#------------------------------------------------------------------------------
#$Date: 2017-09-22 04:14:28 +0200 (vie 22 de sep de 2017) $
#$Revision: 201157 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/92/7229220.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_7229220
loop_
_publ_author_name
'Shemchuk, Oleksii'
'Degli Esposti, Lorenzo'
'Grepioni, Fabrizia'
'Braga, Dario'
_publ_section_title
;
 Ionic co-crystals of enantiopure and racemic histidine with calcium
 halides
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01326D
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C12 H22 Ca N6 O6, 2(I), H2 O'
_chemical_formula_sum            'C12 H24 Ca I2 N6 O7'
_chemical_formula_weight         658.25
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-09-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9123(6)
_cell_length_b                   20.333(2)
_cell_length_c                   23.505(3)
_cell_measurement_reflns_used    732
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4496
_cell_measurement_theta_min      3.2815
_cell_volume                     2347.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.1522
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3715
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.45
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    2.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1619
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0097P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1296
_reflns_number_total             2389
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c7ce01326d2.cif
_cod_data_source_block           cai2-lhi
_cod_original_cell_volume        2347.8(5)
_cod_original_sg_symbol_H-M      C2221
_cod_database_code               7229220
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.18275(19) 0.06156(4) 0.13997(4) 0.0615(3) Uani 1 1 d .
Ca1 Ca 0.5000 0.27209(17) 0.2500 0.0310(8) Uani 1 2 d S
N2 N 0.283(2) 0.4334(5) 0.0726(4) 0.056(3) Uani 1 1 d .
H3 H 0.3671 0.4665 0.0872 0.067 Uiso 1 1 calc R
N3 N -0.2967(17) 0.1863(4) 0.1008(3) 0.038(2) Uani 1 1 d .
H3A H -0.2309 0.1508 0.1183 0.056 Uiso 1 1 calc R
H3B H -0.3556 0.1752 0.0663 0.056 Uiso 1 1 calc R
H3C H -0.4343 0.2027 0.1209 0.056 Uiso 1 1 calc R
N1 N 0.158(2) 0.3575(4) 0.0108(4) 0.038(2) Uani 1 1 d .
C5 C -0.078(2) 0.2367(5) 0.0956(4) 0.028(3) Uani 1 1 d .
H5 H 0.0708 0.2186 0.0726 0.033 Uiso 1 1 calc R
C3 C 0.012(2) 0.3501(6) 0.0595(4) 0.033(3) Uani 1 1 d .
O3 O 0.5000 0.3865(6) 0.2500 0.084(5) Uani 1 2 d S
HW1 H 0.6485 0.4143 0.2532 0.100 Uiso 1 1 d .
C2 C 0.324(3) 0.4073(6) 0.0207(5) 0.051(3) Uani 1 1 d .
H2 H 0.4535 0.4225 -0.0051 0.062 Uiso 1 1 calc R
C6 C 0.033(2) 0.2544(5) 0.1551(4) 0.023(3) Uani 1 1 d .
C4 C -0.195(2) 0.2954(5) 0.0653(4) 0.038(3) Uani 1 1 d .
H4A H -0.3516 0.3116 0.0864 0.046 Uiso 1 1 calc R
H4B H -0.2575 0.2823 0.0279 0.046 Uiso 1 1 calc R
C1 C 0.081(3) 0.3969(6) 0.0973(5) 0.053(4) Uani 1 1 d .
H1 H 0.0064 0.4032 0.1332 0.064 Uiso 1 1 calc R
O5 O 0.5000 0.1568(6) 0.2500 0.092(5) Uani 1 2 d S
HW2 H 0.5674 0.1288 0.2814 0.110 Uiso 1 1 d .
O1 O 0.2824(14) 0.2533(3) 0.1612(2) 0.0325(19) Uani 1 1 d .
O2 O -0.1330(14) 0.2700(4) 0.1906(3) 0.056(3) Uani 1 1 d .
O4 O 0.0000 0.4633(6) 0.2500 0.090(5) Uani 1 2 d S
HW3 H -0.1108 0.4939 0.2214 0.108 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'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 Ca1 O2 177.9(5) 4 1_655
O2 Ca1 O3 91.1(2) 4 .
O2 Ca1 O3 91.1(2) 1_655 .
O2 Ca1 O5 88.9(2) 4 .
O2 Ca1 O5 88.9(2) 1_655 .
O3 Ca1 O5 180.000(2) . .
O2 Ca1 O1 79.3(2) 4 4_655
O2 Ca1 O1 100.4(2) 1_655 4_655
O3 Ca1 O1 99.27(18) . 4_655
O5 Ca1 O1 80.73(18) . 4_655
O2 Ca1 O1 100.4(2) 4 .
O2 Ca1 O1 79.3(2) 1_655 .
O3 Ca1 O1 99.27(18) . .
O5 Ca1 O1 80.73(18) . .
O1 Ca1 O1 161.5(4) 4_655 .
O2 Ca1 C6 97.8(2) 4 4_655
O2 Ca1 C6 82.0(2) 1_655 4_655
O3 Ca1 C6 96.40(19) . 4_655
O5 Ca1 C6 83.60(19) . 4_655
O1 Ca1 C6 18.7(2) 4_655 4_655
O1 Ca1 C6 155.7(2) . 4_655
O2 Ca1 C6 82.0(2) 4 .
O2 Ca1 C6 97.8(2) 1_655 .
O3 Ca1 C6 96.40(19) . .
O5 Ca1 C6 83.60(19) . .
O1 Ca1 C6 155.7(2) 4_655 .
O1 Ca1 C6 18.7(2) . .
C6 Ca1 C6 167.2(4) 4_655 .
C2 N2 C1 106.2(10) . .
C2 N1 C3 105.1(10) . .
N3 C5 C4 108.0(8) . .
N3 C5 C6 109.9(8) . .
C4 C5 C6 112.2(9) . .
C1 C3 N1 110.3(11) . .
C1 C3 C4 128.9(11) . .
N1 C3 C4 120.8(10) . .
N1 C2 N2 111.7(11) . .
O2 C6 O1 126.4(9) . .
O2 C6 C5 116.6(9) . .
O1 C6 C5 116.9(9) . .
O2 C6 Ca1 88.4(6) . .
O1 C6 Ca1 38.2(4) . .
C5 C6 Ca1 154.9(7) . .
C5 C4 C3 111.5(9) . .
C3 C1 N2 106.6(11) . .
C6 O1 Ca1 123.1(6) . .
C6 O2 Ca1 163.9(8) . 1_455
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 O2 2.281(7) 4
Ca1 O2 2.281(7) 1_655
Ca1 O3 2.325(13) .
Ca1 O5 2.343(13) .
Ca1 O1 2.377(6) 4_655
Ca1 O1 2.377(6) .
Ca1 C6 3.220(10) 4_655
Ca1 C6 3.220(10) .
N2 C2 1.346(12) .
N2 C1 1.368(13) .
N3 C5 1.490(11) .
N1 C2 1.322(14) .
N1 C3 1.357(12) .
C5 C4 1.505(12) .
C5 C6 1.545(12) .
C3 C1 1.346(15) .
C3 C4 1.515(14) .
C6 O2 1.210(10) .
C6 O1 1.232(10) .
O2 Ca1 2.281(7) 1_455
