#------------------------------------------------------------------------------
#$Date: 2019-11-19 10:44:48 +0200 (Tue, 19 Nov 2019) $
#$Revision: 231036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/51/7235187.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_7235187
loop_
_publ_author_name
'Fu-Juan Geng'
'Lin Zhou'
'Ping-Ping Shi'
'Xiao-Li Wang'
'Xuan Zheng'
'Yi Zhang'
'Da-Wei Fu'
'Qiong Ye'
_publ_section_title
;
 Perovskite-type organic-inorganic hybrid NLO switches tuned by guest
 cations
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1529
_journal_page_last               1536
_journal_paper_doi               10.1039/C6TC05105G
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C6 Mn N9,C8 H20 O P'
_chemical_formula_sum            'C14 H20 Mn N9 O P'
_chemical_formula_weight         416.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.694(2)
_cell_length_b                   12.092(2)
_cell_length_c                   16.108(3)
_cell_measurement_reflns_used    2752
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7893
_cell_measurement_theta_min      2.2052
_cell_volume                     2083.0(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14569
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.039
_exptl_absorpt_coefficient_mu    0.732
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       Prism
_exptl_crystal_F_000             860
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4760
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0601
_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)+(0.0758P)²+0.0779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1537
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3164
_reflns_number_total             4760
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2017-5-1529.cif
_cod_data_source_block           4
_cod_original_cell_volume        2083.0(7)
_cod_database_code               7235187
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.5287(10) 0.5149(8) 0.9347(7) 0.101(3) Uani 1 1 d . . . . .
H8A H 0.5233 0.4768 0.8819 0.122 Uiso 1 1 calc R U . . .
H8B H 0.4798 0.4735 0.9748 0.122 Uiso 1 1 calc R U . . .
C5 C 0.8215(11) 0.5891(13) 1.1042(8) 0.146(5) Uani 1 1 d . . . . .
H5A H 0.8485 0.5168 1.1209 0.219 Uiso 1 1 calc R U . . .
H5B H 0.8200 0.6372 1.1516 0.219 Uiso 1 1 calc R U . . .
H5C H 0.8782 0.6181 1.0634 0.219 Uiso 1 1 calc R U . . .
C4 C 0.6952(10) 0.5820(8) 1.0683(6) 0.097(3) Uani 1 1 d . . . . .
H4A H 0.6609 0.6559 1.0638 0.116 Uiso 1 1 calc R U . . .
H4B H 0.6422 0.5403 1.1059 0.116 Uiso 1 1 calc R U . . .
C6 C 0.7843(9) 0.5942(7) 0.8949(6) 0.085(2) Uani 1 1 d . . . . .
H6A H 0.7546 0.6699 0.8931 0.102 Uiso 1 1 calc R U . . .
H6B H 0.8702 0.5956 0.9143 0.102 Uiso 1 1 calc R U . . .
C1 C 0.7492(14) 0.3784(7) 0.9737(7) 0.118(4) Uani 1 1 d . . . . .
H1A H 0.7382 0.3417 0.9206 0.141 Uiso 1 1 calc R U . . .
H1B H 0.8376 0.3786 0.9872 0.141 Uiso 1 1 calc R U . . .
P1 P 0.69110(19) 0.51792(16) 0.96824(14) 0.0688(6) Uani 1 1 d . . . . .
C10 C 0.1670(7) 0.6079(6) 0.0113(4) 0.0576(17) Uani 1 1 d . U . . .
C14 C 0.4171(7) 0.3400(6) 0.1610(4) 0.0596(19) Uani 1 1 d . . . . .
N4 N 0.1238(6) 0.4279(5) 0.1871(5) 0.0832(19) Uani 1 1 d . . . . .
N7 N 0.4027(6) 0.4268(5) 0.1349(4) 0.0638(16) Uani 1 1 d . . . . .
N1 N 0.2147(7) 0.6173(5) 0.0730(3) 0.0646(15) Uani 1 1 d . . . . .
Mn1 Mn 0.27545(9) 0.55427(7) 0.19451(5) 0.0412(3) Uani 1 1 d . . . . .
N8 N 0.4213(7) 0.2378(5) 0.1864(6) 0.089(2) Uani 1 1 d . . . . .
N2 N 0.1014(7) 0.6073(8) -0.0565(4) 0.093(2) Uani 1 1 d . U . . .
N5 N 0.0019(11) 0.2668(9) 0.1592(7) 0.146(3) Uani 1 1 d . U . . .
C9 C 0.4731(10) 0.6300(10) 0.9255(8) 0.118(4) Uani 1 1 d . . . . .
H9A H 0.4623 0.6625 0.9794 0.178 Uiso 1 1 calc R U . . .
H9B H 0.3935 0.6250 0.8983 0.178 Uiso 1 1 calc R U . . .
H9C H 0.5284 0.6752 0.8931 0.178 Uiso 1 1 calc R U . . .
C12 C 0.0641(10) 0.3548(8) 0.1796(6) 0.097(3) Uani 1 1 d . U . . .
C7 C 0.7819(10) 0.5475(7) 0.8085(6) 0.106(3) Uani 1 1 d . . . . .
H7A H 0.8087 0.4718 0.8098 0.158 Uiso 1 1 calc R U . . .
H7B H 0.8372 0.5894 0.7737 0.158 Uiso 1 1 calc R U . . .
H7C H 0.6984 0.5516 0.7869 0.158 Uiso 1 1 calc R U . . .
O1 O 0.6828(10) 0.3243(6) 1.0343(5) 0.149(4) Uani 1 1 d . . . . .
C3 C 0.7038(16) 0.2128(8) 1.0361(8) 0.148(6) Uani 1 1 d . . . . .
H3A H 0.6324 0.1748 1.0140 0.223 Uiso 1 1 calc R U . . .
H3B H 0.7176 0.1897 1.0924 0.223 Uiso 1 1 calc R U . . .
H3C H 0.7762 0.1957 1.0033 0.223 Uiso 1 1 calc R U . . .
C13 C -0.0785(10) 0.2186(8) 0.2098(6) 0.100(3) Uani 1 1 d . U . . .
N6 N -0.1484(7) 0.1706(6) 0.2434(4) 0.0775(19) Uani 1 1 d . . . . .
N3 N 0.1684(6) 0.5176(5) -0.1839(4) 0.0731(17) Uani 1 1 d . . . . .
C11 C 0.1424(7) 0.5575(7) -0.1232(4) 0.0642(18) Uani 1 1 d . U . . .
N9 N 0.5652(6) 0.1700(5) 0.2931(5) 0.0703(18) Uani 1 1 d . . . . .
C15 C 0.5013(8) 0.2067(5) 0.2421(6) 0.0640(19) Uani 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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
C9 C8 P1 112.6(6) . .
C5 C4 P1 113.7(9) . .
C7 C6 P1 114.0(6) . .
O1 C1 P1 107.6(8) . .
C4 P1 C1 110.7(5) . .
C4 P1 C6 110.9(5) . .
C1 P1 C6 108.7(5) . .
C4 P1 C8 107.4(5) . .
C1 P1 C8 109.0(6) . .
C6 P1 C8 110.1(5) . .
N1 C10 N2 172.1(8) . .
N7 C14 N8 173.3(8) . .
C12 N4 Mn1 168.7(8) . .
C14 N7 Mn1 123.3(6) . .
C10 N1 Mn1 152.5(6) . .
N6 Mn1 N1 90.0(3) 3 .
N6 Mn1 N9 91.7(3) 3 3_655
N1 Mn1 N9 95.1(3) . 3_655
N6 Mn1 N3 90.9(3) 3 2_565
N1 Mn1 N3 177.0(2) . 2_565
N9 Mn1 N3 87.7(3) 3_655 2_565
N6 Mn1 N4 90.8(3) 3 .
N1 Mn1 N4 88.6(3) . .
N9 Mn1 N4 175.6(3) 3_655 .
N3 Mn1 N4 88.6(3) 2_565 .
N6 Mn1 N7 176.9(3) 3 .
N1 Mn1 N7 92.1(2) . .
N9 Mn1 N7 90.3(2) 3_655 .
N3 Mn1 N7 86.9(2) 2_565 .
N4 Mn1 N7 87.0(2) . .
C15 N8 C14 121.0(7) . .
C10 N2 C11 120.8(6) . .
C12 N5 C13 122.6(9) . .
N4 C12 N5 170.9(11) . .
C3 O1 C1 113.6(9) . .
N6 C13 N5 171.0(10) . .
C13 N6 Mn1 172.4(8) . 3_545
C11 N3 Mn1 177.4(7) . 2_564
N3 C11 N2 174.0(8) . .
C15 N9 Mn1 139.6(7) . 3_645
N9 C15 N8 173.2(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C8 C9 1.520(14) .
C8 P1 1.819(11) .
C5 C4 1.470(14) .
C4 P1 1.789(9) .
C6 C7 1.501(13) .
C6 P1 1.800(8) .
C1 O1 1.373(12) .
C1 P1 1.800(10) .
C10 N1 1.124(8) .
C10 N2 1.297(9) .
C14 N7 1.141(9) .
C14 N8 1.303(10) .
N4 C12 1.097(10) .
N4 Mn1 2.232(6) .
N7 Mn1 2.269(6) .
N1 Mn1 2.198(6) .
Mn1 N6 2.196(7) 3
Mn1 N9 2.213(6) 3_655
Mn1 N3 2.225(6) 2_565
N8 C15 1.296(11) .
N2 C11 1.307(9) .
N5 C12 1.296(12) .
N5 C13 1.322(12) .
O1 C3 1.367(11) .
C13 N6 1.090(10) .
N6 Mn1 2.196(7) 3_545
N3 C11 1.126(8) .
N3 Mn1 2.225(6) 2_564
N9 C15 1.157(10) .
N9 Mn1 2.213(6) 3_645
