#------------------------------------------------------------------------------
#$Date: 2019-11-17 11:45:56 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229681 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/80/7048022.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7048022
loop_
_publ_author_name
'Takeshita, Tomohiro'
'Sato, Kazuhiko'
'Nakajima, Yumiko'
_publ_section_title
;
 Selective hydrosiloxane synthesis via dehydrogenative coupling of
 silanols with hydrosilanes catalysed by Fe complexes bearing a
 tetradentate PNNP ligand.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17004
_journal_page_last               17010
_journal_paper_doi               10.1039/c8dt04168g
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C19 H12 Cl N O'
_chemical_formula_sum            'C19 H12 Cl N O'
_chemical_formula_weight         305.75
_chemical_name_systematic        5-(4-Chlorophenyl)-phenanthredin-6-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-09-10 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.941(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4622(2)
_cell_length_b                   25.5595(11)
_cell_length_c                   10.5965(5)
_cell_measurement_reflns_used    7084
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.12
_cell_volume                     1447.38(11)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      ' 138 frames, detector distance = 80 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7429
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.436
_diffrn_reflns_theta_min         2.120
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.8976
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          1.070
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0579
_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/[σ²(Fo²)+(0.0331P)²+1.4963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2699
_reflns_number_total             3631
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt04168g2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7048021--7048028.cif.'
_cod_database_code               7048022
_shelx_shelxl_version_number     2018/1
_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   0.765
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.04103(14) 0.06584(2) 0.62094(7) 0.0510(2) Uani 1 1 d . .
N1 N 0.0931(3) 0.29729(7) 0.63660(17) 0.0270(4) Uani 1 1 d . .
C2 C -0.0987(4) 0.32911(8) 0.5654(2) 0.0269(4) Uani 1 1 d . .
C3 C -0.3020(4) 0.30599(9) 0.4830(2) 0.0306(5) Uani 1 1 d . .
H3 H -0.307958 0.269071 0.472394 0.037 Uiso 1 1 calc R U
C4 C -0.4946(4) 0.33660(10) 0.4166(2) 0.0358(5) Uani 1 1 d . .
H4 H -0.633320 0.320615 0.361096 0.043 Uiso 1 1 calc R U
C5 C -0.4866(5) 0.39067(10) 0.4308(2) 0.0369(5) Uani 1 1 d . .
H5 H -0.620639 0.411653 0.386335 0.044 Uiso 1 1 calc R U
C6 C -0.2829(4) 0.41356(9) 0.5096(2) 0.0360(5) Uani 1 1 d . .
H6 H -0.276981 0.450588 0.517421 0.043 Uiso 1 1 calc R U
C7 C -0.0842(4) 0.38391(8) 0.5786(2) 0.0284(4) Uani 1 1 d . .
C8 C 0.1349(4) 0.40694(8) 0.6624(2) 0.0303(5) Uani 1 1 d . .
C9 C 0.1695(5) 0.46111(9) 0.6798(3) 0.0403(6) Uani 1 1 d . .
H9 H 0.043291 0.484399 0.637525 0.048 Uiso 1 1 calc R U
C10 C 0.3831(5) 0.48106(10) 0.7572(3) 0.0462(6) Uani 1 1 d . .
H10 H 0.402926 0.517861 0.766887 0.055 Uiso 1 1 calc R U
C11 C 0.5705(5) 0.44779(10) 0.8213(3) 0.0443(6) Uani 1 1 d . .
H11 H 0.717556 0.461817 0.874328 0.053 Uiso 1 1 calc R U
C12 C 0.5409(5) 0.39469(10) 0.8074(2) 0.0371(5) Uani 1 1 d . .
H12 H 0.667719 0.371838 0.851120 0.044 Uiso 1 1 calc R U
C13 C 0.3242(4) 0.37403(8) 0.7289(2) 0.0289(5) Uani 1 1 d . .
C14 C 0.3020(4) 0.31686(9) 0.7200(2) 0.0287(4) Uani 1 1 d . .
O15 O 0.4572(3) 0.28704(6) 0.78323(16) 0.0367(4) Uani 1 1 d . .
C16 C 0.0709(4) 0.24101(8) 0.6278(2) 0.0277(4) Uani 1 1 d . .
C17 C -0.0866(4) 0.21531(9) 0.6944(2) 0.0317(5) Uani 1 1 d . .
H17 H -0.184366 0.234551 0.742698 0.038 Uiso 1 1 calc R U
C18 C -0.0997(4) 0.16100(9) 0.6895(2) 0.0353(5) Uani 1 1 d . .
H18 H -0.208501 0.142726 0.733446 0.042 Uiso 1 1 calc R U
C19 C 0.0470(4) 0.13391(8) 0.6201(2) 0.0332(5) Uani 1 1 d . .
C20 C 0.2005(5) 0.15947(10) 0.5523(2) 0.0384(6) Uani 1 1 d . .
H20 H 0.297996 0.140225 0.503862 0.046 Uiso 1 1 calc R U
C21 C 0.2109(4) 0.21354(9) 0.5557(2) 0.0352(5) Uani 1 1 d . .
H21 H 0.314336 0.231726 0.508413 0.042 Uiso 1 1 calc R U
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.5360
1 0 -1 0.5360
0 1 0 0.0245
0 -1 0 0.0245
1 0 6 0.0730
-1 0 -6 0.0730
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C14 N1 C2 123.68(18)
C14 N1 C16 116.65(18)
C2 N1 C16 119.63(18)
C3 C2 C7 120.4(2)
C3 C2 N1 119.77(19)
C7 C2 N1 119.88(19)
C4 C3 C2 120.2(2)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 120.3(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 119.4(2)
C6 C5 H5 120.3
C4 C5 H5 120.3
C5 C6 C7 122.0(2)
C5 C6 H6 119.0
C7 C6 H6 119.0
C6 C7 C2 117.7(2)
C6 C7 C8 123.3(2)
C2 C7 C8 119.0(2)
C9 C8 C13 117.3(2)
C9 C8 C7 123.3(2)
C13 C8 C7 119.3(2)
C10 C9 C8 121.2(2)
C10 C9 H9 119.4
C8 C9 H9 119.4
C9 C10 C11 120.7(2)
C9 C10 H10 119.7
C11 C10 H10 119.7
C12 C11 C10 119.5(2)
C12 C11 H11 120.2
C10 C11 H11 120.2
C11 C12 C13 120.2(2)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C8 121.1(2)
C12 C13 C14 117.5(2)
C8 C13 C14 121.4(2)
O15 C14 N1 120.5(2)
O15 C14 C13 122.9(2)
N1 C14 C13 116.59(19)
C21 C16 C17 121.0(2)
C21 C16 N1 119.6(2)
C17 C16 N1 119.4(2)
C16 C17 C18 119.1(2)
C16 C17 H17 120.4
C18 C17 H17 120.4
C19 C18 C17 119.3(2)
C19 C18 H18 120.4
C17 C18 H18 120.4
C20 C19 C18 121.5(2)
C20 C19 Cl1 119.42(19)
C18 C19 Cl1 119.03(19)
C19 C20 C21 119.2(2)
C19 C20 H20 120.4
C21 C20 H20 120.4
C16 C21 C20 119.9(2)
C16 C21 H21 120.1
C20 C21 H21 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C19 1.740(2)
N1 C14 1.384(3)
N1 C2 1.415(3)
N1 C16 1.445(3)
C2 C3 1.394(3)
C2 C7 1.408(3)
C3 C4 1.381(3)
C3 H3 0.9500
C4 C5 1.390(3)
C4 H4 0.9500
C5 C6 1.376(3)
C5 H5 0.9500
C6 C7 1.400(3)
C6 H6 0.9500
C7 C8 1.458(3)
C8 C9 1.404(3)
C8 C13 1.405(3)
C9 C10 1.377(4)
C9 H9 0.9500
C10 C11 1.395(4)
C10 H10 0.9500
C11 C12 1.371(3)
C11 H11 0.9500
C12 C13 1.402(3)
C12 H12 0.9500
C13 C14 1.467(3)
C14 O15 1.231(3)
C16 C21 1.380(3)
C16 C17 1.386(3)
C17 C18 1.390(3)
C17 H17 0.9500
C18 C19 1.381(3)
C18 H18 0.9500
C19 C20 1.377(4)
C20 C21 1.383(3)
C20 H20 0.9500
C21 H21 0.9500
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
C14 N1 C2 C3 179.6(2)
C16 N1 C2 C3 -2.9(3)
C14 N1 C2 C7 -0.7(3)
C16 N1 C2 C7 176.8(2)
C7 C2 C3 C4 -2.0(3)
N1 C2 C3 C4 177.6(2)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 1.2(4)
C4 C5 C6 C7 -1.3(4)
C5 C6 C7 C2 -0.2(3)
C5 C6 C7 C8 179.6(2)
C3 C2 C7 C6 1.9(3)
N1 C2 C7 C6 -177.8(2)
C3 C2 C7 C8 -178.0(2)
N1 C2 C7 C8 2.3(3)
C6 C7 C8 C9 -1.2(4)
C2 C7 C8 C9 178.6(2)
C6 C7 C8 C13 179.4(2)
C2 C7 C8 C13 -0.8(3)
C13 C8 C9 C10 1.3(4)
C7 C8 C9 C10 -178.1(2)
C8 C9 C10 C11 -0.6(4)
C9 C10 C11 C12 -0.2(4)
C10 C11 C12 C13 0.2(4)
C11 C12 C13 C8 0.6(4)
C11 C12 C13 C14 -178.9(2)
C9 C8 C13 C12 -1.3(3)
C7 C8 C13 C12 178.2(2)
C9 C8 C13 C14 178.2(2)
C7 C8 C13 C14 -2.4(3)
C2 N1 C14 O15 176.9(2)
C16 N1 C14 O15 -0.6(3)
C2 N1 C14 C13 -2.4(3)
C16 N1 C14 C13 -179.94(18)
C12 C13 C14 O15 4.1(3)
C8 C13 C14 O15 -175.4(2)
C12 C13 C14 N1 -176.6(2)
C8 C13 C14 N1 3.9(3)
C14 N1 C16 C21 -77.9(3)
C2 N1 C16 C21 104.4(2)
C14 N1 C16 C17 100.5(2)
C2 N1 C16 C17 -77.1(3)
C21 C16 C17 C18 1.0(4)
N1 C16 C17 C18 -177.5(2)
C16 C17 C18 C19 0.9(4)
C17 C18 C19 C20 -2.0(4)
C17 C18 C19 Cl1 176.87(19)
C18 C19 C20 C21 1.1(4)
Cl1 C19 C20 C21 -177.8(2)
C17 C16 C21 C20 -1.9(4)
N1 C16 C21 C20 176.6(2)
C19 C20 C21 C16 0.8(4)
