#------------------------------------------------------------------------------
#$Date: 2021-02-24 07:31:42 +0200 (Wed, 24 Feb 2021) $
#$Revision: 262184 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/23/7242301.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_7242301
loop_
_publ_author_name
'Sebghati, Marjan'
'Tarahhomi, Atekeh'
'Bozorgvar, Marjan Sadat'
'Dumitrescu, Dan G.'
'van der Lee, Arie'
_publ_section_title
;
 Coordination versus hydrogen bonds in the structures of different
 tris(pyridin-2-yl)phosphoric triamide derivatives
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              8178
_journal_page_last               8197
_journal_paper_doi               10.1039/D0RA10539B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         '0.5(C6 H6 Cu2 O12), C2 H8 N'
_chemical_formula_sum            'C5 H11 Cu N O6'
_chemical_formula_weight         244.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-26 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.746(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5393(16)
_cell_length_b                   8.6391(6)
_cell_length_c                   8.8358(9)
_cell_measurement_reflns_used    1136
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1900
_cell_measurement_theta_min      2.7160
_cell_volume                     876.41(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.793
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00 180.00   0.50    0.13    --    0.00   0.00   0.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'rotating crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3048
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         31.758
_diffrn_reflns_theta_min         2.906
_diffrn_source                   SCW
_exptl_absorpt_coefficient_mu    2.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            light_blue
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.371
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.246
_refine_ls_extinction_coef       0.005(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0734
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1996P)²+0.0925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2243
_refine_ls_wR_factor_ref         0.2824
_reflns_Friedel_coverage         0.000
_reflns_number_gt                951
_reflns_number_total             1239
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL mb1k_c3__twin1_a.res in I2/a
    mb1k_c3__twin1.res
    created by SHELXL-2018/3 at 15:55:45 on 24-Jul-2019
REM Old TITL MB1K_c3__twin1 in I2/a
REM SHELXT solution in I2/a
REM R1 0.467, Rweak 0.491, Alpha 0.016, Orientation as input
REM Formula found by SHELXT: C5 N O6 Cu
CELL 0.7 11.5393 8.6391 8.8358 90 95.746 90
ZERR 4 0.0016 0.0006 0.0009 0 0.011 0
LATT 2
SYMM 0.5-X,+Y,-Z
SFAC C H Cu N O
DISP C 0.0033 0.0016 11.1819
DISP Cu 0.345 1.2548 4976.3916
DISP H -0 0 0.6234
DISP N 0.0063 0.0031 18.9823
DISP O 0.0112 0.0059 31.3712
UNIT 20 44 4 4 24

L.S. 4
PLAN  20
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\MB1K_c3__twin1.hkl">
REM </olex2.extras>

WGHT    0.199600    0.092500
EXTI    0.000000
FVAR       0.62904
CU01  3    0.500000    0.500000    0.000000    10.50000    0.06920    0.01101 =
         0.02583    0.00282    0.00083   -0.00308
O002  5    0.346296    0.393807    0.007444    11.00000    0.07759    0.01068 =
         0.02929   -0.00029    0.00552   -0.00102
O003  5    0.571741    0.232033    0.379736    11.00000    0.06856    0.01466 =
         0.03431   -0.00147    0.00219    0.00357
O004  5    0.560003    0.413502    0.202019    11.00000    0.06845    0.01867 =
         0.03392   -0.00132    0.00288   -0.00379
N005  4    0.750000    0.433140    0.500000    10.50000    0.07222    0.01189 =
         0.03283    0.00000   -0.00949    0.00000
AFIX  23
H00A  2    0.696278    0.372463    0.451104    10.50000   -1.20000
H00B  2    0.803723    0.372463    0.548896    10.50000   -1.20000
AFIX   0
C006  1    0.527904    0.287116    0.258786    11.00000    0.06392    0.01371 =
         0.03736   -0.00470   -0.00103   -0.00123
AFIX  43
H006  2    0.467358    0.232755    0.205441    11.00000   -1.20000
AFIX   0
C007  1    0.695466    0.527147    0.611011    11.00000    0.06439    0.02266 =
         0.03030    0.00208    0.01806   -0.00120
AFIX 137
H00C  2    0.637721    0.593328    0.558880    11.00000   -1.50000
H00D  2    0.753704    0.589199    0.667583    11.00000   -1.50000
H00E  2    0.659195    0.460586    0.679398    11.00000   -1.50000
AFIX   0
C008  1    0.250000    0.462504    0.000000    10.50000    0.07604    0.01103 =
         0.02818    0.00000   -0.00055    0.00000
AFIX  43
H008  2    0.250001    0.570154   -0.000001    10.50000   -1.20000
AFIX   0
HKLF 4




REM  mb1k_c3__twin1_a.res in I2/a
REM wR2 = 0.2824, GooF = S = 1.171, Restrained GooF = 1.171 for all data
REM R1 = 0.0734 for 951 Fo > 4sig(Fo) and 0.0931 for all 1239 data
REM 64 parameters refined using 0 restraints

END  
     
WGHT      0.1993      0.1129 

REM Highest difference peak  1.371,  deepest hole -1.028,  1-sigma level  0.246
Q1    1   0.5669  0.5631 -0.0204  11.00000  0.05    1.37
Q2    1   0.4363  0.5616  0.0211  11.00000  0.05    1.34
Q3    1   0.6394  0.2914  0.3510  11.00000  0.05    0.80
Q4    1   0.7636  0.5041  0.5830  11.00000  0.05    0.77
Q5    1   0.6119  0.3674  0.1808  11.00000  0.05    0.77
Q6    1   0.6609  0.2038  0.3762  11.00000  0.05    0.74
Q7    1   0.5241  0.2706  0.4261  11.00000  0.05    0.73
Q8    1   0.5758  0.5039  0.8092  11.00000  0.05    0.72
Q9    1   0.5489  0.4558  0.0961  11.00000  0.05    0.69
Q10   1   0.6484  0.4943  0.1696  11.00000  0.05    0.69
Q11   1   0.5834  0.5055  0.1080  11.00000  0.05    0.68
Q12   1   0.6091  0.2008  0.3164  11.00000  0.05    0.67
Q13   1   0.6045  0.4846  0.3184  11.00000  0.05    0.66
Q14   1   0.6475  0.5380  0.6391  11.00000  0.05    0.63
Q15   1   0.8497  0.4559  0.6569  11.00000  0.05    0.62
Q16   1   0.5360  0.5680  0.0886  11.00000  0.05    0.61
Q17   1   0.5395  0.5012  0.4608  11.00000  0.05    0.60
Q18   1   0.4345  0.2253  0.2033  11.00000  0.05    0.60
Q19   1   0.4897  0.4728  0.2585  11.00000  0.05    0.58
Q20   1   0.3718  0.2003  0.1578  11.00000  0.05    0.58

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0734 for 951 Fo > 4sig(Fo) and 0.0931 for all 3147 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 1.37, deepest hole -1.03
  REM Mean Shift 0.001, Max Shift -0.033.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0931
  REM R1_gt = 0.0734
  REM wR_ref = 0.2824
  REM GOOF = 1.171
  REM Shift_max = -0.033
  REM Shift_mean = 0.001
  REM Reflections_all = 3147
  REM Reflections_gt = 951
  REM Parameters = n/a
  REM Hole = -1.03
  REM Peak = 1.37
  REM Flack = n/a

  
;
_cod_data_source_file            d0ra10539b2.cif
_cod_data_source_block           mb1k_c3__twin1
_cod_database_code               7242301
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H00A(0.5) H00B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 N005(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008)
3.c Idealised Me refined as rotating group:
 C007(H00C,H00D,H00E)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu01 Cu 0.500000 0.500000 0.000000 0.0356(5) Uani 1 2 d S T P . .
O002 O 0.3463(3) 0.3938(3) 0.0074(4) 0.0392(8) Uani 1 1 d . . . . .
O003 O 0.5717(3) 0.2320(3) 0.3797(4) 0.0394(8) Uani 1 1 d . . . . .
O004 O 0.5600(3) 0.4135(4) 0.2020(4) 0.0405(8) Uani 1 1 d . . . . .
N005 N 0.750000 0.4331(6) 0.500000 0.0400(13) Uani 1 2 d S T P . .
H00A H 0.696278 0.372463 0.451104 0.048 Uiso 0.5 1 calc R . . . .
H00B H 0.803723 0.372463 0.548896 0.048 Uiso 0.5 1 calc R . . . .
C006 C 0.5279(4) 0.2871(5) 0.2588(5) 0.0387(10) Uani 1 1 d . . . . .
H006 H 0.467358 0.232755 0.205441 0.046 Uiso 1 1 calc R . . . .
C007 C 0.6955(5) 0.5271(6) 0.6110(7) 0.0382(11) Uani 1 1 d . . . . .
H00C H 0.637721 0.593328 0.558880 0.057 Uiso 1 1 calc GR . . . .
H00D H 0.753704 0.589199 0.667583 0.057 Uiso 1 1 calc GR . . . .
H00E H 0.659195 0.460586 0.679398 0.057 Uiso 1 1 calc GR . . . .
C008 C 0.250000 0.4625(8) 0.000000 0.0388(14) Uani 1 2 d S T P . .
H008 H 0.250001 0.570154 -0.000001 0.047 Uiso 1 2 calc RS T P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu01 0.0692(8) 0.0110(6) 0.0258(6) 0.00282(19) 0.0008(4) -0.0031(2)
O002 0.078(2) 0.0107(14) 0.0293(15) -0.0003(10) 0.0055(14) -0.0010(12)
O003 0.069(2) 0.0147(13) 0.0343(15) -0.0015(12) 0.0022(13) 0.0036(12)
O004 0.068(2) 0.0187(14) 0.0339(16) -0.0013(12) 0.0029(14) -0.0038(13)
N005 0.072(4) 0.012(2) 0.033(3) 0.000 -0.009(2) 0.000
C006 0.064(3) 0.0137(17) 0.037(2) -0.0047(15) -0.0010(19) -0.0012(16)
C007 0.064(3) 0.0227(17) 0.030(2) 0.0021(19) 0.0181(19) -0.0012(19)
C008 0.076(4) 0.011(2) 0.028(3) 0.000 -0.001(2) 0.000
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'
Cu Cu 0.3450 1.2548 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0063 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0112 0.0059 '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
_geom_angle_publ_flag
O002 Cu01 O002 180.0 5_665 . ?
O004 Cu01 O002 91.62(13) 5_665 5_665 ?
O004 Cu01 O002 91.62(13) . . ?
O004 Cu01 O002 88.38(13) . 5_665 ?
O004 Cu01 O002 88.38(13) 5_665 . ?
O004 Cu01 O004 180.0 5_665 . ?
C008 O002 Cu01 124.3(3) . . ?
C006 O004 Cu01 125.9(3) . . ?
H00A N005 H00B 107.8 . . ?
C007 N005 H00A 109.1 . . ?
C007 N005 H00A 109.1 2_656 . ?
C007 N005 H00B 109.1 . . ?
C007 N005 H00B 109.1 2_656 . ?
C007 N005 C007 112.6(5) . 2_656 ?
O003 C006 O004 124.3(4) . . ?
O003 C006 H006 117.9 . . ?
O004 C006 H006 117.9 . . ?
N005 C007 H00C 109.5 . . ?
N005 C007 H00D 109.5 . . ?
N005 C007 H00E 109.5 . . ?
H00C C007 H00D 109.5 . . ?
H00C C007 H00E 109.5 . . ?
H00D C007 H00E 109.5 . . ?
O002 C008 O002 123.6(6) 2 . ?
O002 C008 H008 118.2 2 . ?
O002 C008 H008 118.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu01 O002 2.004(4) 5_665 ?
Cu01 O002 2.004(4) . ?
Cu01 O004 1.994(3) 5_665 ?
Cu01 O004 1.994(3) . ?
O002 C008 1.256(5) . ?
O003 C006 1.231(6) . ?
O004 C006 1.272(5) . ?
N005 H00A 0.8900 . ?
N005 H00B 0.8900 . ?
N005 C007 1.463(6) . ?
N005 C007 1.463(6) 2_656 ?
C006 H006 0.9300 . ?
C007 H00C 0.9600 . ?
C007 H00D 0.9600 . ?
C007 H00E 0.9600 . ?
C008 H008 0.9300 . ?
