl)amino]piperidin-1-yl}propan-1-one
;
_journal_coeditor_code           BT4108
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x210159
_journal_paper_doi               10.1107/S2414314621001590
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C19 H22 F N5 O'
_chemical_formula_moiety         'C19 H22 F N5 O'
_chemical_formula_sum            'C19 H22 F N5 O'
_chemical_formula_weight         355.41
_chemical_name_systematic
1-{3-[(7-Fluoro-9H-pyrimido[4,5-b]indol-4-yl)(methyl)amino]piperidin-1-yl}propan-1-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6982(3)
_cell_length_b                   19.8473(8)
_cell_length_c                   16.7642(6)
_cell_measurement_reflns_used    7975
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.38
_cell_volume                     3559.5(2)
_computing_cell_refinement
;
X-Area Recipe (Stoe & Cie, 2019)
;
_computing_data_collection
;
X-Area WinXpose (Stoe & Cie, 2019)
;
_computing_data_reduction
;
X-Area Integrate (Stoe & Cie, 2019)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.894
_diffrn_reflns_theta_min         2.385
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.410
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0689
_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/[σ²(Fo²)+(0.0822P)²+2.3561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1940
_reflns_number_gt                2840
_reflns_number_total             4202
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4108sup1.cif
_cod_data_source_block           I
_cod_database_code               1560706
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.03835(15) 0.75389(8) 0.26711(10) 0.0344(4) Uani d 1 . .
N N1 0.0797(2) 0.56013(11) 0.43722(12) 0.0247(5) Uani d 1 . .
H H1 0.011506 0.562102 0.466503 0.030 Uiso calc 1 . .
C C2 0.1147(2) 0.60634(12) 0.38014(14) 0.0224(5) Uani d 1 . .
C C3 0.0481(2) 0.66282(13) 0.35527(14) 0.0243(5) Uani d 1 . .
H H3 -0.028161 0.676063 0.379652 0.029 Uiso calc 1 . .
C C4 0.1002(2) 0.69815(13) 0.29309(15) 0.0260(5) Uani d 1 . .
C C5 0.2099(3) 0.67981(13) 0.25432(16) 0.0272(5) Uani d 1 . .
H H5 0.239394 0.705203 0.210137 0.033 Uiso calc 1 . .
C C6 0.2757(2) 0.62393(13) 0.28097(15) 0.0259(5) Uani d 1 . .
H H6 0.351084 0.610925 0.255311 0.031 Uiso calc 1 . .
C C7 0.2302(2) 0.58663(12) 0.34613(14) 0.0221(5) Uani d 1 . .
C C8 0.2673(2) 0.52527(12) 0.38809(14) 0.0213(5) Uani d 1 . .
C C9 0.3654(2) 0.47773(12) 0.38893(14) 0.0218(5) Uani d 1 . .
N N10 0.3530(2) 0.42059(11) 0.43277(13) 0.0255(5) Uani d 1 . .
C C11 0.2515(2) 0.41287(13) 0.47767(15) 0.0256(5) Uani d 1 . .
H H11 0.245845 0.371894 0.506735 0.031 Uiso calc 1 . .
N N12 0.15664(19) 0.45588(11) 0.48670(12) 0.0250(5) Uani d 1 . .
C C13 0.1679(2) 0.51100(13) 0.44078(14) 0.0230(5) Uani d 1 . .
N N14 0.47433(18) 0.48402(10) 0.34654(12) 0.0225(4) Uani d 1 . .
C C15 0.5310(2) 0.54981(13) 0.33467(16) 0.0283(6) Uani d 1 . .
H H15A 0.612776 0.551050 0.360984 0.042 Uiso calc 1 . .
H H15B 0.476882 0.584631 0.357578 0.042 Uiso calc 1 . .
H H15C 0.541595 0.558115 0.277441 0.042 Uiso calc 1 . .
C C16 0.5572(2) 0.42482(13) 0.34154(15) 0.0252(5) Uani d 1 . .
H H16 0.503095 0.383843 0.338129 0.030 Uiso calc 1 . .
C C17 0.6387(3) 0.42663(14) 0.26687(16) 0.0289(6) Uani d 1 . .
H H17A 0.691916 0.467432 0.267526 0.035 Uiso calc 1 . .
H H17B 0.585136 0.428388 0.218752 0.035 Uiso calc 1 . .
C C18 0.7214(3) 0.36317(14) 0.26433(16) 0.0308(6) Uani d 1 . .
H H18A 0.668171 0.322908 0.256490 0.037 Uiso calc 1 . .
H H18B 0.779753 0.366247 0.218634 0.037 Uiso calc 1 . .
C C19 0.7956(2) 0.35565(14) 0.34126(15) 0.0291(6) Uani d 1 . .
H H19A 0.842958 0.312818 0.340020 0.035 Uiso calc 1 . .
H H19B 0.856282 0.393090 0.345791 0.035 Uiso calc 1 . .
N N20 0.7121(2) 0.35610(11) 0.41082(13) 0.0275(5) Uani d 1 . .
C C21 0.6384(2) 0.41798(13) 0.41636(15) 0.0272(6) Uani d 1 . .
H H21A 0.694825 0.457341 0.420976 0.033 Uiso calc 1 . .
H H21B 0.584720 0.416496 0.464414 0.033 Uiso calc 1 . .
C C22 0.6811(2) 0.29723(13) 0.44725(15) 0.0261(5) Uani d 1 . .
O O23 0.72866(19) 0.24321(10) 0.42863(11) 0.0328(5) Uani d 1 . .
C C24 0.5879(3) 0.30135(14) 0.51579(16) 0.0317(6) Uani d 1 . .
H H24A 0.610597 0.339869 0.550410 0.038 Uiso calc 1 . .
H H24B 0.503685 0.310256 0.493727 0.038 Uiso calc 1 . .
C C25 0.5829(3) 0.23828(16) 0.56585(18) 0.0421(8) Uani d 1 . .
H H25A 0.554350 0.200474 0.532942 0.063 Uiso calc 1 . .
H H25B 0.524624 0.244955 0.610271 0.063 Uiso calc 1 . .
H H25C 0.666367 0.228412 0.586876 0.063 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 N1 C2 . . 108.6(2) ?
C13 N1 H1 . . 125.7 ?
C2 N1 H1 . . 125.7 ?
N1 C2 C3 . . 127.3(2) ?
N1 C2 C7 . . 109.4(2) ?
C3 C2 C7 . . 123.2(2) ?
C4 C3 C2 . . 115.5(2) ?
C4 C3 H3 . . 122.2 ?
C2 C3 H3 . . 122.2 ?
F1 C4 C3 . . 117.4(2) ?
F1 C4 C5 . . 118.3(2) ?
C3 C4 C5 . . 124.3(2) ?
C6 C5 C4 . . 119.2(2) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C7 . . 119.7(2) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C6 C7 C2 . . 118.0(2) ?
C6 C7 C8 . . 136.0(2) ?
C2 C7 C8 . . 105.9(2) ?
C13 C8 C9 . . 114.8(2) ?
C13 C8 C7 . . 105.3(2) ?
C9 C8 C7 . . 139.8(2) ?
N10 C9 N14 . . 116.1(2) ?
N10 C9 C8 . . 119.4(2) ?
N14 C9 C8 . . 124.5(2) ?
C11 N10 C9 . . 118.8(2) ?
N10 C11 N12 . . 127.7(2) ?
N10 C11 H11 . . 116.2 ?
N12 C11 H11 . . 116.2 ?
C11 N12 C13 . . 112.8(2) ?
N12 C13 N1 . . 123.2(2) ?
N12 C13 C8 . . 126.2(2) ?
N1 C13 C8 . . 110.6(2) ?
C9 N14 C15 . . 120.5(2) ?
C9 N14 C16 . . 117.9(2) ?
C15 N14 C16 . . 117.21(19) ?
N14 C15 H15A . . 109.5 ?
N14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N14 C16 C17 . . 111.8(2) ?
N14 C16 C21 . . 111.4(2) ?
C17 C16 C21 . . 110.5(2) ?
N14 C16 H16 . . 107.6 ?
C17 C16 H16 . . 107.6 ?
C21 C16 H16 . . 107.6 ?
C16 C17 C18 . . 109.4(2) ?
C16 C17 H17A . . 109.8 ?
C18 C17 H17A . . 109.8 ?
C16 C17 H17B . . 109.8 ?
C18 C17 H17B . . 109.8 ?
H17A C17 H17B . . 108.2 ?
C19 C18 C17 . . 110.9(2) ?
C19 C18 H18A . . 109.5 ?
C17 C18 H18A . . 109.5 ?
C19 C18 H18B . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 108.1 ?
N20 C19 C18 . . 110.8(2) ?
N20 C19 H19A . . 109.5 ?
C18 C19 H19A . . 109.5 ?
N20 C19 H19B . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 108.1 ?
C22 N20 C21 . . 124.2(2) ?
C22 N20 C19 . . 120.0(2) ?
C21 N20 C19 . . 112.5(2) ?
N20 C21 C16 . . 109.1(2) ?
N20 C21 H21A . . 109.9 ?
C16 C21 H21A . . 109.9 ?
N20 C21 H21B . . 109.9 ?
C16 C21 H21B . . 109.9 ?
H21A C21 H21B . . 108.3 ?
O23 C22 N20 . . 122.4(2) ?
O23 C22 C24 . . 120.7(2) ?
N20 C22 C24 . . 116.9(2) ?
C25 C24 C22 . . 113.5(2) ?
C25 C24 H24A . . 108.9 ?
C22 C24 H24A . . 108.9 ?
C25 C24 H24B . . 108.9 ?
C22 C24 H24B . . 108.9 ?
H24A C24 H24B . . 107.7 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C4 . 1.361(3) ?
N1 C13 . 1.359(3) ?
N1 C2 . 1.377(3) ?
N1 H1 . 0.8800 ?
C2 C3 . 1.392(3) ?
C2 C7 . 1.417(3) ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.389(4) ?
C5 C6 . 1.388(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.406(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.461(3) ?
C8 C13 . 1.411(3) ?
C8 C9 . 1.411(3) ?
C9 N10 . 1.358(3) ?
C9 N14 . 1.370(3) ?
N10 C11 . 1.330(3) ?
C11 N12 . 1.335(3) ?
C11 H11 . 0.9500 ?
N12 C13 . 1.343(3) ?
N14 C15 . 1.453(3) ?
N14 C16 . 1.474(3) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.526(3) ?
C16 C21 . 1.532(4) ?
C16 H16 . 1.0000 ?
C17 C18 . 1.540(4) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 C19 . 1.522(4) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 N20 . 1.469(3) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
N20 C22 . 1.360(3) ?
N20 C21 . 1.462(3) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 O23 . 1.227(3) ?
C22 C24 . 1.523(4) ?
C24 C25 . 1.508(4) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N12 5_566 0.88 1.99 2.849(3) 163.5 yes
C5 H5 O23 4_655 0.95 2.47 3.380(3) 161 yes
C11 H11 O23 3_456 0.95 2.54 3.482(3) 174 yes
C19 H19A O23 1_555 0.99 2.37 2.764(3) 103 yes
C19 H19A F1 4_645 0.99 2.49 3.246(3) 133 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 N1 C2 C3 . . . . 177.1(2) ?
C13 N1 C2 C7 . . . . -0.5(3) ?
N1 C2 C3 C4 . . . . -175.6(2) ?
C7 C2 C3 C4 . . . . 1.7(4) ?
C2 C3 C4 F1 . . . . -179.8(2) ?
C2 C3 C4 C5 . . . . 1.7(4) ?
F1 C4 C5 C6 . . . . 178.7(2) ?
C3 C4 C5 C6 . . . . -2.7(4) ?
C4 C5 C6 C7 . . . . 0.4(4) ?
C5 C6 C7 C2 . . . . 2.7(4) ?
C5 C6 C7 C8 . . . . 176.5(3) ?
N1 C2 C7 C6 . . . . 173.9(2) ?
C3 C2 C7 C6 . . . . -3.9(4) ?
N1 C2 C7 C8 . . . . -1.7(3) ?
C3 C2 C7 C8 . . . . -179.4(2) ?
C6 C7 C8 C13 . . . . -171.2(3) ?
C2 C7 C8 C13 . . . . 3.1(3) ?
C6 C7 C8 C9 . . . . 5.8(5) ?
C2 C7 C8 C9 . . . . -179.9(3) ?
C13 C8 C9 N10 . . . . 6.0(3) ?
C7 C8 C9 N10 . . . . -170.8(3) ?
C13 C8 C9 N14 . . . . -175.5(2) ?
C7 C8 C9 N14 . . . . 7.7(5) ?
N14 C9 N10 C11 . . . . 177.4(2) ?
C8 C9 N10 C11 . . . . -4.0(4) ?
C9 N10 C11 N12 . . . . -1.0(4) ?
N10 C11 N12 C13 . . . . 3.2(4) ?
C11 N12 C13 N1 . . . . 176.8(2) ?
C11 N12 C13 C8 . . . . -0.6(4) ?
C2 N1 C13 N12 . . . . -175.1(2) ?
C2 N1 C13 C8 . . . . 2.7(3) ?
C9 C8 C13 N12 . . . . -3.8(4) ?
C7 C8 C13 N12 . . . . 174.0(2) ?
C9 C8 C13 N1 . . . . 178.6(2) ?
C7 C8 C13 N1 . . . . -3.6(3) ?
N10 C9 N14 C15 . . . . -146.1(2) ?
C8 C9 N14 C15 . . . . 35.4(3) ?
N10 C9 N14 C16 . . . . 9.8(3) ?
C8 C9 N14 C16 . . . . -168.7(2) ?
C9 N14 C16 C17 . . . . 154.3(2) ?
C15 N14 C16 C17 . . . . -49.0(3) ?
C9 N14 C16 C21 . . . . -81.5(3) ?
C15 N14 C16 C21 . . . . 75.2(3) ?
N14 C16 C17 C18 . . . . -179.1(2) ?
C21 C16 C17 C18 . . . . 56.2(3) ?
C16 C17 C18 C19 . . . . -54.0(3) ?
C17 C18 C19 N20 . . . . 54.8(3) ?
C18 C19 N20 C22 . . . . 101.4(3) ?
C18 C19 N20 C21 . . . . -58.9(3) ?
C22 N20 C21 C16 . . . . -98.9(3) ?
C19 N20 C21 C16 . . . . 60.4(3) ?
N14 C16 C21 N20 . . . . 176.0(2) ?
C17 C16 C21 N20 . . . . -59.1(3) ?
C21 N20 C22 O23 . . . . 164.3(2) ?
C19 N20 C22 O23 . . . . 6.4(4) ?
C21 N20 C22 C24 . . . . -18.4(4) ?
C19 N20 C22 C24 . . . . -176.4(2) ?
O23 C22 C24 C25 . . . . 11.8(4) ?
N20 C22 C24 C25 . . . . -165.5(3) ?

_cod_database_fobs_code 1560706
