#------------------------------------------------------------------------------
#$Date: 2019-11-23 16:17:41 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/32/1553242.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_1553242
loop_
_publ_author_name
'Jiménez-Sánchez, Arturo'
'Santillan, Rosa'
_publ_section_title
;
 A photochromic-acidochromic HCl fluorescent probe. An unexpected
 chloride-directed recognition.
;
_journal_issue                   13
_journal_name_full               'The Analyst'
_journal_page_first              4108
_journal_page_last               4120
_journal_paper_doi               10.1039/c6an00509h
_journal_volume                  141
_journal_year                    2016
_chemical_formula_sum            'C18 H27 Cl N2 O'
_chemical_formula_weight         322.88
_chemical_name_common            Cinnamaldimine
_chemical_name_systematic        S1
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-12-22 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.16
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.388
_cell_length_b                   6.189
_cell_length_c                   20.392
_cell_measurement_reflns_used    11102
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      3.2
_cell_volume                     1797.469
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Enraf Noniusκ-CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11102
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.178
_diffrn_reflns_theta_min         3.166
_exptl_absorpt_coefficient_mu    0.217
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      1.19
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0552
_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)+(0.0459P)²+0.7446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2637
_reflns_number_total             3883
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6an00509h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1797.5
_cod_original_sg_symbol_Hall     P_2xa
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               1553242
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -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
C1 C 0.11357(14) 0.9005(3) 1.06998(10) 0.0431(5) Uani 1 1 d . .
C2 C 0.15199(14) 1.1004(3) 1.05494(10) 0.0466(5) Uani 1 1 d . .
H2 H 0.1676 1.2014 1.0885 0.056 Uiso 1 1 calc R U
C2A C 0.09109(15) 0.7538(3) 1.01703(10) 0.0479(5) Uani 1 1 d . .
H2A H 0.0649 0.6206 1.0249 0.057 Uiso 1 1 calc R U
C3 C 0.16671(14) 1.1486(3) 0.99158(10) 0.0449(5) Uani 1 1 d . .
H3 H 0.1914 1.2830 0.9831 0.054 Uiso 1 1 calc R U
C3A C 0.10726(15) 0.8045(3) 0.95430(10) 0.0480(5) Uani 1 1 d . .
H3A H 0.0920 0.7039 0.9206 0.058 Uiso 1 1 calc R U
C4 C 0.14585(13) 1.0022(3) 0.93925(10) 0.0417(5) Uani 1 1 d . .
C5 C 0.16721(14) 1.0558(3) 0.87420(10) 0.0471(5) Uani 1 1 d . .
H5 H 0.1915 1.1932 0.8693 0.057 Uiso 1 1 calc R U
C6 C 0.15615(15) 0.9301(4) 0.81964(10) 0.0485(5) Uani 1 1 d . .
H6 H 0.1327 0.7907 0.8220 0.058 Uiso 1 1 calc R U
C7 C 0.17974(14) 1.0074(3) 0.75882(10) 0.0475(5) Uani 1 1 d . .
H7 H 0.2054 1.1451 0.7578 0.057 Uiso 1 1 calc R U
C8 C 0.19243(15) 0.9747(4) 0.64209(10) 0.0502(5) Uani 1 1 d . .
H8A H 0.1846 1.1304 0.6398 0.060 Uiso 1 1 calc R U
H8B H 0.1497 0.9118 0.6061 0.060 Uiso 1 1 calc R U
C9 C 0.29305(14) 0.9185(3) 0.63302(9) 0.0435(5) Uani 1 1 d . .
C10 C 0.31057(16) 1.0087(4) 0.56629(11) 0.0589(6) Uani 1 1 d . .
H10A H 0.2631 0.9531 0.5319 0.071 Uiso 1 1 calc R U
H10B H 0.3043 1.1647 0.5669 0.071 Uiso 1 1 calc R U
C11 C 0.40716(18) 0.9510(5) 0.54943(13) 0.0721(7) Uani 1 1 d . .
H11A H 0.4124 1.0009 0.5050 0.086 Uiso 1 1 calc R U
H11B H 0.4548 1.0240 0.5799 0.086 Uiso 1 1 calc R U
C12 C 0.42410(18) 0.7097(5) 0.55343(14) 0.0798(9) Uani 1 1 d . .
H12A H 0.4880 0.6797 0.5462 0.096 Uiso 1 1 calc R U
H12B H 0.3821 0.6385 0.5187 0.096 Uiso 1 1 calc R U
C13 C 0.40838(17) 0.6189(4) 0.62014(14) 0.0692(7) Uani 1 1 d . .
H13A H 0.4552 0.6771 0.6545 0.083 Uiso 1 1 calc R U
H13B H 0.4155 0.4631 0.6199 0.083 Uiso 1 1 calc R U
C14 C 0.31053(16) 0.6762(4) 0.63520(12) 0.0565(6) Uani 1 1 d . .
H14A H 0.2640 0.6057 0.6032 0.068 Uiso 1 1 calc R U
H14B H 0.3032 0.6221 0.6788 0.068 Uiso 1 1 calc R U
C15 C 0.1190(2) 1.0001(5) 1.18696(12) 0.0791(8) Uani 1 1 d . .
H15A H 0.1040 0.9352 1.2269 0.119 Uiso 1 1 calc R U
H15B H 0.1844 1.0370 1.1926 0.119 Uiso 1 1 calc R U
H15C H 0.0820 1.1283 1.1774 0.119 Uiso 1 1 calc R U
C15A C 0.0576(2) 0.6438(4) 1.14711(12) 0.0682(7) Uani 1 1 d . .
H15D H 0.0526 0.6367 1.1935 0.102 Uiso 1 1 calc R U
H15E H -0.0037 0.6308 1.1218 0.102 Uiso 1 1 calc R U
H15F H 0.0967 0.5281 1.1357 0.102 Uiso 1 1 calc R U
N1 N 0.09853(14) 0.8483(3) 1.13249(9) 0.0555(5) Uani 1 1 d . .
N2 N 0.16764(12) 0.8975(3) 0.70494(9) 0.0483(4) Uani 1 1 d . .
O1 O 0.34878(10) 1.0263(3) 0.68645(7) 0.0588(4) Uani 1 1 d . .
H1 H 0.4045 1.0084 0.6836 0.088 Uiso 1 1 calc R U
Cl10 Cl 0.07460(4) 0.45625(10) 0.71228(3) 0.0680(2) Uani 1 1 d . .
H100 H 0.1427(16) 0.764(4) 0.7049(11) 0.059(7) 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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 122.14(18)
N1 C1 C2A 120.92(18)
C2 C1 C2A 116.94(18)
C3 C2 C1 120.98(18)
C3A C2A C1 121.09(19)
C2 C3 C4 122.16(19)
C2A C3A C4 122.15(19)
C3A C4 C3 116.67(18)
C3A C4 C5 123.18(18)
C3 C4 C5 120.11(18)
C6 C5 C4 127.6(2)
C5 C6 C7 120.9(2)
N2 C7 C6 123.4(2)
N2 C8 C9 112.73(16)
O1 C9 C14 111.53(17)
O1 C9 C10 111.40(18)
C14 C9 C10 109.86(18)
O1 C9 C8 103.97(16)
C14 C9 C8 112.17(18)
C10 C9 C8 107.74(16)
C11 C10 C9 112.82(19)
C12 C11 C10 111.4(2)
C11 C12 C13 111.7(2)
C12 C13 C14 110.7(2)
C9 C14 C13 112.16(19)
C1 N1 C15A 121.61(18)
C1 N1 C15 121.40(19)
C15A N1 C15 116.93(19)
C7 N2 C8 123.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.362(3)
C1 C2 1.407(3)
C1 C2A 1.412(3)
C2 C3 1.372(3)
C2A C3A 1.369(3)
C3 C4 1.400(3)
C3A C4 1.396(3)
C4 C5 1.442(3)
C5 C6 1.348(3)
C6 C7 1.415(3)
C7 N2 1.283(3)
C8 N2 1.459(3)
C8 C9 1.526(3)
C9 O1 1.424(2)
C9 C14 1.520(3)
C9 C10 1.525(3)
C10 C11 1.521(3)
C11 C12 1.513(4)
C12 C13 1.518(4)
C13 C14 1.525(3)
C15 N1 1.452(3)
C15A N1 1.445(3)
