#------------------------------------------------------------------------------
#$Date: 2019-11-22 23:25:48 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231558 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/33/4003384.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_4003384
loop_
_publ_author_name
'Xiong, Lin'
'Chen, Jie'
'Lu, Jing'
'Pan, Chun-Ya'
'Wu, Li-Ming'
_publ_section_title
;
 Monofluorophosphates: A New Source of Deep-Ultraviolet Nonlinear Optical
 Materials
;
_journal_issue                   21
_journal_name_full               'Chemistry of Materials'
_journal_page_first              7823
_journal_paper_doi               10.1021/acs.chemmater.8b03310
_journal_volume                  30
_journal_year                    2018
_chemical_formula_sum            'C2 H12 F N6 O3 P'
_chemical_formula_weight         218.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 119.710(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2025(14)
_cell_length_b                   7.2951(7)
_cell_length_c                   11.7574(12)
_cell_measurement_reflns_used    4935
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.09
_cell_volume                     983.54(18)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'BRUKER D8 QUEST PHOTON II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12500
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         3.095
_exptl_absorpt_coefficient_mu    0.288
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 861 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2406
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0465
_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)+(0.0363P)²+0.6886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.984
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2129
_reflns_number_total             2406
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm8b03310_si_003.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'C m'
_cod_database_code               4003384
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
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
_atom_site_refinement_flags_occupancy
P1 P 0.29602(12) 0.000000 0.36846(14) 0.0315(4) Uani 1 2 d S T P
P2 P 0.77017(11) 0.000000 0.79761(13) 0.0284(4) Uani 1 2 d S T P
N1 N 0.5296(5) 0.3432(5) 0.5816(5) 0.0468(9) Uani 1 1 d . . .
N2 N 0.3706(5) 0.500000 0.4294(6) 0.0451(14) Uani 1 2 d S T P
N3 N 0.3512(5) 0.000000 0.8203(6) 0.0411(14) Uani 1 2 d S T P
N4 N 0.5038(4) 0.1567(6) 0.8242(5) 0.0425(9) Uani 1 1 d . . .
N5 N 0.3417(4) 0.2424(9) 0.1140(7) 0.0563(12) Uani 1 1 d . . .
N6 N 0.5078(4) 0.2833(7) 0.1041(4) 0.0518(12) Uani 1 1 d D . .
H3 H 0.466(5) 0.310(9) 0.022(3) 0.062 Uiso 1 1 d D U .
N7 N 0.5187(6) 0.2242(8) 0.2994(5) 0.0530(12) Uani 1 1 d . . .
F1 F 0.2538(4) 0.000000 0.4715(4) 0.0657(13) Uani 1 2 d S T P
F2 F 0.9001(4) 0.000000 0.8525(4) 0.0563(11) Uani 1 2 d S T P
O1 O 0.2471(3) 0.1736(4) 0.2919(3) 0.0465(9) Uani 1 1 d . . .
O2 O 0.4265(4) 0.000000 0.4463(5) 0.0440(11) Uani 1 2 d S T P
O3 O 0.7252(3) 0.1738(4) 0.8263(3) 0.0393(8) Uani 1 1 d . . .
O4 O 0.7156(4) 0.000000 0.6449(4) 0.0377(10) Uani 1 2 d S T P
C1 C 0.4763(6) 0.500000 0.5318(6) 0.0370(14) Uani 1 2 d S T P
C2 C 0.4522(5) 0.000000 0.8216(6) 0.0345(13) Uani 1 2 d S T P
C3 C 0.4553(4) 0.2505(6) 0.1720(5) 0.0402(10) Uani 1 1 d . . .
H1 H 0.314(5) 0.231(8) 0.154(6) 0.05(2) Uiso 1 1 d . . .
H2 H 0.306(5) 0.256(8) 0.042(6) 0.041(18) Uiso 1 1 d . . .
H4 H 0.574(6) 0.304(9) 0.139(6) 0.064(19) Uiso 1 1 d . . .
H5 H 0.582(6) 0.217(8) 0.334(6) 0.041(18) Uiso 1 1 d . . .
H6 H 0.494(5) 0.180(8) 0.342(6) 0.048(18) Uiso 1 1 d . . .
H7 H 0.333(4) 0.391(7) 0.400(5) 0.048(14) Uiso 1 1 d . . .
H8 H 0.495(6) 0.250(9) 0.550(7) 0.06(2) Uiso 1 1 d . . .
H9 H 0.595(5) 0.337(7) 0.644(5) 0.045(16) Uiso 1 1 d . . .
H10 H 0.560(5) 0.148(8) 0.812(6) 0.050(16) Uiso 1 1 d . . .
H11 H 0.473(5) 0.271(8) 0.830(6) 0.057(16) Uiso 1 1 d . . .
H12 H 0.329(4) 0.093(6) 0.826(4) 0.027(12) Uiso 1 1 d . . .
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'
P P 0.1023 0.0942 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 P1 O1 112.87(16) . .
O2 P1 O1 112.87(16) . 2
O1 P1 O1 115.0(3) . 2
O2 P1 F1 105.7(3) . .
O1 P1 F1 104.61(18) . .
O1 P1 F1 104.61(18) 2 .
F2 P2 O3 113.32(15) . .
F2 P2 O3 113.32(15) . 2
O3 P2 O3 114.5(2) . 2
F2 P2 O4 105.7(3) . .
O3 P2 O4 104.35(17) . .
O3 P2 O4 104.35(17) 2 .
N2 C1 N1 119.8(3) . 2_565
N2 C1 N1 119.8(3) . .
N1 C1 N1 120.3(6) 2_565 .
N4 C2 N4 119.5(6) . 2
N4 C2 N3 120.2(3) . .
N4 C2 N3 120.2(3) 2 .
N5 C3 N6 120.5(5) . .
N5 C3 N7 120.3(6) . .
N6 C3 N7 119.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.498(5) .
P1 O1 1.502(3) .
P1 O1 1.502(3) 2
P1 F1 1.565(4) .
P2 F2 1.504(4) .
P2 O3 1.507(3) .
P2 O3 1.507(3) 2
P2 O4 1.568(4) .
N1 C1 1.319(5) .
N2 C1 1.316(9) .
N3 C2 1.326(8) .
N4 C2 1.323(5) .
N5 C3 1.305(6) .
N6 C3 1.312(6) .
N7 C3 1.319(7) .
