#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/10/09/1100922.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_1100922
_chemical_formula_sum            'C22 H25 Cl N2 O8'
_chemical_formula_weight         480.89
_chemical_name_common            'tetracycline hydrochloride'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9300(9)
_cell_length_b                   12.7162(11)
_cell_length_c                   15.7085(13)
_cell_measurement_reflns_used    6452
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      2.51
_cell_volume                     2183.3(3)
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device_type  'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6883
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0794
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8955
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_coef       0.0038(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         4915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0579P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                3937
_reflns_number_total             4915
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             1000006
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1100922
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.92963(7) 0.41939(6) -0.00197(4) 0.01949(17) Uani 1 1 d . . .
O1 O 0.0086(3) 0.3656(3) 0.43967(14) 0.0392(7) Uani 1 1 d . . .
H1 H 0.039(4) 0.433(4) 0.435(2) 0.047(13) Uiso 1 1 d . . .
O6 O 0.1453(2) 0.46012(16) 0.12979(12) 0.0194(5) Uani 1 1 d . . .
H6 H 0.086(4) 0.449(3) 0.088(2) 0.045(12) Uiso 1 1 d . . .
O11 O 0.7514(2) 0.64335(19) 0.07408(14) 0.0268(5) Uani 1 1 d . . .
O13 O 0.3634(2) 0.71743(18) 0.18883(13) 0.0250(5) Uani 1 1 d . . .
O14 O 0.5800(2) 0.60174(18) 0.29547(12) 0.0212(5) Uani 1 1 d . . .
H14 H 0.565(4) 0.614(3) 0.338(2) 0.033(11) Uiso 1 1 d . . .
O15 O 0.3506(2) 0.60822(17) 0.35612(12) 0.0198(5) Uani 1 1 d . . .
H15 H 0.283(4) 0.580(4) 0.385(2) 0.045(12) Uiso 1 1 d . . .
O17 O 0.1647(2) 0.50211(18) 0.38835(12) 0.0234(5) Uani 1 1 d . . .
O19 O 0.6623(3) 0.81863(18) 0.04211(13) 0.0269(6) Uani 1 1 d . . .
H19 H 0.734(5) 0.757(4) 0.055(3) 0.061(14) Uiso 1 1 d . . .
N10 N 0.7465(3) 0.4488(2) 0.14281(16) 0.0193(6) Uani 1 1 d . . .
H10 H 0.793(4) 0.464(3) 0.100(2) 0.035(11) Uiso 1 1 d . . .
N19 N 0.4694(3) 0.8551(2) 0.08138(17) 0.0288(7) Uani 1 1 d . . .
H19A H 0.475(4) 0.921(3) 0.058(2) 0.034(10) Uiso 1 1 d . . .
H19B H 0.408(4) 0.833(4) 0.112(2) 0.049(14) Uiso 1 1 d . . .
C1 C 0.0207(3) 0.3204(3) 0.36224(18) 0.0272(8) Uani 1 1 d . . .
C2 C -0.0525(4) 0.2345(3) 0.3435(2) 0.0314(9) Uani 1 1 d . . .
H2 H -0.111(3) 0.211(3) 0.388(2) 0.026(9) Uiso 1 1 d . . .
C3 C -0.0436(4) 0.1888(3) 0.2657(2) 0.0302(8) Uani 1 1 d . . .
H3 H -0.084(4) 0.134(3) 0.253(2) 0.040(12) Uiso 1 1 d . . .
C4 C 0.0378(3) 0.2253(3) 0.2036(2) 0.0240(7) Uani 1 1 d . . .
H4 H 0.038(3) 0.189(3) 0.148(2) 0.028(9) Uiso 1 1 d . . .
C5 C 0.1113(3) 0.3105(2) 0.22057(18) 0.0183(7) Uani 1 1 d . . .
C6 C 0.1962(3) 0.3609(2) 0.15436(17) 0.0178(7) Uani 1 1 d . . .
C7 C 0.3178(3) 0.3872(2) 0.19906(16) 0.0145(6) Uani 1 1 d . . .
H7 H 0.337(4) 0.318(3) 0.222(2) 0.028(9) Uiso 1 1 d . . .
C8 C 0.4148(3) 0.4314(2) 0.13903(16) 0.0170(6) Uani 1 1 d . . .
H8A H 0.378(4) 0.486(3) 0.107(2) 0.035(10) Uiso 1 1 d . . .
H8B H 0.444(3) 0.378(3) 0.1001(19) 0.025(9) Uiso 1 1 d . . .
C9 C 0.5241(3) 0.4766(2) 0.18811(16) 0.0141(6) Uani 1 1 d . . .
H9 H 0.554(3) 0.423(3) 0.2292(18) 0.020(8) Uiso 1 1 d . . .
C10 C 0.6283(3) 0.5041(2) 0.12622(17) 0.0156(6) Uani 1 1 d . . .
H10A H 0.615(3) 0.482(2) 0.0715(17) 0.007(7) Uiso 1 1 d . . .
C11 C 0.6526(3) 0.6204(2) 0.11090(16) 0.0180(6) Uani 1 1 d . . .
C12 C 0.5579(3) 0.6923(2) 0.12673(16) 0.0170(6) Uani 1 1 d . . .
C13 C 0.4588(3) 0.6663(2) 0.18199(15) 0.0171(7) Uani 1 1 d . . .
C14 C 0.4828(3) 0.5705(2) 0.24083(15) 0.0150(6) Uani 1 1 d . . .
C15 C 0.3690(3) 0.5439(2) 0.29061(15) 0.0158(6) Uani 1 1 d . . .
C16 C 0.2940(3) 0.4624(2) 0.27178(16) 0.0149(6) Uani 1 1 d . . .
C17 C 0.1867(3) 0.4446(2) 0.32353(16) 0.0184(7) Uani 1 1 d . . .
C18 C 0.1060(3) 0.3578(3) 0.30253(17) 0.0187(7) Uani 1 1 d . . .
C19 C 0.5622(3) 0.7911(2) 0.08265(16) 0.0204(7) Uani 1 1 d . . .
C20 C 0.2161(4) 0.2919(3) 0.0769(2) 0.0246(8) Uani 1 1 d . . .
H20A H 0.135(3) 0.284(3) 0.0479(18) 0.015(8) Uiso 1 1 d . . .
H20B H 0.245(4) 0.225(4) 0.090(2) 0.038(11) Uiso 1 1 d . . .
H20C H 0.259(3) 0.329(3) 0.034(2) 0.025(9) Uiso 1 1 d . . .
C21 C 0.7318(4) 0.3324(3) 0.1384(2) 0.0259(8) Uani 1 1 d . . .
H21A H 0.688(4) 0.311(3) 0.184(2) 0.041(11) Uiso 1 1 d . . .
H21B H 0.810(4) 0.303(3) 0.1312(19) 0.019(9) Uiso 1 1 d . . .
H21C H 0.698(3) 0.321(3) 0.085(2) 0.028(10) Uiso 1 1 d . . .
C22 C 0.8096(4) 0.4811(3) 0.2228(2) 0.0308(9) Uani 1 1 d . . .
H22A H 0.820(3) 0.559(3) 0.223(2) 0.028(9) Uiso 1 1 d . . .
H22B H 0.885(4) 0.458(4) 0.222(2) 0.039(12) Uiso 1 1 d . . .
H22C H 0.761(4) 0.457(3) 0.269(2) 0.030(10) 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'
